Longboat Key, FL Homes

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  /67

  $2,195,000

  • 3 Beds
  • 3.5 Baths
  • 2,712 Sq Ft

  603 Weston Pointe Ct, Longboat Key, FL 34228

  Discover the epitome of luxury coastal living in this highly sought-after Weston Point patio home, ideally situated behind the exclusive gates of the Bay Isles Community and the Longboat Key Club. Enjoy the security of 24-hour guarded gate access, along with the convenience of nearby amenities including Publix, CVS, several banking institutions, and the unparalleled lifestyle offerings of

  Ryan Heers COLDWELL BANKER REALTY

  603 Weston Pointe Ct, Longboat Key, FL 34228
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  /57

  $11,500 per month

  • 3 Beds
  • 3.5 Baths
  • 3,101 Sq Ft
  • House for Rent

  2254 Harbour Court Dr, Longboat Key, FL 34228

  Nestled on the tranquil waterfront of Longboat Key, this stunning residence offers the ultimate coastal lifestyle. With direct water access and a private dock, boating and jet skiing are right at your doorstep. Two floating jet ski docks can also accommodate dinghies, making this property a boater’s dream. The home is ideally situated beside the golf course, blending serene water views with lush

  Alex Larchenko KELLER WILLIAMS ON THE WATER S

  2254 Harbour Court Dr, Longboat Key, FL 34228
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  /2

  $1,735,000 Sold Oct 01, 2025

  • 1,524 Sq Ft
  • $1,138/SF
  • 161 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  2425 Gulf of Mexico Dr Unit 3E, Longboat Key, FL 34228

  SEA GATE, a boutique 89-unit building, stands apart with its exceptional proximity to the Gulf, offering an intimate connection to the water that larger complexes simply can't match. With over 350 feet of pristine shoreline and private beach, this is the perfect setting to watch dolphins, manatees, and vibrant fish glide through the water by day, then take in mesmerizing Gulf sunsets from your

  Danelle Haag COLDWELL BANKER REALTY

  2425 Gulf of Mexico Dr Unit 3E, 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
• 

  

  

  /52

  $1,050,000

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft

  6701 Gulf of Mexico Dr Unit 330, Longboat Key, FL 34228

  Discover the charm of Whitney Beach Condominiums, a beloved Gulf-front community on beautiful Longboat Key. This delightful upper floor, end-unit, 2-bedroom, 2-bathroom condominium offers unobstructed views of the Gulf of Mexico and the perfect blend of comfort, character, and coastal charm.Lushly landscaped grounds with 600 feet of sugar-white sand beachfront, Whitney Beach invites you to

  Kamila Nowak COASTAL PROPERTIES & MGMT.

  6701 Gulf of Mexico Dr Unit 330, Longboat Key, FL 34228
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  /16

  $9,000 per month

  • 2 Beds
  • 2 Baths
  • 1,941 Sq Ft
  • Condo for Rent

  100 Sands Point Rd Unit 223, Longboat Key, FL 34228

  Location! Location! Location for Winter 2026 Rental Season!Gulf-front condominium complex “Sands Point” sits on the southernmost tip of Longboat Key. This location allows you to save time in traffic. Nestled adjacent to the iconic Longboat Key Resort, this Mid-Century modern 77-unit complex boosts impeccable views, gorgeous landscaping, a full-time maintenance crew and your own covered

  Diane Smith KELLER WILLIAMS ON THE WATER S

  100 Sands Point Rd Unit 223, Longboat Key, FL 34228
• 

  /2

  $1,020,000 Sold Sep 30, 2025

  • 1,314 Sq Ft
  • $776/SF
  • 130 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1972

  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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  /56

  Est $668,289 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
• 

  

  /40

  $1,095,000

  • 2 Beds
  • 2 Baths
  • 1,290 Sq Ft

  1000 Longboat Club Rd Unit 402, Longboat Key, FL 34228

  Coastal Elegance at Privateer South, Longboat Key!Set directly along the Gulf of Mexico, this beautifully renovated two-bedroom residence at Privateer South offers effortless beachfront living within the gates of the prestigious Longboat Key Club. Move-in ready, every detail of this turnkey fourth-floor getaway speaks to comfort, style, and sophistication, framed by sweeping Gulf views and

  Roger Pettingell COLDWELL BANKER REALTY

  1000 Longboat Club Rd Unit 402, Longboat Key, FL 34228
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  /71

  $9,000 per month

  • 2 Beds
  • 2 Baths
  • 1,561 Sq Ft
  • Condo for Rent

  5757 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

  Beautiful completely remodeled 2-bedroom, 2-bathroom Tropical Oasis on Longboat Key. Relax and enjoy the Florida lifestyle at its best with stunning gulf views from this gorgeous second floor retreat. Just steps to the beautiful white sand and warm gulf waters. Upgrades include new open floor plan with spacious rooms decorated in a soothing coastal color palette. Heightened ceilings, hardwood

  Roxanne Klopp JENNETTE PROPERTIES, INC.

  5757 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
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  /2

  $1,150,000 Sold Sep 26, 2025

  • 4,997 Sq Ft
  • $230/SF
  • 74 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2025

  2944 Gulf of Mexico Dr, Longboat Key, FL 34228

  Under Construction. Exceptional Custom Home Opportunity with Unobstructed Gulf Views!2944 Gulf of Mexico Dr offers a rare and exciting opportunity to own and complete a luxury coastal estate on Longboat Key. From the third floor and rooftop deck, enjoy beautiful, unobstructed views of the Gulf of Mexico and breathtaking sunset vistas.The property boasts a prime location with two

  Francis Perdisatt PREFERRED SHORE LLC

  2944 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /51

  Est $324,077 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
• 

  

  /54

  $975,000

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

  2295 Gulf of Mexico Dr Unit 115, Longboat Key, FL 34228

  Wonderful "Manhattan Style" beachfront Condo with sweeping views of Sarasota Bay and views of the Gulf now available at the popular Islander Club on LBK. This gorgeous beachfront renovation was completed 4 years ago and truly shows all the craftmanship that went into the process under the owner's direction. Open kitchen beings the morning light into the room for enjoying your coffee or tea as you

  Michael Nink, PA MICHAEL SAUNDERS & COMPANY

  2295 Gulf of Mexico Dr Unit 115, Longboat Key, FL 34228
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  /40

  $12,500 per month

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

  1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228

  Available for 2026 and 2027 Season!! Welcome to The Privateer, one of Longboat Key’s most coveted beachfront communities. This 10th-floor residence offers a rare opportunity to experience refined coastal living with panoramic, unobstructed views of the Gulf of Mexico. From the moment you step inside, you are greeted by a light-filled interior that opens seamlessly to two private balconies, each

  Jenna Genovese KELLER WILLIAMS ON THE WATER S

  1000 Longboat Club Rd Unit 1001, Longboat Key, FL 34228
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  /2

  $490,000 Sold Sep 25, 2025

  • 1,332 Sq Ft
  • $368/SF
  • 91 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1988

  603 Cedars Ct, Longboat Key, FL 34228

  Wonderful opportunity is now yours! Welcome to 603 Cedars Ct, a lovely and very well kept townhome in the vibrant fitness and tennis community of Cedars East, ideally located between Sarasota Bay and the Gulf of Mexico on picturesque Longboat Key - just a short stroll to the island's sugary white sand beaches, and tranquil turquoise waters.This turnkey furnished, three-level townhouse offers

  Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

  603 Cedars Ct, Longboat Key, FL 34228
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  /42

  Est $350,377 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
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  /76

  $2,790,000 Open Sun 1PM - 4PM

  • 5 Beds
  • 5 Baths
  • 4,510 Sq Ft

  3408 Fair Oaks Ln, Longboat Key, FL 34228

  Elegant 5BR/5BA home in the gated community of Corey’s Landing within Bay Isles on Longboat Key. With over 4,500 sq ft, this spacious two-story residence offers open living areas, soaring ceilings, and refined design for both comfort and style. The light-filled great room with 22-ft ceilings opens to a gourmet kitchen with stone countertops, breakfast bar, and stainless-steel appliances. The

  Bruce Myer COLDWELL BANKER REALTY

  3408 Fair Oaks Ln, Longboat Key, FL 34228
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  /13

  $3,000 per month

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

  3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228

  LONGBOAT KEY...Lovely 2 bedroom 2 bath condo directly across from the private beach. Updated kitchen with stainless steel appliances and master and guest bathrooms with ceramic tile. Split floor plan, master suite with a king size bed and the guest room has bunk beds with one single bed and one full size bed. Spacious, open, light and bright. Very well maintained GULF TO BAY complex with lush

  Teresa Ribaudo JENNETTE PROPERTIES INC

  3806 Gulf of Mexico Dr Unit C212, Longboat Key, FL 34228
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  /2

  $2,150,000 Sold Sep 24, 2025

  • 3,252 Sq Ft
  • $661/SF
  • 125 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1988

  2282 Harbour Court Dr, Longboat Key, FL 34228

  Stunning sunrises greet you each morning at this bayfront home with expansive water and city skyline views. Harbour Court in Bay Isle is a secluded haven of just 18 bayfront residences set amidst lush tropical gardens. Entertain on your bayfront terrace as the moon rises over the water. Enjoy boating, kayaking and fishing from your dock, or just watching the dolphins and manatees from your

  Ann Martin MICHAEL SAUNDERS & COMPANY

  2282 Harbour Court Dr, Longboat Key, FL 34228
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  /60

  Est $760,975 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
• 

  

  /73

  $2,215,000

  • 4 Beds
  • 3 Baths
  • 1,840 Sq Ft

  510 Wedge Ln, Longboat Key, FL 34228

  Welcome to your own piece of paradise in the prestigious Country Club Shores neighborhood on Longboat Key. This stunning 4-bedroom, 3-bath home has been thoughtfully renovated with a perfect blend of coastal elegance and modern sophistication, offering ideal indoor-outdoor living along one of the island’s serene canals. Inside, you’ll be welcomed by a bright, open-concept design featuring

  Courtney Tarantino COLDWELL BANKER REALTY

  510 Wedge Ln, Longboat Key, FL 34228
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  /59

  $11,000 per month

  • 3 Beds
  • 3 Baths
  • 2,772 Sq Ft
  • House for Rent

  3390 Bayou Sound, Longboat Key, FL 34228

  **This is a 2 month minimum vacation rental**Welcome to 3390 Bayou Sound, located within the exclusive, gated community of Bay Isles on picturesque Longboat Key. This prime location offers access to world-renowned beaches, a marina, golf courses, biking trails, and tennis facilities. Nestled on an oversized, beautifully landscaped corner lot in the Bayou section of Bay Isles, this

  Jennifer LeBlanc PRECISE REALTY CORP

  3390 Bayou Sound, Longboat Key, FL 34228
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  /2

  $430,000 Sold Sep 22, 2025

  • 666 Sq Ft
  • $646/SF
  • 156 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1973

  4235 Gulf of Mexico Dr Unit G203, Longboat Key, FL 34228

  REDUCED PRICE!!! SELLER will pay up to $20,000 of Buyers closing cost. Great investor or seasonal rental property - This charming turnkey short-term vacation rental one bedroom with two queen size beds, one bath and a queen size sofa sleeper, living-dining combo is a beach side end unit. It comfortably accommodates six individuals for an enjoyable stay. Including a screened in porch, plantation

  George Sanchez EZ CHOICE REALTY

  4235 Gulf of Mexico Dr Unit G203, Longboat Key, FL 34228
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  /53

  Est $650,246 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 896 Sq Ft

  4401 Gulf of Mexico Dr Unit 503, Longboat Key, FL 34228

  4401 Gulf of Mexico Dr Unit 503, Longboat Key, FL 34228
• 

  

  /32

  $1,000,000 Open Wed 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft

  4325 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228

  Experience the relaxed Gulf Coast lifestyle at Tiffany Plaza - direct Gulf-front, accessible community on Longboat Key where every day feels like a beach vacation. Go from your patio onto the sand and enjoy spectacular sunsets. This inviting two-bedroom, two-bath residence offers a spacious open living and dining area ideal for hosting 8-12 guests. Updated with stone countertops, fresh paint, new

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4325 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
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  /67

  $4,000 per month

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Condo for Rent

  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
• 

  /2

  $935,000 Sold Sep 19, 2025

  • 1,509 Sq Ft
  • $620/SF
  • 39 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1985

  615 Dream Island Place Unit 304, Longboat Key, FL 34228

  This beautifully renovated 2-bedroom condo is back on the market with even more special updates. Just completed: new lighting and ceiling fan fixtures throughout; primary bath renovation; guest bath renovation; freshly painted interior. The primary bath features a dual-sink vanity with quartz counters, lighted and mirrored cabinets, a large walk-in shower with dual shower heads, a linen closet

  Andree Huffine COLDWELL BANKER REALTY

  615 Dream Island Place Unit 304, Longboat Key, FL 34228
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  /80

  Est $2,831,604 Not Listed For Sale

  • 2 Beds
  • 4.5 Baths
  • 2,965 Sq Ft

  1241 Gulf of Mexico Dr Unit 707, Longboat Key, FL 34228

  1241 Gulf of Mexico Dr Unit 707, Longboat Key, FL 34228
• 

  

  /38

  $1,150,000

  • 1 Bed
  • 1 Bath
  • 634 Sq Ft

  230 Sands Point Rd Unit 3205, Longboat Key, FL 34228

  Spectacular Gulf and Sunset views are enjoyed from this west facing Junior Suite in Building 3. The direct beach view through the swaying palms perfectly encompasses the resort lifestyle and the vision guests have of tropical landscapes when making reservations. This completely renovated residence is currently in the hotel program and reported healthy income in 2023 and 2024. As an owner, you are

  Ian Addy, PA MICHAEL SAUNDERS & COMPANY

  230 Sands Point Rd Unit 3205, Longboat Key, FL 34228
• 

  

  /28

  $4,500 per month

  • 2 Beds
  • 2 Baths
  • 1,168 Sq Ft
  • Condo for Rent

  4420 Exeter Dr Unit 208, Longboat Key, FL 34228

  2025 WINTER RENTAL- Available Oct 1, 2025- May 24, 2026. Talk about the perfect beach place. Intercoastal view and private easy access to the beach with a private beach house! Longboat Harbour Condominium Association has tennis courts, a fitness center, Kayak launching pads, docks, fishing areas, many pools, private access to the beach on the Gulf of Mexico. Marina slips MAY be available so you

  Armando Gonzalez AG REALTY SERVICES LLC

  4420 Exeter Dr Unit 208, Longboat Key, FL 34228
• 

  /2

  $445,000 Sold Sep 18, 2025

  • 1,284 Sq Ft
  • $347/SF
  • 78 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  3630 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

  DEEDED BOAT SLIP. Experience the ultimate in Gulf Coast living at Buttonwood Cove. Welcome to island life at its finest! This highly sought-after 2 bedroom, 2 bathroom waterfront condominium offers the perfect blend of comfort, captivating views, and resort-style amenities, nestled in one of Longboat Key’s most desirable communities. As you arrive, you’ll be greeted by lush, impeccably maintained

  Joey Lamielle RE/MAX ALLIANCE GROUP

  3630 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
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  /75

  Est $3,916,284 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,122 Sq Ft

  4975 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  4975 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
• 

  

  /56

  $999,000

  • 2 Beds
  • 2 Baths
  • 1,668 Sq Ft

  1465 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. This 2 Bedroom, 2 Bath condo overlooking the Gulf has an open kitchen with breakfast bar. It also has a computer nook with a window overlooking the East terrace. The coveted great room design adds to the casual beachfront living experience. The split plan allows for great personal space. Each bedroom has access to its own bath and each bedroom also

  Tammy Garner COLDWELL BANKER REALTY

  1465 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
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  /68

  $29,000 per month

  • 5 Beds
  • 5.5 Baths
  • 4,858 Sq Ft
  • House for Rent

  591 Putting Green Ln, Longboat Key, FL 34228

  LONGBOAT KEY...If you're looking for a Luxury winter vacation home, stop searching. You have just found the perfect house located on a private & peaceful cul-de-sac. This beautiful 5 bedroom, 5.1 bathrooms has everything you would want and more with all the comforts of home. All new furniture throughout in every room. Primary, 1st & 2nd bedrooms all have king size beds. Bedrooms 3 & 4 have twin

  Teresa Ribaudo JENNETTE PROPERTIES INC

  591 Putting Green Ln, Longboat Key, FL 34228
• 

  /2

  $3,900,000 Sold Sep 18, 2025

  • 3,564 Sq Ft
  • $1,094/SF
  • 201 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1995

  655 Longboat Club Rd Unit 14A, Longboat Key, FL 34228

  ** The Seller requests NO SOLICITATION COMMUNICATIONS of any kind. LISTING WITHDRAWN, WILL BE RE-ACTIVATED.**Furnished and move-in ready, this direct Gulf-front residence at Regent Place is a rare opportunity to own an exquisite beachfront retreat. Offering breathtaking views of the Gulf of Mexico to the west and the rolling greens of the Links on Longboat Golf Course to the east, this

  Roger Pettingell COLDWELL BANKER REALTY

  655 Longboat Club Rd Unit 14A, Longboat Key, FL 34228
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  /63

  Est $848,232 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
• 

  

  /37

  $1,250,000

  • 3 Beds
  • 2 Baths
  • 1,323 Sq Ft

  5320 Gulf of Mexico Dr Unit 101, Longboat Key, FL 34228

  Rarely Available at Longboat Landing! This 3-bedroom, 2-bath second-floor condo offers the ultimate in coastal living with only 9 total units/owners in the entire community—providing privacy, exclusivity, and a boutique feel. Enjoy full Sarasota Bay views from your living room, with the added peace of mind of being on the second floor (no flood concerns). Inside, you’ll find engineered hardwood

  Schuyler Burke KELLER WILLIAMS ON THE WATER S

  5320 Gulf of Mexico Dr Unit 101, Longboat Key, FL 34228
• 

  

  /58

  $4,000 per month

  • 2 Beds
  • 2 Baths
  • 931 Sq Ft
  • House for Rent

  4760 Gulf of Mexico Dr, Longboat Key, FL 34228

  BRAND NEW BEACH & BAY VILLA! Renovated with precision, the final finishing touches were completed March 26, 2025 for this quality engineered, down to the studs, two-bedroom and two-bath beach getaway villa. Available immediately. September & October $4,000 a month. November & December $5,000 a month. From the moment you step inside, you'll be greeted by a thoughtfully designed sunny open floor

  Debby McCaig COLDWELL BANKER REALTY

  4760 Gulf of Mexico Dr, Longboat Key, FL 34228
• 

  /2

  $3,050,000 Sold Sep 16, 2025

  • 4,200 Sq Ft
  • $726/SF
  • 5 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1991

  3531 Bayou Pointe, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. Spectacular Waterfront Estate in Bay Isles | Longboat KeyRarely does a property of this caliber come to market. Located behind the exclusive, 24-hour guarded gates of the Longboat Key Club in the prestigious Bay Isles community, this estate spans 4,200 square feet of elegant one level living space. With 5 spacious bedrooms, 4.5 baths, plus a

  Ryan Heers COLDWELL BANKER REALTY

  3531 Bayou Pointe, Longboat Key, FL 34228
• 

  

  /48

  Est $1,155,577 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

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