Longboat Key Homes with Courtyard Exterior Features

Longboat Key Homes with Courtyard Exterior Features

Welcome to Longboat Key, Florida – a stunning coastal paradise that perfectly blends luxury living with the charm of a small town. Nestled in the Gulf of Mexico, this idyllic barrier island boasts pristine beaches, crystal-clear waters, and an inviting community atmosphere. Residents and visitors alike can enjoy a variety of outdoor activities, including boating, fishing, and sunbathing on the soft, sandy shores. With a vibrant dining scene, upscale boutiques, and a plethora of recreational options, Longboat Key is the ideal destination for those seeking a relaxed yet sophisticated lifestyle.

One of the standout features of homes in this enchanting area is the exquisite courtyard exterior. These thoughtfully designed homes often feature private courtyards that serve as tranquil retreats, perfect for enjoying the Florida sunshine or hosting intimate gatherings with friends and family. Imagine sipping your morning coffee surrounded by lush landscaping or unwinding in the evening with a gentle breeze rustling through the palm trees. The courtyard design not only enhances privacy but also creates a seamless indoor-outdoor living experience, allowing residents to fully embrace the beauty of Longboat Key's natural surroundings.

Whether you’re seeking a luxurious waterfront estate or a charming villa, Longboat Key offers a diverse range of properties with stunning courtyard features. Discover the perfect home that complements your lifestyle, where every day feels like a vacation in this enchanting slice of paradise. Embrace the allure of Longboat Key, where your dream home awaits amidst the sun, sand, and serenity of Florida’s Gulf Coast.

Newest Longboat Key Homes with Courtyard Exterior Features

3 Beds ⋅ 2 Baths ⋅ A4705924 MLS ⋅ 1 BLDG.

Welcome to effortless Gulf-front living at Club Longboat Beach & Tennis Resort, one of Longboat Key’s most established and sought-after beachfront communities. This beautifully updated 3-bedroom, 2-bath residence is offered TURNKEY FURNISHED, making it an exceptional opportunity for a full-time residence, coastal retreat, or income-producing investment. Located in desirable Building 1, this spacious first-floor residence offers approximately 1,484 square feet of comfortable, thoughtfully designed living space with the rare convenience of no elevators or long walks. The open, split-bedroom floor plan features wide-plank flooring, a light and inviting coastal palette, and an easy flow for both everyday living and entertaining. The updated kitchen is the heart of the home, featuring crisp white cabinetry, stainless steel appliances, under-cabinet lighting, a glass tile backsplash, and a large center island with seating. Floor-to-ceiling sliders in the great room open to a private, lushly landscaped patio, extending the living space outdoors and creating a peaceful place to enjoy the Longboat Key lifestyle. The spacious primary suite offers direct patio access, a beautifully updated bath with walk-in glass shower, and generous closet space. Two additional bedrooms provide flexibility for family and guests, including a den/third bedroom with Murphy bed. A second full bath, full-size washer and dryer, additional laundry cabinetry and abundant storage complete the interior. Just outside your front door are a private storage room and covered parking space, with ample additional guest and resident parking throughout the community. Club Longboat offers approximately 750 feet of direct Gulf-front beach and an exceptional resort-style lifestyle. Amenities include 8 Har-Tru tennis courts, several lighted for evening play, an on-site tennis professional, pickleball, two heated swimming pools including separate adult and family pool areas, spa/whirlpool, sauna, beach chairs and umbrellas, grilling areas, bocce, fishing, on-site management and an active social calendar. A new clubhouse with fitness and social spaces is also planned as part of the community’s hurricane restoration, with exciting improvements ahead. Owners enjoy a truly welcoming community with regular social events, including Friday happy hours and seasonal celebrations. Club Longboat is also pet-friendly for owners and offers exceptional rental flexibility, with a 30-day minimum and up to 12 leases per year. For buyers looking to offset ownership costs, this residence offers a particularly compelling advantage: a strong, proven rental history with substantial demand and existing future bookings. The combination of a three-bedroom floor plan, turnkey furnishings, direct Gulf access and flexible leasing has made this an exceptionally desirable rental. Ideally situated on the Gulf side of Longboat Key, you are minutes from outstanding dining, boating, golf and recreation, with the shops and restaurants of St. Armands Circle and the arts and culture of downtown Sarasota just a short drive away. Whether you are searching for a turnkey beach home, seasonal escape, or investment property, this beautifully furnished Club Longboat residence offers the combination buyers want most: DIRECT GULF ACCESS, RESORT-STYLE AMENITIES, THREE BEDROOMS, RENTAL FLEXIBILITY and the unmistakable lifestyle of Longboat Key. Simply arrive, unpack and head to the beach.

5055 Gulf Of Mexico Drive Unit 115, Longboat Key

A 58 ft. x 20 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. Max length of vessel allowed is 53 LOA, usable beam is 18 ft at the head of the slip. A current photo of the vessel must be provided, and the vessel approved by the Association before entering the marina.

2800 Harbourside Drive Drive Unit M-10, Longboat Key

2 Beds ⋅ 2 Baths ⋅ A4703984 MLS ⋅ Longboat Arms BLDG.

Longboat Arms - 2BR / 2BA / 1,187 sq ft - Bring your boat and enjoy a slice of paradise! This lovely second-floor condo offers views of the bay, pool, and marina from the front. Open and light-filled, it features a covered front porch and was completely remodeled in 2017. Highlights include all-new hurricane-impact windows, a kitchen with stainless steel appliances and granite countertops, and a hall closet with washer/dryer hookup (or use the convenient laundry facility on the same floor). Tastefully decorated and move-in ready. Located in the low-density Longboat Arms community of just 45 residences with approximately 1,000 feet of waterfront and abundant green space. Enjoy covered parking, a private community boat ramp (perfect for boats, kayaks, paddleboards, jet skis), and offering boat dockage - available to residents on waitlist basis (currently open), heated pool, tennis court, outdoor amenities, and deeded Gulf beach access just across the street. The separate community building is currently undergoing extensive renovation. This is an outstanding opportunity for full-time living, a seasonal retreat, or a smart investment in one of mid-island Longboat Key’s most appealing bay-side communities. Don’t miss your chance to own in Longboat Arms — schedule your private showing today!

3320 Gulf Of Mexico Drive Unit 206C, Longboat Key

A much sought after inside-the-T 48 x 23.5 foot slip at Longboat Key Club Moorings! Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping - close to Publix, CVS, and other specialty shops - recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 43 LOA; beam depends on the vessel. Call to discuss!

2600 Harbourside Drive Unit Q-10, Longboat Key

1 Beds ⋅ 1 Baths ⋅ A4702801 MLS

GET EXCITED ABOUT THIS ONE on Longboat Key! Not just because of the LOCATION, but because of the opportunity to finish making it your own which includes the following (not yet installed) materials: new windows, new flooring, new cabinetry, high-end appliances, ship-lap, as well as the furnishings. AND, you will get to enjoy the NEWLY RENOVATED CLUBHOUSE, which is almost complete. Brand new Tiki Hut coming soon on the beach, as well. Did I mention the extremely affordable HOA fees, which is rare on Longboat Key? Twin Shores is a unique 55+ Gulf-to-Bay community offering access to both the beach and Sarasota Bay. This charming 1-bedroom, 1-bath home (with another full-bath outside) is ready for its next owner to complete the renovation and create their own island retreat. (Also, the owner had plans to install the existing shuttered doors to create an optional temporary 2nd bedroom for overnight guests!) Renovation work has already begun, giving you the opportunity to finish the home to your personal taste and style. This home can be your inviting Longboat Key getaway or full-time island residence. What truly sets this opportunity apart is that Twin Shores has the best of both worlds in this resident-owned Gulf-to-Bay cooperative community, with private deeded Gulf beach access, Sarasota Bay access, marina, community pool and clubhouse. Spend your mornings walking the beach, your afternoons boating or relaxing by the pool, and your evenings enjoying game nights in the clubhouse as well as everything Longboat Key has to offer. Opportunities at this price point on Longboat Key are increasingly hard to find. Offered AS-IS. Renovation is incomplete and the appliances, cabinetry, flooring, and windows at the property are included in the sale. Twin Shores Beach and Marina offers a saltwater/heated community pool, a marina with boat slips available for lease (current waitlist), a beautiful, new clubhouse (almost completed) with plenty of community activities and social events. This community offers an array of outdoor activities because of its beach-to-bay location: Enjoy kayaking, paddle boarding, biking, boating and fishing. Love pickleball? Bayfront Park is a short walk or bike ride away which offers pickleball for all levels. Twin Shores Beach and Marina is a remnant of Old Florida with extremely affordable community fees at $280/month which includes water, sewer, trash, pool maintenance, clubhouse, management, marina, maintenance grounds and common area taxes. Enjoy million-dollar sunrises from the marina and million-dollar sunsets from the deeded beach without the typical Longboat Key million-dollar-plus price tag!

36 Twin Shores Boulevard, Longboat Key

2 Beds ⋅ 2 Baths ⋅ A4702237 MLS ⋅ Bldg B Portobello BLDG.

Welcome to Portobello, a Gulf to Bay community on mid Longboat Key where residents enjoy their own private beach access just across the street and a bayside dock right outside the door. This beautifully remodeled, turnkey furnished fifth floor condo overlooks the quiet waters of Cranes Bayou, positioned to catch soft morning light while the terrace stays comfortably shaded through the afternoon. Inside, the open floor plan is filled with natural light and finished with new laminate wood flooring, crown molding, plantation shutters, and new light fixtures throughout. The updated kitchen offers stainless steel appliances, custom white cabinetry with crown molding, under cabinet lighting, and a breakfast bar that opens to the dining area. The split bedroom layout is ideal for hosting guests. The oversized primary suite features its own water views, space for a king sized bed, an oversized walk in closet, and an en suite bath with a smart split sink and shower design, while the equally spacious second bedroom sits beside a fully updated second bath. A sleeper sofa in the living room allows the condo to comfortably sleep six, and an in unit washer and dryer adds everyday convenience. The full length screened terrace spans the entire width of the unit and is accessible through new impact sliding doors from the living room and both bedrooms, so the water view follows you from room to room. Portobello's amenities complete the picture. A BRAND NEW AC unit was installed in September 2026, ensuring peace of mind for years to come. Residents enjoy a heated pool with tennis courts, a fully renovated recreation room, kayak and canoe storage with a launch area, and a dock and walkway for fishing or docking your boat for up to two days. A bayside picnic area with a gas grill and umbrella tables sits near the kayak launch, perfect for sunset cookouts by the water. Just across the street, Portobello's private beach access puts the Gulf and its sugar sand shoreline a short stroll from your door, complete with a beach shower for rinsing off after a day in the sand. Each unit has its own extra ground floor storage locker, and the freshly painted, recently inspected building is centered on a lush tropical courtyard with a fountain, surrounded by beautifully landscaped grounds with paver parking. Condominium fees include water, sewer, trash, and basic cable. You are also just moments from everyday shopping and convenience at the Shoppes of Bay Isles, home to a Publix, CVS, and more, all without ever leaving the island, while St. Armands Circle and downtown Sarasota are an easy drive down the Key. With upgraded windows and doors, furnishings, appliances, and modern baths already in place, this is a Longboat Key retreat ready to enjoy from the very first day. Come experience it for yourself. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

3240 Gulf Of Mexico Drive Unit B504, Longboat Key

Easy access and docking at this 75 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina on D-dock. Located on the West side of the marina. Ample turning radius between piers, so lots of room to maneuver. Direct access to Sarasota Bay and the ICW; 15 minutes to the Gulf. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village and restaurants, shopping (close to Publix, CVS, and other shops), recreational and social activities, on-site maintenance and concierge services. Each slip includes wifi, water, pump out and metered electric, along with trash pick up and dockhands to assist. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 70 LOA, usable beam is 23 ft at the head of the slip. Each vessel must be approved by the Association's Board of Directors prior to entering the marina by submitting a current photo and boat specs.

2800 Harbourside Drive Unit D-16, Longboat Key

4 Beds ⋅ 6 Baths ⋅ A4699408 MLS

This spectacular waterfront pool home was just completed in 2026 and is built with uncompromising craftsmanship and every attention to detail. A West Indies-inspired residence in the coveted neighborhood of Emerald Harbor on Longboat Key, it offers expansive water views from every room of the wide canal and Harris Bayou, granting easy access to the intracoastal waterway and the Gulf of Mexico. Walls of glass open to covered porches with remote screens that allow for easy indoor-outdoor living. Features include an incredible chef's kitchen with high-end appliances and a totally separate prep kitchen; Of the 4 bedrooms, there are two primary suites, and all of them have their own stunning en-suites. Each one has access to a covered balcony and all have those stunning water views; A fire pit, private dock, outdoor shower and pool bath, plus deeded beach access complete the Longboat Key lifestyle. Every luxury amenity expected in a home of this caliber makes this a truly special offering.

711 Old Compass Road, Longboat Key

An easy access slip with the views to along with the superb amenity package, Slip B-16 at Longboat Key Club Moorings Marina provides one of the most desired locations as a Yacht Club Member slip in the Marina. With the slip measuring 85 x 29.5, and a usable beam of 25 feet and a long and extra wide finger pier. This 'inside the T-head' slip location provides close proximity to the Marina Village, Restaurant, and Pool. The Longboat Key Club Moorings Marina is a World Class deep water marina providing direct access to Sarasota Bay and ICW. Yacht Club membership at the Longboat Key Club Moorings provides members access to the private clubhouse, which is well appointed with TV, conference room, private pool area, outside seating and tables, grill, and bathhouse all in a relaxing atmosphere. Additionally, the Longboat Key Club offers multiple restaurants, world class tennis and golf facilities, fitness center, with spa and beach access. The Club also reciprocates with 400 of Clubs throughout the country. The Marina is also located within close proximity to Publix, CVS, and world class shopping at St. Armand's Circle. The longest vessel this slip will accommodate is 80 feet. Beam depends on the vessel type and measure. Vessel must be approved by the Board of Directors prior to entering the Marina. Membership in the Longboat Key Club is required.

2600 Harbourside Drive Unit B-16, Longboat Key

2 Beds ⋅ 2 Baths ⋅ A4699335 MLS ⋅ 2301 BLDG.

Simply magnificent! This beautifully renovated residence offers the perfect blend of sophisticated design, comfort, and effortless coastal living. Thoughtfully updated with designer finishes throughout, this move-in-ready home features an open, light-filled floor plan highlighted by floor-to-ceiling windows and a spectacular 38-foot covered terrace overlooking lush tropical gardens. Accessible from the living room and both bedrooms, the expansive terrace is the perfect place to enjoy your morning coffee, entertain guests, or relax with refreshing Gulf breezes. The updated kitchen flows seamlessly into the dining and living areas, creating an inviting space for everyday living and entertaining. Beautiful wood flooring, custom architectural details, stainless steel appliances, and abundant natural light add warmth and elegance throughout the home. The spacious primary suite serves as a private retreat with terrace access and a beautifully renovated ensuite bath featuring light wood cabinetry and granite countertops. The generous guest bedroom also opens to the terrace and includes a built-in Murphy bed, offering exceptional flexibility for visiting family and friends or a home office. Life at The Islander Club is truly resort-inspired. Residents enjoy over 400 feet of private Gulf-front beach, a heated beachfront swimming pool, a newly renovated state-of-the-art fitness center, two new sauna rooms, a Har-Tru® tennis court, two pickleball courts, a beautifully updated social room, library, secure key-fob entry, on-site management, and exceptional lock-and-leave convenience. Adding even greater value, The Islander Club has recently completed an extensive program of capital improvements, including exterior restoration and stucco repairs, balcony waterproofing, new roofs on both residential towers, clubhouse, and carports, modernized pool facilities with new tile, resurfacing, and equipment, refreshed landscaping and lighting, hurricane-rated windows and doors, and a completely renovated fitness center. These significant investments provide both peace of mind and long-term value for future owners. Whether you are searching for a full-time waterfront residence, a seasonal escape, or an exceptional investment opportunity, this beautifully updated condominium offers the very best of Longboat Key's coveted beachfront lifestyle.

2301 Gulf Of Mexico Drive Unit 44N, Longboat Key

2 Beds ⋅ 2 Baths ⋅ A4698596 MLS ⋅ Islander Club Of Longboat BLDG.

Experience exceptional Gulf-front living in this beautifully maintained two-bedroom, two-bath residence at the highly desirable Islander Club on Longboat Key. Enjoy peaceful views of the manicured grounds, entrance, and tennis courts from the expansive wraparound terrace offering more than 60 feet of private outdoor living space—perfect for relaxing or entertaining. Inside, the light-filled open floor plan features floor-to-ceiling sliding glass doors, a well-appointed kitchen with KitchenAid appliances, and spacious living and dining areas. The primary suite offers terrace access and an en-suite bath, while the guest bedroom provides comfortable accommodations for visitors or a home office. Recent updates include hurricane-impact windows and doors, a Bosch HVAC (2016), water heater (2020), in-unit humidistat, assigned parking, and extensive community improvements including new elevators, roof, porte cochère, fitness center, clubhouse, locker rooms with saunas, recreation room, and landscaping. End-window replacements have also been ordered. The Islander Club offers over 400 feet of private Gulf beach frontage, a heated beachfront pool, fitness center, Har-Tru tennis court, two pickleball courts, two fishing piers, on-site management, and 24/7 maintenance staff. Just minutes from St. Armands Circle and Downtown Sarasota, this is your opportunity to enjoy the very best of Longboat Key beachfront living.

2301 Gulf Of Mexico Drive Unit 45N, Longboat Key

2 Beds ⋅ 2 Baths ⋅ A4698081 MLS ⋅ D BLDG.

Welcome to Longboat Harbour D-204, a beautifully maintained second-floor condominium in one of Longboat Key's most desirable gated waterfront communities. Ideally located in Building D—the closest building to the community's private Gulf beach access—this residence offers umatched convenience to the beach pavilion, showers, restrooms, and private beach lockers. Inside, you'll find a bright and comfortable floor plan featuring granite countertops, an in-unit washer and dryer, a spacious bedroom with a new impact window, and electric blinds. Additional highlights include a private storage locker, covered carport parking space, proximity to the elevator, a new roof, and all assessments fully paid. Longboat Harbour offers resort-style amenities including four heated swimming pools, a fitness center with sauna, tennis and pickleball courts, art studios, a woodworking shop, and a yacht club with a protected harbor. Located just miles from St. Armands, Lido Beach, Downtown Sarasota, Anna Maria Island, Homes Beach, and Bradenton Beach, this is the perfect opportunity to enjoy the best of Longboat Key waterfront and beach living.

4340 Falmouth Drive Unit D-204, Longboat Key

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