Longboat Key, FL Homes

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  /43

  $575,000

  • 2 Beds
  • 2 Baths
  • 1,257 Sq Ft

  2039 Gulf of Mexico Dr Unit G3207, Longboat Key, FL 34228

  THIS IS THE LARGEST 2 BEDROOM 2 BATH FLOOR PLAN IN SEAPLACE! Located on the second floor of the G3 building, this home is move in ready! The previous den has been enclosed for a proper bedroom and updated! The primary bedroom and bathroom have both been updated. Updated lighting, updated baseboards, no carpet, new hurricane rated sliders and windows! Plantation shutters are added for easy care

  Diane Fogo Harter MICHAEL SAUNDERS & COMPANY

  2039 Gulf of Mexico Dr Unit G3207, Longboat Key, FL 34228
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  /67

  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • House for Rent

  4780 Gulf of Mexico Dr, Longboat Key, FL 34228

  BONUS FREE RENTAL DAYS! AVAILABLE 12/26/2025-1/31/2026 ONLY! Stay through New Years Eve for Free as a bonus. Fully Booked for the remainder of the 2026 season. Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January 2025! Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets

  Debby McCaig COLDWELL BANKER REALTY

  4780 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /65

  $1,195,000 Sold Mar 10, 2025

  3427 Winding Oaks Dr Unit 14, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,555 Sq Ft
  • Built 1988

  Last Sold Summary

  • $468/SF
  • 30 Days On Market

  Current Estimated Value $1,121,845

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  3427 Winding Oaks Dr Unit 14, Longboat Key, FL 34228
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  /42

  Est $344,729 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
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  /57

  $8,250,000

  • 4 Beds
  • 4.5 Baths
  • 4,630 Sq Ft

  5005 Gulf of Mexico Dr Unit 4, Longboat Key, FL 34228

  Designed by award-winning architect, John Cooney, and built by Sarasota’s premier coastal homebuilder, Perrone Construction, this mid-Key classic is simply among Longboat Key’s finest homes.Steps from the beach and with expansive Gulf and Bay views, this masterpiece offers more than 4300 square feet of refined interiors on the main living floors together with multiple large lanais and

  Reid Murphy DEVELOPERS REALTY LBK, INC

  5005 Gulf of Mexico Dr Unit 4, Longboat Key, FL 34228
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  /35

  $5,500 per month

  • 2 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Condo for Rent

  3440 Gulf of Mexico Dr Unit 9, Longboat Key, FL 34228

  AVAILABLE Dec. 2025-April 2026, 2 mos. min. This is a second floor walk up, two bedroom and den, two bathroom unit with over 1,600 square feet of interior living space. There is a private screened balcony/lanai and aa staircase entrance to the front door of the unit. The unit has partial water views from the living room, dining room, den, and the screened balcony and exterior open balcony/lanai

  Brenda Cozy COLDWELL BANKER REALTY

  3440 Gulf of Mexico Dr Unit 9, Longboat Key, FL 34228
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  /2

  $1,025,000 Sold Feb 14, 2025

  1485 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 1,551 Sq Ft
  • Built 1981

  Last Sold Summary

  • 6% Below List Price
  • $661/SF
  • 32 Days On Market

  Current Estimated Value $954,042

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  1485 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  /60

  Est $755,256 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
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  /35

  $1,299,000

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

  1055 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

  This direct Gulf-front residence at Beachplace offers an extraordinary opportunity to enjoy the very best of Longboat Key’s beachfront lifestyle. Perfectly positioned to capture unobstructed views of the Gulf of Mexico, this furnished two-bedroom home combines a serene coastal retreat with strong rental potential—producing an average of $70,000 annually in gross rentals. Whether you envision it

  Roger Pettingell COLDWELL BANKER REALTY

  1055 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
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  /42

  $10,000 per month

  • 3 Beds
  • 3 Baths
  • 1,744 Sq Ft
  • House for Rent

  2823 Gulf of Mexico Dr, Longboat Key, FL 34228

  Available beginning June 1st, 2026. Welcome to beachfront paradise on Longboat Key! This outstanding location offers a rare opportunity to enjoy coastal living with breathtaking views of the shoreline. Nestled along the pristine shores of Longboat Key, this three-bedroom, three-bathroom home invites you to experience the ultimate beachfront lifestyle. Relax under the sun, unwind to the sound of

  Michael Cella CELLA'S REAL ESTATE INC

  2823 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /37

  $765,000 Sold Mar 13, 2025

  3070 Grand Bay Blvd Unit 625, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • Built 1995

  Last Sold Summary

  • $600/SF
  • 7 Days On Market

  Current Estimated Value $722,562

  Last Listing Agent Lee Mirman INVESTMENTS IN SARASOTA

  3070 Grand Bay Blvd Unit 625, Longboat Key, FL 34228
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  /53

  Est $649,898 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
• 

  

  /20

  $995,000

  • Land
  • 0.16 Acre
  • $6,218,750 per Acre

  6800 Longboat Dr S, Longboat Key, FL 34228

  This lot is located in The Preserve at Longbeach with plans and design already to go, an exclusive enclave of 12 new homes, light filled and luxurious contemporary homes. Refinement meets relaxation at the north end of LBK in Longbeach Village - where beach-to-bay access with waterfront amenities, al fresco dining, multiple kayak launch points, a neighborhood boat dock and ramp, and a

  Reid Murphy DEVELOPERS REALTY LBK, INC

  6800 Longboat Dr S, Longboat Key, FL 34228
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  /16

  $8,000 per month

  • 2 Beds
  • 2 Baths
  • 1,941 Sq Ft
  • Condo for Rent

  100 Sands Point Rd Unit 223, Longboat Key, FL 34228

  Location! Location! Location for Winter 2026 Rental Season!Gulf-front condominium complex “Sands Point” sits on the southernmost tip of Longboat Key. This location allows you to save time in traffic. Nestled adjacent to the iconic Longboat Key Resort, this Mid-Century modern 77-unit complex boosts impeccable views, gorgeous landscaping, a full-time maintenance crew and your own covered

  Diane Smith KELLER WILLIAMS ON THE WATER S

  100 Sands Point Rd Unit 223, Longboat Key, FL 34228
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  /2

  $925,000 Sold Jul 10, 2025

  5055 Gulf of Mexico Dr Unit 232, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,624 Sq Ft
  • Built 1973

  Last Sold Summary

  • 27% Below List Price
  • $570/SF
  • 25 Days On Market

  Current Estimated Value $965,000

  Last Listing Agent Nathan Mathers PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5055 Gulf of Mexico Dr Unit 232, Longboat Key, FL 34228
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  /80

  Est $2,784,682 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
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  /66

  $459,000

  • 2 Beds
  • 2 Baths
  • 1,270 Sq Ft

  576 Sutton Place, Longboat Key, FL 34228

  Lovely, turnkey villa that is truly Martha Stewart–perfect, offering the coveted Bay-to-Beach lifestyle on Longboat Key. This pet-friendly, free-standing end-unit “ Villa” features an enclosed den/Florida room where you can relax and enjoy birds, lush greenery, and serene surroundings relax knowing the hurricane impact windows completely ensconce you to completely relax ...A spacious family room

  Kathy Callahan MICHAEL SAUNDERS & COMPANY

  576 Sutton Place, Longboat Key, FL 34228
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  /57

  $11,500 per month

  • 3 Beds
  • 3.5 Baths
  • 3,101 Sq Ft
  • House for Rent

  2254 Harbour Court Dr, Longboat Key, FL 34228

  Nestled on the tranquil waterfront of Longboat Key, this stunning residence offers the ultimate coastal lifestyle. With direct water access and a private dock, boating and jet skiing are right at your doorstep. Two floating jet ski docks can also accommodate dinghies, making this property a boater’s dream. The home is ideally situated beside the golf course, blending serene water views with lush

  Alex Larchenko KELLER WILLIAMS ON THE WATER S

  2254 Harbour Court Dr, Longboat Key, FL 34228
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  /2

  $350,000 Sold Sep 15, 2025

  655 Spanish Way, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,241 Sq Ft
  • Built 1968

  Last Sold Summary

  • 11% Below List Price
  • $282/SF
  • 74 Days On Market

  Current Estimated Value $357,748

  Last Listing Agent Kimberly Freiwald PREMIER SOTHEBY'S INTERNATIONAL REALTY

  655 Spanish Way, Longboat Key, FL 34228
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  /75

  Est $3,950,577 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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  /72

  $1,999,000

  • 3 Beds
  • 3 Baths
  • 2,122 Sq Ft

  775 Longboat Club Rd Unit 203, Longboat Key, FL 34228

  Welcome to your dream beachfront retreat, nestled behind the exclusive gates of the prestigious Longboat Key Club. This exquisite 3-bedroom, 3-bathroom Gulf-front residence captures breathtaking, unobstructed views of the sparkling turquoise waters of the Gulf from every room—an ever-changing canvas of sunlight, sea, and sky. From the moment you enter, you're greeted by expansive walls of glass

  Courtney Tarantino COLDWELL BANKER REALTY

  775 Longboat Club Rd Unit 203, Longboat Key, FL 34228
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  /71

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,561 Sq Ft
  • Condo for Rent

  5757 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

  Beautiful completely remodeled 2-bedroom, 2-bathroom Tropical Oasis on Longboat Key. Relax and enjoy the Florida lifestyle at its best with stunning gulf views from this gorgeous second floor retreat. Just steps to the beautiful white sand and warm gulf waters. Upgrades include new open floor plan with spacious rooms decorated in a soothing coastal color palette. Heightened ceilings, hardwood

  Roxanne Klopp JENNETTE PROPERTIES, INC.

  5757 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
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  /2

  $545,000 Sold Mar 19, 2025

  3810 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Built 1970

  Last Sold Summary

  • 22% Below List Price
  • $400/SF
  • 42 Days On Market

  Current Estimated Value $515,328

  Last Listing Agent Susan Mondello MICHAEL SAUNDERS & COMPANY

  3810 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
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  /63

  Est $859,323 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,224 Sq Ft

  2213 Harbourside Dr Unit 303, Longboat Key, FL 34228

  2213 Harbourside Dr Unit 303, Longboat Key, FL 34228
• 

  

  /39

  $1,550,000

  • 2 Beds
  • 2 Baths
  • 1,551 Sq Ft

  1701 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228

  AQUARIUS CLUB – This exquisitely renovated fourth floor residence is situated within an exclusive beachfront boutique community on Longboat Key, located directly adjacent to the new Five Diamond St. Regis Resort. Modern design blends seamlessly with coastal elegance in the two-bedroom, two-bathroom retreat. The meticulously updated interior offers 1,551 Sq. ft of open living space, with privacy

  Doug Parks MICHAEL SAUNDERS & COMPANY

  1701 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228
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  /40

  $12,000 per month

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

  1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228

  Available for 2026 and 2027 Season!! Welcome to The Privateer, one of Longboat Key’s most coveted beachfront communities. This 10th-floor residence offers a rare opportunity to experience refined coastal living with panoramic, unobstructed views of the Gulf of Mexico. From the moment you step inside, you are greeted by a light-filled interior that opens seamlessly to two private balconies, each

  Jenna Genovese KELLER WILLIAMS ON THE WATER S

  1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228
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  /2

  $625,000 Sold Mar 07, 2025

  2215 Harbourside Dr Unit 304, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,906 Sq Ft
  • Built 1984

  Last Sold Summary

  • 11% Below List Price
  • $328/SF
  • 40 Days On Market

  Current Estimated Value $595,950

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  2215 Harbourside Dr Unit 304, Longboat Key, FL 34228
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  /48

  Est $1,168,024 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,678 Sq Ft

  3437 Winding Oaks Dr Unit 19, Longboat Key, FL 34228

  3437 Winding Oaks Dr Unit 19, Longboat Key, FL 34228
• 

  

  /58

  $3,450,000

  • 2 Beds
  • 4 Baths
  • 2,634 Sq Ft

  435 L Ambiance Dr Unit J704, Longboat Key, FL 34228

  Rarely available, this 7th floor, 3 bedroom, 3 bath condo with perfect east/west views offers total privacy. Relax, unwind, and enjoy the magnificent views of the pristine sandy beach and the blue waters of the Gulf of Mexico from this unit in L ambiance. Turn around to the east and watch the boats on Sarasota Bay, and enjoy the lush fairways of the Longboat Key Golf Club. This well-designed unit

  Reid Murphy DEVELOPERS REALTY LBK, INC

  435 L Ambiance Dr Unit J704, Longboat Key, FL 34228
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  /59

  $11,000 per month

  • 3 Beds
  • 3 Baths
  • 2,772 Sq Ft
  • House for Rent

  3390 Bayou Sound, Longboat Key, FL 34228

  **This is a 2 month minimum vacation rental**Welcome to 3390 Bayou Sound, located within the exclusive, gated community of Bay Isles on picturesque Longboat Key. This prime location offers access to world-renowned beaches, a marina, golf courses, biking trails, and tennis facilities. Nestled on an oversized, beautifully landscaped corner lot in the Bayou section of Bay Isles, this

  Jennifer LeBlanc PRECISE REALTY CORP

  3390 Bayou Sound, Longboat Key, FL 34228
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  /2

  $460,000 Sold May 07, 2025

  7119 Longboat Dr E, Longboat Key, FL 34228

  • 2 Beds
  • 1 Bath
  • 910 Sq Ft
  • Built 1930

  Last Sold Summary

  • 26% Below List Price
  • $505/SF
  • 37 Days On Market

  Current Estimated Value $513,953

  Last Listing Agent JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  7119 Longboat Dr E, Longboat Key, FL 34228
• 

  

  /25

  Est $1,372,944 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,180 Sq Ft

  1902 Harbour Links Cir Unit 16, Longboat Key, FL 34228

  1902 Harbour Links Cir Unit 16, Longboat Key, FL 34228
• 

  

  /44

  $995,000

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

  4835 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. Experience the ultimate beachfront lifestyle in this stunning 1,393 sq. ft. 2-bedroom, 2-bathroom retreat on Longboat Key. Perfectly positioned on the third floor, this home offers amazing views of the beautiful beaches and the endless Gulf horizon—visible from nearly every room! Wake up to the sound of waves in the master suite, where sliding doors

  Donna Wrobel BERKSHIRE HATHAWAY HOMESERVICE

  4835 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
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  /13

  $3,000 per month

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft
  • Condo for Rent

  3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228

  LONGBOAT KEY...Lovely 2 bedroom 2 bath condo directly across from the private beach. Updated kitchen with stainless steel appliances and master and guest bathrooms with ceramic tile. Split floor plan, master suite with a king size bed and the guest room has bunk beds with one single bed and one full size bed. Spacious, open, light and bright. Very well maintained GULF TO BAY complex with lush

  Teresa Ribaudo JENNETTE PROPERTIES INC

  3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228
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  /2

  $2,200,000 Sold Jan 10, 2025

  3030 Grand Bay Blvd Unit 343, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,550 Sq Ft
  • Built 1998

  Last Sold Summary

  • 4% Below List Price
  • $863/SF
  • 13 Days On Market

  Current Estimated Value $1,974,803

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  3030 Grand Bay Blvd Unit 343, Longboat Key, FL 34228
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  /2

  Est $1,531,442 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,476 Sq Ft

  1915 Harbour Links Cir Unit 6, Longboat Key, FL 34228

  1915 Harbour Links Cir Unit 6, Longboat Key, FL 34228
• 

  

  /52

  $975,000

  • 2 Beds
  • 2 Baths
  • 961 Sq Ft

  5125 Gulf of Mexico Dr Unit 7, Longboat Key, FL 34228

  Nestled in the heart of Longboat Key, this exceptional two-bedroom, two-bathroom beachfront condo offers a rare blend of luxury, comfort, and high rental potential. Situated within the meticulously maintained Seagrape Inn, this turnkey furnished unit is an investor’s dream, boasting a potential gross annual revenue of $108,000 and a net operating income of $66,000. The Seagrape Inn's lush

  Patrick Brogley KELLER WILLIAMS ON THE WATER S

  5125 Gulf of Mexico Dr Unit 7, Longboat Key, FL 34228
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  /68

  $29,000 per month

  • 5 Beds
  • 5.5 Baths
  • 4,858 Sq Ft
  • House for Rent

  591 Putting Green Ln, Longboat Key, FL 34228

  LONGBOAT KEY...If you're looking for a Luxury winter vacation home, stop searching. You have just found the perfect house located on a private & peaceful cul-de-sac. This beautiful 5 bedroom, 5.1 bathrooms has everything you would want and more with all the comforts of home. All new furniture throughout in every room. Primary, 1st & 2nd bedrooms all have king size beds. Bedrooms 3 & 4 have twin

  Teresa Ribaudo JENNETTE PROPERTIES INC

  591 Putting Green Ln, Longboat Key, FL 34228
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  /2

  $2,700,000 Sold Jul 14, 2025

  549 Sloop Ln, Longboat Key, FL 34228

  • 4 Beds
  • 3.5 Baths
  • 4,127 Sq Ft
  • Built 2000

  Last Sold Summary

  • 37% Below List Price
  • $654/SF
  • 255 Days On Market

  Current Estimated Value $3,068,955

  Last Listing Agent Tracey Stetler COLDWELL BANKER REALTY

  549 Sloop Ln, Longboat Key, FL 34228
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  /66

  Est $483,260 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,399 Sq Ft

  583 Spanish Dr S Unit 129, Longboat Key, FL 34228

  583 Spanish Dr S Unit 129, Longboat Key, FL 34228

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