Longboat Key, FL Homes for Sale under $800,000

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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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  /70

  $769,000

  $9K PRICE DROP

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

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

  This residence is now available for public and private showings. "One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!”Restricted access resulted in only three private showings in six months. Buyer's have a rare chance to discover a home that’s been under the radar. (Do not let the days on the market fool you. Snowbirds were unable to view this listing the entire "season").

  Debby McCaig COLDWELL BANKER REALTY

  4500 Gulf of Mexico Dr Unit 206, Longboat Key, FL 34228
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  /73

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,155 Sq Ft

  5260 Gulf of Mexico Dr Unit 413, Longboat Key, FL 34228

  Move-in-ready condition, ground-floor bayside condominium with Sarasota Bay views and deeded private Gulf beach access in the sought-after Banyan Bay Club! Discover effortless coastal living in this beautifully updated 2-bedroom, 2-bath residence offering 1,155 square feet on the bayside of Longboat Key. Thoughtfully renovated throughout, this inviting home features new luxury vinyl plank

  Bobbie Banan MICHAEL SAUNDERS & COMPANY

  5260 Gulf of Mexico Dr Unit 413, 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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  /47

  $520,000

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

  4310 Falmouth Dr Unit 307, Longboat Key, FL 34228

  Unlock the Door to Your Dream Beach & Boating Lifestyle! Welcome to your own slice of paradise on Longboat Key! This beautiful turnkey, fully furnished 2 bedroom, 2 bathroom condo offers the perfect blend of coastal living, resort-style amenities, and an active social lifestyle, all set against the backdrop of stunning panoramic bay views. Whether you’re looking for a full-time residence, a

  Rachel Rademacher HOUSE MATCH

  4310 Falmouth Dr Unit 307, Longboat Key, FL 34228
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  /55

  $599,000

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft

  1095 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228

  Welcome to Beachplace on Longboat Key! This spacious 2-bedroom, 2-bath residence with a den offers 1,503 square feet of living space and a wonderful opportunity to create your own island retreat in one of Longboat Key’s most established beachfront communities.The generous floor plan features an expansive living and dining area with plenty of room for entertaining, along with a versatile den

  Michael Renick MANGROVE REALTY ASSOCIATES

  1095 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
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  /66

  $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 2-bedroom, 2.5-bath residence featuring tranquil water views, an expanded open floor plan, and an updated kitchen with shaker cabinetry, granite countertops, and stainless steel appliances. Offered fully furnished and move-in ready, it's ideal as a primary residence, seasonal retreat, vacation home, or

  Rex Glasson DOUGLAS ELLIMAN

  848 Evergreen Way, Longboat Key, FL 34228
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  /68

  $725,000

  • 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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  /39

  $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

  $585,000

  $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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  /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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  /10

  $650,000

  • Land
  • 9,147 Sq Ft
  • $3,095,238 per Acre

  681 Gulf Bay Rd, Longboat Key, FL 34228

  Tucked along one of Longboat Key’s most peaceful and naturally beautiful streets is 681 Gulf Bay Road, a 9,000-square-foot homesite. Positioned just moments from Sarasota Bay and the Gulf of Mexico, this prime island lot offers the rare opportunity to design and build a custom coastal home in a location where nature, privacy, and convenience coexist effortlessly. Set on a quiet residential street

  Angela Scott MICHAEL SAUNDERS & COMPANY

  681 Gulf Bay Rd, Longboat Key, FL 34228
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  /61

  $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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  /69

  $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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  /45

  $565,000

  • 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 1,088 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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  /32

  $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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  /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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