11,341

Longboat Key, FL Homes

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  • /68

    $950,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,172 Sq Ft

    1045 Gulf of Mexico Dr Unit 301, Longboat Key, FL 34228

    Coastal living at its finest and the perfect beach front retreat. This third floor corner residence is ready for your creative spirit. It offers views of the beach, the sparkling Gulf of Mexico, and breath taking sunsets year round. The new impact windows and sliding glass doors where installed in 2020 and the new HVAC system was replaced in March of 2026. This property is in very good condition

    Maggie Hicks COLDWELL BANKER REALTY

    1045 Gulf of Mexico Dr Unit 301, Longboat Key, FL 34228
  • /32

    $3,500 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,626 Sq Ft
    • Townhouse for Rent

    1928 Harbourside Dr Unit 1402, Longboat Key, FL 34228

    Experience furnished island living in this turnkey, two-level Fairway Bay townhome offering 2 bedrooms, 2 full bathrooms, 1 half bathroom and 1,626 square feet of thoughtfully arranged living space. The open living and dining area is enhanced by cathedral and vaulted ceilings and offers views of the tropical landscaping and community pool. A split-bedroom layout provides separation between the

    Alex Larchenko KELLER WILLIAMS ON THE WATER S

    1928 Harbourside Dr Unit 1402, Longboat Key, FL 34228
  • /2

    $1,550,000

    Sold Aug 18, 2025

    2450 Harbourside Dr Unit 233, Longboat Key, FL 34228

    • 3 Beds
    • 2.5 Baths
    • 3,080 Sq Ft
    • Built 1990

    Last Sold Summary

    • 11% Below List Price
    • $503/SF
    • 68 Days On Market

    Current Estimated Value $1,584,693

    Last Listing Agent Linda Weber COLDWELL BANKER REALTY

    2450 Harbourside Dr Unit 233, Longboat Key, FL 34228
    • /58

      Est $1,934,221

      Not Listed For Sale

      699 Penfield St, Longboat Key, FL 34228

      • 2 Beds
      • 3 Baths
      • 2,536 Sq Ft
      • Built 2009
      699 Penfield St, Longboat Key, FL 34228

      Last Sold Summary

      • 121 Days On Market

      Last Listing Agent Cathy Meldahl, PA MICHAEL SAUNDERS & COMPANY

  • /12

    $259,000

    Pending
    • 1 Bed
    • 1 Bath
    • 630 Sq Ft

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

    DIRECT WATERFRONT OPPORTUNITY IN LONGBOAT KEY! Here's your rare chance to own a waterfront property with direct access to the Intercoastal Waterway! Perfectly located for vacation rentals, this canal-front 1-bedroom, 1-bathroom end unit offers incredible potential for income, especially with high demand bookings from January to April. This property boasts 21 feet of water frontage and a newly

    Filitsa Sterner NIZZ REALTY INC

    701 Saint Judes Dr S Unit 3, Longboat Key, FL 34228
  • /25

    $5,700 Per Month

    • 2 Beds
    • 2 Baths
    • 1,160 Sq Ft
    • Condo for Rent

    540 Neptune Ave Unit 7, Longboat Key, FL 34228

    ****Enchanting, Iconic...Gulf Key****~Discover Relaxation and Island Charm Just Steps from the Beach~ Unwind at Gulf Key Welcome to Gulf Key, a truly iconic villa community where the spirit of “old Florida” meets modern comfort. This immaculate, newly renovated 2-bedroom, 2-bath villa is perfectly situated just a 5-minute walk from the beach, making it an ideal destination for anyone seeking

    Pamala Casey CASEY REALTY CORPORATION

    540 Neptune Ave Unit 7, Longboat Key, FL 34228
  • /2

    $900,000

    Sold Nov 14, 2025

    3465 Winding Oaks Dr Unit 33, Longboat Key, FL 34228

    • 3 Beds
    • 3 Baths
    • 2,608 Sq Ft
    • Built 1988

    Last Sold Summary

    • 1% Above List Price
    • $345/SF
    • 2 Days On Market

    Current Estimated Value $955,227

    Last Listing Agent Julie Klick MICHAEL SAUNDERS & COMPANY

    3465 Winding Oaks Dr Unit 33, Longboat Key, FL 34228
    • /64

      Est $822,579

      Not Listed For Sale

      641 Saint Judes Dr, Longboat Key, FL 34228

      • 3 Beds
      • 3 Baths
      • 1,556 Sq Ft
      • Built 1960
      641 Saint Judes Dr, Longboat Key, FL 34228

      Last Sold Summary

      • 128 Days On Market

      Last Listing Agent Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

  • /41

    $2,195,000

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

    775 Longboat Club Rd Unit 808, Longboat Key, FL 34228

    Behind the gates of the Longboat Key Club, this exceptional residence at The Beaches captures sweeping, unobstructed views of the Gulf of Mexico and its pristine shoreline, where vivid sunsets paint the horizon each evening. Perched on the eighth floor, this coveted Star floor plan is ideally positioned as a spacious end residence, offering 2,122 square feet of thoughtfully designed living space

    Lenore Treiman MICHAEL SAUNDERS & COMPANY

    775 Longboat Club Rd Unit 808, Longboat Key, FL 34228
  • /100

    $65,000 Per Month

    • 4 Beds
    • 4.5 Baths
    • 5,334 Sq Ft
    • Condo for Rent

    1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228

    Imagine taking in this view from your private balcony pool! An exceptionally rare opportunity to lease one of the most exclusive waterfront residences ever offered on Florida’s Gulf Coast. Positioned within the iconic St. Regis Residences on Longboat Key, this extraordinary four-bedroom, four-and-a-half-bath condominium redefines annual luxury living with an unrivaled level of privacy,

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228
  • /2

    $1,150,000

    Sold Jan 08, 2026

    4241 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

    • 3 Beds
    • 2.5 Baths
    • 1,660 Sq Ft
    • Built 1980

    Last Sold Summary

    • 15% Below List Price
    • $693/SF
    • 117 Days On Market

    Current Estimated Value $1,175,582

    Last Listing Agent Ian Greenberg BRISTA REALTY LLC

    4241 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    • /74

      Est $3,462,157

      Not Listed For Sale

      551 Broadway St, Longboat Key, FL 34228

      • 4 Beds
      • 4.5 Baths
      • 3,738 Sq Ft
      • Built 2024
      551 Broadway St, Longboat Key, FL 34228

      Last Sold Summary

      • 486 Days On Market

      Last Listing Agent Greg Bayer BEACH HOUSE REAL ESTATE LLC

  • /29

    $1,395,000

    • 3 Beds
    • 2 Baths
    • 1,941 Sq Ft

    100 Sands Point Rd Unit 323, Longboat Key, FL 34228

    Sands Point, a sought-after beachfront community within the gates of the Longboat Key Club, set on the gorgeous southern tip of Longboat Key. This newly remodeled 3BR/2BA, split plane with a large open living space to relax or entertain family and friends. The kitchen has been remarkably redone, featuring a breakfast bar, dining area, and custom solid surface countertops to complement the

    Marisa Marino BRIGHT REALTY

    100 Sands Point Rd Unit 323, Longboat Key, FL 34228
  • /75

    $7,850 Per Month

    • 3 Beds
    • 3 Baths
    • 2,250 Sq Ft
    • Condo for Rent

    3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228

    LOCATION AT IT'S BEST!!!!! LUXURY RENTAL in Paradise on LONGBOAT KEY at GRAND BAY. This STUNNING 7th floor condominium has both sweeping WATER VIEWS of SARASOTA BAY and of the spectacular SUNSETS ON THE GULF of MEXICO. Open for a three month or longer stay July through November. Like NEW, this beautifully designed and remodeled this three bedroom luxury residence has recently completed a major

    Patrice Ivan WAGNER REALTY

    3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
  • /2

    $449,000

    Sold Jun 05, 2026

    1975 Gulf of Mexico Dr Unit G4308, Longboat Key, FL 34228

    • 2 Beds
    • 2 Baths
    • 1,068 Sq Ft
    • Built 1977

    Last Sold Summary

    • 6% Below List Price
    • $420/SF
    • 211 Days On Market

    Current Estimated Value $467,940

    Last Listing Agent Michael Renick MANGROVE REALTY ASSOCIATES

    1975 Gulf of Mexico Dr Unit G4308, Longboat Key, FL 34228
    • /2

      Est $648,920

      Not Listed For Sale

      651 Fox St, Longboat Key, FL 34228

      • 3 Beds
      • 2 Baths
      • 1,416 Sq Ft
      • Built 1954
      651 Fox St, Longboat Key, FL 34228

      Last Sold Summary

      • 110 Days On Market

      Last Listing Agent JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  • /47

    $1,900,000

    • Land
    • 16,117 Sq Ft
    • $5,135,135 per Acre

    6549 Gulf of Mexico Dr, Longboat Key, FL 34228

    Flanked by multi-million-dollar homes, uniquely situated on the West side of Gulf of Mexico Dr with no busy street between you and the beach! Lot is cleared and ready with utilities at the lot. Build your dream home on this large lot (16,000 sq ft) just steps from the sugar sand beach on beautiful Longboat Key on the Gulf. This lot has the added bonus of backing up to Gulfside Road with a very

    Holly Switow PREMIER SOTHEBY'S INTERNATIONAL REALTY

    6549 Gulf of Mexico Dr, 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
  • /2

    $879,000

    Sold Apr 15, 2026

    2045 Gulf of Mexico Dr Unit M1309, Longboat Key, FL 34228

    • 2 Beds
    • 2 Baths
    • 1,265 Sq Ft
    • Built 1974

    Last Sold Summary

    • 2% Below List Price
    • $695/SF
    • 2 Days On Market

    Current Estimated Value $870,918

    Last Listing Agent Michael Renick MANGROVE REALTY ASSOCIATES

    2045 Gulf of Mexico Dr Unit M1309, Longboat Key, FL 34228
    • /2

      Est $7,121,881

      Not Listed For Sale

      500 Harbor Point Rd, Longboat Key, FL 34228

      • 5 Beds
      • 6.5 Baths
      • 6,556 Sq Ft
      • Built 2008
      500 Harbor Point Rd, Longboat Key, FL 34228

      Last Sold Summary

      • 98 Days On Market

      Last Listing Agent Steve and Janet Walter MICHAEL SAUNDERS & COMPANY

  • /80

    $7,900,000

    $800K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,485 Sq Ft

    560 Harbor Cove Cir, Longboat Key, FL 34228

    An exceedingly rare offering within the exclusive Bay Harbour enclave of Bay Isles on Longboat Key, this extraordinary peninsula estate delivers exceptional privacy, dramatic Sarasota Bay views, and direct boating access to both the Intracoastal Waterway and the Gulf of Mexico. Positioned at the end of a quiet cul-de-sac on a three-sided waterfront peninsula, the property features two private

    Rachel Tritschler RE/MAX ALLIANCE GROUP

    560 Harbor Cove Cir, Longboat Key, FL 34228
  • /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
  • /2

    $435,000

    Sold Dec 19, 2025

    1965 Gulf of Mexico Dr Unit G5304, Longboat Key, FL 34228

    • 2 Beds
    • 1 Bath
    • 933 Sq Ft
    • Built 1977

    Last Sold Summary

    • 13% Below List Price
    • $466/SF
    • 112 Days On Market

    Current Estimated Value $467,747

    Last Listing Agent Michael Renick MANGROVE REALTY ASSOCIATES

    1965 Gulf of Mexico Dr Unit G5304, Longboat Key, FL 34228
    • /2

      Est $2,884,613

      Not Listed For Sale

      3314 Bayou Rd, Longboat Key, FL 34228

      • 4 Beds
      • 4.5 Baths
      • 4,004 Sq Ft
      • Built 2008
      3314 Bayou Rd, Longboat Key, FL 34228

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Debra Pitell-Hauge MICHAEL SAUNDERS & COMPANY

  • /48

    $995,000

    Under Contract
    • 3 Beds
    • 3.5 Baths
    • 2,143 Sq Ft

    3030 Grand Bay Blvd Unit 312, Longboat Key, FL 34228

    Under contract-accepting backup offers. Located in the Grand Bay community on Longboat Key, this spacious 3BR residence offers stunning views and desirable extras, including 2 conveniently located parking spaces. The pet friendly community allows up to 2 large dogs. The home features luxury vinyl flooring and neutral tones throughout, with floor-to-ceiling windows and plantation shutters that let

    Bruce Myer COLDWELL BANKER REALTY

    3030 Grand Bay Blvd Unit 312, Longboat Key, FL 34228
  • /28

    $7,000 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
  • /2

    $1,500,000

    Sold Jul 09, 2026

    3010 Grand Bay Blvd Unit 482, Longboat Key, FL 34228

    • 3 Beds
    • 3.5 Baths
    • 2,250 Sq Ft
    • Built 1999

    Last Sold Summary

    • 16% Below List Price
    • $667/SF
    • 323 Days On Market

    Current Estimated Value $1,539,184

    Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

    3010 Grand Bay Blvd Unit 482, Longboat Key, FL 34228
    • /46

      Est $700,068

      Not Listed For Sale

      448 Gulf of Mexico Dr Unit A106, Longboat Key, FL 34228

      • 3 Beds
      • 2 Baths
      • 1,474 Sq Ft
      • Built 1970
      448 Gulf of Mexico Dr Unit A106, Longboat Key, FL 34228

      Last Sold Summary

      • 104 Days On Market

      Last Listing Agent Diana Kryszak MICHAEL SAUNDERS & COMPANY

  • /59

    $1,625,000

    • 2 Beds
    • 2 Baths
    • 2,236 Sq Ft

    791 Broadway St, Longboat Key, FL 34228

    Welcome home to 791 Broadway, nestled in the heart of historic Longbeach Village on the North end of prestigious Longboat Key. This elevated island-style residence offers the perfect blend of coastal charm, comfort, and relaxed island living. Thoughtfully designed across multiple levels including a large 11x30 third floor FLEX SPACE that could easily be converted into a 3RD BEDROOM. This home

    Matthew Voss PREFERRED SHORE LLC

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

    $5,300,000

    Sold Feb 17, 2026

    4765 Gulf of Mexico Dr Unit B202, Longboat Key, FL 34228

    • 3 Beds
    • 3.5 Baths
    • 3,368 Sq Ft
    • Built 2016

    Last Sold Summary

    • 12% Below List Price
    • $1,574/SF
    • 233 Days On Market

    Current Estimated Value $4,160,494

    Last Listing Agent Steve and Janet Walter MICHAEL SAUNDERS & COMPANY

    4765 Gulf of Mexico Dr Unit B202, Longboat Key, FL 34228
    • /2

      Est $718,697

      Not Listed For Sale

      448 Gulf of Mexico Dr Unit A204, Longboat Key, FL 34228

      • 2 Beds
      • 2 Baths
      • 1,194 Sq Ft
      • Built 1970
      448 Gulf of Mexico Dr Unit A204, Longboat Key, FL 34228

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Mairead Smialek COLDWELL BANKER REALTY

  • /30

    $675,000

    $115K PRICE DROP Under Contract
    • 1 Bed
    • 1 Bath
    • 642 Sq Ft

    225 Sands Point Rd Unit 6201, Longboat Key, FL 34228

    Under contract-accepting backup offers. Tropical elegance awaits in this thoughtfully updated Junior Suite, which pairs tranquil lagoon views with strong rental potential through the established hotel program. Impact-rated sliding glass doors lead to a private, open terrace with a glass railing, allowing the lush, tropical setting to remain the focal point while inviting the outdoors in. Inside,

    Bruce Myer COLDWELL BANKER REALTY

    225 Sands Point Rd Unit 6201, Longboat Key, FL 34228
  • /43

    $16,000 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. Rental dates are fully flexible to suit your needs — unlike most units that require a three-month minimum, this

    Michele Conn PREFERRED SHORE LLC

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

    $865,000

    Sold Mar 10, 2026

    1211 Gulf of Mexico Dr Unit 206, Longboat Key, FL 34228

    • 2 Beds
    • 2 Baths
    • 1,598 Sq Ft
    • Built 1985

    Last Sold Summary

    • 6% Below List Price
    • $541/SF
    • 23 Days On Market

    Current Estimated Value $889,414

    Last Listing Agent Lenore Treiman MICHAEL SAUNDERS & COMPANY

    1211 Gulf of Mexico Dr Unit 206, Longboat Key, FL 34228
    • /52

      Est $2,500,276

      Not Listed For Sale

      830 Tarawitt Dr, Longboat Key, FL 34228

      • 4 Beds
      • 3 Baths
      • 2,447 Sq Ft
      • Built 2015
      830 Tarawitt Dr, Longboat Key, FL 34228

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Toni Zarghami KW COASTAL LIVING III

  • /34

    $1,475,000

    $404K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,550 Sq Ft

    3010 Grand Bay Blvd Unit 493, Longboat Key, FL 34228

    One or more photo(s) has been virtually staged. Perched just one floor below the penthouse in the sought-after Grand Bay IV community on Longboat Key, this 2,550-sq.-ft. Cayman floor plan offers an exceptional opportunity to enjoy the Grand Bay lifestyle immediately. With ideal north–south exposure, this residence captures breathtaking sunrises over Sarasota Bay and stunning Gulf sunsets from two

    Ryan Ackerman COLDWELL BANKER REALTY

    3010 Grand Bay Blvd Unit 493, Longboat Key, FL 34228
  • /28

    $4,900 Per Month

    • 2 Beds
    • 2 Baths
    • 1,168 Sq Ft
    • Condo for Rent

    4420 Exeter Dr Unit 208, Longboat Key, FL 34228

    Must read entirely. 2026 RENTAL- Not Available until Nov 2026. Talk about the perfect beach place. Intercoastal view and private easy access to the beach with a private beach house! Longboat Harbour Condominium Association has tennis courts, a fitness center, Kayak launching pads, docks, fishing areas, many pools, private access to the beach on the Gulf of Mexico. Marina slips MAY be available so

    Armando Gonzalez AG REALTY SERVICES LLC

    4420 Exeter Dr Unit 208, Longboat Key, FL 34228
  • /2

    $1,200,000

    Sold Apr 03, 2026

    2123 Harbourside Dr Unit 903, Longboat Key, FL 34228

    • 3 Beds
    • 3 Baths
    • 2,352 Sq Ft
    • Built 1984

    Last Sold Summary

    • 7% Below List Price
    • $510/SF
    • 45 Days On Market

    Current Estimated Value $1,177,215

    Last Listing Agent Kathleen Wingate PREMIER SOTHEBY'S INTERNATIONAL REALTY

    2123 Harbourside Dr Unit 903, Longboat Key, FL 34228
    • /89

      Est $5,270,390

      Not Listed For Sale

      435 L Ambiance Dr Unit M908, Longboat Key, FL 34228

      • 3 Beds
      • 4.5 Baths
      • 3,220 Sq Ft
      • Built 1994
      435 L Ambiance Dr Unit M908, Longboat Key, FL 34228

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Rob Dardas MICHAEL SAUNDERS & COMPANY

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