Longboat Key, FL Homes

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  /53

  $2,495,000 Open Fri 10AM - 1PM

  • 3 Beds
  • 2 Baths
  • 2,311 Sq Ft

  500 Halyard Ln, Longboat Key, FL 34228

  Experience the best of waterfront living in this meticulously maintained Longboat Key home, perfectly positioned on an elevated large -acre lot for exceptional privacy and long open water views from nearly every room. This well-designed single story home boasts a split floor plan and sits on high ground and stayed dry and undamaged through the storms, providing for peace of mind and convenience

  Mike Seamon PREMIER SOTHEBYS INTL REALTY

  500 Halyard Ln, Longboat Key, FL 34228
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  /45

  $10,995 per month

  • 3 Beds
  • 2.5 Baths
  • 2,396 Sq Ft
  • House for Rent

  2339 Harbour Oaks Dr, Longboat Key, FL 34228

  Seasonal/short term rental on Longboat Key Beautifully renovated 3 bedroom 2 1/2 bathroom villa right on the golf course in prestigious, guard gated, Bay Isles. This spacious light filled delight has vaulted ceilings with sky lights, and new high impact windows and doors. The open floor plan is perfect for family time and entertaining. The kitchen is very large and has solid cherry wood

  Henry Rossi RENT SARASOTA

  2339 Harbour Oaks Dr, Longboat Key, FL 34228
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  /2

  $2,600,000 Sold Apr 15, 2025

  • 2,590 Sq Ft
  • $1004/SF
  • 20 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1996

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

  One or more photo(s) has been virtually staged. An exquisitely renovated & furnished penthouse with breathtaking beach views! A stunning corner residence offering an unparalleled experience directly along the pristine Gulf of America, with sweeping vistas of sugar sand beaches & shimmering azure waters. Enjoy the exclusive ambiance of a private beach house, surrounded by picturesque island views

  Candy Swick CANDY SWICK & COMPANY

  2185 Gulf of Mexico Dr Unit 245, Longboat Key, FL 34228
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  /36

  Est $733,055 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 642 Sq Ft

  225 Sands Point Rd Unit 6102, Longboat Key, FL 34228

  225 Sands Point Rd Unit 6102, Longboat Key, FL 34228
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  /65

  $995,000

  • 2 Beds
  • 2.5 Baths
  • 1,590 Sq Ft

  1900 Harbourside Dr Unit 102, Longboat Key, FL 34228

  Experience the best of Longboat Key living in this updated 2-bedroom, 2.5-bath townhouse in the exclusive Fairway Bay community, behind the gates of Bay Isles. Offering 1,590 square feet of well-designed living space, this home includes a deeded deep-draft boat slip handling boats up to 40 ft. with no bridges to the bay. The bright interior features light wood floors, recessed lighting, and

  Bruce Myer COLDWELL BANKER REALTY

  1900 Harbourside Dr Unit 102, Longboat Key, FL 34228
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  /25

  $9,500 per month

  • 3 Beds
  • 2 Baths
  • 2,141 Sq Ft
  • House for Rent

  691 Russell St, Longboat Key, FL 34228

  LONGBOAT KEY...This impeccable 3 bedroom, 2 bath home has been totally renovated. Open floor plan with oak plank flooring, updated recess lighting and hurricane windows and doors. Gorgeous kitchen with oversized quartz island, state of the art Kitchen Aid appliances. Immerse yourself in the backyard which features an 8' deep heated salt water pool, paver patio, high end artificial turf and fresh

  Teresa Ribaudo JENNETTE PROPERTIES INC

  691 Russell St, Longboat Key, FL 34228
• 

  /2

  $250,000 Sold Apr 15, 2025

  • 1,231 Sq Ft
  • $203/SF
  • 15 Days On Market

  • 1 Bed
  • 2 Baths
  • Built 1940

  690 Broadway St, Longboat Key, FL 34228

  This property has been STORM DAMAGED and requires complete demolition or reconstruction, and repair. Remediation has already been done. It is being sold AS IS, primarily for the land value. The property is vacant, flooded, and SOLD AS IS. This rare find is located in the heart of Longboat Key Village, within walking distance to the beach and just steps from the boat ramp and the Shore Restaurant

  Heidi Thompson STRINGER MANAGEMENT INC

  690 Broadway St, Longboat Key, FL 34228
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  /66

  Est $953,266 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft

  5201 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228

  5201 Gulf of Mexico Dr Unit 104, Longboat Key, FL 34228
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  /30

  $1,195,000

  • 2 Beds
  • 2 Baths
  • 1,827 Sq Ft

  1211 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228

  Discover this sunny coastal residence in the prestigious Promenade community. This two-bedroom residence spans more than 1,800 square feet, offering sweeping views of the Gulf of Mexico and lushly landscaped grounds. A sunset-facing terrace invites you to bask in gentle beach breezes while taking in breathtaking vistas of the sparkling water and tropical scenery. Step inside to an open-concept

  Roger Pettingell COLDWELL BANKER REALTY

  1211 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
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  /61

  $14,000 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. Like NEW, this beautifully designed three bedroom luxury residence has just completed a major updating remodeling with all new designer furniture and furnishings, new custom

  Patrice Ivan WAGNER REALTY

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

  $1,250,000 Sold Apr 15, 2025

  • 2,664 Sq Ft
  • $469/SF
  • 50 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1976

  541 Edlee Ln, Longboat Key, FL 34228

  PRICE IMPROVEMENT OF $100,000 – NOW $1,285,000Welcome to 541 Edlee Lane, a private Key West-inspired retreat tucked away on a quiet and secluded street in the heart of Longboat Key. Just a 6-minute walk to the pristine beaches and steps from your deeded boat launch into Sarasota Bay, this home offers an unparalleled blend of privacy, charm, and coastal convenience. Surrounded by lush

  Lisa Garcia COLDWELL BANKER REALTY

  541 Edlee Ln, Longboat Key, FL 34228
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  /52

  Est $829,883 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,561 Sq Ft

  4900 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  4900 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  /34

  $1,250,000

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft

  4835 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  Experience the ultimate beachfront lifestyle in this stunning 1,393 sq. ft. 2-bedroom, 2-bathroom retreat on Longboat Key. Perfectly positioned on the third floor, this home offers amazing views of the beautiful beaches and the endless Gulf horizon—visible from nearly every room! Wake up to the sound of waves in the master suite, where sliding doors open to a private balcony with breathtaking

  Donna Wrobel BERKSHIRE HATHAWAY HOMESERVICE

  4835 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
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  /29

  $3,800 per month

  • 2 Beds
  • 2 Baths
  • 1,194 Sq Ft
  • Condo for Rent

  450 Gulf of Mexico Dr Unit B302, Longboat Key, FL 34228

  For Rent! Furnished Annual! Step into this beautiful 2 bedroom 2 bathroom condo with pool & water view on Longboat Key. This unit offers the perfect island living from the open floor plan to the scenic view with bay breeze to the supreme location, only 2 miles from St Armand/Lido Key and just 5 miles to Downtown Sarasota. You will never run out of options for both fun and tranquil days! The

  Benjamin Dietrich ANCHOR DOWN REAL ESTATE

  450 Gulf of Mexico Dr Unit B302, Longboat Key, FL 34228
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  /2

  $1,585,000 Sold Apr 14, 2025

  • 1,155 Sq Ft
  • $1372/SF
  • 7 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1956

  3015 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228

  This is a unique opportunity to own one of only two residences in a condominium building that sits on its own private beach with 50 feet of water frontage. The condominium is comprised of the entire top floor of the building and exudes luxury and comfort. The home sustained no damage during 2024 storms, according to the owner. Only the first-floor garage was affected, and a new garage door and

  Michele Nesmith PREMIER SOTHEBYS INTL REALTY

  3015 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
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  /28

  Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 720 Sq Ft

  3710 Gulf of Mexico Dr Unit A19, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit A19, Longboat Key, FL 34228
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  /72

  $650,000

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft

  4800 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

  JAW-DROPPING WATER VIEWS! Revel & Relax as you experience amazing water views from every room of this inviting two-bedroom and two-bathroom condominium. Prepare to be enthralled by the mesmerizing beauty of the sparkling waters of Sarasota Bay, teaming with playful dolphins, graceful manatees, and the colorful spectacle of Florida's native birds. Witness spectacular sunrises, behold the

  Debby McCaig COLDWELL BANKER REALTY

  4800 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
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  /33

  $18,000 per month

  • 2 Beds
  • 2.5 Baths
  • 2,143 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228

  The Residences at The St. Regis Longboat Key offer an exceptional blend of ultra-luxury living and world-class resort amenities on the pristine shores of the Gulf of Mexico. This exclusive beachfront community features exquisitely designed residences with soaring ceilings, floor-to-ceiling glass doors, and panoramic sunrise-to-sunset views. The gourmet kitchen showcases Wolf and Sub-Zero

  Melissa Gissinger MICHAEL SAUNDERS & COMPANY

  1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
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  /2

  $3,050,000 Sold Apr 14, 2025

  • 2,590 Sq Ft
  • $1178/SF
  • 9 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1990

  535 Sanctuary Dr Unit B604, Longboat Key, FL 34228

  Set upon the pristine sandy shores of Longboat Key, you’ll find the Sanctuary. This community truly lives up to its name as it offers privacy, serenity, and luxury. Located behind the gates of the Longboat Key Club on the south end of the island, this community is sought after for good reason. This stunning 6th floor unit offers a floor plan that features both Gulf and Bay/ City views from the

  Drew Russell MICHAEL SAUNDERS & COMPANY

  535 Sanctuary Dr Unit B604, Longboat Key, FL 34228
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  /78

  Est $822,837 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,312 Sq Ft

  4600 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

  4600 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
• 

  

  /39

  $850,000

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

  2120 Harbourside Dr Unit 621, Longboat Key, FL 34228

  This beautifully updated 3-bedroom, 3.5-bath residence in the sought-after Atrium at Bay Isles on Longboat Key offers panoramic views of Sarasota Bay. The spacious living room opens to an expansive lanai through a 4-panel sliding glass door—perfect for seamless indoor-outdoor living.The contemporary kitchen is equipped with stainless steel appliances, granite countertops, abundant cabinetry, a

  Judy Mitchell PREMIER SOTHEBYS INTL REALTY

  2120 Harbourside Dr Unit 621, Longboat Key, FL 34228
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  /42

  $14,000 per month

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

  531 Birdie Ln, Longboat Key, FL 34228

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

  Karie Gorgone WAGNER REALTY

  531 Birdie Ln, Longboat Key, FL 34228
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  /2

  $310,000 Sold Apr 14, 2025

  • 1,008 Sq Ft
  • $308/SF
  • 89 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1972

  549 Sutton Place, Longboat Key, FL 34228

  Unparalleled Coastal Living – Affordable Luxury with Gulf to Bay Access! Presenting an extraordinary opportunity to own the lowest-priced 2-bedroom townhouse on Longboat Key, complete with a deeded covered garage—an unbeatable value in an exclusive setting. Situated in a pet-friendly community, this residence offers the ideal coastal lifestyle, whether you prefer relaxing on the pristine Gulf

  Malihe Karimi MICHAEL SAUNDERS & COMPANY

  549 Sutton Place, Longboat Key, FL 34228
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  /25

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 676 Sq Ft

  3710 Gulf of Mexico Dr Unit D22, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit D22, Longboat Key, FL 34228
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  /37

  $440,000

  • 1 Bed
  • 1 Bath
  • 861 Sq Ft

  3740 Gulf of Mexico Dr Unit 116, Longboat Key, FL 34228

  GULF TO BAY TWIN SHORES BEACH AND MARINA VILLAS. UNBELIEVABLE DIRECT BAYFRONT and MARINA VIEWS! COMPLETELY REMEDIATED AND ASSOCIATION INSURANCE FOR THE 8 VILLAS PAID IT ALL ( 100%). EVERYTHING NEW IN OCTOBER, 2025 FROM SHEETROCK, NEW SPECIAL FLOOD BARRIER SLIDER.($8000) APPLIANCES, UPGRADED NEW CABINETRY, 2 DOORS INCLUDING 4 POCKET DOORS, NEW A/C MINI SPLITS, HOTWATER HEATER, W/D AND LOVELY

  Marni Hayden CHROME REALTY LLC

  3740 Gulf of Mexico Dr Unit 116, Longboat Key, FL 34228
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  /60

  $3,500 per month

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

  3810 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  1-bed, 1-bath 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 community

  Dakota Magnus FLORIDA GALLERY REAL ESTATE

  3810 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
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  /2

  $900,000 Sold Apr 09, 2025

  • 1,393 Sq Ft
  • $646/SF
  • 74 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  4825 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

  THE SELLER IS SERIOUS! PRICE REDUCTION OF $175,000. This price reduction certainly makes this unit a fantastic buy for the snowbirder or even the full-timer who wants to spend days and days staring at the beautiful sunsets over the Gulf of Mexico. These are breathtaking full views of the Gulf of Mexico, with pristine white sand beaches stretching endlessly before you. This dream can be yours with

  Carolyn Codella WAGNER REALTY

  4825 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
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  /56

  Est $707,227 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 642 Sq Ft

  225 Sands Point Rd Unit 7304, Longboat Key, FL 34228

  225 Sands Point Rd Unit 7304, Longboat Key, FL 34228
• 

  

  /46

  $1,890,000

  • 4 Beds
  • 2.5 Baths
  • 2,248 Sq Ft

  588 Bayview Dr, Longboat Key, FL 34228

  It is time to build your dream home in the best location in Longboat Key. This 100 ft of waterfront looks directly at the estuary across from the house. Located on the canal that leads you into the Intracoastal waterway and the Gulf of America. You're just a block or so to the most beautiful beach in Longboat Key. Longboat Key has

  Deborah Marcum EQUITY CONSULTANTS INC

  588 Bayview Dr, Longboat Key, FL 34228
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  /12

  $32,000 per month

  • 1 Bed
  • 1.5 Baths
  • 1,684 Sq Ft
  • Condo for Rent

  1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228

  Enter the unit from a private elevator which features a spacious, open-plan living area with large windows allowing natural light and incredible views of the surrounding landscape and Sarasota Bay. The lavish living space opens up onto a stunning balcony that overlooks Sarasota Bay and the St. Regis grounds and includes a gas grill. The stylish living area includes high-end furniture with a

  Larry Starr SVN COMMERCIAL ADVISORY GROUP

  1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
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  /2

  $510,000 Sold Apr 08, 2025

  • 1,440 Sq Ft
  • $354/SF
  • 27 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1988

  611 Cedars Ct, Longboat Key, FL 34228

  Come paint your masterpiece, your blank canvas has arrived. ORIGINAL Owner has lightly used and loved this property from the beginning. This is a beautiful Townhome in Cedars East Fitness & Tennis Resort. Mere steps away from the world famous White Sand and Turquoise waters of Longboat Key. Ideally, it is located in a prime location of Cedars East providing easy access to the community's first

  Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

  611 Cedars Ct, Longboat Key, FL 34228
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  /51

  Est $318,344 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 741 Sq Ft

  104 Twin Shores Blvd, Longboat Key, FL 34228

  104 Twin Shores Blvd, Longboat Key, FL 34228
• 

  

  /28

  $349,900

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft

  3806 Gulf of Mexico Dr Unit C311, Longboat Key, FL 34228

  Priced to sell! Discover the perfect blend of comfort and coastal living in this beautifully updated 2-bedroom, 2-bathroom condominium, ideally situated steps away from the pristine sands of the Gulf of Mexico. This luxurious Long Boat Key condo comes completely furnished and features an open-concept design with a fully equipped kitchen, ideal for both relaxation and entertaining. This

  Michael Fyvie KW COASTAL LIVING II

  3806 Gulf of Mexico Dr Unit C311, Longboat Key, FL 34228
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  /53

  $4,200 per month

  • 2 Beds
  • 2 Baths
  • 1,640 Sq Ft
  • Condo for Rent

  840 Bayport Way Unit 840, Longboat Key, FL 34228

  This stunningly appointed ground floor 2-bedroom 2 bath condo with lots of open living space is the ideal place to spend your summer vacation. Relax on screened lanai and enjoy the gentle breezes of this tropical oasis. Situated between Sarasota Bay and the Gulf of Mexico and surrounded by lush landscaping, you will truly find the private patio a great place to spend your afternoons. The

  Shirley Cuddy REALTY SERVICES INC

  840 Bayport Way Unit 840, Longboat Key, FL 34228
• 

  /2

  $362,500 Sold Apr 08, 2025

  • 1,007 Sq Ft
  • $360/SF
  • 107 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  3808 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. OPPORTUNITY IS KNOCKING...$20,000 Price Reduction plus the 2025 monthly HOA fees have been prepaid in full! This beautifully renovated 2-Bedroom, 2-Bathroom Condo at Beach Harbor Club on Longboat Key offers partial Gulf and Pool views in a bright, inviting setting—all at an affordable price! Every room showcases 2023/2024 updates plus tranquil views

  Eileen Gillen COLDWELL BANKER REALTY

  3808 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
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  /42

  Est $386,586 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 809 Sq Ft

  102 Twin Shores Blvd, Longboat Key, FL 34228

  102 Twin Shores Blvd, Longboat Key, FL 34228
• 

  

  /40

  $999,999

  • 4 Beds
  • 3 Baths
  • 1,792 Sq Ft

  578-580 Companion Way, Longboat Key, FL 34228

  Seasonal Income Awaits - Turnkey Duplex in the Heart of Longboat Key'Tis the season for a lucrative investment! This fully renovated duplex in the heart of Longboat Key offers the perfect blend of income potential and coastal charm. Featuring two separate units, each with 2 bedrooms and 2 bathrooms, this property is sold fully turnkey, so you can start generating rental income immediately.Step

  Inbal August DOUGLAS ELLIMAN

  578-580 Companion Way, Longboat Key, FL 34228
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  /43

  $8,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,751 Sq Ft
  • House for Rent

  569 Rountree Dr, Longboat Key, FL 34228

  Fabulous turnkey rental open for off-season. This European-styled home will surpass all your needs – whether you’re remodeling, relocating or simply need vacation time! Featuring three bedrooms, three ensuite baths, this 2-story home, boasts two lanai’s with seating, outdoor kitchen, a roof-top sun deck and sparkling heated lap pool. Upon entering the home, you’ll enjoy the bottom floor expanse

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  569 Rountree Dr, Longboat Key, FL 34228
• 

  /2

  $605,000 Sold Apr 07, 2025

  • 1,590 Sq Ft
  • $381/SF
  • 14 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1982

  1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228

  Welcome to an exceptional townhome in the prestigious Fairway Bay community on Longboat Key, where luxury and resort-style living come together seamlessly. This FURNISHED, beautifully updated 2-bedroom, 2.5-bathroom residence features an open-concept design with soaring vaulted ceilings, transom windows, and a cozy fireplace. The gourmet kitchen boasts light-colored cabinetry, granite countertops

  Bruce Myer COLDWELL BANKER REALTY

  1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228
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  /60

  Est $836,921 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,523 Sq Ft

  4960 Gulf of Mexico Dr Unit 306, Longboat Key, FL 34228

  4960 Gulf of Mexico Dr Unit 306, Longboat Key, FL 34228

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