Longboat Key, FL Homes

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  /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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  /20

  $7,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,896 Sq Ft
  • Condo for Rent

  2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  Absolutely stunning waterfront turnkey furnished rental property on Longboat Key. This unit features beautiful sunsets daily from your private balcony and there is a shared seating area facing east if you prefer sunrises. This spacious 2/2 split floor plan has been fully renovated and is tastefully furnished. The property boasts amenities such as a beachfront pool, workout room, tennis court, and

  Christian Higgins ANDRE LECLAIR PROPERTIES LLC

  2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
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  /2

  $3,170,000 Sold Aug 08, 2025

  689 Lands End Dr, Longboat Key, FL 34228

  • 4 Beds
  • 4.5 Baths
  • 3,254 Sq Ft
  • Built 2005

  Last Sold Summary

  • 17% Below List Price
  • $974/SF
  • 140 Days On Market

  Current Estimated Value $3,194,355

  Last Listing Agent Matthew Voss PREFERRED SHORE LLC

  689 Lands End Dr, Longboat Key, FL 34228
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  /28

  Est $2,911,827 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

  • 6% Below List Price
  • $1,018/SF
  • 54 Days On Market

  • Last Sold Price $3,100,000
  • Jul 10, 2023

  Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY
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  /61

  $2,999,000

  • 2 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
• 

  

  /23

  $5,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,561 Sq Ft
  • Condo for Rent

  5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

  Pristine Gulf Beachfront on Longboat Key Welcome to this beautifully updated 2-bedroom, 2-bathroom luxury beachside retreat located in The Shore on mid-Longboat Key. This inviting second-floor condo offers stunning Gulf views and is just steps from the powdery white sand and crystal-clear waters—an ideal setting for a relaxed island getaway. Highlights-Sweeping Gulf views from living room and

  Matt Darak DARAK GROUP INCORPORATED

  5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
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  /2

  $1,575,000 Sold Jun 11, 2025

  1906 Harbour Links Cir Unit 14, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,180 Sq Ft
  • Built 2002

  Last Sold Summary

  • 7% Below List Price
  • $722/SF
  • 124 Days On Market

  Current Estimated Value $1,583,633

  Last Listing Agent Charles Totonis PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1906 Harbour Links Cir Unit 14, Longboat Key, FL 34228
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  /67

  Est $1,574,663 Not Listed For Sale

  3637 Fair Oaks Place Unit 1, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,724 Sq Ft
  • Built 1999

  3637 Fair Oaks Place Unit 1, Longboat Key, FL 34228

  Last Sold Summary

  • 17% Above List Price
  • $496/SF
  • 37 Days On Market

  • Last Sold Price $1,350,000
  • Apr 26, 2023

  Last Listing Agent Jennifer Linehan Michael Saunders
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  /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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  /25

  $8,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft
  • Condo for Rent

  1925 Gulf of Mexico Dr Unit G8208, Longboat Key, FL 34228

  Beautiful Beachfront at SEAPLACE Condominium on LONGBOAT KEY. THREE bedroom turnkey FURNISHED READY FOR YOUR THRE MONTH OR LONGER STAY. Primary Bedroom has two full beds, queen in second bedroom, and two twins in the third bedroom. Spacious lanai with beautiful beach views. The Seaplace amenities include two large beachfront pools, fitness center, clubhouse, tennis courts and a great expansive

  Jane Hunter JENNETTE PROPERTIES INC

  1925 Gulf of Mexico Dr Unit G8208, Longboat Key, FL 34228
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  /2

  $740,000 Sold Jan 15, 2026

  2120 Harbourside Dr Unit 617, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 2,039 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Below List Price
  • $363/SF
  • 44 Days On Market

  Current Estimated Value $758,064

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  2120 Harbourside Dr Unit 617, Longboat Key, FL 34228
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  /31

  Est $731,329 Not Listed For Sale

  4401 Gulf of Mexico Dr Unit 803, Longboat Key, FL 34228

  • 1 Bed
  • 1 Bath
  • 955 Sq Ft
  • Built 1972

  4401 Gulf of Mexico Dr Unit 803, Longboat Key, FL 34228

  Last Sold Summary

  • 14% Below List Price
  • $890/SF
  • 41 Days On Market

  • Last Sold Price $850,000
  • May 02, 2023

  Last Listing Agent Jerry Barnes REALTY SERVICES INC
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  /71

  $2,750,000

  • 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
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  /83

  $15,000 Per Month

  • 1 Bed
  • 1.5 Baths
  • 1,721 Sq Ft
  • Condo for Rent

  1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228

  Annual Furnished Rental Available at The Residences at The St. Regis Longboat Key mark the debut of a truly iconic address — the first branded residential community and ultra-luxury five-star resort on the Gulf of Mexico. Welcome home to the legendary service and sophistication of St. Regis, paired with the tranquil allure of a seaside retreat on the exclusive barrier island of Longboat Key,

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
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  /2

  $1,538,000 Sold Oct 08, 2025

  2675 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,180 Sq Ft
  • Built 1979

  Last Sold Summary

  • 8% Below List Price
  • $706/SF
  • 46 Days On Market

  Current Estimated Value $1,577,804

  Last Listing Agent Sandra Endres COLDWELL BANKER REALTY

  2675 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228
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  /35

  Est $974,287 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

  • 2% Below List Price
  • $547/SF
  • 224 Days On Market

  • Last Sold Price $995,000
  • Sep 19, 2023

  Last Listing Agent Ian Addy, PA Michael Saunders
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  /83

  $1,725,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,365 Sq Ft

  340 Gulf of Mexico Dr Unit 124, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Only patio photo is virtually staged, no patio furniture is included. Welcome to Tangerine Bay Club, the southernmost condominium on Longboat Key, where refined sophistication meets resort-style livingThis exceptional direct Bayfront end residence offers panoramic views of Sarasota Bay and the feel of a

  Debra Pitell-Hauge MICHAEL SAUNDERS & COMPANY

  340 Gulf of Mexico Dr Unit 124, Longboat Key, FL 34228
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  /6

  $3,250 Per Month

  • 2 Beds
  • 2 Baths
  • 1,427 Sq Ft
  • House for Rent

  676 El Centro, Longboat Key, FL 34228

  Experience the best of island living at this luxurious, completely remodeled Longboat Key villa retreat. Renovated from top to bottom, this stunning 2-bedroom, 2-bath residence blends modern elegance with relaxed coastal charm just steps from the Gulf beach. Inside, you’ll find a bright, open layout with high-end finishes throughout. The home features two luxurious full bathrooms, thoughtfully

  Moe Mossa SAVVY AVENUE, LLC

  676 El Centro, Longboat Key, FL 34228
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  /2

  $3,000,000 Sold Mar 04, 2026

  601 Triton Bend, Longboat Key, FL 34228

  • 4 Beds
  • 5 Baths
  • 3,313 Sq Ft
  • Built 2017

  Last Sold Summary

  • 13% Below List Price
  • $906/SF
  • 160 Days On Market

  Current Estimated Value $3,210,325

  Last Listing Agent Gina Ursini BRISTA REALTY LLC

  601 Triton Bend, Longboat Key, FL 34228
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  /41

  Est $414,568 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

  • 11% Above List Price
  • $372/SF
  • 146 Days On Market

  • Last Sold Price $375,000
  • Oct 18, 2023

  Last Listing Agent Sandi Ward COLDWELL BANKER REALTY
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  /40

  $598,000

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

  4234 Gulf of Mexico Dr Unit E2, Longboat Key, FL 34228

  Exceptional full Bay views, private beach access and kayak launch, and incredible value! This 2BR/2BA retreat at Pelican Harbour & Beach Club delivers the quintessential Longboat Key lifestyle. From its 2nd-floor vantage point, enjoy peaceful sunrises over the Bay and the tranquil fountain view from your screened lanai, surrounded by lush tropical landscaping. Then, end your day with spectacular

  Lenore Treiman MICHAEL SAUNDERS & COMPANY

  4234 Gulf of Mexico Dr Unit E2, Longboat Key, FL 34228
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  /34

  $14,400 Per Month

  • 2 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • House for Rent

  701 Broadway St, Longboat Key, FL 34228

  This charming single-story residence is a meticulous rebuild with an open-concept great room featuring high ceilings, abundant natural light, and a gourmet kitchen equipped with stainless steel appliances and a gas range. The private, fully fenced backyard offers a lagoon style heated swimming pool, separate hot tub, lush tropical landscaping, and the soothing sound of swaying palms. Completely

  Christina Vescovo LPT REALTY, LLC

  701 Broadway St, Longboat Key, FL 34228
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  /2

  $950,000 Sold Jul 15, 2025

  2301 Gulf of Mexico Dr Unit 26, Longboat Key, FL 34228

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

  Last Sold Summary

  • 7% Below List Price
  • $769/SF
  • 60 Days On Market

  Current Estimated Value $980,835

  Last Listing Agent Doug Parks MICHAEL SAUNDERS & COMPANY

  2301 Gulf of Mexico Dr Unit 26, Longboat Key, FL 34228
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  /52

  Est $1,482,483 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

  • 10% Below List Price
  • $1,185/SF
  • 4 Days On Market

  • Last Sold Price $1,650,000
  • May 07, 2024

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY
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  /71

  $648,800

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

  4234 Gulf of Mexico Dr Unit Q2, Longboat Key, FL 34228

  Beautiful, custom 2024 renovated second floor two bedroom, two bathroom Pelican Harbour & Beach Club condo with panoramic Sarasota Bay views plus Deeded Beach access right across the street. Stunning water views across Sarasota Bay are yours from the Great Room, the Primary Bedroom & from your waterfront, covered & screened in Balcony. Entertain your guests here or enjoy your own private dining

  Maruta Miluns MICHAEL SAUNDERS & COMPANY

  4234 Gulf of Mexico Dr Unit Q2, Longboat Key, FL 34228
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  /28

  $10,000 Per Month

  • 3 Beds
  • 3.5 Baths
  • 2,780 Sq Ft
  • Condo for Rent

  455 Longboat Club Rd Unit 401, Longboat Key, FL 34228

  Welcome to Paradise! Beautiful 3 bedroom 3.5 baths, luxury split floor plan condo on LONGBOAT KEY. Behind the gates of Longboat Key Club, known for its privacy and yet close to St. Armand's Circle for dining, shopping, entertainment & cultural offerings of downtown Sarasota. Located on the south end of Longboat Key, this tastefully furnished 4th floor updated unit offers a partial view of the

  Deserea Hardy ROSSI & COMPANY INC

  455 Longboat Club Rd Unit 401, Longboat Key, FL 34228
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  /2

  $1,050,000 Sold Jul 21, 2025

  650 Penfield St, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,579 Sq Ft
  • Built 1978

  Last Sold Summary

  • 19% Below List Price
  • $665/SF
  • 127 Days On Market

  Current Estimated Value $1,032,890

  Last Listing Agent JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  650 Penfield St, Longboat Key, FL 34228
• 

  

  /31

  Est $983,016 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

  • 1% Above List Price
  • $650/SF
  • 226 Days On Market

  • Last Sold Price $977,500
  • Aug 01, 2023

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY
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  /44

  $1,550,000

  • 2 Beds
  • 3.5 Baths
  • 2,550 Sq Ft

  3040 Grand Bay Blvd Unit 213, Longboat Key, FL 34228

  Beautifully positioned within Grand Bay on Longboat Key, this 2-bedroom + den residence offers 2,550 sq ft of light-filled living with a private elevator opening directly into the home. Expansive Sarasota Bay views, two generous terraces, and seamless indoor–outdoor flow create an ideal setting for sunsets, bay breezes, and relaxed coastal living. Set behind the gated Bay Isles entrance,

  Dianne Anderson COMPASS FLORIDA LLC

  3040 Grand Bay Blvd Unit 213, Longboat Key, FL 34228
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  /72

  $6,950 Per Month

  • 2 Beds
  • 2.5 Baths
  • 2,369 Sq Ft
  • Condo for Rent

  2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228

  Luxury Furnished Longboat Key Retreat with Private Beach Club Access & Golf Course Views. Remodeled 2BR Residence with Elevator, Designer Finishes & Resort-Style Living. 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

  Andrew Clark SECURE DOOR PROPERTY MANAGEMENT

  2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
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  /2

  $490,000 Sold Aug 01, 2025

  2045 Gulf of Mexico Dr Unit M1514, Longboat Key, FL 34228

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

  Last Sold Summary

  • 11% Below List Price
  • $528/SF
  • 51 Days On Market

  Current Estimated Value $507,250

  Last Listing Agent Michael Renick MANGROVE REALTY ASSOCIATES

  2045 Gulf of Mexico Dr Unit M1514, Longboat Key, FL 34228
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  /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

  • $430/SF
  • 268 Days On Market

  • Last Sold Price $320,000
  • Jun 27, 2023

  Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC
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  /52

  $1,450,000

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

  2425 Gulf of Mexico Dr Unit 1E, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. Welcome to this rarely available Seagate direct beachfront residence, where unmatched coastal living meets exceptional convenience. Step from your private terrace straight onto the sand, an experience that truly defines beachfront living. Perfectly situated across from the Publix Bay Isles Shopping Center and just moments from the world-famous

  Ryan Heers COLDWELL BANKER REALTY

  2425 Gulf of Mexico Dr Unit 1E, Longboat Key, FL 34228
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  /43

  $9,000 Per Month

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

  2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228

  Wake up to breathtaking Gulf of Mexico views from this beautifully remodeled 2-bedroom, 2-bath oceanfront residence at The Islander Club. Spanning approximately 1,233 sq ft, this turnkey condo offers sweeping panoramic views of the Gulf from the spacious living room and both bedrooms. Step inside to find a thoughtfully updated interior featuring modern finishes, a fully equipped kitchen with

  Michele Conn PREFERRED SHORE LLC

  2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228
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  /2

  $100,000 Sold Nov 24, 2025

  85 Twin Shores Blvd, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 800 Sq Ft
  • Built 1970

  Last Sold Summary

  • 8% Below List Price
  • $125/SF
  • 100 Days On Market

  Last Listing Agent Erica Smentowski KELLER WILLIAMS ON THE WATER S

  85 Twin Shores Blvd, Longboat Key, FL 34228
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  /43

  Est $1,312,539 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

  • 6% Below List Price
  • $1,195/SF
  • 61 Days On Market

  • Last Sold Price $1,400,000
  • Jun 10, 2024

  Last Listing Agent Lenore Treiman Michael Saunders
• 

  

  /19

  $150,000

  • Land
  • 1,306 Sq Ft
  • $5,000,000 per Acre

  3710 Gulf of Mexico Dr Unit D11, Longboat Key, FL 34228

  WELCOME TO PARADISE! Gulfshore of Longboat Key has it all - private, pristine sand beach, combined with the turquoise waters of the Gulf of Mexico, a marina on Sarasota Bay, large heated community pool, clubhouse with a commercial kitchen, a well-maintained campus and very reasonable HOA fees. Truly, Gulfshore is a remnant of Old Florida that is just six miles from the world-famous St. Armands

  Bill Shuttleworth EDGEWATER REAL ESTATE, INC

  3710 Gulf of Mexico Dr Unit D11, Longboat Key, FL 34228
• 

  

  /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
• 

  /2

  $17,500,000 Sold Nov 08, 2025

  6633 Gulf of Mexico Dr, Longboat Key, FL 34228

  • 7 Beds
  • 10 Baths
  • 9,622 Sq Ft
  • Built 2013

  Last Sold Summary

  • 12% Below List Price
  • $1,819/SF
  • 0 Days On Market

  Last Listing Agent Reid Murphy DEVELOPERS REALTY LBK, INC

  6633 Gulf of Mexico Dr, Longboat Key, FL 34228
• 

  

  /54

  Est $661,028 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

  • 17% Below List Price
  • $709/SF
  • 0 Days On Market

  • Last Sold Price $800,000
  • Feb 12, 2024

  Last Listing Agent Jens Pinkernell DOUGLAS ELLIMAN

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