Longboat Key, FL Homes for Sale with Pool

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  /39

  $470,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,072 Sq Ft

  4370 Chatham Dr Unit 104, Longboat Key, FL 34228

  Turnkey two-bedroom, two-bath residence in a first-floor, walkout location. Freshly painted with updated baths and 1,172 square feet of living space. Enjoy direct access to the harbor-front walking path and deeded beach access with baths, outdoor shower and chair storage. Includes a covered, assigned parking space. Resort-style amenities include a renovated clubhouse with kitchen and presentation

  Sharon Meier PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4370 Chatham Dr Unit 104, Longboat Key, FL 34228
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  $689,000

  Open Sat 1PM - 3PM $86K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft

  4900 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

  IN THE COVETED "B" BUILDING, A STRATEGIC PRICE REFINEMENT NOW POSITIONS THIS EXCEPTIONAL RESIDENCE AS THE MOST COMPELLING OFFERING AT WINDWARD BAY! A BAYFRONT BEAUTY! VIEWS THAT STEAL THE SHOW! Discover the ultimate in Florida Gulf-to-Bay living with this beautifully remodeled 2-bedroom, 2-bath luxury condo offering jaw-dropping, multi-million-dollar water views of Sarasota Bay. From the moment

  Debby McCaig COLDWELL BANKER REALTY

  4900 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
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  $475,000

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft

  6800 Gulf of Mexico Dr Unit 184, Longboat Key, FL 34228

  Beautifully renovated in 2023, with dazzling views of the Gulf of Mexico and the private beach across the way, this 2nd floor island retreat is located in a charming Gulf-to-Bay community, nestled between the azure blue water of the Gulf of Mexico and serene Bishops Bayou, where Manatees & Dolphins play. This lovely 2nd level end-unit features an open floor plan, enhanced by a gorgeous designer

  Tina Rudek Stark, PA ROSEBAY INTERNATIONAL REALTY, INC

  6800 Gulf of Mexico Dr Unit 184, Longboat Key, FL 34228
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  $2,400,000

  • 3 Beds
  • 3.5 Baths
  • 3,192 Sq Ft

  3610 Bayou Cir, Longboat Key, FL 34228

  Welcome to The Bayou section of beautiful Bay Isles. Tucked away from the hustle and bustle of daily life, this double-gated community, a collection of 126 homes, is the perfect place to be on Longboat Key. The pavered front circular drive delivers you to the elevated double-door entrance. Step inside and prepare to be delighted by the neutral palate throughout and an abundance of natural light.

  Mike Prisco MICHAEL SAUNDERS & COMPANY

  3610 Bayou Cir, Longboat Key, FL 34228
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  $2,149,000

  Open Tue 1PM - 4PM $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,311 Sq Ft

  500 Halyard Ln, Longboat Key, FL 34228

  Gorgeous Views - Impact Windows & Doors - 1/2 Acre Elevated Lot - Enjoy the Longboat Key Island Lifestyle - In a prime South Longboat Key location, this beautifully updated waterfront home offers a blend of privacy, comfort and exceptional boating access. Set on a large, elevated, tropically landscaped lot, the property captures wide water canal views stretching toward Sarasota Bay, with stunning

  Mike Seamon PREMIER SOTHEBY'S INTERNATIONAL REALTY

  500 Halyard Ln, Longboat Key, FL 34228
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  $839,900

  $59K 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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  $750,000

  • 2 Beds
  • 2 Baths
  • 1,449 Sq Ft

  925 Spanish Dr N Unit 60, Longboat Key, FL 34228

  Wow! Panoramic water views from almost every window, plus rare direct access to Bay waters just near the back paver patio. This completely renovated two-bedroom, two-bath, 1,449-square-foot home is a must see! Fully remodeled in 2025/2026 in full compliance with FEMA requirements. It is all about details as this gorgeous Spanish Main turnkey furnished villa is ready to welcome you home! The

  Kimberly Freiwald PREMIER SOTHEBY'S INTERNATIONAL REALTY

  925 Spanish Dr N Unit 60, 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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  $1,595,000

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

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

  This is the gorgeous ground floor, walk-out unit next to the beach you've been looking for. Do you prefer to live like a single family home, no elevator, and walk straight out to the beach? Then this is the One! Welcome to Sea Gate Club on beautiful Longboat Key, perfectly positioned near mid-island, and close to shopping at Publix or CVS. As you enter this very private End Unit #1A, you're

  Robert Delaney MICHAEL SAUNDERS & COMPANY

  2425 Gulf of Mexico Dr Unit 1A, Longboat Key, FL 34228
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  $1,095,000

  • 2 Beds
  • 2 Baths
  • 1,239 Sq Ft

  4311 Gulf of Mexico Dr Unit 501, Longboat Key, FL 34228

  Some Photo's are virtually staged ! Spectacular gulf front views from this 5th floor 2 bedroom/ 2 bathroom condo residence in rarely available Longboat Beach House with convenient mid key location in close proximity to Longboat Key shops & restaurants as well as Bayfront Park with its pickleball courts and kayak launch and St Armands Circle. Left entirely unscathed by the recent storms, this unit

  Richard Perlman MICHAEL SAUNDERS & COMPANY

  4311 Gulf of Mexico Dr Unit 501, Longboat Key, FL 34228
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  $5,495,000

  New Construction $255K PRICE DROP

  • 4 Beds
  • 6 Baths
  • 3,737 Sq Ft

  524 Halyard Ln, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. Only ONE BUYER will be the FIRST OWNER! Crafted by an award winning design team, this brand-new coastal contemporary waterfront residence awaits you in the exclusive Country Club Shores community on South Longboat Key. Designed for high performance and easy maintenance, this rock-solid, all block two-story residence with a private elevator provides

  Rob Hunt, Jr HUNT BROTHERS REALTY, INC.

  524 Halyard Ln, Longboat Key, FL 34228

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