Refine Search
Sort by
6951 Gulf Of Mexico Drive Unit 14, Longboat Key
$840,000
2 Beds ⋅ 2 Baths ⋅ Sea Pines Condominium SubDv. ⋅ 34228 Zip Code
WOW! The minute you open the front door of this first floor Coastal Retreat Seaside condo, you will be captivated by the shimmering, turquoise Gulf of Mexico Water View and the Panoramic Sandy White Beach in front of you. You'll be eager to get a closer look from the glassed in Florida Room, so you may overlook the beauty of this updated, attractively furnished & decorated first floor residence at Sea Pines, a small 28 unit beach front condo complex on the north end of Longboat Key, Florida. Since purchasing five years ago, these owners have lovingly transformed this almost 1400 square foot, corner unit with extra windows, open concept, two bedroom with En Suite baths & walk in closets to today's coastal contemporary style tastes. Improvements include light oak color Luxury Vinyl wide plank flooring throughout, Samsung stainless steel appliances including washer & dryer, new HVAC installed, updated the primary bedroom with a quartz counter vanity, tiled & glass door shower, and fitted out closet. The condo's interior was painted as well & new, high quality neutral colored living room, dining & bedroom furniture, rugs, lighting & drapery, artwork and a large entertainment center installed. A new tiled roof was installed on this building in 2024. Additional features include impact resistant windows in both bedrooms & the office adjacent to the kitchen. Plantation shutters cover all these windows. This office area is fitted out with oak cabinetry, desk & drawers, perfect for working at home. The spacious 26-foot-long lanai (Florida Room) can be entered from either the primary bedroom or the living room via sliders. This may be your favorite room with mesmerizing Gulf & beach views over the sea grass pathways to the water. And of course, the magnificent Longboat Key Gulf of Mexico sunsets will thrill you whether watching from your lanai or enjoying on the beach while toasting your good fortune! This turnkey handsomely appointed & attractively furnished seaside retreat offers great rental income if you so wish. Currently these owners are using RVA Rentals, but a new owner can choose how or if to lease out this unit. Rental friendly Sea Pines can be leased out six times a year with a one month minimum time period. Two additional benefits to this first floor Unit 14 are that these owners have paid $5357 assessment for new landscaping for the complex plus new interior glass sliders will be installed in the living room & primary bedroom and sellers have paid for that as well. Sea Pines has an electronic gated entry for security & privacy. Amenities include a large, heated pool, is large pet friendly & offers excellent rental income possibilities. Charming Longboat Village is nearby with fabulous restaurants like The Shore, Mar Vista, Whitney's, Ventura's & the thriving Whitney Shopping Center. Anna Maria Island is just across the Longboat north end bridge for additional night life entertainment.

6951 Gulf Of Mexico Drive Unit 14, Longboat Key

1975 Gulf Of Mexico Drive Unit G4-307, Longboat Key
$830,000
2 Beds ⋅ 2 Baths ⋅ Seaplace SubDv. ⋅ 34228 Zip Code
Direct Gulf views take center stage at Seaplace G4-307. This spacious 2-bedroom, 2-bath residence with 1,257 square feet offers a wonderful opportunity to enjoy the beachfront lifestyle on Longboat Key, with beautiful, unobstructed views across the tropical grounds to the Gulf of Mexico. Step inside and your eyes are immediately drawn to the water. The open living and dining areas lead to the screened Gulf-view lanai, creating the perfect setting for morning coffee, afternoon sea breezes or simply relaxing while overlooking swaying palms, manicured grounds, the sandy beach and turquoise Gulf beyond. The kitchen features abundant white cabinetry, generous counter space, stainless-steel appliances and a convenient pass-through to the dining area. The spacious primary suite offers plenty of room for a king-size bed, excellent storage and an en-suite bath. The guest bedroom is comfortably sized with two beds and enjoys its own beautiful Gulf view, making it an inviting retreat for family and friends. With direct Gulf views from the living area, guest bedroom and screened lanai, the connection to the water is one of the defining features of this residence. Located within the gated, Gulf-front Seaplace community, residents enjoy direct beach access along with an impressive collection of resort-style amenities, all surrounded by beautifully maintained tropical landscaping. The south Longboat Key location places you just minutes from the shopping and dining of St. Armands Circle and the cultural attractions of downtown Sarasota. Furnishings are available separately by Bill of Sale, offering buyers the option for an easy transition to their Longboat Key getaway. Whether you're looking for a full-time residence, seasonal retreat or your own place by the beach, G4-307 delivers what Longboat Key living is all about—direct Gulf views, tropical surroundings and the beach just steps away.

1975 Gulf Of Mexico Drive Unit G4-307, Longboat Key

579 Bayview Drive, Longboat Key
$830,000
Bayview Estates SubDv. ⋅ 34228 Zip Code
Discover an extraordinary opportunity to build your dream waterfront retreat in the coveted Bayview Estates on world-famous Longboat Key. This exceptional saltwater canal lot offers direct access to the Intracoastal Waterway, Sarasota Bay, and the Gulf of Mexico—an absolute haven for boating enthusiasts. With a deep-water canal, dock, seawall, and lift already in place, the groundwork is set for effortless waterfront living and limitless design potential. The property features charming peekaboo bay views, with the opportunity to capture even more breathtaking vistas of Bishops Bayou and beyond through thoughtful elevation and architectural design. Imagine mornings greeted by peaceful sunrises, leisurely walks to the nearby beach just steps away, and unforgettable sunset views each evening. One of Longboat Key’s best surf breaks and public beach access are only moments from your door. All utilities are in place, making this an ideal canvas for new construction. Enjoy the quintessential island lifestyle with close proximity to fine dining, boutique shopping, tennis clubs, fitness centers, and beautiful community parks. This is a rare chance to own a prime piece of land in one of Longboat Key’s most desirable neighborhoods and bring your vision of luxury waterfront living to life. Schedule your private tour today and experience the possibilities firsthand.

579 Bayview Drive, Longboat Key

7105 Gulf Of Mexico Drive Unit 21, Longboat Key
$825,000
2 Beds ⋅ 2 Baths ⋅ Long Beach SubDv. ⋅ 34228 Zip Code
Gulfside Condo on north Longboat Key with direct beach access: This 2-bedroom, with bonus room, second floor condo offers the island lifestyle you've been searching for—a waterfront community, stunning sunset views from the lanai, and steps to the beach. Located in Longbeach Condo community on Longboat Key, this turnkey furnished, coastal Florida condo features 2 bedrooms, 2 bathrooms,and a bonus room currently used as a den. The comfortable floorplan features a bonus room for bunks, an office, or a reading room, a wide galley kitchen with Corian counters and tossed marble tile backsplash, in-unit washer/dryer, tile floors throughout, and a private balcony with views of the Gulf. At 19.5 foot base flood elevation, this unit was well above the storm surge of previous hurricanes. Longboat Key Living means beach access, world-class golf courses, world class tennis and waterfront dining just minutes away. The Longbeach Condo community offers 9.2 acres of gulf front, beach property, amenities like heated pool, club house, open parking, private beach access, kayak storage and private tennis. You're 15 minutes to St. Armands Circle shopping, 20 minutes to downtown Sarasota, and close to world-class fishing charters from Cortez Fishing Village. This barrier island property is perfect for full-time Florida living, a vacation home, a snowbird retreat or investment rental property. Rental history/projections available. The location puts you near Coquina Beach, Marina Jack, and easy access to Sarasota-Bradenton International Airport. Nationally ranked medical facilities located within minutes and all LBK first responders are EMTs! Exterior stairs to this unit are being replaced in June, scheduled for the two weeks beginning June 21 and ending July 2 weather allowing.

7105 Gulf Of Mexico Drive Unit 21, Longboat Key

2301 Gulf Of Mexico Drive Unit 36N, Longboat Key
$825,000
2 Beds ⋅ 2 Baths ⋅ Islander Club Of Longboat SubDv. ⋅ 34228 Zip Code
One or more photo(s) has been virtually staged. Front-row Gulf views and beachfront living set this 2BR/2BA residence apart at the Islander Club of Longboat Key. With over 1,235 sq. ft. of light-filled space set just above the sand, savor sweeping vistas of the shoreline and SPECTACULAR SUNSETS over the Gulf. White tile floors and neutral tones throughout create a sense of openness that draws focus to the stunning natural surroundings. A wall of glass sliders in the living room opens to the expansive terrace, where salty breezes and soft waves make every day feel like a vacation. The terrace spans the full width of the residence and can be accessed from both bedrooms, blending indoor and outdoor living in perfect balance. It’s a space with strong potential to match the lifestyle it serves. The primary suite is bathed in natural light, with floor-to-ceiling windows, a walk-in closet and a private bath with a separate water closet. The guest bedroom is equally inviting, with generous space and direct Gulf views. Islander Club is a highly desirable Gulf-front community offering resort-style amenities, including a beachfront pool, tennis courts, a fitness center, library, and billiards room, along with a secure, gated entrance. Conveniently located in the heart of Longboat Key, you're just minutes from St. Armands Circle, downtown Sarasota, and everything the area has to offer. Additionally, while membership to the Longboat Key Club is not required, it is available for residents seeking enhanced amenities. The club offers Restaurants, lounges, beach & poolside facilities, spa, fitness center, tennis courts, and access to 45 holes of championship golf.

2301 Gulf Of Mexico Drive Unit 36N, Longboat Key

2295 Gulf Of Mexico Drive Unit 115S, Longboat Key
$820,000
2 Beds ⋅ 2 Baths ⋅ Islander Club Of Longboat SubDv. ⋅ 34228 Zip Code
Wonderful "Manhattan Style" beachfront Condo with sweeping views of Sarasota Bay and views of the Gulf now available at the popular Islander Club on LBK. This gorgeous beachfront renovation was completed 4 years ago and truly shows all the craftmanship that went into the process under the owner's direction. Open kitchen beings the morning light into the room for enjoying your coffee or tea as you gaze across the sparking blue waters of the bay. Large 38ft balcony also has views of bay and a bit of the Gulf of Mexico. The Primary suite is a comfortable 13X20 which accesses the balcony and has a large walk-in closet. It is light and bright and a restful haven away from the main living area. The Islander club has recently renovated their clubhouse. The gym overlooks the gulf and the pool. There is a conference room, library, and an Olympic size heated pool, not to mention their Har-Tru tennis courts. The Location is very convenient. The shops of Bay Isles with the Publix and CVS are just a couple of minutes away. It's only 10 minutes to World renown St Armand Circle. Make this your permanent home or your week-end getaway. Secured Building . At The Islander Club "Everyday is a Holiday and Life is an endless vacation.

2295 Gulf Of Mexico Drive Unit 115S, Longboat Key

1904 Harbourside Drive Unit 201, Longboat Key
$815,000
3 Beds ⋅ 3 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code
Nestled within Bay Isles, one of Longboat Key’s most notable communities, this beautifully updated townhome is tucked among mature trees and lush foliage in the Fairway Bay enclave. This 3-bedroom, 3-bath residence offers 2,135 square feet of stylish living primarily across the two main levels. A thoughtfully selected color palette and professional design give the home an ensured elevated feel, presenting as a true showcase residence. The main living space features a reimagined, open chef-inspired kitchen designed for entertaining, complete with high-end appliances, ample prep space, and seamless connection to the living and dining areas. Soaring ceilings in the adjacent living room enhance the sense of openness, creating an inviting environment equally suited for everyday living and entertaining. The home is thoughtfully arranged across three levels. The ground level includes a two-car garage, storage, and a generously sized area behind the garage, offering flexible bonus space. The main floor (second level) features the primary living areas, two bedrooms (one currently used as a den), two guest baths, and a laundry room. The top floor (third level) is devoted to a loft TV room and the primary suite, flanked by two terraces. The atrium-style primary bath features a soaking tub and spa shower with steam and is splashed with natural light. One of the most coveted features is deeded private beach access, located less than half a mile from the property. Residents of Fairway Bay enjoy an amenity package that includes a 24-hour guard gate, clubhouse, fitness center, two heated pools and a spa, tennis and pickleball courts, barbecue areas, and scenic walking trails. Ownership includes exclusive membership to the Bay Isles Beach Club, a private Gulf-front retreat with a pristine beach, picnic areas, Tiki huts, grills, and updated facilities. Optional membership to the Longboat Key Club further enhances the lifestyle with access to championship golf, Har-Tru tennis courts, fine dining, a private beach club, spa services, a fitness center, and a vibrant social calendar. Everyday conveniences are right around the corner including Publix, CVS, dry cleaning, and more. This residence represents a rare offering that combines thoughtful design, resort-style amenities, and private beach access, all within one of Longboat Key’s premier gated communities.

1904 Harbourside Drive Unit 201, Longboat Key

7115 Gulf Of Mexico Drive Unit 23, Longboat Key
$800,000
2 Beds ⋅ 2 Baths ⋅ Long Beach SubDv. ⋅ 34228 Zip Code
Never miss another beach day or a green flash sunset in this rarely available 2 bed 2 bath home in the Longbeach Community- a GULF FRONT enclave on the tip of Longboat Key. A short walk to the beach, thoughtfully remodeled and move-in ready, this residence offers spectacular daily views of the Gulf, pool, and lush tropical landscaping- best enjoyed on the 200 sqft screened terrace where there’s plenty of room for reading, relaxing or toasting the sunset and dining. This lovely residence has been loved and meticulously upgraded with superior materials and workmanship. The gourmet kitchen features a spacious central cooking island with Electrolux 6-burner cooktop and hood, brushed stainless GE Monogram and Bosch appliances including a stacked double oven, as well as granite countertops, and solid light cherry cabinets. A breakfast bar, wine rack and built-in office complement this kitchen with added functionality. Additional luxury finishes include raised ceilings, crown molding, hidden surround-sound speakers, and spa-inspired bathrooms with custom mosaic-tile showers, Kohler fixtures, and rain showerheads. The Longbeach Community offers 9.2 acres of Gulffront beach homes just a 5-min walk to the exclusive amenities like private beach access to the quartz-white sand of Longboat Key's beaches, a heated pool, private tennis, and ample parking. In addition to idyllic award-winning beaches, Longboat Key living means exquisite waterfront dining, boutique shopping in St Armands Circle, and unparalleled golf courses and tennis courts. The Longboat Key lifestyle awaits you to create new everlasting memories here in paradise!

7115 Gulf Of Mexico Drive Unit 23, Longboat Key

7030 Poinsettia Avenue, Longboat Key
$800,000
2 Beds ⋅ 2 Baths ⋅ Long Beach SubDv. ⋅ 34228 Zip Code
Enjoy as an investment opportunity or your own private retreat in the highly desirable Village neighborhood on the north end of Longboat Key, with no HOA fees and convenient Gulf Beach and Sarasota Bay access. Set on an oversized lot, the property includes a main residence and a separate guest cottage connected by an inviting breezeway, creating excellent flexibility for seasonal use or extended stays. Each space offers privacy and comfort, enhancing overall livability and guest experience. This turnkey furnished property has been thoughtfully restored to preserve its historic charm. Key updates include a metal roof, impact windows, new cabinetry, and updated appliances, providing both character and peace of mind. The main home welcomes you with an enclosed front porch and a warm, inviting living area complete with a wood-burning fireplace, pine wood flooring, and shiplap accents. The updated kitchen features striking countertops and extended workspace perfect for entertaining, with direct access to a private courtyard deck shaded by a majestic tree. The primary bedroom offers vaulted ceilings and a large walk-in closet. The primary bathroom is also tastefully updated. The guest cottage includes its own entrance, ensuite bathroom, private patio, and full kitchenette, making it well suited for guest accommodations or extended stays. Outdoor amenities further enhance the property’s appeal. A covered entertaining area overlooks the pool and spa within a screened lanai, complemented by a well-appointed covered outdoor kitchen. The spacious paver patio and lush tropical landscaping create a private resort-style setting that appeals to long-term or seasonal residents and guests alike. The oversized lot provides ample parking, including space for a boat or golf cart, an added benefit in this beach to bay community. With convenient access to a boat ramp, nearby beaches, waterfront dining and local shops, this charming neighborhood enjoys strong demand. Turnkey and ready to enjoy or generate annual or seasonal rental income, the seller is open to offers.

7030 Poinsettia Avenue, Longboat Key

1445 Gulf Of Mexico Drive Unit 103, Longboat Key
$800,000
3 Beds ⋅ 3 Baths ⋅ Players Club SubDv. ⋅ 34228 Zip Code
Welcome to Residence #103 at 1445 Gulf of Mexico Drive, located within the prestigious Players Club on Longboat Key. This exceptional 550-foot Gulf-front community offers an unparalleled coastal lifestyle, and this residence presents a rare opportunity—available for the first time in 37 years. Originally the building’s model home, this thoughtfully designed condominium combines timeless elegance with spacious comfort. This beautifully maintained residence features three bedrooms, two and a half baths. The third bedroom/den is complete with twin Murphy beds and built-in storage. The spacious living and dining area opens to a wall of sliding glass doors leading to an expansive 30-foot open-air balcony, where you will enjoy sweeping views of the Gulf of Mexico, overlooking the 70-foot heated saltwater swimming pool, spa, lush tropical landscaping, and breathtaking sunsets. Just steps from the pristine beach, this outdoor retreat invites you to relax, read, listen to the waves, and savor spectacular evening skies. Inside, the home offers a seamless blend of style and functionality. The spacious primary suite features sliding glass doors to the balcony, a generous walk-in closet, and a split en-suite bath with dual vanities, a spa-like soaking tub and shower, and a large window that fills the space with natural light. The second en-suite bedroom, privately positioned off the front hallway, is generously sized, offers abundant natural light, and includes a large walk-in closet—perfect for guests. Additional conveniences include a powder room, in-unit laundry, interior storage, and a private storage closet just outside the front door. The residence also includes assigned under-building parking and access to bike storage. Residents of Players Club enjoy resort-style amenities, including a newly renovated clubhouse with a state-of-the-art fitness center, library, catering kitchen, and inviting indoor and outdoor social spaces. Four Har-Tru tennis courts, pickleball, a putting green, beautifully maintained grounds, a security gate, and on-site management provide both luxury and peace of mind. Ideally situated on the desirable south end of Longboat Key, this community is just minutes from Publix, the renowned St. Regis Longboat Key Resort, the upscale boutiques and fine dining of St. Armands Circle, and the vibrant cultural attractions of downtown Sarasota. This is a rare opportunity to own a distinguished Gulf-front residence in one of Florida’s most sought-after coastal communities—where luxury, location, and lifestyle come together beautifully.

1445 Gulf Of Mexico Drive Unit 103, Longboat Key

2045 Gulf Of Mexico Drive Unit M1-505, Longboat Key
$800,000
2 Beds ⋅ 2 Baths ⋅ Seaplace SubDv. ⋅ 34228 Zip Code
Fully RE-DESIGNED and RENOVATED 2-bedroom, 2-bath condo in Seaplace with PARTIAL GULF VIEWS. Completed in 2023, this residence showcases over $200K in UPSCALE UPGRADES AND FINISHES. Crafted for both elegance and durability, the home features HURRICANE IMPACT-rated windows and sliding glass doors, providing enhanced storm protection, improved energy efficiency, and year-round peace of mind. The spacious QUARTZ KITCHEN ISLAND serves as both a functional hub and an artistic focal point, anchoring the open-concept living area with style and intention. The island includes seating and additional storage underneath. The kitchen is outfitted with HIGH-END GE Café Series APPLIANCES, including a dual oven, refrigerator with beverage drawer and flex zones, dishwasher, microwave, and wine fridge. Locally crafted CUSTOM SHAKER CABINETRY with soft-close drawers, a subway tile backsplash, Falmec hood, and designer gold plumbing fixtures and cabinet pulls complete the space. A thoughtfully crafted ENTERTAINMENT BAR with floating shelves, glass-front cabinets, and a built-in WINE FRIG adds flair and functionality—an efficient and elegant use of space.The spacious screened lanai, fitted with no-see-um proof screens, offers Gulf views and ample room for dining and relaxation.The primary suite is designed as a private retreat, with a spa-like bathroom featuring dual vanities, a Toto toilet, and a frameless glass shower with smooth pebblestone flooring, in-line drains, and a built-in bench seat.Custom tray ceilings in the living room and bedrooms add architectural interest, complemented by modern ceiling fans and enhanced LED lighting. All closets and the fully equipped laundry room are customized by Closets by Design for optimal storage. LG ThinQ smart washer and dryer included. Throughout the home, you’ll find luxury waterproof vinyl flooring and electric room-darkening shades in both bedrooms. A dedicated covered parking spot under the building—a rare and valuable feature—comes with the unit. Seaplace association has approved BRAND NEW front doors for each residence, which once installed will modernize the look of the complex as well as allow more light to filter into the unit through translucent impact glass panels. Seaplace residents enjoy a half-mile of private beachfront with beach chairs and umbrellas, two swimming pools, two spas, a kiddie pool, three Har-Tru tennis courts, a playground, and a one-mile walking trail. The updated clubhouse includes a fitness center, sauna, library, catering kitchen, AV lounge, and a Gulf-front patio with multiple grills.With effortless access to fine dining, shopping, and Sarasota’s world-class arts and culture, this Seaplace condo offers a rare opportunity for refined island living.

2045 Gulf Of Mexico Drive Unit M1-505, Longboat Key

1211 Gulf Of Mexico Drive Unit 105, Longboat Key
$800,000
2 Beds ⋅ 2 Baths ⋅ Promenade SubDv. ⋅ 34228 Zip Code
Exceptional opportunity to own this beautiful first-floor condominium at The Promenade, offering the perfect balance of comfort, and coastal charm with nearly 400 feet of private beach frontage and partial views of the Gulf of Mexico from almost every room. This spacious two-bedroom, two-bathroom split floor plan features a bright, open layout ideal for entertaining or relaxed living. The kitchen flows seamlessly into the expansive living and dining areas, creating a connected and inviting space. Enjoy stunning northwest sunset views from the comfort of the great room or step outside to the private balcony for a peaceful retreat overlooking the Gulf. The elegant primary suite offers balcony access, a large walk-in closet, and a spa-like en-suite bath with a soaking tub and walk-in shower. The generously sized guest bedroom is perfect for visitors or can be easily adapted as a home office or hobby room. The Promenade offers a true resort-style experience with a 24-hour staffed gatehouse, full concierge services, and secure under-building assigned parking. Residents enjoy a heated Gulf-front pool and spa, a spacious sundeck with shaded gazebo and grilling area, four Har-Tru tennis courts, a well-equipped fitness center, a craft room, and inviting social spaces. Private beach access lined with charming tiki huts completes the picture of effortless coastal living. Don’t miss this rare opportunity to embrace the ultimate Longboat Key lifestyle, where every day feels like a vacation

1211 Gulf Of Mexico Drive Unit 105, Longboat Key

4234 Gulf Of Mexico Drive Unit G2, Longboat Key
$800,000
3 Beds ⋅ 2 Baths ⋅ Pelican Harbour & Beach Club SubDv. ⋅ 34228 Zip Code
Motivated Seller—Priced to Sell! Enjoy sweeping Sarasota Bay views from this refreshed 3-bedroom, 2-bath end-unit condo in the highly sought-after Pelican Harbour & Beach Club on Longboat Key. This light-filled second-floor residence offers over 1,600 sq ft of coastal living with panoramic water views from the living room, primary suite, and private screened balcony. The spacious floor plan includes a bright living area, tranquil dining space, and a serene owner’s suite with lanai access and a beautifully renovated ensuite bath. Recent improvements include new carpet, recessed lighting, interior paint, mounted TVs, and a new AC (2025), water heater (2024) and roof (2023). Additional conveniences include in-unit laundry and covered parking and private Beach Access directly across the street. Pelican Harbour provides resort-style amenities: 200 ft of private deeded beach with new lounge chairs, heated pool and clubhouse, marina with boat slips (up to 28 ft) and kayak launch, plus tennis and pickleball courts. Pet-friendly community allowing up to two pets (dog/cat combinations permitted). Professionally managed with new roofs and hurricane-rated carports. Ideally located mid-key, just minutes to St. Armands Circle, Bayfront Park, and the new St. Regis Resort. Perfect as a full-time residence, seasonal retreat, or investment property—this bayside condo offers an unbeatable combination of location, amenities, and motivated-seller value.

4234 Gulf Of Mexico Drive Unit G2, Longboat Key

4725 Gulf Of Mexico Drive Unit 309, Longboat Key
$785,000
2 Beds ⋅ 2 Baths ⋅ Sand Cay A Condominium SubDv. ⋅ 34228 Zip Code
Welcome to Sand Cay Beach Resort—one of Longboat Key’s premier beachfront destinations and one of the few communities on the island permitting flexible 1–7 day rentals, making it exceptionally attractive for both personal use and income potential. With an outstanding on-site management team handling the details, ownership is truly effortless. This rarely available third-floor residence features soaring vaulted ceilings exclusive to top-floor units, creating an open, airy ambiance filled with natural light. The beautifully updated kitchen opens seamlessly to the living and dining areas, while coastal-inspired finishes throughout enhance the relaxed Gulf-front lifestyle. Offered completely turnkey, this well-established vacation rental boasts a strong income history and presents an exceptional investment opportunity. Nestled within an intimate community offering 340 feet of pristine Gulf frontage, Sand Cay delivers a true resort-style experience. Amenities include a heated beachfront pool, tennis courts, shuffleboard, basketball area, barbecue stations, and a full-time on-site manager with a convenient in-house rental program. Perfectly positioned just minutes from the boutiques and fine dining of St. Armands Circle and the vibrant arts and culture of downtown Sarasota, the location is as compelling as the property itself. Light-filled and ideally situated between the pool and the beach, this two-bedroom, two-bath residence also features a spacious living and dining area, a cozy den or office nook, and a private balcony with awning and Gulf views—perfect for morning coffee or relaxing after a day in the sun. Your slice of Longboat Key paradise awaits. Schedule your private showing today.

4725 Gulf Of Mexico Drive Unit 309, Longboat Key

1925 Gulf Of Mexico Drive Unit G8-303, Longboat Key
$775,000
2 Beds ⋅ 2 Baths ⋅ Seaplace SubDv. ⋅ 34228 Zip Code
Welcome to this beautifully updated coastal retreat, where style, comfort, and functionality come together seamlessly. This light-filled residence features an open-concept layout with wide-plank tile flooring throughout, creating a clean, modern look that’s perfect for beachside living. The updated kitchen is both stylish and functional, showcasing granite countertops, custom cabinetry, stainless steel appliances, and a spacious breakfast bar—ideal for entertaining or casual dining. Relax and unwind in the spacious living area, which flows effortlessly to the screened lanai—perfect for enjoying morning coffee or evening breezes with partial Gulf views and lush tropical surroundings. The primary suite offers a serene escape with tasteful coastal décor and ample storage, while the guest bedroom is thoughtfully designed for comfort and privacy. The fully renovated bathroom features a walk-in glass-enclosed shower, modern tilework, and dual vanities for added convenience. Additional highlights include: In-unit washer & dryer Updated finishes throughout Residents of Seaplace enjoy approximately ½ mile of pristine Gulf beach frontage and an impressive array of amenities across 42 beautifully landscaped acres. Highlights include two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a well-equipped fitness center, and a clubhouse featuring a kitchen, library, and sauna. Additional amenities include a playground, community grills, on-site management, and a 24-hour staffed gatehouse for security. Enjoy breathtaking sunsets, peaceful walking paths, and a truly low-maintenance island lifestyle—all at an exceptional value. Schedule your private showing today!

1925 Gulf Of Mexico Drive Unit G8-303, Longboat Key

2326 Harbour Oaks Drive, Longboat Key
$775,000
3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code
Welcome to effortless coastal living in this beautifully maintained, fully furnished end-unit villa on Longboat Key. Offering nearly 2,400 square feet of thoughtfully designed living space, this exceptional residence combines the spaciousness and privacy of a single-family home with the convenience of maintenance-free living—all just moments from the Gulf's renowned white-sand beaches. From the moment you step inside, soaring vaulted ceilings, abundant natural light, and an open, airy floor plan create a warm and inviting atmosphere. Designed for both comfortable everyday living and effortless entertaining, the home offers multiple gathering spaces, including a formal living room with a charming wood-burning fireplace and expansive sliding glass doors that open to an impressive 740-square-foot private terrace overlooking peaceful pond views. The kitchen is both stylish and functional, featuring granite countertops, updated cabinetry, rich wood flooring, plantation shutters, and a skylight that fills the space with natural light. Recent upgrades, including a new roof and new air-conditioning system completed in 2025, provide added comfort and peace of mind. Adding to the home's unique character are two private atriums that bring the outdoors in, creating bright, tranquil spaces throughout the residence. A versatile office with a built-in Murphy bed offers the flexibility to easily serve as a fourth bedroom, while the spacious primary suite provides a relaxing retreat with comfortable accommodations for family and guests. Additional highlights include a private two-car garage with organized storage, a heated community pool and spa, and exclusive membership to the gated Bay Isles Beach Club, where residents enjoy private Gulf-front beach access and dedicated parking. Perfectly located near world-class beaches, boating, waterfront restaurants, boutique shopping, and the renowned Longboat Key Club's golf, tennis, pickleball, marina, and dining amenities, this residence places the very best of island living right at your doorstep. Beautifully furnished, impeccably maintained, and move-in ready, this is an exceptional opportunity to enjoy the relaxed elegance and coastal lifestyle that make Longboat Key one of Florida's most sought-after destinations.

2326 Harbour Oaks Drive, Longboat Key

4235 Gulf Of Mexico Drive Unit T101, Longboat Key
$775,000
1 Beds ⋅ 1 Baths ⋅ Turtle Crawl SubDv. ⋅ 34228 Zip Code
Turnkey furnished and direct Gulf-front, this exceptional ground-floor residence at Turtle Crawl Inn on Longboat Key offers both effortless beachfront living and remarkable, documented rental performance. Residence T-101 has averaged a yearly gross rental income of approximately $90,000 over the past three years, making it a compelling opportunity for investors, seasonal owners, or those seeking a flexible coastal retreat with established returns. Positioned directly on the sand, this rare walk-out Gulf-front residence features a private patio just steps from the turquoise waters of the Gulf of Mexico—ideal for enjoying sunset views over the shoreline. The professionally designed interior blends coastal comfort with modern updates, featuring imported contemporary porcelain flooring from Italy throughout the open layout. The kitchen offers updated cabinetry, stone countertops, white appliances, and a seamless connection to the living and dining areas—perfect for relaxed beachside living or hosting guests. Impact windows with plantation shutters and impact glass sliders enhance peace of mind while filling the space with natural light. The spacious bedroom accommodates guests comfortably, while the completely updated bathroom (2021) showcases clean, timeless finishes. Step outside to the travertine-tiled Gulf-front patio, your private vantage point overlooking the beach, dunes, and horizon—an amenity highly valued by renters and owners alike. Turtle Crawl Inn is known for its laid-back resort atmosphere and strong rental appeal, offering a heated swimming pool, beachside cabanas, gas grilling stations, picnic areas, fishing opportunities, a putting green, shuffleboard courts, and deeded beach access. Flexible rental options make this community especially attractive for income-focused ownership. ** The Seller requests NO SOLICITATION COMMUNICATIONS of any kind. LISTING WITHDRAWN, WILL BE RE-ACTIVATED.** Located on the desirable mid-island stretch of Longboat Key, the property is minutes from waterfront dining, marinas, Bayfront Park, Joan M. Durante Park, and boating access. Anna Maria Island lies just to the north, while St. Armands Circle and downtown Sarasota’s shopping, dining, and cultural attractions are a short drive south. Whether you’re seeking a high-performing income property, a personal beachfront escape, or a blend of both, this Gulf-front residence delivers proven rental history, prime location, and direct beach access—a rare combination on Longboat Key.

4235 Gulf Of Mexico Drive Unit T101, Longboat Key

580 Neptune Avenue, Longboat Key
$775,000
Coquina Beach SubDv. ⋅ 34228 Zip Code
IT'S BIGGER THAN IT LOOKS! I bet you've heard that before but it's true! Rare find! & NO BUILDER ATTACHMENT! Just under a 1/2 acre homesite located on a quiet street & available now to build your dream home! Perfectly situated just 1 block to the public beach access that leads straight out to the Gulf Mexico! If you're new to Longboat Key, rest easy that rental restrictions limit to renting only one time a month so it doesn't feel like a tourist trap! It's relaxing, serene & will be your own escape from all the hustle & bustle. Did you know Longboat has amazing sidewalks for safe walking & bike riding that are wide & make it EASY to stay active. Literally, there is NO EXCUSE to not be active in a place like this. It is truly paradise. This property offers the ideal blend of luxury, convenience & peaceful, coastal living. Sewer & electric are present on the property in addition to an Artesian well for irrigation. Enjoy the island lifestyle with a short walk or bike ride to the Longboat Key Moorings Marina, Publix, charming boutiques, the library, churches, tennis center or Bayfront Park for pickleball & yoga. Only a short ride to Anna Maria Island, IMG Academy, world class medical or head south to St Armand's Circle for fine dining, the arts & less than an hour to three major airports: Tampa International, Sarasota/Bradenton or Clearwater/St Pete. Buyer is responsible to verify all boundaries. AMAZING SUNSETS INCLUDED!

580 Neptune Avenue, Longboat Key

4835 Gulf Of Mexico Drive Unit 302B, Longboat Key
$770,000
2 Beds ⋅ 2 Baths ⋅ Westchester Condo Apts SubDv. ⋅ 34228 Zip Code
Virtually Staged. Experience the ultimate beachfront lifestyle in this stunning 1,393 sq. ft. 2-bedroom, 2-bathroom retreat on Longboat Key. Perfectly positioned on the third floor, this home offers amazing views of the beautiful beaches and the endless Gulf horizon—visible from nearly every room! Wake up to the sound of waves in the master suite, where sliding doors open to a private balcony with breathtaking ocean views. Both bedrooms feature spacious walk-in closets, ceiling fans, while both bathrooms have been fully remodeled with modern, high-end finishes and Toto washlet toilets. The newly updated kitchen boasts a sleek induction stove with a vented range hood, perfect for cooking with a view. New AC, LED lighting, and brand-new impact sliding doors enhance comfort and efficiency. Beyond your private oasis, take advantage of resort-style amenities, including two Gulf-front heated pools unique to the Westchester, Elevators, tennis courts, and direct beach access. Plus, you’re conveniently located just minutes from Publix, top-rated restaurants, and boutique shopping. Enjoy short rides to the vibrant St. Armands Circle and downtown Sarasota, where world-class dining, entertainment, and cultural attractions await. This is coastal luxury at its finest—don’t miss your chance to own a piece of paradise!

4835 Gulf Of Mexico Drive Unit 302B, Longboat Key

7155 Gulf Of Mexico Drive Unit 22, Longboat Key
$760,000
2 Beds ⋅ 2 Baths ⋅ Long Beach SubDv. ⋅ 34228 Zip Code
Set in the sought-after Longbeach community on the northern end of Longboat Key, this beautifully updated, Turnkey Furnished 2BR/2BA residence blends comfort, elegance and effortless Gulfside living. Poised on the second floor, it enjoys picturesque views over the community’s manicured landscape and out toward the shimmering waters of the Gulf. Inside, over 1,100 sq. ft. of refined space unfolds in soothing neutral tones that let the views take center stage. High-impact glass, crown molding and thoughtful design touches elevate the interior, creating a light and welcoming ambiance throughout. The galley kitchen is a model of both style and functionality, featuring stone countertops, white cabinetry, stainless steel appliances and a quaint adjacent workspace perfect for a home office or breakfast nook. The dining area flows easily into the living room, where sliders open to a screened terrace overlooking the lush greenery and the Gulf beyond, creating an ideal space for relaxing or entertaining. The spacious primary suite is a serene retreat with a large walk-in closet, direct terrace access and a tastefully updated bath with contemporary finishes. The guest bedroom is equally inviting, offering ample space and privacy for visiting family or friends. Located directly on the beach, Longbeach offers residents an active, resort-style lifestyle with a heated pool, tennis courts and onsite management, all just moments from the island’s popular restaurants and shops. The property will be leased from 3/1/26 to 4/30/26 at $8,000 p/month.

7155 Gulf Of Mexico Drive Unit 22, Longboat Key

3466 Winding Oaks Drive Unit 35, Longboat Key
$758,500
2 Beds ⋅ 2 Baths ⋅ Winding Oaks SubDv. ⋅ 34228 Zip Code
Located in one of the most sought-after villa communities on Longboat Key, this well-kept 2-bedroom, 2-bath home in Winding Oaks lives more like a single-family residence—without all the upkeep. Behind the gates of Bay Isles, it offers a great opportunity to enjoy a quiet, established neighborhood known for its natural beauty and relaxed feel. A paver driveway and walkway, surrounded by mature landscaping, lead you to the front door. Inside, high ceilings and warm wood floors immediately make the space feel open and inviting. The finishes are neutral and timeless, and the natural light really does the rest. Impact glass throughout adds both comfort and peace of mind. The main living area flows easily, with a striking corner of sliding glass doors that brings the outdoors in and opens to a spacious, screened, deck. It’s the kind of space you’ll actually use—whether that’s for entertaining, relaxing, or just enjoying the greenery around you. The kitchen is nicely laid out with stone countertops, stainless appliances, a tray ceiling, and a large window that keeps things bright. Both bedrooms are generously sized. The primary suite feels like a true retreat, with vaulted ceilings, a walk-in closet, and sliding doors that open to the deck with peaceful nature views. The bathroom is spacious, featuring dual vanities, a Jacuzzi tub, walk-in shower, and well-done tile details. Additional highlights include a two-car garage and a floor plan that offers a nice balance of openness and privacy. Winding Oaks is part of the Bay Isles Harbourside golf course community and offers a gated entrance, community pool, and access to Bay Isles amenities—including deeded beach access through the private Bay Isles Beach Club. It’s an easy, comfortable lifestyle in one of Longboat Key’s most desirable communities.

3466 Winding Oaks Drive Unit 35, Longboat Key

3459 Byron Lane, Longboat Key
$755,000
3 Beds ⋅ 3 Baths ⋅ Coreys Landing SubDv. ⋅ 34228 Zip Code
Positioned along the par-5 fairway with tranquil lake views beyond, this well-priced attached villa offers an inviting opportunity in one of Longboat Key’s most desirable neighborhoods. Set within Corey’s Landing, tennis courts sit just across the street and the beach is moments away, creating a lifestyle that balances recreation, relaxation and everyday ease. A quaint paver walkway leads to the front entrance, where tile floors, soaring cathedral ceilings and an abundance of windows create an interior that feels open, light and comfortable from the start. The floor plan flows naturally, connecting living and dining spaces in a way that works equally well for quiet days at home or gathering with friends. The kitchen is functional and ready for a future refresh, currently finished with all-white cabinetry and appliances, plus a breakfast bar that adjoins the dining area and living room. From here, a wall of glass and sliders opens to an expansive two-level screened lanai with both covered and open areas. It is a wonderful extension of the living space, offering room to dine, lounge or simply enjoy views of the fairway and water while watching play unfold on the course. The primary suite is generously sized, highlighted by a cathedral ceiling, direct lanai access and a spacious bath with freestanding tub, walk-in shower and dual vanities. A comfortable guest bedroom includes its own en suite bath, while a third bedroom currently functions as an office, offering flexibility for guests or hobbies. Residents of Corey’s Landing enjoy a relaxed, amenity-rich setting with a pool and spa, tennis courts, deeded beach access and a private beach club, all tucked behind the gates of Bay Isles. Memberships to the Longboat Key Golf & Tennis Country Club and access to deepwater slips are available. Large dogs are permitted with some restrictions, completing a setting that blends value, location and the ease of island living on Longboat Key.

3459 Byron Lane, Longboat Key

815 Bayport Way Unit 815, Longboat Key
$750,000
2 Beds ⋅ 2 Baths ⋅ Bayport Bch & Ten SubDv. ⋅ 34228 Zip Code
Welcome to a true hidden gem of tropical paradise at Bayport Beach and Tennis Club on Longboat Key. Designed by renowned architect Tim Seibert, this one-of-a-kind community spans 27 lush, tropical acres and offers an unmatched coastal lifestyle with 1,200 feet of pristine private beach, where chairs and umbrellas are ready for you to enjoy endless days along the Gulf. As you arrive, you’re immediately surrounded by beautifully maintained grounds and the relaxed, resort-style atmosphere that makes this community so special. Stepping inside this spacious 2 bedroom, 2 bathroom furnished residence, you’re welcomed by a light and airy interior with terracotta-look tile flooring flowing throughout the main living areas, setting a warm coastal tone. The kitchen has been thoughtfully renovated with all new cabinetry, under-cabinet lighting, quartz countertops, a modern backsplash, and stainless steel appliances, creating a clean and functional space that opens seamlessly into the living and dining areas. The expansive living room is both inviting and impressive, designed to feel like a single-family home, with stunning Sarasota Bay views that instantly capture your attention. Shutter doors provide privacy while leading into a sunroom, offering a flexible space to relax and take in the scenery. The owner’s suite is a true retreat, complete with a dedicated office nook perfectly positioned to enjoy peaceful water views. The ensuite bathroom features dual quartz-topped vanities and a walk-in closet, combining comfort and convenience. A split bedroom floorplan ensures privacy, with the guest bedroom offering its own walk-in closet and easy access to the updated guest bathroom. An in-unit laundry area adds to the everyday ease of living. Step outside onto your expansive private deck, where breathtaking views of Sarasota Bay create the perfect backdrop for morning coffee, evening wine, or entertaining guests while surrounded by nature. Bayport Beach and Tennis Club offers an incredible array of amenities, including a Junior-Olympic heated pool, four Har-Tru tennis courts, a fitness center, fishing pier, kayak storage + launch, and an active clubhouse filled with social events. Scenic walking trails wind through the property, where you’ll often spot local wildlife such as osprey, herons, ibis, and egrets, enhancing the serene, natural setting. Just moments away, Bayfront Park offers pickleball courts, green space, and stunning bay views, while St. Armands Circle provides exceptional shopping and dining. A short drive over the iconic Ringling Bridge brings you into vibrant downtown Sarasota, known for its world-class arts scene, including theaters, museums, galleries, and waterfront dining. From private beach access to unmatched amenities and breathtaking bay views, this residence offers the perfect blend of comfort, nature, and coastal elegance in one of Longboat Key’s most sought-after communities.

815 Bayport Way Unit 815, Longboat Key

636 Tarawitt Drive, Longboat Key
$750,000
2 Beds ⋅ 2 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code
One or more photo(s) has been virtually staged. A NEW PRICE!! Wake up to tranquil canal views and end your day with sunsets just steps from the Gulf — all on Longboat Key! Priced UNDER $1M & Renovation Loan Eligible! Opportunities like this are rare, and this property is priced to sell fast. Featuring 2 bedrooms, 2 bathrooms, and a 1-car garage, this home also includes a separate 1-bedroom, 1-bathroom GARAGE APARTMENT with its own entrance—perfect for SHORT TERM RENTALS or guest accommodations. Sitting directly on a CANAL with room to dock a boat, this home is a dream for boaters and beach lovers alike. The 120 feet of reinforced seawall ensures lasting waterfront stability. Enjoy DEEDED BEACH ACCESS, just a short stroll away, where you can witness the magic of turtle nesting season. Walk to dog-friendly Durante Park, the scenic shores of Sarasota Bay, and some of Longboat Key’s most popular restaurants, including Lo’Key and Harry’s Continental Kitchen. Cannon’s Marina is nearby for all your boating needs, and the trolley provides easy access to Anna Maria Island. The home boasts a 2024 AC and a 5-year-old tile roof, giving you peace of mind on major updates. The private outdoor space is perfect for soaking up Florida’s year-round sunshine. Renovation Loan Eligible – Plus an Incredible Build Opportunity! This property qualifies for a renovation loan, allowing you to finance both the purchase and renovations—an incredible opportunity to customize your dream home while keeping costs manageable. Waterfront. Deeded beach access. Room for a boat. Rental potential. And all for UNDER $1 MILLION! This is an **unbeatable opportunity** in one of the most desirable locations on the Gulf Coast. Don’t miss out—schedule your showing today!

636 Tarawitt Drive, Longboat Key

2045 Gulf Of Mexico Drive Unit M1-511, Longboat Key
$749,000
2 Beds ⋅ 2 Baths ⋅ Seaplace SubDv. ⋅ 34228 Zip Code
Experience breathtaking, full Gulf views from this beautifully maintained 5th-floor residence at Seaplace on Longboat Key. This furnished 2-bedroom, 2-bath condominium offers the perfect blend of comfort, space, and coastal charm, with expansive living and dining areas designed to capture stunning water views and natural light throughout. Step out to your private lanai and enjoy panoramic sunsets, gentle sea breezes, and the soothing sounds of the Gulf—your own peaceful retreat just steps from the beach. The spacious primary suite provides a relaxing escape, while the guest bedroom offers comfort and privacy for visitors. Seaplace residents enjoy resort-style amenities across 42 acres of lush, meticulously maintained grounds, including a half-mile of private beachfront, two heated swimming pools with spas, a fitness center, Har-Tru tennis courts, walking paths, outdoor grilling areas, and an active, well-managed association. Whether you’re seeking a full-time residence, vacation getaway, or investment opportunity, this unit is priced to sell and ready for you to start enjoying the Longboat Key lifestyle. Schedule your private showing today!

2045 Gulf Of Mexico Drive Unit M1-511, Longboat Key

660 Linley Street, Longboat Key
$740,000
3 Beds ⋅ 3 Baths ⋅ Long Beach SubDv. ⋅ 34228 Zip Code
Owner Financing Available! Nestled in the heart of Longboat Key's coveted historic Longbeach Village, this exceptional island retreat offers 3 bedrooms and 3 bathrooms across two charming Key West-style cottages just moments from both the most pristine Gulf beaches and beautiful Sarasota Bay. This rare property blends timeless coastal elegance with modern updates in a private, landscaped setting. The main residence features a bright, open floor plan and an updated kitchen with quartz countertops, hardwood cabinetry, newer appliances, and abundant natural light. The detached guest cottage offers a private 1-bedroom, 1-bath layout complete with its own kitchen and entrance, providing the perfect space for guests, extended family, or added flexibility. Outdoor living is equally inviting with a spacious entertaining deck, tiki bar, and mature tropical landscaping that creates a true sense of privacy and retreat, with room to add a pool. Recent improvements include a new roof on the main residence (2026), Hardie Board siding, updated cabinetry, quartz countertops, updated appliances throughout, fresh paint, and a newer A/C system, offering peace of mind and modern comfort. With proven rental income, this property serves as an exceptional investment opportunity while maintaining strong personal use potential. Situated in the highly desirable “Village“, one of the most charming, inviting, and community-driven neighborhoods on Longboat Key, residents enjoy a rare blend of coastal character and close-knit island living. Just moments from Whitney Beach, community fishing docks, a boat and kayak launch, and exclusive waterfront dining destinations such as Mar Vista and The Shore, this home captures the essence of luxury island living in one of the island’s most beloved enclaves. Schedule your private showing TODAY before it’s gone !!

660 Linley Street, Longboat Key

2155 Harbourside Drive Unit 804, Longboat Key
$740,000
3 Beds ⋅ 2 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code
Situated behind gates of the coveted Bay Isles on Longboat Key is the private enclave of Harbour Oaks. This meticulously renovated second floor residence offers an effortless blend of comfort, refinement, and coastal living. Offering an expansive 3 bedrooms, 2 bathrooms as well as a 2-car garage overlooking one of the most pristine Longboat Key Club golf courses. Furniture conveys with a few personal exceptions. Vaulted ceilings as well as skylights allow natural light to flood through the entire space. The custom modern kitchen is well-appointed with KitchenAid appliances including a 36-inch induction cooktop, built-in oven, refrigerator and dishwasher as well as a dedicated wine refrigerator within the expansive kitchen island. The master bedroom offers vaulted ceilings with a connected terrace to enjoy your morning coffee or watch beautiful Gulf sunsets. The primary bath exudes a sense of being at a spa with its tiled shower, glass shower door and double sink vanity. The third bedroom is currently being used as an office and gym, however could easily be set up as a bedroom. Harbour Oaks is also pet friendly and close to shopping, golf, tennis, beach and bay. Walks and bike rides can be enjoyed in one of the most scenic areas on Longboat Key. Bay Isles offers an exceptional coastal lifestyle including two fully staffed, 24-hour security entrances and exclusive access to a private, gated Gulf-front beach club. Residents have access to a thoughtfully appointed beachside retreat featuring a shaded pavilion, picnic spaces, restrooms, dedicated beach chair storage, grilling stations, and generous parking. Within minutes, access the famous St Armand’s Circle with its exceptional shopping and dining amenities. Cross the iconic Ringling Bridge to downtown Sarasota, which is well known for world-class theater, culture and dining. Additional amenities are available within Bay Isles upon joining the Longboat Key Club.

2155 Harbourside Drive Unit 804, Longboat Key

How much is your home worth?

Get instant property value now!