Location: Longboat Key
Keyword(s): Booker Middle
Keyword(s) Middle School: Booker Middle
Do Not Show Listings
1912 HARBOURSIDE DR #604, LONGBOAT KEY, FL 34228
$850,00091 Days on yellowkey MLS ID: A4683819
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2207 Built: 1982 Tax: $7,734 (2025)Community: Fairway Bay 1Townhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,734
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Embrace the island life style within the gates of Longboat Key's premier resort community of Bay Isles. You'll love this spacious townhome-style condo in Fairway Bay. Designed with soaring ceilings and large windows to allow maximum light and expansive views of the neighborhood’s tropical foliage, this beautifully and thoughtfully renovated home offers lots of space for gatherings with friends or family. The main living area opens effortlessly to a screened porch through sliding doors, creating a bright and airy space perfect for entertaining. The open floorplan, cozy fireplace, freshly painted interiors, fully updated kitchen and bathrooms, two bedrooms, and abundant storage make this home as functional as it is inviting. Downstairs, a flexible bonus space off the oversized 2-car garage offers endless possibilities. This non-conforming, bonus area includes a spacious living room, a flex space (currently set up as a 3rd bedroom), a full bath, and laundry room – perfect for guests, hobbies, or working from home. Just a few steps away, enjoy one of the community’s pools and hot tubs, or explore all the amenities this vibrant neighborhood offers – another heated pool and hot tub, miles of manicured paths, a clubhouse, fitness center, tennis/pickleball courts, and 24-hour gated security. Plus, gain deeded access to the Bay Isles Beach Club, a private, gated Gulf-side retreat with a covered pavilion, parking, restrooms, grills, a beach volleyball court, and sunsets that will take your breath away. This home truly lives like a retreat. Just 10 miles from Anna Maria Island to the North, South 4 miles to St. Armands Circle, and another 4 to Downtown Sarasota, with plenty of shopping, dining, and entertainment options. Your tropical beach getaway is ready and waiting – come make it yours!
Listing is courtesy of: S&N REAL ESTATE, INC. (941-320-5482)
Listing Agent: Darlena Nelms (941-320-5482)
545 SANCTUARY DR #B305, LONGBOAT KEY, FL 34228
$2,495,000114 Days on yellowkey MLS ID: A4681142
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2580 Built: 1991 Tax: $25,314 (2025)Community: Sanctuary IiiCondo
Taxes:$25,314
Remarks: The Sanctuary behind the gates of the Longboat Key Club located on the beachfront is one of the most desirable addresses on Longboat Key, Florida. New to the market, this full on, direct Gulf view residence B305 in Building III at 545 Sanctuary Drive offers about 3,000 square feet with three bedrooms & 2 ½ bathrooms providing spacious and elegant beach front living. From the handsome double door entry, the gleaming marble floor dining area invites you into this luxurious condominium home. Then, you will be treated to a sparkling like diamonds daytime Gulf water views or in the evening, breathtaking sunsets in shades of purple & orange. These magnificent direct Gulf views can be enjoyed from the attractively furnished living room and the serene primary bedroom & of course from the 21-foot-long covered Gulf side terrace. This unique Carlyle floorplan also features a second, east facing private terrace which can be accessed through the guest bedroom as well as from the handsome kitchen as you enjoy morning sunrises with a cup of coffee. This beach retreat is in impeccable condition with high quality furnishings plus electric storm shutters on all sliding doors. This unit also has one under building garage space #150 plus a climate controlled storage cage. Decorated in neutral tones, this home offers coastal elegant style throughout. The cozy eat in kitchen has custom built light wood cabinetry, high end finishes, cream colored granite counter tops, tile backsplash & double ovens. The gracious, large primary bedroom suite is a tranquil retreat with Gulf water views, a large walk-in closet & a spa like En Suite bathroom with double sinks, a soaking tub & a walk-in shower. The Sanctuary offers an exclusive resort lifestyle. The beautiful beach front measures 1200 feet of pristine white sand. The resort style, heated Olympic sized swimming pool includes a 25 meter lap lane plus there is a separate outdoor whirlpool & fire pit area. Amenities include two lighted Har-Tru tennis courts & a state of the art fitness center with saunas located in the newly redecorated clubhouse which offers a fully equipped kitchen & entertainment room. On site management, 24 hour security & 18 acres of meticulously maintained grounds & beach enhance the sense of exclusivity & security.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Maruta Miluns (941-374-9702)
2600 HARBOURSIDE DRIVE #H-04, LONGBOAT KEY, FL 34228
$275,0008 Days on yellowkey MLS ID: A4694327
Bed: Bath: 0.0 Built: 1985Monthly Fee: $37,001 Tax: $2,306 (2025)Community: Bay IslesDock-Rackominium
Taxes:$2,306
Remarks: A favorite dock in the Marina! This 55 x 20 foot slip at Longboat Key Club Moorings is located at the Marina Village along the seawall! Easy access on and off the water to this H-dock slip. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 50 LOA; beam depends on the vessel. Call to discuss!
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
435 L AMBIANCE DR #L707, LONGBOAT KEY, FL 34228
$2,890,000266 Days on yellowkey MLS ID: A4663998
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2525 Built: 1994 Tax: $32,005 (2025)Community: L Ambiance At Longboat Key Club Ph 02Condo
Taxes:$32,005
Remarks: There are views… and then there is this view! From this desirable seventh-floor corner residence at L’Ambiance, the horizon unfolds in a breathtaking panorama—Gulf of Mexico sunsets ablaze to the west, Sarasota Bay shimmering to the east, the downtown skyline sparkling in the distance, and the manicured fairways of the Longboat Key Club Island side golf course below. Morning light and evening color become part of daily life, ever-changing and endlessly captivating. The arrival to this luxurious community, sets an immediate tone of distinction. A fountain-lined drive and 24-hour manned gate lead to a secured building where a full-time concierge delivers an unrivaled level of service. From welcoming guests to coordinating deliveries and attending to daily conveniences, the care and professionalism here is unrivaled. An elevator opens directly to your private foyer with double doors, revealing architectural details that add warmth and refinement—pecky cypress ceiling accents, a gracious dry bar, custom built-ins, soft cove lighting, and walls of glass that frame the surrounding water views. Expansive wraparound terraces extend the living spaces outward, creating an extraordinary setting for sunset dining, morning coffee, or effortless entertaining against a backdrop of sea and sky. The kitchen is thoughtfully appointed. The center prep island includes its own auxiliary refrigerator and freezer drawers—ideal for entertaining—while the breakfast nook overlooks the water and opens directly to the terrace. The spacious open living and dining areas are bathed in natural light, designed to showcase both the views and today’s modern lifestyle. This well-designed two-bedroom, two-and-a-half-bath residence lives beautifully—and is complemented by a significant advantage: reservable guest suites located just downstairs. Your visitors enjoy private, comfortable accommodations within the building, allowing you to preserve the serenity and elegance of your own home while hosting with ease. The split-bedroom floor plan enhances privacy, with the primary suite positioned to capture sweeping Gulf views. Recently enhanced with an oversized custom-fitted closet, it offers both luxury and thoughtful functionality. A full-sized laundry room, a rear service entrance, motorized blinds and draperies throughout, private parking, a storage unit, and a wine locker complete this exceptional offering. Residents of L’Ambiance enjoy resort-caliber amenities including a beachfront pool with cascading waterfalls, two Har-Tru tennis courts, a state-of-the-art fitness center, elegant social rooms, guest parking, and direct beach access. Just a couple of minutes away, world-famous St. Armand's Circle and over the Ringling bridge to everything downtown Sarasota has to offer.... fine dining, boutique shopping, and cultural attractions. Optional membership at the exclusive Longboat Key Club provides access to championship golf, premier tennis, several restaurants, boating facilities, and an active social calendar. This is more than a condominium—it is a private coastal sanctuary supported by impeccable service, refined amenities, and one of the most commanding vantage points on Longboat Key.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Pam Charron (941-993-3388)
2161 GULF OF MEXICO DR #3, LONGBOAT KEY, FL 34228
$4,395,000441 Days on yellowkey MLS ID: A4643048
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3800 Built: 2001 Tax: $40,054 (2024)Community: En ProvenceSpa: YesCondo
Taxes:$40,054
Tax Year: 2024
Remarks: Experience beachfront luxury in this spacious 3,800-square-foot 3-bedroom, 3.5-bath + den/office residence in the prestigious En Provence community on Longboat Key. A private elevator opens to a grand foyer with marble floors and tray ceilings. Expansive glass sliders in the living room frame stunning Gulf views and lead to an oversized terrace, perfect for seamless indoor-outdoor living. The expansive terrace is ideal for entertaining, featuring a built-in gas grill and outdoor cooking space overlooking the beach and lush grounds. The kitchen is both stylish and functional, featuring a center island, white cabinetry, and pristine white stone countertops. High-end appliances, including a natural gas cooktop, enhance the space, while a bold blue tile backsplash adds a striking contrast. The adjacent eat-in area, with Gulf views and a built-in desk, enhances both charm and practicality. The primary suite offers terrace access and a spa-like bath with a soaking tub, dual vanities, a makeup area, and a glass-enclosed shower. Two guest suites each include en-suite baths and scenic views. A large office provides flexibility and could easily convert into a fourth bedroom. Additional features include an in-residence laundry room and 2 car garage. Set on nearly six acres of pristine beachfront, En Provence blends elegance and convenience with a clubhouse, resort-style pool and spa, fitness center, and 24-hour guard gate. For those seeking additional amenities, optional membership to the nearby Longboat Key Club provides access to world-class golf, tennis, dining, a marina, and a spa.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Bruce Myer (941-376-5311)
3435 WINDING OAKS DR #18, LONGBOAT KEY, FL 34228
$949,000115 Days on yellowkey MLS ID: A4680403
REDUCED by $101,000 (9.6%) on 05/20/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2555 Built: 1988 Tax: $8,565 (2025)Community: Winding OaksSpa: NoCondo
Taxes:$8,565
Remarks: Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger. Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances. Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops. Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets. Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard. Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association. Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armand’s and Downtown Sarasota.
Listing Agent: Sean Clark (941-312-1146)
600 PUTTER LN, LONGBOAT KEY, FL 34228
$9,400,000511 Days on yellowkey MLS ID: A4633484
REDUCED by $1,100,000 (10.5%) on 05/19/2026
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 5982 Built: 2017Monthly Fee: $17 Tax: $69,287 (2025)Community: Country Club Shores, Unit 5, Sec 3Spa: YesSingle Family
Taxes:$69,287
Remarks: Welcome to Paradise on Longboat Key. This coastal modern home is located on the direct bayfront with a total of 270 feet of waterfront on an oversized lot consisting of 18,290 square feet. As you enter the home, your first view is a serene and expansive view of Sarasota Bay all the way from the Ringling Museum to Downtown Sarasota and the Ringling Bridge. Enjoy different types of boating as the dock includes 2 jet ski lifts and a 13,000 pound boat lift. With plenty of interior space, there are 5 bedrooms and 5 baths plus a dedicated office/den, family room and game room. Every bedroom is filled with bay views. As an added advantage, guests have their own space upstairs that includes a kitchenette. Outfitted with an elevator that stops at every floor, including the three car garage, convenience is just a step away. To enjoy the views outside, there is an outdoor surround lanai with disappearing screens, fireplace and summer kitchen. Large covered terraces on both levels provide views of beautiful sunrises over Sarasota Bay and Downtown Sarasota.
Listing is courtesy of: FLORIDA CAPITAL REALTY (786-953-5870)
Listing Agent: Kathleen Callender (941-321-3115)
842 BAYPORT WAY #842, LONGBOAT KEY, FL 34228
$675,00059 Days on yellowkey MLS ID: A4687058
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1983 Tax: $5,662 (2025)Community: Bayport Bch & Ten Ph FSpa: NoCondo
Taxes:$5,662
High School: None
Remarks: Poised within the Gulf to Bay community of Bayport Beach and Tennis Club, 842 Bayport Way offers 1570 square feet of effortless indoor-outdoor living. This first floor corner residence brings added natural light and extra privacy, giving the feeling of a private home with the ease of low maintenance living. The open layout includes a spacious kitchen, a primary bedroom with office space, walk-in closet and ensuite bath with dual vanities, as well as convenient in-unit laundry, covered parking and private storage closet. A combined dining and living area opens to a screened lanai and extended brick patio. This is a favorite spot for morning coffee, afternoon siestas and al fresco dining watching sunset skies. A garden gate leads to a direct side path to deeded beach access across the road. For pet owners, Bayport is small-pet friendly, and this walk-out location makes dog-walking especially easy. Spanning 27 acres of exquisitely landscaped tropical grounds, Bayport is celebrated for its timeless Tim Seibert architecture, exceptional amenities, and easy resort lifestyle. Residents enjoy a heated Jr. Olympic pool, clubhouse, fitness center, tennis, bocce ball, and shelled walking paths. Along the bay shoreline, a fishing pier, kayak launch and storage is perfect for morning paddles or simply enjoying nature . On the Gulf side, 1,200 feet of deeded beach access, complete with loungers and umbrellas, makes enjoying Longboat Key’s famously uncrowded beaches effortless. The condo’s split floor plan works well for year round living or a seaside escape. A favorable rental policy offers excellent income opportunity. Located mid-key, Bayport keeps you close to shopping, daily conveniences, great island dining, and the vibrance of Sarasota, all while feeling tucked away and serene. Settle in and enjoy a slice of true paradise on Longboat Key.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Rosemarie Mckee (941-504-9396)
815 BAYPORT WAY #815, LONGBOAT KEY, FL 34228
$850,00051 Days on yellowkey MLS ID: A4689278
0 Days Off yellowkey (back on 5/18/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1601 Built: 1981 Tax: $7,370 (2025)Community: Bayport Bch & Ten Ph ECondo
Taxes:$7,370
Remarks: Under contract-accepting backup offers. 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.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Keith Curcio (941-376-7683)
524 HORNBLOWER LN, LONGBOAT KEY, FL 34228
$2,900,00025 Days on yellowkey MLS ID: A4692210
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3045 Built: 1964Monthly Fee: $8 Tax: $14,777 (2025)Community: Country Club Shores Sec 2Spa: YesSingle Family
Taxes:$14,777
Remarks: Tucked along one of the most sought-after canals in Country Club Shores, 524 Hornblower Lane is a waterfront residence that fully embodies the Longboat Key lifestyle, where boating access, beach proximity, and refined coastal living intersect with intention. Set on a 0.28-acre canal-front homesite with 107 feet of water frontage, the property offers what experienced boaters immediately recognize as premier water: wide, deep canals with quick, unobstructed access to Sarasota Bay and the Intracoastal. A composite dock, dual boat lifts accommodating vessels up to approximately 38 feet, and a dedicated jet ski lift create a true boating compound, designed for both serious use and effortless enjoyment. Behind its stately, columned façade, the residence spans over 3,000 square feet of living space, thoughtfully updated over time with an effective build year of 2005 and continued improvements, including impact-rated glass, a newer metal roof (2025), and recently replaced mechanical systems. The layout is both functional and flexible, with three bedrooms, three full baths, and a half bath arranged across a two-story design that balances everyday livability with elevated entertaining. The main living areas unfold with a coastal-modern sensibility, wood flooring, crown molding, and expansive sliders that frame views of the pool, lanai, and canal beyond. The kitchen, finished in a soft seafoam palette, blends custom shaker cabinetry, quartz surfaces, and professional-grade KitchenAid appliances with a dedicated beverage station, creating a space that feels equally suited for quiet mornings or hosting at scale. A standout feature of the home is its full entertainment space; an expansive theater and bar lounge designed as a destination in itself. With a projector system, surround sound, custom wet bar, and multiple gathering zones, it introduces a layer of lifestyle rarely found in properties of this scale. A cylindrical tube elevator provides a striking architectural moment while connecting this space directly to the private primary suite above. Upstairs, the primary suite is positioned to take full advantage of the waterfront setting, with a private balcony overlooking the canal, an oversized walk-in closet, and a spa-like bath complete with a jetted soaking tub, dual vanities, and a glass-enclosed shower with dual heads. Outdoors, the experience is equally intentional. A resort-style saltwater pool and spa anchor multiple seating and entertaining areas, complemented by an outdoor kitchen and low-maintenance landscaping that keeps the focus on the water. What elevates 524 Hornblower beyond its physical attributes is its location within the broader context of Longboat Key. Deeded beach access provides a direct connection to the Gulf, while proximity to St. Armand's Circle and the St. Regis Longboat Key Resort places world-class dining, shopping, and amenities just minutes away. The result is a rare dual lifestyle, boating on one side, beach on the other, anchored by one of the island’s most established and desirable neighborhoods. At its core, this is a property defined by access: to water, to the Gulf, to the lifestyle that has long made Longboat Key one of Florida’s most enduring coastal addresses.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
3060 GRAND BAY BLVD #174, LONGBOAT KEY, FL 34228
$1,798,000144 Days on yellowkey MLS ID: R4910478
REDUCED by $141,000 (7.3%) on 05/17/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2550 Built: 1994Monthly Fee: $2,617 Tax: $17,500 (2024)Community: Grand Bay 1Spa: YesCondo
Taxes:$17,500
Elementary School: None
Remarks: PRICE POINT ADJUSTMENT ON HIGH FLOOR UNIT! Resort Living At It's Finest with this Grand Bay Condominium offers Privacy in the exclusive Bay Isles community. Grand Bay is situated directly on Bishops Point offering extensive Sarasota City views. Get swepted away by the dramatic unobstructed views of the city and expansive Sarasota Bay. The expansive floor to ceiling"Walls of Windows" with terraces on both the east and west sides of the building. Perfect sunrises and sunsets are the order the day ! The open floor plan from living room, to dining room, to den (can be easily converted into a 3rd bedroom) and the convenience of the kitchen all flow smoothly for entertaining and easy living. The den, kitchen, and guest bedroom all face west with access to the terrace for spectacular sunsets. The kitchen offers all of the latest modern conveniences with an oversized SubZero refrigerator/freezer, mini Perlick bottle refrigerator, Bosch dishwasher, Wolf triple oven with microwave, warming oven and Empava induction cooktop. This unit is sold fully furnished with high end quality names like Ethan Allen, Hancock & Moore and Italian leather. The master bedroom boasts panoramic views of the city and connects to the east terrace with plenty of space for sunbathing and nature watching. The marble master bath invites you to soak in the garden tub to relax the day away. Grand Bay Building 1 Caymen unit offers Total Privacy on the East and West Balconies with Glass railings for unobstructed viewing privacy! The en-suite guest bedroom is currently being used as an office and features its own grand views of the Longboat Key’s Harbourside golf course and the Gulf of Mexico beyond. Grand Bay is situated behind the Longboat Key Club gates and offers additional gated security at the building entrance for your peace of mind. Amenities for your enjoyment include two Har-Tru tennis courts, a state-of-the-art fitness center on the second floor of the Newly modernized Grand Bay clubhouse, two large heated pools and private beach access to the Newly modernized PRIVATE Bay Isles Beach Club directly on the Gulf of America. Grand Bay offers Electric Car Charging Stations. The Travertine stone floors are polished to perfection and is in pristine condition. This is resort style living, at its finest with the convenience of being located on Longboat key. Just minutes from St. Armand's world renowned shopping, restaurants and the cultural capital of Florida that is downtown Sarasota. Memories that will last a lifetime....All offers submitted via FAR-BAR contract form. Please use showing time button for all showings
Listing is courtesy of: LEN SCAVRON (908-304-5454)
Listing Agent: Len Scavron (908-304-5454)
3710 GULF OF MEXICO DR #F2, LONGBOAT KEY, FL 34228
$475,00084 Days on yellowkey MLS ID: A4681154
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 740 Built: 2026Monthly Fee: $290 Tax: $2,070 (2025)Community: Gulfshore Of Longboat KeyManufactured Home
Taxes:$2,070
Remarks: Island Living at Its Finest – Brand New Home on Longboat Key. Welcome to Gulfshore of Longboat, a highly desirable waterfront co-op community offering private beach access, boat docks, and sweeping views of the Gulf of Mexico and Sarasota Bay. This beautifully built 2-bedroom home combines modern efficiency with relaxed coastal living. An outdoor bathroom with a shower is a wonderful convenience for those enjoying the pool or boating. Step inside to an open, sun-filled floor plan featuring soaring ceilings with tray accents in both the living room and the primary bedroom, creating a bright, spacious atmosphere throughout. The kitchen is designed for everyday comfort and entertaining, complete with a center island, hardwood shaker cabinetry with soft-close doors and drawers, and a full stainless appliance package including refrigerator with ice and water, range, dishwasher, microwave, and garbage disposal. Built to current HUD hurricane standards and Energy Star certified, the home offers peace of mind with 2x6 construction, upgraded insulation, and low-E vinyl windows for year-round comfort and efficiency. Enjoy mornings at the private beach, afternoons at the heated pool, and evenings watching sunsets over the water. The community clubhouse hosts regular activities, making it easy to relax and connect with neighbors in a friendly coastal setting. Whether you’re looking for a winter retreat or full-time residence, this move-in-ready island home delivers comfort, security, and the lifestyle Longboat Key is known for. No pets (except for service animals or emotional support animals with appropriate paperwork) or Rentals permitted. Schedule your private showing today and start living the Gulf Coast dream.
Listing is courtesy of: WAGNER REALTY (941-751-0670)
Listing Agent: Marsha Winegarden (248-563-2820)
2367 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228
$985,000180 Days on yellowkey MLS ID: A4670055
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2219 Built: 1986Monthly Fee: $1,617 Tax: $11,977 (2024)Community: Harbour Oaks 2Villa
Taxes:$11,977
Remarks: NEW PRICE: Lives like a single family home! This 3 bedroom, 2 1/2 bath villa with over 2,200 sq.ft and an attached 2-car garage offers all the privacy and convenience of a private home and all the convenience of a maintenance free community. Located on #2 hole of the White Egret course on the Harbourside Golf Course in the Longboat Key Country Club. This home is in a secure gated community with only 42 villas in Harbour Circle with a community pool and spa and membership access to the deeded private beach club. This home boasts vaulted ceilings, multiple hurricane skylights, hurricane windows, sliders and front door, private atrium and new roof with trusses in 2025, coming completely furnished. Enjoy your morning coffee and dozens of magnificent sunsets on your large two level lanai. Enjoy a walk to Publix, CVS and several Banks close to your community. Only a short drive to Saint Armand's Circle and downtown Sarasota where you will find numerous options for shopping, dinning, theatres, ballet, opera and galleries.
Listing Agent: Sandra Endres (941-735-2527)
2800 HARBOURSIDE DR #E-08, LONGBOAT KEY, FL 34228
$250,00091 Days on yellowkey MLS ID: A4683624
Bed: Bath: 0.0 Built: 1985Monthly Fee: $405 Tax: $2,400 (2025)Community: Bay IslesDock-Rackominium
Taxes:$2,400
Remarks: access on the south side of the pier! A 60 ft. x 21 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club.. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted for approval prior to entering the marina. Max length of vessel allowed is 55 LOA, usable beam is 19 ft at the head of the slip.
3802 GULF OF MEXICO DR #A203, LONGBOAT KEY, FL 34228
$399,000239 Days on yellowkey MLS ID: A4667199
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1007 Built: 1970Monthly Fee: $1,347 Tax: $2,774 (2024)Community: Beach Harbor ClubCondo
Taxes:$2,774
Remarks: Super value on 2nd floor 2br/2ba condo in Beach Harbor Club. This beautifully maintained Gulf-to-bay community offers boat slips on the bay and private beach access on the Gulf side, as well as pool, clubhouse, gym and private beach access just accross the street! Just bring your bathing suit and flip flops as this two-bedroom and two-bath unit has been beautifully updated to include an all-new bright open kitchen with custom cabinetry, stone counters and high-end appliances, including a Fisher & Paykel fridge, a two-drawer Cafe dishwasher, and a Cafe two-oven, six-burner stove. Flooring throughout was updated with a light blond luxury vinyl plank. Both baths had updates including cabinetry and countertops found in the kitchen. The AC was replaced in 2024. This home also has a sweet view of the Gulf from the outdoor seating area in the front. Beach Harbor Club is an active and amenities-rich community with boat docks, a pool, a gym, private beach access, kayak storage, a ground-level storage closet for beach gear, a beautiful clubhouse and just upstairs from this unit is a wonderful rooftop deck for sunset viewing.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Holly Switow (941-735-3186)
1925 GULF OF MEXICO DR #G8-302, LONGBOAT KEY, FL 34228
$629,00071 Days on yellowkey MLS ID: A4686871
REDUCED by $20,000 (3.1%) on 05/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1257 Built: 1978Monthly Fee: $1,607 Tax: $6,897 (2025)Community: Seaplace ViSpa: YesCondo
Taxes:$6,897
Remarks: Experience the Best of Gulfside Living at Seaplace on Longboat Key! Welcome to this beautifully maintained 2-bedroom, 2-bath residence offering the perfect blend of comfort, style, and coastal charm. This light-filled unit features an updated kitchen with rich wood cabinetry, granite countertops, and ample storage—ideal for both everyday living and entertaining. The spacious primary suite offers a relaxing retreat with generous closet space and an en-suite bath, while the guest bedroom provides comfort and privacy for visitors. Both bathrooms are tastefully updated, and the open-concept living and dining areas flow seamlessly to the screened lanai. Step outside to your private lanai with hurricane impact screening, where you can enjoy tranquil views and refreshing Gulf breezes. The home is further enhanced with hurricane-impact windows, providing peace of mind and energy efficiency. Residents of Seaplace enjoy approximately ½ mile of pristine Gulf beach frontage and an exceptional array of amenities across 42 beautifully landscaped acres. Highlights include two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a fitness center, and a clubhouse with kitchen, library, and sauna. Additional features include a playground, grilling areas, on-site management, and a 24-hour staffed gatehouse. Whether you're seeking a full-time residence, seasonal retreat, or investment opportunity, this property offers a low-maintenance island lifestyle in one of Longboat Key’s most desirable communities. Enjoy breathtaking sunsets, beachside strolls, and resort-style living—schedule your private showing today!
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
2301 GULF OF MEXICO DR #43N, LONGBOAT KEY, FL 34228
$1,000,00077 Days on yellowkey MLS ID: A4686190
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $10,915 (2025)Community: Islander Club Of LongboatCondo
Taxes:$10,915
Remarks: One or more photo(s) has been virtually staged. Perfectly positioned in the sought-after Islander Club Condominium, this 2-bedroom, 2-bath residence offers commanding Gulf and beach views from the living room, dining room, and both bedrooms. Expansive windows frame the sparkling waters of the Gulf of Mexico, creating a breathtaking backdrop for everyday living while showcasing spectacular sunset skies each evening. Situated front and center on the 4th floor, the residence enjoys one of the most desirable vantage points in the building, elevated enough for panoramic shoreline views yet close enough to feel immersed in the beauty and rhythm of the beach below. Competitively priced, the condominium presents a rare opportunity for the next owner to create their own vision of coastal living. Whether designing a sophisticated modern retreat or a relaxed island escape, the residence offers a blank canvas ready to be transformed to your personal taste and style—truly a chance to make it your own. Residents of the Islander Club enjoy a collection of resort-style amenities including direct access to the pristine Gulf Beach, a beachfront Olympic size swimming pool, tennis courts, fitness center, clubhouse, library, and beautifully landscaped tropical grounds. Located on the coveted south end of Longboat Key, the community offers convenient access to Publix, the world-class shopping and dining of St. Armands Circle as well as the vibrant arts, cultural venues, and waterfront restaurants of downtown Sarasota. Go ahead – Make it your own and have it your way!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Steve Nursey (941-356-7010)
2185 GULF OF MEXICO DR #243, LONGBOAT KEY, FL 34228
$2,300,000371 Days on yellowkey MLS ID: A4651046
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2445 Built: 1996 Tax: $27,759 (2024)Community: Villa Di Lancia Ph 1Spa: YesCondo
Taxes:$27,759
Remarks: Experience the pinnacle of island living in this exquisite 3-bedroom, 3-bath penthouse at Villa di Lancia, a prestigious Gulf-front enclave on Longboat Key. One of only 38 residences in this gated, resort-style community, this rare offering boasts a 195 sq ft balcony with sweeping Gulf views—plus glimpses of Sarasota Bay and the downtown skyline. Meticulously maintained by the original owner and offered turnkey furnished, pride of ownership is evident throughout, and the timeless layout invites your vision for contemporary updates. The views from the main living area and primary suite are simply breathtaking, and there is a large covered portion of the balcony to provide shade if needed. The unit has a natural gas fireplace and cooktop, solid core doors, wood cabinetry and stone counters throughout, and a ceiling height of 9’ 9”. The second bedroom has a walk in closet and ensuite bathroom, plantation shutters, and expansive views across the golf course to Sarasota Bay. The third bedroom is currently used as a den, but could be easily restored to a third bedroom. It also has golf course and bay views. The kitchen is well designed with shaker style cabinetry, granite countertops, a central island with pull out drawers and a planning desk, but there is good potential to expand or reimagine as desired. Villa di Lancia residents enjoy direct beach access, lushly landscaped grounds, a staffed gatehouse, and an impressive suite of amenities: har-tru tennis courts (also striped for pickleball), a fitness center, sauna, resort-style pool, hot tub, and elegant clubhouse for social gatherings. Onsite property management, maintenance, and concierge-level services ensure carefree living. Just minutes from the world-class shopping and dining of St. Armands Circle and the vibrant arts scene of Downtown Sarasota, Villa di Lancia offers the perfect blend of privacy, luxury, and convenience. This unit has one assigned garage parking space which is deep enough to fit two vehicles and a private storage unit. EV charging station on site.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Bev Murray (941-724-4995)
350 GULF OF MEXICO DR #234, LONGBOAT KEY, FL 34228
$749,000133 Days on yellowkey MLS ID: A4678529
1 Days Off yellowkey (back on 5/14/2026)
REDUCED by $150,000 (16.7%) on 04/24/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2513 Built: 1992 Tax: $10,107 (2025)Community: Tangerine Bay ClubSpa: YesCondo
Taxes:$10,107
Remarks: One or more photo(s) has been virtually staged. Set amid the lush, manicured grounds of Tangerine Bay, this exceptional two-story penthouse residence offers a rare blend of architectural volume, natural light, and water views. Mature tropical landscaping, tranquil lagoons, and resort-style amenities create a serene, park-like environment that feels both private and welcoming. Two terraces highlight scenic views and offer the option of installing a gas grill. Inside, soaring two-story ceilings define the main living area, creating an airy, light-filled atmosphere enhanced by expansive windows that frame picturesque views of the lagoon, resort-style pool w/ waterfall features, tropical plantings and the waters of Sarasota Bay and distant city skyline. The open living and dining spaces are ideal for both relaxed everyday living and entertaining, anchored by a fireplace and generous wall space for art. From the entry patio, unexpected Bay and city views provide a striking first impression and a unique urban-meets-coastal backdrop. The residence features three full bedrooms and three and a half baths. The upper-level retreat with its full bath has a terrace with elevated views across the natural preserve toward the city. This home presents a true blank canvas, thoughtfully priced to allow the new owner to reimagine and transform it into their own vision of refined coastal living. A deeded, private two-car garage adds exceptional convenience and value—an uncommon and highly desirable feature. Located on the coveted south end of Longboat Key, Tangerine Bay Club is a gated, pet-friendly community close to Lido Beach, dining and boutique shopping on St. Armands Circle, and the cultural, dining, and arts scene of downtown Sarasota. Optional Bay Isles Beach Club membership is available, providing exclusive access to a private, gated four-acre Gulf of Mexico beach facility, reserved for a select group of members—ideal for beach gatherings, sunset celebrations, and effortless days by the sea. An outstanding opportunity to embrace the Florida lifestyle in one of Longboat Key’s most desirable bayfront communities.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
803 BAYPORT WAY #803, LONGBOAT KEY, FL 34228
$775,00073 Days on yellowkey MLS ID: A4686552
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1456 Built: 1981 Tax: $6,376 (2025)Community: Bayport Bch & Ten Ph ECondo
Taxes:$6,376
Remarks: Under contract-accepting backup offers. Welcome to the true tropical oasis of Bayport Beach & Tennis Club, a Longboat Key Gulf to Bay community. Bayport was designed by Tim Siebert, one of the founding architects of the renowned Sarasota School of Architecture and is recognized for its award-winning, timeless design. Bayport offers 27 lushly landscaped acres with 1,200 feet of private beach. This tastefully renovated second-floor unit offers two expansive bedrooms and two beautiful bathrooms and comes fully turn-key. This unit was curated with attention to detail and functionality in mind. The kitchen offers plenty of storage, stainless steel appliances, quartz countertops and beautiful accent details. Enjoy three patios that allow for great indoor/outdoor living. Fully equipped with Hurricane impact doors and windows. One under building parking space included, along with a locked storage closet - perfect for bikes and beach gear. When not at the beach, enjoy the meticulously kept nature trails, landscaped grounds and wildlife. Just steps away from the well appointed clubhouse is equipped with a Junior-Olympic sized heated pool, four har-tru tennis courts, a fitness center and more. In addition, Bayport residents are proud of their active social and recreational calendar. Water enthusiasts can utilize the secluded fishing pier that stretches out onto Sarasota Bay; to fish, watch the sunrise, the Manatees swim or the Egrets wading among the mangrove trees. Residents also benefit from conveniently located on-site paddle board and kayak launch and storage areas. Bayport residents enjoy an array of restaurants locally, and the convenience of a nearby supermarket, pharmacy and boutique shops. Recreational enthusiasts also benefit from the nearby Bayfront Park which offers a popular pickle-ball program, dog park and other bayside activities. The nearby Longboat Key Club offers private access to championship waterfront golf, extensive leisure activities and boating facilities. Within minutes, one can access the famous St Armand's Circle with its exceptional shopping and dining amenities. From there, cross the iconic Ringling Bridge to downtown Sarasota, which is well known for world-class theater, culture and dining.
Listing Agent: Alexis Smith-Frady (352-225-1724)
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