Longboat Key, FL Homes

• 

  

  

  /54

  $1,050,000

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

  1065 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228

  Welcome to your slice of Paradise with Southern exposure and peek-a-boo Gulf views in award-winning Beachplace! This beautifully situated 1st floor unit is overlooking Longboat Key Club Golf Course and just steps to 1,450 feet of private beach. Enjoy all-day sun, sunsets, and direct access via private stairs to the grilling area and beach walkover with chaise lounges and umbrellas. Open floor

  Bonita Schiavone PREFERRED SHORE LLC

  1065 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228
• 

  

  

  /23

  $5,000 per month

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

  1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228

  Turnkey Townhouse on Longboat Key – Resort-Style Living!Live the island dream in this beautifully furnished 2-bedroom, 2.5-bathroom townhouse in the exclusive gated community of Fairway Bay. Located on picturesque Longboat Key, this bright and spacious home offers two ensuite bedrooms for ultimate comfort and privacy.Enjoy private beach access to the stunning Gulf of Mexico, take

  Victoria Campbell LPT REALTY LLC

  1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228
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  /2

  $1,050,000 Sold Jul 21, 2025

  • 1,579 Sq Ft
  • $665/SF
  • 127 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1978

  650 Penfield St, Longboat Key, FL 34228

  An ELEVATED waterfront home uniquely positioned in an exceptional location on the fabulous north end of Longboat Key. This laid back, friendly, single-family neighborhood adds to the charm. With no high rises here, your morning strolls on the beach are only crowded by the shore birds. Surrounded by trees on all sides and sitting on a 10,230sf lot, when you enter into this home, you truly have a

  JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  650 Penfield St, Longboat Key, FL 34228
• 

  

  

  /63

  Est $826,804 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,224 Sq Ft

  2213 Harbourside Dr Unit 303, Longboat Key, FL 34228

  2213 Harbourside Dr Unit 303, 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.

  Deborah Marcum EQUITY CONSULTANTS INC

  588 Bayview Dr, Longboat Key, FL 34228
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  /44

  $15,000 per month

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

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

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

  Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

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

  $130,000 Sold Jul 18, 2025

  • 902 Sq Ft
  • $144/SF
  • 208 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1965

  88 Twin Shores Blvd, Longboat Key, FL 34228

  Welcome to this 2-bedroom, 2-bath mobile home, a perfect blank canvas awaiting your creative touch. Situated in the sought-after Twin Shores community, this property is being offered at land value due to the effects of Hurricane Helene. The opportunities for crafting your dream retreat in this picturesque area are limitless. The Twin Shores Mobile Home Park boasts a welcoming atmosphere and a

  Darren Dowling BEYOND REALTY LLC

  88 Twin Shores Blvd, Longboat Key, FL 34228
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  /48

  Est $1,173,321 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,678 Sq Ft

  3437 Winding Oaks Dr Unit 19, Longboat Key, FL 34228

  3437 Winding Oaks Dr Unit 19, Longboat Key, FL 34228
• 

  

  /38

  $639,000

  • 2 Beds
  • 2.5 Baths
  • 1,440 Sq Ft

  847 Evergreen Way, Longboat Key, FL 34228

  Income-Producing Coastal Gem – This TURNKEY FURNISHED 2BR/2.5BA townhome in the exclusive Cedars East Tennis Resort isn’t just a slice of paradise—it’s a proven performer. With $80,000 in past annual rental income and future bookings already secured, this property offers immediate cash flow and long-term upside. Inside, enjoy 1,440 sq ft of updated living space featuring a gourmet kitchen with

  Kiki Bowers COLDWELL BANKER REALTY

  847 Evergreen Way, Longboat Key, FL 34228
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  /48

  $2,495 per month

  • 2 Beds
  • 2 Baths
  • 1,007 Sq Ft
  • Condo for Rent

  3810 Gulf of Mexico Dr Unit 206, Longboat Key, FL 34228

  GULF to BAY ACCESS! Beach Harbour Club Welcomes you home to Island living. New to the rental market is this second floor condo featuring 2 bedrooms, 2 bathrooms, dining room / family room combination and a full size washer / dryer located in the utility room. Beach Harbour Club is centrally located in the middle of Long Boat Key and this condo is a turn key fully furnished ANNUAL rental. There is

  Edward Whitaker PERLA'S PROPERTIES, LLC

  3810 Gulf of Mexico Dr Unit 206, Longboat Key, FL 34228
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  /2

  $500,000 Sold Jul 16, 2025

  • 1,416 Sq Ft
  • $353/SF
  • 110 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1954

  651 Fox St, Longboat Key, FL 34228

  Opportunity is knocking! Currently one of the lowest priced homes on Longboat Key!! Bring your vision and reimagine this wonderful spot for your own island paradise! This home and the separate 2 story apartment were both completely renovated before the storm. A newer metal roof and storm rated windows and doors kept the home and apartment safe from the wind, but were damaged by water intrusion

  JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  651 Fox St, Longboat Key, FL 34228
• 

  /2

  Est $604,856 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,601 Sq Ft

  829 Bayport Way Unit 829 B, Longboat Key, FL 34228

  829 Bayport Way Unit 829 B, Longboat Key, FL 34228
• 

  

  /8

  $5,000,000

  • 5 Beds
  • 3 Baths
  • 3,492 Sq Ft

  6601 Gulfside Rd, Longboat Key, FL 34228

  Discover a truly rare opportunity to own two parcels in a new, beachfront enclave being developed with private entry gates directly on the pristine sugar sand and turquoise waters of the Gulf of Mexico. The offering includes: Parcel One - Property ID: 7847710154 - 72,000 sq. ft. homesite with 100 ft. of direct Gulf frontage. Parcel Two - Property ID: 7847700007 - A 9,757 sq. ft. privately owned,

  Debra Lichter SARASOTA BEACH TO BAY INC

  6601 Gulfside Rd, Longboat Key, FL 34228
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  /47

  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft
  • Condo for Rent

  4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  Furnished beachfront vacation rental! This spacious (1336 sq ft + balcony) condo is a luxurious living space that offers breathtaking panoramic views of the beach, sunset, and Gulf of Mexico. It is located in a smaller building, on an uncrowded segment of beach that can often be enjoyed in complete solitude. The unit was recently upgraded with a new washer/dryer, luxury vinyl flooring in the

  Daniel Goldman COMPASS FLORIDA LLC

  4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
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  /2

  $950,000 Sold Jul 15, 2025

  • 1,235 Sq Ft
  • $769/SF
  • 60 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  2301 Gulf of Mexico Dr Unit 26, Longboat Key, FL 34228

  This tranquil second floor residence at Islander Club of Longboat Key boasts direct full views of the Gulf of Mexico, complete with spellbinding sunsets, sandy shores, and soothing sounds of the surf. An enchanting beachfront getaway, this furnished condo offers two bedrooms and two full bathrooms, with a spacious open living & dining space, and a private terrace that spans almost the entire

  Doug Parks MICHAEL SAUNDERS & COMPANY

  2301 Gulf of Mexico Dr Unit 26, Longboat Key, FL 34228
• 

  

  /25

  Est $1,360,445 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,180 Sq Ft

  1902 Harbour Links Cir Unit 16, Longboat Key, FL 34228

  1902 Harbour Links Cir Unit 16, Longboat Key, FL 34228
• 

  

  /56

  $745,000

  • 3 Beds
  • 3 Baths
  • 1,824 Sq Ft

  560 Cedar St, Longboat Key, FL 34228

  Island Living in Longbeach Village – 3 Bed, 3 Bath Coastal RetreatDiscover the perfect blend of island charm and modern comfort in this beautifully updated 3-bedroom, 3-bathroom home nestled in the sought-after Longbeach Village of Longboat Key. Situated on a desirable corner lot, this residence offers the ultimate coastal lifestyle in one of the area’s most historic and beloved

  Lauren Hofing THE KEYES COMPANY - SARASOTA

  560 Cedar St, Longboat Key, FL 34228
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  /60

  $6,900 per month

  • 2 Beds
  • 2.5 Baths
  • 1,440 Sq Ft
  • House for Rent

  535 Forest Way, Longboat Key, FL 34228

  Welcome to your perfect coastal escape in the heart of Cedars East on Longboat Key, Florida! Professionally managed by Gulf Coast Vacation Rentals, this chic, playful, and stylish 3-story, 2-bedroom, 2-bathroom townhome is nestled in one of the island’s most sought-after communities—offering a unique blend of tropical charm, resort-style amenities, and a peaceful coastal atmosphere.Step into

  Andy Moore GULF COAST REALTY & MANAGEMENT

  535 Forest Way, Longboat Key, FL 34228
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  /2

  $650,000 Sold Jul 15, 2025

  • 1,540 Sq Ft
  • $422/SF
  • 288 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1975

  780 Tarawitt Dr, Longboat Key, FL 34228

  Home available to show and was unaffected by the recent Hurricane Milton. Majestic Waterfront Living in Longboat Key boasts DEEDED BEACH ACCESS to a private Gulf of Mexico beach and is walking distance to renowned Harry’s Kitchen and Delicatessen. Nestled in the serene beauty of Longboat Key, this waterfront 3-bedroom, 2-bathroom ranch home spans over 1,500 Sq Ft of an unparalleled blend of

  Sophia Kramedas-Ghanayem KW SUNCOAST

  780 Tarawitt Dr, Longboat Key, FL 34228
• 

  

  /66

  Est $511,669 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,399 Sq Ft

  583 Spanish Dr S Unit 129, Longboat Key, FL 34228

  583 Spanish Dr S Unit 129, 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
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  /33

  $7,850 per month

  • 2 Beds
  • 2 Baths
  • 2,331 Sq Ft
  • House for Rent

  701 Broadway St, Longboat Key, FL 34228

  Newly remodeled bungalow blocks from Whitney Beach & a block from bay. Historic home was once a post office in the 1920's. Open layout w/high ceilings, stainless appliances w/ gas stove. Heated swimming pool & hot tub. Relax & listen to breezy palms smack up against each other in this gorgeous landscaping! Sleep tight in a quiet neighborhood that allows zero public parking. Very serene, private

  Keith Gordon GETMOREOFFERS

  701 Broadway St, Longboat Key, FL 34228
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  /2

  $250,000 Sold Jul 14, 2025

  • 1,361 Sq Ft
  • $184/SF
  • 20 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  683 Spanish Dr S Unit 214, Longboat Key, FL 34228

  Coastal Living at Its Finest! Located in the highly sought-after Spanish Main Yacht Club, this 2-bedroom, 2-bath villa offers 1,361 sq ft under air (1,677 total sq ft) and is ready for rebuild after the storm—a perfect opportunity to customize your dream home in one of Longboat Key’s premier 55+ waterfront communities.Enjoy a spacious, light-filled open floor plan with a generous primary

  Geoff Scalera AUM FLORIDA REAL ESTATE LLC

  683 Spanish Dr S Unit 214, Longboat Key, FL 34228
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  /2

  Est $1,540,995 Not Listed For Sale

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

  1055 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228

  1055 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228
• 

  

  /14

  $395,000

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

  509 Spanish Dr N, Longboat Key, FL 34228

  Offers 1% lender credit at closing. Welcome to your slice of paradise on Longboat Key! Just steps from the white sandy beaches and turquoise Gulf waters, this beautifully updated villa combines peace of mind with effortless coastal living. Completely mitigated per FEMA guidelines, the home offers confidence and comfort with thoughtful upgrades throughout. Inside, you’ll find brand new doors,

  Jennifer Kenna EXP REALTY LLC

  509 Spanish Dr N, Longboat Key, FL 34228
• 

  

  /57

  $7,500 per month

  • 3 Beds
  • 2.5 Baths
  • 2,490 Sq Ft
  • Condo for Rent

  380 Gulf of Mexico Dr Unit 513, Longboat Key, FL 34228

  Available now through the end of the year, off season only. Welcome to coastal elegance at Tangerine Bay Club, where sweeping bay views set the stage for an exceptional lifestyle. This furnished residence captures the charm of a single-family home with its private courtyard entrance while offering all the benefits of resort-style community living. This comfortable three-bedroom retreat features a

  Maureen Plichta STRINGER MANAGEMENT INC

  380 Gulf of Mexico Dr Unit 513, Longboat Key, FL 34228
• 

  /2

  $1,700,000 Sold Jul 14, 2025

  • 1,842 Sq Ft
  • $923/SF
  • 132 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1984

  775 Longboat Club Rd Unit 902, Longboat Key, FL 34228

  Nestled within the gates of the exclusive Longboat Key Club, this fully furnished move in tomorrow 9th-floor corner condo offers sweeping panoramic views from the Gulf of Mexico to Sarasota Bay, making it an unparalleled beachfront retreat. With three generously sized bedroom suites and three beautifully appointed bathrooms, this luxury residence offers the perfect blend of comfort and

  Courtney Tarantino COLDWELL BANKER REALTY

  775 Longboat Club Rd Unit 902, Longboat Key, FL 34228
• 

  

  /64

  Not Listed For Sale

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

  2295 Gulf of Mexico Dr Unit 112, Longboat Key, FL 34228

  2295 Gulf of Mexico Dr Unit 112, Longboat Key, FL 34228
• 

  

  /17

  $300,000

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

  A fantastic view of the city skyline from the 48 x 21 foot slip at Longboat Key Club Moorings! 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 restaurants, shopping (close to Publix, CVS, and

  Jennifer Wilson LBRE LLC

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

  

  /100

  $25,000 per month

  • 1 Bed
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228

  Welcome Serenity Oasis, your paradise at The Residences at the St.?Regis on Longboat Key—where luxury, elegance, and coastal charm converge in this stunning 1-bedroom, 2-bathroom condo. From the moment the elevator opens directly into your private entryway, you’ll be captivated by the exquisite design and attention to detail throughout this sophisticated retreat.The expansive living room is

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228
• 

  /2

  $2,700,000 Sold Jul 14, 2025

  • 4,127 Sq Ft
  • $654/SF
  • 255 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2000

  549 Sloop Ln, Longboat Key, FL 34228

  Experience unparalleled luxury and elegance at this prestigious Country Club Shores residence, nestled on the sought-after south end of Longboat Key. Designed by renowned architect and interior designer George Merlin.

  Tracey Stetler COLDWELL BANKER REALTY

  549 Sloop Ln, Longboat Key, FL 34228
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  /31

  Est $895,563 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 657 Sq Ft

  210 Sands Point Rd Unit 2302, Longboat Key, FL 34228

  210 Sands Point Rd Unit 2302, Longboat Key, FL 34228
• 

  

  /53

  $825,000 Open Fri 1PM - 4PM

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

  4500 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

  Spectacular, unobstructed Bay views over the marina and mangrove islands and the rare opportunity for two pets, a feature seldom available among condominiums on Longboat Key! This light and bright, two-bedroom, two-bath condominium spans 1,312 square feet and is ideally located across from the Zota Beach Resort, with three convenient beach access points, including one deeded beach access. The

  Sharon Austin PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4500 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
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  /42

  $7,800 per month

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • Condo for Rent

  4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  SEASONAL: Stunning Gulf views and beautiful sunsets from this spacious, immaculate turnkey furnished 2-bedroom, 2 bath split plan corner unit. Featuring 2 tiled screen enclosed lanais that overlooking lush garden, pools and, of course, serene beach views. This turnkey residence comes complete with cable & wifi, in unit washer/dryer, large walk-in closets and covered parking. The Master suite

  Diann Thelen GULF COAST RENTAL HOMES&CONDOS

  4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
• 

  /2

  $3,300,000 Sold Jul 11, 2025

  • 3,710 Sq Ft
  • $889/SF
  • 335 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1977

  750 Penfield St, Longboat Key, FL 34228

  Nestled in the North Longboat Key area, this stunning five-bedroom home rebuilt in 2014 with new pool and many other features offers unparalleled luxury and breathtaking views. As you step through the sliding glass doors from the main living area to the terrace, you are greeted by the expansive vistas of Sarasota Bay and the Intercoastal Waterway. This property is an epitome of modern elegance,

  Reid Murphy DEVELOPERS REALTY LBK, INC

  750 Penfield St, Longboat Key, FL 34228
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  /53

  Est $765,253 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
• 

  

  /41

  $380,000

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

  667 El Centro, Longboat Key, FL 34228

  Spanish Main Yacht Club on Longboat Key is a warm and vital boating community with its private beach access to Gulf beaches, 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 has contracted with the community contractor. has paid related assessment and work is

  Holly Switow PREMIER SOTHEBY'S INTERNATIONAL REALTY

  667 El Centro, Longboat Key, FL 34228
• 

  

  /21

  $45,000 per month

  • 4 Beds
  • 4.5 Baths
  • 3,961 Sq Ft
  • Condo for Rent

  2251 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

  Step into unparalleled elegance with this stunning 4-bedroom, 4.5-bathroom beachfront condo, where modern sophistication meets coastal serenity. This exclusive residence boasts floor-to-ceiling windows that fill the space with natural light and showcase breathtaking panoramic Gulf views from every angle. Designed for ultimate privacy and comfort, the unit features direct elevator access, a

  Larry Starr SVN COMMERCIAL ADVISORY GROUP

  2251 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
• 

  /2

  $925,000 Sold Jul 10, 2025

  • 1,624 Sq Ft
  • $570/SF
  • 25 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  5055 Gulf of Mexico Dr Unit 232, Longboat Key, FL 34228

  Discover the epitome of coastal beachfront living with unparalleled gulf views in this beautifully renovated turnkey top-floor, corner-unit condominium with two bedrooms, two baths plus office/den that could become a third bedroom, in the sought-after Club Longboat Beach and Tennis Condos. Offered fully furnished, this exquisite residence boasts floor-to-ceiling sliding glass doors in the living

  Nathan Mathers PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5055 Gulf of Mexico Dr Unit 232, Longboat Key, FL 34228
• 

  

  /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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