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1485 Gulf Of Mexico Drive Unit 303, Longboat Key
$1,395,000
2 Beds ⋅ 3 Baths ⋅ Players Club SubDv. ⋅ 34228 Zip Code
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
5260 Gulf Of Mexico Drive Unit 403, Longboat Key
$649,999
2 Beds ⋅ 2 Baths ⋅ Banyan Bay SubDv. ⋅ 34228 Zip Code
This beautifully maintained, ground-floor 2-bedroom, 2-bathroom condo in the desirable Banyan Bay Club offers an exceptional opportunity to own a spacious, modern / updated, move-in-ready home perfectly positioned in a charming, pet-friendly gulf-to-bay community. This unit combines convenience, amenities, and a relaxed coastal lifestyle—all at an outstanding location. This Banyan Bay condominium has an open floor plan with plank style ceramic tile throughout, recently updated featuring new cabinets, vanities, quartzite/quartz countertops and new stainless steel appliances; new Central Air system, and new hot water heater, in-unit full-size washer & dryer, modern tile design in bath, extra sleeping nook for added flexibility, tastefully furnished (can be sold furnished), private patio nestled under a majestic banyan tree-ideal for morning coffee or evening cocktails, large glass hurricane sliders & windows offering a garden view, fiber optic internet included for each unit. SQUARE FOOTAGE IN SLEEPING NOOK IS ADDED TO MAKE THE INTERIOR SQ FTG 1163. The resort-Style Community Amenities (steps from your door): heated community swimming pool, newly resurfaced tennis and pickleball court, fully equipped fitness center, clubhouse with social hall and full kitchen, new day dock, fishing pier, kayak/paddleboard launch, & storage, private gulf beach access with complimentary lounge chairs on the sand, assigned covered carport parking plus ample guest parking, exterior storage for beach gear, on-site manager and carefree exterior maintenance handled by the association, bicycle storage and mature tropical landscaping with giant banyan trees. Unbeatable Location-why Mid-Key is Best! Everything you need is within walking distance; numerous restaurants & cafes, boutiques, beautiful Durante Park with shaded trails and playground, 3 minute walk to your private Gulf beach, 1-minute walk to the community pool, gym, clubhouse, and courts,. This 44-unit condominium offers a social atmosphere, plenty of activities, up to 2 pets allowed (no weight or size limit). Whether you are seeking a full-time residence, vacation getaway, second home or investment property (valued returning renter’s incomes can offset HOA fees), this immaculate condo is ready for you to move in and start enjoying the island lifestyle today. Don't miss this combination of location, amenities and value on Longboat Key!

5260 Gulf Of Mexico Drive Unit 403, Longboat Key
836 Evergreen Way, Longboat Key
$875,000
3 Beds ⋅ 3 Baths ⋅ Cedars East SubDv. ⋅ 34228 Zip Code
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
5270 Gulf Of Mexico Drive Unit 508, Longboat Key
$754,900
3 Beds ⋅ 3 Baths ⋅ The Banyan Bay Club SubDv. ⋅ 34228 Zip Code
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
4500 Gulf Of Mexico Drive Unit 206, Longboat Key
$769,000
2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code
"One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!” This residence is now available for public and private showings. 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
1115 Gulf Of Mexico Drive Unit 401, Longboat Key
$875,000
2 Beds ⋅ 2 Baths ⋅ Beachplace SubDv. ⋅ 34228 Zip Code
The perfect beach getaway or investment property, look no further. With stunning water views from all new windows and doors, beach access, and appealing lease policy, this 1,172 square-foot 2 bedroom, 2 bath residence in Beachplace is ready to enjoy! Watch stunning sunset views from your southwestern facing, L shaped balcony overlooking beautiful well-manicured lawn, pond, and enchanting Gulf of Mexico waters. This views can also be enjoyed while in the master bedroom. The condo residence is a corner unit, located on the 4th floor with ideal proximity to the building elevator and has wood-look tile throughout. Beachplace is perfectly located on the south end of Longboat Key, minutes from St. Armands, downtown Sarasota, SRQ Airport and much, much more. Community offers on-site management, 24-hour security, a Jr. Olympic-sized swimming pool, and newly designed hot tub area. There are lighted tennis courts, a fitness center and gas grills for the community use.

1115 Gulf Of Mexico Drive Unit 401, Longboat Key
4380 Exeter Drive Unit H202, Longboat Key
$480,000
2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code
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
1065 Gulf Of Mexico Drive Unit 201, Longboat Key
$599,000
2 Beds ⋅ 2 Baths ⋅ Beachplace SubDv. ⋅ 34228 Zip Code
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
230 Sands Point Road Unit 3205, Longboat Key
$996,000
1 Beds ⋅ 1 Baths ⋅ Inn On The Beach SubDv. ⋅ 34228 Zip Code
Spectacular Gulf and Sunset views are enjoyed from this west facing Junior Suite in Building 3. The direct beach view through the swaying palms perfectly encompasses the resort lifestyle and the vision guests have of tropical landscapes when making reservations. This completely renovated residence is currently in the hotel program and reported healthy income in 2023 and 2024. As an owner, you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship Golf, the award-winning Tennis Gardens, Spa/Wellness Center, white sand beach with umbrellas and waitstaff and a full service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start your Longboat Life today!

230 Sands Point Road Unit 3205, Longboat Key
3806 Gulf Of Mexico Drive Unit C208, Longboat Key
$295,000
1 Beds ⋅ 1 Baths ⋅ Beach Harbor Club SubDv. ⋅ 34228 Zip Code
Discover coastal living at its finest with this charming condominium located on Gulf of Mexico Dr, Longboat Key. This residence offers stunning ocean views and easy access to beautiful beaches. The open-concept layout features modern finishes, a spacious living area, and a well-appointed kitchen. Enjoy relaxing on the private balcony overlooking the serene surroundings. The community amenities include a swimming pool, fitness center, and convenient access to local dining and shopping.

3806 Gulf Of Mexico Drive Unit C208, Longboat Key
1065 Gulf Of Mexico Drive Unit 402, Longboat Key
$799,000
2 Beds ⋅ 2 Baths ⋅ Beachplace SubDv. ⋅ 34228 Zip Code
This stunning 2 bed/2 bath residence comes turnkey furnished offering a full view of the Longboat Key Islandside Golf Course and partial views of the Gulf, Sarasota Bay, and the Sarasota city skyline through Hurricane Impact Sliders installed in 2024. The kitchen has been opened up to the living/dining area providing a beautiful view over the golf course greens while owners are creating culinary delights in the kitchen. There is a breakfast bar, a laundry closet, pantry, and plenty of solid wood cabinet space for storage. The primary suite pampers owners with access to the southeast-facing terrace along with a spacious primary bath offering dual vanities, an updated tile shower, and abundant closet space. The split floor plan allows for maximum privacy for both the primary and the ensuite guest bedroom. Other highlights include ceramic tile flooring throughout, stone counters, a coveted underbuilding parking space and an excellent rental policy of 1 month minimum 12 X per year. Beachplace offers a 24-hour manned guard gate, heated swimming pool & spa, tennis courts, dedicated pickleball courts, fitness center, clubhouse, on-site management, and miles of pristine beach to relax, enjoy and explore. Conveniently located on the south end of Longboat Key just minutes from the fine dining and shopping on St. Armands Circle and a short drive over the bridge to the cultural hub of downtown Sarasota.

1065 Gulf Of Mexico Drive Unit 402, Longboat Key
1591 Gulf Of Mexico Drive Unit 216, Longboat Key
$2,750,000
1 Beds ⋅ 2 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code
Incredible value at St. Regis Longboat Key. The last two one bedroom residences sold for $2,970,000 and $2,975,000. Step inside this spacious residence to discover a clean, modern interior with a sophisticated Palm Beach vibe. Designed for both style and comfort, this home features a gracious great room featuring floor-to-ceiling windows that flood the interiors with natural light and open to the large, 765 square foot private terrace with a built-in gas grill—perfect for gardening, entertaining friends and family, or relaxing outdoors. The chef’s kitchen is outfitted with Poggenpohl cabinetry, Wolf appliances, a Sub-Zero refrigerator, and Sub-Zero wine and beverage refrigerator, blending elegance with functionality. The owner’s suite also boasts floor-to-ceiling windows, a custom designed closet, and a luxurious bathroom with a frameless walk-in shower, Toto mechanized commode, and double vanities. With generous square footage and a thoughtful layout, this residence easily accommodates overnight guests while maintaining a sense of privacy. Additional features include electronic blinds throughout, adding both convenience and sophistication. Designer light fixtures add an elegant touch throughout the home. St. Regis Longboat Key offers a distinguished array of amenities meticulously curated for its residents. The Private Resident’s Clubhouse offers an environment of exclusivity, complemented by a state-of-the-art fitness center, as well as a pool and spa area reserved solely for residential use. Residents are granted privileged access to the legendary St. Regis Butler and Concierge services, which exemplify world-class hospitality and attention to detail. An extraordinary oceanfront spa awaits, alongside diverse dining experiences that showcase the highest standards of culinary excellence. Personal cabanas along the shore create private retreats for relaxation, while the family-friendly amenities include a meandering lazy river and a unique saltwater lagoon. This lagoon is home to a vibrant array of tropical fish species, graceful stingrays, and the resort’s resident tortoises, offering a captivating wildlife experience within the lush grounds. Spanning seventeen acres of beachfront on the coveted Longboat Key barrier island, this private oasis is conveniently located only 3.5 miles from St. Armand’s Circle, the region’s premier destination for shopping and dining. Whether seeking tranquil solitude or an active social environment, every aspect of life at St. Regis Longboat Key has been thoughtfully designed to anticipate and fulfill the desires of its residents. This offering represents more than just a residence; it is an invitation to embrace the legendary St. Regis lifestyle, defined by elegance, comfort, and outstanding service. Begin your journey to extraordinary Gulf side living.

1591 Gulf Of Mexico Drive Unit 216, Longboat Key
240 Sands Point Road Unit 4102, Longboat Key
$939,000
1 Beds ⋅ 1 Baths ⋅ Inn On The Beach SubDv. ⋅ 34228 Zip Code
Highly desirable 1st floor walkdown Junior Suite with Gulf views in Building 4 priced to sell. This completely renovated unit is currently in the hotel program and reported more income through August 2026 than all of 2025. There is an expanded deck in addition to the covered terrace, which provides direct access to the beach. Building 4 is situated farthest north on the gulf side where owners value privacy from the pool activities, but are still close to all of the amenities. As an owner, you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship golf, the award-winning Tennis Gardens, spa/wellness center, white sand beach with umbrellas and waitstaff and a full-service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start enjoying the Longboat Life today!

240 Sands Point Road Unit 4102, Longboat Key
1926 Harbourside Drive Unit 1302, Longboat Key
$769,000
2 Beds ⋅ 3 Baths ⋅ Fairway Bay 1 SubDv. ⋅ 34228 Zip Code
GATED, DEEDED PRIVATE BEACH ACCESS! This is a rare thing to be found on the keys! The main level with plantation shutters and hardwood floors includes the kitchen, dining and living areas. The kitchen has Subzero and Jenn-Air built in stainless steel appliances and granite countertops. A large second story skylight shines natural light through open ceilings onto the main floor dining area. The living area includes a fireplace and provides access to the back screened in lanai. Split bedrooms can be found on the 3rd level of the home. Both bedrooms have ensuite bathrooms and walk in closets. The owners ensuite bathroom includes dual sinks and a shower skylight. A heated pool is only steps away. Take advantage of the gym in the main clubhouse as well as the many amenities offered, including tennis. Membership to the Longboat Key Club is available for the ultimate Longboat Key lifestyle.

1926 Harbourside Drive Unit 1302, Longboat Key
1561 Gulf Of Mexico Drive Unit 403, Longboat Key
$12,750,000
3 Beds ⋅ 4 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code
St. Regis

1561 Gulf Of Mexico Drive Unit 403, Longboat Key
1591 Gulf Of Mexico Drive Unit 413, Longboat Key
$4,399,000
2 Beds ⋅ 3 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code
St. Regis

1591 Gulf Of Mexico Drive Unit 413, Longboat Key

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