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$1,950,000

MAJOR PRICE REDUCTION — NOW OFFERED AT $1,950,000! Experience the best of the Longboat Key waterfront lifestyle in this beautifully renovated 3-bedroom, 2-bath canal-front residence, ideally positioned just three homes from Sarasota Bay. Offering 1,853 sq. ft. of air-conditioned living space and 2,461 sq. ft. total, this exceptional property combines a premier boating location with extensive recent improvements and a private resort-style pool. Boaters will appreciate the newer seawall, 16,000-lb. boat lift and expansive 18' x 16' Trex dock featuring lighting and water, with easy access to Sarasota Bay and open water. The private Pebble Tec pool and paver pool deck were updated in 2024, creating an inviting setting for relaxing or entertaining. Numerous major improvements provide peace of mind, including a NEW FLAT TILE ROOF (2025), Carrier A/C (2024), A.O. Smith water heater, NuCORE waterproof flooring and plantation shutters. The updated kitchen features elegant Silestone quartz countertops, stainless-steel sink, Bosch 3-door refrigerator/freezer and dishwasher, plus a stainless-steel GE range and microwave. Inside, vaulted ceilings and recessed lighting enhance the spacious living room, while a separate dining room provides an ideal space for entertaining. The desirable split-bedroom floor plan offers privacy, with generous walk-in closets throughout. The primary suite features a walk-in closet with built-ins and an ensuite bath with dual sinks, large tiled shower, whirlpool tub and private water closet. The third bedroom includes a convenient office area, adding flexibility for work or guests. With its rare combination of exceptional boating access, private pool, extensive renovations and proximity to Sarasota Bay, 548 Gunwale Lane presents an outstanding opportunity to own a turnkey waterfront home on Longboat Key. Move in, enjoy the water, and embrace the Longboat Key lifestyle.

3 Beds ⋅ 2 Baths ⋅ A4680965 MLS

MAJOR PRICE REDUCTION — NOW OFFERED AT $1,950,000! Experience the best of the Longboat Key waterfront lifestyle in this beautifully renovated 3-bedroom, 2-bath canal-front residence, ideally positioned just three homes from Sarasota Bay. Offering 1,853 sq. ft. of air-conditioned living space and 2,461 sq. ft. total, this exceptional property combines a premier boating location with extensive recent improvements and a private resort-style pool. Boaters will appreciate the newer seawall, 16,000-lb. boat lift and expansive 18' x 16' Trex dock featuring lighting and water, with easy access to Sarasota Bay and open water. The private Pebble Tec pool and paver pool deck were updated in 2024, creating an inviting setting for relaxing or entertaining. Numerous major improvements provide peace of mind, including a NEW FLAT TILE ROOF (2025), Carrier A/C (2024), A.O. Smith water heater, NuCORE waterproof flooring and plantation shutters. The updated kitchen features elegant Silestone quartz countertops, stainless-steel sink, Bosch 3-door refrigerator/freezer and dishwasher, plus a stainless-steel GE range and microwave. Inside, vaulted ceilings and recessed lighting enhance the spacious living room, while a separate dining room provides an ideal space for entertaining. The desirable split-bedroom floor plan offers privacy, with generous walk-in closets throughout. The primary suite features a walk-in closet with built-ins and an ensuite bath with dual sinks, large tiled shower, whirlpool tub and private water closet. The third bedroom includes a convenient office area, adding flexibility for work or guests. With its rare combination of exceptional boating access, private pool, extensive renovations and proximity to Sarasota Bay, 548 Gunwale Lane presents an outstanding opportunity to own a turnkey waterfront home on Longboat Key. Move in, enjoy the water, and embrace the Longboat Key lifestyle.

548 Gunwale Lane, Longboat Key

$3,750,000

Sanctuary penthouse with spectacular views of the Gulf, and Intracoastal Waterway to Sarasota. *NOW UNFURNISHED*. Total renovations completed in 2023 with nothing overlooked, including but not limited to EFCO turtle-approved glass, high-impact double pane hurricane sliders and windows, crystal custom kitchen cabinets by SRQ Custom Cabinetry, Thermador appliances including induction cooktop, wall-mounted microwave and convection oven, side-by-side Thermador refrigerator, Wi-Fi enabled dryer and hood fan, laundry room with added pantry features and a newly created breakfast bar. Complete water filtration system and quartz countertops throughout, with 5.5-inch baseboards with custom-milled crown molding and trim, solid wood doors, rectified 12-by-60-inch porcelain tile flooring, and custom built-ins in living room and primary bedroom. Hunter Douglas remote-controlled blinds, approximately 10-foot-high ceilings complete with skylights, tankless hot water system, and two zoned air conditioning units installed in 2019 and 2023. Amenities include cable, water and internet. New roof in 2024. Storage locker with under-building parking. Nearly 18 acres with 1,200 feet of Gulf of Mexico beachfront, an Olympic-sized heated pool and spa with extensive pool decks, a fire pit and gazebos to provide shade. A 24/7 guard gate, Har-Tru tennis courts, on-site management, and a two-story clubhouse come complete with a fitness center, showers, saunas and a large entertaining room with catering facilities. Membership to the Longboat Key Club is available which would include six restaurants, 45 holes of golf, 20 tennis courts plus other amenities. You are close to shopping, Publix, CVS, places of worship, a library, town hall and banks, St. Armands Circle along with Sarasota and all it offers.

3 Beds ⋅ 3 Baths ⋅ A4680240 MLS ⋅ 4 BLDG.

Sanctuary penthouse with spectacular views of the Gulf, and Intracoastal Waterway to Sarasota. *NOW UNFURNISHED*. Total renovations completed in 2023 with nothing overlooked, including but not limited to EFCO turtle-approved glass, high-impact double pane hurricane sliders and windows, crystal custom kitchen cabinets by SRQ Custom Cabinetry, Thermador appliances including induction cooktop, wall-mounted microwave and convection oven, side-by-side Thermador refrigerator, Wi-Fi enabled dryer and hood fan, laundry room with added pantry features and a newly created breakfast bar. Complete water filtration system and quartz countertops throughout, with 5.5-inch baseboards with custom-milled crown molding and trim, solid wood doors, rectified 12-by-60-inch porcelain tile flooring, and custom built-ins in living room and primary bedroom. Hunter Douglas remote-controlled blinds, approximately 10-foot-high ceilings complete with skylights, tankless hot water system, and two zoned air conditioning units installed in 2019 and 2023. Amenities include cable, water and internet. New roof in 2024. Storage locker with under-building parking. Nearly 18 acres with 1,200 feet of Gulf of Mexico beachfront, an Olympic-sized heated pool and spa with extensive pool decks, a fire pit and gazebos to provide shade. A 24/7 guard gate, Har-Tru tennis courts, on-site management, and a two-story clubhouse come complete with a fitness center, showers, saunas and a large entertaining room with catering facilities. Membership to the Longboat Key Club is available which would include six restaurants, 45 holes of golf, 20 tennis courts plus other amenities. You are close to shopping, Publix, CVS, places of worship, a library, town hall and banks, St. Armands Circle along with Sarasota and all it offers.

535 Sanctuary Drive Unit C807, Longboat Key

$2,999,000

Nestled along a serene canal just a short ride to beautiful Sarasota Bay, this custom-built John Cannon home offers the perfect blend of luxury, comfort, and coastal living. This two-story, 4-bedroom residence features an open floor plan designed for both relaxation and entertaining. Each bedroom is ensuite, providing privacy and comfort for family and guests alike. Enjoy gathering in the spacious area or entertaining outdoors with a heated pool and spa, a fully equipped outdoor kitchen, and a private dock with a boat lift for effortless access to the water. The home also includes an elevator- ideal for transporting luggage and groceries- and a generous 3- garage with abundant storage. Conveniently located near St. Armands Circle and downtown Sarasota, this property offers easy access to fine dining, shopping , and white-sand beaches, making it a true coastal retreat with every modern amenity.

4 Beds ⋅ 4 Baths ⋅ A4680006 MLS

Nestled along a serene canal just a short ride to beautiful Sarasota Bay, this custom-built John Cannon home offers the perfect blend of luxury, comfort, and coastal living. This two-story, 4-bedroom residence features an open floor plan designed for both relaxation and entertaining. Each bedroom is ensuite, providing privacy and comfort for family and guests alike. Enjoy gathering in the spacious area or entertaining outdoors with a heated pool and spa, a fully equipped outdoor kitchen, and a private dock with a boat lift for effortless access to the water. The home also includes an elevator- ideal for transporting luggage and groceries- and a generous 3- garage with abundant storage. Conveniently located near St. Armands Circle and downtown Sarasota, this property offers easy access to fine dining, shopping , and white-sand beaches, making it a true coastal retreat with every modern amenity.

1005 Bogey Lane, Longboat Key

$550,000

Enjoy tranquil, unobstructed Sarasota Bay views from this top-floor, two-bedroom, two-bath partially furnished residence in the desirable Longboat Harbour community. Fresh paint and updated lighting in some areas of the home enhance the bright, inviting interior, while comfortable living spaces offer peaceful water views from most rooms. The kitchen features stainless steel appliances, the hall bath has been refreshed with timeless finishes, and impact windows plus in-unit washer and dryer hookup add everyday convenience. Longboat Harbour offers resort-style amenities including multiple heated pools, fitness center with sauna, tennis, pickleball, shuffleboard, fishing pier, boating docks up to 34 feet, bike and kayak storage, on-site management, and deeded beach access just across the street with gated parking and facilities. Perfectly located mid-key for relaxed island living.

2 Beds ⋅ 2 Baths ⋅ TB8455704 MLS ⋅ Bldg L BLDG.

Enjoy tranquil, unobstructed Sarasota Bay views from this top-floor, two-bedroom, two-bath partially furnished residence in the desirable Longboat Harbour community. Fresh paint and updated lighting in some areas of the home enhance the bright, inviting interior, while comfortable living spaces offer peaceful water views from most rooms. The kitchen features stainless steel appliances, the hall bath has been refreshed with timeless finishes, and impact windows plus in-unit washer and dryer hookup add everyday convenience. Longboat Harbour offers resort-style amenities including multiple heated pools, fitness center with sauna, tennis, pickleball, shuffleboard, fishing pier, boating docks up to 34 feet, bike and kayak storage, on-site management, and deeded beach access just across the street with gated parking and facilities. Perfectly located mid-key for relaxed island living.

4420 Exeter Drive Unit 303, Longboat Key

$1,395,000

Coastal elegance meets effortless island living at The Player’s Club on Longboat Key. This 2-bedroom, 2.5-bath Gulf-front residence located in building #1 offers direct Gulf views from the private balcony, where nightly sunsets paint the sky in unforgettable color, your front-row seat to paradise. Located in a guard-gated, low-density community with 560 feet of private beachfront, this property delivers rare privacy and an elevated coastal lifestyle. Beach chairs, tables, and umbrellas are provided, making it easy to step outside and enjoy the sand shoreline just moments from your door. The residence offers both elevator and stair access, one assigned covered parking space under the building and convenient guest parking. Owners enjoy resort-style amenities including in ground salt water pool and spa, tennis and pickleball courts, a library and a clubhouse with indoor and outdoor kitchen spaces, perfect for entertaining or relaxing after a day on the water. Ideally positioned on coveted Gulf of Mexico Drive, this prime location places you steps from the St. Regis, minutes to Publix and the world-class dining and shopping of St. Armands Circle. Whether as a full-time residence, seasonal escape or investment opportunity, this condo offers the very best of Longboat Key living- private, serene, and undeniably beautiful. A rare opportunity to own a Gulf-front condo in one of Longboat Key’s most desirable beachfront communities.

2 Beds ⋅ 3 Baths ⋅ A4679674 MLS ⋅ Players Club 1 BLDG.

Coastal elegance meets effortless island living at The Player’s Club on Longboat Key. This 2-bedroom, 2.5-bath Gulf-front residence located in building #1 offers direct Gulf views from the private balcony, where nightly sunsets paint the sky in unforgettable color, your front-row seat to paradise. Located in a guard-gated, low-density community with 560 feet of private beachfront, this property delivers rare privacy and an elevated coastal lifestyle. Beach chairs, tables, and umbrellas are provided, making it easy to step outside and enjoy the sand shoreline just moments from your door. The residence offers both elevator and stair access, one assigned covered parking space under the building and convenient guest parking. Owners enjoy resort-style amenities including in ground salt water pool and spa, tennis and pickleball courts, a library and a clubhouse with indoor and outdoor kitchen spaces, perfect for entertaining or relaxing after a day on the water. Ideally positioned on coveted Gulf of Mexico Drive, this prime location places you steps from the St. Regis, minutes to Publix and the world-class dining and shopping of St. Armands Circle. Whether as a full-time residence, seasonal escape or investment opportunity, this condo offers the very best of Longboat Key living- private, serene, and undeniably beautiful. A rare opportunity to own a Gulf-front condo in one of Longboat Key’s most desirable beachfront communities.

1485 Gulf Of Mexico Drive Unit 303, Longboat Key

$4,400,000

Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key. Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area featuring soaring 23-foot ceilings filled with natural light, rich oak flooring, custom lighting and a gas/wood-burning fireplace. Expansive walls provide the perfect showcase for fine artwork, while the spacious living and dining areas flow seamlessly into a warm family room and a chef’s dream kitchen. The gourmet kitchen is equipped with custom mahogany cabinetry, premium stainless-steel appliances including an induction cooktop, a large island topped with quartzite countertops, and a bright breakfast area overlooking the pool and waterway. Sliding glass doors lead to your private outdoor oasis—a massive 28-foot saltwater pool with solar heating and a partially covered patio with heat-resistant coral stone tile. The luxurious master suite offers two walk-in closets, a sitting area or office, and a spa-inspired bathroom with translucent onyx walls and flooring, a soaking tub, and an oversized shower. Additional features include a large laundry and craft room, an oversized two-car garage with workbench, hurricane-impact windows and doors, reinforced garage doors, and a brand-new concrete tile roof. A beautifully landscaped circular drive welcomes guests, while the deep-water bayou behind the home provides direct access to Sarasota Bay—ideal for boating enthusiasts. Residents of Bay Isles enjoy 24-hour gated security, membership to the Bay Isles Beach Club, and close proximity to the Longboat Key Club, St. Armands Circle, world-class dining, shopping, and the brand-new five -star St. Regis Longboat Key Resort. This exceptional property offers the best of luxury, privacy, and the coveted waterfront lifestyle on Florida’s Gulf Coast. Sellers will repaint exterior of house whatever color Buyer selects before closing, upon firm executed Contract.

4 Beds ⋅ 4 Baths ⋅ A4666688 MLS

Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key. Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area featuring soaring 23-foot ceilings filled with natural light, rich oak flooring, custom lighting and a gas/wood-burning fireplace. Expansive walls provide the perfect showcase for fine artwork, while the spacious living and dining areas flow seamlessly into a warm family room and a chef’s dream kitchen. The gourmet kitchen is equipped with custom mahogany cabinetry, premium stainless-steel appliances including an induction cooktop, a large island topped with quartzite countertops, and a bright breakfast area overlooking the pool and waterway. Sliding glass doors lead to your private outdoor oasis—a massive 28-foot saltwater pool with solar heating and a partially covered patio with heat-resistant coral stone tile. The luxurious master suite offers two walk-in closets, a sitting area or office, and a spa-inspired bathroom with translucent onyx walls and flooring, a soaking tub, and an oversized shower. Additional features include a large laundry and craft room, an oversized two-car garage with workbench, hurricane-impact windows and doors, reinforced garage doors, and a brand-new concrete tile roof. A beautifully landscaped circular drive welcomes guests, while the deep-water bayou behind the home provides direct access to Sarasota Bay—ideal for boating enthusiasts. Residents of Bay Isles enjoy 24-hour gated security, membership to the Bay Isles Beach Club, and close proximity to the Longboat Key Club, St. Armands Circle, world-class dining, shopping, and the brand-new five -star St. Regis Longboat Key Resort. This exceptional property offers the best of luxury, privacy, and the coveted waterfront lifestyle on Florida’s Gulf Coast. Sellers will repaint exterior of house whatever color Buyer selects before closing, upon firm executed Contract.

1571 Harbor Cay Lane, Longboat Key

$2,000,000

Privacy is key for this sprawling, estate-size lot tucked down a quiet street on the north end of Longboat Key. While addressed on Gulf of Mexico Drive, the property is uniquely positioned off the main roadway, set back beyond three estate-sized parcels, offering a tranquil, quiet and peaceful canal-front setting. This rare location offers one of the largest single-family home lots available on Longboat Key and provides a blank canvas to build your dream home, nearly one acre of land, creating the ultimate family estate and a rare opportunity in this area. Featuring approximately 280 feet of canal frontage with access to Sarasota Bay and the Intracoastal Waterway, this sought-after location invites you to fully immerse yourself in the island lifestyle. Enjoy deeded beach access just across the street, where white sand beaches and the sparkling waters of the Gulf of Mexico await. Ideally just a short drive from the shopping and dining of St. Armands Circle, along with golf, tennis, boating, Holmes Beach, Anna Maria Island and all the Sarasota–Bradenton area has to offer, you really can have it all.

A4679439 MLS

Privacy is key for this sprawling, estate-size lot tucked down a quiet street on the north end of Longboat Key. While addressed on Gulf of Mexico Drive, the property is uniquely positioned off the main roadway, set back beyond three estate-sized parcels, offering a tranquil, quiet and peaceful canal-front setting. This rare location offers one of the largest single-family home lots available on Longboat Key and provides a blank canvas to build your dream home, nearly one acre of land, creating the ultimate family estate and a rare opportunity in this area. Featuring approximately 280 feet of canal frontage with access to Sarasota Bay and the Intracoastal Waterway, this sought-after location invites you to fully immerse yourself in the island lifestyle. Enjoy deeded beach access just across the street, where white sand beaches and the sparkling waters of the Gulf of Mexico await. Ideally just a short drive from the shopping and dining of St. Armands Circle, along with golf, tennis, boating, Holmes Beach, Anna Maria Island and all the Sarasota–Bradenton area has to offer, you really can have it all.

6604-6608 Gulf Of Mexico Drive, Longboat Key

$1,000,000

Privacy is key for this sprawling, estate-size lot tucked down a quiet street on the north end of Longboat Key. While addressed on Gulf of Mexico Drive, the property is uniquely positioned off the main roadway, set back beyond three estate-sized parcels, offering a tranquil, quiet and peaceful canal-front setting. This rare location offers one of the largest single-family home lots available on Longboat Key and provides a blank canvas to build your dream home. With the additional purchase of adjacent lot at 6608 Gulf of Mexico Drive, nearly one acre of land can be assembled, creating the ultimate family estate and a rare opportunity in this area. Featuring approximately 140 feet of canal frontage with access to Sarasota Bay and the Intracoastal Waterway, this sought-after location invites you to fully immerse yourself in the island lifestyle. Enjoy deeded beach access just across the street, where white sand beaches and sparkling waters of the Gulf of Mexico await. Ideally just a short drive from shopping and dining of St. Armands Circle, along with golf, tennis, boating, Holmes Beach, Anna Maria Island and all the Sarasota–Bradenton area has to offer, you really can have it all.

A4679263 MLS

Privacy is key for this sprawling, estate-size lot tucked down a quiet street on the north end of Longboat Key. While addressed on Gulf of Mexico Drive, the property is uniquely positioned off the main roadway, set back beyond three estate-sized parcels, offering a tranquil, quiet and peaceful canal-front setting. This rare location offers one of the largest single-family home lots available on Longboat Key and provides a blank canvas to build your dream home. With the additional purchase of adjacent lot at 6608 Gulf of Mexico Drive, nearly one acre of land can be assembled, creating the ultimate family estate and a rare opportunity in this area. Featuring approximately 140 feet of canal frontage with access to Sarasota Bay and the Intracoastal Waterway, this sought-after location invites you to fully immerse yourself in the island lifestyle. Enjoy deeded beach access just across the street, where white sand beaches and sparkling waters of the Gulf of Mexico await. Ideally just a short drive from shopping and dining of St. Armands Circle, along with golf, tennis, boating, Holmes Beach, Anna Maria Island and all the Sarasota–Bradenton area has to offer, you really can have it all.

6604 Gulf Of Mexico Drive, Longboat Key

$1,460,000

Beautifully positioned within Grand Bay on Longboat Key, this 2-bedroom + den residence offers 2,550 sq ft of light-filled living with a private elevator opening directly into the home. Expansive Sarasota Bay views, two generous terraces, and seamless indoor–outdoor flow create an ideal setting for sunsets, bay breezes, and relaxed coastal living. Set behind the gated Bay Isles entrance, residents enjoy resort-style amenities, deeded beach access, and a lifestyle defined by location, comfort, and waterfront elegance. The spacious primary suite offers a tranquil retreat with direct terrace access, peaceful water views, a large walk-in closet, and a spa-like bath featuring dual vanities, a soaking tub, and a walk-in shower. The generous kitchen featuring a Sub-Zero refrigerator and causal eat-in dining, den, and guest suite each open to a second terrace that overlooks Bay Isles’ beautifully landscaped grounds and tennis courts. The den offers versatility for a home office or additional living space, while the guest suite features an en-suite bath and private access to the expansive terrace. A dedicated wine and storage room adds a thoughtful layer of convenience and elegance, blending seamlessly into the home’s well-planned layout. Grand Bay residents enjoy an array of resort-style amenities, including two pools, a fitness center, tennis courts, a clubhouse, and deeded beach access through the Bay Isles Beach Club. Set behind the secure gates of Bay Isles, this residence offers the perfect blend of space, privacy, and the coveted Longboat Key lifestyle. Extremely well managed building- all improvements have been completed!

2 Beds ⋅ 4 Baths ⋅ A4678941 MLS ⋅ Building Ii BLDG.

Beautifully positioned within Grand Bay on Longboat Key, this 2-bedroom + den residence offers 2,550 sq ft of light-filled living with a private elevator opening directly into the home. Expansive Sarasota Bay views, two generous terraces, and seamless indoor–outdoor flow create an ideal setting for sunsets, bay breezes, and relaxed coastal living. Set behind the gated Bay Isles entrance, residents enjoy resort-style amenities, deeded beach access, and a lifestyle defined by location, comfort, and waterfront elegance. The spacious primary suite offers a tranquil retreat with direct terrace access, peaceful water views, a large walk-in closet, and a spa-like bath featuring dual vanities, a soaking tub, and a walk-in shower. The generous kitchen featuring a Sub-Zero refrigerator and causal eat-in dining, den, and guest suite each open to a second terrace that overlooks Bay Isles’ beautifully landscaped grounds and tennis courts. The den offers versatility for a home office or additional living space, while the guest suite features an en-suite bath and private access to the expansive terrace. A dedicated wine and storage room adds a thoughtful layer of convenience and elegance, blending seamlessly into the home’s well-planned layout. Grand Bay residents enjoy an array of resort-style amenities, including two pools, a fitness center, tennis courts, a clubhouse, and deeded beach access through the Bay Isles Beach Club. Set behind the secure gates of Bay Isles, this residence offers the perfect blend of space, privacy, and the coveted Longboat Key lifestyle. Extremely well managed building- all improvements have been completed!

3040 Grand Bay Boulevard Unit 213, Longboat Key

$13,995,000

This Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. Enjoy the ultimate Longboat Key lifestyle with your own direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail. Come and witness the cutting edge of enhanced hurricane construction, wander and enjoy the exquisite staging by Clive Daneil Homes. Situated on a coveted 90' Gulf/Beach-front lot, the property offers soft sands, endless Gulf views, and miles of walkability. In 2025, Longboat Key completed a significant beach re-nourishment project, giving Gulfside Road homeowners one of the widest and deepest stretches of beach on the entire island. Equally notable, Gulfside Road is one of the rare Gulf-side streets set back from the main highway, offering a tranquil, private environment that feels worlds away from the activity of Gulf of Mexico Drive. The main house, elevated over 15 feet, features 11' ceilings, four oversized en-suite bedrooms, and more than 6,600 sq ft of air-conditioned living space, including a grade-level, air-conditioned multipurpose room that can be tailored for wellness, fitness, or a variety of additional lifestyle needs. The wide-open floor plan, generous room sizes, and large impact-rated safety glass sliding doors and windows fill the home with natural light. Two nearly 40' terraces on the main and second floors provide ideal spaces to enjoy the outdoor island lifestyle and breathtaking Gulf views. Interior finishes by Studio G Homes elevate luxury living to the next level. The interior finishes include large-format porcelain tile and hardwood flooring, Italian-imported cabinetry, a custom floating steel-and-wood staircase, a three-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Thermador™ appliance package, AXOR™ and Hansgrohe™ plumbing fixtures, temperature-controlled wine storage, and detailed AV, lighting control, and security systems. Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, Longboard™ premium aluminum architectural details, and a fine light-sand exterior stucco finish. The resort-like pool area and custom spa are surrounded by a lush tropical landscape package. The garage accommodates four cars, with the option to add car lifts. Longboat Key, an 11-mile barrier island, is just minutes from St. Armands Circle and downtown Sarasota. The Sarasota Bradenton International Airport is approximately 25 minutes away. Embrace the opportunity to own this unparalleled residence and experience the pinnacle of coastal luxury living.

4 Beds ⋅ 5 Baths ⋅ A4677413 MLS

This Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. Enjoy the ultimate Longboat Key lifestyle with your own direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail. Come and witness the cutting edge of enhanced hurricane construction, wander and enjoy the exquisite staging by Clive Daneil Homes. Situated on a coveted 90' Gulf/Beach-front lot, the property offers soft sands, endless Gulf views, and miles of walkability. In 2025, Longboat Key completed a significant beach re-nourishment project, giving Gulfside Road homeowners one of the widest and deepest stretches of beach on the entire island. Equally notable, Gulfside Road is one of the rare Gulf-side streets set back from the main highway, offering a tranquil, private environment that feels worlds away from the activity of Gulf of Mexico Drive. The main house, elevated over 15 feet, features 11' ceilings, four oversized en-suite bedrooms, and more than 6,600 sq ft of air-conditioned living space, including a grade-level, air-conditioned multipurpose room that can be tailored for wellness, fitness, or a variety of additional lifestyle needs. The wide-open floor plan, generous room sizes, and large impact-rated safety glass sliding doors and windows fill the home with natural light. Two nearly 40' terraces on the main and second floors provide ideal spaces to enjoy the outdoor island lifestyle and breathtaking Gulf views. Interior finishes by Studio G Homes elevate luxury living to the next level. The interior finishes include large-format porcelain tile and hardwood flooring, Italian-imported cabinetry, a custom floating steel-and-wood staircase, a three-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Thermador™ appliance package, AXOR™ and Hansgrohe™ plumbing fixtures, temperature-controlled wine storage, and detailed AV, lighting control, and security systems. Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, Longboard™ premium aluminum architectural details, and a fine light-sand exterior stucco finish. The resort-like pool area and custom spa are surrounded by a lush tropical landscape package. The garage accommodates four cars, with the option to add car lifts. Longboat Key, an 11-mile barrier island, is just minutes from St. Armands Circle and downtown Sarasota. The Sarasota Bradenton International Airport is approximately 25 minutes away. Embrace the opportunity to own this unparalleled residence and experience the pinnacle of coastal luxury living.

6489 Gulfside Road, Longboat Key

$499,000

Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? This is by far the lowest priced direct beachfront condo on the entire island and it is already completely updated! Whether you decide to use it yourself or use it as an investment with outstanding monthly rental income availability, this is the one. With a fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features storm rated sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!

1 Beds ⋅ 1 Baths ⋅ A4676730 MLS ⋅ 1 BLDG.

Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? This is by far the lowest priced direct beachfront condo on the entire island and it is already completely updated! Whether you decide to use it yourself or use it as an investment with outstanding monthly rental income availability, this is the one. With a fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features storm rated sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!

5231 Gulf Of Mexico Drive Unit 104, Longboat Key

$1,798,000

PRICE POINT ADJUSTMENT ON HIGH FLOOR UNIT! Resort Living At It's Finest with this Grand Bay Condominium offers Privacy in the exclusive Bay Isles community. Grand Bay is situated directly on Bishops Point offering extensive Sarasota City views. Get swepted away by the dramatic unobstructed views of the city and expansive Sarasota Bay. The expansive floor to ceiling"Walls of Windows" with terraces on both the east and west sides of the building. Perfect sunrises and sunsets are the order the day ! The open floor plan from living room, to dining room, to den (can be easily converted into a 3rd bedroom) and the convenience of the kitchen all flow smoothly for entertaining and easy living. The den, kitchen, and guest bedroom all face west with access to the terrace for spectacular sunsets. The kitchen offers all of the latest modern conveniences with an oversized SubZero refrigerator/freezer, mini Perlick bottle refrigerator, Bosch dishwasher, Wolf triple oven with microwave, warming oven and Empava induction cooktop. This unit is sold fully furnished with high end quality names like Ethan Allen, Hancock & Moore and Italian leather. The master bedroom boasts panoramic views of the city and connects to the east terrace with plenty of space for sunbathing and nature watching. The marble master bath invites you to soak in the garden tub to relax the day away. Grand Bay Building 1 Caymen unit offers Total Privacy on the East and West Balconies with Glass railings for unobstructed viewing privacy! The en-suite guest bedroom is currently being used as an office and features its own grand views of the Longboat Key’s Harbourside golf course and the Gulf of Mexico beyond. Grand Bay is situated behind the Longboat Key Club gates and offers additional gated security at the building entrance for your peace of mind. Amenities for your enjoyment include two Har-Tru tennis courts, a state-of-the-art fitness center on the second floor of the Newly modernized Grand Bay clubhouse, two large heated pools and private beach access to the Newly modernized PRIVATE Bay Isles Beach Club directly on the Gulf of America. Grand Bay offers Electric Car Charging Stations. The Travertine stone floors are polished to perfection and is in pristine condition. This is resort style living, at its finest with the convenience of being located on Longboat key. Just minutes from St. Armand's world renowned shopping, restaurants and the cultural capital of Florida that is downtown Sarasota. Memories that will last a lifetime....All offers submitted via FAR-BAR contract form. Please use showing time button for all showings

2 Beds ⋅ 3 Baths ⋅ R4910478 MLS ⋅ Grand Bay One BLDG.

PRICE POINT ADJUSTMENT ON HIGH FLOOR UNIT! Resort Living At It's Finest with this Grand Bay Condominium offers Privacy in the exclusive Bay Isles community. Grand Bay is situated directly on Bishops Point offering extensive Sarasota City views. Get swepted away by the dramatic unobstructed views of the city and expansive Sarasota Bay. The expansive floor to ceiling"Walls of Windows" with terraces on both the east and west sides of the building. Perfect sunrises and sunsets are the order the day ! The open floor plan from living room, to dining room, to den (can be easily converted into a 3rd bedroom) and the convenience of the kitchen all flow smoothly for entertaining and easy living. The den, kitchen, and guest bedroom all face west with access to the terrace for spectacular sunsets. The kitchen offers all of the latest modern conveniences with an oversized SubZero refrigerator/freezer, mini Perlick bottle refrigerator, Bosch dishwasher, Wolf triple oven with microwave, warming oven and Empava induction cooktop. This unit is sold fully furnished with high end quality names like Ethan Allen, Hancock & Moore and Italian leather. The master bedroom boasts panoramic views of the city and connects to the east terrace with plenty of space for sunbathing and nature watching. The marble master bath invites you to soak in the garden tub to relax the day away. Grand Bay Building 1 Caymen unit offers Total Privacy on the East and West Balconies with Glass railings for unobstructed viewing privacy! The en-suite guest bedroom is currently being used as an office and features its own grand views of the Longboat Key’s Harbourside golf course and the Gulf of Mexico beyond. Grand Bay is situated behind the Longboat Key Club gates and offers additional gated security at the building entrance for your peace of mind. Amenities for your enjoyment include two Har-Tru tennis courts, a state-of-the-art fitness center on the second floor of the Newly modernized Grand Bay clubhouse, two large heated pools and private beach access to the Newly modernized PRIVATE Bay Isles Beach Club directly on the Gulf of America. Grand Bay offers Electric Car Charging Stations. The Travertine stone floors are polished to perfection and is in pristine condition. This is resort style living, at its finest with the convenience of being located on Longboat key. Just minutes from St. Armand's world renowned shopping, restaurants and the cultural capital of Florida that is downtown Sarasota. Memories that will last a lifetime....All offers submitted via FAR-BAR contract form. Please use showing time button for all showings

3060 Grand Bay Boulevard Unit 174, Longboat Key

$1,040,000

Huge $100,000 price adjustment and it’s comes TURN Key furnished. Enjoy the best of Gulf-front living in one of the largest units, this 3-bedroom, 3-bath residence with a flexible study/den/4th bedroom, in a gated community located on the sought-after south end of Longboat Key. This residence offers sweeping views of the Gulf of Mexico and includes an enclosed lanai with new telescopes, hurricane windows, and a spacious interior with tile floors in the main living areas and a neutral color palette. A wall of sliding glass doors in the living room opens to a spacious enclosed terrace—perfect for relaxing, dining, and enjoying the sounds of the surf through the new telescoping hurricane windows. The kitchen is large enough for all the chefs in the family. Corian countertops, a tile backsplash, and a breakfast bar that connects easily to the living space. The primary suite includes a Queen-size bed, wake up to view of the Gulf, access to the terrace/lania, and an en-suite bath with a large walk-in shower. For your guests, the second bedroom has an en-suite bathroom. The third bedroom provides a great space for guests or a home office. The private terrace offers views of the beautifully maintained grounds, the beach, and the Gulf beyond. HVAC unit is a 2021 and comes with a transferable maintenance contract with Home-Tec. The Players Club elevates coastal living with resort-style amenities, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, 4 Har-Tru pickleball courts, a putting green, and a heated saltwater pool and spa. This community also has rental opportunities of monthly rentals 12 times per year. Players Club is located just a short drive to St. Armands Circle, where you will enjoy the shopping and dining experiences. Just over the Ringling Bridge, there are many theater options downtown Sarasota. Additional conveniences include on-site management and a 24-hour staffed gate, ensuring comfort and peace of mind.

3 Beds ⋅ 3 Baths ⋅ A4676606 MLS ⋅ 1425 BLDG.

Huge $100,000 price adjustment and it’s comes TURN Key furnished. Enjoy the best of Gulf-front living in one of the largest units, this 3-bedroom, 3-bath residence with a flexible study/den/4th bedroom, in a gated community located on the sought-after south end of Longboat Key. This residence offers sweeping views of the Gulf of Mexico and includes an enclosed lanai with new telescopes, hurricane windows, and a spacious interior with tile floors in the main living areas and a neutral color palette. A wall of sliding glass doors in the living room opens to a spacious enclosed terrace—perfect for relaxing, dining, and enjoying the sounds of the surf through the new telescoping hurricane windows. The kitchen is large enough for all the chefs in the family. Corian countertops, a tile backsplash, and a breakfast bar that connects easily to the living space. The primary suite includes a Queen-size bed, wake up to view of the Gulf, access to the terrace/lania, and an en-suite bath with a large walk-in shower. For your guests, the second bedroom has an en-suite bathroom. The third bedroom provides a great space for guests or a home office. The private terrace offers views of the beautifully maintained grounds, the beach, and the Gulf beyond. HVAC unit is a 2021 and comes with a transferable maintenance contract with Home-Tec. The Players Club elevates coastal living with resort-style amenities, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, 4 Har-Tru pickleball courts, a putting green, and a heated saltwater pool and spa. This community also has rental opportunities of monthly rentals 12 times per year. Players Club is located just a short drive to St. Armands Circle, where you will enjoy the shopping and dining experiences. Just over the Ringling Bridge, there are many theater options downtown Sarasota. Additional conveniences include on-site management and a 24-hour staffed gate, ensuring comfort and peace of mind.

1425 Gulf Of Mexico Drive Unit 308, Longboat Key

$875,000

Investor Dream Home! A double condo unit which feels like a single-family home and comes with 2 attached oversized garage spaces. Elevated among the treetops on the bay side of Longboat Key, this home features wood floors throughout the first elevated living level, an open great room and kitchen for entertaining. There’s an inviting wood-burning fireplace, screened lanai for bay breezes and a flex room to use as an office, den or guest room. Upstairs you will find 3 bedrooms. Two share a full bath while the primary bedroom features a large ensuite and two walk-in closets. You’ll find stunning views of the bay through a wall of windows and a screened lanai where you can catch the sunset glow over the treetops. Amenities in the premier tennis community include exceptional access to bay waters, perfect for launching a kayak, fishing and enjoying the tide pools. Enjoy a boardwalk stroll through mangroves and watch the sunrise from a private bayside dock (no boat access). Pool membership comes with home ownership. Tennis, pickleball and fitness center access is available through Cedars East Resort at an annual rate. Update, redesign and make it your home or income opportunity today!

3 Beds ⋅ 3 Baths ⋅ A4674750 MLS ⋅ 836 BLDG.

Investor Dream Home! A double condo unit which feels like a single-family home and comes with 2 attached oversized garage spaces. Elevated among the treetops on the bay side of Longboat Key, this home features wood floors throughout the first elevated living level, an open great room and kitchen for entertaining. There’s an inviting wood-burning fireplace, screened lanai for bay breezes and a flex room to use as an office, den or guest room. Upstairs you will find 3 bedrooms. Two share a full bath while the primary bedroom features a large ensuite and two walk-in closets. You’ll find stunning views of the bay through a wall of windows and a screened lanai where you can catch the sunset glow over the treetops. Amenities in the premier tennis community include exceptional access to bay waters, perfect for launching a kayak, fishing and enjoying the tide pools. Enjoy a boardwalk stroll through mangroves and watch the sunrise from a private bayside dock (no boat access). Pool membership comes with home ownership. Tennis, pickleball and fitness center access is available through Cedars East Resort at an annual rate. Update, redesign and make it your home or income opportunity today!

836 Evergreen Way, Longboat Key

$2,850,000

Virtually Staged. Under Construction. Under Construction. Pre-Construction | Custom Build | Water to Front & Rear A once-in-a-generation opportunity on one of Longboat Key's most extraordinary streets. Lyons Lane is a truly singular address — a quiet, private enclave in North Longboat Key where homes enjoy an exceptionally rare double-water setting, with sparkling canal frontage to the rear and serene, protected wetland and mangrove views to the front. This is island living at its most private and unspoiled. Design Your Dream Home The vision is still yours to shape. The buyer has the rare opportunity to work directly with the architect to customize the layout, finishes, and features of this brand-new custom home before it's complete. From floor plan adjustments to material selections, this is your chance to create a residence that is uniquely and entirely your own without the years of planning that a true ground-up build typically demands. The property sits on a prime lot with water on both sides; the property includes an existing pool ready to be incorporated into your design, along with a private boat dock and lift with direct access to Millar and Sarasota Bays and no fixed bridges to the Gulf of Mexico. For the boating enthusiast, it simply does not get better than this deep water access, protected dockage, and open water within minutes. Lyons Lane — Longboat's Best-Kept Secret Unlike any other street on the island, Lyons Lane offers homes on one side only, with lush native mangroves lining the opposite side — ensuring that your views, privacy, and natural surroundings will never be compromised. It is one of the few locations on Longboat Key where you can wake up to undisturbed natural beauty in every direction while remaining just moments from the finest dining, boutique shopping, and white-sand Gulf beaches the island has to offer. Longboat Key — Florida's Premier Barrier Island. Stretching 11 miles along Florida's Gulf Coast with over 25 miles of combined waterfront between the Gulf of Mexico and Sarasota Bay, Longboat Key is consistently ranked among the most desirable addresses in the country. The island attracts discerning buyers who demand privacy, natural beauty, and world-class amenities — including the legendary Longboat Key Club, with 45 holes of championship golf, a full-service deep-water marina, spa, and beach club. Opportunities like this — a custom home, double waterfront, dock and lift, and the freedom to personalize are extraordinarily rare on Longboat Key. Don't miss your chance to build exactly the island life you've always envisioned

4 Beds ⋅ 5 Baths ⋅ A4674925 MLS

Virtually Staged. Under Construction. Under Construction. Pre-Construction | Custom Build | Water to Front & Rear A once-in-a-generation opportunity on one of Longboat Key's most extraordinary streets. Lyons Lane is a truly singular address — a quiet, private enclave in North Longboat Key where homes enjoy an exceptionally rare double-water setting, with sparkling canal frontage to the rear and serene, protected wetland and mangrove views to the front. This is island living at its most private and unspoiled. Design Your Dream Home The vision is still yours to shape. The buyer has the rare opportunity to work directly with the architect to customize the layout, finishes, and features of this brand-new custom home before it's complete. From floor plan adjustments to material selections, this is your chance to create a residence that is uniquely and entirely your own without the years of planning that a true ground-up build typically demands. The property sits on a prime lot with water on both sides; the property includes an existing pool ready to be incorporated into your design, along with a private boat dock and lift with direct access to Millar and Sarasota Bays and no fixed bridges to the Gulf of Mexico. For the boating enthusiast, it simply does not get better than this deep water access, protected dockage, and open water within minutes. Lyons Lane — Longboat's Best-Kept Secret Unlike any other street on the island, Lyons Lane offers homes on one side only, with lush native mangroves lining the opposite side — ensuring that your views, privacy, and natural surroundings will never be compromised. It is one of the few locations on Longboat Key where you can wake up to undisturbed natural beauty in every direction while remaining just moments from the finest dining, boutique shopping, and white-sand Gulf beaches the island has to offer. Longboat Key — Florida's Premier Barrier Island. Stretching 11 miles along Florida's Gulf Coast with over 25 miles of combined waterfront between the Gulf of Mexico and Sarasota Bay, Longboat Key is consistently ranked among the most desirable addresses in the country. The island attracts discerning buyers who demand privacy, natural beauty, and world-class amenities — including the legendary Longboat Key Club, with 45 holes of championship golf, a full-service deep-water marina, spa, and beach club. Opportunities like this — a custom home, double waterfront, dock and lift, and the freedom to personalize are extraordinarily rare on Longboat Key. Don't miss your chance to build exactly the island life you've always envisioned

640 Lyons Lane, Longboat Key

$754,900

Rarely available and beautifully positioned, this 3-bedroom, 3-bath fully furnished residence with UNOBSTRUCTED FULL BAY VIEWS invites you to experience true beach-to-bay living in the coveted community of Banyan Bay on the north end of Longboat Key. From sunrise coffees on your private terrace to evenings spent watching dolphins glide across the bay, this home offers an effortless blend of comfort, coastal elegance, and unforgettable daily moments. Set within an intimate community of just 26 Bayside and 18 Gulf side residences, Banyan Bay provides a peaceful retreat with exceptional amenities. Start your mornings with a stroll along your private Gulf beach access, join neighbors for a friendly match on the tennis/pickleball court, launch a kayak directly onto the bay, or unwind by the heated pool after a day on the water. A day dock/fishing pier, fitness center, clubhouse, and convenient bicycle storage further enhance the lifestyle of this warm, social community. Inside, more than 1,400 square feet of thoughtfully designed living space showcases a spacious kitchen with granite countertops, SS appliances, and a breakfast bar and nook ideal for casual dining or gathering with friends. The open great-room layout features soaring ceilings that fill the home with natural light and frame the captivating bayfront scenery. The primary suite offers its own private terrace overlooking the shimmering water—perfect for quiet mornings or evening breezes. A guest suite on the main level ensures comfort and privacy, while a charming spiral staircase leads to a versatile loft and a spacious third bedroom suite—ideal for hosting visitors, working remotely, or enjoying a dedicated creative space. Terra cotta tile flooring throughout the first level brings warmth and coastal character, while Tommy Bahama inspired finishes make this turnkey furnished residence with a NEW AC (Aug 2026) truly move-in-ready. Beyond the community, you’ll find yourself within walking-distance to restaurants and the Centre Shops. Durante Park and the Longboat Key Center for the Arts are just moments away, adding convenience and charm to the neighborhood. Discover the rare combination of lifestyle, location, and waterfront living that only Banyan Bay can offer—where every day feels like a coastal escape.

3 Beds ⋅ 3 Baths ⋅ A4673695 MLS ⋅ 5 BLDG.

Rarely available and beautifully positioned, this 3-bedroom, 3-bath fully furnished residence with UNOBSTRUCTED FULL BAY VIEWS invites you to experience true beach-to-bay living in the coveted community of Banyan Bay on the north end of Longboat Key. From sunrise coffees on your private terrace to evenings spent watching dolphins glide across the bay, this home offers an effortless blend of comfort, coastal elegance, and unforgettable daily moments. Set within an intimate community of just 26 Bayside and 18 Gulf side residences, Banyan Bay provides a peaceful retreat with exceptional amenities. Start your mornings with a stroll along your private Gulf beach access, join neighbors for a friendly match on the tennis/pickleball court, launch a kayak directly onto the bay, or unwind by the heated pool after a day on the water. A day dock/fishing pier, fitness center, clubhouse, and convenient bicycle storage further enhance the lifestyle of this warm, social community. Inside, more than 1,400 square feet of thoughtfully designed living space showcases a spacious kitchen with granite countertops, SS appliances, and a breakfast bar and nook ideal for casual dining or gathering with friends. The open great-room layout features soaring ceilings that fill the home with natural light and frame the captivating bayfront scenery. The primary suite offers its own private terrace overlooking the shimmering water—perfect for quiet mornings or evening breezes. A guest suite on the main level ensures comfort and privacy, while a charming spiral staircase leads to a versatile loft and a spacious third bedroom suite—ideal for hosting visitors, working remotely, or enjoying a dedicated creative space. Terra cotta tile flooring throughout the first level brings warmth and coastal character, while Tommy Bahama inspired finishes make this turnkey furnished residence with a NEW AC (Aug 2026) truly move-in-ready. Beyond the community, you’ll find yourself within walking-distance to restaurants and the Centre Shops. Durante Park and the Longboat Key Center for the Arts are just moments away, adding convenience and charm to the neighborhood. Discover the rare combination of lifestyle, location, and waterfront living that only Banyan Bay can offer—where every day feels like a coastal escape.

5270 Gulf Of Mexico Drive Unit 508, Longboat Key

$975,000

Step inside and be immediately greeted by stunning, uninterrupted views of the Gulf of Mexico, setting the tone for this exceptional Players Club residence. This home is being sold FURNISHED, you just need to bring your toothbrush. The well-appointed kitchen features generous counter space and *stainless steel appliances*, making meal preparation a delight—especially with your own gulf view backdrop. Continue into the spacious living room, where expansive windows draw in the coastal scenery and lead seamlessly to the covered balcony. It’s the perfect place to unwind, entertain, or simply take in the soothing sound of the waves. The primary suite offers private balcony access, a split bathroom layout, and an oversized walk-in closet. Visitors will appreciate the two spacious guest suites ideally located for optimal privacy and relaxing at the end of the day. The Players Club elevates coastal living with resort-style amenities, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, and a heated saltwater pool and spa. The community is ideally located just a short drive from the dining and boutiques of St. Armands Circle and the vibrant cultural offerings of downtown Sarasota. Additional conveniences include on-site management, and a 24-hour staffed gate, ensuring comfort and peace of mind. This residence blends light-filled interiors, generous living spaces, and world-class amenities—offering an exceptional opportunity to enjoy the best of life on the desired southern end of Longboat Key.

3 Beds ⋅ 3 Baths ⋅ A4674194 MLS ⋅ Players Club BLDG.

Step inside and be immediately greeted by stunning, uninterrupted views of the Gulf of Mexico, setting the tone for this exceptional Players Club residence. This home is being sold FURNISHED, you just need to bring your toothbrush. The well-appointed kitchen features generous counter space and *stainless steel appliances*, making meal preparation a delight—especially with your own gulf view backdrop. Continue into the spacious living room, where expansive windows draw in the coastal scenery and lead seamlessly to the covered balcony. It’s the perfect place to unwind, entertain, or simply take in the soothing sound of the waves. The primary suite offers private balcony access, a split bathroom layout, and an oversized walk-in closet. Visitors will appreciate the two spacious guest suites ideally located for optimal privacy and relaxing at the end of the day. The Players Club elevates coastal living with resort-style amenities, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, and a heated saltwater pool and spa. The community is ideally located just a short drive from the dining and boutiques of St. Armands Circle and the vibrant cultural offerings of downtown Sarasota. Additional conveniences include on-site management, and a 24-hour staffed gate, ensuring comfort and peace of mind. This residence blends light-filled interiors, generous living spaces, and world-class amenities—offering an exceptional opportunity to enjoy the best of life on the desired southern end of Longboat Key.

1425 Gulf Of Mexico Drive Unit 408, Longboat Key

$2,325,000

Virtually Staged. Experience the best of Longboat Key living in this elevated coastal retreat, ideally located in the desirable Conrad Beach community just a block from the Gulf of Mexico. Designed with timeless style and modern comfort in mind, this 4-bedroom, 4.5-bath residence offers sophisticated finishes, smart upgrades, and all the pleasures of island life without the upkeep of a private pool. Spanning 2,900 square feet, the open-concept layout showcases a chef’s kitchen with an oversized quartz island, premium appliances, and generous counter space ideal for entertaining family and friends. Light-filled second-level living and dining spaces open to an expansive porch and outdoor dining space , creating a seamless indoor-outdoor flow. The first living level features a serene primary suite with a spa-inspired bath and private balcony, offering a peaceful retreat. Upstairs guest suites provide privacy and comfort, with terraces to capture the island’s cooling breezes and glowing Gulf sunsets. A stunning rooftop deck with jacuzzi crowns the home, creating an unforgettable setting for evening relaxation or gatherings under the stars. Additional highlights include impact-rated windows and doors, elevator ready, and a two-car garage with ample storage. The award-winning Conrad Beach community offers a recently renovated resort-style pool with bath facilities and beautifully maintained landscaping, all just a short stroll from the shoreline. Enjoy the vibrant charm of nearby Anna Maria Island, Longbeach Village dining, marinas, and boutique shopping at St. Armands Circle and Sarasota. This home blends coastal sophistication, privacy, and comfort—an ideal winter haven to share with family and friends.

4 Beds ⋅ 5 Baths ⋅ A4672573 MLS

Virtually Staged. Experience the best of Longboat Key living in this elevated coastal retreat, ideally located in the desirable Conrad Beach community just a block from the Gulf of Mexico. Designed with timeless style and modern comfort in mind, this 4-bedroom, 4.5-bath residence offers sophisticated finishes, smart upgrades, and all the pleasures of island life without the upkeep of a private pool. Spanning 2,900 square feet, the open-concept layout showcases a chef’s kitchen with an oversized quartz island, premium appliances, and generous counter space ideal for entertaining family and friends. Light-filled second-level living and dining spaces open to an expansive porch and outdoor dining space , creating a seamless indoor-outdoor flow. The first living level features a serene primary suite with a spa-inspired bath and private balcony, offering a peaceful retreat. Upstairs guest suites provide privacy and comfort, with terraces to capture the island’s cooling breezes and glowing Gulf sunsets. A stunning rooftop deck with jacuzzi crowns the home, creating an unforgettable setting for evening relaxation or gatherings under the stars. Additional highlights include impact-rated windows and doors, elevator ready, and a two-car garage with ample storage. The award-winning Conrad Beach community offers a recently renovated resort-style pool with bath facilities and beautifully maintained landscaping, all just a short stroll from the shoreline. Enjoy the vibrant charm of nearby Anna Maria Island, Longbeach Village dining, marinas, and boutique shopping at St. Armands Circle and Sarasota. This home blends coastal sophistication, privacy, and comfort—an ideal winter haven to share with family and friends.

333 Firehouse Court, Longboat Key

$1,250,000

It's all about location. Just a short drive from Sarasota, Longboat Key offers unrivaled natural beauty in a coastal retreat. This home/land lot is a 1/3-acre with 100 feet of canal frontage on the desired south side of Longboat Key, and so close to the beach is about as good as it gets. The improvement can be inspected for remediation, and the generous lot features a healthy and substantial seawall on a private and quiet street, offering a golden opportunity for a luxury new build. Seller will offer house plans from a reputable LBK coastal builder, Brista Homes (plan buyer expense). The Buttonwood Community has been touted by the Longboat Observer as the neighborliest neighborhood on Longboat Key and is unique for having its safe harbor, boat ramp and boat slips up to 28 feet for its residents. Florida remains the envy of the country, with many of our markets winning awards for being among the best places to live or retire. It's all about connectivity. Sarasota SRQ Airport’s soaring success added 20 flights, 20% passenger growth, a new runway and terminal in 2024, ranks No. 1 for the fastest-growing airport in the U.S., and ranks No. 1 best resort airport in the entire country, where passengers can get off a plane and feel like their vacation has begun. It's all about investment. Beyond the numbers is the intangible and powerful increase in consumer confidence, which has always proven to enormously influence the housing market, especially luxury and second-home purchases. Longboat Key is the only barrier island on the West Coast of Florida to have relocated all overhead utilities underground for improved reliability and aesthetics, and LBK landed on the Forbes Travel Guide’s list of Top 12 Destinations for 2025. Gov. Ron Desantis announced February 20, 2026, another record-breaking year for tourism in Florida welcomed 143.3 million visitors throughout 2025. An estimated 33.5 million visitors as the highest fourth quarter for visitation on record. According to the release, Florida is the #1 domestic travel destination in the U.S. and a standout choice for international visitors.

A4673355 MLS

It's all about location. Just a short drive from Sarasota, Longboat Key offers unrivaled natural beauty in a coastal retreat. This home/land lot is a 1/3-acre with 100 feet of canal frontage on the desired south side of Longboat Key, and so close to the beach is about as good as it gets. The improvement can be inspected for remediation, and the generous lot features a healthy and substantial seawall on a private and quiet street, offering a golden opportunity for a luxury new build. Seller will offer house plans from a reputable LBK coastal builder, Brista Homes (plan buyer expense). The Buttonwood Community has been touted by the Longboat Observer as the neighborliest neighborhood on Longboat Key and is unique for having its safe harbor, boat ramp and boat slips up to 28 feet for its residents. Florida remains the envy of the country, with many of our markets winning awards for being among the best places to live or retire. It's all about connectivity. Sarasota SRQ Airport’s soaring success added 20 flights, 20% passenger growth, a new runway and terminal in 2024, ranks No. 1 for the fastest-growing airport in the U.S., and ranks No. 1 best resort airport in the entire country, where passengers can get off a plane and feel like their vacation has begun. It's all about investment. Beyond the numbers is the intangible and powerful increase in consumer confidence, which has always proven to enormously influence the housing market, especially luxury and second-home purchases. Longboat Key is the only barrier island on the West Coast of Florida to have relocated all overhead utilities underground for improved reliability and aesthetics, and LBK landed on the Forbes Travel Guide’s list of Top 12 Destinations for 2025. Gov. Ron Desantis announced February 20, 2026, another record-breaking year for tourism in Florida welcomed 143.3 million visitors throughout 2025. An estimated 33.5 million visitors as the highest fourth quarter for visitation on record. According to the release, Florida is the #1 domestic travel destination in the U.S. and a standout choice for international visitors.

615 Buttonwood Drive, Longboat Key

$15,550,000

Where the sky opens wide above the Gulf and the shoreline runs uninterrupted, this extraordinary 12,000+ sq. ft. estate stands with a presence that defies comparison. Set on nearly 200 feet of pristine beachfront, the residence is elevated on pilings and wrapped in walls of glass that pull the Gulf’s horizon into every major living space. Inside, soaring cedar ceilings, exposed trusses, and dramatic lines create a sense of volume and warmth that is both refined and inviting. The great room unfolds beneath grand architectural beams and transitions effortlessly to expansive terraces above the sand. A richly crafted lounge with custom bar and billiards area brings a club-like sophistication to the home’s entertainment spaces. The extraordinary chef’s kitchen commands attention with custom inlaid cabinetry, dual oversized islands, professional-grade appliances, and a hidden pantry—ideal for both catered events and everyday living. The second-floor primary suite serves as a private escape with Gulf views, generous sitting area, and a spa-inspired bath. Additional bedroom suites offer privacy for guests, while flexible spaces—including offices, fitness room with sauna, and bonus areas—accommodate a variety of lifestyles. An elevated pool and spa overlook the beach, complemented by multiple decks and outdoor living areas that capture sunrise, sunset, and the sound of the surf. With two elevators, multi-car garage, and exceptional craftsmanship throughout, this is a residence designed for those who seek scale, presence, and true Gulf-front living.

8 Beds ⋅ 10 Baths ⋅ A4671535 MLS

Where the sky opens wide above the Gulf and the shoreline runs uninterrupted, this extraordinary 12,000+ sq. ft. estate stands with a presence that defies comparison. Set on nearly 200 feet of pristine beachfront, the residence is elevated on pilings and wrapped in walls of glass that pull the Gulf’s horizon into every major living space. Inside, soaring cedar ceilings, exposed trusses, and dramatic lines create a sense of volume and warmth that is both refined and inviting. The great room unfolds beneath grand architectural beams and transitions effortlessly to expansive terraces above the sand. A richly crafted lounge with custom bar and billiards area brings a club-like sophistication to the home’s entertainment spaces. The extraordinary chef’s kitchen commands attention with custom inlaid cabinetry, dual oversized islands, professional-grade appliances, and a hidden pantry—ideal for both catered events and everyday living. The second-floor primary suite serves as a private escape with Gulf views, generous sitting area, and a spa-inspired bath. Additional bedroom suites offer privacy for guests, while flexible spaces—including offices, fitness room with sauna, and bonus areas—accommodate a variety of lifestyles. An elevated pool and spa overlook the beach, complemented by multiple decks and outdoor living areas that capture sunrise, sunset, and the sound of the surf. With two elevators, multi-car garage, and exceptional craftsmanship throughout, this is a residence designed for those who seek scale, presence, and true Gulf-front living.

6685 Gulf Of Mexico Drive, Longboat Key

$769,000

This residence is now available for public and private showings. "One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!” Restricted access resulted in only three private showings in six months. Buyer's have a rare chance to discover a home that’s been under the radar. (Do not let the days on the market fool you. Snowbirds were unable to view this listing the entire "season"). The only coveted South Marina corner/end unit currently on the market at Windward Bay—these special residences are truly prized. End units are usually the first to sell, and for good reason: they offer approximately 250 additional square feet of living space, flooding your home with light and delivering a bright, inviting atmosphere you’ll love. This second-floor location is equally exceptional—it’s the only level where you can enjoy continuous flooring throughout, creating a sleek and modern look. No one below means more freedom, more fun, and more style. Truly extraordinary, this special end unit offers a front-row seat to nature’s most enchanting show. Picture dolphins leaping in the sparkling waters and gentle manatees gliding just below your window—the very reason the current owners fell in love with this home. From breathtaking sunrises to moonlit reflections shimmering across Sarasota Bay, every moment feels like a postcard come to life. Step inside and feel the difference! Where luxury meets comfort with a complete remodel featuring a stunning Thomasville kitchen, sleek new floors, and beautifully updated bathrooms (2022). Enjoy modern conveniences like a Midea refrigerator, remote-control blinds (2025), and most importantly peace of mind with automatic hurricane shutters in the Living and Florida Rooms. This two-bedroom, two-bath property is more than a condo—it’s a lifestyle defined by serenity, security, spectacular views, and maintenance free living. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete, Monthly Condo Fees for 2025 were actually reduced, and the new 2026 Monthly Condo fees only increased by $13. Own the best of Longboat Key Bayfront living and make it yours before it’s just a memory! Paradise has an address..and it's 4500 Gulf of Mexico Drive #G206 on Longboat Key, in the rare gem of a community known as Windward Bay! Contact us today to schedule your private showing. Live the Magic & Don't Miss Out! Your Waterfront Dream Awaits!”

2 Beds ⋅ 2 Baths ⋅ A4671822 MLS ⋅ G-Building BLDG.

This residence is now available for public and private showings. "One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!” Restricted access resulted in only three private showings in six months. Buyer's have a rare chance to discover a home that’s been under the radar. (Do not let the days on the market fool you. Snowbirds were unable to view this listing the entire "season"). The only coveted South Marina corner/end unit currently on the market at Windward Bay—these special residences are truly prized. End units are usually the first to sell, and for good reason: they offer approximately 250 additional square feet of living space, flooding your home with light and delivering a bright, inviting atmosphere you’ll love. This second-floor location is equally exceptional—it’s the only level where you can enjoy continuous flooring throughout, creating a sleek and modern look. No one below means more freedom, more fun, and more style. Truly extraordinary, this special end unit offers a front-row seat to nature’s most enchanting show. Picture dolphins leaping in the sparkling waters and gentle manatees gliding just below your window—the very reason the current owners fell in love with this home. From breathtaking sunrises to moonlit reflections shimmering across Sarasota Bay, every moment feels like a postcard come to life. Step inside and feel the difference! Where luxury meets comfort with a complete remodel featuring a stunning Thomasville kitchen, sleek new floors, and beautifully updated bathrooms (2022). Enjoy modern conveniences like a Midea refrigerator, remote-control blinds (2025), and most importantly peace of mind with automatic hurricane shutters in the Living and Florida Rooms. This two-bedroom, two-bath property is more than a condo—it’s a lifestyle defined by serenity, security, spectacular views, and maintenance free living. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete, Monthly Condo Fees for 2025 were actually reduced, and the new 2026 Monthly Condo fees only increased by $13. Own the best of Longboat Key Bayfront living and make it yours before it’s just a memory! Paradise has an address..and it's 4500 Gulf of Mexico Drive #G206 on Longboat Key, in the rare gem of a community known as Windward Bay! Contact us today to schedule your private showing. Live the Magic & Don't Miss Out! Your Waterfront Dream Awaits!”

4500 Gulf Of Mexico Drive Unit 206, Longboat Key

$3,950,000

A Waterfront Work of Art. Experience a one-of-a-kind waterfront residence on Longboat Key — now offered at an exceptional new value. Designed around three interconnected circular "pods," the residence flows like a choreographed dance. There are no awkward hallways, no wasted corners, no spaces that feel like afterthoughts. Curved walls carry throughout every room — even into the garage — creating a cohesive design statement that's genuinely rare in residential construction at any price point. This architectural masterpiece is a sculptural composition of flowing living spaces connected by custom corridors, delivering remarkable privacy, abundant natural light, and seamless indoor–outdoor living. The dramatic Great Room pod showcases soaring wood-paneled ceilings and expansive walls of glass that frame tranquil water views. The circular primary suite is a private retreat featuring a spa-inspired bath with dual showers, a lounge area, private office, and direct access to the pool and spa terrace. At the heart of the home, the striking circular kitchen is both artful and functional, centered around a curved island beneath a two-story ceiling and skylight, with a thoughtfully designed radial appliance layout. Two en-suite guest bedrooms open to private patios, while the fully self-contained Secondary Primary Suite above the impressive 32' x 23' three-car garage offers independent HVAC, a luxury bath with steam shower and sauna, and flexible living space ideal for extended guests or multigenerational living. Outdoors, the property embraces the waterfront lifestyle with protected deep sailboat water, a private dock with a 12,000-pound lift, and a resort-style pool and spa designed for entertaining and relaxation. Located behind the 24-hour guarded gates of Bay Isles, residents also enjoy exclusive access to the Bay Isles Beach Club on the Gulf of Mexico.

4 Beds ⋅ 6 Baths ⋅ A4671696 MLS

A Waterfront Work of Art. Experience a one-of-a-kind waterfront residence on Longboat Key — now offered at an exceptional new value. Designed around three interconnected circular "pods," the residence flows like a choreographed dance. There are no awkward hallways, no wasted corners, no spaces that feel like afterthoughts. Curved walls carry throughout every room — even into the garage — creating a cohesive design statement that's genuinely rare in residential construction at any price point. This architectural masterpiece is a sculptural composition of flowing living spaces connected by custom corridors, delivering remarkable privacy, abundant natural light, and seamless indoor–outdoor living. The dramatic Great Room pod showcases soaring wood-paneled ceilings and expansive walls of glass that frame tranquil water views. The circular primary suite is a private retreat featuring a spa-inspired bath with dual showers, a lounge area, private office, and direct access to the pool and spa terrace. At the heart of the home, the striking circular kitchen is both artful and functional, centered around a curved island beneath a two-story ceiling and skylight, with a thoughtfully designed radial appliance layout. Two en-suite guest bedrooms open to private patios, while the fully self-contained Secondary Primary Suite above the impressive 32' x 23' three-car garage offers independent HVAC, a luxury bath with steam shower and sauna, and flexible living space ideal for extended guests or multigenerational living. Outdoors, the property embraces the waterfront lifestyle with protected deep sailboat water, a private dock with a 12,000-pound lift, and a resort-style pool and spa designed for entertaining and relaxation. Located behind the 24-hour guarded gates of Bay Isles, residents also enjoy exclusive access to the Bay Isles Beach Club on the Gulf of Mexico.

510 Harbor Gate Way, Longboat Key

$480,000

Live the best of Longboat Key from Longboat Harbour, a gated Bay-to-Beach community where boating, beach days, recreation, and waterfront relaxation are all part of everyday life. This beautifully updated, turnkey second-floor residence offers 2 bedrooms, 2 baths, peaceful water views, and an open floor plan designed for effortless coastal living. What truly sets Longboat Harbour apart is the lifestyle. Just a short walk across the street brings you to the community’s private deeded Gulf beach access, where residents enjoy a full beach house with bathrooms, showers, beach chair storage, and reserved parking. It is easy to grab your chair, head to the sand, take a swim in the Gulf, or settle in for one of Longboat Key’s unforgettable sunsets. For boating enthusiasts, the community’s deep-water marina offers sailboat access with no bridges to the bay, making it easy to enjoy Sarasota Bay and the surrounding waterways. Boat slips are available to residents on a first-come, first-served basis for a nominal fee, with water and electric service available at each slip. There is always something to enjoy at Longboat Harbour, with endless ways to embrace the island lifestyle without ever leaving the community. Residents can take advantage of four heated swimming pools, tennis and pickleball courts, a fitness center, sauna, shuffleboard, putting green, fishing pier, kayak storage and launch area, clubhouse, billiards, card room, library, art studio, woodworking shop, meeting spaces, picnic areas with grills, and beautifully maintained walking paths throughout the property. Beyond the amenities, Longboat Harbour offers a warm and welcoming social atmosphere with planned activities, resident events, and regular community updates, creating plenty of opportunities to connect with neighbors and enjoy the community. Inside the residence, the coastal setting continues with a bright, open living area that extends to an exceptionally spacious screened lanai. Sliding glass doors fill the space with natural light and frame peaceful water views, creating an inviting setting for morning coffee, outdoor dining, or simply relaxing and enjoying the surroundings. The condo was fully updated in 2025 with luxury vinyl plank flooring, refreshed ceilings, fresh paint, and a redesigned kitchen featuring white cabinetry, quartz countertops, a coastal glass backsplash, and a coffee bar. Both bathrooms have also been beautifully renovated with contemporary finishes, including porcelain tile, quartz vanities, and a frameless glass shower in the primary suite. Additional conveniences include a designated covered parking space, the private storage closet on the lanai, and an additional assigned personal storage conveniently located on the second floor near the residence. The monthly association fee includes hazard, hurricane, and flood insurance, and the community’s reserves are fully funded. Owners may also rent their unit up to twice per year, with a minimum lease term of one month, offering added flexibility for those who may wish to enjoy the residence seasonally. For those seeking more than just a residence, Longboat Harbour offers a true island lifestyle where beach, boating, recreation, waterfront living, and community all come together in one exceptional Longboat Key setting, and Unit H202 is the perfect place to enjoy it all with its turnkey interiors, peaceful water views, and beautifully updated coastal style.

2 Beds ⋅ 2 Baths ⋅ A4671530 MLS ⋅ H BLDG.

Live the best of Longboat Key from Longboat Harbour, a gated Bay-to-Beach community where boating, beach days, recreation, and waterfront relaxation are all part of everyday life. This beautifully updated, turnkey second-floor residence offers 2 bedrooms, 2 baths, peaceful water views, and an open floor plan designed for effortless coastal living. What truly sets Longboat Harbour apart is the lifestyle. Just a short walk across the street brings you to the community’s private deeded Gulf beach access, where residents enjoy a full beach house with bathrooms, showers, beach chair storage, and reserved parking. It is easy to grab your chair, head to the sand, take a swim in the Gulf, or settle in for one of Longboat Key’s unforgettable sunsets. For boating enthusiasts, the community’s deep-water marina offers sailboat access with no bridges to the bay, making it easy to enjoy Sarasota Bay and the surrounding waterways. Boat slips are available to residents on a first-come, first-served basis for a nominal fee, with water and electric service available at each slip. There is always something to enjoy at Longboat Harbour, with endless ways to embrace the island lifestyle without ever leaving the community. Residents can take advantage of four heated swimming pools, tennis and pickleball courts, a fitness center, sauna, shuffleboard, putting green, fishing pier, kayak storage and launch area, clubhouse, billiards, card room, library, art studio, woodworking shop, meeting spaces, picnic areas with grills, and beautifully maintained walking paths throughout the property. Beyond the amenities, Longboat Harbour offers a warm and welcoming social atmosphere with planned activities, resident events, and regular community updates, creating plenty of opportunities to connect with neighbors and enjoy the community. Inside the residence, the coastal setting continues with a bright, open living area that extends to an exceptionally spacious screened lanai. Sliding glass doors fill the space with natural light and frame peaceful water views, creating an inviting setting for morning coffee, outdoor dining, or simply relaxing and enjoying the surroundings. The condo was fully updated in 2025 with luxury vinyl plank flooring, refreshed ceilings, fresh paint, and a redesigned kitchen featuring white cabinetry, quartz countertops, a coastal glass backsplash, and a coffee bar. Both bathrooms have also been beautifully renovated with contemporary finishes, including porcelain tile, quartz vanities, and a frameless glass shower in the primary suite. Additional conveniences include a designated covered parking space, the private storage closet on the lanai, and an additional assigned personal storage conveniently located on the second floor near the residence. The monthly association fee includes hazard, hurricane, and flood insurance, and the community’s reserves are fully funded. Owners may also rent their unit up to twice per year, with a minimum lease term of one month, offering added flexibility for those who may wish to enjoy the residence seasonally. For those seeking more than just a residence, Longboat Harbour offers a true island lifestyle where beach, boating, recreation, waterfront living, and community all come together in one exceptional Longboat Key setting, and Unit H202 is the perfect place to enjoy it all with its turnkey interiors, peaceful water views, and beautifully updated coastal style.

4380 Exeter Drive Unit H202, Longboat Key

$580,000

REDUCED AND INCREDIBLE VALUE! EXCEPTIONAL FULL BAY VIEWS, PRIVATE BEACH ACCESS AND KAYAK LAUNCH, HURRICANE-RATED WINDOWS AND SLIDERS, UPDATED BATHS AND MORE! This 2BR/2BA retreat at Pelican Harbour & Beach Club delivers the quintessential Longboat Key lifestyle. From its 2nd-floor vantage point, enjoy peaceful sunrises over the Bay and the tranquil fountain view from your screened lanai, surrounded by lush tropical landscaping. Then, end your day with spectacular Gulf sunsets and leisurely beach walks from your private beach access. The updated kitchen gleams with new 2025 solid quartz countertops, stainless Samsung appliances, a tile backsplash, and a breakfast bar island—perfect for entertaining. Open living and dining areas flow seamlessly toward the water, creating a bright, inviting space ideal for relaxing or hosting friends. The spacious owner’s suite opens to the lanai and features a 2023-renovated ensuite bath with stone countertops, dual sinks, porcelain tile flooring, a glass shower, and custom closets. The guest suite offers another beautifully updated bath and generous storage. Additional highlights in-unit laundry, 2023 roof, 2024 exterior paint, and a hurricane-rated carport conveniently located just outside your door. This unit is currently rented, and tenants will vacate or stay so you can continue to earn rental income immediately! Ideally situated mid-island, Pelican Harbour & Beach Club offers outstanding amenities: Bay and beach access, first-come dock slips, a heated resort-style pool, two newly resurfaced tennis/pickleball courts, a clubhouse with social activities, kayak storage and launch, bike storage, and ample owner storage. This pet-friendly, rental-friendly community welcomes large dogs and seasonal visitors and perfectly combines luxury, flexibility, and coastal charm—just minutes from Bayfront Park, the new St. Regis Resort, St. Armands Circle, and downtown Sarasota’s vibrant restaurants, culture, and shopping.

2 Beds ⋅ 2 Baths ⋅ A4667654 MLS ⋅ Pelican Harbour & Beach Club BLDG.

REDUCED AND INCREDIBLE VALUE! EXCEPTIONAL FULL BAY VIEWS, PRIVATE BEACH ACCESS AND KAYAK LAUNCH, HURRICANE-RATED WINDOWS AND SLIDERS, UPDATED BATHS AND MORE! This 2BR/2BA retreat at Pelican Harbour & Beach Club delivers the quintessential Longboat Key lifestyle. From its 2nd-floor vantage point, enjoy peaceful sunrises over the Bay and the tranquil fountain view from your screened lanai, surrounded by lush tropical landscaping. Then, end your day with spectacular Gulf sunsets and leisurely beach walks from your private beach access. The updated kitchen gleams with new 2025 solid quartz countertops, stainless Samsung appliances, a tile backsplash, and a breakfast bar island—perfect for entertaining. Open living and dining areas flow seamlessly toward the water, creating a bright, inviting space ideal for relaxing or hosting friends. The spacious owner’s suite opens to the lanai and features a 2023-renovated ensuite bath with stone countertops, dual sinks, porcelain tile flooring, a glass shower, and custom closets. The guest suite offers another beautifully updated bath and generous storage. Additional highlights in-unit laundry, 2023 roof, 2024 exterior paint, and a hurricane-rated carport conveniently located just outside your door. This unit is currently rented, and tenants will vacate or stay so you can continue to earn rental income immediately! Ideally situated mid-island, Pelican Harbour & Beach Club offers outstanding amenities: Bay and beach access, first-come dock slips, a heated resort-style pool, two newly resurfaced tennis/pickleball courts, a clubhouse with social activities, kayak storage and launch, bike storage, and ample owner storage. This pet-friendly, rental-friendly community welcomes large dogs and seasonal visitors and perfectly combines luxury, flexibility, and coastal charm—just minutes from Bayfront Park, the new St. Regis Resort, St. Armands Circle, and downtown Sarasota’s vibrant restaurants, culture, and shopping.

4234 Gulf Of Mexico Drive Unit E2, Longboat Key

$799,000

The Ultimate Boater's Foundation! Rare Canal-Front Lot with Twin Lifts & New Seawall! This prime, cleared canal-front lot offers the most turn-key building opportunity on Longboat Key. While other buyers are stuck in the permitting phase for marine infrastructure, this one already has it complete and you can dock your fleet on day one. Unmatched Infrastructure Value: • Brand New Seawall: 100 feet of reinforced concrete seawall installed in 2022, providing maximum protection and a pristine aesthetic. • Dual High-Capacity Lifts: Professionally installed in 2023, featuring a 13,000 lb lift for your primary vessel and a 10,000 lb lift for a secondary boat, skiff, or jet skis. • Deep Water Access: Located on a wide, clean canal with direct access to Sarasota Bay and the Gulf of Mexico—perfect for serious anglers and weekend cruisers alike. The Lifestyle: Located in a quiet, "Old Florida" neighborhood on the north end of the island, you are just a minutes from deeded GULF beach access. After a day on the water, walk to the island’s best restaurants or enjoy the sunset from your private 100-foot waterfront. Investment Specs: • Price: $799,000 • Lot Size: 0.15 Acres (Cleared and Buildable) • Utilities: Public water/sewer connected and ready for hookup. Bonus: Deeded beach access included. Why buy a tear-down when you can start fresh on a lot that already has $150k+ in modern marine upgrades? Bring your builder and your boats.

TB8439776 MLS

The Ultimate Boater's Foundation! Rare Canal-Front Lot with Twin Lifts & New Seawall! This prime, cleared canal-front lot offers the most turn-key building opportunity on Longboat Key. While other buyers are stuck in the permitting phase for marine infrastructure, this one already has it complete and you can dock your fleet on day one. Unmatched Infrastructure Value: • Brand New Seawall: 100 feet of reinforced concrete seawall installed in 2022, providing maximum protection and a pristine aesthetic. • Dual High-Capacity Lifts: Professionally installed in 2023, featuring a 13,000 lb lift for your primary vessel and a 10,000 lb lift for a secondary boat, skiff, or jet skis. • Deep Water Access: Located on a wide, clean canal with direct access to Sarasota Bay and the Gulf of Mexico—perfect for serious anglers and weekend cruisers alike. The Lifestyle: Located in a quiet, "Old Florida" neighborhood on the north end of the island, you are just a minutes from deeded GULF beach access. After a day on the water, walk to the island’s best restaurants or enjoy the sunset from your private 100-foot waterfront. Investment Specs: • Price: $799,000 • Lot Size: 0.15 Acres (Cleared and Buildable) • Utilities: Public water/sewer connected and ready for hookup. Bonus: Deeded beach access included. Why buy a tear-down when you can start fresh on a lot that already has $150k+ in modern marine upgrades? Bring your builder and your boats.

766 Saint Judes Drive N, Longboat Key

$3,590,000

BEACH FRONT OPPORTUNITY on Longboat Key! Rare chance to own DIRECT GULF FRONT property on the coveted south end of Longboat Key in Sarasota county. This charming, 1955 beach cottage sustained significant hurricane damage and is now being sold AS-IS for land value only. No HOA fees! Build your dream coastal retreat on this prime GULF-front lot and enjoy breathtaking sunsets, white-sand beaches- just steps to Publix grocery, 1.5 miles to the stunning St. Regis resort, and easy access to nearby St Armand’s dining/shopping, downtown Sarasota, golf, and marinas. You do not want to miss this opportunity to create your own piece of paradise on BEAUTIFUL Longboat Key!

3 Beds ⋅ 2 Baths ⋅ A4669533 MLS

BEACH FRONT OPPORTUNITY on Longboat Key! Rare chance to own DIRECT GULF FRONT property on the coveted south end of Longboat Key in Sarasota county. This charming, 1955 beach cottage sustained significant hurricane damage and is now being sold AS-IS for land value only. No HOA fees! Build your dream coastal retreat on this prime GULF-front lot and enjoy breathtaking sunsets, white-sand beaches- just steps to Publix grocery, 1.5 miles to the stunning St. Regis resort, and easy access to nearby St Armand’s dining/shopping, downtown Sarasota, golf, and marinas. You do not want to miss this opportunity to create your own piece of paradise on BEAUTIFUL Longboat Key!

2819 Gulf Of Mexico Drive, Longboat Key

$599,000

Virtually Staged. One or more video(s) was virtually staged. Sunny and rarely available 2-bedroom, 2-bath corner residence in BeachPlace III on Longboat Key. This desirable end unit offers a wraparound terrace and open views of lush tropical landscaping, the Longboat Key Club’s Links Golf Course, and partial Gulf views—providing excellent natural light and a true coastal feel. The residence features brand-new, impact-rated floor-to-ceiling sliding glass doors that brighten the living and dining areas and enhance indoor-outdoor living. The open-concept layout connects the kitchen, dining, and living spaces, making it well suited for everyday living or entertaining. A split-bedroom floor plan provides privacy, with the primary suite offering direct access to the terrace. One assigned parking space is included, and the unit is ready for personalization or updating. BeachPlace is a gated, Gulf-front condominium community offering 24-hour security and resort-style amenities, including a clubhouse, heated beachfront pool and spa, tennis courts, fitness center, and a private boardwalk with direct beach access. Seasonal beach service with lounge chairs and umbrellas is provided. Conveniently located near golf, marinas, dining, and shopping, and just a short drive to downtown Sarasota, this property offers flexibility as a full-time residence, seasonal getaway, or investment opportunity.

2 Beds ⋅ 2 Baths ⋅ A4669086 MLS ⋅ Building 10 BLDG.

Virtually Staged. One or more video(s) was virtually staged. Sunny and rarely available 2-bedroom, 2-bath corner residence in BeachPlace III on Longboat Key. This desirable end unit offers a wraparound terrace and open views of lush tropical landscaping, the Longboat Key Club’s Links Golf Course, and partial Gulf views—providing excellent natural light and a true coastal feel. The residence features brand-new, impact-rated floor-to-ceiling sliding glass doors that brighten the living and dining areas and enhance indoor-outdoor living. The open-concept layout connects the kitchen, dining, and living spaces, making it well suited for everyday living or entertaining. A split-bedroom floor plan provides privacy, with the primary suite offering direct access to the terrace. One assigned parking space is included, and the unit is ready for personalization or updating. BeachPlace is a gated, Gulf-front condominium community offering 24-hour security and resort-style amenities, including a clubhouse, heated beachfront pool and spa, tennis courts, fitness center, and a private boardwalk with direct beach access. Seasonal beach service with lounge chairs and umbrellas is provided. Conveniently located near golf, marinas, dining, and shopping, and just a short drive to downtown Sarasota, this property offers flexibility as a full-time residence, seasonal getaway, or investment opportunity.

1065 Gulf Of Mexico Drive Unit 201, Longboat Key

$1,700,000

$100,000 PRICE REDUCTION!!! Live the ultimate Florida Waterfront lifestyle in this private, calm, secure, spacious and elegant large elevated coastal home. Located on the North end of Longboat Key less than a mile to Anna Maria Island in the relaxed Sleepy Lagoon neighborhood with deeded beach access just around the corner, leading you to never crowded stretches of sand. The home is located on a boating canal just three houses in from the bay offering direct access to Sarasota Bay and the Intercoastal Waterway. This large ( 5328 SF total) very well maintained and upgraded elevated home offers 2800 SF on the main living level plus 2500 SF of bonus space on the first floor with an elevator. This elevated, well-built custom home sustained no damage nor have any flood claims ever been filed. This home spans two level of living and has an open floor plan, blending indoor and outdoor living. The main living area is upstairs with large flowing open rooms, vaulted ceilings, a fireplace and features French Doors leading to a screened Lanai overlooking the natural canal with foliage for privacy. The bedrooms are arranged in a split plan with each having en-suite bathrooms with lots of closets and built-ins. The large eat-in kitchen has custom cabinetry with crown molding, pull-outs, granite countertops and stainless appliances plus a large separate dining room perfect for all your family or friends. Just off the kitchen on the main living level is a very large laundry room along with all the closets in this home you will have all the storage you need. On the first level is the open foyer leading up to the living area with the elevator access and oversized split garages. There is an additional 2500 SF of AC/heated of interior space that is finished with polished concrete floors and walls of sliding doors leading to the pool area, porch, deck, yard and dock area. Also just outside your bonus space is private 60’ long screened, heated lap pool with a full bath. The property would provide great renal income also for a part time owner as it has in the past. Walk the beach, swim in the pool or ocean, ride your bike on the Longboat Key Bike path, fish, boat, kayak, paddle board, jet ski and enjoy your spacious home that is just a short drive to Sarasota, St. Armand’s circle and Anna Maria Island. Please see the videos. What are you waiting for? Start living the dream.

3 Beds ⋅ 4 Baths ⋅ A4669634 MLS

$100,000 PRICE REDUCTION!!! Live the ultimate Florida Waterfront lifestyle in this private, calm, secure, spacious and elegant large elevated coastal home. Located on the North end of Longboat Key less than a mile to Anna Maria Island in the relaxed Sleepy Lagoon neighborhood with deeded beach access just around the corner, leading you to never crowded stretches of sand. The home is located on a boating canal just three houses in from the bay offering direct access to Sarasota Bay and the Intercoastal Waterway. This large ( 5328 SF total) very well maintained and upgraded elevated home offers 2800 SF on the main living level plus 2500 SF of bonus space on the first floor with an elevator. This elevated, well-built custom home sustained no damage nor have any flood claims ever been filed. This home spans two level of living and has an open floor plan, blending indoor and outdoor living. The main living area is upstairs with large flowing open rooms, vaulted ceilings, a fireplace and features French Doors leading to a screened Lanai overlooking the natural canal with foliage for privacy. The bedrooms are arranged in a split plan with each having en-suite bathrooms with lots of closets and built-ins. The large eat-in kitchen has custom cabinetry with crown molding, pull-outs, granite countertops and stainless appliances plus a large separate dining room perfect for all your family or friends. Just off the kitchen on the main living level is a very large laundry room along with all the closets in this home you will have all the storage you need. On the first level is the open foyer leading up to the living area with the elevator access and oversized split garages. There is an additional 2500 SF of AC/heated of interior space that is finished with polished concrete floors and walls of sliding doors leading to the pool area, porch, deck, yard and dock area. Also just outside your bonus space is private 60’ long screened, heated lap pool with a full bath. The property would provide great renal income also for a part time owner as it has in the past. Walk the beach, swim in the pool or ocean, ride your bike on the Longboat Key Bike path, fish, boat, kayak, paddle board, jet ski and enjoy your spacious home that is just a short drive to Sarasota, St. Armand’s circle and Anna Maria Island. Please see the videos. What are you waiting for? Start living the dream.

569 Juan Anasco Drive, Longboat Key

$4,295,000

New Construction - Discover the epitome of waterfront luxury with this newly built home in the heart of Longboat Key—competitively priced and move-in ready. Nestled along a private canal, this 5-bedroom plus den, 4,106 sq ft residence blends contemporary sophistication with coastal appeal. Designed for effortless indoor-outdoor living, the home boasts two spacious lanais, a private pool and spa, and an elevated foundation at 9.5 feet for added peace of mind. Boaters will enjoy concrete canal bulkhead with quick access to the Gulf of Mexico, perfect for endless days on the water. Inside, the home features engineered hardwood flooring, sleek quartz countertops throughout, a large walk-in pantry, and the convenience of dual laundry rooms. Set in a tranquil, private location just minutes from Longboat Key’s renowned beaches, golf courses, and upscale dining, this home is a rare gem. Don’t miss your opportunity to own a waterfront retreat in one of Florida’s most sought-after coastal communities.

6 Beds ⋅ 6 Baths ⋅ A4669195 MLS

New Construction - Discover the epitome of waterfront luxury with this newly built home in the heart of Longboat Key—competitively priced and move-in ready. Nestled along a private canal, this 5-bedroom plus den, 4,106 sq ft residence blends contemporary sophistication with coastal appeal. Designed for effortless indoor-outdoor living, the home boasts two spacious lanais, a private pool and spa, and an elevated foundation at 9.5 feet for added peace of mind. Boaters will enjoy concrete canal bulkhead with quick access to the Gulf of Mexico, perfect for endless days on the water. Inside, the home features engineered hardwood flooring, sleek quartz countertops throughout, a large walk-in pantry, and the convenience of dual laundry rooms. Set in a tranquil, private location just minutes from Longboat Key’s renowned beaches, golf courses, and upscale dining, this home is a rare gem. Don’t miss your opportunity to own a waterfront retreat in one of Florida’s most sought-after coastal communities.

530 De Narvaez Drive, Longboat Key

$2,400,000

Fractional Ownership. Fractional Ownership Opportunity at The St. Regis Longboat Key. Each purchase includes complimentary Resort Membership, valued at $125,000, along with the added benefit of no annual dues (a $14,000 value) and no minimum annual expenditure requirements. The Resort Membership can be enjoyed year-round, providing exceptional value and convenience to owners. For 2026, fee for each 30 day interset is $19,992. This comprehensive fee covers a wide range of services and expenses, including Condo fees, Property taxes, Utilities, Housekeeping services, Property management, Insurance, Furniture replacement reserve, and Maintenance reserve. This elegant and gracious two-bedroom St. Regis residence is owned by a limited liability company (LLC), offering a distinctive ownership structure where shares are allocated in 30 day segments. Prospective buyers have the opportunity to purchase one or more 30 day segments May through October, with each 30 day segment available at a price of $400,000. This condominium is designed with spacious rooms, expansive glass windows, and soaring ceilings that create an airy and inviting atmosphere. The gourmet kitchen is well-appointed with premium Wolf and Sub-Zero appliances, including a gas cooktop, double ovens, and a side-by-side refrigerator, making it ideal for culinary enthusiasts. The large owner's suite offers a luxurious primary bath featuring double vanities, a deep soaking tub, a frameless walk-in shower, and a private water closet. The residence is being sold fully furnished with pieces from Restoration Hardware. With walls of glass opening to the large wraparound private terrace, owners can host memorable gatherings with stylish furnishings, an outdoor gas grill, and offering stunning views of Sarasota Bayfront. Additional conveniences include a private two-car garage on the first level and easy access to a semi-private elevator that opens directly into the residence. Nestled within the first branded residential community and ultra-luxury five-star resort on the Gulf of Mexico, The Residences at The St. Regis Longboat Key combine legendary service with the tranquil allure of a secluded seaside getaway on Longboat Key, Florida. The community spans over 17 acres and boasts 800 feet of direct beachfront, offering residents an unparalleled lifestyle. Amenities include signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in-residence dining, a private resident-only pool and spa, a Clubhouse, a fitness center, and beachside cabanas. Experience the finest in fractional luxury living at The St. Regis Longboat Key.

2 Beds ⋅ 3 Baths ⋅ A4668544 MLS ⋅ N/A BLDG.

Fractional Ownership. Fractional Ownership Opportunity at The St. Regis Longboat Key. Each purchase includes complimentary Resort Membership, valued at $125,000, along with the added benefit of no annual dues (a $14,000 value) and no minimum annual expenditure requirements. The Resort Membership can be enjoyed year-round, providing exceptional value and convenience to owners. For 2026, fee for each 30 day interset is $19,992. This comprehensive fee covers a wide range of services and expenses, including Condo fees, Property taxes, Utilities, Housekeeping services, Property management, Insurance, Furniture replacement reserve, and Maintenance reserve. This elegant and gracious two-bedroom St. Regis residence is owned by a limited liability company (LLC), offering a distinctive ownership structure where shares are allocated in 30 day segments. Prospective buyers have the opportunity to purchase one or more 30 day segments May through October, with each 30 day segment available at a price of $400,000. This condominium is designed with spacious rooms, expansive glass windows, and soaring ceilings that create an airy and inviting atmosphere. The gourmet kitchen is well-appointed with premium Wolf and Sub-Zero appliances, including a gas cooktop, double ovens, and a side-by-side refrigerator, making it ideal for culinary enthusiasts. The large owner's suite offers a luxurious primary bath featuring double vanities, a deep soaking tub, a frameless walk-in shower, and a private water closet. The residence is being sold fully furnished with pieces from Restoration Hardware. With walls of glass opening to the large wraparound private terrace, owners can host memorable gatherings with stylish furnishings, an outdoor gas grill, and offering stunning views of Sarasota Bayfront. Additional conveniences include a private two-car garage on the first level and easy access to a semi-private elevator that opens directly into the residence. Nestled within the first branded residential community and ultra-luxury five-star resort on the Gulf of Mexico, The Residences at The St. Regis Longboat Key combine legendary service with the tranquil allure of a secluded seaside getaway on Longboat Key, Florida. The community spans over 17 acres and boasts 800 feet of direct beachfront, offering residents an unparalleled lifestyle. Amenities include signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in-residence dining, a private resident-only pool and spa, a Clubhouse, a fitness center, and beachside cabanas. Experience the finest in fractional luxury living at The St. Regis Longboat Key.

1591 Gulf Of Mexico Drive Unit 512, Longboat Key