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4976 Gulf Of Mexico Drive Unit Villa 18, Longboat Key
$600,000
3 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
Under contract-accepting backup offers. Virtually Staged. PRICE REDUCED! Experience the ultimate Longboat Key lifestyle in this waterfront gem featuring stunning Sarasota Bay and canal views. This spacious residence offers two Bedrooms, two Bathrooms, a versatile Bonus Room (ideal as a 3rd Bedroom, Home Office or private In-Law/Nanny Suite), plus a generous laundry room with newer full-size machines. This villa has been completely and meticulously renovated, with no detail overlooked and no expense spared. Beyond its stunning finishes, this home offers something incredibly valuable: Exceptional Peace of Mind! Major infrastructure updates include new electrical and plumbing systems, new Luxury Vinyl Plank flooring, fresh interior paint, and Hurricane-Impact Windows and Doors throughout. EVEN BETTER...exterior Building Maintenance Repairs and Insurance (including Flood, Hurricane, and Hazard coverage) are all included in the monthly HOA fee, creating a truly low-stress ownership experience. Recent updates include stylishly renovated bathrooms with stone countertops and new vanities, while the spacious new kitchen offers stainless appliances, quartz counters, plus abundant storage and counter space. This home also features a light-filled Florida room opening to a private patio, perfect for outdoor grilling, dining under the stars or watching playful manatees and dolphins in the canal. And for ultimate convenience, everyday living is effortless with the attached covered carport. Beyond your private retreat, Windward Bay offers resort-style amenities across 26 pristine, landscaped bay front acres. Enjoy two heated pools with complimentary lounge seating, saunas, tennis and pickleball courts, a fitness center, shuffleboard, boat slips ($50/month or $55/month with owner-provided lift), kayak/paddle board storage and launch ($45/year), fishing, and three private beach access points. Plus, Zota Beach Resort is just across the street for elegant dining and nightly sunsets. Windward Bay is a proactive, well-managed community that has passed its structural integrity inspection and is certified for another 10 years. Owners may rent up to twice per year with a one-month minimum, offering excellent income potential. Best of all—this rare Longboat Key community is pet-friendly for Owners and Renters! Don’t miss your chance to own a slice of island paradise and enjoy a relaxed, coastal lifestyle surrounded by natural beauty and first-class amenities. Your dream retreat awaits!

4976 Gulf Of Mexico Drive Unit Villa 18, Longboat Key
847 Evergreen Way, Longboat Key
$599,000
2 Beds ⋅ 3 Baths ⋅ Cedars East SubDv. ⋅ 34228 Zip Code
Refined Coastal Living with Proven Income Potential – Experience the best of Longboat Key in this impeccably appointed, turnkey furnished residence within the coveted Cedars East Tennis Resort. This elegant 2BR/2.5BA townhome spans 1,440 square feet of thoughtfully curated living space, where tasteful coastal design meets modern comfort. The gourmet kitchen is adorned with granite surfaces and flows seamlessly into a bright, open living area designed for effortless entertaining. A tranquil, private lanai invites you to unwind amid lush tropical surroundings. The primary suite serves as a serene retreat, complete with dual vanities and a spa-inspired ambiance, while upstairs laundry enhances everyday ease. With a strong history of rental performance, this property offers a rare opportunity to blend lifestyle with investment. Residents and guests enjoy an array of resort-caliber amenities, including championship Har-Tru tennis courts, a heated Olympic-style pool, fitness center, and exclusive bayfront features such as a kayak launch, fishing pier, and scenic mangrove boardwalks. An on-site dining option adds to the effortless luxury. Ideally located just moments from the beautiful beaches of Longboat Key, the boutiques and dining of St. Armands Circle, downtown Sarasota, and Anna Maria Island. A distinctive offering for the discerning buyer seeking both coastal elegance and exceptional return on investment. No flood damage | New A/C (2025)

847 Evergreen Way, Longboat Key
4540 Gulf Of Mexico Drive Unit 204, Longboat Key
$595,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
Under contract-accepting backup offers. Welcome to your island retreat, an impeccably renovated 2-bedroom, 2-bath residence offering the best of Longboat Key living with beautiful views of the preserved mangroves and Sarasota Bay. Renovated from top to bottom, this home has been thoughtfully transformed and is available TURNKEY FURNISHED with hurricane impact windows and shutters for a peace of mind. The BRAND-NEW KITCHEN showcases quartz countertops, custom cabinetry, and all-new stainless-steel appliances, opening seamlessly to the bright and airy living space. Both bathrooms have been completely updated with modern finishes and quartz countertops, creating a fresh, cohesive feel throughout the home. A Murphy bed in the office area adds even more versatility, providing the perfect setup for overnight guests while still allowing the space to function as a home office.Living at Windward Bay means embracing the Longboat Key lifestyle from both the BAY AND THE BEACH. Enjoy three beach access points directly across the street for effortless days along the Gulf, while boat slips available to residents make it easy to get out on Sarasota Bay and explore the surrounding waterways. Windward Bay is a PET-FRIENDLY, amenity-rich waterfront community offering multiple swimming pools, tennis and pickleball courts, a fitness center with sauna, kayak storage, and scenic walking paths along the bayfront. Ideally situated on Longboat Key, you are just minutes from exceptional restaurants and shopping, St. Armands Circle, Anna Maria Island, and everything Sarasota has to enjoy. With FULLY FUNDED RESERVES FOR 2026, NO UPCOMING SPECIAL ASSESSMENTS, and a PASSED MILESTONE INSPECTION, this move-in-ready residence offers the renovations, amenities, location, and peace of mind today's Florida condo buyer is looking for. Your Longboat Key lifestyle awaits!

4540 Gulf Of Mexico Drive Unit 204, Longboat Key
5841 Gulf Of Mexico Drive Unit 244, Longboat Key
$505,000
1 Beds ⋅ 1 Baths ⋅ Silver Sands SubDv. ⋅ 34228 Zip Code
REDUCE PRICE- RARE FIND!!! This fully furnished turnkey 1bedroom/1bath end unit has an open kitchen, dining and living room combo with a sofa sleeper and a screened lanai accommodating four guests comfortably. This lovely turnkey unit has a spectacular view of the Gulf of Mexico from the kitchen, living room and screened in lanai. Walk out of the lanai and dive into the heated pool with an outdoor grill or sink your feet into the sand and ease on into the gulf to experience a tranquil tropical get away in this perfectly situated condo that says paradise as far as the eyes can see. The interior was fully renovated in 2025 with new A/C, Hot Water Heater all new kitchen stainless steel appliances, cabinetry and furniture with the primary bedroom and built-in closet space. The unit is loaded with all the amenities you need. Around the corner of the unit is the laundry facility and a miniature golf course and shuffleboard for a little bit of relaxing fun. This unit is a Great owner/investment opportunity to generate income renting nightly, weekly and monthly. The owner has the option to manage the unit themselves, choose a management company of choice or use the management team on site. The Silver Sands Condo is a short drive from Anna Maria Island, St Armand Circle, and downtown Sarasota loaded with fine dining, entertainment, parks, clubs, marinas, endless shopping and all that the tropical environment offers. Longboat Key offers a tropical lifestyle defined by pristine beaches, world-class golf, and a relaxed atmosphere which is where you will find this one-of-a-kind unit. As mentioned, this type of unit is rarely on the market. Don't wait, now is the time to make this your piece of paradise!

5841 Gulf Of Mexico Drive Unit 244, Longboat Key
1945 Gulf Of Mexico Drive Unit M2-402, Longboat Key
$499,000
2 Beds ⋅ 2 Baths ⋅ Seaplace SubDv. ⋅ 34228 Zip Code
Under contract-accepting backup offers. Seaplace Condominiums, half mile Gulf of Mexico beachfront property with chaise lounges & umbrellas provided on private beach portion. Elegant turnkey-furnished unit with hurricane impact doors & windows. Next to clubhouse pool, gym, sauna & community kitchen. Two properties from St. Regis Resort restaurants & beach bar.

1945 Gulf Of Mexico Drive Unit M2-402, Longboat Key
1932 Harbourside Drive Unit 214, Longboat Key
$449,000
2 Beds ⋅ 2 Baths ⋅ Bay Isles SubDv. ⋅ 34228 Zip Code
Under contract-accepting backup offers. Direct Sarasota Bay views, a spacious waterfront terrace and private Bay Isles Beach Club access set this Fairway Bay residence on Longboat Key apart. The rare second-floor walk-down location offers its own stairs from the terrace to ground level—step outside for a walk without ever taking the elevator—while the due-east exposure provides beautiful sunrise views over Sarasota Bay with your morning coffee. Turnkey furnished and comfortable as-is, the 1,192-square-foot residence also offers the opportunity to personalize over time, along with a full-size washer and dryer, one under-building parking space and additional storage. Fairway Bay amenities include a waterfront clubhouse, heated pool and spa, fitness center and lush tropical surroundings, while the private Bay Isles Beach Club provides residents with Gulf of Mexico beach access. Ideally located near Longboat Key dining and recreation and just a short drive from the shopping, restaurants and cultural attractions of downtown Sarasota.

1932 Harbourside Drive Unit 214, Longboat Key
3710 Gulf Of Mexico Drive Unit D19, Longboat Key
$99,000
2 Beds ⋅ 1 Baths ⋅ Gulfshore Of Longboat Key SubDv. ⋅ 34228 Zip Code
FANTASTIC OPPORTUNITY to own a home in a beach-to-bay community. Gulfshore of Longboat Key has it all -- private, pristine sand beach, on the Gulf of Mexico, a marina (needs to be repaired) on Sarasota Bay, large community pool, clubhouse with a commercial kitchen, a well-maintained campus and very reasonable HOA fees. Truly, Gulfshore is a remnant of Old Florida that is just six miles from the world-famous St. Armand’s Circle. This home features a living room, separate kitchen, dining room and two bedrooms. This unit was significantly impacted by the two hurricanes in late September and early October 2024. This home will require a complete remodel. Thus, the price has been reduced to the value of the land. The marina is in the process of being rebuilt. This unit also has parking for two cars and an outside shower/bathroom (needs to be remodeled) that is perfect for when you return from the beach. Gulfshore does not permit rentals or pets. This home offers the perfect opportunity to live in paradise at a very affordable price and in a home that you designed.

3710 Gulf Of Mexico Drive Unit D19, Longboat Key
408 Gulf Of Mexico Drive Unit 1332, Longboat Key
$59,000
Boathouse On Longboat SubDv. ⋅ 34228 Zip Code
Under contract-accepting backup offers. Welcome to Slip #1332 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront locations. This premium slip accommodates boats up to 31.5 feet in length, with a maximum height of 8ft7in and a 9 ft beam (No T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and even the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage, it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key.

408 Gulf Of Mexico Drive Unit 1332, Longboat Key