Longboat Key, FL Homes for Sale under $1,000,000

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  /27

  $949,900

  • 2 Beds
  • 2 Baths
  • 1,509 Sq Ft

  615 Dream Island Place Unit 210, Longboat Key, FL 34228

  Paradise at Harbour Villa Club – Waterfront Luxury with a boat slip on Longboat Key! Enjoy this condo year round, or rent it weekly when you cannot be there- you choose! Discover this fully renovated 2BR/2BA condo with panoramic views of the gorgeous Sarasota Bay. Bright and spacious, the open floor plan features soaring 9 ft ceilings, custom finishes, a gourmet kitchen with top-of-the-line

  Lori Lahart CENTURY 21 BILL NYE REALTY

  615 Dream Island Place Unit 210, Longboat Key, FL 34228
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  /64

  $899,000

  $201K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft

  1105 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

  Direct Ocean view from this Bright Airy corner unit in desirable building five. Catch the view of the Gulf of Mexico and Sunsets from your balcony. To see this property is to fall in love with easy living! You need to visit this unit to get a sense of the remarkable views , especially the amount of light that permeates the entire interior. Beachplace is a perfect get away on the south end of

  Jim Weingart COLDWELL BANKER REALTY

  1105 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228
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  /45

  $975,000

  $175K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,707 Sq Ft

  1425 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228

  Step inside and be immediately greeted by stunning, uninterrupted views of the Gulf of Mexico, setting the tone for this exceptional Players Club residence. This home is being sold FURNISHED, you just need to bring your toothbrush. The well-appointed kitchen features generous counter space and *stainless steel appliances*, making meal preparation a delight—especially with your own gulf view

  Mairead Smialek COLDWELL BANKER REALTY

  1425 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228
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  /35

  $975,000

  $250K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,031 Sq Ft

  2120 Harbourside Dr Unit 623, Longboat Key, FL 34228

  Step into coastal elegance in this fully renovated three-bedroom, two-bathroom Fairway Bay residence, where every detail has been thoughtfully reimagined. A charming private lanai and seating area welcome you before entering the unit, setting the tone for relaxed waterfront living. Inside, an open-concept layout seamlessly blends the kitchen, dining, and living spaces, creating a bright, airy

  Ryan Ackerman COLDWELL BANKER REALTY

  2120 Harbourside Dr Unit 623, Longboat Key, FL 34228
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  /70

  $745,000

  $85K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,022 Sq Ft

  4485 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

  Experience exceptional beachfront living in this beautiful Gulf-front residence at Arbomar on Longboat Key. Unit 402 is a 2-bedroom, 2-bath condominium offering direct, unobstructed Gulf of Mexico views and immediate beach access, making it the most affordable 2-bedroom, 2-bath opportunity on Longboat Key with true Gulf frontage. The residence features a bright, open layout designed to capture

  Richard Tyson PREFERRED SHORE LLC

  4485 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
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  /59

  $995,000

  • 2 Beds
  • 2 Baths
  • 1,409 Sq Ft

  1050 Longboat Club Rd Unit 903, Longboat Key, FL 34228

  Set on the 9th floor at Privateer North, behind the gates of the Longboat Key Club, this beautifully renovated corner residence blends sweeping views, refined finishes and effortless coastal living. Offered TURNKEY FURNISHED, the 2-bedroom, 2-bath home looks out across the golf course, Sarasota Bay, the Intracoastal Waterway and the downtown Sarasota skyline, creating a view that shifts

  Bruce Myer COLDWELL BANKER REALTY

  1050 Longboat Club Rd Unit 903, Longboat Key, FL 34228
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  /38

  $996,000

  $154K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 634 Sq Ft

  230 Sands Point Rd Unit 3205, Longboat Key, FL 34228

  Spectacular Gulf and Sunset views are enjoyed from this west facing Junior Suite in Building 3. The direct beach view through the swaying palms perfectly encompasses the resort lifestyle and the vision guests have of tropical landscapes when making reservations. This completely renovated residence is currently in the hotel program and reported healthy income in 2023 and 2024. As an owner, you are

  Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  230 Sands Point Rd Unit 3205, Longboat Key, FL 34228
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  /51

  $900,000

  $200K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,792 Sq Ft

  578 Companion Way, Longboat Key, FL 34228

  Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the ultimate coastal lifestyle with sun, sand, and breathtaking surroundings at an exceptional value. Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and

  Linh Pham NEXTHOME EXCELLENCE

  578 Companion Way, Longboat Key, FL 34228
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  /38

  $999,000

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft

  4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  Direct beachfront living! This beautifully updated 2-bedroom, 2-bath residence offers unobstructed Gulf of Mexico views and front-row access to a slice of Longboat Key’s most quiet and uncrowded shoreline. Available fully furnished and turnkey, this condo is ready for immediate enjoyment as a primary residence, seasonal escape, or investment property. The spacious open layout connects the

  Daniel Goldman COMPASS FLORIDA LLC

  4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
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  /29

  $825,000

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

  4825 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

  Discover coastal living at its finest in this beautifully positioned 2-bedroom, 2-bath condominium on one of Longboat Key’s most sought-after stretches. This residence offers spectacular, breathtaking views from both private lanais—perfect for enjoying sunrise coffee or evening sunsets over the water. Inside, the layout is bright and inviting, with seamless indoor-outdoor flow that maximizes the

  Toni Giliberti COLDWELL BANKER REALTY

  4825 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
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  /38

  $950,000

  $100K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 640 Sq Ft

  240 Sands Point Rd Unit 4102, Longboat Key, FL 34228

  Highly desirable and rarely available 1st floor walkdown Junior Suite with Gulf views in Building 4 now available. This completely renovated unit is currently in the hotel program and reported healthy income in 2023 and 2024. There is an expanded deck in addition to the covered terrace, which provides direct access to the beach. Building 4 is situated farthest north on the gulf side where owners

  Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  240 Sands Point Rd Unit 4102, Longboat Key, FL 34228
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  /47

  $845,000

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft

  1065 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

  This stunning 2 bed/2 bath residence comes turnkey furnished offering a full view of the Longboat Key Islandside Golf Course and partial views of the Gulf, Sarasota Bay, and the Sarasota city skyline through Hurricane Impact Sliders installed in 2024. The kitchen has been opened up to the living/dining area providing a beautiful view over the golf course greens while owners are creating culinary

  Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  1065 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
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  /32

  $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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  /43

  $700,000

  $140K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,387 Sq Ft

  624 Saint Judes Dr, Longboat Key, FL 34228

  Due to a change with the buyer, this stunning property is back on the market and available for immediate showing. Everything is prepped, cleaned, and ready for a new owner. If you or your client missed this the first time, now is the perfect time to take a second look. Let’s get you in for a private tour before it’s gone again! On site you will discover this stunning, fully renovated Cali-Modern

  Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

  624 Saint Judes Dr, 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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  /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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  /45

  $915,000

  • 3 Beds
  • 2 Baths
  • 1,941 Sq Ft

  100 Sands Point Rd Unit 303, Longboat Key, FL 34228

  Don’t miss this rare opportunity to call Sands Point home – an iconic beachfront community widely regarded as the crown jewel of Longboat Key. Nestled on the island’s coveted southernmost tip, this move-in-ready residence offers breathtaking sunsets and an unparalleled coastal lifestyle. Offered at an attractive value, this coastal escape presents a rare opportunity for the new owner to add their

  Diane Smith KELLER WILLIAMS ON THE WATER S

  100 Sands Point Rd Unit 303, 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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  /26

  $950,000

  • Land
  • 9,583 Sq Ft
  • $4,318,182 per Acre

  363 Firehouse Ln, Longboat Key, FL 34228

  "Create your ideal coastal retreat on the last available homesite in the peaceful and picturesque Conrad Beach enclave on Longboat Key. Just a 5-minute walk to the Gulf of Mexico and Whitney’s restaurant and a 2-minute drive to renowned restaurant Shore Longboat Key. This prime location offers easy access to pristine beaches and stunning sunsets. Conrad Beach is an award-winning neighborhood

  Adam Cuffaro MICHAEL SAUNDERS & COMPANY

  363 Firehouse Ln, Longboat Key, FL 34228
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  /33

  $995,000

  $400K PRICE DROP

  • Land
  • 10,890 Sq Ft
  • $3,980,000 per Acre

  660 Longview Dr, Longboat Key, FL 34228

  ESTATE SIZE BUILDABLE LOT 100' X 140' HOUSE TORN DOWN & SALT WATER CANAL FRONT LOT CLEARED & READY TO BUILD YOUR DREAM HOME IN DESIRABLE BUTTONWOOD HARBOUR NEIGHBORHOOD. Rare south end of Longboat Key location ( Sarasota County ) vacant lot with seawall situated Mid Longboat Key. Buttonwood Harbour neighborhood also has its own Boat Basin/Marina with community docks available for boats up to 28

  Maruta Miluns MICHAEL SAUNDERS & COMPANY

  660 Longview Dr, Longboat Key, FL 34228
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  /62

  $1,000,000

  • 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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  /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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  /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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  /9

  $850,000

  • Land
  • 7,405 Sq Ft
  • $5,000,000 per Acre

  610 Hibiscus Way, Longboat Key, FL 34228

  The best-priced homesite in The Preserve on Longboat Key—an exceptional opportunity to create your custom dream home in one of the island’s most picturesque neighborhoods. Nestled in the charming north village, this property offers both privacy and convenience. Walk to local favorites like Shore LBK, Mar Vista, and Whitney’s, enjoy the water with the neighborhood boat dock and ramp, or take your

  Rinat Sikdar COLDWELL BANKER REALTY

  610 Hibiscus Way, Longboat Key, FL 34228
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  /91

  $800,000

  $185K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,282 Sq Ft

  2326 Harbour Oaks Dr, Longboat Key, FL 34228

  Welcome to effortless coastal living in this beautifully maintained, fully furnished end-unit villa on Longboat Key. Offering nearly 2,400 square feet of thoughtfully designed living space, this exceptional residence combines the spaciousness and privacy of a single-family home with the convenience of maintenance-free living—all just moments from the Gulf's renowned white-sand beaches. From the

  Rachel Tritschler RE/MAX ALLIANCE GROUP

  2326 Harbour Oaks Dr, 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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  /52

  $724,900

  Open Sat 11AM - 2PM $104K 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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  /31

  $995,000

  • Land
  • 13,503 Sq Ft
  • $3,209,677 per Acre

  521 Neptune Ave, Longboat Key, FL 34228

  It's all about location! Rare south end longboat key (Sarasota County) vacant lot situated steps from your own private deeded beach access. Spectacular water views from this oversized lot that's ready to build the home of your dreams. There is nothing else like this piece of property on the market. Close to some of the best dining, shopping, schools, entertainment and world class beaches! In the

  Nathan Dunham W.I.T. REALTY LLC

  521 Neptune Ave, 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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