Longboat Key, FL Homes

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  /62

  $2,700,000

  • 4 Beds
  • 3 Baths
  • 3,252 Sq Ft

  2282 Harbour Court Dr, Longboat Key, FL 34228

  Welcome to Harbour Court, a secluded haven nestled within a private enclave of just 18 distinguished residences, behind the gates in Bay Isles. Set amidst lush tropical gardens, the home boasts direct Bayfront views and private sailboat water access right outside your door. Whether you're setting sail from your personal dock or enjoying the community’s resort-style amenities—like the serene pool,

  Ann Martin MICHAEL SAUNDERS & COMPANY

  2282 Harbour Court Dr, Longboat Key, FL 34228
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  /62

  $8,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,143 Sq Ft
  • Condo for Rent

  3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228

  Luxury Seasonal or Annual Rental in Luxurious Grand Bay Community – Longboat KeyExperience unparalleled luxury and breathtaking views from this stunning 9th-floor condominium at Grand Bay. From sunrise to sunset, enjoy panoramic vistas from your private wraparound balcony or through the floor-to-ceiling sliding glass doors that frame the living room. Designed for both relaxation and

  Alyssa Cromie NEXTHOME EXCELLENCE

  3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228
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  /2

  $1,600,000 Sold May 09, 2025

  • 2,148 Sq Ft
  • $745/SF
  • 36 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1988

  581 Broadway St, Longboat Key, FL 34228

  Buyer Opportunity! New price on this stunning furnished three-bedroom elevated retreat in the charming and historic Longbeach Village. Coastal elegance meets modern luxury in this thoughtfully designed and updated home. A blend of timeless charm and contemporary sophistication welcomes you into a warm and inviting living space. The vaulted great room is a showstopper, featuring exposed beams,

  Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  581 Broadway St, Longboat Key, FL 34228
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  /53

  Est $790,801 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 642 Sq Ft

  225 Sands Point Rd Unit 6106, Longboat Key, FL 34228

  225 Sands Point Rd Unit 6106, Longboat Key, FL 34228
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  /49

  $939,000

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft

  1095 Gulf of Mexico Dr Unit 503, Longboat Key, FL 34228

  Enjoy comfortable, coastal living in this well-appointed 2BR/2BA residence on the sought-after south end of Longboat Key. With over 1,500 sq. ft., this home features a neutral color palette and thoughtful design that enhances the natural beauty just outside. The kitchen offers classic white cabinetry with glass accents, granite countertops, stainless-steel appliances, and recessed lighting. A

  Bruce Myer COLDWELL BANKER REALTY

  1095 Gulf of Mexico Dr Unit 503, Longboat Key, FL 34228
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  /20

  $15,500 per month

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

  1211 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228

  Special offer!Get $2000 (total) off for leases of 4+ months.Amazing Gulf front location in Longboat Key (LBK), FloridaThis two bedroom, 2 1/2 Bath condo (plus pull-out couch) is completely renovated and remodeled. All brand-new furnishings, appliances, counters, cabinets, cookware, linens, etc. This ninth-floor unit at the luxurious Promenade offers the best of everything.

  Natasha Shevchuk 1ST PREMIER INTL PROPERTIES

  1211 Gulf of Mexico Dr Unit 906, Longboat Key, FL 34228
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  /2

  $10,250,000 Sold May 09, 2025

  • 6,923 Sq Ft
  • $1481/SF
  • 76 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 1993

  801 Longboat Club Rd, Longboat Key, FL 34228

  Welcome to a truly remarkable legacy estate spanning 150’ of walking beach tucked behind the gates of the exclusive Longboat Key Club in Regent’s Court. Unquestionably, one of the area’s most distinguished and desirable locations. Perfectly positioned on a quiet street, this custom built residence offers unparalleled views of the Gulf of Mexico, lush tropical landscaping, and is designed for the

  Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  801 Longboat Club Rd, Longboat Key, FL 34228
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  /31

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 621 Sq Ft

  3710 Gulf of Mexico Dr Unit C24, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit C24, Longboat Key, FL 34228
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  /53

  $1,050,000

  • 2 Beds
  • 2 Baths
  • 1,170 Sq Ft

  6951 Gulf of Mexico Dr Unit 14, Longboat Key, FL 34228

  WOW! The minute you open the front door of this first floor Coastal Retreat Seaside condo, you will be captivated by the shimmering, turquoise Gulf of Mexico Water View and the Panoramic Sandy White Beach in front of you. You'll be eager to get a closer look from the glassed in Florida Room, so you may overlook the beauty of this updated, attractively furnished & decorated first floor residence

  Maruta Miluns MICHAEL SAUNDERS & COMPANY

  6951 Gulf of Mexico Dr Unit 14, Longboat Key, FL 34228
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  /48

  $11,000 per month

  • 3 Beds
  • 2 Baths
  • 1,861 Sq Ft
  • House for Rent

  512 Gunwale Ln, Longboat Key, FL 34228

  Location, location, location. This furnished rental offers the perfect blend of convenience and waterfront living. Enjoy direct access to the Gulf of Mexico with a private dock and boat lift, take a walk on the pristine white sand beaches or relax and unwind in the pool. Nestled in a prime location just minutes from St. Armands Circle, you'll have access to the best dining, shopping and

  Marcia Benson Berkshire Hathaway Florida Realty

  512 Gunwale Ln, Longboat Key, FL 34228
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  /60

  $2,500,000 Sold May 09, 2025

  • 4,858 Sq Ft
  • $515/SF
  • 121 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2008

  591 Putting Green Ln, Longboat Key, FL 34228

  Welcome to the coastal sanctuary you've been dreaming of—perfectly nestled on a peaceful cul-de-sac in one of Longboat Key’s most coveted communities, Country Club Shores. Set on an oversized, lushly landscaped lot, this elegant waterfront residence offers mesmerizing Sarasota Bay views and a front-row seat to the city skyline, all from the comfort of home. Step inside and immediately feel the

  Roberta&Carolyn Tengerdy & Collins PREMIER SOTHEBY'S INTERNATIONAL REALTY

  591 Putting Green Ln, Longboat Key, FL 34228
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  /8

  Est $620,912 Not Listed For Sale

  6800 Longboat Dr S, Longboat Key, FL 34228

  6800 Longboat Dr S, Longboat Key, FL 34228
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  /33

  $2,625,000

  • 3 Beds
  • 2.5 Baths
  • 2,269 Sq Ft

  781 Binnacle Point Dr, Longboat Key, FL 34228

  This house had no flooding after major hurricanes of 2024 due to its high elevation and hurricane resistant doors and windows.  Assumable loan available. Coveted lifestyle and location in Emerald Harbor on one of the widest canals on Longboat Key with direct access to Sarasota Bay with no bridges. Move in ready and fully furnished. New roof 2024, new heat pump and spa 2023 and outdoor pool/lanai

  Sinan Zakaria LISTED SIMPLY

  781 Binnacle Point Dr, Longboat Key, FL 34228
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  /22

  $9,500 per month

  • 2 Beds
  • 2 Baths
  • 1,346 Sq Ft
  • Condo for Rent

  5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228

  AVAILABLE MARCH 2025 - APRIL 10 $7,000 30 day lease. Looking for a Beach front vacation in warm sunny Florida in a condo where you walk out onto the deck and directly onto the beach? Stay in this 2 bedroom , 2 bath condo in Salty Acres with 2 parking spaces. It is on the Gulf Side beach with amazing views. Condo is beautiful and is in excellent condition. It must be a monthly rental. $6,950 a

  William Glade WILLIAM GLADE LIC. REAL ESTATE BROKER

  5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
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  /2

  $124,000 Sold May 08, 2025

  • 935 Sq Ft
  • $133/SF
  • 150 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1965

  83 Main Street Dr, Longboat Key, FL 34228

  Location, location location! This storm impacted mobile home is your opportunity to own a slice of paradise with PRIVATE BEACH ACCESS, MARINA ACCESS, and community saltwater pool and more. Ready to enjoy million dollar sunsets without the typical million dollar Longboat Key price tag? Twin Shores is a secret gem of Longboat Key- the community spans from the Gulf to the Bay. Priced well below

  Erica Smentowski KELLER WILLIAMS ON THE WATER S

  83 Main Street Dr, Longboat Key, FL 34228
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  /45

  Est $1,520,118 Not Listed For Sale

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

  1055 Gulf of Mexico Dr Unit 601, Longboat Key, FL 34228

  1055 Gulf of Mexico Dr Unit 601, Longboat Key, FL 34228
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  /48

  $1,100,000

  • 2 Beds
  • 2 Baths
  • 1,585 Sq Ft

  1211 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228

  Welcome to your dream beachfront retreat at The Promenade. This sunny, south-facing seventh-floor residence offers an open, spacious interior encompassing 1585 sq. ft. of living space. It’s waiting for you to make it your own and embrace the captivating views of the Gulf, Sarasota Bay, and downtown Sarasota from its wraparound terrace. With its ideal beachside location, this getaway provides an

  Judy Kepecz-Hays COLDWELL BANKER REALTY

  1211 Gulf of Mexico Dr Unit 704, Longboat Key, FL 34228
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  /38

  $5,499 per month

  • 2 Beds
  • 2 Baths
  • 1,601 Sq Ft
  • Condo for Rent

  511 Bayport Way Unit 511, Longboat Key, FL 34228

  RARELY AVAILABLE, LONGBOAT KEY 7-12 MONTH LEASE OFFERING FURNISHED RENTAL with Unparalleled Gulf of Mexico views! Marvel at the Gulf's turquoise waters and gorgeous sunsets from anywhere in this residence. This beautifully remodeled condo welcomes you with an open floor plan, featuring an expansive living/dining/kitchen combination and a main lanai to boast. The spacious master bedroom features a

  Patrick Ritchey RE/MAX ALLIANCE GROUP

  511 Bayport Way Unit 511, Longboat Key, FL 34228
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  /2

  $935,000 Sold May 07, 2025

  • 1,409 Sq Ft
  • $664/SF
  • 31 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1974

  1050 Longboat Club Rd Unit 704, Longboat Key, FL 34228

  Step into the epitome of coastal elegance in this beautifully renovated residence, perfectly situated behind the gates of the prestigious Longboat Key Club in Privateer. Offering a seamless blend of modern design and breathtaking waterfront views, this 2-bedroom, 2-bath retreat is an exceptional find on the southern end of Longboat Key. Professionally designed with both style and durability in

  Patrick Dipinto, III COLDWELL BANKER REALTY

  1050 Longboat Club Rd Unit 704, Longboat Key, FL 34228
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  /49

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 680 Sq Ft

  3710 Gulf of Mexico Dr Unit B3, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit B3, Longboat Key, FL 34228
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  /60

  $1,150,000

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

  4401 Gulf of Mexico Dr Unit 907, Longboat Key, FL 34228

  BEAUTIFUL BAY AND CITY VIEWS TO THE EAST AND SWEEPING VIEWS OF THE OCEAN TO THE WEST. This 9th floor corner unit facing north has breathtaking views. It offers full open views across the beach, including south and north areas. It feels like you're at the beach while enjoying the added comfort of the beauty from inside your home. Large lanai offers that perfect area to relax privately and enjoy

  Deborah Woods KELLER WILLIAMS ON THE WATER S

  4401 Gulf of Mexico Dr Unit 907, Longboat Key, FL 34228
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  /34

  $3,000 per month

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft
  • Condo for Rent

  3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

  2-bed, 2-bath seasonal or annual 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

  Dakota Magnus FLORIDA GALLERY REAL ESTATE

  3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
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  /2

  $460,000 Sold May 07, 2025

  • 910 Sq Ft
  • $505/SF
  • 37 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1930

  7119 Longboat Dr E, Longboat Key, FL 34228

  This fabulous little 1930's cottage has a wonderful history and is ready to be reimagined by its next visionary owner. Located in the famous "Village" of Longboat Key, it sits back on a lushly landscaped lot. It was once featured in Sarasota magazine as the "epitome of the island beach cottage". The bay is across the street and the beautiful Broadway beach is just a short walk or bike ride way.

  JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  7119 Longboat Dr E, Longboat Key, FL 34228
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  /50

  Est $1,480,134 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,839 Sq Ft

  1485 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228

  1485 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228
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  /46

  $999,995

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

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

  PRICING UPDATE! Longboat Key's best kept secret. Sands Point Condominium is everything you could ask for! Lowest priced 2 bedroom condominium in this community blending gorgeous mid-century architecture with stunning location along the Gulf of Mexico. Situated next to the Longboat Key Club complex, Sands Points offers everything you need to relax and unwind under the Florida sun and all the

  Donna Turnbaugh WAGNER REALTY

  100 Sands Point Rd Unit 225, Longboat Key, FL 34228
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  /57

  $7,500 per month

  • 3 Beds
  • 2 Baths
  • 1,962 Sq Ft
  • House for Rent

  990 Bogey Ln, Longboat Key, FL 34228

  Introducing a charming 3-bedroom, 2-bathroom single family home located in the prestigious Country Club Shores of Longboat Key, FL. This fully furnished property boasts deeded beach access, perfect for enjoying the sun and surf just steps away from your front door. The fenced backyard provides privacy and a great space for outdoor entertaining. Situated just 2.8 miles from the vibrant St. Armands

  Ray Shope ROSEBAY INTERNATIONAL REALTY, INC

  990 Bogey Ln, Longboat Key, FL 34228
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  /2

  $148,000 Sold May 07, 2025

  • 643 Sq Ft
  • $230/SF
  • 85 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1959

  3710 Gulf of Mexico Dr Unit G-6, Longboat Key, FL 34228

  WELCOME TO PARADISE: imagine a home in a beautiful beach-to-bay community. Gulfshore of Longboat Key has it all -- private, pristine sand beach on the Gulf of Mexico, a marina on Sarasota Bay, large community pool, clubhouse with a commercial kitchen, a well-maintained campus and very reasonable HOA fees. Truly, Gulfshore is a remnant of Old Florida that is just six miles from the world-famous

  Bill Shuttleworth EDGEWATER REAL ESTATE, INC

  3710 Gulf of Mexico Dr Unit G-6, Longboat Key, FL 34228
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  /33

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 880 Sq Ft

  3710 Gulf of Mexico Dr Unit G1, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit G1, Longboat Key, FL 34228
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  /29

  $290,000

  • 2 Beds
  • 2 Baths
  • 1,031 Sq Ft

  3806 Gulf of Mexico Dr Unit C205, Longboat Key, FL 34228

  Island Gulf to Bay Condo for Sale - Your Paradise Awaits! Wake up to a breathtaking walk on your own deed beach or get to the dock and take off early! This island beachfront condo is a rare opportunity to own a slice of paradise. This beautifully maintained unit offers deeded beach access, sweeping water views, heated oversize swimming pool, fitness center, private boat docking, community

  Kay Winefordner BAY VISION REALTY INC

  3806 Gulf of Mexico Dr Unit C205, Longboat Key, FL 34228
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  /32

  $5,500 per month

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

  1928 Harbourside Dr Unit 1402, Longboat Key, FL 34228

  Experience luxury and tranquility in this stunning unit at 1928 Harbourside Dr, Unit 1402, located within the Bay Isles community on Longboat Key. This residence offers a spacious layout designed for comfort and style, with access to top-tier amenities including a nearby marina, private golf course, swimming pool, and spa. Enjoy the privacy and security of this exclusive gated community, all just

  Alex Larchenko KELLER WILLIAMS ON THE WATER S

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

  $740,000 Sold May 06, 2025

  • 1,296 Sq Ft
  • $571/SF
  • 24 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  750 Russell St, Longboat Key, FL 34228

  Discover the essence of island living with this charming beach home, perfectly situated in the vibrant Village of Longboat Key. Recently renovated, this property boasts a 2-bedroom, 1-bathroom main residence Plus an above garage 1-bedroom, 1-bathroom private Suite. The main home features an open floor plan, an upgraded kitchen with brand-new appliances, upgraded bathroom and an abundance of

  Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

  750 Russell St, Longboat Key, FL 34228
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  /80

  Est $1,583,571 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,462 Sq Ft

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

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

  

  /39

  $999,000

  • 3 Beds
  • 3 Baths
  • 1,446 Sq Ft

  663 Penfield St, Longboat Key, FL 34228

  A Rare Longboat Key Value – Your Ideal Beach Retreat Awaits. Welcome to 663 Penfield Street—a hidden gem offering exceptional value on one of Longboat Key’s sought-after wide canals. This elevated three-bedroom, three-bath home boasts 1,446 sq ft of bright, open living space - emphasized by vaulted ceilings and skylights in the Kitchen/Great Room. Built in 1970 and enhanced with an elevator,

  Steve and Janet Walter MICHAEL SAUNDERS & COMPANY

  663 Penfield St, Longboat Key, FL 34228
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  /34

  $5,500 per month

  • 2 Beds
  • 2.5 Baths
  • 1,590 Sq Ft
  • Condo for Rent

  2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228

  Welcome to 2012 Harbourside Dr, a beautifully located home within the Bay Isles community on Longboat Key. This spacious residence provides access to the best of Florida’s coastal lifestyle, including a nearby marina, private golf course, pool, and spa. Enjoy the serenity of this gated community, which offers privacy and proximity to the scenic Sarasota Bay. Just a short drive from the cultural

  Alex Larchenko KELLER WILLIAMS ON THE WATER S

  2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
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  /2

  $800,000 Sold May 06, 2025

  • 1,380 Sq Ft
  • $580/SF
  • 29 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1996

  3080 Grand Bay Blvd Unit 521, Longboat Key, FL 34228

  This Aruba residence in Building 5 at Grand Bay captures the essence of coastal living with sweeping direct views of Sarasota Bay, the Harbourside golf course, and the downtown skyline. Offered furnished, this sunlit retreat features tile flooring throughout and an inviting open layout. Floor-to-ceiling glass doors frame the picturesque scenery, connecting the indoor and outdoor living spaces. A

  Roger Pettingell COLDWELL BANKER REALTY

  3080 Grand Bay Blvd Unit 521, Longboat Key, FL 34228
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  /29

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 693 Sq Ft

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

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

  

  /63

  $774,000 Open Sun 1PM - 4PM

  • 2 Beds
  • 2 Baths
  • 1,235 Sq Ft

  2295 Gulf of Mexico Dr Unit 64S, Longboat Key, FL 34228

  Sought-After Beachfront Living at The Islander Club – Resort-Style Luxury on Longboat Key. Welcome to this beautifully updated 2-bedroom, 2-bath condo in the prestigious Islander Club, one of Longboat Key’s most desirable beachfront communities. Located on the 6th floor, this spacious residence spans over 40 feet along the south/southeast side, offering breathtaking Gulf views from the primary

  Malihe Karimi MICHAEL SAUNDERS & COMPANY

  2295 Gulf of Mexico Dr Unit 64S, Longboat Key, FL 34228
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  /32

  $3,975 per month

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

  3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228

  A perfect island getaway. This well appointed and updated Longboat Key condo is available as a six or seven month rental from late June through January. Located Bay side, you'll enjoy a sparkling pool, tennis, kayak launch, fishing pier, grill area and clubhouse, plus deeded beach access is 250ft from your front door. There's plenty of room to spread out with an open, split floor plan and a huge

  Rosemarie McKee COLDWELL BANKER REALTY

  3240 Gulf of Mexico Dr Unit B404, Longboat Key, FL 34228
• 

  /2

  $625,000 Sold May 06, 2025

  • 1,440 Sq Ft
  • $434/SF
  • 3 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1991

  858 Evergreen Way, Longboat Key, FL 34228

  Welcome to this beautifully maintained, turnkey townhome located in the highly sought-after Cedars Tennis Resort and Club on Longboat Key. Surrounded by lush mature greenery, this charming home comes fully furnished offering the perfect blend of comfort and convenience. Step outside to explore scenic trails, a kayak launch, and the clubhouse just a short walk away. Enjoy an active lifestyle with

  Martin Dimovski PREMIER SOTHEBY'S INTERNATIONAL REALTY

  858 Evergreen Way, Longboat Key, FL 34228
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  /69

  Est $825,307 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,498 Sq Ft

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

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

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