Longboat Key, FL Homes for Sale with Acreage

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  $899,900

  • 1 Bed
  • 1 Bath
  • 640 Sq Ft

  250 Sands Point Rd Unit 5203, Longboat Key, FL 34228

  Four Diamond Resort with five restaurants, 45 holes of Golf, Spa, Marina, 21 Tennis courts on Longboat Key!!!. This income producing property on the beachside with a golf course view is calling you!!!. It's a one-bedroom studio at the Resort on Longboat Key, a gated community. Presently the unit is in the Resort rental program and the owner may use the unit 28 days per year.

  Tom Cinquegrano MICHAEL SAUNDERS & COMPANY

  250 Sands Point Rd Unit 5203, Longboat Key, FL 34228
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  /33

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,341 Sq Ft

  914 Spanish Dr S Unit 76, Longboat Key, FL 34228

  Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the highly sought-after 55+ community of Spanish Main Yacht Club! This newly remodeled 2-bedroom, 2-bathroom residence is offered fully furnished turnkey with all brand-new, high-end coastal furnishings. Ideally situated just steps from the active marina and a picturesque seawall—perfect for peaceful

  Geoff Scalera AUM FLORIDA REAL ESTATE LLC

  914 Spanish Dr S Unit 76, Longboat Key, FL 34228
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  /45

  $950,000

  $100K PRICE DROP

  • 1 Bed
  • 2 Baths
  • 940 Sq Ft

  1241 Gulf of Mexico Dr Unit 111, Longboat Key, FL 34228

  This unique plaza level Water Club residence offers you the convenience of stepping out to the exceptional Water Club amenities and lush grounds that lead to the sandy beach and azure waters of the Gulf of Mexico without the use of an elevator. This spacious 1 bedroom special residence features high 10 foot ceilings and the openness is enhanced by the floor to ceiling windows that captivate the

  Reid Murphy DEVELOPERS REALTY LBK, INC

  1241 Gulf of Mexico Dr Unit 111, Longboat Key, FL 34228
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  $619,000

  Open Sun 1PM - 4PM

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft

  605 Sutton Place Unit 201, Longboat Key, FL 34228

  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

  Melissa Rodocker RE/MAX ALLIANCE GROUP

  605 Sutton Place Unit 201, Longboat Key, FL 34228
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  /68

  $769,000

  $9K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,523 Sq Ft

  4500 Gulf of Mexico Dr Unit 206, Longboat Key, FL 34228

  "One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!”The only coveted South Marina corner/end unit currently on the market at Windward Bay—these special residences are truly prized. End units are usually the first to sell, and for good reason: they offer approximately 250 additional square feet of living space, flooding your home with light and delivering a bright, inviting

  Debby McCaig COLDWELL BANKER REALTY

  4500 Gulf of Mexico Dr Unit 206, Longboat Key, FL 34228
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  $1,699,000

  $300K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft

  2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228

  BREATHTAKING WATER VIEWS FROM EVERY ROOM! Enjoy nightly sunsets from your private balcony in this beautifully updated 14th-floor condominium. This highly sought-after two-bedroom, two-bath split floorplan offers the perfect blend of privacy and open living. Each bedroom is positioned on opposite sides of the unit, creating an ideal layout for guests or remote work. Recent upgrades include

  Andrey markov ANMARK REALTY LLC

  2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
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  /39

  $3,249,000

  $446K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 3,045 Sq Ft

  1241 Gulf of Mexico Dr Unit 803, Longboat Key, FL 34228

  The epitome of beachfront luxury awaits in this meticulously renovated 8th-floor residence at the prestigious Water Club on Longboat Key. This stunning 3-bedroom plus oversized study, 4-bath home is a rare offering in one of the Gulf Coast’s premier direct beachfront communities. From the moment you step off the private elevator into the foyer, you’re greeted by serene neutral tones, 10-foot

  Ryan Ackerman COLDWELL BANKER REALTY

  1241 Gulf of Mexico Dr Unit 803, Longboat Key, FL 34228
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  /75

  $6,100,000

  • 3 Beds
  • 5 Baths
  • 3,380 Sq Ft

  415 L Ambiance Dr Unit A301, Longboat Key, FL 34228

  Rare corner Gulf-front residence with expansive wraparound terrace and views. An exceptional residence in L’Ambiance, where sweeping water views and refined coastal design converge. This light-filled corner home is defined by an expansive wraparound terrace, offering multiple seating areas and uninterrupted vistas of the Gulf - creating a seamless connection between indoor and outdoor living.

  Bruce Myer COLDWELL BANKER REALTY

  415 L Ambiance Dr Unit A301, Longboat Key, FL 34228
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  /58

  $875,000

  $24K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  2055 Gulf of Mexico Dr Unit G2109, Longboat Key, FL 34228

  NEW PRICE ADJUSTMENT: Rarely available and a wonderful opportunity to own a three bedroom/two bath condominium located in a garden building with partial gulf views from all rooms. walk out to your lanai and enjoy the beautiful flowering trees & foliage. Bright and spacious with travertine tile and wooden flooring throughout, stainless steel appliances and cambria quartz countertops in the kitchen

  Sandra Endres COLDWELL BANKER REALTY

  2055 Gulf of Mexico Dr Unit G2109, Longboat Key, FL 34228
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  /46

  $599,000

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,306 Sq Ft

  448 Gulf of Mexico Dr Unit A205, Longboat Key, FL 34228

  Enjoy the benefits of a well-managed waterfront community with just 39 residences and attractively low condominium association fees. Set within an intimate waterfront enclave, this Bay Harbour retreat captures the essence of refined island living. Framed by swaying palms and 720 feet of shimmering Sarasota Bay frontage, the community feels like a private tropical sanctuary, where beautiful

  Kathleen Wingate PREMIER SOTHEBY'S INTERNATIONAL REALTY

  448 Gulf of Mexico Dr Unit A205, Longboat Key, FL 34228
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  /18

  $410,000

  $15K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 936 Sq Ft

  6700 Gulf of Mexico Dr Unit 143, Longboat Key, FL 34228

  Welcome to your coastal retreat on beautiful Longboat Key! This charming second-story condo is being offered turnkey furnished, making it completely move-in ready—just bring your suitcase and start enjoying island life. Inside, the bright living room showcases peaceful water views bringing the beauty of marine life right to your window. The kitchen features stainless steel appliances and

  Brooke Moran DALTON WADE INC

  6700 Gulf of Mexico Dr Unit 143, Longboat Key, FL 34228
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  /47

  $1,025,000

  • 1 Bed
  • 1 Bath
  • 640 Sq Ft

  240 Sands Point Rd Unit 4104, Longboat Key, FL 34228

  Introducing a highly sought-after first-floor Junior Suite in Building 4, boasting stunning Gulf views and now available for purchase. This fully renovated unit is part of the hotel program, generating over $118K in gross income for 2025, with more than $79K already booked through April 2026, indicating the potential for even greater earnings this year. Enjoy an expanded deck alongside a covered

  Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  240 Sands Point Rd Unit 4104, Longboat Key, FL 34228
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  /37

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,361 Sq Ft

  683 Spanish Dr S Unit 214, Longboat Key, FL 34228

  Experience the ultimate Longboat Key lifestyle in this beautifully renovated single-story villa located in the highly sought-after 55+ waterfront community of Spanish Main Yacht Club. This move-in-ready 2-bedroom, 2-bath residence features a bright, open floor plan, brand-new appliances, updated finishes throughout, and a spacious Florida room perfect for relaxing or entertaining. Ideally

  Geoff Scalera AUM FLORIDA REAL ESTATE LLC

  683 Spanish Dr S Unit 214, Longboat Key, FL 34228
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  /28

  $515,000

  • 2 Beds
  • 2 Baths
  • 933 Sq Ft

  1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228

  Seaplace Condominiums, half mile Gulf of Mexico beachfront property with chaise lounges & umbrellas provided on private beach portion. Elegant turnkey-furnished unit with hurricane impact doors & windows. Next to clubhouse pool, gym, sauna & community kitchen. Two properties from St. Regis Resort restaurants & beach bar.

  Stephen Hachey FLAT FEE MLS REALTY

  1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228
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  $599,900

  • 2 Beds
  • 2.5 Baths
  • 1,440 Sq Ft

  848 Evergreen Way, Longboat Key, FL 34228

  Turn-Key Furnished Waterfront Townhome in Cedars East on Longboat Key! Beautifully updated and move-in ready, this desirable 2-bedroom, 2.5-bath residence offers one of the best locations within Cedars East, featuring tranquil water views from the spacious primary suite and an expanded, open-concept living area. The updated kitchen showcases shaker-style cabinetry, granite countertops, stainless

  Rex Glasson DOUGLAS ELLIMAN

  848 Evergreen Way, Longboat Key, FL 34228
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  /38

  $675,000

  • 2 Beds
  • 2 Baths
  • 1,362 Sq Ft

  3330 Gulf of Mexico Dr Unit 107D, Longboat Key, FL 34228

  Island Elegance on the Bay: A Turnkey Waterfront Sanctuary! Escape to the serene shores of Longboat Key and experience the pinnacle of coastal luxury at 3330 Gulf of Mexico Drive. This meticulously reimagined, two-bedroom, two-bathroom residence offers a rare "walk-out" lifestyle, where lush green lawns meet the shimmering waters of the Sarasota Bay. The Interior: Modern Luxury Meets Tropical

  Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

  3330 Gulf of Mexico Dr Unit 107D, Longboat Key, FL 34228
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  /59

  $599,000

  Open Fri 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

  4720 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228

  Welcome to coastal luxury living in Windward Bay, one of Longboat Key's most sought-after waterfront communities. Perfectly positioned between the sparkling waters of Sarasota Bay and the pristine Gulf beaches, this completely renovated 2-bedroom, 2-bath villa offers an exceptional blend of modern elegance, resort-style amenities, and the coveted island lifestyle buyers dream about. Fully

  Sharon Austin PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4720 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
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  /40

  $799,000

  • 2 Beds
  • 2 Baths
  • 1,110 Sq Ft

  5311 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228

  Turnkey furnished and positioned just steps from the Gulf’s sandy shoreline, this first-floor residence at Beach Castle on Longboat Key offers a compelling combination of coastal living and proven rental potential. With flexible daily or weekly rental allowances, this two-bedroom retreat presents an exceptional opportunity for personal use, income generation, or both. The light-filled interior

  Roger Pettingell COLDWELL BANKER REALTY

  5311 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228
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  /22

  $749,900

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft

  4835 Gulf of Mexico Dr Unit 106, Longboat Key, FL 34228

  Waterfront Living on Longboat Key – Direct Gulf AccessExperience the best of coastal living on beautiful Longboat Key. This first-floor residence offers effortless access and an unbeatable connection to the water, with direct access to the stunning Gulf of Mexico just steps from your door. Recently updated, the home features brand-new flooring throughout, along with all-new hurricane-impact

  Toni Giliberti COLDWELL BANKER REALTY

  4835 Gulf of Mexico Dr Unit 106, Longboat Key, FL 34228
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  /37

  $960,000

  • 1 Bed
  • 1 Bath
  • 634 Sq Ft

  250 Sands Point Rd Unit 5106, Longboat Key, FL 34228

  Completely renovated first floor walkdown Junior Suite with spectacular views of Longboat Key Club’s Golf Course currently in the hotel program now available. There is an expanded deck in addition to the covered terrace, ideal for watching a wide variety of wildlife and golfing activity. Building 5 is positioned where owners value privacy from the hustle and bustle of the main entrance and pool

  Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  250 Sands Point Rd Unit 5106, Longboat Key, FL 34228
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  $2,345,000

  $50K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,314 Sq Ft

  340 Gulf of Mexico Dr Unit 115, Longboat Key, FL 34228

  Your Longboat Key oasis awaits! This totally renovated 3bdrm 2.5 bath condo offers a open concept living space with high ceilings and walls of glass allowing sweeping views os Sarasota Bay. Light and bright material selections mix modern luxury with a coastal theme.The gourmet kitchen features white soft close custom cabinetry, sleek glass doors, quartz countertops, mother of pearl

  Reid Murphy DEVELOPERS REALTY LBK, INC

  340 Gulf of Mexico Dr Unit 115, Longboat Key, FL 34228
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  /39

  $799,000

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,274 Sq Ft

  5655 Gulf of Mexico Dr Unit D107, Longboat Key, FL 34228

  Experience breathtaking beach and Gulf views from this spacious, turnkey-furnished two-bedroom, two-bath residence in Cedars West. Beautifully updated with no detail overlooked, this exceptional property features elegant stone countertops, quality appliances, and a relaxed coastal ambiance that makes it highly sought after. Offering over 1,270 square feet of air-conditioned living space, the

  John Milkovich CHARLES RUTENBERG REALTY INC

  5655 Gulf of Mexico Dr Unit D107, Longboat Key, FL 34228
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  /50

  $1,775,000

  $175K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,298 Sq Ft

  340 Gulf of Mexico Dr Unit 112, Longboat Key, FL 34228

  Perfectly positioned on Sarasota Bay at the southern end of Longboat Key, this beautifully renovated 3BR/3BA, 2,298± sq. ft. residence with a private 2-car garage at Tangerine Bay Club combines luxury, comfort, and a premier location just moments from St. Armands Circle and downtown Sarasota. A private front courtyard welcomes you inside, where rich wood floors, custom doors, and neutral tones

  Bruce Myer COLDWELL BANKER REALTY

  340 Gulf of Mexico Dr Unit 112, Longboat Key, FL 34228
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  /26

  $649,000

  • 2 Beds
  • 2 Baths
  • 1,376 Sq Ft

  4440 Exeter Dr Unit 106, Longboat Key, FL 34228

  Welcome to Longboat Harbour, a gated waterfront community offering resort-style living on beautiful Longboat Key. This first-floor corner unit, N-106, features two bedrooms, two baths, and an assigned covered carport — all set against unparalleled views of Sarasota Bay and the Intracoastal Waterway.Step inside to find ceramis plank flooring throughout and a light-filled, open layout designed

  Roger Richmond KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  4440 Exeter Dr Unit 106, Longboat Key, FL 34228

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