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Longboat Key, FL Homes for Sale under $500,000

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  • 3710 Gulf of Mexico Dr Unit F2, Longboat Key, FL 34228
    3710 Gulf of Mexico Dr Unit F2, Longboat Key, FL 34228
    3710 Gulf of Mexico Dr Unit F2, Longboat Key, FL 34228
    /45

    $475,000

    New Construction
    • 2 Beds
    • 2 Baths
    • 740 Sq Ft

    3710 Gulf of Mexico Dr Unit F2, Longboat Key, FL 34228

    Island Living at Its Finest – Brand New Home on Longboat Key. Welcome to Gulfshore of Longboat, a highly desirable waterfront co-op community offering private beach access, boat docks, and sweeping views of the Gulf of Mexico and Sarasota Bay. This beautifully built 2-bedroom home combines modern efficiency with relaxed coastal living. An outdoor bathroom with a shower is a wonderful convenience

    Agent Photo

    Marsha Winegarden

    WAGNER REALTY

    (941) 239-0910

    3710 Gulf of Mexico Dr Unit F2, Longboat Key, FL 34228
  • 718 Spanish Dr N, Longboat Key, FL 34228
    718 Spanish Dr N, Longboat Key, FL 34228
    718 Spanish Dr N, Longboat Key, FL 34228
    /20

    $435,000

    $15K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,327 Sq Ft

    718 Spanish Dr N, Longboat Key, FL 34228

    Discover Longboat Key waterfront living at its very best at 718 Spanish Dr N, a beautifully updated freestanding villa in the sought-after Spanish Main Yacht Club. This home has been completely renovated to today’s highest standards following Hurricane Ian, delivering a fresh, high-end coastal finish throughout with meticulous craftsmanship and premium materials. Just steps from your door, enjoy

    John Woodward SARASOTA REAL ESTATE GROUP

    718 Spanish Dr N, Longboat Key, FL 34228
  • 2600 Harbourside Dr Unit L-03, Longboat Key, FL 34228
    2600 Harbourside Dr Unit L-03, Longboat Key, FL 34228
    2600 Harbourside Dr Unit L-03, Longboat Key, FL 34228
    /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
  • 6750 Gulf of Mexico Dr Unit 163, Longboat Key, FL 34228
    6750 Gulf of Mexico Dr Unit 163, Longboat Key, FL 34228
    6750 Gulf of Mexico Dr Unit 163, Longboat Key, FL 34228
    /47

    $490,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,449 Sq Ft

    6750 Gulf of Mexico Dr Unit 163, Longboat Key, FL 34228

    One or more photo(s) has been virtually staged. Tucked within the intimate Whitney Beach community on Longboat Key's serene north end, this beautifully reimagined two-bedroom, two-bath end unit occupies one of the community's most coveted positions — a corner residence offering protected water views over Bishop's Bayou from both the kitchen and living room, sheltered from the wake and noise of

    Karen Whitaker PREMIER SOTHEBY'S INTERNATIONAL REALTY

    6750 Gulf of Mexico Dr Unit 163, Longboat Key, FL 34228
  • 2600 Harbourside Dr Unit J-09, Longboat Key, FL 34228
    2600 Harbourside Dr Unit J-09, Longboat Key, FL 34228
    2600 Harbourside Dr Unit J-09, Longboat Key, FL 34228
    /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
  • 711 Spanish Dr S, Longboat Key, FL 34228
    711 Spanish Dr S, Longboat Key, FL 34228
    711 Spanish Dr S, Longboat Key, FL 34228
    /59

    $435,000

    • 2 Beds
    • 2 Baths
    • 1,327 Sq Ft

    711 Spanish Dr S, Longboat Key, FL 34228

    Calling all boaters. If you have ever considered living on Longboat Key in sunny beautiful Florida, now is your chance! This amazing villa is available and ready for you to move to paradise! 711 Spanish Dr. S. is a 2 bedroom/2bath home that has been newly renovated in 2025/2026 and it is beautiful! Entering the home your eyes are immediately drawn upwards to the gorgeous open beam 10’-12’ ceiling

    Kimberly Freiwald PREMIER SOTHEBY'S INTERNATIONAL REALTY

    711 Spanish Dr S, Longboat Key, FL 34228
  • 2800 Harbourside Dr Unit E-07, Longboat Key, FL 34228
    2800 Harbourside Dr Unit E-07, Longboat Key, FL 34228
    2800 Harbourside Dr Unit E-07, Longboat Key, FL 34228
    /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
  • 605 Sutton Place Unit 102, Longboat Key, FL 34228
    605 Sutton Place Unit 102, Longboat Key, FL 34228
    605 Sutton Place Unit 102, Longboat Key, FL 34228
    /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
  • 2600 Harbourside Dr Unit L-05, Longboat Key, FL 34228
    2600 Harbourside Dr Unit L-05, Longboat Key, FL 34228
    2600 Harbourside Dr Unit L-05, Longboat Key, FL 34228
    /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
  • 2600 Harbourside Dr Unit P-07, Longboat Key, FL 34228
    2600 Harbourside Dr Unit P-07, Longboat Key, FL 34228
    2600 Harbourside Dr Unit P-07, Longboat Key, FL 34228
    /19

    $225,000

    2600 Harbourside Dr Unit P-07, Longboat Key, FL 34228

    Quick access to dock you boat! Located just inside the marina on the east side. This 48 x 20 foot slip at Longboat Key Club Moorings is located on the north side of P-dock. 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

    Jennifer Wilson LBRE LLC

    2600 Harbourside Dr Unit P-07, Longboat Key, FL 34228
  • 600 Sutton Place Unit 302, Longboat Key, FL 34228
    600 Sutton Place Unit 302, Longboat Key, FL 34228
    600 Sutton Place Unit 302, Longboat Key, FL 34228
    /48

    $475,000

    $25K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,132 Sq Ft

    600 Sutton Place Unit 302, Longboat Key, FL 34228

    Enjoy the best of the Longboat Key lifestyle in this beautifully updated 2-bedroom, 2-bath waterfront condo at Sutton Place, offering a rare Gulf-to-Bay experience with Sarasota Bay views and PRIVATE DEEDED BEACH ACCESS to a Gulf-front beach just across the street. This light and bright residence features a spacious, open floor plan with quality finishes throughout, including porcelain tile and

    Christina Weger COLDWELL BANKER REALTY

    600 Sutton Place Unit 302, Longboat Key, FL 34228
  • 729 Saint Judes Dr S Unit 3, Longboat Key, FL 34228
    729 Saint Judes Dr S Unit 3, Longboat Key, FL 34228
    729 Saint Judes Dr S Unit 3, Longboat Key, FL 34228
    /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
  • 509 Spanish Dr N, Longboat Key, FL 34228
    509 Spanish Dr N, Longboat Key, FL 34228
    509 Spanish Dr N, Longboat Key, FL 34228
    /34

    $369,000

    • 2 Beds
    • 2 Baths
    • 1,357 Sq Ft

    509 Spanish Dr N, Longboat Key, FL 34228

    STEPS FROM THE BEACH.....WATERFRONT COMMUNITY......DEEDED BEACH ACCESS......FULLY RENOVATED..........IMPACT WINDOWS..........COMMUNITY POOL...........Just **432 steps from the beach**, this is where coastal living stops being a dream and becomes your daily rhythm. Morning walks on soft sand, sunset returns under glowing skies, and the constant sense that the water is always just around the

    Garrett Sedlacek KELLER WILLIAMS ON THE WATER S

    509 Spanish Dr N, Longboat Key, FL 34228
  • 2600 Harbourside Dr Unit L-11, Longboat Key, FL 34228
    2600 Harbourside Dr Unit L-11, Longboat Key, FL 34228
    2600 Harbourside Dr Unit L-11, Longboat Key, FL 34228
    /19

    $425,000

    2600 Harbourside Dr Unit L-11, Longboat Key, FL 34228

    Ask an L-dock boater, they will tell you it’s the best dock in the marina. Slip mid-pier ono the north side of the dock, 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 requires membership in the Longboat Key Club. This slip is one of the very few slips at the marina with a direct view of the Sarasota

    Jennifer Wilson LBRE LLC

    2600 Harbourside Dr Unit L-11, Longboat Key, FL 34228
  • 2800 Harbourside Dr Unit E-08, Longboat Key, FL 34228
    2800 Harbourside Dr Unit E-08, Longboat Key, FL 34228
    2800 Harbourside Dr Unit E-08, Longboat Key, FL 34228
    /20

    $250,000

    2800 Harbourside Dr Unit E-08, Longboat Key, FL 34228

    access on the south side of the pier! A 60 ft. x 21 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.. 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,

    Jennifer Wilson LBRE LLC

    2800 Harbourside Dr Unit E-08, Longboat Key, FL 34228
  • 3806 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228
    /38

    $335,000

    • 2 Beds
    • 2 Baths
    • 1,046 Sq Ft

    3806 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228

    Discover Your Slice of Paradise! This charming turnkey 2-bedroom, 2-bath condo is perfectly positioned between the Gulf of Mexico and Sarasota Bay, offering breathtaking sunrise and sunset views. Enjoy deeded beach access complete with lounge chairs, picnic tables, charcoal grills, and outdoor showers. On the bayside, recent upgrades include a new dock with first-come boat slips, community

    Kathleen Magnus FLORIDA GALLERY REAL ESTATE

    3806 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228
  • 96 Main Street Dr, Longboat Key, FL 34228
    96 Main Street Dr, Longboat Key, FL 34228
    96 Main Street Dr, Longboat Key, FL 34228
    /9

    $425,000

    New Construction
    • 2 Beds
    • 2 Baths
    • 758 Sq Ft

    96 Main Street Dr, Longboat Key, FL 34228

    Welcome to PARADISE!!! Award winning beaches/sunsets on the Gulf side and a beautiful bay on the other. Sunrise to sunset this location can only make you smile. Enjoy the huge community heated pool and recently remodeled dockside clubhouse next to your brand new, 2026, elevated 2-bedroom, 2 bath, open floorplan home. The home is built by Skyline, highly regarded in the industry, winning

    Kyle Adams EVENTIDE REALTY LLC

    96 Main Street Dr, Longboat Key, FL 34228
  • 2600 Harbourside Dr Unit O-04, Longboat Key, FL 34228
    2600 Harbourside Dr Unit O-04, Longboat Key, FL 34228
    2600 Harbourside Dr Unit O-04, Longboat Key, FL 34228
    /15

    $235,000

    2600 Harbourside Dr Unit O-04, Longboat Key, FL 34228

    Great city skyline views and easy access! This 45 x 20 foot slip at Longboat Key Club Moorings is located on the South side of O-dock. 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 includes

    Jennifer Wilson LBRE LLC

    2600 Harbourside Dr Unit O-04, Longboat Key, FL 34228
  • 701 Saint Judes Dr S Unit 3, Longboat Key, FL 34228
    701 Saint Judes Dr S Unit 3, Longboat Key, FL 34228
    701 Saint Judes Dr S Unit 3, Longboat Key, FL 34228
    /12

    $259,000

    • 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
  • 2600 Harbourside Dr Unit C-13, Longboat Key, FL 34228
    2600 Harbourside Dr Unit C-13, Longboat Key, FL 34228
    2600 Harbourside Dr Unit C-13, Longboat Key, FL 34228
    /23

    $489,500

    2600 Harbourside Dr Unit C-13, Longboat Key, FL 34228

    72' x 21' Boat Slip on C-Dock at Longboat Key Moorings Marina for Sale ~ AND THERE IS NO MEMBERSHIP REQUIREMENT to join The Longboat Key Club (which is now $115,000) and the annual fee of $8388 plus food & beverage fees. The beauty of this TWO-LEVEL dock is... there is no covenant BUT if you chose to join the Longboat Key Club, there are multiple membership packages to choose from which give you

    Rian Carver FINE PROPERTIES

    2600 Harbourside Dr Unit C-13, Longboat Key, FL 34228
  • 3710 Gulf of Mexico Dr Unit G12, Longboat Key, FL 34228
    3710 Gulf of Mexico Dr Unit G12, Longboat Key, FL 34228
    3710 Gulf of Mexico Dr Unit G12, Longboat Key, FL 34228
    /19

    $299,000

    $21K PRICE DROP
    • Land
    • 1,742 Sq Ft
    • $7,475,000 per Acre

    3710 Gulf of Mexico Dr Unit G12, Longboat Key, FL 34228

    ON THE WATER - SPECTACULAR VIEWS: This lot sits directly on the marina seawall, in Gulfshore, and has extended views of Sarasota Bay. When a new elevated home is placed on this parcel of land, the views will only become more impressive. There are contractors ready for you to design your interior layout and they will build your home to meet all FEMA building codes. The community of Gulfshore, is

    Bill Shuttleworth EDGEWATER REAL ESTATE, INC

    3710 Gulf of Mexico Dr Unit G12, Longboat Key, FL 34228
  • 6700 Gulf of Mexico Dr Unit 139, Longboat Key, FL 34228
    6700 Gulf of Mexico Dr Unit 139, Longboat Key, FL 34228
    6700 Gulf of Mexico Dr Unit 139, Longboat Key, FL 34228
    /52

    $475,000

    $24K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,305 Sq Ft

    6700 Gulf of Mexico Dr Unit 139, Longboat Key, FL 34228

    “PRICED BELOW MARKET VALUE NOW REDUCED TO $475,000” Fully renovated 2 Bedroom 2 Bath Whitney Beach Bay Side FIRST FLOOR condo ready for occupancy. It has undergone FEMA approved storm mitigation & has had a full rebuild & inspections. All new handsome Luxury Vinyl Plank flooring throughout plus tile in the primary bedroom’s stunning en suite with shower & 2nd bathroom with tub. Large, impact

    Maruta Miluns MICHAEL SAUNDERS & COMPANY

    6700 Gulf of Mexico Dr Unit 139, Longboat Key, FL 34228
  • 2600 Harbourside Dr Unit R-07, Longboat Key, FL 34228
    2600 Harbourside Dr Unit R-07, Longboat Key, FL 34228
    2600 Harbourside Dr Unit R-07, Longboat Key, FL 34228
    /30

    $400,000

    2600 Harbourside Dr Unit R-07, Longboat Key, FL 34228

    70 x 21 Boat Slip on R-dock at Longboat Key Moorings Marina for sale. This is a great slip with exceptional views of Sarasota Bay and the city skyline. Easy in/out boat access too. LBK Club membership is optional. 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, Marina village

    Jennifer Wilson LBRE LLC

    2600 Harbourside Dr Unit R-07, Longboat Key, FL 34228
  • 4380 Exeter Dr Unit 202, Longboat Key, FL 34228
    4380 Exeter Dr Unit 202, Longboat Key, FL 34228
    4380 Exeter Dr Unit 202, Longboat Key, FL 34228
    /37

    $499,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    4380 Exeter Dr Unit 202, Longboat Key, FL 34228

    Experience the ultimate Bay-to-Beach lifestyle in this turnkey 2-bedroom, 2-bath condo at Longboat Harbour, where nearly every room offers sparkling water views and a sense of calm that only waterfront living can bring. Perfect for investors or seasonal residents, this home combines desirable updates with a lifestyle that’s hard to beat. Fully updated in 2025, this home blends modern luxury with

    Ryan Skrzypkowski COLDWELL BANKER REALTY

    4380 Exeter Dr Unit 202, Longboat Key, FL 34228
  • 2850 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
    2850 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
    2850 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
    /22

    $399,000

    $50K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 695 Sq Ft

    2850 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228

    Welcome to Neptune on Longboat Key — a charming community where coastal comfort meets relaxed island living. This bright 2-bedroom, 1-bath residence features tile flooring throughout, a full kitchen with quality appliances, and a beautifully tiled bath. The open living and dining area leads to a screened lanai surrounded by lush tropical landscaping — the perfect spot to enjoy morning coffee and

    Bruce Myer COLDWELL BANKER REALTY

    2850 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
  • 4360 Chatham Dr Unit 305, Longboat Key, FL 34228
    4360 Chatham Dr Unit 305, Longboat Key, FL 34228
    4360 Chatham Dr Unit 305, Longboat Key, FL 34228
    /69

    $320,000

    $19K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 747 Sq Ft

    4360 Chatham Dr Unit 305, Longboat Key, FL 34228

    "Reduced", don't wait any longer .Waterfront living made easy! This furnished 1-bedroom, 1-bath condo is move-in ready and features beautiful tile flooring throughout, an updated kitchen, and an enclosed lanai perfect for relaxing. Just steps to the beach and loaded with amenities including four heated pools, private gated beach parking with pavilion and restrooms, beach chair storage, pickleball

    Malihe Karimi MICHAEL SAUNDERS & COMPANY

    4360 Chatham Dr Unit 305, Longboat Key, FL 34228
  • 2600 Harbourside Dr Unit N-05, Longboat Key, FL 34228
    2600 Harbourside Dr Unit N-05, Longboat Key, FL 34228
    2600 Harbourside Dr Unit N-05, Longboat Key, FL 34228
    /19

    $225,000

    $25K PRICE DROP

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

    Great east bank location at Longboat Key Club Moorings for this 45 x 20 ft. slip in the marina. 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 village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and

    Jennifer Wilson LBRE LLC

    2600 Harbourside Dr Unit N-05, Longboat Key, FL 34228
  • 4310 Falmouth Dr Unit 304, Longboat Key, FL 34228
    4310 Falmouth Dr Unit 304, Longboat Key, FL 34228
    4310 Falmouth Dr Unit 304, Longboat Key, FL 34228
    /44

    $360,000

    $39K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 747 Sq Ft

    4310 Falmouth Dr Unit 304, Longboat Key, FL 34228

    Unlock the Door to Your Dream Beach and Boating Lifestyle! Step into a world of unparalleled charm with this move-in ready, fully furnished gem on Longboat Key. This isn’t just a home; it’s a transformative lifestyle choice for those craving adventure, relaxation, and vibrant social connections. Picture yourself waking up to breathtaking bay views every morning from your stylish condo, featuring

    Rachel Rademacher HOUSE MATCH

    4310 Falmouth Dr Unit 304, Longboat Key, FL 34228
  • 4320 Falmouth Dr Unit 103, Longboat Key, FL 34228
    4320 Falmouth Dr Unit 103, Longboat Key, FL 34228
    4320 Falmouth Dr Unit 103, Longboat Key, FL 34228
    /69

    $499,000

    $26K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,072 Sq Ft

    4320 Falmouth Dr Unit 103, Longboat Key, FL 34228

    “ Significant Reduction for a quick sale , A true Opportunity waterfront Move In Ready" Luxury Waterfront Living | Proven Income PotentialExperience refined coastal living in this pristine, pleasantly updated 2-bedroom, 2-bath residence, offered fully furnished and move-in ready. Enjoy spectacular harbor and Intracoastal water views from both the living room and bedroom, extending to the

    Malihe Karimi MICHAEL SAUNDERS & COMPANY

    4320 Falmouth Dr Unit 103, Longboat Key, FL 34228
  • 4350 Chatham Dr Unit 106, Longboat Key, FL 34228
    4350 Chatham Dr Unit 106, Longboat Key, FL 34228
    4350 Chatham Dr Unit 106, Longboat Key, FL 34228
    /70

    $399,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,072 Sq Ft

    4350 Chatham Dr Unit 106, Longboat Key, FL 34228

    Light, bright, charming and ready to move into! Kitchen gutted to studs, totally updated.Tile floors, lots of closet space throughout. Updated baths, Enclosed Lanai with tile floors and electric shades overlooks lovely water view. Lovely updated decor. Furnishings are negotiable . Longboat Harbour is amenity packed- 4 heated pools, tennis/pickleball, At the clubhouse/communinity center there

    Michael Yawitz MICHAEL SAUNDERS & COMPANY

    4350 Chatham Dr Unit 106, Longboat Key, FL 34228
  • 6700 Gulf of Mexico Dr Unit 118, Longboat Key, FL 34228
    6700 Gulf of Mexico Dr Unit 118, Longboat Key, FL 34228
    6700 Gulf of Mexico Dr Unit 118, Longboat Key, FL 34228
    /41

    $387,561

    • 1 Bed
    • 1 Bath
    • 990 Sq Ft

    6700 Gulf of Mexico Dr Unit 118, Longboat Key, FL 34228

    ...shortstories " Just imagine your boat or kayak is out the back door..You and your best friend daisy and buddy..go for daily walk...Pets are allowed !!!!..551 steps and you are swimming on the blue torquise water of the Gulf of America .You live on an island of Longboat key. This beautifully first floor condo offers breathtaking water views of dolphins easy water access and the possibility rent

    Gerald Cunningham KELLER WILLIAMS ON THE WATER S

    6700 Gulf of Mexico Dr Unit 118, Longboat Key, FL 34228
  • 3806 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    /19

    $295,000

    $10K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 712 Sq Ft

    3806 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228

    Discover coastal living at its finest with this charming condominium located on Gulf of Mexico Dr, Longboat Key. This residence offers stunning ocean views and easy access to beautiful beaches. The open-concept layout features modern finishes, a spacious living area, and a well-appointed kitchen. Enjoy relaxing on the private balcony overlooking the serene surroundings. The community amenities

    Steven Koleno BEYCOME OF FLORIDA LLC

    3806 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
  • 4380 Exeter Dr Unit 101, Longboat Key, FL 34228
    4380 Exeter Dr Unit 101, Longboat Key, FL 34228
    4380 Exeter Dr Unit 101, Longboat Key, FL 34228
    /81

    $389,500

    • 2 Beds
    • 2 Baths
    • 1,376 Sq Ft

    4380 Exeter Dr Unit 101, Longboat Key, FL 34228

    Investor alert. Great investment opportunity! Condominium is in great condition. Best price for two-bedroom, two-bath condominium in sought after community of Longboat Harbour. Motivated sellers, ready to have a new buyer enjoy this lovely waterfront first-floor end-unit condominium. New roof, all assessments paid, granite countertops, kitchen open to living area. All glass lanai, tile throughout

    Kimberly Freiwald PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4380 Exeter Dr Unit 101, Longboat Key, FL 34228
  • 667 El Centro, Longboat Key, FL 34228
    667 El Centro, Longboat Key, FL 34228
    667 El Centro, Longboat Key, FL 34228
    /41

    $380,000

    • 2 Beds
    • 2 Baths
    • 1,327 Sq Ft

    667 El Centro, Longboat Key, FL 34228

    New photos coming on this beautifully updated free-standing villa in Spanish Main Yacht Club on Longboat Key, a warm and vital boating community with private beach access, pool, clubhouse and boat slips. The community is undergoing a renaissance of sorts as many units (including this one) did have water intrusion in the summer storms of 2024. This owner contracted with the community contractor.

    Holly Switow PREMIER SOTHEBY'S INTERNATIONAL REALTY

    667 El Centro, Longboat Key, FL 34228
  • 2600 Harbourside Dr Unit B-08, Longboat Key, FL 34228
    2600 Harbourside Dr Unit B-08, Longboat Key, FL 34228
    2600 Harbourside Dr Unit B-08, Longboat Key, FL 34228
    /19

    $425,000

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

    A 85 ft. x 28 ft. Boat Slip at Longboat Key Moorings Marina; extra long finger pier, wide beam, and extra wide finger pier. This is a Yacht Club slip. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. 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

    Jennifer Wilson LBRE LLC

    2600 Harbourside Dr Unit B-08, Longboat Key, FL 34228
  • 3710 Gulf of Mexico Dr Unit G20, Longboat Key, FL 34228
    3710 Gulf of Mexico Dr Unit G20, Longboat Key, FL 34228
    3710 Gulf of Mexico Dr Unit G20, Longboat Key, FL 34228
    /39

    $349,900

    • 2 Beds
    • 2 Baths
    • 1,052 Sq Ft

    3710 Gulf of Mexico Dr Unit G20, Longboat Key, FL 34228

    WELCOME TO PARADISE! This unit epitomizes the perfect beach home. When you step through the front door, you will know that you have entered “House Beautiful”. The blend of colors and furnishings will make you feel that you are home. This home features a nice-sized living room, totally upgraded separate kitchen and dining room, two bathrooms and two bedrooms. This home has 1,052 sq. ft. of living

    Bill Shuttleworth EDGEWATER REAL ESTATE, INC

    3710 Gulf of Mexico Dr Unit G20, Longboat Key, FL 34228
  • 2600 Harbourside Dr Unit O-11, Longboat Key, FL 34228
    2600 Harbourside Dr Unit O-11, Longboat Key, FL 34228
    2600 Harbourside Dr Unit O-11, Longboat Key, FL 34228
    /18

    $239,000

    $36K PRICE DROP

    2600 Harbourside Dr Unit O-11, Longboat Key, FL 34228

    Easy Access for Docking your Boat! A 45 ft. x 22.5 ft. Boat Slip on the north side of O-dock pier at Longboat Key Moorings Marina. This slip requires Club membership. Unique set up inside the T-dock. Lots of space, and privacy. 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

    Jennifer Wilson LBRE LLC

    2600 Harbourside Dr Unit O-11, Longboat Key, FL 34228
  • 2600 Harbourside Dr Unit J-04, Longboat Key, FL 34228
    2600 Harbourside Dr Unit J-04, Longboat Key, FL 34228
    2600 Harbourside Dr Unit J-04, Longboat Key, FL 34228
    /14

    $350,000

    2600 Harbourside Dr Unit J-04, 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 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

    Jennifer Wilson LBRE LLC

    2600 Harbourside Dr Unit J-04, Longboat Key, FL 34228
  • 6750 Gulf of Mexico Dr Unit 152, Longboat Key, FL 34228
    6750 Gulf of Mexico Dr Unit 152, Longboat Key, FL 34228
    6750 Gulf of Mexico Dr Unit 152, Longboat Key, FL 34228
    /41

    $350,000

    $49K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 990 Sq Ft

    6750 Gulf of Mexico Dr Unit 152, Longboat Key, FL 34228

    Bring your boat!!! Excellent water views in this north end desirable Whitney Beach waterfront community.If you’ve been waiting for the perfect second-floor residence in the highly sought-after Whitney Beach community on Longboat Key, this is the one. Offering some of the finest views in the complex, this turn-key condominium has been thoughtfully upgraded and is move-in ready.What truly

    Amy Jones COASTAL KEY REALTY LLC

    6750 Gulf of Mexico Dr Unit 152, Longboat Key, FL 34228
  • 2600 Harbourside Dr Unit R-9, Longboat Key, FL 34228
    2600 Harbourside Dr Unit R-9, Longboat Key, FL 34228
    2600 Harbourside Dr Unit R-9, Longboat Key, FL 34228
    /26

    $335,000

    $44K PRICE DROP
    • 1,575 Sq Ft

    2600 Harbourside Dr Unit R-9, Longboat Key, FL 34228

    Embrace Unparalleled Elegance: Exquisite 75’ Boat Slip on Longboat Key’s premier R dock, Your Gateway to a Refined Gulf Coast Yachting Experience. Discover the pinnacle of luxury boating with this stunning 75’ x 21’ deep water boat slip, perfectly situated on the spectacular R dock at Longboat Key Club Moorings Marina, nestled along Florida’s breathtaking Gulf Coast. Slip R-9 offers unrivaled

    Mark J Baron COLDWELL BANKER REALTY

    2600 Harbourside Dr Unit R-9, Longboat Key, FL 34228

Showing Results 1 - 40, Page 1 of 2

Florida Manatee County Longboat Key

Real Estate & Homes in Longboat Key, FL under $500,000

Home Prices in Longboat Key, FL

The median home sale price in Longboat Key, FL is $1,000,000, down 19% year-over-year. Homes in Longboat Key sell in 107 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$1,000,000
Median Single Family Sale Price
$1,812,500
Median Townhouse Sale Price
$1,025,000
Median 2 Bedroom Sale Price
$749,900
Median 1 Bedroom Sale Price
$525,250
Average Price Per Sq Ft
$775
Number of Homes for Sale
366
Last 12 months Home Sales
465
Months of Supply
9.40
Median List Price
$1,107,500
Median Change From 1st List Price
11%
Median Home Sale Price YoY Change
-19%
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