Longboat Key, FL Homes

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  /94

  $549,900

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft

  4380 Exeter Dr Unit 204, Longboat Key, FL 34228

  Make your dreams come true with this beautiful waterfront condominium located at the popular Longboat Harbour resort! Enjoy gorgeous views of the water the moment you step in. This newly renovated 2BD/2BA second floor unit offers a roomy open floor plan with plenty of natural light, is being sold turnkey furnished. New Luxury Vinyl flooring and hurricane windows has been installed throughout. The

  Sandi Layfield MICHAEL SAUNDERS & COMPANY

  4380 Exeter Dr Unit 204, Longboat Key, FL 34228
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  /23

  $5,000 per month

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

  1922 Harbourside Dr Unit 1102, 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

  Victoria Campbell LPT REALTY LLC

  1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228
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  /2

  $530,000 Sold Apr 28, 2025

  709 Bayport Way Unit 709, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1980

  Last Sold Summary

  • 27% Below List Price
  • $379/SF
  • 334 Days On Market

  Current Estimated Value $528,470

  Last Listing Agent Roger Clyne PREFERRED SHORE LLC

  709 Bayport Way Unit 709, Longboat Key, FL 34228
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  /2

  Est $1,341,816 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

  • 7% Above List Price
  • $838/SF
  • 96 Days On Market

  Last Sold Price $1,250,000

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY
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  /18

  $380,000

  2600 Harbourside Dr Unit J-09, Longboat Key, FL 34228

  Unique location on the lawn at Longboat Key Club Moorings! A 70 x 21 slip that is conveniently located near the Marina Village. One of the boaters favorite location. Club membership is 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

  Jennifer Wilson LBRE LLC

  2600 Harbourside Dr Unit J-09, 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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  /2

  $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 $738,529

  Last Listing Agent Bruce Meyer MICHAEL SAUNDERS & COMPANY

  1945 Gulf of Mexico Dr Unit M2313, Longboat Key, FL 34228
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  /45

  Est $1,424,815 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

  Last Listing Agent Maggie Hicks COLDWELL BANKER REALTY
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  /58

  $774,900

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

  4805 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228

  NEW Best Price Opportunity Beach Front! Thoughtfully Updated with high- quality finishes! Experience refined Gulf-front living in this first-floor, Gulf-view residence with direct walk-out access to a private sandy beach. This pristine 2-bedroom, 2-bath home showcases an updated kitchen and spa-inspired baths, impact-resistant sliding doors that open seamlessly to two screened lanais, and a

  Malihe Karimi MICHAEL SAUNDERS & COMPANY

  4805 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228
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  /47

  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft
  • Condo for Rent

  4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  Furnished beachfront vacation rental! This spacious (1336 sq ft + balcony) condo is a luxurious living space that offers breathtaking panoramic views of the beach, sunset, and Gulf of Mexico. It is located in a smaller building, on an uncrowded segment of beach that can often be enjoyed in complete solitude. The unit was recently upgraded with a new washer/dryer, luxury vinyl flooring in the

  Daniel Goldman COMPASS FLORIDA LLC

  4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
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  /2

  $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 $898,470

  Last Listing Agent Monica LeSuer DOUGLAS ELLIMAN

  1904 Harbourside Dr Unit 201, Longboat Key, FL 34228
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  /2

  Est $1,366,577 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

  • 9% Above List Price
  • $515/SF
  • 186 Days On Market

  Last Sold Price $1,250,000

  Last Listing Agent Oliver Giesser EXP REALTY LLC
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  /90

  $1,695,000

  • 3 Beds
  • 2 Baths
  • 2,317 Sq Ft

  690 Jungle Queen Way, Longboat Key, FL 34228

  LONGBOAT KEY HOME WITH WATER VIEWS. BEST PRICE PER SQ FT! Attention boating enthusiasts! Sailboat waterfront home in Longboat Key with Florida's favorite southern exposure. Park your boat on the stationary, or floating dock with a boat lift, 10,000 pounds boat lift, NEW seawall 125 ft., stainless ladder and fillet station. The outdoor kitchen is paved with a cedar pergola, a firepit, kitchen

  Reeny Kaney RE/MAX ALLIANCE GROUP

  690 Jungle Queen Way, Longboat Key, FL 34228
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  /60

  $6,900 per month

  • 2 Beds
  • 2.5 Baths
  • 1,440 Sq Ft
  • House for Rent

  535 Forest Way, Longboat Key, FL 34228

  Welcome to your perfect coastal escape in the heart of Cedars East on Longboat Key, Florida! Professionally managed by Gulf Coast Vacation Rentals, this chic, playful, and stylish 3-story, 2-bedroom, 2-bathroom townhome is nestled in one of the island’s most sought-after communities—offering a unique blend of tropical charm, resort-style amenities, and a peaceful coastal atmosphere.Step

  Andy Moore GULF COAST REALTY & MANAGEMENT

  535 Forest Way, Longboat Key, FL 34228
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  /2

  $475,000 Sold Jul 25, 2025

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

  • 2 Beds
  • 2 Baths
  • 1,441 Sq Ft
  • Built 1969

  Last Sold Summary

  • 32% Below List Price
  • $330/SF
  • 163 Days On Market

  Current Estimated Value $459,515

  Last Listing Agent Shayla Twit CORCORAN DWELLINGS REALTY

  6750 Gulf of Mexico Dr Unit 153, Longboat Key, FL 34228
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  /49

  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

  Last Listing Agent Patrick Brogley KELLER WILLIAMS ON THE WATER S
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  /53

  $625,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  1935 Gulf of Mexico Dr Unit G7402, Longboat Key, FL 34228

  A must-see, this exceptional two-bedroom, two-bath penthouse is the only residence in Seaplace with no shared walls, offering unparalleled privacy and tranquility. Fully remodeled in 2019, the home features a designer kitchen with quartz countertops, custom cabinetry and premium appliances, seamlessly complemented by elegant soft grey laminate hardwood flooring throughout. A spacious lanai spans

  Rita Pogany PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1935 Gulf of Mexico Dr Unit G7402, Longboat Key, FL 34228
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  /100

  $25,000 per month

  • 1 Bed
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228

  Welcome Serenity Oasis, your paradise at The Residences at the St.Regis on Longboat Key—where luxury, elegance, and coastal charm converge in this stunning 1-bedroom, 2-bathroom condo. From the moment the elevator opens directly into your private entryway, you’ll be captivated by the exquisite design and attention to detail throughout this sophisticated retreat. The expansive living room is

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228
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  /2

  $950,000 Sold Mar 18, 2026

  2323 Harbour Oaks Dr, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 2,395 Sq Ft
  • Built 1986

  Last Sold Summary

  • 13% Below List Price
  • $397/SF
  • 108 Days On Market

  Current Estimated Value $1,007,010

  Last Listing Agent Steven Moore MICHAEL SAUNDERS & COMPANY

  2323 Harbour Oaks Dr, Longboat Key, FL 34228
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  /50

  Est $1,442,353 Not Listed For Sale

  1485 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228

  • 2 Beds
  • 2.5 Baths
  • 1,839 Sq Ft
  • Built 1981

  1485 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228

  Last Sold Summary

  • 7% Below List Price
  • $843/SF
  • 39 Days On Market

  Last Sold Price $1,550,000

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY
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  /70

  $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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  /42

  $7,800 per month

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

  4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  SEASONAL: Stunning Gulf views and beautiful sunsets from this spacious, immaculate turnkey furnished 2-bedroom, 2 bath split plan corner unit. Featuring 2 tiled screen enclosed lanais that overlooking lush garden, pools and, of course, serene beach views. This turnkey residence comes complete with cable & wifi, in unit washer/dryer, large walk-in closets and covered parking. The Master suite

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  /2

  $1,175,000 Sold Feb 20, 2026

  747 Marbury Ln, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 2,353 Sq Ft
  • Built 1968

  Last Sold Summary

  • 18% Below List Price
  • $499/SF
  • 72 Days On Market

  Current Estimated Value $1,359,982

  Last Listing Agent Michael Busch COLDWELL BANKER REALTY

  747 Marbury Ln, Longboat Key, FL 34228
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  /2

  Est $717,099 Not Listed For Sale

  750 Saint Judes Dr N, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,246 Sq Ft
  • Built 1958

  750 Saint Judes Dr N, Longboat Key, FL 34228

  Last Sold Summary

  • 20% Above List Price
  • $482/SF
  • 134 Days On Market

  Last Sold Price $600,000

  Last Listing Agent Chevon Eaton CHEVON EATON
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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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  /46

  $7,000 per month

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

  2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228

  RARELY AVAILABLE! This absolutely gorgeous fully furnished 2BR/2BA Condo at Islander Club – Just steps from the Beach! Start living the island lifestyle in this beautifully updated, furnished 2-bedroom, 2-bath condo at the Islander Club on South Longboat Key! This turnkey rental is ready for immediate enjoyment—just bring your suitcase. Enjoy a bright, open layout with floor-to-ceiling hurricane

  Michele Conn PREFERRED SHORE LLC

  2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228
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  /2

  $1,420,000 Sold Aug 13, 2025

  455 Longboat Club Rd Unit 407, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,410 Sq Ft
  • Built 1990

  Last Sold Summary

  • 25% Below List Price
  • $589/SF
  • 104 Days On Market

  Current Estimated Value $1,493,896

  Last Listing Agent Stacy Hanan MICHAEL SAUNDERS & COMPANY

  455 Longboat Club Rd Unit 407, Longboat Key, FL 34228
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  /2

  Est $7,844,370 Not Listed For Sale

  60 Lighthouse Point Dr, Longboat Key, FL 34228

  • 5 Beds
  • 8 Baths
  • 7,170 Sq Ft
  • Built 2000

  60 Lighthouse Point Dr, Longboat Key, FL 34228

  Last Sold Summary

  • 23% Below List Price
  • $1,416/SF
  • 185 Days On Market

  Last Sold Price $10,150,000

  Last Listing Agent Candy Swick CANDY SWICK & COMPANY
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  /58

  $2,499,000

  • 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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  /85

  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 928 Sq Ft
  • Condo for Rent

  1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228

  LONGBOAT KEY "SEAPLACE" CONDOMINIUM LOCATED ON THE GULF SIDE. 2 MONTH MINIMUM REQUIRED. SEASON 2027 JAN-APRIL $6,500/MONTH. BOOKED FOR FEB-APRIL 2026. Immaculate, Turnkey Furnished 2 bedrooms/2-bathroom condo on the 4th floor, located in the sought after Seaplace, a resort style community on the beautiful Barrier Island of Longboat Key. Upon entering the unit, you are met with a light, bright and

  Chrissie Cummings JENNETTE PROPERTIES INC

  1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228
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  $1,275,000 Sold Apr 24, 2025

  380 Gulf of Mexico Dr Unit 513, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 2,490 Sq Ft
  • Built 1994

  Last Sold Summary

  • 15% Below List Price
  • $512/SF
  • 131 Days On Market

  Current Estimated Value $1,335,900

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

  380 Gulf of Mexico Dr Unit 513, Longboat Key, FL 34228
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  Not Listed For Sale

  3710 Gulf of Mexico Dr Unit G1, Longboat Key, FL 34228

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

  3710 Gulf of Mexico Dr Unit G1, Longboat Key, FL 34228

  Last Sold Summary

  • $392/SF
  • 0 Days On Market

  Last Sold Price $345,000

  Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC
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  /57

  $7,800,000

  • 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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  /45

  $6,500 per month

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

  3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228

  2-bed, 2-bath seasonal rental paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy deeded beach access and the community’s private beach area, complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on

  Dakota Magnus FLORIDA GALLERY REAL ESTATE

  3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
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  $108,000 Sold Sep 30, 2025

  72 Main Street Dr, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 780 Sq Ft
  • Built 1965

  Last Sold Summary

  • $138/SF

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  72 Main Street Dr, Longboat Key, FL 34228
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  Est $3,705,455 Not Listed For Sale

  1241 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

  • 3 Beds
  • 5 Baths
  • 3,400 Sq Ft
  • Built 1996

  1241 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

  Last Sold Summary

  • 7% Below List Price
  • $1,176/SF
  • 278 Days On Market

  Last Sold Price $4,000,000

  Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY
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  /34

  $595,000 Open Sat 1PM - 4PM

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

  5260 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

  Welcome to your tropical retreat on Longboat Key! This newly renovated 2-bedroom, 2-bath ground-floor LARGER END unit, with additional windows blends light coastal charm with modern comfort in a sought-after Gulf-to-Bay community. Thoughtful upgrades include neutral tile flooring throughout (no carpet), crown molding, upgraded baseboards, fresh interior paint, impact-rated PGT windows and

  Debbie McHardy COLDWELL BANKER REALTY

  5260 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228
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  $18,000 per month

  • 2 Beds
  • 2.5 Baths
  • 2,143 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228

  2027 Season Rental Rate will be $24,500. The Residences at The St. Regis Longboat Key offer an exceptional blend of ultra-luxury living and world-class resort amenities on the pristine shores of the Gulf of Mexico. This exclusive beachfront community features exquisitely designed residences with soaring ceilings, floor-to-ceiling glass doors, and panoramic sunrise-to-sunset views. The gourmet

  Melissa Gissinger MICHAEL SAUNDERS & COMPANY

  1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
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  $1,465,000 Sold Aug 28, 2025

  501 Reclinata Dr, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,784 Sq Ft
  • Built 2002

  Last Sold Summary

  • 18% Below List Price
  • $526/SF
  • 160 Days On Market

  Current Estimated Value $1,532,235

  Last Listing Agent Barbara Najmy STARZ REAL ESTATE, LLC

  501 Reclinata Dr, Longboat Key, FL 34228
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  /80

  Est $1,492,342 Not Listed For Sale

  2020 Harbourside Dr Unit 434/435, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,462 Sq Ft
  • Built 1984

  2020 Harbourside Dr Unit 434/435, Longboat Key, FL 34228

  Last Sold Summary

  • 14% Below List Price
  • $705/SF
  • 0 Days On Market

  Last Sold Price $1,735,000

  Last Listing Agent Terri Thacker Michael Saunders

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