Longboat Key, FL Homes for Sale with Pool

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  /68

  $725,000

  Open Sat 1PM - 4PM

  • 2 Beds
  • 2 Baths
  • 1,194 Sq Ft

  448 Gulf of Mexico Dr Unit A104, Longboat Key, FL 34228

  Location! Location! Location! Awesome, Spectacular Bay views from the kitchen, dining room, living room and primary bedroom! One Bridge to the Gulf! No wait list boat slip! Longboat Key is the place you want to be for the quiet solitude of a gulf front key condo with easy access to the culture and services of Sarasota! This two bedroom, two bathroom Condo in the bay side community of Bay Harbour,

  Diana Kryszak MICHAEL SAUNDERS & COMPANY

  448 Gulf of Mexico Dr Unit A104, Longboat Key, FL 34228
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  $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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  $1,575,000

  • 2 Beds
  • 2 Baths
  • 1,472 Sq Ft

  2425 Gulf of Mexico Dr Unit 1B, Longboat Key, FL 34228

  Welcome to unit 1B at Sea Gate Club on beautiful Longboat Key. This is the gorgeous, newly remodeled Beachfront walkout unit that you've been waiting for! Do you prefer to live like a single family home, no elevator, and walk straight out to the sandy beach in less than 100 steps? Then this is the One! Perfectly positioned near mid-island, and close to shopping at Publix or CVS. 2 bedrooms with

  Robert Delaney MICHAEL SAUNDERS & COMPANY

  2425 Gulf of Mexico Dr Unit 1B, Longboat Key, FL 34228
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  $950,000

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,235 Sq Ft

  2301 Gulf of Mexico Dr Unit 43, Longboat Key, FL 34228

  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

  Steve Nursey MICHAEL SAUNDERS & COMPANY

  2301 Gulf of Mexico Dr Unit 43, Longboat Key, FL 34228
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  $585,000

  Open Sat 1PM - 3PM $14K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

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

  Completely renovated two-bedroom and two-bathroom walkout (no stairs to take) on Longboat Key! 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

  Sharon Austin PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4720 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
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  $529,000

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft

  531 Sutton Place, Longboat Key, FL 34228

  Your easy island escape awaits in the beach-to-bay community of Sutton Place on Longboat Key. Spend your days at the deeded Gulf beach, lounging by one of two heated pools, kayaking on the bay, or heading out on the water—all within the community. This two-bedroom townhome is ideal for seasonal or year round living, offering impact windows and doors, steel roof trusses, and a private oversized

  Sherri Mills MICHAEL SAUNDERS & COMPANY

  531 Sutton Place, 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

  $700,000

  $50K PRICE DROP

  • 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

  Toni Giliberti COLDWELL BANKER REALTY

  4835 Gulf of Mexico Dr Unit 106, Longboat Key, FL 34228
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  $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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  $754,900

  $40K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,460 Sq Ft

  5270 Gulf of Mexico Dr Unit 508, Longboat Key, FL 34228

  Rarely available and beautifully positioned, this 3-bedroom, 3-bath fully furnished residence with UNOBSTRUCTED FULL BAY VIEWS invites you to experience true beach-to-bay living in the coveted community of Banyan Bay on the north end of Longboat Key. From sunrise coffees on your private terrace to evenings spent watching dolphins glide across the bay, this home offers an effortless blend of

  Beth Ann Boyer MICHAEL SAUNDERS & COMPANY

  5270 Gulf of Mexico Dr Unit 508, Longboat Key, FL 34228
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  $2,150,000

  $345K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,972 Sq Ft

  617 Rountree Dr, Longboat Key, FL 34228

  Discover the perfect canvas for your coastal vision in the prestigious Longboat Key Estates. This premier waterfront opportunity offers 100 feet of direct canal frontage in one of the island’s most desirable enclaves.Positioned on a quiet interior street, this property sits in an area undergoing significant luxury transformation, providing an ideal foundation for a custom residence with

  Judi Taulbee FINE PROPERTIES

  617 Rountree Dr, Longboat Key, FL 34228
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  $1,749,500

  $300K PRICE DROP

  • 2 Beds
  • 3 Baths
  • 2,823 Sq Ft

  5920 Gulf of Mexico Dr, Longboat Key, FL 34228

  DEEDED BEACH ACCESS AND DEEP WATER CANAL at this beautifully renovated mid-key beach house on the barrier island of Longboat Key. You can enjoy a 3-minute walk to the beach using your private beach access or step outside and enjoy the canal on your trex dock. The uncrowded beach with natural surroundings, fine sand beaches, warm breezes, and clear turquoise waters is truly a special place.

  John Donato JOHN DONATO REAL ESTATE INC

  5920 Gulf of Mexico Dr, Longboat Key, FL 34228
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  $750,000

  • 2 Beds
  • 2 Baths
  • 1,423 Sq Ft

  900 Spanish Dr N, Longboat Key, FL 34228

  This must-see hidden gem on the north end of Longboat Key offers a quintessential Florida lifestyle. Waterview’s galore as you walk into your newly completed, renovated Florida paradise home, on a deepwater marina and canal, which epitomizes beauty and style. Boat lovers will want the location of this totally turnkey furnished 1,423-square-foot standalone two-bedroom, two-bath home, with your

  Kimberly Freiwald PREMIER SOTHEBY'S INTERNATIONAL REALTY

  900 Spanish Dr N, Longboat Key, FL 34228
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  $4,999,000

  Open Sun 1PM - 4PM

  • 5 Beds
  • 3 Baths
  • 3,842 Sq Ft

  3606 Fair Oaks Place, Longboat Key, FL 34228

  Nestled behind the gates of the highly celebrated Bay Isles community, this exceptional five-bedroom waterfront residence at 3606 Fair Oaks Lane offers the perfect blend of luxury, comfort, and peace of mind with an impressive list of recent upgrades and improvements. Designed for effortless coastal living, this beautifully updated home showcases refined interiors, expansive outdoor living

  Renee Preininger SARASOTA TRUST REALTY COMPANY

  3606 Fair Oaks Place, Longboat Key, FL 34228
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  $699,000

  $130K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft

  4725 Gulf of Mexico Dr Unit 314, Longboat Key, FL 34228

  Welcome to Sand Cay Beach Resort—one of Longboat Key’s premier vacation destinations. VACATION WHEN YOU WANT - GENERATE INCOME WHEN YOU DON'T - TURNKEY GULF-SIDE INVESTMENT WITH REAL RETURNS. Rarely available third-floor condo truly impresses with soaring vaulted ceilings exclusive to top-floor residences, a beautifully updated kitchen, and tasteful coastal-inspired finishes throughout. A

  Michael Albano, PA COLDWELL BANKER REALTY

  4725 Gulf of Mexico Dr Unit 314, Longboat Key, FL 34228
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  $2,999,999

  • 6 Beds
  • 5.5 Baths
  • 4,676 Sq Ft

  614 Norton St, Longboat Key, FL 34228

  Virtually Staged. Welcome to an extraordinary waterfront estate on coveted Longboat Key, where timeless coastal elegance meets world-class boating. Perfectly situated on a deep-water saltwater canal with a private dock and direct access to the Gulf, this exceptional residence offers the rare opportunity to experience the very best of Florida luxury living just moments from the island's pristine

  Jordan Rye COMPASS FLORIDA, LLC

  614 Norton St, Longboat Key, FL 34228
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  /24

  $6,995,000

  New Construction

  • 6 Beds
  • 6.5 Baths
  • 4,776 Sq Ft

  7094 Longboat Dr E, Longboat Key, FL 34228

  Pre-Construction. To be built. An extraordinary opportunity to create a world-class waterfront estate on Sarasota Bay, this stunning new construction residence offers the ultimate blend of luxury, craftsmanship, and coastal living in one of Sarasota’s most coveted locations. Situated on an expansive 11,000+ square foot bayfront homesite, this magnificent two-story design features six spacious

  Renee Preininger SARASOTA TRUST REALTY COMPANY

  7094 Longboat Dr E, Longboat Key, FL 34228
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  $565,000

  Open Sun 12PM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft

  713 Saint Judes Dr S Unit 2, Longboat Key, FL 34228

  WATERFRONT LONGBOAT KEY LIVING WITH PRIVATE DOCK, EXTENSIVE 2025 RENOVATIONS AND PROVEN RENTAL PERFORMANCE. Welcome to 713 Saint Judes Drive S #2, a turn-key furnished 2-bedroom, 2-bath waterfront residence offering approximately 1,215 square feet with direct boating access to the Intracoastal Waterway.Extensively renovated in 2025, the residence features a new kitchen with quartz

  Rex Glasson DOUGLAS ELLIMAN

  713 Saint Judes Dr S Unit 2, Longboat Key, FL 34228
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  $1,199,000

  • 2 Beds
  • 2 Baths
  • 1,235 Sq Ft

  2301 Gulf of Mexico Dr Unit 33, Longboat Key, FL 34228

  Experience breathtaking beachfront living in this rare direct Gulf-front residence at the prestigious Islander Club on Longboat Key. This two-bedroom, two-bath condominium showcases panoramic Gulf of Mexico views from every room, including the living room, primary suite and guest bedroom, creating a spectacular coastal backdrop throughout the home. One of the exceptional features of this

  Chris Wetzig PREMIER SOTHEBY'S INTERNATIONAL REALTY

  2301 Gulf of Mexico Dr Unit 33, Longboat Key, FL 34228
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  $749,900

  $149K PRICE DROP

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

  4825 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228

  Experience the epitome of Island living in this meticulously kept and beautifully renovated retreat located in the beachfront community of The Westchester on Longboat Key. This ground floor walk-out, 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous kitchen opens to the large living/dining area and the spectacular views can be seen through impact

  JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  4825 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228
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  $2,550,000

  Open Sun 1PM - 4PM

  • 4 Beds
  • 4.5 Baths
  • 4,154 Sq Ft

  3527 Fair Oaks Ln, Longboat Key, FL 34228

  Experience refined coastal luxury in this impeccably renovated 4,154-square-foot golf course estate, ideally positioned within the exclusive Queens Harbour enclave of gated Bay Isles on Longboat Key. This extraordinary two-story residence offers 4 bedrooms, 4.5 bathrooms, and an elegant open floor plan thoughtfully curated with exquisite finishes and designer details throughout. Extensive recent

  Miriam Pearson COLDWELL BANKER REALTY

  3527 Fair Oaks Ln, 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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