Longboat Key, FL Homes

• 

  

  

  /37

  $799,000

  • Land
  • 6,534 Sq Ft
  • $5,326,667 per Acre

  766 Saint Judes Dr N, Longboat Key, FL 34228

  The Ultimate Boater's Foundation! Rare Canal-Front Lot with Twin Lifts & New Seawall! This prime, cleared canal-front lot offers the most turn-key building opportunity on Longboat Key. While other buyers are stuck in the permitting phase for marine infrastructure, this one already has it complete and you can dock your fleet on day one. Unmatched Infrastructure Value:• Brand New Seawall: 100

  

  Nikki Spirakis

  BRG REAL ESTATE INC

  766 Saint Judes Dr N, Longboat Key, FL 34228
• 

  

  

  /57

  $10,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Condo for Rent

  519 Bayport Way Unit 519, Longboat Key, FL 34228

  Seasonal rental in Bayport Beach and Tennis Club which is a beautiful, established, award-winning, amenity-rich community with immediate access to a peaceful private beach that continues in both directions for miles along the Gulf of Mexico shore. The complex includes a large pool surrounded by flowering trees, four immaculately maintained clay tennis courts, fitness center, a large clubhouse,

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  519 Bayport Way Unit 519, Longboat Key, FL 34228
• 

  

  /2

  $1,300,000

  Sold Mar 25, 2026

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

  • 2 Beds
  • 2 Baths
  • 1,551 Sq Ft
  • Built 1975

  Last Sold Summary

  • 16% Below List Price
  • $838/SF
  • 214 Days On Market

  Current Estimated Value $1,322,522

  Last Listing Agent Doug Parks MICHAEL SAUNDERS & COMPANY

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

  

  /2

  Est $67,490

  Not Listed For Sale

  408 Gulf of Mexico Dr Unit 2233, Longboat Key, FL 34228

  • Studio
  • Built 1987

  408 Gulf of Mexico Dr Unit 2233, Longboat Key, FL 34228

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY
• 

  

  

  /17

  $695,000

  • Land
  • 10,018 Sq Ft
  • $3,021,739 per Acre

  561 Gulf Bay Rd, Longboat Key, FL 34228

  Create your custom coastal retreat or bring the seller’s thoughtfully prepared plans to life at 561 Gulf Bay Road. This rare 9,990-square-foot vacant homesite is ideally located in the heart of Longboat Key, between the charm of Anna Maria Island and the sophistication of St. Armands Circle. Bordering the 32-acre Joan M. Durante Community Park, the property offers exceptional privacy, peaceful

  

  Gregory Claxton

  PREFERRED SHORE LLC

  561 Gulf Bay Rd, Longboat Key, FL 34228
• 

  

  /54

  $6,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Condo for Rent

  517 Bayport Way Unit 517, Longboat Key, FL 34228

  Gorgeous Inside! Furnished Rental at the exceptional Bayport Beach and Tennis Club. Single story end unit with private entrance. Very Private screened lanai and patio area. Amenities abound at this beautifully landscaped Beach and Tennis Club. Four professional quality Hart-Tru Clay Courts with ball machine, Junior Olympic (heated) swimming pool, ping pong table, bocce ball court, fitness center

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  517 Bayport Way Unit 517, Longboat Key, FL 34228
• 

  /2

  $2,725,000

  Sold Jun 26, 2026

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

  • 3 Beds
  • 3.5 Baths
  • 2,634 Sq Ft
  • Built 1994

  Last Sold Summary

  • 21% Below List Price
  • $1,035/SF
  • 188 Days On Market

  Current Estimated Value $3,034,734

  Last Listing Agent Reid Murphy DEVELOPERS REALTY LBK, INC

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

  

  /88

  Est $664,596

  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

  • 49 Days On Market

  Last Listing Agent Judy Kepecz-Hays COLDWELL BANKER REALTY
• 

  

  /51

  $1,025,000

  $70K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 1,175 Sq Ft

  4485 Gulf of Mexico Dr Unit 804, Longboat Key, FL 34228

  Under contract-accepting backup offers. Renovated direct Gulf-front 2BR/2BA on Longboat Key. End-unit 8th-floor condo at The Arbomar, panoramic sunset views, pets allowed, hurricane-protected. For buyers seeking a move-in-ready beachfront residence on Longboat Key, this renovated direct Gulf-front end unit at The Arbomar delivers updated condition and views that don't quit. The 8th-floor

  

  Julie Larson

  WHITE SANDS REALTY GROUP FL

  4485 Gulf of Mexico Dr Unit 804, Longboat Key, FL 34228
• 

  

  /40

  $10,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,514 Sq Ft
  • Condo for Rent

  615 Dream Island Place Unit 201, Longboat Key, FL 34228

  BRING YOUR BOAT, deeded private boat slip that accommodates up to a 60 ft boat INCLUDED! Picturesque Waterview of Sarasota Bay and easy access by boat to the Gulf. Recently renovated with high end appliances, finishes and designer furniture. The Harbor Villa Club Complex consists of 38 condos in a 3-story plus pool, spa, community boat ramp, kayak launch/storage, 3 tennis/pickle ball courts,

  

  William Glade

  WILLIAM GLADE LIC. REAL ESTATE BROKER

  615 Dream Island Place Unit 201, Longboat Key, FL 34228
• 

  /2

  $631,000

  Sold Aug 28, 2025

  826 Bayport Way Unit 826, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,676 Sq Ft
  • Built 1981

  Last Sold Summary

  • 30% Below List Price
  • $376/SF
  • 347 Days On Market

  Current Estimated Value $691,675

  Last Listing Agent Dennis Girard PREMIER SOTHEBY'S INTERNATIONAL REALTY

  826 Bayport Way Unit 826, Longboat Key, FL 34228
• 

  

  /24

  Est $1,013,264

  Not Listed For Sale

  628 Lyons Ln, Longboat Key, FL 34228

  628 Lyons Ln, Longboat Key, FL 34228

  Last Sold Summary

  • 101 Days On Market

  Last Listing Agent JoDene Moneuse MICHAEL SAUNDERS & COMPANY
• 

  

  /53

  $289,900

  $8K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 800 Sq Ft

  3740 Gulf of Mexico Dr Unit 5-A, Longboat Key, FL 34228

  Longboat Key Living! Enjoy the private beach directly across the street! 2 bedroom 2 bath home located in Twin Shores Beach & Marina Community. Island life is waiting for you. This home offers updated granite counters in the kitchen, 2 updated bathrooms and ample living space. The living/ Dining room combo is large enough to entertain your friends, family and neighbors. Enjoy some of the best

  

  Jill Young

  CENTURY 21 INTEGRA

  3740 Gulf of Mexico Dr Unit 5-A, Longboat Key, FL 34228
• 

  

  /64

  $11,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,531 Sq Ft
  • Condo for Rent

  724 Bayport Way Unit 724, Longboat Key, FL 34228

  STUNNING GULF VIEWS! Enjoy the sparkling glimmer of the morning waters and picturesque sunsets from almost every room. This meticulously maintained 2 bedroom, 2 bathroom furnished condominium features an open concept floor plan with expansive Living/Dining/Kitchen area. The generous size primary bedroom with adjoining bathroom includes a double vanity, separate shower, a walk-in closet and a

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  724 Bayport Way Unit 724, Longboat Key, FL 34228
• 

  /2

  $625,000

  Sold Jun 03, 2026

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

  • 2 Beds
  • 2 Baths
  • 1,561 Sq Ft
  • Built 1975

  Last Sold Summary

  • 12% Below List Price
  • $400/SF
  • 56 Days On Market

  Current Estimated Value $637,940

  Last Listing Agent Ian Addy, PA MICHAEL SAUNDERS & COMPANY

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

  

  /17

  Est $196,767

  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

  • 391 Days On Market

  Last Listing Agent Jennifer Wilson LBRE LLC
• 

  

  /88

  $1,899,000

  • 4 Beds
  • 2.5 Baths
  • 3,009 Sq Ft

  3040 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228

  Welcome to island living on Longboat Key, one of Sarasota's premier barrier island destinations. In Triton Cove, this coastal residence offers direct Gulf Beach access across the street and a lifestyle designed for boating, seasonal use or year-round living along Florida's Gulf Coast. Enjoy nightly sunsets along Gulf of Mexico Drive or experience world-class dining and shopping on nearby St.

  

  Frank Lambert

  PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3040 Gulf of Mexico Dr Unit 3, Longboat Key, FL 34228
• 

  

  /87

  $6,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,601 Sq Ft
  • Condo for Rent

  817 Bayport Way Unit 817, Longboat Key, FL 34228

  STUNNING BAY VIEWS! Enjoy picturesque sunrises from your private deck in this tastefully decorated 2 bedroom, 2 bathroom furnished condominium. This home has an open concept floor plan which features an expansive Living/Dining/Kitchen area. The generous size master bedroom with adjoining bathroom includes a double vanity, separate shower, a walk-in closet and a small alcove that accommodates a

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  817 Bayport Way Unit 817, Longboat Key, FL 34228
• 

  /2

  $385,000

  Sold Nov 20, 2025

  556 Spanish Dr N Unit 154, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • Built 1969

  Last Sold Summary

  • $276/SF

  Current Estimated Value $411,239

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

  556 Spanish Dr N Unit 154, Longboat Key, FL 34228
• 

  /2

  Est $1,047,505

  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

  • 94 Days On Market

  Last Listing Agent Maggie Hicks COLDWELL BANKER REALTY
• 

  

  /36

  $3,590,000

  $1M PRICE DROP

  • 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
• 

  

  /75

  $13,500 Per Month

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft
  • Condo for Rent

  716 Bayport Way Unit 716, Longboat Key, FL 34228

  GORGEOUS INSIDE! This beautifully remodeled ground floor, corner unit, features 3 bedrooms, 2 bathrooms with an open concept floor plan. This home welcomes you into an expansive Living/Dining/Kitchen and offers plenty of natural light. In addition, it boasts a generous size master bedroom with en suite bathroom and an alcove that accommodates a desk and seating area. Bayport Beach & Tennis Club

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  716 Bayport Way Unit 716, Longboat Key, FL 34228
• 

  /2

  $770,000

  Sold Jun 26, 2026

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

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

  Last Sold Summary

  • 38% Below List Price
  • $553/SF
  • 445 Days On Market

  Current Estimated Value $936,851

  Last Listing Agent Donna Wrobel BERKSHIRE HATHAWAY HOMESERVICE

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

  /2

  Est $3,247,638

  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

  • 230 Days On Market

  Last Listing Agent Laura Rode KW COASTAL LIVING III
• 

  

  /38

  $1,270,000

  $100K PRICE DROP

  • Land
  • 17,859 Sq Ft
  • $3,097,561 per Acre

  560 Gulf Bay Rd, Longboat Key, FL 34228

  Back on the Market! RARE DOUBLE-SIZED ESTATE LOT ON LONGBOAT KEY – 18,000 SQ FT OF ISLAND LUXURY READY FOR YOUR VISION. Opportunities like this are few and far between. Nestled in one of the most coveted areas of Longboat Key, this expansive 18,000-square-foot estate lot at 560 Gulf Bay Road offers a blank canvas for your dream coastal retreat—just steps from the sugar-white sands of the Gulf of

  

  Gregory Claxton

  PREFERRED SHORE LLC

  560 Gulf Bay Rd, Longboat Key, FL 34228
• 

  

  /62

  $6,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft
  • Condo for Rent

  741 Bayport Way Unit 741, Longboat Key, FL 34228

  ABSOLUTELY GORGEOUS INSIDE! Bayport Beach & Tennis Club is an amenity-rich community at sea's edge and is situated in the middle of Longboat Key. This 2 bedroom, 2 bathroom fully FURNISHED rental is tastefully and brilliantly decorated. This residence offers a wonderful retreat as a Seasonal rental or a shorter Monthly respite. Bayporters' enjoy an active island lifestyle with 4 Har Tru tennis

  

  Antonietta Car

  KELLER WILLIAMS SUBURBAN TAMPA

  741 Bayport Way Unit 741, Longboat Key, FL 34228
• 

  /2

  $917,000

  Sold May 21, 2026

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

  • 2 Beds
  • 2 Baths
  • 961 Sq Ft
  • Built 1983

  Last Sold Summary

  • 91% Below List Price
  • $954/SF
  • 164 Days On Market

  Current Estimated Value $892,621

  Last Listing Agent Patrick Brogley KELLER WILLIAMS ON THE WATER S

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

  

  /48

  Est $2,174,651

  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

  • 11 Days On Market

  Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY
• 

  

  /90

  $899,000

  $100K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,673 Sq Ft

  580 Linley St, Longboat Key, FL 34228

  Discover this stunning, completely renovated interiors two-bedroom, two-bath home nestled in the Historic Longbeach Village on the quiet north end of Longboat key. More than just a home, this is a true coastal lifestyle. Perfectly positioned just a five minute walk to the largest public beach on Longboat Key. you'll enjoy effortless access to sugar-white sand, breathtaking Gulf sunsets, and

  

  Sharon Hightower

  RE/MAX ALLIANCE GROUP

  580 Linley St, Longboat Key, FL 34228
• 

  

  /34

  $7,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,909 Sq Ft
  • Condo for Rent

  737 Bayport Way Unit D, Longboat Key, FL 34228

  BAYPORT TENNIS AND RAQUET CLUB has all the amenities including direct GULF Access. This tastefully furnished, one floor, three bedroom, two bathroom condo in the Bayport Beach and Tennis Club offers spacious living areas; Wonderful views of the Gulf of Mexico; and beautiful outdoor space. Large patios with tropical Gulf of Mexico views - perfect for morning coffee and sunset cocktails. Two

  

  Marianne LeBar

  CENTURY 21 ROSEBAY

  737 Bayport Way Unit D, Longboat Key, FL 34228
• 

  /2

  $2,450,000

  Sold Jul 15, 2026

  3408 Fair Oaks Ln, Longboat Key, FL 34228

  • 5 Beds
  • 5 Baths
  • 4,510 Sq Ft
  • Built 1992

  Last Sold Summary

  • 12% Below List Price
  • $543/SF
  • 189 Days On Market

  Current Estimated Value $2,455,322

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  3408 Fair Oaks Ln, Longboat Key, FL 34228
• 

  

  /66

  Est $3,521,262

  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

  • 35 Days On Market

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY
• 

  

  /20

  $995,000

  $280K PRICE DROP

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

  1105 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

  Beachplace at Longboat Key: Major price reduction for this Gulf-front luxury and rental-friendly, turnkey furnished investment opportunity! An iconic condominium in the mid-century modern style, Beachplace was constructed under the direction of Tim Siebert, one of the leaders of the Sarasota School of Architecture, and spans 31 acres with a quarter mile of Gulf beachfront. This price reduction

  

  Tom Aposporos

  DUNCAN REAL ESTATE, INC.

  1105 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
• 

  

  /30

  $7,750 Per Month

  • 3 Beds
  • 3 Baths
  • 1,672 Sq Ft
  • Condo for Rent

  5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228

  Available Dec 20- April .Steps to the Sand – 3BR/3BA Beachfront Condo with Heated Pool & Spa | Longboat KeyEnjoy the best of beachfront living at 5611 Gulf of Mexico Drive, Unit 105 — a beautifully appointed three-bedroom, three-bath condo located in a boutique community directly on the beach. You’re just steps away from the soft sand and turquoise waters of the Gulf of Mexico.This

  

  William Glade

  WILLIAM GLADE LIC. REAL ESTATE BROKER

  5611 Gulf of Mexico Dr Unit 5, Longboat Key, FL 34228
• 

  /2

  $3,075,000

  Sold Mar 02, 2026

  5382 Sandhamn Place, Longboat Key, FL 34228

  • 4 Beds
  • 3.5 Baths
  • 3,330 Sq Ft
  • Built 1996

  Last Sold Summary

  • 5% Below List Price
  • $923/SF
  • 15 Days On Market

  Current Estimated Value $3,080,491

  Last Listing Agent Nora Johnson MICHAEL SAUNDERS & COMPANY

  5382 Sandhamn Place, Longboat Key, FL 34228
• 

  

  /60

  Est $1,527,266

  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

  • 79 Days On Market

  Last Listing Agent Courtney Green PREMIER SOTHEBYS INTL REALTY
• 

  

  /84

  $874,500

  • 2 Beds
  • 2 Baths
  • 1,409 Sq Ft

  1000 Longboat Club Rd Unit 304, Longboat Key, FL 34228

  Experience elevated coastal living in this beautifully renovated two-bedroom, two-bath golf-front condominium, ideally situated behind the gates of the prestigious Longboat Key Club in the sought-after community of Privateer South on Longboat Key. Thoughtfully redesigned with a refined coastal aesthetic, this residence showcases a seamless blend of modern elegance and relaxed waterfront living.

  

  Judy Kepecz-Hays

  COLDWELL BANKER REALTY

  1000 Longboat Club Rd Unit 304, Longboat Key, FL 34228
• 

  

  /57

  $24,750 Per Month

  • 3 Beds
  • 3.5 Baths
  • 2,940 Sq Ft
  • Condo for Rent

  1511 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  Offered at $24,750 per month for 3 months in 2027! - Come be on the beach! Rarely available on the south end of Longboat Key, a 3 bedroom + den, 3 1/2 bath DIRECT Beachfront 3-month (90 days total) rental is now available for this coming 2027 winter and spring season. This large 2940 +/- sq ft beachfront retreat is situated on the south side of this building which offers stunning 180-degree beach

  Carol Aviles MICHAEL SAUNDERS & COMPANY

  1511 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
• 

  /2

  $18,990,000

  Sold Jul 24, 2026

  612 Juan Anasco Dr, Longboat Key, FL 34228

  • 6 Beds
  • 9 Baths
  • 9,243 Sq Ft
  • Built 2024

  Last Sold Summary

  • 27% Below List Price
  • $2,055/SF
  • 482 Days On Market

  Current Estimated Value $7,129,011

  Last Listing Agent Charles Buky COLDWELL BANKER REALTY

  612 Juan Anasco Dr, Longboat Key, FL 34228
• 

  

  /36

  Est $989,784

  Not Listed For Sale

  230 Sands Point Rd Unit 3605, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 634 Sq Ft
  • Built 1982

  230 Sands Point Rd Unit 3605, Longboat Key, FL 34228

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Norma Mladineo COLDWELL BANKER REALTY

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