Longboat Key, FL Homes

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  /64

  $9,700,000

  • 4 Beds
  • 5 Baths
  • 5,245 Sq Ft

  560 Harbor Point Rd, Longboat Key, FL 34228

  Exquisite Palladian-Style Waterfront Estate Located on the serene shores of Sarasota Bay, this home epitomizes elegance and sophistication. Designed by Cliff Scholz and meticulously crafted by Murray Homes, this, 5,300-square-foot masterpiece is situated in a double-gated community offering unparalleled privacy and exclusivity. Perched at the end of a quiet cul-de-sac, the property boasts almost

  Jonathan Fox MICHAEL SAUNDERS & COMPANY

  560 Harbor Point Rd, Longboat Key, FL 34228
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  /44

  $12,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • Seaside Serenity: Luxurious Gulf-Front Retreat on Southern Longboat Key

  2425 Gulf of Mexico Dr, 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, two-bath

  2425 Gulf of Mexico Dr, Longboat Key, FL 34228
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  $475,000 Sold Mar 31, 2026

  6750 Gulf of Mexico Dr Unit 154, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,441 Sq Ft
  • Built 1970

  Last Sold Summary

  • 17% Below List Price
  • $330/SF
  • 66 Days On Market

  Current Estimated Value $539,217

  Last Listing Agent Amy Jones COASTAL KEY REALTY LLC

  6750 Gulf of Mexico Dr Unit 154, Longboat Key, FL 34228
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  /88

  Est $631,763 Not Listed For Sale

  5260 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 1,453 Sq Ft
  • Built 1974

  5260 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228

  Last Sold Summary

  • 8% Below List Price
  • $475/SF
  • 49 Days On Market

  • Last Sold Price $690,000
  • Aug 01, 2023

  Last Listing Agent Judy Kepecz-Hays COLDWELL BANKER REALTY
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  /64

  $622,000

  • 1 Bed
  • 1.5 Baths
  • 1,094 Sq Ft

  2055 Gulf of Mexico Dr Unit G2213, Longboat Key, FL 34228

  NO expense spared and everything replaced! Gulf and greenbelt views await from your top floor Seaplace condo! Completely remodeled. This gorgeous gulf-facing oversized one bedroom, 1.5 bath end unit with vaulted ceilings features 1,094 square feet of living space and spacious lanai adding an additional 112 square feet with custom 95% UV blocking solar shades. The convenient second floor location

  Derek Eisenberg CONTINENTAL REAL ESTATE GROUP

  2055 Gulf of Mexico Dr Unit G2213, Longboat Key, FL 34228
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  /40

  $5,500 Per Month

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

  4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228

  Longboat Key vacation rental, rarely available Tiffany Plaza direct Gulf Front condo with amazing views! As you enter your gaze will be drawn to the turquoise waters of the Gulf of Mexico and the serene beach frontage. This lovely home offers 2 beds & 2 baths, plus a bonus office space with a twin Murphy bed! The kitchen and the baths have been updated, the primary bedroom offers a King bed, walk

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
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  $337,500 Sold Mar 26, 2026

  730 Spanish Dr S Unit 99, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,375 Sq Ft
  • Built 1969

  Last Sold Summary

  • 16% Below List Price
  • $245/SF
  • 284 Days On Market

  Current Estimated Value $355,310

  Last Listing Agent Adrienne Scott MICHAEL SAUNDERS & COMPANY

  730 Spanish Dr S Unit 99, Longboat Key, FL 34228
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  /24

  Est $989,928 Not Listed For Sale

  628 Lyons Ln, Longboat Key, FL 34228

  628 Lyons Ln, Longboat Key, FL 34228

  Last Sold Summary

  • 19% Below List Price
  • 101 Days On Market

  • Last Sold Price $1,225,000
  • Sep 28, 2023

  Last Listing Agent JoDene Moneuse Michael Saunders
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  $739,000

  • 2 Beds
  • 2 Baths
  • 1,601 Sq Ft

  706 Bayport Way Unit 706, Longboat Key, FL 34228

  This stylish turnkey furnished beach retreat at Bayport Beach & Tennis Club is the perfect blend of classy with a modern flair. Before entering the home take note of the huge 16’ x 13’ outdoor deck where you can enjoy a partial view of the Gulf. It's a great place to start your day with a cup of morning coffee, or enjoy a nice meal in the evening, and catch the spectacular colors of the sky as

  Kelly Erb COLDWELL BANKER REALTY

  706 Bayport Way Unit 706, Longboat Key, FL 34228
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  /31

  $17,000 Per Month

  • 1 Bed
  • 2 Baths
  • 1,556 Sq Ft
  • Unfurnished Luxury Rental at The St. Regis Longboat Key

  1591 Gulf of Mexico Dr, Longboat Key, FL 34228

  Long Term Unfurnished Rental. Experience elevated coastal living in this exceptional unfurnished annual residence at The St. Regis Longboat Key Resort. Accessed via a private elevator, this sophisticated home opens into a dramatic living space defined by soaring ceilings and walls of glass that frame breathtaking views of Sarasota Bay. The expansive living area flows seamlessly to a generous

  1591 Gulf of Mexico Dr, Longboat Key, FL 34228
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  $500,000 Sold May 01, 2026

  620 Companion Way, Longboat Key, FL 34228

  • Land
  • 8,276 Sq Ft
  • $2,631,579 per Acre

  Last Sold Summary

  • 15% Below List Price
  • 68 Days On Market

  Current Estimated Value $575,612

  Last Listing Agent JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  620 Companion Way, Longboat Key, FL 34228
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  /17

  Est $191,496 Not Listed For Sale

  2600 Harbourside Dr Unit G-2, Longboat Key, FL 34228

  • Studio
  • 800 Sq Ft
  • Built 1983

  2600 Harbourside Dr Unit G-2, Longboat Key, FL 34228

  Last Sold Summary

  • 15% Below List Price
  • $281/SF
  • 391 Days On Market

  • Last Sold Price $225,000
  • May 23, 2024

  Last Listing Agent Jennifer Wilson LBRE LLC
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  /79

  $3,775,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 4,281 Sq Ft

  550 Yardarm Ln, Longboat Key, FL 34228

  Under contract-accepting backup offers. Motivated seller ....ELEVATED Waterfront Luxury on Longboat Key! Welcome to 550 Yardarm Lane, where the elegance of Longboat Key meets the ease of Florida’s coastal lifestyle in the coveted Country Club Shores. This waterfront masterpiece isn’t just a home, it’s your front-row seat to paradise, where boating, beach walks, and year-round sunshine are part of

  Melanie Russell QUEST PROPERTIES INC

  550 Yardarm Ln, Longboat Key, FL 34228
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  /44

  $14,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • 3,268 Sq Ft
  • House for Rent

  531 Birdie Ln, Longboat Key, FL 34228

  Annual Rental – Stunning Waterfront Home in Country Club Shores on Longboat Key. Experience the best of waterfront living in this beautiful 4-bedroom, 3.5-bathroom home located in the sought-after Country Club Shores community on Longboat Key. This spacious and elegant residence offers breathtaking canal views, luxurious amenities, and direct boating access and boat lift. This exceptional home

  Karie Gorgone WAGNER REALTY

  531 Birdie Ln, Longboat Key, FL 34228
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  $470,000 Sold Jan 16, 2026

  3155 Gulf of Mexico Dr Unit 257, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 416 Sq Ft
  • Built 1960

  Last Sold Summary

  • $1,130/SF
  • 9 Days On Market

  Current Estimated Value $471,457

  Last Listing Agent Ryndie Brusco MICHAEL SAUNDERS & COMPANY

  3155 Gulf of Mexico Dr Unit 257, Longboat Key, FL 34228
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  /2

  Est $1,107,162 Not Listed For Sale

  1125 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Built 1979

  1125 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

  Last Sold Summary

  • $797/SF
  • 94 Days On Market

  • Last Sold Price $1,110,000
  • Oct 08, 2024

  Last Listing Agent Maggie Hicks COLDWELL BANKER REALTY
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  $2,790,000

  • 3 Beds
  • 3 Baths
  • 4,182 Sq Ft

  677 Lands End Dr, Longboat Key, FL 34228

  In a rich tropical waterfront setting on Longboat Key, this unique retreat lives like a modern treehouse while evoking a sense of peace, family and comfortable, easy island living. Tucked within the island’s native landscape along a natural bayou off Sarasota Bay, the property offers a rare opportunity to experience serene waterfront living surrounded by nature, with the Gulf’s azure waters and

  Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  677 Lands End Dr, Longboat Key, FL 34228
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  /26

  $3,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Condo for Rent

  4330 Falmouth Dr, Longboat Key, FL 34228

  Longboat Key Beach and Bay Access.2 Bedroom 2 Bathroom First Floor condo in a gated community with tons of amenities.✅ Deepwater channel with docks and slips available up to 34' (on waitlist)✅ Amazing water views & breezes✅ Private deeded beach access (private building on beach with showers + bathrooms, benches and tables!)✅ 4 Pools, clubhouse, gym, sauna,

  4330 Falmouth Dr, Longboat Key, FL 34228
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  $1,030,000 Sold Oct 31, 2025

  3111 Bayou Sound, Longboat Key, FL 34228

  • 3 Beds
  • 5 Baths
  • 2,908 Sq Ft
  • Built 1984

  Last Sold Summary

  • 30% Below List Price
  • $354/SF
  • 203 Days On Market

  Current Estimated Value $1,147,566

  Last Listing Agent Judy Mitchell PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3111 Bayou Sound, Longboat Key, FL 34228
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  /2

  Est $3,080,772 Not Listed For Sale

  1281 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,667 Sq Ft
  • Built 1999

  1281 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228

  Last Sold Summary

  • 23% Below List Price
  • $1,500/SF
  • 230 Days On Market

  • Last Sold Price $4,000,000
  • Oct 25, 2024

  Last Listing Agent Laura Rode KW COASTAL LIVING III
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  /39

  $1,700,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft

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

  Under contract-accepting backup offers. Amazing and Unobstructed 14th Floor Gulf and Beach Views! This is the perfectly remodeled unit you've been waiting for, with stunning sky views! Open floor plan, tile floors throughout, gorgeous open kitchen, and split bedroom floor plan. Just move right in and enjoy the views and amenities. The building has been completely remodeled. New roof, new windows,

  Robert Delaney MICHAEL SAUNDERS & COMPANY

  2425 Gulf of Mexico Dr Unit 14E, Longboat Key, FL 34228
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  /65

  $78,000 Per Month

  • 4 Beds
  • 4.5 Baths
  • 5,334 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228

  There are moments in life that stop you mid-thought. Moments so immersive that words struggle to keep up with what you’re feeling. This penthouse is one of those moments. Offered to the public for the first time, this four-bedroom residence sits high above the Gulf of Mexico, where light, water, and horizon become part of everyday life. A private elevator opens directly into the home, setting the

  Inbal August DOUGLAS ELLIMAN

  1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228
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  $1,425,000 Sold Nov 26, 2025

  603 Longboat Club Rd Unit 1103N, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft
  • Built 1970

  Last Sold Summary

  • 7% Below List Price
  • $977/SF
  • 11 Days On Market

  Current Estimated Value $1,428,951

  Last Listing Agent Irma Scherer COMPASS FLORIDA LLC

  603 Longboat Club Rd Unit 1103N, Longboat Key, FL 34228
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  Est $2,080,345 Not Listed For Sale

  6957 Longboat Dr S, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,499 Sq Ft
  • Built 2019

  6957 Longboat Dr S, Longboat Key, FL 34228

  Last Sold Summary

  • 19% Below List Price
  • $1,030/SF
  • 11 Days On Market

  • Last Sold Price $2,575,000
  • Dec 18, 2023

  Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY
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  $1,395,000

  • 2 Beds
  • 2.5 Baths
  • 1,569 Sq Ft

  1485 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

  Coastal elegance meets effortless island living at The Player’s Club on Longboat Key. This 2-bedroom, 2.5-bath Gulf-front residence located in building #1 offers direct Gulf views from the private balcony, where nightly sunsets paint the sky in unforgettable color, your front-row seat to paradise. Located in a guard-gated, low-density community with 560 feet of private beachfront, this property

  Rinat Sikdar COLDWELL BANKER REALTY

  1485 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
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  /27

  $5,200 Per Month

  • 2 Beds
  • 2 Baths
  • 1,370 Sq Ft
  • Amazing 2BR Condo in Longboat Key

  807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228

  Welcome to your dream condo in beautiful Longboat Key! This spacious 2-bedroom, 2-bathroom gem offers 1,370 square feet of modern living, perfect for those who appreciate both comfort and style. With a host of amenities and a vibrant community atmosphere, this property is sure to impress.Step inside to find a well-appointed kitchen featuring:- Electric range and stove top-

  807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228
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  $1,675,000 Sold Mar 27, 2026

  3519 Fair Oaks Ln, Longboat Key, FL 34228

  • 5 Beds
  • 3.5 Baths
  • 3,924 Sq Ft
  • Built 1998

  Last Sold Summary

  • 1% Below List Price
  • $427/SF
  • 5 Days On Market

  Current Estimated Value $1,770,533

  Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY

  3519 Fair Oaks Ln, Longboat Key, FL 34228
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  /19

  Est $170,872 Not Listed For Sale

  2600 Harbourside Dr Unit H-06, Longboat Key, FL 34228

  • Studio
  • 1,200 Sq Ft
  • Built 1987

  2600 Harbourside Dr Unit H-06, Longboat Key, FL 34228

  Last Sold Summary

  • 15% Below List Price
  • $167/SF
  • 281 Days On Market

  • Last Sold Price $200,000
  • Nov 16, 2023

  Last Listing Agent Jennifer Wilson LBRE LLC
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  /55

  $929,000

  • 3 Beds
  • 2 Baths
  • 2,105 Sq Ft

  2110 Harbourside Dr Unit 547, Longboat Key, FL 34228

  Experience refined coastal living behind the gates of the prestigious Bay Isles. This beautifully appointed 3-bedroom, 2-bath residence in The Atrium offers an exceptional blend of elegance, comfort, and convenience just minutes from St. Armands Circle and vibrant downtown Sarasota. Designed for effortless living and entertaining, the open floor plan showcases high ceilings, a sophisticated blend

  Mimi Kruk MICHAEL SAUNDERS & COMPANY

  2110 Harbourside Dr Unit 547, Longboat Key, FL 34228
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  /39

  $10,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,576 Sq Ft
  • Condo for Rent

  4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228

  **BEST WATER VIEWS - Enjoy a warm Winter Escape at this expansive 3 bed 2 bath LONGBOAT KEY PENTHOUSE BEACHFRONT CONDO!** **AVAILABLE to lease DECEMBER 2026 and APRIL 2027** Welcome to your dream winter retreat, where you can bask in the beauty of the Gulf of Mexico right from your living room. This pristine, 2-bedrooms +Den/Office with Sleeper Sofa and 2-bath penthouse condo is located directly

  Norma Mladineo COLDWELL BANKER REALTY

  4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
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  $1,850,000 Sold Oct 03, 2025

  540 Gulf Bay Rd, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 1,880 Sq Ft
  • Built 1993

  Last Sold Summary

  • 5% Below List Price
  • $984/SF
  • 124 Days On Market

  Current Estimated Value $1,781,983

  Last Listing Agent Brett Coady PINEYWOODS REALTY LLC

  540 Gulf Bay Rd, Longboat Key, FL 34228
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  /66

  Est $3,393,772 Not Listed For Sale

  3521 Bayou Pointe, Longboat Key, FL 34228

  • 3 Beds
  • 4.5 Baths
  • 3,687 Sq Ft
  • Built 1996

  3521 Bayou Pointe, Longboat Key, FL 34228

  Last Sold Summary

  • 12% Below List Price
  • $1,044/SF
  • 35 Days On Market

  • Last Sold Price $3,850,000
  • Mar 08, 2024

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY
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  $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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  /77

  $6,950 Per Month

  • 2 Beds
  • 2 Baths
  • 2,369 Sq Ft
  • Luxury Furnished Longboat Key Retreat with Private Beach Club Access & Golf Course Views Remodele...

  2013 Harbour Links Dr, Longboat Key, FL 34228

  Step into elevated coastal living at 2013 Harbour Links Drive, a recently remodeled and beautifully curated 2-bedroom, 2-bathroom residence offering 2,369 square feet of beautifully designed living space on Longboat Key. Offered fully furnished and ready for immediate enjoyment, this home is perfectly positioned on a quiet cul-de-sac with extra guest parking, combining privacy, luxury, and

  2013 Harbour Links Dr, Longboat Key, FL 34228
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  $340,000 Sold Nov 25, 2025

  4360 Chatham Dr Unit 204, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 747 Sq Ft
  • Built 1969

  Last Sold Summary

  • $455/SF
  • 0 Days On Market

  Current Estimated Value $342,064

  Last Listing Agent Mairead Smialek COLDWELL BANKER REALTY

  4360 Chatham Dr Unit 204, Longboat Key, FL 34228
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  Est $1,570,985 Not Listed For Sale

  2425 Gulf of Mexico Dr Unit 13A, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,513 Sq Ft
  • Built 1973

  2425 Gulf of Mexico Dr Unit 13A, Longboat Key, FL 34228

  Last Sold Summary

  • 2% Below List Price
  • $1,058/SF
  • 79 Days On Market

  • Last Sold Price $1,600,000
  • Sep 15, 2023

  Last Listing Agent Courtney Green PREMIER SOTHEBYS INTL REALTY
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  /72

  $1,750,000

  • 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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  $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
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  /2

  $1,190,000 Sold Sep 05, 2025

  1445 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

  • 2 Beds
  • 2.5 Baths
  • 1,721 Sq Ft
  • Built 1982

  Last Sold Summary

  • 5% Below List Price
  • $691/SF
  • 51 Days On Market

  Current Estimated Value $1,177,449

  Last Listing Agent Mairead Smialek COLDWELL BANKER REALTY

  1445 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
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  /50

  Est $1,538,785 Not Listed For Sale

  2425 Gulf of Mexico Dr Unit 11E, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • Built 1973

  2425 Gulf of Mexico Dr Unit 11E, Longboat Key, FL 34228

  Last Sold Summary

  • 6% Below List Price
  • $1,112/SF
  • 0 Days On Market

  • Last Sold Price $1,635,000
  • Apr 28, 2023

  Last Listing Agent Robert Delaney Michael Saunders

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