Location: Longboat Key
Do Not Show Listings
2295 GULF OF MEXICO DR #54S, LONGBOAT KEY, FL 34228
$899,000119 Days on yellowkey MLS ID: A4683112
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $7,576 (2025)Community: Islander Club Of LongboatCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,576
Elementary School: Southside Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Welcome to The Islander Club — your turnkey getaway awaits! Step into coastal living with this beautifully updated residence offering effortless style and year-round relaxation. The open, sun-filled layout features tasteful luxury finishes and seamless access to a 38-foot terrace, perfect for unwinding after a day at the beach. Unit 54S has been thoughtfully upgraded throughout, showcasing wood flooring, an updated kitchen with stainless steel appliances, refreshed bathrooms, and unique architectural details that add character and charm. The sunlit primary bedroom includes an ensuite bathroom, a large walk-in closet, and a cozy seating area ideal for reading or enjoying your morning coffee. The spacious second bedroom welcomes guests with terrace access and a generous closet for added storage. The Islander Club’s resort-style amenities include a private 400' beachfront, heated pool, brand-new fitness center, two new sauna rooms, a Har-Tru™ tennis court, two pickleball courts and on-site management for true lock-and-leave convenience. The Islander Club has recently completed an extensive series of capital improvements that elevate both the structural integrity and the everyday experience of the community. Enhancements include exterior stucco repairs and balcony waterproofing, new roofs on the carports, clubhouse, and both residential towers, and modernized pool facilities with new resurfacing, tile, and equipment. Additional upgrades such as refreshed landscaping and lighting, hurricane-rated windows and doors, and a fully renovated fitness center further enhance the appeal and long-term value of the property. Whether you’re seeking a seasonal retreat or a full-time coastal home, this move-in-ready gem delivers the best of island living and peace of mind.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Julie Lojacono Mackie (773-704-1438)
775 LONGBOAT CLUB RD #807, LONGBOAT KEY, FL 34228
$1,995,000259 Days on yellowkey MLS ID: A4667077
0 Days Off yellowkey (back on 6/20/2026)
REDUCED by $300,000 (13.1%) on 06/09/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1842 Built: 1984 Tax: $10,487 (2024)Community: Beaches Of Longboat Key Ph-1Condo
Taxes:$10,487
High School: Booker High
Tax Year: 2024
Middle School: Pine View School
Remarks: Welcome to Beaches of Longboat Key - Unit 807 From a morning stroll on the beach to twilight cocktails on your wrap around balcony watching the glittering lights of Sarasota over the bay, you will experience beauty all around. Longboat Key, a jewel in the crown of the Sarasota Coastline, has so much to share. This elegantly appointed home will not disappoint. Custom finishes are abundant throughout the 1,842 sq ft condominium, not to mention the breath-taking views from the over 300 sq ft wrap-around balcony. This gracious home offers generous living space, with sweeping views from every window. Upon entering 807, you are greeted to stunning engineered Brazilian Cherry Hardwood flooring that continues throughout the home. A Reme Halo Air Purification System keeps the air fresh and clean. All windows and sliders are Impact. Beautiful crown molding throughout. The custom kitchen created by Campbell’s Cabinetry, Quartzite countertops, SubZero 42” Side by Side Refrigerator Freezer, Wolf Steam Convection Oven, GE Monogram Induction Cooktop, Zephyr PISA range hood. Bosch Dishwasher, Blanco Silgranite Sink, Hansgrohe Faucet. Custom cabinetry can be found throughout this beautiful residence. Primary Bedroom Suite offers views, comfort and luxury. Two bedrooms, each with well-designed baths, custom touches are found everywhere. There is one assigned parking space assigned to the unit on the upper level, and there is ample parking on the lower level for your second vehicle. Beaches is a great community offering you every convenience: 24-hour Concierge, Heated pool & Spa, Fitness Room, Tennis Courts, Social Room, Catering Kitchen, direct Walkway access to the Beach and a Basement Storage area. This proactive community is hard at work completing several important and vital projects: Stack Pipelining throughout the building, Roof Replacement will take place later this year and Temporary Wind/Surge Barriers are being purchased to protect the main floor of the building. Morning, noon and night, there is always something wonderful to experience at Beaches on beautiful Longboat Key. Schedule you showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: David Stasney (941-705-8464)
3806 GULF OF MEXICO DR #C209, LONGBOAT KEY, FL 34228
$335,00036 Days on yellowkey MLS ID: A4693850
2 Days Off yellowkey (back on 6/20/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1046 Built: 1970Monthly Fee: $1,346 Tax: $2,934 (2025)Community: Beach Harbor ClubCondo
Taxes:$2,934
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Discover Your Slice of Paradise! This charming turnkey 2-bedroom, 2-bath condo is perfectly positioned between the Gulf of Mexico and Sarasota Bay, offering breathtaking sunrise and sunset views. Enjoy deeded beach access complete with lounge chairs, picnic tables, charcoal grills, and outdoor showers. On the bayside, recent upgrades include a new dock with first-come boat slips, community kayaks, an electric kayak launch, and a fishing pier with a cleaning station. Host a BBQ at the tiki hut or relax by the heated pool featuring gas grills, indoor restrooms, and an outdoor shower. The newly renovated clubhouse offers an upgraded fitness center, card room, large bar, full kitchen, and plenty of gathering space for entertaining.During season, this vibrant and friendly community comes alive with Wednesday night happy hours and festive celebrations including St. Patrick’s Day, Mardi Gras, Cinco de Mayo, and more.
Listing is courtesy of: FLORIDA GALLERY REAL ESTATE (941-315-6678)
Listing Agent: Kathleen Magnus (941-281-5539)
4350 CHATHAM DR #Unit E-208, LONGBOAT KEY, FL 34228
$640,000210 Days on yellowkey MLS ID: A4672221
REDUCED by $35,000 (5.2%) on 06/17/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1316 Built: 1969 Tax: $6,535 (2025)Community: Longboat HarbourCondo
Taxes:$6,535
Remarks: One or more photo(s) has been virtually staged. NEW PRICE IMPROVEMENT! REDUCED $35,000! NEWLY REMODELED • COASTAL LUXURY RESIDENCE Longboat Harbour • Building E #208 | Corner End Unit • Bay & Harbour Views. CLOSEST BUILDING TO A SHORT WALK ACCROSS THE STREET WITH A PRIVATE DEEDED GULF BEACH ACCESS WITH PAVILION, RESTROOMS AND SHOWERS TOTALLY REMODELED FROM FLOOR TO CEILING second-floor corner residence in the highly sought-after Longboat Harbour Community. This light-filled home captures sweeping views of Sarasota Bay and Longboat Harbour. This spacious two-bedroom, two-bath retreat has been transformed with exceptional attention to detail. Elevated finishes, a soothing coastal palette, and an airy open layout blend modern luxury with effortless livability. Corner units of this caliber are rarely available. From the two bedrooms, you step out to the exceptionally Large Lanai with floor to ceiling sliding glass doors. A SHOWCASE KITCHEN WITH TWO SUNLIT WINDOWS AND WATER VIEWS Elegant, functional, and beautifully appointed: • Frigidaire Professional stainless steel appliances • Gleaming quartz countertops • 9-inch deep sink • Pull-out cabinet shelving • Pantry closet • Designer tile backsplash • Large Eat-In Kitchen with water views & sunsets • Instant hot-water. LUXURIOUS PRIMARY SUITE An elevated retreat professionally designed for comfort and relaxation • Private ensuite bath • Custom California Closet walk-in wardrobe • Built-in desk feature • Remote-controlled luxury solar shades. RESORT-INSPIRED AMENITIES Longboat Harbour offers a lifestyle unmatched on the Gulf Coast: • Designated covered parking spot conveniently located • Personal storage space on the third floor • Private deeded Gulf beach access with pavilion, restrooms & shower • Four sparkling pools • Fitness center & sauna • Tennis & pickleball courts • Billiards room, library & meeting rooms • Picnic areas with grills • Putting green • Fishing pier • Affordable resident-only boat dockage • KAYAK LAUNCH and KAYAK WHICH SELLER WILL BE GIFTING TO THE BUYER. Enjoy effortless waterfront living and endless ways to explore the natural beauty of Longboat Key. PROPERTY ENHANCEMENTS & UPDATES: Thoughtfully improved for comfort, reliability, and peace of mind: • NO HURRICANE DAMAGE OR FLOODING • Bosch Washer & Dryer • Newer AC: 12/5/21 • Newer Hot Water Heater: 3/3/17 • New roofs throughout the community • Electrical and plumbing systems updated. A BEAUTIFULLY RENOVATED INTERIOR THAT CREATES THE ULTIMATE COASTAL LIFESTYLE/ THE MONTHLY HOA FEE INCLUDES HAZARD, HURRICANE AND FLOOD INSURANCE/ RESERVES HAVE BEEN FULLY FUNDED
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Billie Chipain (941-587-8556)
605 SUTTON PL #201, LONGBOAT KEY, FL 34228
$619,00091 Days on yellowkey MLS ID: A4687586
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1148 Built: 1973 Tax: $6,756 (2025)Community: Sutton PlaceCondo
Taxes:$6,756
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: This is the one you have been waiting for!! INCREDIBLE UNOBSTRUCTED BAY VIEWS & BREATHTAKING SUNRISES from this light-filled CORNER unit in the beach-to-bay community of Sutton Place. Enjoy stunning vistas from nearly every room through impact windows and doors! Meticulously maintained and beautifully renovated, this spacious two-bedroom, two-bath coastal retreat is truly exceptional. The thoughtfully designed open concept chef’s kitchen with premium cabinetry, plentiful storage, and Cambria quartz countertops seamlessly connects to the expansive living area through a custom dining island with wraparound seating. Plantation shutters throughout the kitchen and living area add to the coastal island feel. The enclosed lanai, featuring walls of glass that span along the rear of the unit, provides an ideal setting for morning coffee, evening relaxation, remote work, or accommodating additional guests. The spacious primary and secondary bedrooms provide exceptional views, each with direct access to the lanai through impact-rated sliding doors. The serene primary bedroom boasts a generous walk-in closet fitted with a custom organizer and an elegantly renovated bathroom with a walk-in shower, complete with a linen closet. The secondary bedroom offers ample storage with a double closet, also fitted with custom organizers. The adjacent guest bath has been tastefully renovated. Parking is easy with a covered, assigned space in a convenient location, plus plenty of overflow and guest parking. While the stairs are easily accessible; there is also an elevator for added convenience. The in-building storage unit provides extra space for any additional storage needs. Sutton Place offers a wide range of amenities, including two heated swimming pools, a community clubhouse, marina facilities with boat slips (current wait list but only $300 annually!!), kayak storage equipped with electric launch, a fish cleaning station, designated grilling areas, car wash stations, and deeded beach access with private beach pavilion featuring storage lockers, showers, and restrooms. The community successfully endured the recent storms, experiencing minimal overall damage and no impact to any individual units. With its exceptional location, unmatched views, and wonderful amenities, this property is an opportunity not to be missed! Schedule your private showing today!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Melissa Rodocker (703-969-2345)
605 SUTTON PL #102, LONGBOAT KEY, FL 34228
$485,000141 Days on yellowkey MLS ID: A4681310
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 992 Built: 1973Monthly Fee: $1,642 Tax: $6,934 (2024)Community: Sutton PlaceCondo
Taxes:$6,934
Remarks: Sutton Place is perfectly situated on the tropical grounds of the Longboat Harbour Community. The two-bedroom, two-bathroom unit features beautiful views of the Sarasota Bay, spacious living area, full-size kitchen with stainless steel appliances and granite countertops, dining area and 3 flat-screen TV’s. If the amenities on the interior of the condo aren’t enough – the community of Sutton Place boasts two heated swimming pools, fishing pier and game room, complete with billiards and ping-pong; along with a fitness center and clubhouse. Deeded beach access is located directly across the street.
Listing is courtesy of: SVN COMMERCIAL ADVISORY GROUP (941-387-1200)
Listing Agent: Larry Starr (941-914-6869)
4350 CHATHAM DR #105, LONGBOAT KEY, FL 34228
$310,0008 Days on yellowkey MLS ID: A4697241
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 747 Built: 1969Monthly Fee: $1,147 Tax: $1,457 (2025)Community: Longboat HarbourCondo
Taxes:$1,457
Remarks: Exceptional opportunity to own a beautifully furnished waterfront residence in a gated, amenity-rich boating community. This one-bedroom unit features hurricane-impact sliding glass doors and windows, allowing abundant natural light while providing peace of mind. Enjoy waterfront living with access to a private beach located at 4415 Gulf of Mexico Drive, complete with gated parking, indoor facilities, and beachside amenities. Residents have access to an impressive array of community features, including four heated swimming pools, a spacious fitness center, pickleball courts, tennis courts, kayak and bicycle storage, and a vibrant boating community with first-come, first-served boat slips. Additional amenities include a banquet hall and numerous social and recreational opportunities. Whether you're seeking a full-time residence, seasonal retreat, or investment property, this waterfront gem offers the perfect combination of coastal lifestyle, convenience, and value.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Malihe Karimi (941-376-5099)
4234 GULF OF MEXICO DR #M1, LONGBOAT KEY, FL 34228
$649,0007 Days on yellowkey MLS ID: A4696419
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1150 Built: 1973 Tax: $2,383 (2025)Community: Pelican Harbour & Beach ClubCondo
Taxes:$2,383
Remarks: It really is all about the location- and of course the view! Situated on gorgeous Sarasota Bay, this lovely two bedroom, two bath first floor condo offers a walk out to the sculpted grounds of Pelican Harbour and great water views of the bay from your private screened lanai. Recently professionally renovated in tasteful coastal chic, this beautifully updated condo boasts new hurricane impact windows, designer Samsung kitchen appliances, ceramic tile flooring, an island kitchen with granite countertops and white shaker wood cabinets, ceiling fans, plantation shutters, closet built-ins, washer and dryer, and new window treatments. New AC (2025). Pelican Harbour and Beach Club is a pet friendly community and offers world class amenities including private gulf beach access, a heated resort-style pool, kayak and bike storage, day dock, tennis, and pickleball. This well-maintained community has successfully completed its milestone inspection, has fully-funded reserves, and has no special assessments. Association fees include building maintenance, landscaping, building insurance, cable, water, sewer, trash, professional management, and pest control. The community has covered reserved carports, new roofs and a composite day dock that is perfect to enjoy a cup of coffee while catching those stunning Florida sunrises over water. Pelican Harbour is centrally located mid key, with convenient access to St. Armands Circle, Bayfront Park, Publix, and fine dining at a number of outstanding restaurants. Your unique opportunity to enjoy the Longboat Key lifestyle awaits!
Listing Agent: John Thorson, Pa (941-914-1366)
1561 GULF OF MEXICO DR #403, LONGBOAT KEY, FL 34228
$13,000,000592 Days on yellowkey MLS ID: A4627926
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4187 Built: 2024 Tax: $81,320 (2025)Community: St. Regis Longboat KeyCondo
Taxes:$81,320
Remarks: Experience unparalleled luxury with breathtaking views of the Gulf of Mexico in the Armand Building. This exceptional residence features an open-concept floorplan designed for entertaining, complete with floor-to-ceiling glass doors that lead to an expansive terrace outfitted with a built-in gas grill, perfect for seamless indoor-outdoor living. Ideal for multi-generational gatherings, the clubroom serves as a fantastic bonus space, featuring a wet bar equipped with an ice maker, bar sink, and wine fridge. The gourmet kitchen is a chef’s dream, showcasing top-of-the-line Wolf and Sub-Zero appliances, including a 6-burner gas cooktop, double ovens, and an integrated cabinet front side-by-side refrigerator/freezer. A semi-private elevator with keyless entry transports you directly from your private two-car garage to your residence. The owner’s suite offers a spacious walk-in closet, a luxurious soaking tub, a frameless walk-in shower, and dual vanities with separate water closets. Designed with technology-ready infrastructure, this home allows for easy customization of your automation preferences. Located within the first branded residential community and ultra-luxe 5-star resort hotel on the Gulf, The Residences at The St. Regis Longboat Key blend legendary service with the allure of a serene seaside retreat. Spanning over 17 acres with 800 feet of direct beachfront, residents can indulge in unparalleled amenities, including signature St. Regis Butler and Concierge services, a world-renowned spa, in-residence dining, a resident-only pool and spa, a private clubhouse, a fitness center, and beachside cabanas. Discover a life of luxury and leisure at The Residences at The St. Regis Longboat Key—where every day feels like a getaway. The owner will consider a lease purchase with acceptable terms on this residence.
Listing Agent: Michael Moulton (941-928-3559)
3804 GULF OF MEXICO DR #B204, LONGBOAT KEY, FL 34228
$339,00015 Days on yellowkey MLS ID: A4696842
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 761 Built: 1970 Tax: $1,343 (2025)Community: Beach Harbor ClubCondo
Taxes:$1,343
Remarks: Welcome to coastal living at its finest in this beautifully renovated 1-bedroom, 1-bath condo at Beach Harbor Club on coveted Longboat Key. Perfectly positioned adjacent to the beach, this second-story retreat offers a peek-a-boo view of the sparkling Gulf and 761 square feet of stylish, light-filled comfort. Step inside to discover a fully updated interior featuring impact windows, a new AC system, and modern finishes throughout. Every detail has been thoughtfully considered to deliver effortless island living. The building offers convenient elevator access, plus a wealth of amenities designed for relaxation and recreation. This vibrant community stretches from beach to bay, granting you deeded beach access and a rooftop deck where unforgettable sunsets await. Cool off in the heated pool, unwind at the tiki bar, or gather with neighbors in the clubhouse. Outdoor enthusiasts will love the kayak and canoe launch, while boat slips are available first-come, first-serve for $700/year. Additional perks include a fitness center, laundry facility, bike storage, storage locker, wood shop, and on-site management. Condo fees thoughtfully cover TV, internet, and water for added peace of mind. Beyond your doorstep, indulge in the best of the region. Savor waterfront dining at Dry Dock Waterfront Grill, shop at nearby Publix, or explore the boutiques of St. Armands Circle. Anna Maria Island's charm is just a short drive away. Discover your slice of paradise—schedule your private showing today and embrace the Longboat Key lifestyle.
Listing is courtesy of: STERLING REALTY (941-379-5810)
Listing Agent: Shaun Cumston (941-737-3539)
1930 HARBOURSIDE DR #122, LONGBOAT KEY, FL 34228
$549,00052 Days on yellowkey MLS ID: A4692494
REDUCED by $10,000 (1.8%) on 06/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1192 Built: 1982 Tax: $6,584 (2025)Community: Fairway Bay 1Spa: YesCondo
Taxes:$6,584
Remarks: Welcome to your waterfront retreat in the highly sought-after Fairway Bay community, where relaxed coastal living meets thoughtful design and modern comfort. This beautifully renovated 2-bedroom, 2-bath condominium offers nearly 1,200 square feet of light-filled interior space, along with sweeping views of Sarasota Bay and the downtown skyline that create a stunning and ever-changing backdrop throughout the day. Fully updated in 2020 and professionally curated by an interior designer, the residence showcases a refined yet inviting aesthetic. Inside, the open-concept layout is enhanced by warm, driftwood-inspired luxury vinyl plank flooring and an abundance of natural light. The living and dining areas flow effortlessly together, while expansive pocketing sliders open wide to a private balcony, creating a seamless indoor-outdoor experience ideal for both quiet mornings and evening entertaining. From this vantage point, you can take in tranquil water views, coastal breezes, and vibrant sunsets that define the Longboat Key lifestyle. The galley-style kitchen is both stylish and functional, featuring quartz countertops, crisp Ivory soft-close cabinetry, New AC 2025, New Water Heater 2025, New Washer and Dryer 2025, stainless steel appliances installed in 2020, and a peninsula with seating that invites casual dining and conversation. The design balances clean lines with timeless finishes, making it equally suited for everyday living and hosting guests. The spacious primary suite serves as a private sanctuary, offering generous proportions, beautiful bay views, and direct access to the peaceful ambiance of the home. The en-suite bath is thoughtfully appointed with dual vanities, elegant lighting, and a walk-in tiled shower, creating a spa-like atmosphere. The guest bedroom and accompanying bath are equally well-designed, providing comfort and privacy for visitors while maintaining the home’s cohesive style. Additional features include plantation shutters on all windows and sliders, a private exterior entrance that enhances both convenience and privacy, a welcoming balcony seating area, and professionally landscaped surroundings that add to the property’s curb appeal. Important updates such as a new air conditioning system and water heater provide peace of mind, making this a truly move-in-ready opportunity. Fairway Bay, located within the desirable Bay Isles community, offers a lifestyle rich in amenities and natural beauty. Residents enjoy gated entry with 24-hour guard service, beautifully maintained grounds, resort-style pools, a clubhouse, fitness center, and tennis courts. Scenic walking and biking paths wind along the bay, while a kayak and paddleboard launch provides easy access to the water for outdoor enthusiasts. Ownership also includes exclusive access to a private beach club on the Gulf of Mexico, offering the rare advantage of experiencing both serene bayfront living and pristine Gulf beaches. Ideally situated near the renowned The St. Regis Longboat Key Resort, this residence is just moments from exceptional dining, shopping, and leisure experiences, further enhancing its appeal as both a full-time residence and seasonal escape. This is more than just a condominium—it is an opportunity to embrace the relaxed elegance, natural beauty, and effortless lifestyle that make Longboat Key one of Florida’s most coveted coastal destinations.
Listing Agent: David Leventhal (941-518-7694)
3040 GRAND BAY BLVD #234, LONGBOAT KEY, FL 34228
$1,150,000191 Days on yellowkey MLS ID: A4675109
0 Days Off yellowkey (back on 6/19/2026)
REDUCED by $100,000 (8.0%) on 05/06/2026
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2550 Built: 1996 Tax: $8,854 (2024)Community: Grand Bay 2Spa: YesCondo
Taxes:$8,854
Remarks: Under contract-accepting backup offers. Arrive by private elevator into this TURNKEY FURNISHED 2BR + den, 3.5BA residence offering 2,550 sq. ft. in Grand Bay. Wood floors run throughout the main living areas, leading to floor-to-ceiling sliders with views of the Harbourside Golf Course and Sarasota Bay. The covered terrace extends the living space and is well suited for enjoying daylight and coastal breezes. The living and dining areas are well proportioned for everyday living and entertaining, with a tray ceiling in the dining room. A den with custom built-ins is currently used as an office and sitting area and offers flexibility as a potential third bedroom. The kitchen features white cabinetry, stone countertops, tile backsplash and ample counter space, along with an eat-in area that opens to the outdoor living area. The primary suite enjoys floor-to-ceiling glass and a bath with a walk-in glass shower, soaking tub, distinctive tilework and separate water closets. The guest bedroom offers quiet community views. A powder bath and an in-residence laundry room add convenience. Grand Bay amenities include a staffed lobby, clubhouse, two pools and spas, fitness center with saunas and Har-Tru tennis courts. Bay Isles privileges include walking paths and membership to the private Bay Isles Beach Club with gated Gulf-front access on Longboat Key, parking, restrooms and shaded picnic areas. Optional membership to the Longboat Key Club provides access to championship golf courses, private beach club, marina, tennis facilities, fitness center, dining venues and a full-service spa.
Listing Agent: Bruce Myer (941-376-5311)
455 LONGBOAT CLUB RD #402, LONGBOAT KEY, FL 34228
$2,095,00086 Days on yellowkey MLS ID: A4686984
REDUCED by $100,000 (4.6%) on 05/04/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2410 Built: 1990 Tax: $18,228 (2025)Community: PierreSpa: YesCondo
Taxes:$18,228
Remarks: Gulf-front living takes on a refined sense of scale in this beautifully renovated, truly move-in-ready residence at The Pierre, where every detail is already in place for effortless coastal living. Located behind the gates of the Longboat Key Club, this intimate building of just 66 residences provides privacy, security and resort style amenities. The home features more than 2,400 sq. ft. of thoughtfully updated space that blends comfort, style, and quiet sophistication A full wall of glass showcases the property’s coveted southwest exposure, filling the interiors with natural light and framing stunning Gulf of Mexico sunsets each evening. With this ideal orientation, you enjoy uninterrupted views without the need for shutters or heavy blinds. Inside, diagonal tile flooring, high ceilings, and elegant millwork create an immediate sense of openness. The great room flows seamlessly into the dining area and the reimagined kitchen, designed with black stone countertops, off-white cabinetry with glass accents, high-end appliances, and a breakfast bar. A slider opens to the terrace, enhancing the home’s indoor-outdoor connection. A private office with double-glass doors provides a quiet, flexible workspace. The serene primary suite offers terrace access, a breathtaking view, and a spacious bath with dual water closets and a distinctive circular glass-enclosed shower. Guest accommodation is inviting, and an in-residence laundry room adds everyday convenience. Residents of The Pierre on Longboat Key enjoy concierge service, under-building parking, 24-hour security, a fitness center, three guest suites, one of which is a full 2-bedroom apartment, a heated pool and spa, Har-Tru tennis courts, shuffleboard, and private beach access. Membership opportunities at the Longboat Key Club offer championship golf and fine dining, all within minutes of St. Armands Circle and Sarasota’s vibrant downtown.
1211 GULF OF MEXICO DR #609, LONGBOAT KEY, FL 34228
$1,395,00015 Days on yellowkey MLS ID: A4696671
2 Days Off yellowkey (back on 6/15/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1827 Built: 1985 Tax: $14,266 (2025)Community: PromenadeSpa: YesCondo
Taxes:$14,266
Remarks: From sunrises over Sarasota Bay to breathtaking sunsets across the Gulf of Mexico, this sixth-floor residence at Promenade captures the panoramic water views that define Longboat Key living. Positioned along the sought-after southern end of the island, this beautifully maintained two-bedroom residence spans more than 1,800 square feet (the largest of the two-bedroom layouts in the community) and enjoys sweeping vistas of turquoise Gulf waters, Sarasota Bay, and the resort-style grounds below. An extended foyer entry welcomes you into the open layout designed to maximize both natural light and water views. Walls of glass (equipped with storm shutters) frame the Gulf beyond while seamlessly connecting the living and dining areas to the wraparound terrace. Contemporary finishes, elegant flooring, and a neutral palette create a refined yet comfortable atmosphere throughout. The renovated kitchen is thoughtfully designed for both everyday living and entertaining, featuring stone countertops, shaker-style cabinetry, stainless steel appliances, generous storage, and an adjacent breakfast area surrounded by Gulf windows that showcase sparkling beach views. Whether preparing a casual meal or hosting guests, the kitchen remains connected to the main living spaces while offering spectacular scenery from nearly every angle. Privately situated within the split-bedroom floor plan, the primary suite serves as a peaceful retreat with Gulf views, terrace access, dual walk-in closets, and a spacious en-suite bath featuring dual vanities, a soaking tub, separate shower, and private water closet. The guest suite offers its own walk-in closet and en-suite bath, providing comfort and privacy for visiting family and friends. Meticulously maintained and move-in ready, the residence also includes a dedicated laundry room, under-building parking, and private storage. The Promenade is one of Longboat Key's premier Gulf-front communities, offering residents a full-service lifestyle with a 24-hour manned guard gate, concierge services, on-site management, secure lobby, fitness facilities, social rooms, four Har-Tru tennis courts, Gulf-front sundeck, oversized heated swimming pool and spa, and a private boardwalk leading directly to the beach. Residents enjoy the convenience of resort-style amenities paired with attentive service and beautifully maintained grounds. Ideally located near the Longboat Key Club's golf, tennis, and marina facilities, The Promenade places you just minutes from waterfront dining, boutique shopping, and the renowned attractions of St. Armands Circle. Downtown Sarasota's vibrant cultural scene—including The Ringling, Sarasota Opera, Selby Gardens, art galleries, theaters, and acclaimed restaurants—is only a short drive away. This exceptional residence offers the perfect opportunity to enjoy Gulf-front living, panoramic water views, and the very best of Sarasota's coastal lifestyle.
Listing Agent: Roger Pettingell (941-387-1840)
100 SANDS POINT RD #225, LONGBOAT KEY, FL 34228
$899,00041 Days on yellowkey MLS ID: A4693834
0 Days Off yellowkey (back on 6/18/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1492 Built: 1966 Tax: $3,929 (2025)Community: Sands PointCondo
Taxes:$3,929
Remarks: Under contract-accepting backup offers. BACK ON THE MARKET with a New Price and Turn Key! Welcome to your slice of paradise, where coastal living reaches new heights of sophistication, and nestled inside the gates of the Longboat Key Club. This gorgeous 1492 sq. ft. water front residence underwent a total transformation in 2023, and the results are nothing short of spectacular. Step inside this bright second floor residence and discover a two bedroom and two baths, with a view that feels serene, luxurious, and unmistakably coastal. This condo comes with a view of the private marina tucked away in a quiet cove, where you can enjoy watching the dolphins at play. Towering palm trees frame the scene beautifully, with the curved waterfront drive adds a resort-style elegance to this one-of-a-kind property. This kitchen has a bright, modern, upscale feel with a clean coastal-inspired design. White shake-style cabinetry with sleek brushed nickel handles, extending all the way to the ceiling for extra storage. Exotic granite counters, matched with a sleek white Carrara marble back splash. Stainless steel appliances, and a deep undermount sink with a tall industrial-style spring faucet. The expansive great room steals the show, with a dramatic wall of windows, open concept and LVP flooring thru out. Both bathrooms feature quartz counter tops, tiled floors and walk in showers. HVAC 2020. Community amenities abound – enjoy the private beach with tiki’s, lounge chairs, pool, spa, library, community room with kitchen, marina access, bicycle storage, kayak launch, and additional owner’s storage space. With in walking distance to well renowned St Armands Circle for shopping and dining experiences. The pristine white sandy beach and gentle turquoise waters are calling your name. Schedule your private showing today and discover the lifestyle you deserve.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Diane Smith (941-313-4957)
2525 GULF OF MEXICO DR #3D, LONGBOAT KEY, FL 34228
$1,650,00018 Days on yellowkey MLS ID: A4696213
1 Days Off yellowkey (back on 6/16/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1468 Built: 1972 Tax: $18,254 (2025)Community: Islands WestSpa: YesCondo
Taxes:$18,254
Remarks: Under contract-accepting backup offers. Professional Photo's coming soon. Wake up to breathtaking, direct panoramic views of the Gulf of Mexico from this stunning third-floor beachfront residence on Longboat Key. Perfectly positioned to capture endless turquoise waters and spectacular sunsets, this coastal retreat offers unobstructed Gulf views, creating a serene backdrop for everyday living. The completely updated condo features two bedrooms, two baths, a spacious great room, dining area, and a kitchen with a charming breakfast nook. Walls of impact glass flood the interior with natural light, while floor-to-ceiling windows in both bedrooms showcase the ever-changing beauty of the shoreline. A wraparound balcony provides the perfect setting to enjoy morning coffee, coastal breezes, and mesmerizing sunsets over the Gulf. Ideally located mid-island, this residence offers the perfect balance of tranquility and convenience. Bay Isles Shoppes is just across the street, offering Publix, CVS, banking, dining, the Longboat Key Tennis Center, and Bayfront Park. World-renowned St. Armands Circle is only four miles away, while downtown Sarasota's acclaimed dining, shopping, arts, and entertainment are within a short seven-mile drive. Residents of Islands West enjoy an exceptional Gulf-front lifestyle with an impressive collection of resort-style amenities. The 15-story community features secure key-fob entry, a heated beachfront pool and spa, outdoor grilling and lounge areas, tennis and pickleball courts, and dedicated storage for bicycles, kayaks, and paddleboards. The clubhouse is currently being transformed to include a stylish social room with library, state-of-the-art fitness center, and catering kitchen. Pet lovers will appreciate the welcoming two-pet policy. Experience the ultimate beachfront lifestyle where spectacular views, resort-inspired amenities, and an unbeatable Longboat Key location come together in one extraordinary residence.
Listing Agent: Midge Mccarthy (941-809-3800)
1914 HARBOUR LINKS CIR #10, LONGBOAT KEY, FL 34228
$1,445,00086 Days on yellowkey MLS ID: A4686139
REDUCED by $50,000 (3.3%) on 05/20/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2180 Built: 2001 Tax: $12,540 (2025)Community: Emerald Pointe SouthSpa: NoCondo
Taxes:$12,540
Remarks: Tucked behind the gates of Bay Isles in the Emerald Pointe community, this 3BR/3.5BA residence offers 2,180+/- sq. ft. of thoughtfully designed living space with a layout that blends privacy, flexibility and inviting outdoor living. From the moment you arrive, a paver drive framed by lush landscaping and a striking 2-story façade with barrel tile roof set a warm and welcoming tone. A paver walkway leads to the courtyard entrance that defines the home’s character. This open yet private space is bathed in natural light and features a covered and screened sitting area with an all-season kitchen, creating a unique setting for entertaining or quiet relaxation. Just off the courtyard, a separate casita with its own full bath offers ideal space for a home office, guest suite or creative retreat. Inside, the home feels open and spacious, with large tile flooring, high ceilings and a thoughtful mix of clerestory and transom windows that bring light into every corner. Neutral tones and layered textures add depth without distraction. The living room is both functional and inviting, featuring a fireplace, built-in wine refrigerator, and ice maker that enhance the space for everyday living or hosting. The kitchen has been beautifully updated and connects naturally to the main living areas. It features stone countertops, all-white cabinetry, stainless steel appliances, a tile backsplash and a breakfast bar, along with a dining area highlighted by a striking aquarium window that looks back into the courtyard. The primary suite is located on the main living level in a private wing, offering direct access to the pool and a generous walk-in closet. The bath is well appointed with dual vanities, a freestanding tub, a walk-in shower and refined tilework. Upstairs, a guest bedroom provides comfort and privacy, complete with wood flooring, a walk-in closet, desk space and an en suite bath. At the back of the home, a screened lanai and pool overlook a peaceful lake with fountain, where large-panel screening keeps the view open and unobstructed. Additional features include an in-residence laundry room and a two-car garage with abundant storage. Residents of Emerald Pointe enjoy a maintenance-free lifestyle along with access to the private Bay Isles Beach Club, offering white sand beaches just minutes away. Optional membership to the Longboat Key Club further enhances the lifestyle with championship golf, tennis and pickleball, a private beach club, marina, spa and wellness amenities, multiple dining venues, and an active social calendar.
4310 FALMOUTH DR #304, LONGBOAT KEY, FL 34228
$330,000161 Days on yellowkey MLS ID: A4678473
REDUCED by $20,000 (5.7%) on 06/18/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 747 Built: 1969Monthly Fee: $1,196 Tax: $4,937 (2025)Community: Longboat HarbourCondo
Taxes:$4,937
Remarks: Unlock the Door to Your Dream Beach and Boating Lifestyle! Step into a world of unparalleled charm with this move-in ready, fully furnished gem on Longboat Key. This isn’t just a home; it’s a transformative lifestyle choice for those craving adventure, relaxation, and vibrant social connections. Picture yourself waking up to breathtaking bay views every morning from your stylish condo, featuring elegant granite countertops, state-of-the-art appliances, and a spa-like shower that redefines luxury. Your perfect beach days await with exclusive private beach access, complete with a dedicated beach house that offers showers and restrooms for your convenience. For boating enthusiasts, the Longboat Key Yacht Club provides convenient boat slips and kayaks, giving you immediate access to the pristine waters of the bay. Stay energized and engaged with an array of top-tier amenities, including tennis courts, shuffleboard, a rejuvenating sauna, and a fully equipped gym. Join a dynamic social scene filled with workshops, a cozy library, an inspiring art studio, and clay classes, plus the warm camaraderie of the Book Buddies club that fosters connections. With four inviting swimming pools, a grand banquet hall for gatherings, a fun game room for entertainment, and convenient private beach parking, every day feels like a luxurious getaway. This is more than just a condo; it’s a lifestyle experience you truly deserve. Don’t let this extraordinary Longboat Key oasis pass you by! Schedule your showing today and discover if it’s your perfect match!
Listing is courtesy of: HOUSE MATCH (941-213-7028)
Listing Agent: Rachel Rademacher (612-965-6188)
4234 GULF OF MEXICO DR #E2, LONGBOAT KEY, FL 34228
$580,000252 Days on yellowkey MLS ID: A4667654
REDUCED by $18,000 (3.0%) on 06/04/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1150 Built: 1973 Tax: $10,617 (2025)Community: Pelican Harbour & Beach ClubCondo
Taxes:$10,617
Remarks: REDUCED AND INCREDIBLE VALUE! EXCEPTIONAL FULL BAY VIEWS, PRIVATE BEACH ACCESS AND KAYAK LAUNCH, HURRICANE-RATED WINDOWS AND SLIDERS, UPDATED BATHS AND MORE! This 2BR/2BA retreat at Pelican Harbour & Beach Club delivers the quintessential Longboat Key lifestyle. From its 2nd-floor vantage point, enjoy peaceful sunrises over the Bay and the tranquil fountain view from your screened lanai, surrounded by lush tropical landscaping. Then, end your day with spectacular Gulf sunsets and leisurely beach walks from your private beach access. The updated kitchen gleams with new 2025 solid quartz countertops, stainless Samsung appliances, a tile backsplash, and a breakfast bar island—perfect for entertaining. Open living and dining areas flow seamlessly toward the water, creating a bright, inviting space ideal for relaxing or hosting friends. The spacious owner’s suite opens to the lanai and features a 2023-renovated ensuite bath with stone countertops, dual sinks, porcelain tile flooring, a glass shower, and custom closets. The guest suite offers another beautifully updated bath and generous storage. Additional highlights in-unit laundry, 2023 roof, 2024 exterior paint, and a hurricane-rated carport conveniently located just outside your door. This unit is currently rented, and tenants will vacate or stay so you can continue to earn rental income immediately! Ideally situated mid-island, Pelican Harbour & Beach Club offers outstanding amenities: Bay and beach access, first-come dock slips, a heated resort-style pool, two newly resurfaced tennis/pickleball courts, a clubhouse with social activities, kayak storage and launch, bike storage, and ample owner storage. This pet-friendly, rental-friendly community welcomes large dogs and seasonal visitors and perfectly combines luxury, flexibility, and coastal charm—just minutes from Bayfront Park, the new St. Regis Resort, St. Armands Circle, and downtown Sarasota’s vibrant restaurants, culture, and shopping.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lenore Treiman (941-356-9642)
615 DREAM ISLAND PL #105, LONGBOAT KEY, FL 34228
$949,00073 Days on yellowkey MLS ID: A4689957
REDUCED by $46,000 (4.6%) on 06/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1293 Built: 1985Monthly Fee: $2,172 Tax: $4,735 (2025)Community: Harbour Villa Club At The BuccaneerSpa: YesCondo
Taxes:$4,735
Remarks: Paradise Found: Fully Renovated Luxury at Harbour Villa Club, a True Longboat Key Gem! Welcome to a slice of heaven on the pristine North-End of Longboat Key at Harbour Villa Club. This luxurious, fully renovated (2025, not from storms) waterfront condo offers a lifestyle of serene elegance, perfectly positioned to capture breathtaking, unobstructed views of the glistening Sarasota Bay, the Intracoastal Waterway, and the protected Sister Keys. Step inside this exquisite home to an open, spacious floor plan bathed in natural light, thanks to high ceilings and expansive sliders. The custom gourmet kitchen is a chef's dream, featuring top-of-the-line appliances, ample counter space, and intelligent, creative storage solutions. The main living area is complemented by a sleek and stylish wet bar, ideal for effortless entertaining. The primary suite is a private sanctuary, designed for ultimate comfort with tremendous space, dual closets, and unparalleled water views. The equally luxurious primary bathroom features high-end fixtures, beautiful tile work, and a spacious shower. The secondary bedroom provides a generous space perfect for use as a guest suite or a flexible office. Relax or entertain year-round on your covered and screened lanai, the perfect outdoor space for sipping your morning coffee or evening cocktail while taking in the surrounding beauty. Boater's Dream and Unrivaled Flexibility: A rare and highly valuable amenity is the deeded boat slip #14, which conveys with the condo. This 40ft slip, equipped with electric, water, and new composite decking, is positioned directly outside the unit and can accommodate up to a 55'+/- vessel. Furthermore, Harbour Villa Club is one of the few Longboat Key communities with Weekly rental allowance, offering exceptional flexibility for ownership and use. Potentially generating gross approx. income of $85K annually with generous owner use availability. Community & Location: The community boasts mature tropical landscaping and grounds. Amenities include a heated pool, hot tub, outdoor grill, kayak storage/launch, boat ramp, climate-controlled bicycle/locker storage, and brand new tennis and pickleball courts. Located just a short walk to popular beaches, restaurants, and parks, and a short drive to St. Armands Circle and Downtown Sarasota. This property is more than a luxury condo—it is a complete lifestyle.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
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