Longboat Key, FL Homes

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  $9,875,000

  • 4 Beds
  • 4.5 Baths
  • 4,338 Sq Ft

  600 Wedge Ln, Longboat Key, FL 34228

  Sarasota Bay Waterfront Masterpiece – Perched on one of the most coveted point lots in Country Club Shores with Deeded Beach Access, this elevated, 2016 coastal contemporary offers 260 feet of unobstructed views across Sarasota Bay, the city skyline, and the Ringling Bridge. Designer-furnished and move-in ready, the pinnacle of waterfront luxury. Built with resilience and sophistication, the home

  Debra Lichter SARASOTA BEACH TO BAY INC

  600 Wedge Ln, Longboat Key, FL 34228
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  /24

  $5,000 per month

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

  1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228

  Available 07/15/2025 through 12/30/2025. LEASED SEASON JAN, 2026 THROUGH MARCH, 2026. This residence is gulf and bay views through your hurricane sliding doors and a view from every room. Pristine sandy beaches from a luxurious direct front gulf complex. Located in the gated Longboat Key club and Resort. A spacious 2 bedroom, 2 bathroom unit turn-key furnished. Both bedrooms have private lanais,

  Marni Hayden CHROME REALTY LLC

  1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
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  $9,795,000 Sold Jun 27, 2025

  1561 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 4,992 Sq Ft
  • Built 2024

  Last Sold Summary

  • $1,962/SF
  • 0 Days On Market

  Last Listing Agent Georgia Kopelousos COLDWELL BANKER REALTY

  1561 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
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  /63

  Est $1,462,542 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,530 Sq Ft

  621 Buttonwood Dr, Longboat Key, FL 34228

  621 Buttonwood Dr, Longboat Key, FL 34228
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  /65

  $2,999,999

  • 3 Beds
  • 3.5 Baths
  • 2,780 Sq Ft

  455 Longboat Club Rd Unit 8, Longboat Key, FL 34228

  Tucked within the private enclave of the Longboat Key Club, this beautifully reimagined penthouse at The Pierre offers an inspired blend of Manhattan sophistication and relaxed coastal charm. This three-bedroom, three-and-a-half-bath residence has been fully renovated to perfection, showcasing a fresh, contemporary design with sleek finishes, designer lighting, and open, airy living spaces that

  Gina Ursini BRISTA REALTY LLC

  455 Longboat Club Rd Unit 8, Longboat Key, FL 34228
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  /42

  $10,000 per month

  • 3 Beds
  • 3 Baths
  • 2,698 Sq Ft
  • Condo for Rent

  1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228

  LONGBOAT KEY'S SEAPLACE Enjoy the tropical sea breezes and the magical Water Views from this custom designed THREE BEDROOM spacious corner unit. Beautiful wrap around Lanai terraces with panoramic scenery of the GULF OF MEXICO. Primary Suite-King Bed, Bedroom #2 Suite-King Bed, Bedroom #3- two twin beds. Seaplace is located close to shopping and restaurants and just minutes to ST Armand's Circle

  Jane Hunter JENNETTE PROPERTIES INC

  1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
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  /2

  $505,000 Sold Dec 15, 2025

  1945 Gulf of Mexico Dr Unit M2207, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,076 Sq Ft
  • Built 1978

  Last Sold Summary

  • 20% Below List Price
  • $469/SF
  • 139 Days On Market

  Last Listing Agent Harold Kaufman PREFERRED SHORE LLC

  1945 Gulf of Mexico Dr Unit M2207, Longboat Key, FL 34228
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  /61

  Est $1,122,836 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,465 Sq Ft

  3115 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  3115 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  /5

  $1,295,000

  • Land
  • 0.3 Acre
  • $4,316,667 per Acre

  591 Russell St, Longboat Key, FL 34228

  Beautiful, estate sized corner lot north end of Longboat Key in the historic and charming Village of Longbeach. Water & underground electric in place and property is prepped to build on. Plenty of room for your pool, tennis & pickleball courts. A community with one of a kind restaurants, some with Michelin stars, Diamond rated hotels with spectacular amenities and the best of the best golf

  Jonathan Minerick HOMECOIN.COM

  591 Russell St, Longboat Key, FL 34228
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  /75

  $11,550 per month

  • 2 Beds
  • 2 Baths
  • 1,657 Sq Ft
  • House for Rent

  500 Schooner Ln, Longboat Key, FL 34228

  Booked May 1st- June 16th, July13th-July 27th, Nov 14th-rest of 2025. Booked January, May, October, and Dec 2026 through February 2027, Must be a one month minimum stay during seasonal months and 2 week minimum stay out of season. Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Every detail was

  Jennifer LeBlanc PRECISE REALTY CORP

  500 Schooner Ln, Longboat Key, FL 34228
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  /2

  $1,000,000 Sold Apr 25, 2025

  3360 Bayou, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,922 Sq Ft
  • Built 1981

  Last Sold Summary

  • 23% Below List Price
  • $520/SF
  • 5 Days On Market

  Current Estimated Value $1,330,510

  Last Listing Agent Stephen Strong MICHAEL SAUNDERS & COMPANY

  3360 Bayou, Longboat Key, FL 34228
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  /45

  Est $1,076,528 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,314 Sq Ft

  4401 Gulf of Mexico Dr Unit 807, Longboat Key, FL 34228

  4401 Gulf of Mexico Dr Unit 807, Longboat Key, FL 34228
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  /32

  $369,000

  • 2 Beds
  • 1 Bath
  • 680 Sq Ft

  3710 Gulf of Mexico Dr Unit E22, Longboat Key, FL 34228

  BEAUTIFULLY REMODLED: This home is the epitome of simple elegance. It has been remodeled to create a home that is open and full of light. It features a large Living Room with a wall-mounted TV and a fireplace; a kitchen that has all new cabinets and granite counter tops; two Bedrooms and a full Bath with a step-in shower. Grayhawk windows were installed three years ago. In addition, there is

  Bill Shuttleworth EDGEWATER REAL ESTATE, INC

  3710 Gulf of Mexico Dr Unit E22, Longboat Key, FL 34228
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  /55

  $11,950 per month

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • Condo for Rent

  2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228

  Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you step into this fourteen-floor residence at Sea Gate, you will be captivated by the breathtaking views from every room.Relax on the lanai with new glass railings and enjoy your morning coffee while you plan your daily adventures. This beautifully renovated two-bedroom,

  Andrey markov ANMARK REALTY LLC

  2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
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  /48

  $1,170,000 Sold Mar 11, 2025

  4825 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • Built 1970

  Last Sold Summary

  • 8% Below List Price
  • $840/SF
  • 94 Days On Market

  Current Estimated Value $1,080,382

  Last Listing Agent Michael Albano, PA COLDWELL BANKER REALTY

  4825 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
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  /28

  Est $2,892,077 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,045 Sq Ft

  1241 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228

  1241 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228
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  /85

  $2,799,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 2,848 Sq Ft

  6810 Longboat Dr S, Longboat Key, FL 34228

  All new in 2024, this dream retreat is uniquely positioned in the highly sought after “Village” of Longboat Key, a neighborhood known for its quaint charm and vibrant community atmosphere. Featuring 4 bedrooms and 4 and a half baths in open and light filled rooms, a backyard oasis with a pool and outdoor kitchen, high impact windows and doors throughout, 1230 sq ft of porches and balconies and an

  JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  6810 Longboat Dr S, Longboat Key, FL 34228
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  /55

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,133 Sq Ft
  • Condo for Rent

  3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228

  Welcome to Sunset On The Gulf! This gorgeous 2-bedroom, 2-bathroom, third-floor, corner condo offers the perfect location. Located between the bay and the beach, you are bound to have endless adventures. The community of Beach Harbor Club offers resort-style living at its finest. There is a large community pool, a clubhouse with a bar, and a fitness center to get in your morning exercises! You

  Andy Moore GULF COAST REALTY & MANAGEMENT

  3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
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  /2

  $640,000 Sold Oct 07, 2025

  4825 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • Built 1970

  Last Sold Summary

  • 8% Below List Price
  • $459/SF
  • 11 Days On Market

  Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4825 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
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  /67

  Est $1,504,266 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,724 Sq Ft

  3637 Fair Oaks Place Unit 1, Longboat Key, FL 34228

  3637 Fair Oaks Place Unit 1, Longboat Key, FL 34228
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  /36

  $4,499,000

  • 3 Beds
  • 2 Baths
  • 1,173 Sq Ft

  2819 Gulf of Mexico Dr, Longboat Key, FL 34228

  BEACH FRONT OPPORTUNITY on Longboat Key! Rare chance to own DIRECT GULF FRONT property on the coveted south end of Longboat Key in Sarasota county. This charming, 1955 beach cottage sustained significant hurricane damage and is now being sold AS-IS for land value only. No HOA fees! Build your dream coastal retreat on this prime GULF-front lot and enjoy breathtaking sunsets, white-sand beaches-

  Jenn Flanders SERHANT

  2819 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /39

  $30,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,230 Sq Ft
  • House for Rent

  6925 Longboat Dr S, Longboat Key, FL 34228

  Available May-December with a 90 Day minimum at $15,550 per month plus taxes and fees booked for 2024 season. Welcome to The Captain's Quarters! This newly built Luxury Rental Home on Longboat Key has everything for you and your family to enjoy your home away from home! This three-story 3-bedroom, 3.5-bath home boasts top of the line features, Smart Home technology, and beautiful decor

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  6925 Longboat Dr S, Longboat Key, FL 34228
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  /2

  $3,170,000 Sold Aug 08, 2025

  689 Lands End Dr, Longboat Key, FL 34228

  • 4 Beds
  • 4.5 Baths
  • 3,254 Sq Ft
  • Built 2005

  Last Sold Summary

  • 17% Below List Price
  • $974/SF
  • 140 Days On Market

  Current Estimated Value $3,111,740

  Last Listing Agent Matthew Voss PREFERRED SHORE LLC

  689 Lands End Dr, Longboat Key, FL 34228
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  /31

  Est $746,249 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 955 Sq Ft

  4401 Gulf of Mexico Dr Unit 803, Longboat Key, FL 34228

  4401 Gulf of Mexico Dr Unit 803, Longboat Key, FL 34228
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  /13

  $300,000

  2800 Harbourside Dr Unit E-03, Longboat Key, FL 34228

  This slip is located in a world class deep harbor marina off Sarasota Bay on Longboat Key. Slip does not require a membership to the Longboat Key Club, however still includes the following amenities of a full service fuel dock, marina pump out boat that comes to your boat, shuttle service to St. Armand's Circle, 24 hour bathhouse with showers with towel service, laundry facilities and a marina

  Heather Claridge RIVER HILLS PROPERTIES, LLC B

  2800 Harbourside Dr Unit E-03, Longboat Key, FL 34228
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  /41

  $6,000 per month

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

  1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228

  Available 07/01/2025 THROUGH 12/30/2025 RENTED SEASON JAN, 2026 THROUGH APRIL, 2026(POSSIBLE ANNUAL)Privateer North PH located Behind the Gates of Longboat Key. GULF VIEWS FROM EVERY ROOM. A top of the line remodel with 2 spacious bedrooms with walk-in closets. The master bedroom ensuite has a king size bed and guest bedroom is a queen size. 2 updated bathrooms with walk-in closets and views of

  Marni Hayden CHROME REALTY LLC

  1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228
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  /2

  $1,575,000 Sold Jun 11, 2025

  1906 Harbour Links Cir Unit 14, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,180 Sq Ft
  • Built 2002

  Last Sold Summary

  • 7% Below List Price
  • $722/SF
  • 124 Days On Market

  Current Estimated Value $1,474,296

  Last Listing Agent Charles Totonis PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1906 Harbour Links Cir Unit 14, Longboat Key, FL 34228
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  /35

  Est $1,005,679 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft

  1085 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  1085 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
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  /10

  $7,775,000

  • Land
  • 0.92 Acre
  • $8,451,087 per Acre

  6351 Gulf of Mexico Dr, Longboat Key, FL 34228

  Sign on Property. Nestled on the pristine shores of Longboat Key, this exclusive beachfront property offers a rare opportunity to build your dream luxury home amidst the breathtaking beauty of the Gulf of Mexico. With direct access to the sugary sands and azure waters, this parcel of land (40,000 sq. ft. / 0.92 acres) promises an unparalleled coastal living experience. Spanning an expansive

  Toni Everett THE TONI EVERETT COMPANY

  6351 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /72

  $10,000 per month

  • 2 Beds
  • 2 Baths
  • 1,839 Sq Ft
  • Condo for Rent

  1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228

  LOCATION, LOCATION, LOCATION!!!!! Gorgeous beach front condo in the sought after Longboat Key community of the Players Club. This light and bright turnkey furnished condo has two bedrooms, two bathrooms, living room/dining room combination, sitting area off the living room, separate sitting room at the front entrance, three lanais with ocean views and a laundry closet with full sized washer and

  C. Alison Hunter JENNETTE PROPERTIES INC

  1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228
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  $1,600,000 Sold Dec 29, 2024

  Unlisted Address

  • Land
  • 0.36 Acre
  • $4,444,444 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 0 Days On Market

  Current Estimated Value $1,298,459

  Last Listing Agent Reid Murphy DEVELOPERS REALTY LBK, INC

  Unlisted Address
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  /45

  Est $1,035,840 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,153 Sq Ft

  3115 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

  3115 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
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  /49

  $689,500

  • 2 Beds
  • 2 Baths
  • 1,371 Sq Ft

  3070 Grand Bay Blvd Unit 612, Longboat Key, FL 34228

  This desirable first-floor corner residence at Grand Bay showcases an expansive wraparound terrace overlooking Sarasota Bay—perfect for enjoying stunning sunrises over the Bay and sunsets over the gardens and golf course. Uniquely positioned for privacy, this home has been tastefully refreshed with a neutral color palette and comes fully furnished, and is the lowest-priced unit in Grand Bay. The

  Andree Huffine COLDWELL BANKER REALTY

  3070 Grand Bay Blvd Unit 612, Longboat Key, FL 34228
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  /30

  $11,769 per month

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • Condo for Rent

  2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228

  ..."' short stories. ....on the island of longboat key You are on the beach included is swimming pool...and a world class tennis courtf...looking play with others and league Town of Longboat Key tennis three blocks away...fitness gym.. . This is direct Gulf front unit with interior hallways from the balcony ,the kitchen,the living room couch...Your on the water.. Breathtaking view of the

  Gerald Cunningham KELLER WILLIAMS ON THE WATER S

  2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228
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  $4,150,000 Sold Feb 03, 2025

  455 Longboat Club Rd Unit 504, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 3,685 Sq Ft
  • Built 1990

  Last Sold Summary

  • 1% Below List Price
  • $1,126/SF
  • 0 Days On Market

  Current Estimated Value $3,778,452

  Last Listing Agent Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  455 Longboat Club Rd Unit 504, Longboat Key, FL 34228
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  /41

  Est $412,630 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,007 Sq Ft

  3802 Gulf of Mexico Dr Unit A203, Longboat Key, FL 34228

  3802 Gulf of Mexico Dr Unit A203, Longboat Key, FL 34228
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  /13

  $300,000

  • Land
  • 1 Acre
  • $300,000 per Acre

  2600 Harbourside Dr Unit H-05, Longboat Key, FL 34228

  The most convenient dock in the Marina! This 55 x 20 foot slip at Longboat Key Club Moorings is located at the Marina Village along the seawall! Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit H-05, Longboat Key, FL 34228
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  /23

  $9,587 per month

  • 3 Beds
  • 2.5 Baths
  • 1,336 Sq Ft
  • Condo for Rent

  4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228

  THIS WONDERFUL PROPERTY IS FOR RENT...NOT FOR SALE...short stories inc...be careful of 3rd party web sites. Stunning direct Gulf front 3 bedroom condo on the quaint island of Longboat Key on Florida's tranquil Gulf Coast. Sunny days and uncompromising beauty awaits you. Experience the island lifestyle of relaxation and escape. Warm ocean breezes flow through the unit and the peaceful sound of

  Gerald Cunningham KELLER WILLIAMS ON THE WATER S

  4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
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  /2

  $1,538,000 Sold Oct 08, 2025

  2675 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,180 Sq Ft
  • Built 1979

  Last Sold Summary

  • 8% Below List Price
  • $706/SF
  • 46 Days On Market

  Last Listing Agent Sandra Endres COLDWELL BANKER REALTY

  2675 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228
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  /50

  Est $2,650,276 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,054 Sq Ft

  1281 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

  1281 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

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