Longboat Key, FL Homes

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  /49

  $5,799,000

  New Construction

  • 5 Beds
  • 7 Baths
  • 4,216 Sq Ft

  530 Chipping Ln, Longboat Key, FL 34228

  Introducing the newest custom residence by Brista Homes, where exceptional craftsmanship and thoughtful design come together in a limited and highly refined offering. Nestled along a quiet canal in the sought-after waterfront community of Country Club Shores, this 4216 square-foot residence captures the essence of the Longboat Key boating lifestyle. With desirable south-facing rear exposure,

  Gina Ursini BRISTA REALTY LLC

  530 Chipping Ln, Longboat Key, FL 34228
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  /71

  $15,000 Per Month

  • 3 Beds
  • 3 Baths
  • 1,710 Sq Ft
  • Condo for Rent

  1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

  LOCATION, LOCATION, LOCATION!!! Gorgeous beach front PENTHOUSE condo available to rent in the sought after Longboat Key community of the Players Club. Enjoy views of the Gulf of Mexico, lush grounds and sparkling sandy beaches from the expansive terrace of this light and bright, corner unit, turnkey furnished condo. The property has three bedrooms, three bathrooms, living room/dining room

  C. Alison Hunter JENNETTE PROPERTIES INC

  1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
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  /2

  $2,100,000

  Sold Jan 16, 2026

  5930 Gulf of Mexico Dr, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 2,570 Sq Ft
  • Built 1988

  Last Sold Summary

  • 22% Below List Price
  • $817/SF
  • 599 Days On Market

  Current Estimated Value $2,155,083

  Last Listing Agent Reid Murphy DEVELOPERS REALTY LBK, INC

  5930 Gulf of Mexico Dr, Longboat Key, FL 34228
• 

  

  

  /53

  Est $851,782

  Not Listed For Sale

  Unlisted Address

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft
  • Built 1963

  Unlisted Address

  Last Sold Summary

  • 136 Days On Market
• 

  

  

  /41

  $1,175,000

  $125K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft

  1135 Gulf of Mexico Dr Unit 505, Longboat Key, FL 34228

  Under contract-accepting backup offers. DIRECT BEACH FRONT VIEWS AND FIFTH FLOOR EXTRORDINARY PANORAMA! Come visit this property soon, as it boasts Two Parking spots, one in garage, near the elevator and one outside near the front door. Reimagined kitchen with lots of cupboard space, all KITCHEN AID appliances, 2019 Air Handler, never rented and barely occupied. Furnished with exquisite taste and

  Jim Weingart COLDWELL BANKER REALTY

  1135 Gulf of Mexico Dr Unit 505, Longboat Key, FL 34228
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  /32

  $2,400 Per Month

  • 2 Beds
  • 2 Baths
  • 1,301 Sq Ft
  • Condo for Rent

  450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228

  Annual furnished rental: Discover the ultimate island lifestyle in this comfortably furnished 2-bedroom, 2 bath, unit located in the highly sought-after community of Bay Harbour on the southern end of Longboat Key. Just minutes from St. Armands Circle, downtown Sarasota, restaurants, shopping, county tennis and pickleball courts, walking trails, parks and of course – Longboat Key public beach

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  450 Gulf of Mexico Dr Unit B303, Longboat Key, FL 34228
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  /2

  $535,000

  Sold Oct 29, 2025

  640 Fox St, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1965

  Last Sold Summary

  • 21% Below List Price
  • $429/SF
  • 168 Days On Market

  Current Estimated Value $574,360

  Last Listing Agent Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  640 Fox St, Longboat Key, FL 34228
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  /28

  Est $2,825,987

  Not Listed For Sale

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

  • 3 Beds
  • 4 Baths
  • 3,045 Sq Ft
  • Built 1996

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

  Last Sold Summary

  • 54 Days On Market
• 

  

  /40

  $1,875,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,394 Sq Ft

  230 Sands Point Rd Unit 3703, Longboat Key, FL 34228

  Under contract-accepting backup offers. Rarely available renovated corner two bedroom at The Resort at Longboat Key Club. Full gulf views from this 7th floor vantage are enjoyed from every room and the corner position offers extra square footage with extra windows. Located behind the gates of the Longboat Key Club, owners will enjoy the coastal contemporary finishes and excellent income history.

  Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  230 Sands Point Rd Unit 3703, Longboat Key, FL 34228
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  /20

  $12,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,293 Sq Ft
  • Condo for Rent

  615 Dream Island Rd Unit 107, Longboat Key, FL 34228

  Welcome to one of the most sought-after condo units in the Harbour Villa Club. This magnificent unit is for rent fully furnished. Opening the front door, you will enjoy a beautiful view of the serene intracoastal waterway and stunning Florida palm trees. No need to mess with an elevator, this first floor unit opens directly to the swimming pool and is only steps away from a 40’ deeded boat slip

  Jerome Henin HENIN REALTY

  615 Dream Island Rd Unit 107, Longboat Key, FL 34228
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  /2

  $625,000

  Sold Dec 19, 2025

  4440 Exeter Dr Unit 206, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,376 Sq Ft
  • Built 1970

  Last Sold Summary

  • $454/SF
  • 4 Days On Market

  Current Estimated Value $646,336

  Last Listing Agent Kara Berger THE SHORELINE FL REALTY LLC

  4440 Exeter Dr Unit 206, Longboat Key, FL 34228
• 

  

  /35

  Est $966,175

  Not Listed For Sale

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

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft
  • Built 1981

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

  Last Sold Summary

  • 224 Days On Market
• 

  

  /43

  $895,000

  $80K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,413 Sq Ft

  3080 Grand Bay Blvd Unit 533, Longboat Key, FL 34228

  As you step into this rarely available Capri floor plan, the entrance sets the stage for an exquisite bayfront experience. Inside, the residence unfolds with white ceramic tile throughout and water views via floor-to-ceiling windows and sliders in every room, creating a bright, private ambiance and a seamless connection to the natural beauty that surrounds you. The 2 large balconies immediately

  Ryan Ackerman COLDWELL BANKER REALTY

  3080 Grand Bay Blvd Unit 533, Longboat Key, FL 34228
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  /24

  $2,500 Per Month

  • 1 Bed
  • 1.5 Baths
  • 761 Sq Ft
  • Condo for Rent

  3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

  AVAILABLE FOR SEASONAL OR ANNUAL RENTAL. 3 MONTH MINIMUM. Beach Harbor Club – Turnkey Furnished Gulf-View Condo. Welcome to your seasonal coastal retreat at the highly desirable Beach Harbor Club on Longboat Key. This beautifully appointed 1-bedroom, 1.5-bath furnished condo offers the perfect blend of comfort, convenience, and island living just steps from the Gulf of Mexico. Inside, you’ll find

  Brigette Marcus NEXTHOME EXCELLENCE

  3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
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  /2

  $1,800,000

  Sold Jun 30, 2025

  612 Weston Pointe Ct, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,612 Sq Ft
  • Built 1993

  Last Sold Summary

  • 10% Below List Price
  • $689/SF
  • 80 Days On Market

  Current Estimated Value $1,790,622

  Last Listing Agent Cindy Schatzle COLDWELL BANKER REALTY

  612 Weston Pointe Ct, Longboat Key, FL 34228
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  /41

  Est $397,511

  Not Listed For Sale

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

  • 2 Beds
  • 2 Baths
  • 1,007 Sq Ft
  • Built 1970

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

  Last Sold Summary

  • 146 Days On Market
• 

  

  /36

  $1,225,277

  Open Sun 1PM - 4PM

  • 2 Beds
  • 2 Baths
  • 1,235 Sq Ft

  2301 Gulf of Mexico Dr Unit 11, Longboat Key, FL 34228

  Experience the tranquility of Gulf-front living from this beautifully updated residence at the prestigious Islander Club on South Longboat Key. Ideally positioned on the highly desirable north side of the building, this exceptional beachfront condominium enjoys a uniquely private setting with expansive views, abundant natural light, and a peaceful atmosphere rarely found in condominium

  Leah George COLDWELL BANKER REALTY

  2301 Gulf of Mexico Dr Unit 11, Longboat Key, FL 34228
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  /31

  $15,000 Per Month

  • 1 Bed
  • 2 Baths
  • 1,556 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 515, 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

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1591 Gulf of Mexico Dr Unit 515, Longboat Key, FL 34228
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  /2

  $190,000

  Sold Mar 12, 2026

  3710 Gulf of Mexico Dr Unit E11, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 248 Sq Ft
  • Built 1962

  Last Sold Summary

  • 5% Below List Price
  • $766/SF
  • 25 Days On Market

  Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC

  3710 Gulf of Mexico Dr Unit E11, Longboat Key, FL 34228
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  /52

  Est $1,475,786

  Not Listed For Sale

  1055 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Built 1981

  1055 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228

  Last Sold Summary

  • 4 Days On Market
• 

  

  /73

  $449,000

  • 1 Bed
  • 1 Bath
  • 630 Sq Ft

  729 Saint Judes Dr S Unit 3, Longboat Key, FL 34228

  Live that Longboat Key waterfront lifestyle and have your own boat lift without the multi-million dollar price. Cute and conveniently located, this on-grade one bedroom condominium unit that is located on a saltwater canal on Longboat Key, features its own 10,000 lb boat lift, and is one block to the gulf beaches and adjacent to Durante Park. Everything new in 2025, including a washer and dryer

  Steven Schield MICHAEL SAUNDERS & COMPANY

  729 Saint Judes Dr S Unit 3, Longboat Key, FL 34228
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  /21

  $5,000 Per Month

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

  1912 Harbourside Dr Unit 603, 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 a dip

  Victoria Campbell LPT REALTY LLC

  1912 Harbourside Dr Unit 603, Longboat Key, FL 34228
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  /2

  $605,000

  Sold Dec 30, 2025

  1930 Harbourside Dr Unit 136, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,270 Sq Ft
  • Built 1982

  Last Sold Summary

  • 11% Below List Price
  • $476/SF
  • 16 Days On Market

  Current Estimated Value $627,030

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  1930 Harbourside Dr Unit 136, Longboat Key, FL 34228
• 

  

  /31

  Est $957,566

  Not Listed For Sale

  1095 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Built 1981

  1095 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

  Last Sold Summary

  • 226 Days On Market
• 

  

  /57

  $2,100,000

  Open Sat 11AM - 2PM $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,853 Sq Ft

  548 Gunwale Ln, Longboat Key, FL 34228

  Country Club Shores - Completely renovated 3-bedroom, 2-bath canal-front home just three houses from the Bay. Updates include a new flat tile roof (2025), Carrier A/C and A.O. Smith water heater (2024), Pebble Tec pool and paver deck (2024), and newer seawall, dock, and 16,000 lb. boat lift (2.5 years). Enjoy Bay views from the 18 foot x 16 foot Trex dock with lighting and water, plus a 3 foot x

  John August MICHAEL SAUNDERS & COMPANY

  548 Gunwale Ln, Longboat Key, FL 34228
• 

  

  /25

  $8,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,273 Sq Ft
  • Condo for Rent

  2109 Gulf of Mexico Dr Unit 1402, Longboat Key, FL 34228

  LONGBOAT KEY...SUNSET BEACH CLUB II. Nicely appointed 2 bedroom, 2 bath condo, turnkey furnished. Entertainment center in the living room with a flat screen TV. King bed in the master and twin beds in the guest room. Lovely view of the Gulf of Mexico and the pool. Capture beautiful sunsets every night from the balcony. This unit is equipped with everything you will need so you can vacation with

  Teresa Ribaudo JENNETTE PROPERTIES INC

  2109 Gulf of Mexico Dr Unit 1402, Longboat Key, FL 34228
• 

  /2

  $555,000

  Sold May 15, 2026

  4234 Gulf of Mexico Dr Unit J1, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Built 1973

  Last Sold Summary

  • 7% Below List Price
  • $483/SF
  • 53 Days On Market

  Current Estimated Value $591,575

  Last Listing Agent Mike Seamon PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4234 Gulf of Mexico Dr Unit J1, Longboat Key, FL 34228
• 

  

  /27

  Not Listed For Sale

  3710 Gulf of Mexico Dr Unit G27, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 744 Sq Ft
  • Built 1965

  3710 Gulf of Mexico Dr Unit G27, Longboat Key, FL 34228

  Last Sold Summary

  • 268 Days On Market
• 

  

  /61

  $2,899,000

  $100K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,375 Sq Ft

  535 Sanctuary Dr Unit A603, Longboat Key, FL 34228

  Welcome to refined coastal living at The Sanctuary—an exclusive gulf-side enclave tucked behind the gates of the Longboat Key Club. This beautifully updated 6th-floor residence offers 2BR plus den, 2.5BA, and over 2,375± sq. ft. of sophisticated interiors paired with sweeping wrap-around terraces that capture panoramic views of the Gulf of Mexico, the Links golf course, and the Sarasota skyline.

  Steve and Janet Walter MICHAEL SAUNDERS & COMPANY

  535 Sanctuary Dr Unit A603, Longboat Key, FL 34228
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  /32

  $11,400 Per Month

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Condo for Rent

  1135 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

  Seasonal. Not available Jan - April 2025. Amazing sunsets from this fabulous 5th floor, direct Gulf beach front, 2 BD, 2 BA condo. Meticulously maintained, this condo has everything you need for a care-free beach vacation! Master suite features king size bed, private bath with Gulf view. Guest room offers twin sleeping arrangements with private entrance to bath. For your comfort, there's flat

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  1135 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
• 

  /2

  $1,400,000

  Sold Aug 25, 2025

  2301 Gulf of Mexico Dr Unit 52, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,235 Sq Ft
  • Built 1970

  Last Sold Summary

  • 15% Below List Price
  • $1,134/SF
  • 149 Days On Market

  Current Estimated Value $1,333,429

  Last Listing Agent Doug Parks MICHAEL SAUNDERS & COMPANY

  2301 Gulf of Mexico Dr Unit 52, Longboat Key, FL 34228
• 

  

  /43

  Est $1,265,894

  Not Listed For Sale

  1055 Gulf of Mexico Dr Unit 301 B, Longboat Key, FL 34228

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

  1055 Gulf of Mexico Dr Unit 301 B, Longboat Key, FL 34228

  Last Sold Summary

  • 61 Days On Market
• 

  

  /29

  $1,950,000

  • Land
  • 12,632 Sq Ft
  • $6,724,138 per Acre

  536 Gunwale Ln, Longboat Key, FL 34228

  536 Gunwale Lane, with its south facing waterfront location, is ideally situated for the best of island living. Recently cleared, this highly sought waterfront lot in Country Club Shores offers the perfect opportunity to design and build the legacy home you’ve been dreaming of...enjoy fantastic boating on protected deep water with direct access to the Bay, Intracoastal, and Gulf waters and a

  Jenifer Schwell MICHAEL SAUNDERS & COMPANY

  536 Gunwale Ln, Longboat Key, FL 34228
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  /66

  $7,200 Per Month

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

  3240 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

  Absolutely beautiful turnkey furnished condo at the sought after Portobello on Longboat Key. The meticulously maintained, light and bright two bedroom, two bathroom unit has a combination living room/dining room, separate kitchen with stainless steel appliances, split bedrooms and a washer and dryer in the unit. Newly renovated bathrooms and kitchen with high end finishes round out this fabulous

  C. Alison Hunter JENNETTE PROPERTIES INC

  3240 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
• 

  /2

  $2,000,000

  Sold Oct 15, 2025

  4 Winslow Place, Longboat Key, FL 34228

  • 4 Beds
  • 3 Baths
  • 3,288 Sq Ft
  • Built 1963

  Last Sold Summary

  • $608/SF
  • 0 Days On Market

  Current Estimated Value $2,011,565

  Last Listing Agent Kaisen Mitchell COLDWELL BANKER REALTY

  4 Winslow Place, Longboat Key, FL 34228
• 

  

  /54

  Est $651,102

  Not Listed For Sale

  5265 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,128 Sq Ft
  • Built 1974

  5265 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  Last Sold Summary

  • 0 Days On Market
• 

  

  /71

  $2,750,000

  $500K PRICE DROP

  • 3 Beds
  • 4.5 Baths
  • 3,260 Sq Ft

  4561 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

  Spectacular North west corner three bedroom condo with direct beachfront views at The Grande, a oasis with only 8 residences. This is Florida living at its very best! This second floor corner location has breathtaking views of the Gulf of Mexico and miles of beautiful sandy beach plus some views of Sarasota Bay and amazing sunsets. A fantastic wrapping terrace on the Gulfside offers outdoor

  Reid Murphy DEVELOPERS REALTY LBK, INC

  4561 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
• 

  

  /12

  $30,000 Per Month

  • 1 Bed
  • 1.5 Baths
  • 1,684 Sq Ft
  • Condo for Rent

  1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228

  Enter the unit from a private elevator which features a spacious, open-plan living area with large windows allowing natural light and incredible views of the surrounding landscape and Sarasota Bay. The lavish living space opens up onto a stunning balcony that overlooks Sarasota Bay and the St. Regis grounds and includes a gas grill. The stylish living area includes high-end furniture with a

  Larry Starr SVN COMMERCIAL ADVISORY GROUP

  1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
• 

  /2

  $1,725,000

  Sold Feb 12, 2026

  2550 Harbourside Dr Unit 322, Longboat Key, FL 34228

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

  Last Sold Summary

  • 25% Below List Price
  • $610/SF
  • 323 Days On Market

  Current Estimated Value $1,728,162

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  2550 Harbourside Dr Unit 322, Longboat Key, FL 34228
• 

  /2

  Est $413,150

  Not Listed For Sale

  641 Fox St, Longboat Key, FL 34228

  641 Fox St, Longboat Key, FL 34228

  Last Sold Summary

  • 6 Days On Market

Showing Results 441 - 480, Page 12 of 18