Longboat Key, FL Homes

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  $650,000

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  909 Spanish Dr N Unit 51, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. This gorgeous two-bedroom, two-bath Spanish Main standalone villa is a must-see! The fully complete custom remodel has been beautifully and tastefully appointed with meticulous craftsmanship. So many upgrades. Starting with the neutral tile plank flooring that runs throughout the villa, providing a seamless flow from room to room. The kitchen is a

  Kimberly Freiwald PREMIER SOTHEBY'S INTERNATIONAL REALTY

  909 Spanish Dr N Unit 51, Longboat Key, FL 34228
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  $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 2027! 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
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  $625,000 Sold Aug 07, 2025

  321 N Shore Rd Unit LOT ONLY, Longboat Key, FL 34228

  • Land
  • 6,098 Sq Ft
  • $4,464,286 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 185 Days On Market

  Current Estimated Value $617,727

  Last Listing Agent Brian Leakeas COLDWELL BANKER REALTY

  321 N Shore Rd Unit LOT ONLY, Longboat Key, FL 34228
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  /53

  Est $722,581 Not Listed For Sale

  225 Sands Point Rd Unit 6106, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 642 Sq Ft
  • Built 1983

  225 Sands Point Rd Unit 6106, Longboat Key, FL 34228

  Last Sold Summary

  • 15% Below List Price
  • $1,322/SF
  • 34 Days On Market

  • Last Sold Price $849,000
  • May 02, 2024

  Last Listing Agent Ian Addy, PA Michael Saunders
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  /43

  $550,000

  • 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 (elevator access on the north end) 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, crown molding, no popcorn ceilings, no carpet, new hurricane

  Diane Fogo Harter MICHAEL SAUNDERS & COMPANY

  2039 Gulf of Mexico Dr Unit G3207, Longboat Key, FL 34228
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  /31

  $10,000 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,957 Sq Ft
  • Condo for Rent

  1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  Luxury Living meets Modern Coastal at Gulf Front Haven, a beautifully updated, modern, ocean view floorplan that sits right on the beach at Longboat Key, one of the Gulf Coasts Premier Living Areas! This home is located right in the heart of the Players Club, one of Longboat Keys most luxurious communities with all the amenities to make your stay great!! The condo is located on the 3rd Floor with

  Brad Wilson M&M PROPERTY MANAGEMENT GROUP

  1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
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  $2,285,000 Sold Mar 31, 2026

  617 Neptune Ave, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,939 Sq Ft
  • Built 2019

  Last Sold Summary

  • 5% Below List Price
  • $777/SF
  • 7 Days On Market

  Current Estimated Value $2,354,405

  Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY

  617 Neptune Ave, Longboat Key, FL 34228
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  /31

  Not Listed For Sale

  3710 Gulf of Mexico Dr Unit C24, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 621 Sq Ft
  • Built 1961

  3710 Gulf of Mexico Dr Unit C24, Longboat Key, FL 34228

  Last Sold Summary

  • $403/SF
  • 28 Days On Market

  • Last Sold Price $250,000
  • Jun 01, 2023

  Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC
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  $2,399,000

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

  455 Longboat Club Rd Unit 408, Longboat Key, FL 34228

  Behind the gates of the renowned Longboat Key Club, this stunning residence at The Pierre offers a rare opportunity to enjoy elevated coastal living paired with the ease and sophistication of a true resort lifestyle. Completely renovated by Brista Homes, this 3-bedroom, 3.5-bath condominium is spacious, refined, and thoughtfully curated, with three oversized bedrooms each featuring a private

  Gina Ursini BRISTA REALTY LLC

  455 Longboat Club Rd Unit 408, Longboat Key, FL 34228
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  $7,200 Per Month

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • Condo for Rent

  4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228

  This magnificent Gulf front vacation retreat sits on the 6th floor of the beautiful Westchester of Longboat Key, boasting expansive full Gulf views. This is a stunning property situated on a 7-acre stretch of white, powdery beaches and meticulously manicured landscape. The amenities can’t be beat and include 2 heated pools, tennis court, Clubhouse, shuffleboard, private Tiki-huts, & covered

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228
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  $580,000 Sold Jun 25, 2025

  681 Fox St, Longboat Key, FL 34228

  • 2 Beds
  • 1 Bath
  • 810 Sq Ft
  • Built 1964

  Last Sold Summary

  • 1% Above List Price
  • $716/SF
  • 4 Days On Market

  Current Estimated Value $589,036

  Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  681 Fox St, Longboat Key, FL 34228
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  /57

  Est $428,609 Not Listed For Sale

  4770 Gulf of Mexico Dr Unit Villa 6, Longboat Key, FL 34228

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1974

  4770 Gulf of Mexico Dr Unit Villa 6, Longboat Key, FL 34228

  Last Sold Summary

  • 5% Below List Price
  • $493/SF
  • 0 Days On Market

  • Last Sold Price $450,000
  • Jul 01, 2024

  Last Listing Agent Debby McCaig COLDWELL BANKER REALTY
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  $7,495,000

  • 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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  $12,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,411 Sq Ft
  • Condo for Rent

  4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228

  Longboat Key Gulf Front Vacation Rental! Gorgeous views from every window, 2 beds, 2 baths, fourth floor end unit in the wonderful boutique-style community of Tiffany Plaza. Look no further for your perfect vacation retreat, located directly on the Gulf of Mexico, this lovely condo has all you need. The updated kitchen has a center Island with breakfast bar, farm-style sink, and stainless steel

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228
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  $600,000 Sold Apr 08, 2026

  521 Broadway St, Longboat Key, FL 34228

  • Land
  • 1 Acre
  • $600,000 per Acre

  Last Sold Summary

  • 28% Below List Price
  • 0 Days On Market

  Current Estimated Value $677,205

  Last Listing Agent Gerald Cunningham KELLER WILLIAMS ON THE WATER S

  521 Broadway St, Longboat Key, FL 34228
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  Est $505,301 Not Listed For Sale

  3320 Gulf of Mexico Dr Unit 302C, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,187 Sq Ft
  • Built 1971

  3320 Gulf of Mexico Dr Unit 302C, Longboat Key, FL 34228

  Last Sold Summary

  • 6% Above List Price
  • $403/SF
  • 48 Days On Market

  • Last Sold Price $478,000
  • Feb 07, 2025

  Last Listing Agent Karin Leereveld COLDWELL BANKER REALTY
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  $5,985,000

  • Land
  • 12,196 Sq Ft
  • $21,375,000 per Acre

  530 Jessmyth Dr, Longboat Key, FL 34228

  Under construction and designed for the ultimate boating lifestyle, this exceptional 5-bedroom, 7-bath residence is ideally positioned on a deep water canal in the highlydesirable Longboat Key Estates community. Offering over 4,500 square feet of refined,resort-style living, the home is built to latest hurricane building standards with solid block construction and hurricane-impact

  Greg Bayer BEACH HOUSE REAL ESTATE LLC

  530 Jessmyth Dr, Longboat Key, FL 34228
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  /69

  $25,000 Per Month

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

  690 Old Compass Rd, Longboat Key, FL 34228

  Coveted lifestyle and location on one of the widest deep water canals on LONGBOAT KEY with direct access to Sarasota Bay with no bridges! This house has been totally renovated right down to the studs giving you 3,230 square feet of total luxury living. Meticulously maintained, this home has 3 bedrooms. The primary bedroom is en-suite with a king size bed, 2nd and 3rd bedrooms feature queen size

  Teresa Ribaudo JENNETTE PROPERTIES INC

  690 Old Compass Rd, Longboat Key, FL 34228
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  $6,000,000 Sold Oct 03, 2025

  1591 Gulf of Mexico Dr Unit 511, Longboat Key, FL 34228

  • 2 Beds
  • 2.5 Baths
  • 3,130 Sq Ft
  • Built 2024

  Last Sold Summary

  • 14% Below List Price
  • $1,917/SF
  • 99 Days On Market

  Current Estimated Value $6,004,205

  Last Listing Agent Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  1591 Gulf of Mexico Dr Unit 511, Longboat Key, FL 34228
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  Not Listed For Sale

  3710 Gulf of Mexico Dr Unit G-34, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1977

  3710 Gulf of Mexico Dr Unit G-34, Longboat Key, FL 34228

  Last Sold Summary

  • $260/SF
  • 65 Days On Market

  • Last Sold Price $275,000
  • Aug 15, 2024

  Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC
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  /20

  $995,000

  • Land
  • 6,969 Sq Ft
  • $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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  /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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  $3,350,000 Sold Nov 21, 2025

  2333 Gulf of Mexico Dr Unit 1A3, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 3,060 Sq Ft
  • Built 1997

  Last Sold Summary

  • 21% Below List Price
  • $1,095/SF
  • 92 Days On Market

  Current Estimated Value $3,517,450

  Last Listing Agent Steve and Janet Walter MICHAEL SAUNDERS & COMPANY

  2333 Gulf of Mexico Dr Unit 1A3, Longboat Key, FL 34228
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  Not Listed For Sale

  90 Main Street Dr, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 568 Sq Ft
  • Built 1959

  90 Main Street Dr, Longboat Key, FL 34228

  Last Sold Summary

  • $185/SF
  • 21 Days On Market

  • Last Sold Price $105,000
  • Jun 25, 2024

  Last Listing Agent Crystal Cain RE/MAX
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  $1,595,000

  • 3 Beds
  • 3 Baths
  • 3,229 Sq Ft

  721 Binnacle Point Dr, Longboat Key, FL 34228

  PREMIER LOCATION in Emerald Harbor -- HOUSE TO BE DEMOLISHED -- LOT IS GRADED AND READY TO BUILD -- Located on the apex of the WIDEST CANAL on Longboat Key, 721 Binnacle Point Drive is ready for a new owner with a new vision! The property has 96' of canal frontage with BRAND NEW Sea Wall (2024), 120' of street frontage, with just over 18,800 SF upon which to build your dream home. Build new and

  James Frost KINCAID REALTY

  721 Binnacle Point Dr, Longboat Key, FL 34228
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  $15,000 Per Month

  • 2 Beds
  • 2.5 Baths
  • 2,135 Sq Ft
  • Condo for Rent

  1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228

  Gorgeous gulf front vacation rental! Be the first to lease this wonderfully renovated 10th-story penthouse condominium in the Promenade on Longboat Key. This elegant residence offers two bedrooms and two and one half baths in over 2,100 square feet of living space. Fabulous views of the Gulf from every window. No expense was spared during this renovation; you will love the open floor plan with a

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228
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  $629,950 Sold Mar 24, 2026

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

  • 2 Beds
  • 2 Baths
  • 1,371 Sq Ft
  • Built 1995

  Last Sold Summary

  • 9% Below List Price
  • $459/SF
  • 103 Days On Market

  Current Estimated Value $648,910

  Last Listing Agent Andree Huffine COLDWELL BANKER REALTY

  3070 Grand Bay Blvd Unit 612, Longboat Key, FL 34228
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  Est $1,364,039 Not Listed For Sale

  2525 Gulf of Mexico Dr Unit 11B, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,491 Sq Ft
  • Built 1972

  2525 Gulf of Mexico Dr Unit 11B, Longboat Key, FL 34228

  Last Sold Summary

  • 9% Above List Price
  • $838/SF
  • 96 Days On Market

  • Last Sold Price $1,250,000
  • Aug 29, 2024

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY
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  $2,995,000

  • 3 Beds
  • 3.5 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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  /26

  $5,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  640 Broadway St, Longboat Key, FL 34228

  HOT off-season specials from June 15th through end of August. Step into living history in the heart of Historic Longbeach Village. This exceptional property occupies land that was part of Civil War veteran Thomas Mann’s 144-acre homestead, where in 1891 he built the island’s first permanent residence just steps away. This serene corner lot is where Longboat Key truly began! Fully rebuilt and

  Christina Vescovo LPT REALTY, LLC

  640 Broadway St, Longboat Key, FL 34228
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  $1,251,000 Sold Apr 28, 2026

  2450 Harbourside Dr Unit 212, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 2,830 Sq Ft
  • Built 1990

  Last Sold Summary

  • $442/SF
  • 6 Days On Market

  Current Estimated Value $1,637,084

  Last Listing Agent Beth Lancaster-Collins CORCORAN DWELLINGS REALTY

  2450 Harbourside Dr Unit 212, Longboat Key, FL 34228
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  Est $1,412,266 Not Listed For Sale

  1055 Gulf of Mexico Dr Unit 601, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft
  • Built 1981

  1055 Gulf of Mexico Dr Unit 601, Longboat Key, FL 34228

  Last Sold Summary

  • 14% Below List Price
  • $1,408/SF
  • 20 Days On Market

  • Last Sold Price $1,650,000
  • Jun 14, 2024

  Last Listing Agent Maggie Hicks COLDWELL BANKER REALTY
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  $709,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,561 Sq Ft

  5757 Gulf of Mexico Dr Unit 115, Longboat Key, FL 34228

  Under contract-accepting backup offers. Lush garden views and a peek at the Gulf are enjoyed from this 2 bedroom 1st floor walkout residence at The Shore. Owners will appreciate the well positioned primary suite with separate access to the terrace, a walk-in closet and gulf water views. The spacious kitchen offers abundant counter space, an exterior door and a desk area that could also be used as

  Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  5757 Gulf of Mexico Dr Unit 115, Longboat Key, FL 34228
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  $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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  $739,000 Sold Jun 18, 2025

  1945 Gulf of Mexico Dr Unit M2313, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,265 Sq Ft
  • Built 1978

  Last Sold Summary

  • $584/SF
  • 1 Day On Market

  Current Estimated Value $755,522

  Last Listing Agent Bruce Meyer MICHAEL SAUNDERS & COMPANY

  1945 Gulf of Mexico Dr Unit M2313, Longboat Key, FL 34228
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  Est $1,244,916 Not Listed For Sale

  1965 Gulf of Mexico Dr Unit G5-201 & 203, Longboat Key, FL 34228

  • 4 Beds
  • 3 Baths
  • 2,425 Sq Ft
  • Built 1977

  1965 Gulf of Mexico Dr Unit G5-201 & 203, Longboat Key, FL 34228

  Last Sold Summary

  • $515/SF
  • 186 Days On Market

  • Last Sold Price $1,250,000
  • Nov 01, 2024

  Last Listing Agent Oliver Giesser EXP REALTY LLC
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  $5,999,000

  • 4 Beds
  • 4.5 Baths
  • 3,921 Sq Ft

  2251 Gulf of Mexico Dr Unit 301, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. Welcome to an exceptional Gulf-front residence within the prestigious Aria community on the coveted south end of Longboat Key where refined coastal living meets timeless elegance. Set along 300 feet of pristine private shoreline, this extraordinary property offers a rare opportunity to experience true beachfront luxury in one of Sarasota’s most

  Rachel Woodruff HOUSE MATCH

  2251 Gulf of Mexico Dr Unit 301, Longboat Key, FL 34228
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  $10,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,463 Sq Ft
  • Condo for Rent

  2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228

  Booked Dec 1st 2026-March 31st 2027. Welcome to your amazing beachfront Longboat Key at Sunset Beach vacation. Sunset Beach is a 3 building complex located directly on Gulf of Mexico and it's powdery sandy beach and perfect sunset views. Guests will find a large gulf front pool, spa, community room for social gatherings, fire pit and BBQ grill. You are welcome to beach chairs along the private

  Jennifer Le Blanc PRECISE REALTY CORP

  2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228
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  $815,000 Sold Feb 12, 2026

  1904 Harbourside Dr Unit 201, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,135 Sq Ft
  • Built 1982

  Last Sold Summary

  • 9% Below List Price
  • $382/SF
  • 24 Days On Market

  Current Estimated Value $824,654

  Last Listing Agent Monica LeSuer DOUGLAS ELLIMAN

  1904 Harbourside Dr Unit 201, Longboat Key, FL 34228
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  Not Listed For Sale

  3710 Gulf of Mexico Dr Unit B3, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 680 Sq Ft
  • Built 1974

  3710 Gulf of Mexico Dr Unit B3, Longboat Key, FL 34228

  Last Sold Summary

  • $441/SF
  • 26 Days On Market

  • Last Sold Price $300,000
  • Jun 07, 2024

  Last Listing Agent Patrick Brogley KELLER WILLIAMS ON THE WATER S

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