11,542

Longboat Key, FL Homes

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  • /51

    $1,075,000

    • 2 Beds
    • 2 Baths
    • 1,170 Sq Ft

    6925 Gulf of Mexico Dr Unit 24, Longboat Key, FL 34228

    Experience elevated coastal living in this beautifully renovated, second-floor beachfront condominium, offering sweeping Gulf views and the tranquility that comes with a higher vantage point. Nestled within the intimate, gated community of Sea Pines on the serene north end of Longboat Key, this end-unit residence effortlessly blends updated sophistication with the soothing rhythm of the sea. This

    Janet Walter MICHAEL SAUNDERS & COMPANY

    6925 Gulf of Mexico Dr Unit 24, Longboat Key, FL 34228
  • /25

    $9,000 per month

    • 2 Beds
    • 2 Baths
    • 1,409 Sq Ft
    • Condo for Rent

    1000 Longboat Club Rd, Longboat Key, FL 34228

    Welcome to your elevated coastal retreat on Longboat Key, located behind the gate of the prestigious Longboat Key Club. Available annually at $9,000/month or seasonally from November through April at $11,500/month, this fully renovated upper-floor residence offers refined living with sweeping Gulf and Bay views from two private balconies. Set within one of the island’s most exclusive beachfront

    Jenna Genovese KELLER WILLIAMS ON THE WATER S

    1000 Longboat Club Rd, Longboat Key, FL 34228
  • /2

    $750,000 Sold Jul 29, 2025

    • 1,900 Sq Ft
    • $395/SF
    • 136 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1963

    765 Saint Judes Dr N, Longboat Key, FL 34228

    BEST Waterfront Buy on all the Islands! Excellent Opportunity for Luxurious Waterfront Living. This exceptional property presents a unique chance to own a prime piece of real estate on the highly sought-after island of Longboat Key. A true island retreat, this stunning Canal-Front residence offers an ideal blend of comfort, elegance, and coastal charm. Featuring 4 bedrooms and 2 bathrooms, the

    Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

    765 Saint Judes Dr N, Longboat Key, FL 34228
    • /43

      Est $605,089 Not Listed For Sale

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

      4960 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228

      4960 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228
  • /68

    $1,250,000 Open Sun 1PM - 4PM

    • 3 Beds
    • 2 Baths
    • 1,484 Sq Ft

    4325 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

    Breathtaking Gulf Views & Sunset Serenity. Welcome to Tiffany Plaza, a mid-rise offering just 42 residences. This rarely available turnkey 3-bedroom, 2-bathroom beachfront condominium offers front-row seats to spectacular Longboat Key sunsets. The spacious residence includes a private balcony with spectacular water views, in-unit washer and dryer, secured elevator access, assigned covered parking

    Katia Balcazar COLDWELL BANKER REALTY

    4325 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
  • /39

    $5,500 per month

    • 2 Beds
    • 2 Baths
    • 1,401 Sq Ft
    • Condo for Rent

    3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228

    Available for season 2026! Experience resort-style living in this spacious 2-bedroom, 2-bath condo located in Beach Harbor Club on Longboat Key. Nestled along Sarasota Bay, this community offers refreshing bay breezes and an array of waterfront amenities, including kayak storage and lift, a boating and fishing pier, and private beach access to the pristine sands of the Gulf of Mexico. Relax by

    Maureen Plichta STRINGER MANAGEMENT INC

    3806 Gulf of Mexico Dr Unit C108, Longboat Key, FL 34228
  • /2

    $355,000 Sold Jul 29, 2025

    • 883 Sq Ft
    • $402/SF
    • 153 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1973

    605 Sutton Place Unit 205, Longboat Key, FL 34228

    Price improvement! Enjoy breathtaking views and Bay-to-Gulf amenities on Longboat Key in this direct bayfront unit. This furnished second-floor condominium shows beautifully, offering a serene retreat with stunning views of Sarasota Bay and exclusive access to a pristine stretch of Gulf beach. Inside, you'll find an inviting space with modern updates, including sleek black stainless steel Samsung

    Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

    605 Sutton Place Unit 205, Longboat Key, FL 34228
    • /78

      Est $760,711 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,312 Sq Ft

      4600 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

      4600 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
  • /100

    $1,139,000

    • 2 Beds
    • 2 Baths
    • 1,290 Sq Ft

    1000 Longboat Club Rd Unit 1105, Longboat Key, FL 34228

    Rarely available and beautifully renovated 11th floor Penthouse with breathtaking Gulf, Sunset and Bay views and ideally situated within a short beach walk between the popular Resort at Longboat Key Club and the luxurious St. Regis Resort. This island gem has brought many years of joy to the Seller based on its perfect South LBK beachside location and all it's resort style amenities. The sleek

    Tina Rudek Stark, PA ROSEBAY INTERNATIONAL REALTY, INC

    1000 Longboat Club Rd Unit 1105, Longboat Key, FL 34228
  • /74

    $17,000 per month

    • 4 Beds
    • 3 Baths
    • 2,447 Sq Ft
    • House for Rent

    830 Tarawitt Dr, Longboat Key, FL 34228

    Luxury and Coastal Elegance! This Stunning Turnkey Canal-Front Pool Home was Built in 2015. Situated on the Highly Desired North End of Longboat Key. Featuring 120 Feet of Beautiful Canal Frontage, A 10,000lbs Boat Lift and Deeded Beach Access only Steps Away! Truly A Boater's Paradise! At Almost 2500 Sq. Ft. of Interior Living, The Home Offers 4 Bedrooms, 3 Full Washrooms, 2 Balconies and

    Ian Greenberg BRISTA REALTY LLC

    830 Tarawitt Dr, Longboat Key, FL 34228
  • /2

    $975,000 Sold Jul 28, 2025

    • 1,446 Sq Ft
    • $674/SF
    • 7 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1970

    663 Penfield St, Longboat Key, FL 34228

    A Rare Longboat Key Value – Your Ideal Beach Retreat Awaits. Welcome to 663 Penfield Street—a hidden gem offering exceptional value on one of Longboat Key’s sought-after wide canals. This elevated three-bedroom, three-bath home boasts 1,446 sq ft of bright, open living space - emphasized by vaulted ceilings and skylights in the Kitchen/Great Room. Built in 1970 and enhanced with an elevator,

    Steve and Janet Walter MICHAEL SAUNDERS & COMPANY

    663 Penfield St, Longboat Key, FL 34228
    • /25

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 676 Sq Ft

      3710 Gulf of Mexico Dr Unit D22, Longboat Key, FL 34228

      3710 Gulf of Mexico Dr Unit D22, Longboat Key, FL 34228
  • /28

    $1,050,000

    • 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
  • /25

    $10,000 per month

    • 3 Beds
    • 2 Baths
    • 1,454 Sq Ft
    • House for Rent

    6979 Longboat Dr S, Longboat Key, FL 34228

    Escape to your own private garden oasis on beautiful Longboat Key. This home features lush tropical landscaping, a sparkling heated pool, and a spacious screened lanai perfect for outdoor dining and relaxation. Inside, enjoy a chef’s kitchen with premium appliances, including a Wolf range, and newly updated bedrooms and baths — the primary suite offers a brand-new king bed, while the kid’s room

    Rinat Sikdar COLDWELL BANKER REALTY

    6979 Longboat Dr S, Longboat Key, FL 34228
  • /2

    $589,000 Sold Jul 25, 2025

    • 1,440 Sq Ft
    • $409/SF
    • 140 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1991

    821 Evergreen Way, Longboat Key, FL 34228

    Stunning 2 bedroom condo just steps from Sarasota Bay - with one of the only 2 week minimum rentals allowed on Longboat Key. Welcome to your private retreat in the heart of Cedars East on Longboat Key! This beautifully updated 2 bedroom, 2 bathroom townhouse style condominium is located in the highly desirable bayfront section of the community - just 50 feet from the sparkling waters of

    Mary Moore WAGNER REALTY

    821 Evergreen Way, Longboat Key, FL 34228
    • /56

      Est $683,376 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 642 Sq Ft

      225 Sands Point Rd Unit 7304, Longboat Key, FL 34228

      225 Sands Point Rd Unit 7304, Longboat Key, FL 34228
  • /51

    $1,950,000

    • 3 Beds
    • 3.5 Baths
    • 1,880 Sq Ft

    540 Gulf Bay Rd, Longboat Key, FL 34228

    SPECTACULAR LONGBOAT KEY BEACH COMPOUND WITH DEEDED ACCESS TO THE GULF OF MEXICO! This FULLY ELEVATED beach home has been meticulously maintained, offers top of the line finishes, and is located just a short 4 minute walk with PRIVATE DEEDED BEACH ACCESS to the sparkling waters of the Gulf on LONGBOAT KEY! Surrounded by Joan Durante Park, this property offers the ultimate in privacy and

    Brett Coady PINEYWOODS REALTY LLC

    540 Gulf Bay Rd, Longboat Key, FL 34228
  • /30

    $8,000 per month

    • 2 Beds
    • 2 Baths
    • 1,235 Sq Ft
    • Condo for Rent

    2295 Gulf of Mexico Dr Unit 54S, Longboat Key, FL 34228

    SNOW BIRDS WELCOME! Fully Furnished and turnkey, immaculate 2 bedroom condo at The Islander Club with over 40 foot terrace. Renters have access to private beach and all ammenities; Clubhouse and Tennis Courts, New Pool, New Fitness Center, New Saunas. Islander Club is minutes to grocery, convenience stores, restaurants, The Longboat Key Club and a short distance to world famous St.

    Julie Lojacono Mackie COLDWELL BANKER REALTY

    2295 Gulf of Mexico Dr Unit 54S, Longboat Key, FL 34228
  • /2

    $475,000 Sold Jul 25, 2025

    • 1,441 Sq Ft
    • $330/SF
    • 163 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1969

    6750 Gulf of Mexico Dr Unit 153, Longboat Key, FL 34228

    EXCEPTIONAL value in this rarely available bayou AND canalfront Whitney Beach bayside SECOND floor condo. Partial GULF OF MEXICO gulf views from the 2nd bedroom and front foyer entry area too! If you listen closely you can even hear the sounds of the waves.Feel the bayou breeze from this beautifully updated 2nd-floor end-unit condo, where serene water views, deeded private beach access,

    Shayla Twit CORCORAN DWELLINGS REALTY

    6750 Gulf of Mexico Dr Unit 153, Longboat Key, FL 34228
    • /51

      Est $340,792 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 741 Sq Ft

      104 Twin Shores Blvd, Longboat Key, FL 34228

      104 Twin Shores Blvd, Longboat Key, FL 34228
  • /44

    $949,000 Open Sun 10AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,636 Sq Ft

    4234 Gulf of Mexico Dr Unit G2, Longboat Key, FL 34228

    PRICE REDUCTION! Waterfront 3BR Coastal Condo with Panoramic Bay Views! Experience the pinnacle of island living in this recently refreshed 3-bedroom, 2-bath condo in the highly desirable Pelican Harbour & Beach Club on Longboat Key. Located on the second floor, this light-filled end unit offers sweeping Sarasota Bay views from the living room, primary suite, and your private screened-in

    Shauna Ruby BLUESRQ REAL ESTATE INC

    4234 Gulf of Mexico Dr Unit G2, Longboat Key, FL 34228
  • /29

    $2,900 per month

    • 2 Beds
    • 2 Baths
    • 1,154 Sq Ft
    • Condo for Rent

    3320 Gulf of Mexico Dr Unit 208C, Longboat Key, FL 34228

    This fully renovated apartment is a sunlit, open-concept retreat with nearly every detail refreshed in 2024. The kitchen boasts custom cabinetry, quartz countertops, and a Frigidaire Gallery appliances. The second room with two beds is perfect for guests. Flooring in light wood runs throughout, and hurricane-impact floor and windows offer peace of mind. The community offers 800 feet of bayfront,

    Valeria Fucaraccio Benesch Brokers, LLC

    3320 Gulf of Mexico Dr Unit 208C, Longboat Key, FL 34228
  • /2

    $2,175,000 Sold Jul 25, 2025

    • 2,375 Sq Ft
    • $916/SF
    • 158 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1991

    545 Sanctuary Dr Unit A803, Longboat Key, FL 34228

    Discover the pinnacle of coastal luxury in this magnificent 8th-floor northeast corner residence, perfectly positioned within one of Longboat Key’s most sought-after communities. Revel in sweeping, unobstructed views of the Gulf of Mexico, Sarasota Bay, Downtown Sarasota, theLongboat Key golf course and beyond. With a generous 2,375-square-foot floor plan, this exquisitely appointed home

    Louis Wery PREMIER SOTHEBY'S INTERNATIONAL REALTY

    545 Sanctuary Dr Unit A803, Longboat Key, FL 34228
    • /42

      Est $382,490 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 809 Sq Ft

      102 Twin Shores Blvd, Longboat Key, FL 34228

      102 Twin Shores Blvd, Longboat Key, FL 34228
  • /57

    $1,999,000

    • 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

    John Donato JOHN DONATO REAL ESTATE INC

    5920 Gulf of Mexico Dr, Longboat Key, FL 34228
  • /19

    $8,700 per month

    • 2 Beds
    • 2 Baths
    • 1,445 Sq Ft
    • Condo for Rent

    Unlisted Address

    NOW AVAILABLE FOR THE 2026 SEASON: Take a 60 second stroll across the street to the Gulf Beach from this Very Popular and Beautiful Renovated unit with an onsite heated pool and outdoor shower. Enjoy Peek-a-views of the gulf beach right from the Living Room Sofa, or Brand New Private Wrap Around Balcony to enjoy sunsets that are truly amazing! There's truly Nothing else like it on the island.

    Monique Holston-Greene COLDWELL BANKER REALTY

    Unlisted Address
  • /2

    $350,000 Sold Jul 24, 2025

    • 1,245 Sq Ft
    • $281/SF
    • 28 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1968

    754 Spanish Dr S Unit 754, Longboat Key, FL 34228

    Welcome to Spanish Main Yacht Club, a sought-after 55+ waterfront community on Longboat Key, where coastal living meets exceptional value. Priced at $359,000, this 2-bedroom, 2-bath villa-style condo offers 1,677 SqFt of interior space—1,357 of it under air—and presents a unique opportunity to craft your dream home in a prime location. This stand-alone unit has already undergone key

    Geoff Scalera AUM FLORIDA REAL ESTATE LLC

    754 Spanish Dr S Unit 754, Longboat Key, FL 34228
    • /60

      Est $799,005 Not Listed For Sale

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

      4960 Gulf of Mexico Dr Unit 306, Longboat Key, FL 34228

      4960 Gulf of Mexico Dr Unit 306, Longboat Key, FL 34228
  • /59

    $1,200,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,422 Sq Ft

    4968 Gulf of Mexico Dr Unit Villa 22, Longboat Key, FL 34228

    Breathtaking Sarasota Bay views can be yours! This rare to find 3BR/2BA waterfront villa offers unobstructed water views and a dream coastal lifestyle. With an extraordinary location on a serene peninsula, this ground-level, maintenance-free residence lives like a single-family home—without the upkeep or the price. Step outside to your private waterfront patio, with dolphins, manatees, and

    Eileen Gillen COLDWELL BANKER REALTY

    4968 Gulf of Mexico Dr Unit Villa 22, Longboat Key, FL 34228
  • /46

    $7,500 per month

    • 2 Beds
    • 2 Baths
    • 1,290 Sq Ft
    • Condo for Rent

    1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228

    Welcome to Pearl On The Key, your coastal sanctuary Professionally Managed by Gulf Coast Vacation Rentals, at Privateer, an exclusive beachfront community nestled on the pristine shores of Longboat Key. This 2-bedroom, 2-bathroom 7th floor condo offers breathtaking Gulf views from every room, elegant interiors, and access to resort-style amenities—making it the perfect destination for your next

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1050 Longboat Club Rd Unit 702, Longboat Key, FL 34228
  • /2

    $600,000 Sold Jul 22, 2025

    • 928 Sq Ft
    • $647/SF
    • 91 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1978

    1945 Gulf of Mexico Dr Unit M2310, Longboat Key, FL 34228

    NEW PRICE:ONLY FULL DIRECT WATER VIEW AT SEAPLACE: Welcome to paradise, from the moment you open the front door your eyes are drawn to the magnificent unobstructed views of the azure waters of the Gulf of Mexico. You will be working with a clean slate to decorate and furnish to your own personal taste. New 20" x 20" off white tiles throughout the main rooms and electronic shutters in the living

    Sandra Endres COLDWELL BANKER REALTY

    1945 Gulf of Mexico Dr Unit M2310, Longboat Key, FL 34228
    • /53

      Est $659,040 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 896 Sq Ft

      4401 Gulf of Mexico Dr Unit 503, Longboat Key, FL 34228

      4401 Gulf of Mexico Dr Unit 503, Longboat Key, FL 34228
  • /67

    $2,345,000

    • 4 Beds
    • 4.5 Baths
    • 4,048 Sq Ft

    3521 Fair Oaks Ln, Longboat Key, FL 34228

    Imagine waking up to manicured fairways and ending your day with toes in the sand. Ideal for seasonal living, or full-time escape, this Longboat Key home offers a refined island lifestyle with beautiful golf course views and private gulf beach access. With over 1300 miles of scenic coastline, Florida is a no income tax state that offers beautiful beaches, year-round out-door activities, mild

    Kathleen Wingate PREMIER SOTHEBY'S INTERNATIONAL REALTY

    3521 Fair Oaks Ln, Longboat Key, FL 34228
  • /21

    $5,000 per month

    • 2 Beds
    • 2.5 Baths
    • 1,590 Sq Ft
    • Townhouse for Rent

    1912 Harbourside Dr Unit 603, Longboat Key, FL 34228

    Turnkey Townhouse on Longboat Key – Resort-Style Living! Live the island dream in this beautifully furnished 2-bedroom, 2.5-bathroom townhouse in the exclusive gated community of Fairway Bay. Located on picturesque Longboat Key, this bright and spacious home offers two ensuite bedrooms for ultimate comfort and privacy. Enjoy private beach access to the stunning Gulf of Mexico, take a dip

    Victoria Campbell LPT REALTY LLC

    1912 Harbourside Dr Unit 603, Longboat Key, FL 34228
  • /2

    $790,000 Sold Jul 21, 2025

    • 1,559 Sq Ft
    • $507/SF
    • 55 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1975

    4600 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

    Exquisite Bayfront Living with Unparalleled Panoramic ViewsImmerse yourself in breathtaking day-to-night bay views from every room in this impeccably maintained 2-bedroom, 2-bathroom corner end-unit condo (1,523 SF). Boasting the largest floor plan in the community, this elevated 2nd-floor retreat, effortlessly combines elegance, comfort, and the beauty of its natural surroundings —accessible

    Oday Marogi KELLER WILLIAMS ON THE WATER S

    4600 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
    • /80

      Est $2,999,167 Not Listed For Sale

      • 2 Beds
      • 4.5 Baths
      • 2,965 Sq Ft

      1241 Gulf of Mexico Dr Unit 707, Longboat Key, FL 34228

      1241 Gulf of Mexico Dr Unit 707, Longboat Key, FL 34228
  • /34

    $949,000

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

    2301 Gulf of Mexico Dr Unit 36, Longboat Key, FL 34228

    One or more photo(s) has been virtually staged. Front-row Gulf views and beachfront living set this 2BR/2BA residence apart at the Islander Club of Longboat Key. With over 1,235 sq. ft. of light-filled space set just above the sand, savor sweeping vistas of the shoreline and SPECTACULAR SUNSETS over the Gulf. White tile floors and neutral tones throughout create a sense of openness that draws

    Bruce Myer COLDWELL BANKER REALTY

    2301 Gulf of Mexico Dr Unit 36, Longboat Key, FL 34228
  • /56

    $17,500 per month

    • 3 Beds
    • 2 Baths
    • 1,871 Sq Ft
    • House for Rent

    613 Buttonwood Dr, Longboat Key, FL 34228

    Available for season 2026This home has a split plan, generous size bedrooms and walk-in closets with a coastal theme flare. Open floor concept with formal dining. The kitchen as the heart of the home is expertly appointed with everything you will need for your home cooked meals. Head outside to the brand new beautiful pool and spa. One end features a soaking or sunbathing area, then step

    Jennifer LeBlanc PRECISE REALTY CORP

    613 Buttonwood Dr, Longboat Key, FL 34228
  • /2

    $1,050,000 Sold Jul 21, 2025

    • 1,579 Sq Ft
    • $665/SF
    • 127 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1978

    650 Penfield St, Longboat Key, FL 34228

    An ELEVATED waterfront home uniquely positioned in an exceptional location on the fabulous north end of Longboat Key. This laid back, friendly, single-family neighborhood adds to the charm. With no high rises here, your morning strolls on the beach are only crowded by the shore birds. Surrounded by trees on all sides and sitting on a 10,230sf lot, when you enter into this home, you truly have a

    JoDene Moneuse MICHAEL SAUNDERS & COMPANY

    650 Penfield St, Longboat Key, FL 34228
    • /75

      Est $4,512,168 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,122 Sq Ft

      4975 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

      4975 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

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