Longboat Key, FL Homes

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  $699,000

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

  1065 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

  One or more photo(s) has been virtually staged. One or more video(s) was virtually staged. Sunny and rarely available 2-bedroom, 2-bath corner residence in BeachPlace III on Longboat Key. This desirable end unit offers a wraparound terrace and open views of lush tropical landscaping, the Longboat Key Club’s Links Golf Course, and partial Gulf views—providing excellent natural light and a true

  John Esser KELLER WILLIAMS ON THE WATER S

  1065 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
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  /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

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  1591 Gulf of Mexico Dr Unit 315, Longboat Key, FL 34228
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  $960,000 Sold Jan 29, 2025

  4485 Gulf of Mexico Dr Unit 803, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,022 Sq Ft
  • Built 1973

  Last Sold Summary

  • 3% Below List Price
  • $939/SF
  • 36 Days On Market

  Current Estimated Value $871,108

  Last Listing Agent Debra Lichter SARASOTA BEACH TO BAY INC

  4485 Gulf of Mexico Dr Unit 803, Longboat Key, FL 34228
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  /18

  Est $222,245 Not Listed For Sale

  • Studio
  • 1,155 Sq Ft

  2600 Harbourside Dr Unit C-10, Longboat Key, FL 34228

  2600 Harbourside Dr Unit C-10, Longboat Key, FL 34228
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  /55

  $1,495,000

  • 3 Beds
  • 3.5 Baths
  • 3,239 Sq Ft

  3543 Mistletoe Ln, Longboat Key, FL 34228

  Located in the gated waterfront community of Coreys Landing within Bay Isles, this beautifully maintained 3BR residence offers refined design, comfort, and privacy. A paver walkway and lush tropical landscaping lead to the home’s centerpiece - a private courtyard pool surrounded by high privacy walls and tropical foliage, creating a tranquil space for relaxing or entertaining. The floor plan

  Bruce Myer COLDWELL BANKER REALTY

  3543 Mistletoe Ln, 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
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  $739,000 Sold Jun 18, 2025

  1945 Gulf of Mexico Dr Unit M2313, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,265 Sq Ft
  • Built 1978

  Last Sold Summary

  • $584/SF
  • 1 Day On Market

  Current Estimated Value $702,601

  Last Listing Agent Bruce Meyer MICHAEL SAUNDERS & COMPANY

  1945 Gulf of Mexico Dr Unit M2313, Longboat Key, FL 34228
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  /48

  Est $2,354,382 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,284 Sq Ft

  210 Sands Point Rd Unit 2603/04, Longboat Key, FL 34228

  210 Sands Point Rd Unit 2603/04, Longboat Key, FL 34228
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  /28

  $395,000

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

  620 Spanish Dr N, Longboat Key, FL 34228

  Don't miss this rare opportunity to own a renovated standalone villa with a lake view on Longboat Key! This very light, bright, and charming 2 bedroom 2 bath home is almost ready for occupancy at an exceptionally low price. As you enter the home, you can see a lovely lake view through the large back windows. The rear, shady, landscaped patio is a perfect place to relax throughout the day and

  Adrienne Scott MICHAEL SAUNDERS & COMPANY

  620 Spanish Dr N, Longboat Key, FL 34228
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  /46

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,235 Sq Ft
  • Condo for Rent

  2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228

  RARELY AVAILABLE! This absolutely gorgeous fully furnished 2BR/2BA Condo at Islander Club – Just steps from the Beach! Start living the island lifestyle in this beautifully updated, furnished 2-bedroom, 2-bath condo at the Islander Club on South Longboat Key! This turnkey rental is ready for immediate enjoyment—just bring your suitcase. Enjoy a bright, open layout with floor-to-ceiling hurricane

  Michele Conn PREFERRED SHORE LLC

  2295 Gulf of Mexico Dr Unit 55, Longboat Key, FL 34228
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  $305,000 Sold Mar 05, 2025

  569 Sutton Place, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,198 Sq Ft
  • Built 1972

  Last Sold Summary

  • 42% Below List Price
  • $255/SF
  • 165 Days On Market

  Current Estimated Value $321,954

  Last Listing Agent Bruce Myer COLDWELL BANKER REALTY

  569 Sutton Place, Longboat Key, FL 34228
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  /29

  Est $1,147,491 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,859 Sq Ft

  1445 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

  1445 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
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  /67

  $750,000

  • 2 Beds
  • 2.5 Baths
  • 1,350 Sq Ft

  490 N Shore Rd Unit 6, Longboat Key, FL 34228

  This rare offering is all about the one-of-a-kind BREATHTAKING VIEWS overlooking multiple waterways across Greer island, towards the Intracoastal and out to the gorgeous Gulf of Mexico sunsets! Situated on the quiet north end of Longboat Key in a small, waterfront, boutique midrise building containing only 9 residences: this is island living at its best! It features two bedrooms and 2 and a half

  JoDene Moneuse MICHAEL SAUNDERS & COMPANY

  490 N Shore Rd Unit 6, Longboat Key, FL 34228
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  $3,000 per month

  • 2 Beds
  • 2 Baths
  • 928 Sq Ft
  • Condo for Rent

  1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228

  LONGBOAT KEY "SEAPLACE" CONDOMINIUM LOCATED ON THE GULF SIDE. AVAILABLE DEC 2025 & JAN 2026 AT $3,000/MONTH. UTILITIES INCLUDED. 2 MONTH MINIMUM REQUIRED PER HOA.BOOKED FOR FEB-APRIL 2026. Immaculate, Turnkey Furnished 2 bedrooms/2-bathroom condo on the 4th floor, located in the sought after Seaplace, a resort style community on the beautiful Barrier Island of Longboat Key. Upon entering the

  Chrissie Cummings JENNETTE PROPERTIES INC

  1945 Gulf of Mexico Dr Unit M2402, Longboat Key, FL 34228
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  $475,000 Sold Jul 25, 2025

  6750 Gulf of Mexico Dr Unit 153, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,441 Sq Ft
  • Built 1969

  Last Sold Summary

  • 32% Below List Price
  • $330/SF
  • 163 Days On Market

  Current Estimated Value $493,078

  Last Listing Agent Shayla Twit CORCORAN DWELLINGS REALTY

  6750 Gulf of Mexico Dr Unit 153, Longboat Key, FL 34228
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  /42

  Est $840,538 Not Listed For Sale

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

  1085 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

  1085 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
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  $2,895,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,804 Sq Ft

  6473 Gulf of Mexico Dr, Longboat Key, FL 34228

  Under contract-accepting backup offers. Outstanding opportunity to own an elevated pool home with beautiful views of the sparkling Gulf of Mexico on the highly sought-after north end of Longboat Key. This 3-bedroom, 2.5-bath Key West–style residence is ideally positioned on an oversized 19,400-sq.-ft. lot that stretches from Gulf of Mexico Drive to Gulfside Road—just steps from a pristine,

  Judy Kepecz-Hays COLDWELL BANKER REALTY

  6473 Gulf of Mexico Dr, Longboat Key, FL 34228
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  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 1,133 Sq Ft
  • Condo for Rent

  3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228

  2-bed, 2-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

  3802 Gulf of Mexico Dr Unit 207, Longboat Key, FL 34228
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  $1,420,000 Sold Aug 13, 2025

  455 Longboat Club Rd Unit 407, Longboat Key, FL 34228

  • 3 Beds
  • 3 Baths
  • 2,410 Sq Ft
  • Built 1990

  Last Sold Summary

  • 25% Below List Price
  • $589/SF
  • 104 Days On Market

  Current Estimated Value $1,449,641

  Last Listing Agent Stacy Hanan MICHAEL SAUNDERS & COMPANY

  455 Longboat Club Rd Unit 407, Longboat Key, FL 34228
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  /18

  Est $348,057 Not Listed For Sale

  • Studio

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

  2600 Harbourside Dr Unit L-08, Longboat Key, FL 34228
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  /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
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  /45

  $10,995 per month

  • 3 Beds
  • 2.5 Baths
  • 2,396 Sq Ft
  • House for Rent

  2339 Harbour Oaks Dr, Longboat Key, FL 34228

  Seasonal/short term rental on Longboat Key Beautifully renovated 3 bedroom 2 1/2 bathroom villa right on the golf course in prestigious, guard gated, Bay Isles. This spacious light filled delight has vaulted ceilings with sky lights, and new high impact windows and doors. The open floor plan is perfect for family time and entertaining. The kitchen is very large and has solid cherry wood

  Henry Rossi RENT SARASOTA

  2339 Harbour Oaks Dr, Longboat Key, FL 34228
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  $750,000 Sold Jul 29, 2025

  765 Saint Judes Dr N, Longboat Key, FL 34228

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 1963

  Last Sold Summary

  • 23% Below List Price
  • $395/SF
  • 136 Days On Market

  Current Estimated Value $770,719

  Last Listing Agent Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

  765 Saint Judes Dr N, Longboat Key, FL 34228
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  /2

  Est $660,686 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,453 Sq Ft

  5260 Gulf of Mexico Dr Unit 412, Longboat Key, FL 34228

  5260 Gulf of Mexico Dr Unit 412, Longboat Key, FL 34228
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  /5

  $43,500

  408 Gulf of Mexico Dr Unit 2112, Longboat Key, FL 34228

  Welcome to Slip #2112 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This slip accommodates boats up to 23'6''Lx8'6''Wx7'2''H (No T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  408 Gulf of Mexico Dr Unit 2112, Longboat Key, FL 34228
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  $12,000 per month

  • 3 Beds
  • 3 Baths
  • 2,250 Sq Ft
  • Condo for Rent

  3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228

  OPEN for 2026 SEASON Reservation. LBK SARASOTA LUXURY RENTAL in Paradise at GRAND BAY. This STUNNING 7th floor condominium has both sweeping WATER VIEWS of SARASOTA BAY views. Check in and enjoy the spectacular SUNSETS ON THE GULF of MEXICO. Like NEW, this beautifully designed three bedroom luxury residence has just completed a major updating remodeling with all new designer furniture and

  Patrice Ivan WAGNER REALTY

  3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
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  $108,000 Sold Sep 30, 2025

  72 Main Street Dr, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 780 Sq Ft
  • Built 1965

  Last Sold Summary

  • $138/SF

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  72 Main Street Dr, Longboat Key, FL 34228
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  /28

  Est $1,244,753 Not Listed For Sale

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

  1125 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228

  1125 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
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  $1,495,000

  • 3 Beds
  • 2 Baths
  • 1,581 Sq Ft

  691 Gulf Bay Rd, Longboat Key, FL 34228

  Experience the best of Florida’s Gulf Coast in this remodeled and elevated single-family home, ideally located on a quiet street that ends at Sarasota Bay and includes deeded beach access. Surrounded by the tropical beauty of Joan M. Durante Park’s nature preserve, this residence blends modern coastal design with the serenity of island living.Inside, an open-concept floor plan welcomes

  Angela Scott MICHAEL SAUNDERS & COMPANY

  691 Gulf Bay Rd, Longboat Key, FL 34228
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  $18,000 per month

  • 2 Beds
  • 2.5 Baths
  • 2,143 Sq Ft
  • Condo for Rent

  1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228

  The Residences at The St. Regis Longboat Key offer an exceptional blend of ultra-luxury living and world-class resort amenities on the pristine shores of the Gulf of Mexico. This exclusive beachfront community features exquisitely designed residences with soaring ceilings, floor-to-ceiling glass doors, and panoramic sunrise-to-sunset views. The gourmet kitchen showcases Wolf and Sub-Zero

  Melissa Gissinger MICHAEL SAUNDERS & COMPANY

  1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
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  $1,465,000 Sold Aug 28, 2025

  501 Reclinata Dr, Longboat Key, FL 34228

  • 3 Beds
  • 3.5 Baths
  • 2,784 Sq Ft
  • Built 2002

  Last Sold Summary

  • 18% Below List Price
  • $526/SF
  • 160 Days On Market

  Current Estimated Value $1,531,572

  Last Listing Agent Barbara Najmy STARZ REAL ESTATE, LLC

  501 Reclinata Dr, Longboat Key, FL 34228
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  /69

  Est $674,011 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,298 Sq Ft

  4140 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228

  4140 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
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  /45

  $999,500

  • 3 Beds
  • 2.5 Baths
  • 2,219 Sq Ft

  2367 Harbour Oaks Dr, Longboat Key, FL 34228

  Lives like a single family home! This 3 bedroom, 2 1/2 bath villa with over 2,200 sq.ft and an attached 2-car garage offers all the privacy and convenience of a private home and all the convenience of a maintenance free community. Located on #2 hole of the White Egret course on the Harbourside Golf Course in the Longboat Key Country Club. This home is in a secure gated community with only 42

  Sandra Endres COLDWELL BANKER REALTY

  2367 Harbour Oaks Dr, Longboat Key, FL 34228
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  $14,000 per month

  • 4 Beds
  • 3.5 Baths
  • 3,268 Sq Ft
  • House for Rent

  531 Birdie Ln, Longboat Key, FL 34228

  Annual Rental – Stunning Waterfront Home in Country Club Shores on Longboat Key. Experience the best of waterfront living in this beautiful 4-bedroom, 3.5-bathroom home located in the sought-after Country Club Shores community on Longboat Key. This spacious and elegant residence offers breathtaking canal views, luxurious amenities, and direct boating access and boat lift. This exceptional home

  Karie Gorgone WAGNER REALTY

  531 Birdie Ln, Longboat Key, FL 34228
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  $1,400,000 Sold Dec 03, 2025

  3115 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  • 3 Beds
  • 2 Baths
  • 1,433 Sq Ft
  • Built 1974

  Last Sold Summary

  • 7% Below List Price
  • $977/SF
  • 6 Days On Market

  Last Listing Agent Ellen Kirkegaard PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3115 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
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  /48

  Est $919,626 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,366 Sq Ft

  1485 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

  1485 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
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  /86

  $749,000

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft

  4350 Chatham Dr Unit 208, Longboat Key, FL 34228

  NEWLY REMODELED • COASTAL LUXURY RESIDENCELongboat Harbour • Unit 208 | Corner End Unit • Bay & Harbour Views.Welcome to an exquisite, newly remodeled second-floor corner residence in the highly sought-after Longboat Harbour community. Reimagined with sophisticated coastal design, this light-filled home captures sweeping views of Sarasota Bay and Longboat Harbour—creating a serene

  Billie Chipain COLDWELL BANKER REALTY

  4350 Chatham Dr Unit 208, Longboat Key, FL 34228
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  $4,000 per month

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

  3810 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

  1-bed, 1-bath 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 community

  Dakota Magnus FLORIDA GALLERY REAL ESTATE

  3810 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228
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  $1,450,000 Sold Jan 29, 2025

  5635 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228

  • 2 Beds
  • 2 Baths
  • 1,786 Sq Ft
  • Built 1980

  Last Sold Summary

  • 14% Below List Price
  • $812/SF
  • 13 Days On Market

  Current Estimated Value $1,239,604

  Last Listing Agent Derek Patti NEXTHOME EXCELLENCE

  5635 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228
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  Est $803,966 Not Listed For Sale

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

  1065 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

  1065 Gulf of Mexico Dr Unit 401, Longboat Key, FL 34228

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