11,516

Longboat Key, FL Homes

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  • /48

    $700,000

    • 2 Beds
    • 2 Baths
    • 1,484 Sq Ft

    5055 Gulf of Mexico Dr Unit 435, Longboat Key, FL 34228

    Gulf water views from back deck in this open concept 2-Bedroom, 2-Bathroom Condo at Club Longboat Beach & Tennis is A Perfect Longboat Key Retreat offers an expansive 1,484 SqFt of thoughtfully designed living space, this condo combines comfort, convenience, and a balcony help you unwind and enjoy the fresh coastal air. As a well-maintained residence, this home offers a welcoming, move-in ready

    Amy Jones COASTAL KEY REALTY LLC

    5055 Gulf of Mexico Dr Unit 435, Longboat Key, FL 34228
  • /30

    $9,721 per month

    • 2 Beds
    • 2 Baths
    • 1,461 Sq Ft
    • Condo for Rent

    2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228

    short stories AVAILABLE NOW... Stunning 2 bedroom 2 bath Longboat Key Gulf front condo with direct sweeping view of the Gulf of Mexico. Every evening enjoy breathtaking sunsets on your private balcony. Start your day with a leisurely stroll on the soft sand beach or take a refreshing dip in the pool. This condo is beautifully furnished and professionally decorated. King size bed in both

    Gerald Cunningham KELLER WILLIAMS ON THE WATER S

    2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228
  • /37

    $765,000 Sold Mar 13, 2025

    • 1,276 Sq Ft
    • $600/SF
    • 7 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1995

    3070 Grand Bay Blvd Unit 625, Longboat Key, FL 34228

    One or more photo(s) has been virtually staged. WORRY-FREE Coastal Living with HURRICANE SHUTTERS. This 2-bedroom, 2-bathroom unit offers DIRECT SARASOTA BAY AND GOLF COURSE VIEWS, with SPECTACULAR SUNRISES each morning and the twinkling lights of Downtown Sarasota by night. Located in the PET-FRIENDLY (both large and small) Grand Bay community on Longboat Key. FLOOR TO CEILING GLASS SLIDERS

    Lee Mirman INVESTMENTS IN SARASOTA

    3070 Grand Bay Blvd Unit 625, Longboat Key, FL 34228
    • /45

      Est $5,617,180 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,640 Sq Ft

      4765 Gulf of Mexico Dr Unit C301, Longboat Key, FL 34228

      4765 Gulf of Mexico Dr Unit C301, Longboat Key, FL 34228
  • /94

    $1,399,000

    • 2 Beds
    • 2 Baths
    • 1,409 Sq Ft

    1050 Longboat Club Rd Unit 903, Longboat Key, FL 34228

    This TOTALLY RENOVATED ISLAND BEAUTY will charm the most sophisticated Buyers and the spectacular sunrise views over Sarasota Bay enhanced by sunset-lit City and Golf Course views will take your breath away. Ideally situated within a short beach walk between the popular Resort at Longboat Key Club and the brand-new St. Regis Resort, this perfect gem features storm shutters PLUS impact-rated

    Tina Rudek Stark, PA ROSEBAY INTERNATIONAL REALTY, INC

    1050 Longboat Club Rd Unit 903, Longboat Key, FL 34228
  • /48

    $11,900 per month

    • 3 Beds
    • 2 Baths
    • 1,731 Sq Ft
    • Condo for Rent

    5621 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228

    Available February 2025. Looking for a vacation in warm sunny Florida in a condo where you walk directly out onto the deck directly onto the beach? Stay in this 3 bedroom (2 king beds/1 queen), 2 bath condo in Salty Acres with 2 covered parking spaces. It is on the Gulf Side beach with amazing views. Condo is beautiful and recently remodeled. It must be a monthly rental. $6,950 a month April -

    William Glade WILLIAM GLADE LIC. REAL ESTATE BROKER

    5621 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228
  • /15

    $425,000 Sold Mar 12, 2025

    • 66 Days On Market
    • Built 1985

    2600 Harbourside Dr Unit L-10, Longboat Key, FL 34228

    82 ft x 26 ft Boat Slip on L-dock at Longboat Key Moorings Marina for sale. Exceptional views of Sarasota Bay and the city skyline from atop your flybridge. 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 that includes

    Jennifer Wilson LBRE LLC

    2600 Harbourside Dr Unit L-10, Longboat Key, FL 34228
    • /37

      Est $312,373 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 712 Sq Ft

      3806 Gulf of Mexico Dr Unit C308, Longboat Key, FL 34228

      3806 Gulf of Mexico Dr Unit C308, Longboat Key, FL 34228
  • /55

    $3,150,000

    • 3 Beds
    • 4 Baths
    • 3,054 Sq Ft

    1281 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228

    Introducing an exceptional beachfront residence that redefines luxury living on Longboat Key, offering panoramic seventh-floor views that span from the Gulf of Mexico to Sarasota Bay. This beautifully furnished three-bedroom, four-bath retreat encompasses over 3,000 square feet under air and delivers an unparalleled coastal lifestyle. The expansive great room is elegant and versatile, featuring a

    Jo Rutstein PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1281 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228
  • /38

    $10,400 per month

    • 3 Beds
    • 3 Baths
    • 1,744 Sq Ft
    • House for Rent

    2823 Gulf of Mexico Dr, Longboat Key, FL 34228

    Welcome to beachfront paradise on Longboat Key! This rare opportunity offers the best of coastal living with spectacular views of the coastline! Nestled along the shores of the Gulf of Mexico, this three bedroom, three bathroom home invites you to enjoy the ultimate beachfront experience. This is the perfect property for relaxing, soaking up the sun, enjoying breathtaking sunsets, and savoring

    Michael Cella DALTON WADE INC

    2823 Gulf of Mexico Dr, Longboat Key, FL 34228
  • /44

    $470,000 Sold Mar 11, 2025

    • 1,260 Sq Ft
    • $373/SF
    • 95 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1981

    806 Bayport Way Unit 806, Longboat Key, FL 34228

    Welcome to your serene retreat in Bayport, where elegant design meets the tranquility of nature. This thoughtfully designed first-floor corner condo stands resiliently with no history of flooding from storms and features 2 spacious bedrooms and 2 baths, including an updated kitchen and a refreshed guest bath. The unit boasts a private outdoor courtyard perfect for morning coffee and a sunroom

    April Green DUNCAN REAL ESTATE, INC.

    806 Bayport Way Unit 806, Longboat Key, FL 34228
    • /19

      Est $352,444 Not Listed For Sale

      • Studio
      • 1,820 Sq Ft

      2800 Harbourside Dr Unit D-13, Longboat Key, FL 34228

      2800 Harbourside Dr Unit D-13, Longboat Key, FL 34228
  • /80

    $2,098,000

    • 3 Beds
    • 3 Baths
    • 2,550 Sq Ft

    3030 Grand Bay Blvd Unit 324, Longboat Key, FL 34228

    Be wowed by this totally renovated Cayman unit in coveted building 3 of Grand Bay. Savor the mesmerizing full Sarasota Bay views with Sarasota downtown in the distance, highlighted by the boats arriving in the Marina and the beautiful grounds of the Longboat Key Club 9th hole of the Blue course. Discerning buyers will appreciate the quality and attention to detail evident in this must-see

    Maureen Horn MICHAEL SAUNDERS & COMPANY

    3030 Grand Bay Blvd Unit 324, Longboat Key, FL 34228
  • /66

    $8,000 per month

    • 3 Beds
    • 3 Baths
    • 2,100 Sq Ft
    • Condo for Rent

    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

    Prime location... This absolutely gorgeous fully furnished condo located in the Promenade Longboat Key with breathtaking water views from every room. It offers 2 bedroom/den/2 bathroom. The master bedroom features a king-size bed, elegant master bath separate bathtub, shower and a vidette for your convenience. For your guests the second bedroom offers 2 twin beds that can convert into a

    Elsie Salazar BERKSHIRE HATHAWAY HOMESERVICE

    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
  • /48

    $1,170,000 Sold Mar 11, 2025

    • 1,393 Sq Ft
    • $840/SF
    • 94 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1970

    4825 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

    Nestled along the Gulf of Mexico’s pristine shores, this expertly renovated 2-bedroom, 2-bath residence offers an unparalleled living experience with breathtaking, unobstructed views from every room. Located on the third floor, this exquisite condo was not impacted by recent hurricanes, ensuring peace of mind for its new owners. Upon entry, you are immediately greeted by stunning, panoramic views

    Michael Albano, PA COLDWELL BANKER REALTY

    4825 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    • /79

      Est $422,041 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 976 Sq Ft

      3810 Gulf of Mexico Dr Unit F102, Longboat Key, FL 34228

      3810 Gulf of Mexico Dr Unit F102, Longboat Key, FL 34228
  • /53

    $2,749,900

    • 3 Beds
    • 2.5 Baths
    • 2,580 Sq Ft

    535 Sanctuary Dr Unit A602, Longboat Key, FL 34228

    Welcome to paradise! This 3 bedroom floor plan offers Northwest and Southeast terraces boasting direct beach and sunset views from the great room and primary suite along with City and Bay views from the kitchen, den and guest bedroom. Floor to ceiling sliders showcase the big views at both ends and provide a bright welcoming atmosphere. The kitchen features a large center island, breakfast nook,

    Ian Addy, PA MICHAEL SAUNDERS & COMPANY

    535 Sanctuary Dr Unit A602, 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

    ***NEW VACATION RENTAL LISTING** Rented for Season 2025 February through April 20th.* Welcome to your amazing beachfront Longboat Key at Sunset Beach vacation. Sunset Beach is a 3 building complex located directly on Gulf of Mexico and it's powdery sandy beach and perfect sunset views. Guests will find a large gulf front pool, spa, community room for social gatherings, fire pit and BBQ grill.

    Jennifer LeBlanc PRECISE REALTY CORP

    2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228
  • /32

    $560,000 Sold Mar 11, 2025

    • 642 Sq Ft
    • $872/SF
    • 175 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1983

    225 Sands Point Rd Unit 6103, Longboat Key, FL 34228

    Enjoy peaceful lagoon views from this first floor Junior Suite in Building 6. Unlike the other floors, the first floor Junior Suites in this building have 10' ceilings making it feel especially spacious while optimizing natural light and view. It is typical to see manatees, dolphins, paddleboarders and a variety of tropical birds from the terrace overlooking the lagoon. Building 6 offers extra

    Ian Addy, PA MICHAEL SAUNDERS & COMPANY

    225 Sands Point Rd Unit 6103, Longboat Key, FL 34228
    • /42

      Est $452,021 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 882 Sq Ft

      781 Saint Judes Dr N Unit B, Longboat Key, FL 34228

      781 Saint Judes Dr N Unit B, Longboat Key, FL 34228
  • /52

    $1,950,000

    • 3 Beds
    • 2.5 Baths
    • 2,375 Sq Ft

    545 Sanctuary Dr Unit B806, Longboat Key, FL 34228

    Welcome to luxury living at The Sanctuary located behind the gates of the Longboat Key Club on south Longboat Key! Whether you're looking for a peaceful retreat or a permanent residence, this 3 bedroom, 2 1/2 bath beachfront paradise has it all. The massive views of Sarasota Bay, the downtown city skyline and manicured golf course greens are front and center from the moment you step across the

    Ian Addy, PA MICHAEL SAUNDERS & COMPANY

    545 Sanctuary Dr Unit B806, Longboat Key, FL 34228
  • /40

    $5,500 per month

    • 3 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
  • /65

    $1,195,000 Sold Mar 10, 2025

    • 2,555 Sq Ft
    • $468/SF
    • 30 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1988

    3427 Winding Oaks Dr Unit 14, Longboat Key, FL 34228

    Experience the pinnacle of waterfront luxury in this meticulously updated 3-bedroom, 3-bath villa overlooking the Blue Heron Harbourside Golf Course in the exclusive Winding Oaks community on Longboat Key. Combining the privacy of a single-family home with maintenance-free living, this residence offers panoramic water and Blue 5th-hole views in a sophisticated modern setting. The open floor plan

    Bruce Myer COLDWELL BANKER REALTY

    3427 Winding Oaks Dr Unit 14, Longboat Key, FL 34228
    • /27

      Est $1,068,189 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,314 Sq Ft

      4401 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228

      4401 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228
  • /75

    $5,499,000

    • 3 Beds
    • 2.5 Baths
    • 3,060 Sq Ft

    2333 Gulf of Mexico Dr Unit 1A2, Longboat Key, FL 34228

    Luxury Beachfront Condo – Fully Renovated -Experience the epitome of coastal luxury in this fully renovated beachfront condominium. This spacious residence boasts 3 bedrooms, 3 bathrooms, and over 3,000 sq ft of refined interior living space with high-end finishes. An expansive 1,000 sq ft wraparound balcony complete with a built-in outdoor kitchen offers breathtaking ocean views and the

    Gigi Silverberg DOUGLAS ELLIMAN

    2333 Gulf of Mexico Dr Unit 1A2, Longboat Key, FL 34228
  • /16

    $6,000 per month

    • 2 Beds
    • 2 Baths
    • 1,257 Sq Ft
    • Condo for Rent

    Unlisted Address

    SEAPLACE on LONGBOAT KEY. Relax and spend your winter days at this tropical seaside paradise. This pretty two bedroom condominium is well appointed with a king size bed in the master suite. Master bathroom has a walk in shower. SEAPLACE has all the amenities. to enjoy your stay: Two swimming pools, tennis courts, fitness center, clubhouse, and the most amazing beach on LBK. Just minutes to ST

    Jane Hunter JENNETTE PROPERTIES INC

    Unlisted Address
  • /28

    $725,000 Sold Mar 10, 2025

    • Land
    • 0.23 Acre
    • $3,152,174 per Acre
    • 52 Days On Market

    561 Gulf Bay Rd, Longboat Key, FL 34228

    Build your dream home on one of Longboat Key's remaining gems. Ideally between the charm of Anna Maria Island and sophistication of St. Armands Circle, this rare vacant lot offers an unparalleled opportunity to create your custom coastal retreat on Longboat Key. Alongside the serene Joan Durante Park nature preserve, this exceptional property boasts privacy and natural beauty in abundance. With

    Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

    561 Gulf Bay Rd, Longboat Key, FL 34228
    • /69

      Est $384,575 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 912 Sq Ft

      4760 Gulf of Mexico Dr Unit Villa 7, Longboat Key, FL 34228

      4760 Gulf of Mexico Dr Unit Villa 7, Longboat Key, FL 34228
  • /31

    $115,000

    • 1 Bed
    • 1 Bath
    • 640 Sq Ft

    96 Main Street Dr, Longboat Key, FL 34228

    Location! Location! And excellent value. Live in paradise on Longboat Key with the Bay and Marina on one side and the beach/gulf on the other side. Deeded beach access and private marina with 16 boat slips. This property is being sold as-is and is offered well below its taxable land value. I have done the homework for you to add a new modular home, elevated to approximately 9 feet with potential

    Sharon Austin PREMIER SOTHEBY'S INTERNATIONAL REALTY

    96 Main Street Dr, Longboat Key, FL 34228
  • /47

    $5,000 per month

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Condo for Rent

    3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228

    VACATION RENTAL!!! Spacious 6th floor condo awaits your arrival! This lovely 2 Bedroom, 2 Bath condo is inviting and warm and features an updated kitchen with granite counter tops and appliances. Stunning views await you from most rooms! This bright and airy unit provides views of Buttonwood Bayou and Sarasota Bay whether you're sitting inside or relaxing on your beautiful private balcony. The

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228
  • /2

    $1,255,000 Sold Mar 07, 2025

    • 1,458 Sq Ft
    • $861/SF
    • 26 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1970

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

    One or more photo(s) has been virtually staged. Discover the ultimate in beachfront living with this inviting 2-bedroom, 2-bathroom residence in Longboat Key Towers. Nestled behind the gates of the prestigious Longboat Key Club, this home offers sweeping Gulf views from its west-facing living areas and serene sunrise vistas from its east-facing bedrooms. Designed for comfort and relaxation, the

    Bruce Myer COLDWELL BANKER REALTY

    603 Longboat Club Rd Unit 903N, Longboat Key, FL 34228
    • /19

      Not Listed For Sale

      • 900 Sq Ft

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

      2600 Harbourside Dr Unit Q-08, Longboat Key, FL 34228
  • /13

    $700,000

    • Land
    • 0.14 Acre
    • $5,000,000 per Acre

    2929 Pyrula Dr, Longboat Key, FL 34228

    Build your dream home on this exceptional vacant lot located in the heart of Longboat Key. Nestled midway on the island, this rare offering includes deeded beach access just a short stroll away, allowing you to enjoy the pristine Gulf shores at your leisure.Perfectly positioned for both privacy and convenience, the property is just moments from the upscale shopping and dining of St.

    Zain Hartman HARTMAN REAL ESTATE & COMPANY

    2929 Pyrula Dr, Longboat Key, FL 34228
  • /99

    $7,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,424 Sq Ft
    • House for Rent

    2369 Harbour Oaks Dr, Longboat Key, FL 34228

    LIVE THE LIFE ON LONGBOAT KEY...in this three bedroom, two-and-a-half bathroom villa in the BAY ISLES gated community. Open floor plan, with vaulted ceilings, hardwood floors throughout. Private screened in pool with a view of the golf course and evening sunsets with plenty of space for entertaining. Kitchen is equipped with everything a cook would need including a separate wet bar with a

    Teresa Ribaudo JENNETTE PROPERTIES INC

    2369 Harbour Oaks Dr, Longboat Key, FL 34228
  • /2

    $795,000 Sold Mar 06, 2025

    • 1,265 Sq Ft
    • $628/SF
    • 1 Day On Market
    • 2 Beds
    • 2 Baths
    • Built 1978

    1945 Gulf of Mexico Dr Unit M2313, Longboat Key, FL 34228

    Modern Elegance in a Prime Longboat Key LocationStep into this exquisite, move-in-ready condo that effortlessly blends modern design, functionality, and unparalleled comfort. Situated in a coveted Longboat Key location, this residence is ideal for those seeking for coastal lifestyle.Wake up to views of the Gulf’s shimmering waters and unwind with spectacular sunsets from your living room

    Michael Renick MANGROVE REALTY ASSOCIATES

    1945 Gulf of Mexico Dr Unit M2313, Longboat Key, FL 34228
    • /47

      Est $1,425,739 Not Listed For Sale

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

      1135 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

      1135 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
  • /39

    $639,000

    • 2 Beds
    • 2 Baths
    • 1,148 Sq Ft

    605 Sutton Place Unit 401, Longboat Key, FL 34228

    Welcome to your dream coastal retreat with AMAZING views. This beautifully remodeled top floor, end unit condo offers unparalleled views, luxury and comfort. Offered fully furnished. This premium unit features 2 spacious bedrooms, 2 modern bathrooms and elegant luxury vinyl flooring throughout. Step into a bright and open living space, where large sliding glass doors lead to an expansive

    Stacey Hart PREFERRED SHORE LLC

    605 Sutton Place Unit 401, Longboat Key, FL 34228
  • /31

    $5,000 per month

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

    1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228

    AVAILABLE RENTAL APRIL 1, 2025 through MAY 30,2026 Located the furthest South Behind The Gates of Longboat Key Club. Privateer North Complex located o Gulf of Mexico. Only a few steps to the beach. This 2 bedroom 2 bath residence has everything you need. Beautiful full Bay from this 8th floor residence. Views from all windows and from the outdoor patio a great view of of the Gulf. Split bedroom

    Marni Hayden CHROME REALTY LLC

    1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
  • /2

    $1,040,000 Sold Mar 06, 2025

    • 1,819 Sq Ft
    • $572/SF
    • 50 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1981

    1065 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228

    Discover the ultimate island living at Beachplace, a sought-after condominium community on the serene shores of Longboat Key. This rarely available three-bedroom, two-bath corner residence, Unit #105, in the desired Building 10, is offered turnkey furnished included in the purchase price and ready for your immediate enjoyment or as an ideal investment property. This move-in-ready, south-facing,

    Moriah Taliaferro PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1065 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228
    • /18

      Est $257,735 Not Listed For Sale

      • Studio

      2600 Harbourside Dr Unit K-01, Longboat Key, FL 34228

      2600 Harbourside Dr Unit K-01, Longboat Key, FL 34228

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