Longboat Key, FL Homes

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  /37

  $799,000

  • Land
  • 0.15 Acre
  • $5,326,667 per Acre

  766 Saint Judes Dr N, Longboat Key, FL 34228

  Prime CANAL lot on beautiful Long Boat Key. l with 2 new working boat lifts installed in 2023 (10,000lb capacity & 13,000lb capacity)! Ready to be built on - lot has been cleared. New 100' sea wall installed in 2022. Deeded beach access to the gulf as well. Perfect location near amazing restaurants and beautiful beaches.

  

  Nikki Spirakis

  BRG REAL ESTATE INC

  (941) 688-9189

  766 Saint Judes Dr N, Longboat Key, FL 34228
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  /57

  $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 May 1, 2026 - December 12, 2026. Prefer 6+ Month RentalsBeautiful corner unit condo with an abundance of win.dows 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/pickleball court, shuffleboard, kayak

  4340 Falmouth Dr Unit 201, Longboat Key, FL 34228
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  $505,000 Sold Feb 24, 2025

  4440 Exeter Dr Unit 304, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft
  • Built 1970

  Last Sold Summary

  • 8% Below List Price
  • $509/SF
  • 38 Days On Market

  Current Estimated Value $507,534

  Last Listing Agent Malihe Karimi MICHAEL SAUNDERS & COMPANY

  4440 Exeter Dr Unit 304, Longboat Key, FL 34228
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  /24

  Est $1,148,031 Not Listed For Sale

  628 Lyons Ln, Longboat Key, FL 34228

  628 Lyons Ln, Longboat Key, FL 34228
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  /59

  $2,500,000

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

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

  Gulf-front enclave offers a rare blend of luxury, location, and lifestyle that transforms every day into a retreat. From the moment you step inside, you’re greeted by an atmosphere of refined elegance and architectural clarity—crafted for those who appreciate design as a way of life. This residence exudes sophistication with interiors envisioned by an internationally acclaimed designer,

  

  Judy Kepecz-Hays

  COLDWELL BANKER REALTY

  (941) 300-0171

  415 L Ambiance Dr Unit B202, Longboat Key, FL 34228
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  /20

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,896 Sq Ft
  • Condo for Rent

  2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  Absolutely stunning waterfront turnkey furnished rental property on Longboat Key. This unit features beautiful sunsets daily from your private balcony and there is a shared seating area facing east if you prefer sunrises. This spacious 2/2 split floor plan has been fully renovated and is tastefully furnished. The property boasts amenities such as a beachfront pool, workout room, tennis court, and

  Christian Higgins ANDRE LECLAIR PROPERTIES LLC

  2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
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  /2

  $2,050,000 Sold Mar 27, 2025

  524 Gunwale Ln, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 2,135 Sq Ft
  • Built 1966

  Last Sold Summary

  • 5% Below List Price
  • $960/SF
  • 20 Days On Market

  Current Estimated Value $1,937,893

  Last Listing Agent Judy Kepecz-Hays COLDWELL BANKER REALTY

  524 Gunwale Ln, Longboat Key, FL 34228
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  /17

  Est $194,657 Not Listed For Sale

  • Studio
  • 800 Sq Ft

  2600 Harbourside Dr Unit G-2, Longboat Key, FL 34228

  2600 Harbourside Dr Unit G-2, Longboat Key, FL 34228
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  /80

  $650,000

  • 2 Beds
  • 2 Baths
  • 1,192 Sq Ft

  1932 Harbourside Dr Unit 254, Longboat Key, FL 34228

  Bask in breathtaking views across Sarasota Bay to the sparkling downtown skyline from this beautifully updated 2-bedroom, 2-bath condo in the exclusive, guard-gated community of Bay Isles. Offered turnkey furnished, this top-floor residence in a mid-rise five-story building combines comfort, style, and peace of mind with secure entry and 24/7 guarded access. Inside, the kitchen showcases granite

  

  Beverly St Hilaire

  MICHAEL SAUNDERS & COMPANY

  (941) 390-0836

  1932 Harbourside Dr Unit 254, Longboat Key, FL 34228
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  /65

  $85,000 per month

  • 4 Beds
  • 4.5 Baths
  • 5,334 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228

  There are moments in life that stop you mid-thought. Moments so immersive that words struggle to keep up with what you’re feeling. This penthouse is one of those moments. Offered to the public for the first time, this four-bedroom residence sits high above the Gulf of Mexico, where light, water, and horizon become part of everyday life. A private elevator opens directly into the home, setting the

  Inbal August DOUGLAS ELLIMAN

  1591 Gulf of Mexico Dr Unit 619, Longboat Key, FL 34228
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  /2

  $1,040,000 Sold Mar 06, 2025

  1065 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft
  • Built 1981

  Last Sold Summary

  • 13% Below List Price
  • $572/SF
  • 50 Days On Market

  Current Estimated Value $977,713

  Last Listing Agent Moriah Taliaferro PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1065 Gulf of Mexico Dr Unit 105, Longboat Key, FL 34228
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  /2

  Est $1,009,203 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft

  1125 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

  1125 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
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  /69

  $1,950,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,375 Sq Ft

  545 Sanctuary Dr Unit B206, Longboat Key, FL 34228

  Under contract-accepting backup offers. EXCITING NEWS!! NEW ROOF! NO FINANCIAL OBLIGATION TO THE BUYERS AS THE ASSESSMENT HAS BEEN PAID IN FULL! Welcome to a lifestyle that surpasses all expectations in the Sanctuary community, where luxury living meets breathtaking views! Nestled on the 2nd flr, this 3BR, 3BA condo unit offers a haven of tranquility & an array of amenities. Step inside, and

  Andrew Duncan LPT REALTY LLC

  545 Sanctuary Dr Unit B206, Longboat Key, FL 34228
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  /15

  $2,450 per month

  • 2 Beds
  • 2 Baths
  • 1,046 Sq Ft
  • Condo for Rent

  3806 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  This is a 2 bedroom 2 bathroom furnished, third floor condo located in waterfront Beach Harbor Club with views of Buttonwood Bayou! The living room and both bedrooms feature a large window overlooking the courtyard, swimming pool, and the Bayou. There is carpet throughout the living area and bedrooms and tile flooring in the kitchen. The kitchen has granite counter tops, white appliances, and a

  Todd Roughton SARASOTA MANAGEMENT & LEASING

  3806 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
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  /2

  $1,175,000 Sold Apr 04, 2025

  4725 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft
  • Built 1974

  Last Sold Summary

  • 10% Below List Price
  • $1,139/SF
  • 88 Days On Market

  Current Estimated Value $1,077,321

  Last Listing Agent Isy Bundziak HOT HOMES REALTY

  4725 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228
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  /51

  Est $434,049 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 912 Sq Ft

  4720 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228

  4720 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
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  /67

  $4,490,000

  • 4 Beds
  • 7 Baths
  • 4,674 Sq Ft

  761 Norton St, Longboat Key, FL 34228

  Tucked along a quiet canal in Longboat Key’s Sleepy Lagoon Park, 761 Norton Street delivers the kind of waterfront lifestyle that’s increasingly rare—equal parts boating-centric, resort-style, and built for hosting at scale. With 4 bedrooms, 4 full baths, 3 half baths, and 4,674 square feet under air, the home is thoughtfully designed for those who want space and flexibility without sacrificing

  Joel Schemmel DOUGLAS ELLIMAN

  761 Norton St, Longboat Key, FL 34228
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  /26

  $3,000 per month

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Condo for Rent

  554 Sutton Place, Longboat Key, FL 34228

  nnual Unfurnished Rental. Now available on beautiful Longboat Key! This spacious second-floor, two-bedroom residence combines comfort with classic coastal living, featuring a screened lanai and a large attached garage with ample storage. Wake up to stunning Bayfront sunrises and end your day with spectacular Gulf sunsets—all from your home in Sutton Place, a sought-after Gulf-to-Bay community

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  554 Sutton Place, Longboat Key, FL 34228
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  /2

  $2,300,000 Sold Apr 30, 2025

  240 Sands Point Rd Unit 4507, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,619 Sq Ft
  • Built 1982

  Last Sold Summary

  • 15% Below List Price
  • $1,421/SF
  • 275 Days On Market

  Current Estimated Value $2,218,306

  Last Listing Agent Leticia Diaz KELLER WILLIAMS ON THE WATER

  240 Sands Point Rd Unit 4507, Longboat Key, FL 34228
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  /2

  Est $2,941,810 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,667 Sq Ft

  1281 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228

  1281 Gulf of Mexico Dr Unit 1005, Longboat Key, FL 34228
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  /82

  $3,595,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,166 Sq Ft

  3540 Mistletoe Ln, Longboat Key, FL 34228

  Under contract-accepting backup offers. This spectacular direct bayfront residence is offered fully furnished and showcases a thoughtful, top-to-bottom transformation embodying refined coastal luxury. With panoramic views across Sarasota Bay and a deep-water dock equipped with a lift, this four-bedroom home is a true boater’s retreat, offering effortless access to the Bay and the Gulf of Mexico

  Renee Preininger SARASOTA TRUST REALTY COMPANY

  3540 Mistletoe Ln, Longboat Key, FL 34228
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  /55

  $3,300 per month

  • 1 Bed
  • 1 Bath
  • 798 Sq Ft
  • Apartment for Rent

  3740 Gulf of Mexico Dr Unit 114, Longboat Key, FL 34228

  Stunning Bayfront and Marina views, this is a rare opportunity for a 1 bedroom, 1 bath, FURNISHED in a 55 + community on Longboat key . This is a beautifully designed and outfitted villa in the community of Twin Shores-located Mid Key(Close to both St. Armand's Circle and Anna Maria Island). Not only are you Sitting within Steps to Panoramic Views of the Bay, you have private DEEDED beach access

  Joseph Patoray FINE PROPERTIES

  3740 Gulf of Mexico Dr Unit 114, Longboat Key, FL 34228
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  /2

  $62,500 Sold Jun 20, 2025

  408 Gulf of Mexico Dr Unit 1222, Longboat Key, FL 34228

  Last Sold Summary

  • 9% Below List Price
  • 6 Days On Market

  Current Estimated Value $61,048

  Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

  408 Gulf of Mexico Dr Unit 1222, Longboat Key, FL 34228
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  /48

  Est $2,125,453 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,499 Sq Ft

  6957 Longboat Dr S, Longboat Key, FL 34228

  6957 Longboat Dr S, Longboat Key, FL 34228
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  /89

  $4,990,000

  • 3 Beds
  • 3.5 Baths
  • 3,582 Sq Ft

  4127 Gulf of Mexico Dr Unit N101, Longboat Key, FL 34228

  Where every day unfolds like a private Gulf Coast retreat. Set directly along the shimmering waters of the Gulf of Mexico, this refined 3-bedroom, 31⁄2-bath residence at La Firenza offers an elevated expression of coastal living on Longboat Key. Encompassing approximately 3,582 square feet, the home pairs timeless elegance with a gracious, livable scale—designed to celebrate light, views, and an

  Sue Wolverton DOUGLAS ELLIMAN

  4127 Gulf of Mexico Dr Unit N101, Longboat Key, FL 34228
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  /70

  $10,000 per month

  • 4 Beds
  • 3.5 Baths
  • 2,600 Sq Ft
  • House for Rent

  700 Lands End Dr Unit 2, Longboat Key, FL 34228

  Experience refined coastal living in this fully furnished 4-bedroom, 4-bath residence ideally positioned within a private, gated enclave on Longboat Key, tucked beneath majestic banyan trees for exceptional privacy and tranquility. Designed to embrace Florida’s indoor-outdoor lifestyle, the home welcomes you through a stunning atrium entry, where natural light filters through lush tropical

  Jenn Spinelli THE AGENCY FL

  700 Lands End Dr Unit 2, Longboat Key, FL 34228
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  /2

  $1,766,000 Sold Feb 04, 2026

  3060 Grand Bay Blvd Unit 175, Longboat Key, FL 34228

  • 3 Beds
  • 2.5 Baths
  • 2,143 Sq Ft
  • Built 1994

  Last Sold Summary

  • 9% Below List Price
  • $824/SF
  • 86 Days On Market

  Last Listing Agent Judy Mitchell PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3060 Grand Bay Blvd Unit 175, Longboat Key, FL 34228
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  /19

  Est $173,953 Not Listed For Sale

  • Studio
  • 1,200 Sq Ft

  2600 Harbourside Dr Unit H-06, Longboat Key, FL 34228

  2600 Harbourside Dr Unit H-06, Longboat Key, FL 34228
• 

  

  /79

  $8,500,000

  • 5 Beds
  • 5.5 Baths
  • 6,125 Sq Ft

  501 Harbor Point Rd, Longboat Key, FL 34228

  Rare opportunity to acquire completely remodeled waterfront residence (Finished in 2023) on Sarasota’s most prestigious barrier island of Longboat Key, in the coveted Harbors enclave of Bay Isles. Orchestrating exceptional style, comfort, and barefoot elegance, this five-bedroom home stirs the senses. Completely redesigned by renowned architect Clifford Scholz, construction was completed in

  Rich Polese COMPASS FLORIDA LLC

  501 Harbor Point Rd, Longboat Key, FL 34228
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  /69

  $40,000 per month

  • 2 Beds
  • 2.5 Baths
  • 3,130 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228

  An exceptional opportunity to lease the largest two-bedroom residence at the prestigious St. Regis Longboat Key. This premier corner home offers sweeping panoramic views of the Gulf of Mexico, Sarasota Bay, lush resort grounds, and the tropical saltwater lagoon, all enjoyed from an expansive wraparound terrace. Bathed in natural light, the spacious living area is ideal for entertaining and

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1591 Gulf of Mexico Dr Unit 410, Longboat Key, FL 34228
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  /2

  $200,000 Sold Jun 27, 2025

  2800 Harbourside Dr Unit M-01, Longboat Key, FL 34228

  Last Sold Summary

  • 20% Below List Price
  • 507 Days On Market

  Current Estimated Value $194,965

  Last Listing Agent Jennifer Wilson LBRE LLC

  2800 Harbourside Dr Unit M-01, Longboat Key, FL 34228
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  /58

  Est $1,026,701 Not Listed For Sale

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

  4401 Gulf of Mexico Dr Unit 701, Longboat Key, FL 34228

  4401 Gulf of Mexico Dr Unit 701, Longboat Key, FL 34228
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  /64

  $9,700,000

  • 4 Beds
  • 5 Baths
  • 5,245 Sq Ft

  560 Harbor Point Rd, Longboat Key, FL 34228

  Exquisite Palladian-Style Waterfront Estate Located on the serene shores of Sarasota Bay, this home epitomizes elegance and sophistication. Designed by Cliff Scholz and meticulously crafted by Murray Homes, this, 5,300-square-foot masterpiece is situated in a double-gated community offering unparalleled privacy and exclusivity. Perched at the end of a quiet cul-de-sac, the property boasts almost

  Jonathan Fox MICHAEL SAUNDERS & COMPANY

  560 Harbor Point Rd, Longboat Key, FL 34228
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  /28

  $2,500 per month

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

  3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228

  1-bed, 1-bath seasonal 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 around on

  Dakota Magnus FLORIDA GALLERY REAL ESTATE

  3808 Gulf of Mexico Dr Unit E205, Longboat Key, FL 34228
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  /2

  $3,900,000 Sold Mar 31, 2025

  675 Longboat Club Rd Unit 22A, Longboat Key, FL 34228

  • 3 Beds
  • 4 Baths
  • 3,564 Sq Ft
  • Built 1996

  Last Sold Summary

  • 13% Below List Price
  • $1,094/SF
  • 38 Days On Market

  Current Estimated Value $3,694,323

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  675 Longboat Club Rd Unit 22A, Longboat Key, FL 34228
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  /66

  Est $3,287,467 Not Listed For Sale

  • 3 Beds
  • 4.5 Baths
  • 3,687 Sq Ft

  3521 Bayou Pointe, Longboat Key, FL 34228

  3521 Bayou Pointe, Longboat Key, FL 34228
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  /28

  $3,275,000 Pending

  • 4 Beds
  • 5 Baths
  • 3,313 Sq Ft

  601 Triton Bend, Longboat Key, FL 34228

  Under contract-accepting backup offers. Perfectly positioned mid-key and just 500 feet from the shell-filled shoreline, this beautiful home with a fenced-in yard spans two levels and features a separate guest house. Enter the property through the interior courtyard, past the covered al fresco dining area, to the soothing sound of a waterfall flowing from the pergola into the heated pool. Sunlight

  Gina Ursini BRISTA REALTY LLC

  601 Triton Bend, Longboat Key, FL 34228
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  /59

  $10,000 per month

  • 3 Beds
  • 5 Baths
  • 2,908 Sq Ft
  • House for Rent

  3111 Bayou Sound, Longboat Key, FL 34228

  LOCATION, LOCATION, LOCATION. BEAUTIFUL TURNKEY FURNISHED SINGLE FAMILY HOME available in the sought after community of Bay Isles is available to rent. This lovely light, bright 3 bedroom plus 3 bathroom, two half bathroom home boasts 2,908 square feet, double primary bedrooms, living room/dining room combination, loft/den space and much much more. The home has been fully painted and newly

  C. Alison Hunter JENNETTE PROPERTIES INC

  3111 Bayou Sound, Longboat Key, FL 34228
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  /2

  $10,250,000 Sold May 09, 2025

  801 Longboat Club Rd, Longboat Key, FL 34228

  • 5 Beds
  • 5.5 Baths
  • 6,923 Sq Ft
  • Built 1993

  Last Sold Summary

  • 14% Below List Price
  • $1,481/SF
  • 76 Days On Market

  Current Estimated Value $9,190,499

  Last Listing Agent Kim Ogilvie MICHAEL SAUNDERS & COMPANY

  801 Longboat Club Rd, Longboat Key, FL 34228
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  /60

  Est $1,601,229 Not Listed For Sale

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

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

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

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