11,645

Longboat Key, FL Homes

Section Image
  • /5

    $39,500

    408 Gulf of Mexico Dr Unit 2112, Longboat Key, FL 34228

    Welcome to Slip #2112 at The Boathouse on Longboat, rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This slip accommodates boats up to 23'6"Lx8'6"Wx7'2"H (No T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable

    Daniel Treiman MICHAEL SAUNDERS & COMPANY

    408 Gulf of Mexico Dr Unit 2112, Longboat Key, FL 34228
  • /39

    $12,000 Per Month

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

    4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228

    Longboat Key Gulf Front Vacation Rental! Gorgeous views from every window, 2 beds, 2 baths, fourth floor end unit in the wonderful boutique-style community of Tiffany Plaza. Look no further for your perfect vacation retreat, located directly on the Gulf of Mexico, this lovely condo has all you need. The updated kitchen has a center Island with breakfast bar, farm-style sink, and stainless steel

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228
  • /2

    $2,700,000

    Sold Jul 14, 2025

    549 Sloop Ln, Longboat Key, FL 34228

    • 4 Beds
    • 3.5 Baths
    • 4,127 Sq Ft
    • Built 2000

    Last Sold Summary

    • 37% Below List Price
    • $654/SF
    • 255 Days On Market

    Current Estimated Value $2,704,553

    Last Listing Agent Tracey Stetler COLDWELL BANKER REALTY

    549 Sloop Ln, Longboat Key, FL 34228
    • /2

      Est $3,861,810

      Not Listed For Sale

      1241 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

      • 3 Beds
      • 5 Baths
      • 3,400 Sq Ft
      • Built 1996
      1241 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

      Last Sold Summary

      • 278 Days On Market

  • /88

    $6,488,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 3,554 Sq Ft

    519 Rountree Dr, Longboat Key, FL 34228

    BUILT TO LAST. 519 Rountree is new construction built entirely of concrete block (CBS) across every level—unlike many barrier island homes that transition to wood-frame construction above the flood elevation. The residence has already experienced recent hurricanes without damage. NEW CONSTRUCTION. 519 ROUNTREE is a privately positioned coastal residence offering over 6,400 square feet of indoor

    Colby Lengel COMPASS FLORIDA LLC

    519 Rountree Dr, Longboat Key, FL 34228
  • /69

    $25,000 Per Month

    • 3 Beds
    • 3 Baths
    • 3,230 Sq Ft
    • House for Rent

    690 Old Compass Rd, Longboat Key, FL 34228

    Coveted lifestyle and location on one of the widest deep water canals on LONGBOAT KEY with direct access to Sarasota Bay with no bridges! This house has been totally renovated right down to the studs giving you 3,230 square feet of total luxury living. Meticulously maintained, this home has 3 bedrooms. The primary bedroom is en-suite with a king size bed, 2nd and 3rd bedrooms feature queen size

    Teresa Ribaudo JENNETTE PROPERTIES INC

    690 Old Compass Rd, Longboat Key, FL 34228
  • /2

    $2,200,000

    Sold Jan 08, 2026

    1281 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228

    • 2 Beds
    • 3 Baths
    • 2,655 Sq Ft
    • Built 1999

    Last Sold Summary

    • 12% Below List Price
    • $829/SF
    • 221 Days On Market

    Current Estimated Value $2,249,635

    Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

    1281 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228
    • /80

      Est $1,535,345

      Not Listed For Sale

      2020 Harbourside Dr Unit 434/435, Longboat Key, FL 34228

      • 3 Beds
      • 3 Baths
      • 2,462 Sq Ft
      • Built 1984
      2020 Harbourside Dr Unit 434/435, Longboat Key, FL 34228

      Last Sold Summary

      • 0 Days On Market

  • /51

    $1,050,000

    • 2 Beds
    • 2.5 Baths
    • 1,392 Sq Ft

    1281 Gulf of Mexico Dr Unit 111, Longboat Key, FL 34228

    Welcome to a little piece of paradise on Longboat Key at the stunning gated Gulf-front condominium community of Water Club, which offers a coastal lifestyle complete with direct access to sandy beaches, high-end amenities and exceptional security and concierge services. This designer-inspired, two-bedroom, 2.5-bath condominium is on the newer north building's plaza level and features nearly 1,400

    Kathleen Ucci PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1281 Gulf of Mexico Dr Unit 111, Longboat Key, FL 34228
  • /55

    $11,950 Per Month

    • 2 Beds
    • 2 Baths
    • 1,470 Sq Ft
    • Condo for Rent

    2425 Gulf of Mexico Dr Unit 14B, 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,

    Andrey markov ANMARK REALTY LLC

    2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
  • /2

    $1,690,000

    Sold May 27, 2026

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

    • 3 Beds
    • 3 Baths
    • 2,365 Sq Ft
    • Built 1991

    Last Sold Summary

    • 35% Below List Price
    • $715/SF
    • 333 Days On Market

    Current Estimated Value $1,782,803

    Last Listing Agent Debra Pitell-Hauge MICHAEL SAUNDERS & COMPANY

    340 Gulf of Mexico Dr Unit 124, Longboat Key, FL 34228
    • /29

      Not Listed For Sale

      3710 Gulf of Mexico Dr Unit E23, Longboat Key, FL 34228

      • 2 Beds
      • 1 Bath
      • 693 Sq Ft
      • Built 2007
      3710 Gulf of Mexico Dr Unit E23, Longboat Key, FL 34228

      Last Sold Summary

      • 61 Days On Market

  • /44

    $9,400,000

    $2M PRICE DROP
    • 5 Beds
    • 5 Baths
    • 5,982 Sq Ft

    600 Putter Ln, Longboat Key, FL 34228

    Welcome to Paradise on Longboat Key. This coastal modern home is located on the direct bayfront with a total of 270 feet of waterfront on an oversized lot consisting of 18,290 square feet. As you enter the home, your first view is a serene and expansive view of Sarasota Bay all the way from the Ringling Museum to Downtown Sarasota and the Ringling Bridge. Enjoy different types of boating as the

    Kathleen Callender FLORIDA CAPITAL REALTY

    600 Putter Ln, Longboat Key, FL 34228
  • /44

    $15,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 2,135 Sq Ft
    • Condo for Rent

    1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228

    Gorgeous gulf front vacation rental available now through 2027!! You will love this wonderfully renovated 10th-story penthouse condominium in the Promenade on Longboat Key. This elegant residence offers two bedrooms and two and one half baths in over 2,100 square feet of living space. Fabulous views of the Gulf from every window. No expense was spared during this renovation; you will love the

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1211 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228
  • /2

    $3,100,000

    Sold Jan 07, 2026

    435 L Ambiance Dr Unit K506, Longboat Key, FL 34228

    • 3 Beds
    • 3.5 Baths
    • 2,820 Sq Ft
    • Built 1994

    Last Sold Summary

    • 6% Below List Price
    • $1,099/SF
    • 12 Days On Market

    Current Estimated Value $3,176,279

    Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

    435 L Ambiance Dr Unit K506, Longboat Key, FL 34228
    • /69

      Est $806,233

      Not Listed For Sale

      5270 Gulf of Mexico Dr Unit 502, Longboat Key, FL 34228

      • 3 Beds
      • 3 Baths
      • 1,498 Sq Ft
      • Built 1974
      5270 Gulf of Mexico Dr Unit 502, Longboat Key, FL 34228

      Last Sold Summary

      • 58 Days On Market

  • /49

    $3,140,000

    $135K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,550 Sq Ft

    595 Bowsprit Ln, Longboat Key, FL 34228

    Longboat Key Waterfront Perfection! Experience the ultimate coastal lifestyle in this 4-bedroom, 2.5-bath home, effective year 2016, in the prestigious Country Club Shores community—just three homes from Sarasota Bay with quick access to the Gulf of Mexico. Boater’s paradise with two boat lifts (20,000 lb and 7,000 lb), a new seawall, and private dock complete with a custom fish cleaning station

    Melissa Gissinger MICHAEL SAUNDERS & COMPANY

    595 Bowsprit Ln, Longboat Key, FL 34228
  • /26

    $7,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    640 Broadway St, Longboat Key, FL 34228

    Step into living history in the heart of Historic Longbeach Village. This exceptional property occupies land that was part of Civil War veteran Thomas Mann’s 144-acre homestead, where in 1891 he built the island’s first permanent residence just steps away. This serene corner lot is where Longboat Key truly began! Fully rebuilt and elevated in 2025 to the highest modern standards after the 2024

    Christina Vescovo LPT REALTY, LLC

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

    $8,625,000

    Sold Feb 23, 2026

    600 Wedge Ln, Longboat Key, FL 34228

    • 4 Beds
    • 4.5 Baths
    • 4,338 Sq Ft
    • Built 2016

    Last Sold Summary

    • 13% Below List Price
    • $1,988/SF
    • 65 Days On Market

    Current Estimated Value $8,504,734

    Last Listing Agent Debra Lichter SARASOTA BEACH TO BAY INC

    600 Wedge Ln, Longboat Key, FL 34228
    • /48

      Not Listed For Sale

      210 Sands Point Rd Unit 2603/04, Longboat Key, FL 34228

      • 2 Beds
      • 2 Baths
      • 1,284 Sq Ft
      • Built 1982
      210 Sands Point Rd Unit 2603/04, Longboat Key, FL 34228

      Last Sold Summary

      • 6 Days On Market

  • /17

    $300,000

    2800 Harbourside Dr Unit E-07, Longboat Key, FL 34228

    A favorite dock in the Marina with ample turning radius. This 55 x 21 foot slip at Longboat Key Club Moorings is located on the west side of the Marina. Club membership is not 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 village that

    Jennifer Wilson LBRE LLC

    2800 Harbourside Dr Unit E-07, Longboat Key, FL 34228
  • /41

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,409 Sq Ft
    • Property for Rent

    1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228

    Available 07/01/2025 THROUGH 12/30/2025 RENTED SEASON JAN, 2026 THROUGH APRIL, 2026(POSSIBLE ANNUAL)Privateer North PH located Behind the Gates of Longboat Key. GULF VIEWS FROM EVERY ROOM. A top of the line remodel with 2 spacious bedrooms with walk-in closets. The master bedroom ensuite has a king size bed and guest bedroom is a queen size. 2 updated bathrooms with walk-in closets and views of

    Marni Hayden CHROME REALTY LLC

    1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228
  • /2

    $525,000

    Sold Mar 13, 2026

    4350 Chatham Dr Unit 307, Longboat Key, FL 34228

    • 2 Beds
    • 2 Baths
    • 1,072 Sq Ft
    • Built 1969

    Last Sold Summary

    • 19% Below List Price
    • $490/SF
    • 87 Days On Market

    Current Estimated Value $545,790

    Last Listing Agent Marsha Winegarden WAGNER REALTY

    4350 Chatham Dr Unit 307, Longboat Key, FL 34228
    • /29

      Est $1,172,281

      Not Listed For Sale

      1445 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

      • 2 Beds
      • 2.5 Baths
      • 1,859 Sq Ft
      • Built 1982
      1445 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

      Last Sold Summary

      • 155 Days On Market

  • /62

    $1,650,000

    $350K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 2,028 Sq Ft

    524 Ketch Ln, Longboat Key, FL 34228

    Under contract-accepting backup offers. Discover the quintessential Longboat Key lifestyle in this classic masonry beach home located just “3” properties in from Sarasota Bay. Boasting 110 feet of canal frontage, your own private dock, a 7,500 lb. boatlift to complement this classic waterfront treasure it offers direct access for boating, fishing, and kayaking, with frequent visits from playful

    Kathy Callahan MICHAEL SAUNDERS & COMPANY

    524 Ketch Ln, Longboat Key, FL 34228
  • /63

    $10,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,463 Sq Ft
    • Condo for Rent

    2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228

    Booked Dec 1st 2026-March 31st 2027. **Beachfront Bliss with Stunning Gulf Views** Experience coastal living at its finest in this beautifully updated beachfront condo. The bright, open living area flows seamlessly onto a spacious private balcony where you can enjoy panoramic Gulf views, sea breezes, and unforgettable sunsets. The renovated kitchen features sleek countertops, stainless steel

    Jennifer Le Blanc PRECISE REALTY CORP

    2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228
  • /2

    $625,000

    Sold Aug 07, 2025

    321 N Shore Rd Unit LOT ONLY, Longboat Key, FL 34228

    • Land
    • 6,098 Sq Ft
    • $4,464,286 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 185 Days On Market

    Current Estimated Value $623,443

    Last Listing Agent Brian Leakeas COLDWELL BANKER REALTY

    321 N Shore Rd Unit LOT ONLY, Longboat Key, FL 34228
    • /42

      Est $855,756

      Not Listed For Sale

      1085 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

      • 2 Beds
      • 2 Baths
      • 1,392 Sq Ft
      • Built 1981
      1085 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

      Last Sold Summary

      • 123 Days On Market

  • /60

    $1,049,000

    • 3 Beds
    • 2 Baths
    • 1,492 Sq Ft

    1955 Gulf of Mexico Dr Unit G6311, Longboat Key, FL 34228

    Experience the coastal gulf front living lifestyle to its fullest, in this 3-bedroom 2 bath condo with views of the Gulf from inside as well as the 2 balconies. Make this your new oasis and enjoy the sunsets off one of your two separate balconies (one off the main living area and another private balcony for the primary bedroom). Start experiencing this 3-bedroom condo at Seaplace which is located

    Bruce Meyer MICHAEL SAUNDERS & COMPANY

    1955 Gulf of Mexico Dr Unit G6311, Longboat Key, FL 34228
  • /28

    $2,500 Per Month

    • 1 Bed
    • 1 Bath
    • 721 Sq Ft
    • Condo for Rent

    3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228

    1-bed, 1-bath seasonal rental paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy deeded beach access and the community’s private beach area, complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on

    Dakota Magnus FLORIDA GALLERY REAL ESTATE

    3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228
  • /2

    $2,285,000

    Sold Mar 31, 2026

    617 Neptune Ave, Longboat Key, FL 34228

    • 3 Beds
    • 3.5 Baths
    • 2,939 Sq Ft
    • Built 2019

    Last Sold Summary

    • 5% Below List Price
    • $777/SF
    • 7 Days On Market

    Current Estimated Value $2,298,983

    Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY

    617 Neptune Ave, Longboat Key, FL 34228
    • /19

      Not Listed For Sale

      2800 Harbourside Dr Unit E-06, Longboat Key, FL 34228

      • Studio
      • 1,155 Sq Ft
      • Built 1982
      2800 Harbourside Dr Unit E-06, Longboat Key, FL 34228

      Last Sold Summary

      • 5 Days On Market

  • /30

    $485,000

    Open Sat 1PM - 3PM $40K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 992 Sq Ft

    605 Sutton Place Unit 102, Longboat Key, FL 34228

    Sutton Place is perfectly situated on the tropical grounds of the Longboat Harbour Community. The two-bedroom, two-bathroom unit features beautiful views of the Sarasota Bay, spacious living area, full-size kitchen with stainless steel appliances and granite countertops, dining area and 3 flat-screen TV’s. If the amenities on the interior of the condo aren’t enough – the community of Sutton Place

    Larry Starr SVN COMMERCIAL ADVISORY GROUP

    605 Sutton Place Unit 102, Longboat Key, FL 34228
  • /39

    $30,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,230 Sq Ft
    • House for Rent

    6925 Longboat Dr S, Longboat Key, FL 34228

    Available May-December with a 90 Day minimum at $15,550 per month plus taxes and fees booked for 2024 season. Welcome to The Captain's Quarters! This newly built Luxury Rental Home on Longboat Key has everything for you and your family to enjoy your home away from home! This three-story 3-bedroom, 3.5-bath home boasts top of the line features, Smart Home technology, and beautiful decor

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    6925 Longboat Dr S, Longboat Key, FL 34228
  • /2

    $600,000

    Sold Apr 08, 2026

    521 Broadway St, Longboat Key, FL 34228

    • Land
    • 1 Acre
    • $600,000 per Acre

    Last Sold Summary

    • 28% Below List Price
    • 0 Days On Market

    Current Estimated Value $633,956

    Last Listing Agent Gerald Cunningham KELLER WILLIAMS ON THE WATER S

    521 Broadway St, Longboat Key, FL 34228
    • /18

      Est $342,737

      Not Listed For Sale

      2600 Harbourside Dr Unit L-08, Longboat Key, FL 34228

      • Studio
      • Built 1983
      2600 Harbourside Dr Unit L-08, Longboat Key, FL 34228

      Last Sold Summary

      • 381 Days On Market

  • /20

    $425,000

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

    Ask an L-dock boater, they will tell you it’s the best dock in the marina. Slip is near the seawall, just a few flat steps to your parked vehicle with easy in/out access. A 68 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina. This slip is one of the very few slips at the marina with a direct view of the Sarasota cityscape and colorfully lit Ringling bridge. Unlike most slips here, this does

    Jennifer Wilson LBRE LLC

    2600 Harbourside Dr Unit L-05, Longboat Key, FL 34228
  • /59

    $11,000 Per Month

    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft
    • House for Rent

    3390 Bayou Sound, Longboat Key, FL 34228

    **Two-Month Minimum Rental** Escape to paradise at this beautifully updated Bay Isles retreat on Longboat Key. Nestled among lush tropical landscaping and majestic oak trees, this private island getaway offers the perfect blend of luxury, comfort, and relaxation. Located within the exclusive gated community of Bay Isles, guests enjoy easy access to Longboat Key's world-renowned beaches, marinas,

    Jennifer Le Blanc PRECISE REALTY CORP

    3390 Bayou Sound, Longboat Key, FL 34228
  • /2

    $6,000,000

    Sold Oct 03, 2025

    1591 Gulf of Mexico Dr Unit 511, Longboat Key, FL 34228

    • 2 Beds
    • 2.5 Baths
    • 3,130 Sq Ft
    • Built 2024

    Last Sold Summary

    • 14% Below List Price
    • $1,917/SF
    • 99 Days On Market

    Current Estimated Value $6,029,002

    Last Listing Agent Kim Ogilvie MICHAEL SAUNDERS & COMPANY

    1591 Gulf of Mexico Dr Unit 511, Longboat Key, FL 34228
    • /2

      Est $666,205

      Not Listed For Sale

      5260 Gulf of Mexico Dr Unit 412, Longboat Key, FL 34228

      • 3 Beds
      • 3 Baths
      • 1,453 Sq Ft
      • Built 1974
      5260 Gulf of Mexico Dr Unit 412, Longboat Key, FL 34228

      Last Sold Summary

      • 45 Days On Market

Showing Results 321 - 360, Page 9 of 18

How to Buy a Home How to Finance a Home How to Sell a Home