Longboat Key, FL Homes

• 

  

  

  /99

  $1,595,000

  • 2 Beds
  • 2 Baths
  • 1,513 Sq Ft

  2425 Gulf of Mexico Dr Unit 10F, Longboat Key, FL 34228

  Gulf-Front Elegance | Sea Gate Club #10F | Longboat Key —Welcome to Sea Gate Club #10F, a rarely available 10th-floor end unit offering spectacular, front-row Gulf views in one of Longboat Key’s most intimate beachfront communities. Perfectly positioned mid-island along the sandy shores of the Gulf of Mexico, this elegant 2-bedroom, 2-bath residence captures direct, unobstructed views of the

  Erica Thomas MICHAEL SAUNDERS & COMPANY

  2425 Gulf of Mexico Dr Unit 10F, Longboat Key, FL 34228
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  /31

  $10,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,957 Sq Ft
  • Condo for Rent

  1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

  Luxury Living meets Modern Coastal at Gulf Front Haven, a beautifully updated, modern, ocean view floorplan that sits right on the beach at Longboat Key, one of the Gulf Coasts Premier Living Areas! This home is located right in the heart of the Players Club, one of Longboat Keys most luxurious communities with all the amenities to make your stay great!! The condo is located on the 3rd Floor with

  Brad Wilson M&M PROPERTY MANAGEMENT GROUP

  1445 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
• 

  

  /2

  $1,450,000 Sold Oct 10, 2025

  • 2,480 Sq Ft
  • $585/SF
  • 239 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1990

  3491 Byron Ln, Longboat Key, FL 34228

  Luxurious Villa with Stunning Lake & Fairway ViewsNestled behind the exclusive gates of the Longboat Key Club, this exquisite three-bedroom, three-bathroom villa in Coreys Landing offers the perfect blend of privacy, elegance, and resort-style living. Positioned on the signature fifth fairway with southern exposure, enjoy breathtaking lake views and an abundance of natural light

  Gigi Silverberg DOUGLAS ELLIMAN

  3491 Byron Ln, Longboat Key, FL 34228
• 

  

  

  /79

  Est $5,105,280 Not Listed For Sale

  • 5 Beds
  • 6.5 Baths
  • 5,225 Sq Ft

  1241 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  1241 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
• 

  

  

  /40

  $989,000

  • 4 Beds
  • 3 Baths
  • 2,106 Sq Ft

  608 Saint Judes Dr, Longboat Key, FL 34228

  A TRUE FLORIDA DREAM HOME! WALKING DISTANCE TO ONE OF FLORIDA'S MOST BEAUTIFUL BEACH! This 4 bedroom, 3 bath and 2 car garage home is newly renovated thoughout. Step through the door into the spacious open kitchen and living area that expands into a back additional living area large enough for lounging and a pool table. 4 bedrooms and 3 bathrooms offers ample space for family and friends. The

  Cassandra MacDonald TALL PINES REALTY

  608 Saint Judes Dr, Longboat Key, FL 34228
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  /42

  $3,000 per month

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Condo for Rent

  4340 Falmouth Dr Unit 201, Longboat Key, FL 34228

  2 Bd/2 Bath on Sarasota Bay Across from Gulf of Mexico - Unit available November 3, 2025 - December 13, 2025 and May 1, 2026 - December 12, 2026.Beautiful corner unit condo with an abundance of windows located between Sarasota Bay and across the street from the deeded Gulf of Mexico beach. The gated community complex has every amenity imaginable - four pools, tennis court, shuffleboard,

  4340 Falmouth Dr Unit 201, Longboat Key, FL 34228
• 

  /2

  $1,538,000 Sold Oct 08, 2025

  • 2,180 Sq Ft
  • $706/SF
  • 46 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1979

  2675 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228

  What a wonderful opportunity to own in a very private building with only twenty residents. This large 3bed/3bath corner condominium located on the 4th floor facing the azure waters of the Gulf of Mexico with full gulf views. The views are breathtaking to wakeup to every morning and watch the magnificent sunsets in the evening. Coming totally unfurnished to decorate and choose the furnishings and

  Sandra Endres COLDWELL BANKER REALTY

  2675 Gulf of Mexico Dr Unit 404, Longboat Key, FL 34228
• 

  

  /59

  Est $2,386,933 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,603 Sq Ft

  240 Sands Point Rd Unit 4407, Longboat Key, FL 34228

  240 Sands Point Rd Unit 4407, Longboat Key, FL 34228
• 

  

  /33

  $495,000

  • 2 Beds
  • 1 Bath
  • 933 Sq Ft

  1935 Gulf of Mexico Dr Unit G7304, Longboat Key, FL 34228

  Experience the best of coastal living in this beautifully maintained 2-bedroom, 1-bathroom condominium, perfectly situated on the third floor of the desirable Seaside community on Longboat Key. Set within a secure, 24-hour guard-gated enclave, this charming residence offers both privacy and peace of mind. Step inside to discover a light and airy interior that was tastefully repainted in April

  Alie Espinoza EATON REALTY

  1935 Gulf of Mexico Dr Unit G7304, Longboat Key, FL 34228
• 

  

  /69

  $25,000 per month

  • 3 Beds
  • 3 Baths
  • 3,230 Sq Ft
  • House for Rent

  690 Old Compass Rd, Longboat Key, FL 34228

  Coveted lifestyle and location on one of the widest deep water canals on LONGBOAT KEY with direct access to Sarasota Bay with no bridges! This house has been totally renovated right down to the studs giving you 3,230 square feet of total luxury living. Meticulously maintained, this home has 3 bedrooms. The primary bedroom is en-suite with a king size bed, 2nd and 3rd bedrooms feature queen size

  Teresa Ribaudo JENNETTE PROPERTIES INC

  690 Old Compass Rd, Longboat Key, FL 34228
• 

  /2

  $775,000 Sold Oct 08, 2025

  • Land
  • 0.28 Acre
  • $2,767,857 per Acre

  • 164 Days On Market

  771 Broadway St, Longboat Key, FL 34228

  LOCATION ALERT!!! Build your dream home on this 12,000 sq ft vacant residential lot. This spacious lot offers a creative, vast playground of architectural possibilities and also those famous and coveted gorgeous, Gulf sunsets and sunrises. You are located in the heart of The Village in Longboat Key, convenient walking distance to fabulous restaurants like The Shore, Mar Vista and Whitney's. The

  Jason Sato SATO REAL ESTATE INC.

  771 Broadway St, Longboat Key, FL 34228
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  /38

  Est $1,410,947 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,470 Sq Ft

  2425 Gulf of Mexico Dr Unit 13B, Longboat Key, FL 34228

  2425 Gulf of Mexico Dr Unit 13B, Longboat Key, FL 34228
• 

  

  /73

  $5,225,000

  • 3 Beds
  • 3.5 Baths
  • 4,733 Sq Ft

  585 Gunwale Ln, Longboat Key, FL 34228

  Welcome to 585 Gunwale Lane, a rare, full-bayfront offering in the desirable community of Country Club Shores on southern end of Longboat Key. On a .36-acre bayfront parcel with 117 feet on Sarasota Bay and 123 feet on a deepwater canal, this residence is a boater’s paradise. A newer seawall and 58-foot dock (2022) with a 24,000-pound boat lift assure easy access to Sarasota Bay and the Gulf of

  Peter G. Laughlin PREMIER SOTHEBY'S INTERNATIONAL REALTY

  585 Gunwale Ln, Longboat Key, FL 34228
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  /52

  $19,975 per month

  • 4 Beds
  • 4 Baths
  • 4,236 Sq Ft
  • House for Rent

  5801 Gulf of Mexico Dr, Longboat Key, FL 34228

  Beach Access & Gulf Views From This Incredible Luxury Home on Longboat Key. Welcome to your own Gulf-front retreat on Longboat Key! This expansive 4-bedroom, 3-bath home offers over 4,200 square feet of living space designed for relaxation, entertaining, and soaking in stunning beach views. Inside, you’ll find an open living and dining area with vaulted ceilings and multi-level walls of windows

  Kevin Hase KEYRENTER SARASOTA PROPERTY MANAGEMENT

  5801 Gulf of Mexico Dr, Longboat Key, FL 34228
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  /2

  $640,000 Sold Oct 07, 2025

  • 1,393 Sq Ft
  • $459/SF
  • 11 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  4825 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  Fabulous Gulf-front views from this third-floor beachfront residence in The Westchester. Enjoy morning strolls on the beach, sunsets from your lanai, and island living in this spacious two-bedroom, two-bath plan. With panoramic views of the beach and the Gulf, you'll find nearly 1,400 square feet of thoughtfully designed living space featuring a Gulf-front lanai, generous living spaces, large

  Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  4825 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
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  /62

  Est $782,297 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 961 Sq Ft

  4401 Gulf of Mexico Dr Unit 706, Longboat Key, FL 34228

  4401 Gulf of Mexico Dr Unit 706, Longboat Key, FL 34228
• 

  

  /59

  $1,995,000

  • 2 Beds
  • 2 Baths
  • 1,468 Sq Ft

  2525 Gulf of Mexico Dr Unit 8D, Longboat Key, FL 34228

  It's all about the breathtaking direct Gulf of Mexico views and sweeping Sarasota Bay panoramas from this fully updated, highly desirable residence at Islands West. From the moment you enter, the blue-green waters of the Gulf of Mexico take center stage through floor to ceiling storm rated windows and sliders from every room. The light filled open plan was completely remodeled in 2020 and

  JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  2525 Gulf of Mexico Dr Unit 8D, Longboat Key, FL 34228
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  /73

  $10,000 per month

  • 6 Beds
  • 5.5 Baths
  • 4,676 Sq Ft
  • House for Rent

  614 Norton St, Longboat Key, FL 34228

  Experience the ultimate in coastal luxury with this exceptional residence on Longboat Key. Nestled along a canal with direct access to the Gulf, this expansive home is a dream for boating enthusiasts and those seeking a serene, upscale lifestyle.Key Features:-Prime Location: Situated on a canal with private dock and direct Gulf access—perfect for boating, fishing, or simply enjoying the

  Miranda Platt, PA RELAX REALTY GROUP INC

  614 Norton St, Longboat Key, FL 34228
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  /2

  $2,450,000 Sold Oct 07, 2025

  • 2,857 Sq Ft
  • $858/SF
  • 43 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1982

  260 N Shore Rd Unit 2, Longboat Key, FL 34228

  Welcome to 260 North Shore Road — a rare opportunity to own a beachfront townhome in the exclusive 360 Northenclave on the serene north end of Longboat Key. Designed by Tim Seibert, a founding figure of the Sarasota School of Architecture, this home is a masterclass in clean lines, natural light, and indoor-outdoor harmony.Spanning over 3,000 square feet, this 3-bedroom, 3-bathroom

  Reid Murphy DEVELOPERS REALTY LBK, INC

  260 N Shore Rd Unit 2, Longboat Key, FL 34228
• 

  

  /66

  Est $811,138 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
• 

  

  /75

  $1,195,000

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

  5055 Gulf of Mexico Dr Unit 331, Longboat Key, FL 34228

  Welcome to your coastal retreat in paradise — a stunning third-floor waterfront residence in Club Longboat Beach and Tennis, offering expansive Gulf views and one of the largest floor plans in the community. This exceptional 2-bedroom plus 3rd bedroom/study layout perfectly blends elegance, comfort, and functionality, ideal for full-time living or as a refined vacation escape. With 750 feet of

  Ryan Heers COLDWELL BANKER REALTY

  5055 Gulf of Mexico Dr Unit 331, Longboat Key, FL 34228
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  /56

  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Condo for Rent

  4360 Chatham Dr Unit 108, Longboat Key, FL 34228

  Newly renovated and elegantly designed 2-bedroom, 2-bathroom condo in the highly desirable Longboat Harbour Condominiums, located just 600 feet from the shore and a 3-minute walk to the beach. This fully furnished ground floor unit offers a modern open layout with scenic views, access to Sarasota Bay, and resort-style community amenities including four swimming pools (one located right

  Jorge Perez ROI AVE LLC

  4360 Chatham Dr Unit 108, Longboat Key, FL 34228
• 

  /2

  $1,150,000 Sold Oct 06, 2025

  • 2,448 Sq Ft
  • $470/SF
  • 55 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1984

  2103 Harbourside Dr Unit 1102, Longboat Key, FL 34228

  High and Dry, Beautifully Renovated, and Fully Furnished, this Stunning Villa is Move-In Ready! This single-story villa in prestigious Harbour Oaks offers nearly 2,500 square feet of light-filled living space with tasteful finishes and high-end furnishings hand selected by a designer. Elevated over 11 feet, the home remained untouched by flooding or hurricane damage—offering peace of mind in

  Nick Gard COLDWELL BANKER REALTY

  2103 Harbourside Dr Unit 1102, Longboat Key, FL 34228
• 

  

  /47

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 657 Sq Ft

  3710 Gulf of Mexico Dr Unit E13, Longboat Key, FL 34228

  3710 Gulf of Mexico Dr Unit E13, Longboat Key, FL 34228
• 

  

  /55

  $5,280,000

  • 4 Beds
  • 6 Baths
  • 4,145 Sq Ft

  5840 Gulf of Mexico Dr, Longboat Key, FL 34228

  Longboat Key Waterfront Estate with Rare Beach and Boating Access. Designed by Stofft Cooney Architects and built in 2022 by Perrone Construction, one of the Gulf Coast’s premier luxury builders, this stunning coastal residence is a rare offering that blends modern design, structural integrity, and an exceptional location. Positioned on the desirable northern end of Longboat Key, the home offers

  Toni Zarghami KW COASTAL LIVING III

  5840 Gulf of Mexico Dr, Longboat Key, FL 34228
• 

  

  /67

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • House for Rent

  4780 Gulf of Mexico Dr, Longboat Key, FL 34228

  Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January and February 2026! An opportunity that won’t last long. Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets directly across the street, with three beach access points — including private deeded beach access. Appreciate

  Debby McCaig COLDWELL BANKER REALTY

  4780 Gulf of Mexico Dr, Longboat Key, FL 34228
• 

  /2

  $1,850,000 Sold Oct 03, 2025

  • 1,880 Sq Ft
  • $984/SF
  • 124 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1993

  540 Gulf Bay Rd, Longboat Key, FL 34228

  SPECTACULAR LONGBOAT KEY BEACH COMPOUND WITH DEEDED ACCESS TO THE GULF OF MEXICO! This FULLY ELEVATED beach home has been meticulously maintained, offers top of the line finishes, and is located just a short 4 minute walk with PRIVATE DEEDED BEACH ACCESS to the sparkling waters of the Gulf on LONGBOAT KEY! Surrounded by Joan Durante Park, this property offers the ultimate in privacy and

  Brett Coady PINEYWOODS REALTY LLC

  540 Gulf Bay Rd, Longboat Key, FL 34228
• 

  

  /52

  Est $777,169 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
• 

  

  /69

  $2,500,000

  • 3 Beds
  • 3 Baths
  • 2,385 Sq Ft

  415 L Ambiance Dr Unit B202, Longboat Key, FL 34228

  A rare find — a 2-bedroom residence elegantly reconfigured with an architect’s vision to function as a 3-bedroom if desired. The second bedroom with custom Murphy beds accommodates up to three guests, while the office/den with a queen sleeper offers flexible living space. This residence is the crown jewel of coastal elegance — the epitome of refined luxury living at L’Ambiance, Longboat Key’s

  Judy Kepecz-Hays COLDWELL BANKER REALTY

  415 L Ambiance Dr Unit B202, Longboat Key, FL 34228
• 

  

  /35

  $5,500 per month

  • 2 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Condo for Rent

  3440 Gulf of Mexico Dr Unit 9, Longboat Key, FL 34228

  AVAILABLE Dec. 2025-April 2026, 2 mos. min. This is a second floor walk up, two bedroom and den, two bathroom unit with over 1,600 square feet of interior living space. There is a private screened balcony/lanai and aa staircase entrance to the front door of the unit. The unit has partial water views from the living room, dining room, den, and the screened balcony and exterior open balcony/lanai

  Brenda Cozy COLDWELL BANKER REALTY

  3440 Gulf of Mexico Dr Unit 9, Longboat Key, FL 34228
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  /2

  $6,000,000 Sold Oct 03, 2025

  • 3,130 Sq Ft
  • $1,917/SF
  • 99 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2024

  1591 Gulf of Mexico Dr Unit 511, Longboat Key, FL 34228

  Spectacular Gulf of Mexico and Sarasota Bay views from this elegant turnkey furnished two-bedroom corner residence. Designed and furnished by the prestigious Beasley and Henley Interior Design of Winter Park, Florida with bespoke details befitting a private St. Regis residence. The sellers invested over $650,000.00 on the furnishings for this showcase home. Every room is curated with the finest

  Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  1591 Gulf of Mexico Dr Unit 511, Longboat Key, FL 34228
• 

  

  /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
• 

  

  /47

  $2,100,000

  • 2 Beds
  • 2.5 Baths
  • 2,274 Sq Ft

  340 Gulf of Mexico Dr Unit 126, Longboat Key, FL 34228

  Rarely available Corner Residence! This very private Bayfront Southwest corner residence features 3 terraces. Experience resort-style living at Tangerine Bay Club, a gated sanctuary on the south end of Longboat Key. This impeccably maintained 2BR, plus office/Den, or 3-bedroom, 2.5-bath home offers 2,300 sq. ft. of refined living space with breathtaking views of Sarasota Bay and downtown, as well

  Judy Kepecz-Hays COLDWELL BANKER REALTY

  340 Gulf of Mexico Dr Unit 126, Longboat Key, FL 34228
• 

  

  /66

  $6,050 per month

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

  618 Bayport Way Unit 618, Longboat Key, FL 34228

  Escape to paradise with a stay in this newly renovated 2-bedroom, 2-bath second floor condominium at Bayport Beach & Tennis Club on Longboat Key. Perfectly positioned for your dream beach getaway, this condo blends comfort, style and unbeatable amenities. Bright, modern, and welcoming, this condo has been thoughtfully updated with all the comforts of home, including a king-size bed in the primary

  Alzira Meierling KELLER WILLIAMS ON THE WATER S

  618 Bayport Way Unit 618, Longboat Key, FL 34228
• 

  /2

  $253,000 Sold Oct 02, 2025

  • 1,427 Sq Ft
  • $177/SF
  • 110 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1969

  594 Spanish Dr S, Longboat Key, FL 34228

  Welcome to this 2-bedroom, 2-bath villa located in the highly desirable 55+ community of Spanish Main Yacht Club on the north end of Longboat Key. Offering the perfect blend of privacy, potential, and location, this villa is ideal as a full-time residence, seasonal getaway, or investment opportunity. Enjoy exclusive access to the community’s private marina and secluded beach, just a short stroll

  Amber Lynch COMPASS FLORIDA LLC

  594 Spanish Dr S, Longboat Key, FL 34228
• 

  

  /43

  Est $655,860 Not Listed For Sale

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

  4960 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228

  4960 Gulf of Mexico Dr Unit 205, Longboat Key, FL 34228
• 

  

  /41

  $1,350,000

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft

  603 Longboat Club Rd Unit 402N, Longboat Key, FL 34228

  Nestled behind the exclusive gates of the Longboat Key Club, Longboat Key Towers stands as one of the island’s most distinguished Gulf-front communities. Within the north tower, this elegant fourth-floor residence captures breathtaking views from sunrise to sunset — with two expansive balconies overlooking the shimmering Gulf of Mexico to the west and the rolling greens and bay waters to the

  Judy Kepecz-Hays COLDWELL BANKER REALTY

  603 Longboat Club Rd Unit 402N, Longboat Key, FL 34228
• 

  

  /42

  $10,000 per month

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

  2823 Gulf of Mexico Dr, Longboat Key, FL 34228

  Available now until December 31st, 2025. Booked January 1st, 2026 to May 31st, 2026. The 2026 Summer is available, see rates at end of this paragraph. Welcome to beachfront paradise on Longboat Key! This outstanding location offers a rare opportunity to enjoy coastal living with breathtaking views of the shoreline. Nestled along the pristine shores of Longboat Key, this three-bedroom,

  Michael Cella CELLA'S REAL ESTATE INC

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

  /2

  $485,000 Sold Oct 02, 2025

  • 928 Sq Ft
  • $523/SF
  • 111 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1974

  2045 Gulf of Mexico Dr Unit M1302, Longboat Key, FL 34228

  Walk right out to the beach from this beautifully updated 2 bedroom, 2 bath condominium in the amenity-rich community of Seaplace on Longboat Key's Gulf front; where residents enjoy a half-mile of private beach with lounge chairs and umbrellas, two heated pools with spas, kiddie pool, fitness center and sauna, updated clubhouse with kitchen and library, grilling areas, three Har-Tru tennis

  Sandra Endres COLDWELL BANKER REALTY

  2045 Gulf of Mexico Dr Unit M1302, Longboat Key, FL 34228
• 

  

  /78

  Est $753,544 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

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