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32 Properties Available
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$2,799,000
Single Family Home
311 FIREHOUSE CT, Longboat Key, FL 34228
This is what living on the West Coast of Florida is all about. Elevated and elegantly designed, this custom home sits we...
Listed by Kathy Harman MICHAEL SAUNDERS & COMPANY


$725,000
Condo
4500 GULF OF MEXICO DR #202, Longboat Key, FL 34228
Wake up to shimmering Bay views and peaceful marina life in this updated, turnkey furnished, 2-bed, 2-bath Longboat Key ...
Listed by Sharon Austin PREMIER SOTHEBY'S INTERNATIONAL REALTY


$695,000
Condo
4234 GULF OF MEXICO DR #D1, Longboat Key, FL 34228
Gorgeous coastal renovation, waterfront location, deeded beach, pet-friendly, and more. Enjoy the larger D1 plan, offeri...
Listed by Michael Seamon PREMIER SOTHEBY'S INTERNATIONAL REALTY


$4,900
Condo
3806 GULF OF MEXICO DR #C310, Longboat Key, FL 34228
Longboat Key vacation rental! You will love this wonderfully updated and tastefully furnished two-bedroom, two-bath thir...
Listed by Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY


$1,199,000
Condo
1425 GULF OF MEXICO DR #208, Longboat Key, FL 34228
Unit 208 is the largest 3-bedroom unit in this stack located in a building that is an easy walk to the beach and the poo...
Listed by Judy Mitchell PREMIER SOTHEBY'S INTERNATIONAL REALTY


$1,023,000
Single Family Home
2323 HARBOUR OAKS DR, Longboat Key, FL 34228
Welcome to 2323 Harbour Oaks Drive, a light-filled villa with a wide-open layout and peaceful vistas overlooking the Lon...
Listed by Steven Moore MICHAEL SAUNDERS & COMPANY


$595,000
Condo
4320 FALMOUTH DR #301, Longboat Key, FL 34228
Under contract-accepting backup offers. Experience true Bay-to-Gulf living with exclusive access to Sarasota Bay and the...
Listed by Kevin Tai PREFERRED SHORE LLC


$1,749,000
Condo
1211 GULF OF MEXICO DR #301, Longboat Key, FL 34228
Rarely available north-side corner residence at The Promenade showcases panoramic views of the Gulf of Mexico, Sarasota ...
Listed by Ryan Ackerman, PA COLDWELL BANKER REALTY


$699,000
Condo
1065 GULF OF MEXICO DR #201, Longboat Key, FL 34228
One or more photo(s) has been virtually staged. One or more video(s) was virtually staged. Welcome to coastal living at ...
Listed by John Esser KELLER WILLIAMS ON THE WATER S


$4,895,000
Single Family Home
530 DE NARVAEZ DR, Longboat Key, FL 34228
New Construction - Discover the epitome of waterfront luxury with this newly built home in the heart of Longboat Key—com...
Listed by Joshua Freed PREFERRED SHORE LLC


$620,000
Condo
1912 HARBOURSIDE DR #602, Longboat Key, FL 34228
Discover the ideal blend of comfort, convenience and coastal charm in this beautifully furnished townhouse in Fairway Ba...
Listed by Judy Mitchell PREMIER SOTHEBY'S INTERNATIONAL REALTY


$1,595,000
Condo
3060 GRAND BAY BLVD #182, Longboat Key, FL 34228
Soaring Sarasota Bay and Gulf of Mexico views from every room of this 8th floor residence at Grand Bay. This 2-bedroom +...
Listed by Ryan Ackerman, PA COLDWELL BANKER REALTY


$750,000
Condo
450 GULF OF MEXICO DR #B207, Longboat Key, FL 34228
Where can you get an exquisite 3 BEDROOM Waterfront Condo on the Coveted South End of Longboat Key under 800,000? Discov...
Listed by Mairead Smialek COLDWELL BANKER REALTY


$295,000
Condo
3806 GULF OF MEXICO DR #C208, Longboat Key, FL 34228
Discover coastal living at its finest with this charming condominium located on Gulf of Mexico Dr, Longboat Key. This re...
Listed by Steven Koleno BEYCOME OF FLORIDA LLC


$7,000
Condo
5757 GULF OF MEXICO DR #204, Longboat Key, FL 34228
Beautiful completely remodeled 2-bedroom, 2-bathroom Tropical Oasis on Longboat Key. Relax and enjoy the Florida lifesty...
Listed by Roxanne Klopp JENNETTE PROPERTIES, INC.


$2,090,000
Single Family Home
3617 FAIR OAKS PL, Longboat Key, FL 34228
One or more photo(s) has been virtually staged. Situated in the highly sought-after maintenance-free community of Queens...
Listed by Ryan Ackerman, PA COLDWELL BANKER REALTY


$859,000
Townhouse
1926 HARBOURSIDE DR #1302, Longboat Key, FL 34228
GATED, DEEDED PRIVATE BEACH ACCESS! This is a rare thing to be found on the keys! The main level with plantation shutter...
Listed by Stephen Hachey FLAT FEE MLS REALTY


$625,000
Single Family Home
755 SAINT JUDES DR N, Longboat Key, FL 34228
This property s a STEAL! Motivated seller has reduced this waterfront property far below any other property on Longboat ...
Listed by Ian Schmitzerle MICHAEL SAUNDERS & COMPANY


$2,100,000
Condo
2165 GULF OF MEXICO DR #114, Longboat Key, FL 34228
Enjoy Sunsets and experience direct beachfront living with stunning Gulf views on South Longboat Key in this exceptional...
Listed by Judy Kepecz-Hays COLDWELL BANKER REALTY


$14,000
Single Family Home
830 TARAWITT DR, Longboat Key, FL 34228
Luxury and Coastal Elegance! This Stunning Turnkey Canal-Front Pool Home was Built in 2015. Situated on the Highly Desir...
Listed by Ian Greenberg BRISTA REALTY LLC


$7,500
Condo
Longboat Key, FL 34228
NOW AVAILABLE FOR THE 2026 SEASON: Take a 60 second stroll across the street to the Gulf Beach from this Very Popular an...
Listed by Monique Holston-Greene, PA COLDWELL BANKER REALTY


$850,000
Condo
2181 HARBOURSIDE DR #1403, Longboat Key, FL 34228
PRICED TO SELL! Experience the ultimate in island living in the highly sought-after and prestigious Harbor Oaks communi...
Listed by Sharon Morea EXIT KING REALTY


$375,000
Condo
669 SPANISH DR N #21, Longboat Key, FL 34228
Fully renovated villa ready for immediate occupancy! Welcome to Spanish Main Yacht Club, a sought-after 55+ waterfront c...
Listed by Geoff Scalera AUM FLORIDA REAL ESTATE LLC


$7,000
Condo
2295 E GULF OF MEXICO DR E #55, Longboat Key, FL 34228
RARELY AVAILABLE! This absolutely gorgeous fully furnished 2BR/2BA Condo at Islander Club – Just steps from the Beach! <...
Listed by Michele Conn PREFERRED SHORE LLC
