11,346

Longboat Key, FL Homes

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  • /46

    $499,000

    • 2 Beds
    • 2 Baths
    • 1,337 Sq Ft

    578 Spanish Dr S, Longboat Key, FL 34228

    Welcome to 578 Spanish Drive S, a completely renovated 2 bedroom, 2 bathroom villa in Spanish Main Yacht Club on Longboat Key. Renovated completely with thoughtful attention to detail, this move-in ready residence showcases high-quality modern finishes while providing access & amenities to one of Longboat Key's established waterfront communities with a deepwater marina and deeded beach access.

    Ali Marks LOYD ROBBINS & CO. LLC

    578 Spanish Dr S, Longboat Key, FL 34228
  • /34

    $3,042

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,388 Sq Ft
    • Condo for Rent

    1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228

    The advertised rate of $3,042/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 8, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228
  • /2

    $1,150,000

    Sold Mar 31, 2026

    2425 Gulf of Mexico Dr Unit 7D, Longboat Key, FL 34228

    • 2 Beds
    • 2 Baths
    • 1,470 Sq Ft
    • Built 1973

    Last Sold Summary

    • 32% Below List Price
    • $782/SF
    • 102 Days On Market

    Current Estimated Value $1,236,705

    Last Listing Agent Matt Bohanon HOUSE MATCH

    2425 Gulf of Mexico Dr Unit 7D, Longboat Key, FL 34228
    • /42

      Est $355,719

      Not Listed For Sale

      102 Twin Shores Blvd, Longboat Key, FL 34228

      • 2 Beds
      • 2 Baths
      • 809 Sq Ft
      • Built 1950
      102 Twin Shores Blvd, Longboat Key, FL 34228

      Last Sold Summary

      • 90 Days On Market

      Last Listing Agent Allison Menke BRIGHT REALTY

  • /36

    $499,900

    • 2 Beds
    • 2 Baths
    • 1,072 Sq Ft

    4340 Falmouth Dr Unit 104, Longboat Key, FL 34228

    Welcome to your slice of paradise on beautiful Longboat Key. Priced to sell and offered fully furnished, this beautifully maintained two-bedroom condominium is truly move-in ready. Combining breathtaking Sarasota Bay views with exclusive deeded beach access, this exceptional residence offers the perfect blend of waterfront serenity, resort-style amenities, and effortless coastal living. Wake each

    Melissa Sherk PREFERRED SHORE LLC

    4340 Falmouth Dr Unit 104, Longboat Key, FL 34228
  • /38

    $7,000 Per Month

    • 3 Beds
    • 2 Baths
    • 2,091 Sq Ft
    • House for Rent

    3210 Bayou Sound, Longboat Key, FL 34228

    Experience the best of Longboat Key living in this beautifully updated Bay Isles pool home, offered turnkey furnished FOR LEASE and available for both short-term and long-term reservations. This furnished coastal retreat features an open floor plan with vaulted ceilings, 2 bedrooms plus an office, updated bathrooms, a spacious kitchen with premium appliances, and multiple indoor-outdoor living

    Richard Ivan WAGNER REALTY

    3210 Bayou Sound, Longboat Key, FL 34228
  • /2

    $525,000

    Sold May 14, 2026

    2039 Gulf of Mexico Dr Unit G3108, Longboat Key, FL 34228

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

    Last Sold Summary

    • 8% Below List Price
    • $563/SF
    • 28 Days On Market

    Current Estimated Value $525,672

    Last Listing Agent Michael Renick MANGROVE REALTY ASSOCIATES

    2039 Gulf of Mexico Dr Unit G3108, Longboat Key, FL 34228
    • /80

      Est $2,949,902

      Not Listed For Sale

      1241 Gulf of Mexico Dr Unit 707, Longboat Key, FL 34228

      • 2 Beds
      • 4.5 Baths
      • 2,965 Sq Ft
      • Built 1996
      1241 Gulf of Mexico Dr Unit 707, Longboat Key, FL 34228

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Michael Moulton MICHAEL SAUNDERS & COMPANY

  • /36

    $449,000

    $16K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 933 Sq Ft

    1935 Gulf of Mexico Dr Unit G7304, Longboat Key, FL 34228

    Experience the best of coastal living in this beautifully maintained 2-bedroom, 1-bathroom condominium, perfectly situated on the third floor ofthe desirable Seaside community on Longboat Key. Set within a secure, 24-hour guard-gated enclave, this charming residence offers both privacyand peace of mind. Step inside to discover a light and airy interior that was tastefully repainted in

    Alie Espinoza EATON REALTY

    1935 Gulf of Mexico Dr Unit G7304, Longboat Key, FL 34228
  • /49

    $8,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,143 Sq Ft
    • Luxury Seasonal or Annual Rental in the Prestigious Grand Bay Community – Longboat Key

    3040 Grand Bay Blvd, Longboat Key, FL 34228

    Experience unparalleled luxury and breathtaking views from this stunning 9th-floor condominium at Grand Bay. From sunrise to sunset, enjoy panoramic vistas from your private wraparound balcony or through the floor-to-ceiling sliding glass doors that frame the living room. Designed for both relaxation and sophistication, this residence offers the elegance of a luxury waterfront home with the

    3040 Grand Bay Blvd, Longboat Key, FL 34228
  • /2

    $700,000

    Sold Jun 12, 2026

    350 Gulf of Mexico Dr Unit 234, Longboat Key, FL 34228

    • 3 Beds
    • 3.5 Baths
    • 2,513 Sq Ft
    • Built 1992

    Last Sold Summary

    • 39% Below List Price
    • $279/SF
    • 117 Days On Market

    Current Estimated Value $1,015,819

    Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY

    350 Gulf of Mexico Dr Unit 234, Longboat Key, FL 34228
    • /2

      Est $1,067,559

      Not Listed For Sale

      4401 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228

      • 2 Beds
      • 2 Baths
      • 1,314 Sq Ft
      • Built 1972
      4401 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228

      Last Sold Summary

      • 425 Days On Market

      Last Listing Agent Thomas Washburn BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

  • /64

    $610,000

    $15K PRICE DROP
    • 1 Bed
    • 1.5 Baths
    • 1,094 Sq Ft

    2055 Gulf of Mexico Dr Unit G2213, Longboat Key, FL 34228

    NO expense spared and everything replaced! Gulf and greenbelt views await from your top floor Seaplace condo! Completely remodeled. This gorgeous gulf-facing oversized one bedroom, 1.5 bath end unit with vaulted ceilings features 1,094 square feet of living space and spacious lanai adding an additional 112 square feet with custom 95% UV blocking solar shades. The convenient second floor location

    Derek Eisenberg CONTINENTAL REAL ESTATE GROUP

    2055 Gulf of Mexico Dr Unit G2213, Longboat Key, FL 34228
  • /40

    $5,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,411 Sq Ft
    • Condo for Rent

    4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228

    Longboat Key vacation rental, rarely available Tiffany Plaza direct Gulf Front condo with amazing views! As you enter your gaze will be drawn to the turquoise waters of the Gulf of Mexico and the serene beach frontage. This lovely home offers 2 beds & 2 baths, plus a bonus office space with a twin Murphy bed! The kitchen and the baths have been updated, the primary bedroom offers a King bed, walk

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
  • /2

    $1,766,000

    Sold Feb 04, 2026

    3060 Grand Bay Blvd Unit 175, Longboat Key, FL 34228

    • 3 Beds
    • 2.5 Baths
    • 2,143 Sq Ft
    • Built 1994

    Last Sold Summary

    • 9% Below List Price
    • $824/SF
    • 86 Days On Market

    Current Estimated Value $1,757,419

    Last Listing Agent Judy Mitchell PREMIER SOTHEBY'S INTERNATIONAL REALTY

    3060 Grand Bay Blvd Unit 175, Longboat Key, FL 34228
    • /2

      Est $360,970

      Not Listed For Sale

      754 Spanish Dr S Unit 754, Longboat Key, FL 34228

      • 2 Beds
      • 2 Baths
      • 1,245 Sq Ft
      • Built 1968
      754 Spanish Dr S Unit 754, Longboat Key, FL 34228

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Geoff Scalera AUM FLORIDA REAL ESTATE LLC

  • /43

    $589,000

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    508 Forest Way, Longboat Key, FL 34228

    There is a certain ease to life on Longboat Key, where mornings can begin with a walk to the beach, afternoons unfold by the pool or on the tennis court, and dinner beside the water is never far from home. Set within Cedars East at Cedars Tennis Resort & Club, this beautifully maintained three-level townhome offers a refined way to experience one of Florida’s most desirable barrier-island

    Kevin Hanley KELLER WILLIAMS ISLAND LIFE REAL ESTATE

    508 Forest Way, Longboat Key, FL 34228
  • /26

    $2,500 Per Month

    • 1 Bed
    • 1.5 Baths
    • 761 Sq Ft
    • Beach Harbor Club Beauty

    3802 Gulf of Mexico Dr, Longboat Key, FL 34228

    AVAILABLE FOR ANNUAL OR 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 a bright

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

    $475,000

    Sold Mar 31, 2026

    6750 Gulf of Mexico Dr Unit 154, Longboat Key, FL 34228

    • 2 Beds
    • 2 Baths
    • 1,441 Sq Ft
    • Built 1970

    Last Sold Summary

    • 17% Below List Price
    • $330/SF
    • 66 Days On Market

    Current Estimated Value $474,177

    Last Listing Agent Amy Jones COASTAL KEY REALTY LLC

    6750 Gulf of Mexico Dr Unit 154, Longboat Key, FL 34228
    • /2

      Not Listed For Sale

      29 Main Street Dr, Longboat Key, FL 34228

      • 2 Beds
      • 2 Baths
      • 924 Sq Ft
      • Built 2019
      29 Main Street Dr, Longboat Key, FL 34228

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Erica Smentowski KELLER WILLIAMS ON THE WATER S

  • /78

    $5,995,000

    • 4 Beds
    • 4 Baths
    • 2,721 Sq Ft

    7143 La Lenaire Dr, Longboat Key, FL 34228

    Private island living on Jewfish Key, one of eight homes, accessible by boat only. This rare offering presents a lifestyle few will ever experience: a secluded island sanctuary surrounded by the turquoise waters of Longboat Pass and the Gulf Coast’s natural beauty. An address like this comes up for sale about once a generation. 7143 La Lenaire is on the market for the first time in more than two

    Michelle Ward COMPASS FLORIDA LLC

    7143 La Lenaire Dr, Longboat Key, FL 34228
  • /44

    $14,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,268 Sq Ft
    • House for Rent

    531 Birdie Ln, Longboat Key, FL 34228

    Annual Rental – Stunning Waterfront Home in Country Club Shores on Longboat Key. Experience the best of waterfront living in this beautiful 4-bedroom, 3.5-bathroom home located in the sought-after Country Club Shores community on Longboat Key. This spacious and elegant residence offers breathtaking canal views, luxurious amenities, and direct boating access and boat lift. This exceptional home

    Karie Gorgone WAGNER REALTY

    531 Birdie Ln, Longboat Key, FL 34228
  • /2

    $337,500

    Sold Mar 26, 2026

    730 Spanish Dr S Unit 99, Longboat Key, FL 34228

    • 2 Beds
    • 2 Baths
    • 1,375 Sq Ft
    • Built 1969

    Last Sold Summary

    • 16% Below List Price
    • $245/SF
    • 284 Days On Market

    Current Estimated Value $340,637

    Last Listing Agent Adrienne Scott MICHAEL SAUNDERS & COMPANY

    730 Spanish Dr S Unit 99, Longboat Key, FL 34228
    • /2

      Est $61,072

      Not Listed For Sale

      408 Gulf of Mexico Dr Unit 1222, Longboat Key, FL 34228

      • Studio
      • Built 1987
      408 Gulf of Mexico Dr Unit 1222, Longboat Key, FL 34228

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

  • /59

    $2,900,000

    • 3 Beds
    • 3.5 Baths
    • 3,045 Sq Ft

    524 Hornblower Ln, Longboat Key, FL 34228

    Tucked along one of the most sought-after canals in Country Club Shores, 524 Hornblower Lane is a waterfront residence that fully embodies the Longboat Key lifestyle, where boating access, beach proximity, and refined coastal living intersect with intention. Set on a 0.28-acre canal-front homesite with 107 feet of water frontage, the property offers what experienced boaters immediately recognize

    Joel Schemmel DOUGLAS ELLIMAN

    524 Hornblower Ln, Longboat Key, FL 34228
  • /12

    $7,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,305 Sq Ft
    • House for Rent

    537 Outrigger Ln, Longboat Key, FL 34228

    Welcome boating enthusiasts to this exceptional waterfront residence located in the highly desirable Country Club Shores community on Longboat Key. Situated on a deep-water canal with direct access to the Gulf of America, this beautifully updated two-bedroom, two-bath home with a den offers the ultimate island lifestyle for boaters and beach lovers alike. The property features a brand-new

    537 Outrigger Ln, Longboat Key, FL 34228
  • /2

    $1,499,000

    Sold Jul 07, 2026

    1445 Gulf of Mexico Dr Unit 501, Longboat Key, FL 34228

    • 3 Beds
    • 3 Baths
    • 2,642 Sq Ft
    • Built 1982

    Last Sold Summary

    • $567/SF
    • 11 Days On Market

    Current Estimated Value $1,851,575

    Last Listing Agent Ian Addy, PA MICHAEL SAUNDERS & COMPANY

    1445 Gulf of Mexico Dr Unit 501, Longboat Key, FL 34228
    • /2

      Not Listed For Sale

      2600 Harbourside Dr Unit O-05, Longboat Key, FL 34228

      • Built 1985
      2600 Harbourside Dr Unit O-05, Longboat Key, FL 34228

      Last Sold Summary

      • 66 Days On Market

      Last Listing Agent Jennifer Wilson LBRE LLC

  • /62

    $775,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,456 Sq Ft

    803 Bayport Way Unit 803, Longboat Key, FL 34228

    Under contract-accepting backup offers. Welcome to the true tropical oasis of Bayport Beach & Tennis Club, a Longboat Key Gulf to Bay community. Bayport was designed by Tim Siebert, one of the founding architects of the renowned Sarasota School of Architecture and is recognized for its award-winning, timeless design. Bayport offers 27 lushly landscaped acres with 1,200 feet of private beach. This

    Alexis Smith-Frady COMPASS FLORIDA LLC

    803 Bayport Way Unit 803, Longboat Key, FL 34228
  • /39

    $10,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,576 Sq Ft
    • Condo for Rent

    4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228

    **BEST WATER VIEWS - Enjoy a warm Winter Escape at this expansive 3 bed 2 bath LONGBOAT KEY PENTHOUSE BEACHFRONT CONDO!** **AVAILABLE to lease DECEMBER 2026 and APRIL 2027** Welcome to your dream winter retreat, where you can bask in the beauty of the Gulf of Mexico right from your living room. This pristine, 2-bedrooms +Den/Office with Sleeper Sofa and 2-bath penthouse condo is located directly

    Norma Mladineo COLDWELL BANKER REALTY

    4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
  • /2

    $500,000

    Sold May 01, 2026

    620 Companion Way, Longboat Key, FL 34228

    • Land
    • 8,276 Sq Ft
    • $2,631,579 per Acre

    Last Sold Summary

    • 15% Below List Price
    • 68 Days On Market

    Current Estimated Value $497,288

    Last Listing Agent JoDene Moneuse MICHAEL SAUNDERS & COMPANY

    620 Companion Way, Longboat Key, FL 34228
    • /2

      Est $996,197

      Not Listed For Sale

      230 Sands Point Rd Unit 3501, Longboat Key, FL 34228

      • 1 Bed
      • 1 Bath
      • 750 Sq Ft
      • Built 1982
      230 Sands Point Rd Unit 3501, Longboat Key, FL 34228

      Last Sold Summary

      • 58 Days On Market

      Last Listing Agent Judy Kepecz-Hays COLDWELL BANKER REALTY

  • /19

    $375,000

    $50K PRICE DROP

    2600 Harbourside Dr Unit L-03, Longboat Key, FL 34228

    Ask an L-dock boater, they will tell you its the best dock in the marina. Slip is near the seawall with easy in/out access. A 68 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota

    Jennifer Wilson LBRE LLC

    2600 Harbourside Dr Unit L-03, Longboat Key, FL 34228
  • /35

    $9,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,140 Sq Ft
    • Luxury Annual Rental with Resort-Style Pool on Longboat Key

    691 Russell St, Longboat Key, FL 34228

    Experience luxury coastal living in this completely renovated annual rental on the desirable north end of Longboat Key. Situated on an oversized double lot just minutes from the pristine Gulf beaches, this exceptional pool home offers the perfect blend of style, comfort, and convenience.Thoughtfully redesigned from top to bottom, the home features a bright, open-concept floor plan with

    691 Russell St, Longboat Key, FL 34228
  • /2

    $470,000

    Sold Jan 16, 2026

    3155 Gulf of Mexico Dr Unit 257, Longboat Key, FL 34228

    • 1 Bed
    • 1 Bath
    • 416 Sq Ft
    • Built 1960

    Last Sold Summary

    • $1,130/SF
    • 9 Days On Market

    Current Estimated Value $484,747

    Last Listing Agent Ryndie Brusco MICHAEL SAUNDERS & COMPANY

    3155 Gulf of Mexico Dr Unit 257, Longboat Key, FL 34228
    • /2

      Est $2,707,098

      Not Listed For Sale

      2185 Gulf of Mexico Dr Unit 245, Longboat Key, FL 34228

      • 3 Beds
      • 2 Baths
      • 2,590 Sq Ft
      • Built 1996
      2185 Gulf of Mexico Dr Unit 245, Longboat Key, FL 34228

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Candy Swick CANDY SWICK & COMPANY

  • /65

    $649,900

    $25K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,376 Sq Ft

    4430 Exeter Dr Unit 108, Longboat Key, FL 34228

    Stunning Sarasota Bay Views from a Move-In-Ready First-Floor Spacious Corner Unit!Wake up to breathtaking, unobstructed Sarasota Bay vistas in this turnkey first-floor corner residence, designed with upscale Tommy Bahama–inspired flair. This exceptional home blends luxury island living with immediate rental potential, offering panoramic water views from both the primary and guest bedrooms,

    Malihe Karimi MICHAEL SAUNDERS & COMPANY

    4430 Exeter Dr Unit 108, Longboat Key, FL 34228
  • /34

    $3,500 Per Month

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

    2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228

    Welcome to 2012 Harbourside Dr, a beautifully located home within the Bay Isles community on Longboat Key. This spacious residence provides access to the best of Florida’s coastal lifestyle, including a nearby marina, private golf course, pool, and spa. Enjoy the serenity of this gated community, which offers privacy and proximity to the scenic Sarasota Bay. Just a short drive from the cultural

    Alex Larchenko KELLER WILLIAMS ON THE WATER S

    2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
  • /2

    $515,000

    Sold Jun 03, 2026

    1930 Harbourside Dr Unit 145, Longboat Key, FL 34228

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

    Last Sold Summary

    • 14% Below List Price
    • $406/SF
    • 23 Days On Market

    Current Estimated Value $550,743

    Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

    1930 Harbourside Dr Unit 145, Longboat Key, FL 34228
    • /2

      Est $713,944

      Not Listed For Sale

      4540 Gulf of Mexico Dr Unit PH1, Longboat Key, FL 34228

      • 2 Beds
      • 2 Baths
      • 1,561 Sq Ft
      • Built 1975
      4540 Gulf of Mexico Dr Unit PH1, Longboat Key, FL 34228

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Marcela Terrell COLDWELL BANKER REALTY

Showing Results 161 - 200, Page 5 of 18

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