11,341

Longboat Key, FL Homes

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  • /28

    $595,000

    • Land
    • 6,098 Sq Ft
    • $4,250,000 per Acre

    641 Broadway St, Longboat Key, FL 34228

    Discover the irresistible charm of historic Longbeach Village and seize a rare opportunity to build your dream island home on Longboat Key. Welcome to the lowest priced vacant single-family parcel available in the Village, an exceptional chance to design a custom residence just off the coast of Sarasota. This desired corner lot in the heart of the village offers flexible design possibilities,

    Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

    641 Broadway St, Longboat Key, FL 34228
  • /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
  • /2

    $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 $1,182,993

    Last Listing Agent Judy Mitchell PREMIER SOTHEBY'S INTERNATIONAL REALTY

    3111 Bayou Sound, Longboat Key, FL 34228
    • /2

      Not Listed For Sale

      3710 Gulf of Mexico Dr Unit G-6, Longboat Key, FL 34228

      • 1 Bed
      • 1 Bath
      • 643 Sq Ft
      • Built 1959
      3710 Gulf of Mexico Dr Unit G-6, Longboat Key, FL 34228

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC

  • /36

    $1,200,000

    • 2 Beds
    • 2 Baths
    • 1,398 Sq Ft

    4545 Gulf of Mexico Dr Unit 311, Longboat Key, FL 34228

    It doesn't get better than this ... sweeping gulf and beach views, the soothing sound of waves, and instant relaxation at The Castillian on Longboat Key. Residences here rarely become available, so all that's left to do is embrace the casual laid-back lifestyle. The condo's centerpiece is a beautifully renovated open kitchen featuring solid wood cabinetry, granite countertops, GE Monogram

    Janis Collier MICHAEL SAUNDERS & COMPANY

    4545 Gulf of Mexico Dr Unit 311, Longboat Key, FL 34228
  • /39

    $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
  • /2

    $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 $1,722,258

    Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY

    3519 Fair Oaks Ln, Longboat Key, FL 34228
    • /63

      Est $852,848

      Not Listed For Sale

      2213 Harbourside Dr Unit 303, Longboat Key, FL 34228

      • 3 Beds
      • 2.5 Baths
      • 2,224 Sq Ft
      • Built 1984
      2213 Harbourside Dr Unit 303, Longboat Key, FL 34228

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Maureen Horn MICHAEL SAUNDERS & COMPANY

  • /63

    $2,695,000

    $155K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 4,182 Sq Ft

    677 Lands End Dr, Longboat Key, FL 34228

    Experience the timeless appeal of a quintessential Florida island home, immersed in a lush tropical waterfront setting on Longboat Key. Elevated above a serene natural bayou off Sarasota Bay, this distinctive residence embodies the relaxed elegance of island living, with soaring ceilings, expansive wraparound decks, and pristine Gulf beaches just moments away.Launch a kayak from your private

    Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

    677 Lands End Dr, Longboat Key, FL 34228
  • /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, game room, pool table & cards room, BBQ

    4330 Falmouth Dr, Longboat Key, FL 34228
  • 603 Longboat Club Rd Unit 1103N, Longboat Key, FL 34228

    $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 $1,439,985

    Last Listing Agent Irma Scherer COMPASS FLORIDA LLC

    603 Longboat Club Rd Unit 1103N, Longboat Key, FL 34228
    • /48

      Est $1,162,771

      Not Listed For Sale

      3437 Winding Oaks Dr Unit 19, Longboat Key, FL 34228

      • 3 Beds
      • 3 Baths
      • 2,678 Sq Ft
      • Built 1988
      3437 Winding Oaks Dr Unit 19, Longboat Key, FL 34228

      Last Sold Summary

      • 200 Days On Market

      Last Listing Agent Toni Giliberti COLDWELL BANKER REALTY

  • /38

    $1,349,000

    $100K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,761 Sq Ft

    392 Firehouse Ln, Longboat Key, FL 34228

    Located on the coveted west side of Gulf of Mexico Drive, just steps from the beach, 392 Firehouse offers the relaxed coastal lifestyle Longboat Key is known for. Nestled on a quiet cul-de-sac surrounded exclusively by charming Key West-style homes, this beautifully updated residence blends timeless island architecture with thoughtful modern enhancements. Residents also enjoy the community pool

    Gina Ursini BRISTA REALTY LLC

    392 Firehouse Ln, Longboat Key, FL 34228
  • /44

    $4,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,106 Sq Ft
    • Condo for Rent

    3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228

    Tucked along the quiet edge of the key, where the water gently meets the shoreline and wildlife drifts by with the tide, this easily accessible residence offers something increasingly hard to find: effortless coastal living with the comfort and privacy of a home. Here, your day begins without elevators or long corridors. You simply pull up, step inside, and settle into a space designed for ease.

    Janette Schafer COLDWELL BANKER REALTY

    3330 Gulf of Mexico Dr Unit 104D, Longboat Key, FL 34228
  • /2

    $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 $1,783,946

    Last Listing Agent Brett Coady PINEYWOODS REALTY LLC

    540 Gulf Bay Rd, Longboat Key, FL 34228
    • /2

      Est $304,171

      Not Listed For Sale

      699 El Centro Unit 182, Longboat Key, FL 34228

      • 2 Beds
      • 2 Baths
      • 1,327 Sq Ft
      • Built 1969
      699 El Centro Unit 182, Longboat Key, FL 34228

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Geoff Scalera AUM FLORIDA REAL ESTATE LLC

  • /58

    $2,400,000

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 2,154 Sq Ft

    1591 Gulf of Mexico Dr Unit 512, Longboat Key, FL 34228

    Fractional Ownership. Fractional Ownership Opportunity at The St. Regis Longboat Key. Each purchase includes complimentary Resort Membership, valued at $125,000, along with the added benefit of no annual dues (a $14,000 value) and no minimum annual expenditure requirements. The Resort Membership can be enjoyed year-round, providing exceptional value and convenience to owners. For 2026, fee for

    Michael Moulton MICHAEL SAUNDERS & COMPANY

    1591 Gulf of Mexico Dr Unit 512, Longboat Key, FL 34228
  • /39

    $19,975 Per Month

    • 4 Beds
    • 3 Baths
    • 4,000 Sq Ft
    • House for Rent

    5801 Gulf of Mexico Dr, Longboat Key, FL 34228

    Welcome to your own Gulf-front retreat on Longboat Key!This expansive 4-bedroom, 3-bath home offers over 4,200 square feet of living space designed for relaxation, entertaining, and soaking in stunning beach views.Inside, you’ll find an open living and dining area with vaulted ceilings and multi-level walls of windows that bring in natural light and frame the Gulf.The

    5801 Gulf of Mexico Dr, Longboat Key, FL 34228
  • /2

    $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 $338,887

    Last Listing Agent Mairead Smialek COLDWELL BANKER REALTY

    4360 Chatham Dr Unit 204, Longboat Key, FL 34228
    • /66

      Est $533,090

      Not Listed For Sale

      583 Spanish Dr S Unit 129, Longboat Key, FL 34228

      • 2 Beds
      • 2 Baths
      • 1,399 Sq Ft
      • Built 1968
      583 Spanish Dr S Unit 129, Longboat Key, FL 34228

      Last Sold Summary

      • 223 Days On Market

      Last Listing Agent Kimberly Freiwald PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • /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
  • /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
  • /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 $1,206,238

    Last Listing Agent Mairead Smialek COLDWELL BANKER REALTY

    1445 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    • /2

      Not Listed For Sale

      3710 Gulf of Mexico Dr Unit G26, Longboat Key, FL 34228

      • 2 Beds
      • 2 Baths
      • 912 Sq Ft
      • Built 1980
      3710 Gulf of Mexico Dr Unit G26, Longboat Key, FL 34228

      Last Sold Summary

      Last Listing Agent Bill Shuttleworth EDGEWATER REAL ESTATE, INC

  • /44

    $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
  • /27

    $11,000 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. RARELY AVAILABLE FOR 2027 SEASON. LESING NOW FOR DECEMBER 2026 AND JANUARY TRHOUGH APRIL 30TH 2027. MINIMUM

    807 Bayport Way Unit LABS 807 Bayport Way - 58540307889, Longboat Key, FL 34228
  • /2

    $1,750,000

    Sold Oct 27, 2025

    6011 Emerald Harbor Dr, Longboat Key, FL 34228

    • 3 Beds
    • 2 Baths
    • 1,929 Sq Ft
    • Built 1973

    Last Sold Summary

    • 5% Below List Price
    • $907/SF
    • 0 Days On Market

    Current Estimated Value $1,922,365

    Last Listing Agent Judy Kepecz-Hays COLDWELL BANKER REALTY

    6011 Emerald Harbor Dr, Longboat Key, FL 34228
    • /2

      Est $1,301,465

      Not Listed For Sale

      603 Longboat Club Rd Unit 903N, Longboat Key, FL 34228

      • 2 Beds
      • 2 Baths
      • 1,458 Sq Ft
      • Built 1970
      603 Longboat Club Rd Unit 903N, Longboat Key, FL 34228

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  • /47

    $1,160,000

    • 3 Beds
    • 3.5 Baths
    • 2,369 Sq Ft

    3060 Grand Bay Blvd Unit 133, Longboat Key, FL 34228

    Virtually Staged. On the 3rd floor of Building One, this 3-bedroom, 3.5-bath residence opens to one of Longboat Key's signature views: the fairways and lagoons of the golf course in the foreground and Sarasota Bay stretching to the horizon beyond. A semi-private elevator landing opens to 2,369 square feet centered on a great room, where floor-to-ceiling sliders frame the water and open to a wide

    Matt Bohanon HOUSE MATCH

    3060 Grand Bay Blvd Unit 133, Longboat Key, FL 34228
  • /53

    $4,200 Per Month

    • 2 Beds
    • 2 Baths
    • 1,640 Sq Ft
    • Condo for Rent

    840 Bayport Way Unit 840, Longboat Key, FL 34228

    This stunningly appointed ground floor 2-bedroom 2 bath condo with lots of open living space is the ideal place to spend your summer vacation. Relax on screened lanai and enjoy the gentle breezes of this tropical oasis. Situated between Sarasota Bay and the Gulf of Mexico and surrounded by lush landscaping, you will truly find the private patio a great place to spend your afternoons. The

    Shirley Cuddy REALTY SERVICES INC

    840 Bayport Way Unit 840, Longboat Key, FL 34228
  • /2

    $1,700,000

    Sold Jun 24, 2026

    2410 Harbourside Dr Unit 131, Longboat Key, FL 34228

    • 3 Beds
    • 3.5 Baths
    • 3,825 Sq Ft
    • Built 1993

    Last Sold Summary

    • 8% Below List Price
    • $444/SF
    • 28 Days On Market

    Current Estimated Value $1,847,718

    Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

    2410 Harbourside Dr Unit 131, Longboat Key, FL 34228
    • /2

      Est $495,441

      Not Listed For Sale

      4500 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228

      • 2 Beds
      • 2 Baths
      • 1,325 Sq Ft
      • Built 1975
      4500 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228

      Last Sold Summary

      • 125 Days On Market

      Last Listing Agent Debby McCaig COLDWELL BANKER REALTY

  • /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
  • /54

    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Seasonal/short term 2/2 condo rental with full water view on Longboat Key.

    3240 Gulf of Mexico Dr, Longboat Key, FL 34228

    Seasonal / Short-Term Rental on Longboat KeyVacation in one of the nation’s most celebrated coastal destinations, where a leading national travel magazine ranked Longboat Key among the Top 5 Best Islands in the United States. Experience the beauty firsthand while enjoying breathtaking water views from nearly every room of this stunning condominium at Portobello. This beautifully renovated and

    3240 Gulf of Mexico Dr, Longboat Key, FL 34228
  • /2

    $2,208,000

    Sold May 26, 2026

    775 Longboat Club Rd Unit 408, Longboat Key, FL 34228

    • 3 Beds
    • 3 Baths
    • 2,122 Sq Ft
    • Built 1984

    Last Sold Summary

    • 11% Above List Price
    • $1,041/SF
    • 7 Days On Market

    Current Estimated Value $2,112,793

    Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

    775 Longboat Club Rd Unit 408, Longboat Key, FL 34228
    • /2

      Est $542,588

      Not Listed For Sale

      575 Sutton Place Unit T-4, Longboat Key, FL 34228

      • 3 Beds
      • 2.5 Baths
      • 1,450 Sq Ft
      • Built 1972
      575 Sutton Place Unit T-4, Longboat Key, FL 34228

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Michael Yawitz MICHAEL SAUNDERS & COMPANY

  • /62

    $6,950,000

    New Construction Open House 8/23
    • 4 Beds
    • 6 Baths
    • 4,274 Sq Ft

    711 Old Compass Rd, Longboat Key, FL 34228

    Timeless architecture, uncompromising craftsmanship, and spectacular waterfront living converge in this newly completed West Indies-inspired residence in the coveted neighborhood of Emerald Harbor on Longboat Key. This gorgeous home offers expansive indoor-outdoor living with walls of glass that open to covered porches and balconies off of every room, framing tranquil views of the gorgeous pool

    JoDene Moneuse MICHAEL SAUNDERS & COMPANY

    711 Old Compass Rd, Longboat Key, FL 34228
  • /46

    $5,500 Per Month

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

    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

    A little slice of Gulf-front heaven. Seasonal rental only, available July 15 through December 31, 2026! 60 Day Minimum Lease, not available Jan 1, 2027-March 31, 2027. Fully remodeled and impeccably furnished with Gulf views on Longboat Key, this top-floor 2-bedroom, 2-bath residence offers breathtaking views of the beach and Gulf of Mexico. The clear Caribbean-blue waters and white sand beaches

    Scott Nold TNG PROPERTY MANAGEMENT

    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
  • /2

    $400,000

    Sold Aug 02, 2026

    4500 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft
    • Built 1975

    Last Sold Summary

    • 5% Below List Price
    • $302/SF
    • 0 Days On Market

    Last Listing Agent Debby McCaig COLDWELL BANKER REALTY

    4500 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    • /2

      Est $8,516,605

      Not Listed For Sale

      1581 Gulf of Mexico Dr Unit 308, Longboat Key, FL 34228

      • 4 Beds
      • 4.5 Baths
      • 4,017 Sq Ft
      • Built 2024
      1581 Gulf of Mexico Dr Unit 308, Longboat Key, FL 34228

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Charles Buky COLDWELL BANKER REALTY

Showing Results 201 - 240, Page 6 of 18

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