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Second-home buyers and investment-minded buyers, take note. This beautifully furnished, turnkey residence at Cedars East on Longboat Key offers the rare combination of a polished coastal retreat, an established rental history, and meaningful upside potential. The home has generated approximately $50,000 in average annual rental payout revenue, after Airbnb and VRBO fees, providing a proven income history while maintaining the flexibility of up to 26 rental opportunities a year—an unusually flexible arrangement for Longboat Key. The owners have invested more than $130,000 in upgrades and improvements since 2021, creating a home that is not simply rental-ready, but thoughtfully maintained and continually enhanced. The current owners have created a home designed to deliver an exceptional guest experience. The sale includes the home's high-quality furnishings, top-of-the-line kitchenware—including All-Clad cookware—solid dishware, premium beach equipment and carefully selected décor. The result is reflected in the property's rental reputation, with more than 40, 5-Star Airbnb reviews from previous guests. Positioned near the front of Cedars East, the residence offers more convenient access to the Gulf beaches than many locations within the community and is next to the Longboat Key bike path. Inside, the 1,440-square-foot, two-bedroom, 2½-bath residence features an open living and dining area, a large garage, and a private, wooded outlook from the living room and lanai. The lush greenery creates a wonderfully private, almost treehouse-like setting—a peaceful contrast to the Gulf just moments away. Residents of Cedars East enjoy a resort-style setting with HOA amenities including the community pool, kayak and paddle board launch, fishing pier, cable, water, sewer, trash and pest control.Optional membership at the Cedars Tennis Resort & Club provides access to additional tennis, pickleball and fitness amenities. Whether you're looking for a beautifully finished Longboat Key retreat, a second home that can generate income, or a turnkey vacation property with an established rental history, this residence offers a compelling combination of lifestyle and flexibility. Come experience The Longboat Key Life.

2 Beds ⋅ 3 Baths ⋅ A4706129 MLS ⋅ Na BLDG.

Second-home buyers and investment-minded buyers, take note. This beautifully furnished, turnkey residence at Cedars East on Longboat Key offers the rare combination of a polished coastal retreat, an established rental history, and meaningful upside potential. The home has generated approximately $50,000 in average annual rental payout revenue, after Airbnb and VRBO fees, providing a proven income history while maintaining the flexibility of up to 26 rental opportunities a year—an unusually flexible arrangement for Longboat Key. The owners have invested more than $130,000 in upgrades and improvements since 2021, creating a home that is not simply rental-ready, but thoughtfully maintained and continually enhanced. The current owners have created a home designed to deliver an exceptional guest experience. The sale includes the home's high-quality furnishings, top-of-the-line kitchenware—including All-Clad cookware—solid dishware, premium beach equipment and carefully selected décor. The result is reflected in the property's rental reputation, with more than 40, 5-Star Airbnb reviews from previous guests. Positioned near the front of Cedars East, the residence offers more convenient access to the Gulf beaches than many locations within the community and is next to the Longboat Key bike path. Inside, the 1,440-square-foot, two-bedroom, 2½-bath residence features an open living and dining area, a large garage, and a private, wooded outlook from the living room and lanai. The lush greenery creates a wonderfully private, almost treehouse-like setting—a peaceful contrast to the Gulf just moments away. Residents of Cedars East enjoy a resort-style setting with HOA amenities including the community pool, kayak and paddle board launch, fishing pier, cable, water, sewer, trash and pest control.Optional membership at the Cedars Tennis Resort & Club provides access to additional tennis, pickleball and fitness amenities. Whether you're looking for a beautifully finished Longboat Key retreat, a second home that can generate income, or a turnkey vacation property with an established rental history, this residence offers a compelling combination of lifestyle and flexibility. Come experience The Longboat Key Life.

539 Forest Way Unit 539, Longboat Key

$559,900

NEW AND IMPROVED PRICE! There is a certain ease to life on Longboat Key, where mornings can begin with a walk to the beach, afternoons unfold by the pool or on the tennis court, and dinner beside the water is never far from home. Set within Cedars East at Cedars Tennis Resort & Club, this beautifully maintained three-level townhome offers a refined way to experience one of Florida’s most desirable barrier-island lifestyles. Natural light is one of the first things you notice. An abundance of windows fills the home with sunshine, creating a bright, calm, and serene atmosphere that feels perfectly suited to its coastal surroundings. New luxury vinyl plank flooring extends through the entry and main living level, giving the home a fresh, cohesive look, while carpeting along the staircase and throughout the third-floor bedroom level adds warmth and comfort to the private spaces. The second floor brings the kitchen, dining, and living areas together in an easy, welcoming flow designed for relaxed everyday living and effortless entertaining. Just beyond the living room, the screened balcony creates a peaceful outdoor retreat for morning coffee, casual dining, quiet reading, or unwinding at the end of the day. A convenient half bath completes this level. Upstairs, the primary suite offers a private ensuite bath with dual sinks and a comfortable sense of separation from the main living areas. The second bedroom features a walk-in closet and is positioned near the full guest bath and upstairs laundry closet. The washer and dryer are approximately three months old and are included with the home. Thoughtful improvements add both style and confidence, including a roof replaced in 2024, a 2024 HVAC system serviced in April 2026, updated interior paint, refreshed flooring, newer toilets, faucets, light fixtures and vents, and a new garage door. Garage parking adds welcome convenience along with room for bicycles, beach equipment, and additional storage. Life at Cedars Tennis Resort & Club is centered around the outdoors and the relaxed sophistication of Longboat Key. Enjoy tennis and pickleball, spend the afternoon by the heated community pool, stay active in the fitness facilities, or gather for a meal without leaving the neighborhood. Nearby beach access makes Gulf days easy to enjoy, while waterfront restaurants, island cafés, marinas, biking routes, and the natural beauty of Longboat Key are all close at hand. For buyers considering investment potential, the property has a strong short-term rental history and is already heavily booked from December through June 2027, offering the advantage of established demand and reservations already in place. All rentals remain subject to current association rules, approval requirements, and the terms of existing reservations. From fresh seafood and sunset dinners to quiet mornings near the shore, this location places the best of Longboat Key within easy reach. St. Armands Circle, Anna Maria Island, and the cultural attractions of Sarasota are also nearby, allowing you to enjoy the island’s peaceful atmosphere without feeling removed from everything the area has to offer. Whether envisioned as a full-time residence, seasonal retreat, or income-producing coastal getaway, this is an opportunity to enjoy thoughtful updates, abundant natural light, resort-inspired amenities, garage parking, and the unmistakable lifestyle of Longboat Key. ¤ Please see 3D Tour and Video ¤

2 Beds ⋅ 3 Baths ⋅ N6144572 MLS ⋅ 508 BLDG.

NEW AND IMPROVED PRICE! There is a certain ease to life on Longboat Key, where mornings can begin with a walk to the beach, afternoons unfold by the pool or on the tennis court, and dinner beside the water is never far from home. Set within Cedars East at Cedars Tennis Resort & Club, this beautifully maintained three-level townhome offers a refined way to experience one of Florida’s most desirable barrier-island lifestyles. Natural light is one of the first things you notice. An abundance of windows fills the home with sunshine, creating a bright, calm, and serene atmosphere that feels perfectly suited to its coastal surroundings. New luxury vinyl plank flooring extends through the entry and main living level, giving the home a fresh, cohesive look, while carpeting along the staircase and throughout the third-floor bedroom level adds warmth and comfort to the private spaces. The second floor brings the kitchen, dining, and living areas together in an easy, welcoming flow designed for relaxed everyday living and effortless entertaining. Just beyond the living room, the screened balcony creates a peaceful outdoor retreat for morning coffee, casual dining, quiet reading, or unwinding at the end of the day. A convenient half bath completes this level. Upstairs, the primary suite offers a private ensuite bath with dual sinks and a comfortable sense of separation from the main living areas. The second bedroom features a walk-in closet and is positioned near the full guest bath and upstairs laundry closet. The washer and dryer are approximately three months old and are included with the home. Thoughtful improvements add both style and confidence, including a roof replaced in 2024, a 2024 HVAC system serviced in April 2026, updated interior paint, refreshed flooring, newer toilets, faucets, light fixtures and vents, and a new garage door. Garage parking adds welcome convenience along with room for bicycles, beach equipment, and additional storage. Life at Cedars Tennis Resort & Club is centered around the outdoors and the relaxed sophistication of Longboat Key. Enjoy tennis and pickleball, spend the afternoon by the heated community pool, stay active in the fitness facilities, or gather for a meal without leaving the neighborhood. Nearby beach access makes Gulf days easy to enjoy, while waterfront restaurants, island cafés, marinas, biking routes, and the natural beauty of Longboat Key are all close at hand. For buyers considering investment potential, the property has a strong short-term rental history and is already heavily booked from December through June 2027, offering the advantage of established demand and reservations already in place. All rentals remain subject to current association rules, approval requirements, and the terms of existing reservations. From fresh seafood and sunset dinners to quiet mornings near the shore, this location places the best of Longboat Key within easy reach. St. Armands Circle, Anna Maria Island, and the cultural attractions of Sarasota are also nearby, allowing you to enjoy the island’s peaceful atmosphere without feeling removed from everything the area has to offer. Whether envisioned as a full-time residence, seasonal retreat, or income-producing coastal getaway, this is an opportunity to enjoy thoughtful updates, abundant natural light, resort-inspired amenities, garage parking, and the unmistakable lifestyle of Longboat Key. ¤ Please see 3D Tour and Video ¤

508 Forest Way, Longboat Key

$875,000

Good bones; original finishes. This home in the Cedars East Tennis Resort condominium community offers a solid foundation, great location, views of the Sarasota Bay, two-week rental opportunities, and much more. Twice the size of most units in Cedars, this feels like a single-family home in an active condo community. Being sold as-is, the home features 2813 sq ft of living space, a 2024 roof, hardwood floors on the first living level, 2 screen lanais (one on each floor) with one overlooking the mangroves for views of sunset-painted skies, garage spaces for 2 cars, wood-burning fireplace, and there’s a flex room (think den, office, guest room, artist studio, music room, etc.) adjoining the kitchen and a half-bath for guests. Walk-in closets on every floor are stacked to accommodate installing an elevator. Upstairs you will find 3 bedrooms and 2 full baths. The oversized primary bedroom features stunning views, an ensuite, two walk-in closets plus an extra built-in closet, and the 2nd screened lanai. Amenities include exceptional access to bay waters for kayaking or fishing, a boardwalk through mangroves between this home and the pool, and a private bayside dock (no boat access) for sunrise views. Pool membership comes with home ownership. Tennis, pickleball and fitness center access is available through Cedars East Resort at an annual rate plus a membership-based restaurant and poolside TIKI bar. Update, redesign and make it your home or income opportunity today!

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

Good bones; original finishes. This home in the Cedars East Tennis Resort condominium community offers a solid foundation, great location, views of the Sarasota Bay, two-week rental opportunities, and much more. Twice the size of most units in Cedars, this feels like a single-family home in an active condo community. Being sold as-is, the home features 2813 sq ft of living space, a 2024 roof, hardwood floors on the first living level, 2 screen lanais (one on each floor) with one overlooking the mangroves for views of sunset-painted skies, garage spaces for 2 cars, wood-burning fireplace, and there’s a flex room (think den, office, guest room, artist studio, music room, etc.) adjoining the kitchen and a half-bath for guests. Walk-in closets on every floor are stacked to accommodate installing an elevator. Upstairs you will find 3 bedrooms and 2 full baths. The oversized primary bedroom features stunning views, an ensuite, two walk-in closets plus an extra built-in closet, and the 2nd screened lanai. Amenities include exceptional access to bay waters for kayaking or fishing, a boardwalk through mangroves between this home and the pool, and a private bayside dock (no boat access) for sunrise views. Pool membership comes with home ownership. Tennis, pickleball and fitness center access is available through Cedars East Resort at an annual rate plus a membership-based restaurant and poolside TIKI bar. Update, redesign and make it your home or income opportunity today!

836 Evergreen Way, Longboat Key

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