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58 Properties Available
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$1,899,000
Single Family Home
524 KETCH LN, Longboat Key, FL 34228
Discover the quintessential Longboat Key lifestyle in this classic masonry beach home located just “3” properties in fro...
Listed by Kathy Callahan MICHAEL SAUNDERS & COMPANY


$5,650,000
Single Family Home
524 HALYARD LN, Longboat Key, FL 34228
One or more photo(s) has been virtually staged. Experience the ultimate in island living in this brand-new custom built ...
Listed by Rob Hunt, Jr HUNT BROTHERS REALTY, INC.


$1,250,000
Condo
1445 GULF OF MEXICO DR #404, Longboat Key, FL 34228
Gulf-Front Elegance at The Players Club. Welcome to the epitome of coastal luxury living at The Players Club, where the ...
Listed by Kathy Callahan MICHAEL SAUNDERS & COMPANY


$499,000
Single Family Home
4840 GULF OF MEXICO DR #Villa 15, Longboat Key, FL 34228
LOCATION! LOCATION! LOCATION! Looking for a Beach/Bay Getaway Villa? This cozy End Unit Beach/Bay 2-bedroom/2-bath Sunny...
Listed by Debby McCaig COLDWELL BANKER REALTY


$4,199,000
Single Family Home
597 BUTTONWOOD DR, Longboat Key, FL 34228
GULF AND BAY VIEWS! THREE OUTDOOR PATIOS! Discover an extraordinary coastal contemporary masterpiece by Floridian Crafte...
Listed by Joshua Freed PREFERRED SHORE LLC


$649,000
Condo
4234 GULF OF MEXICO DR #E2, Longboat Key, FL 34228
Exceptional full Bay views and incredible value! This fully furnished 2BR/2BA retreat at Pelican Harbour & Beach Club de...
Listed by Lenore Treiman MICHAEL SAUNDERS & COMPANY


$1,945,000
Condo
2525 GULF OF MEXICO DR #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,...
Listed by JoDene Moneuse, PA MICHAEL SAUNDERS & COMPANY


$1,095,000
Condo
5055 GULF OF MEXICO DR #331, Longboat Key, FL 34228
Welcome to your coastal retreat in paradise — a stunning third-floor waterfront residence in Club Longboat Beach and Ten...
Listed by Ryan Heers COLDWELL BANKER REALTY


$6,500
Single Family Home
4780 GULF OF MEXICO DR. VILLA 5, Longboat Key, FL 34228
Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now ava...
Listed by Debby McCaig COLDWELL BANKER REALTY


$769,000
Condo
2155 HARBOURSIDE DR #804, Longboat Key, FL 34228
Located in the quiet, gated community of Bay Isles on Longboat Key, this beautifully renovated – 2nd-floor residence in ...
Listed by Bruce Myer COLDWELL BANKER REALTY


$483,999
Condo
4380 EXETER DR #303, Longboat Key, FL 34228
PENTHOUSE UNIT!! DEEDED BEACH ACCESS DIRECTLY ACROSS THE STREET!! New roof 2025! Top-floor, end-unit living with sparkli...
Listed by Andrew Reese COLDWELL BANKER SUNSTAR REALTY


$649,999
Condo
3320 GULF OF MEXICO DR #207-C, Longboat Key, FL 34228
Modern Waterfront Living in the Heart of Longboat Key-Experience the best of coastal living in this beautifully renovate...
Listed by Tami Cashi COLDWELL BANKER REALTY


$7,100,000
Condo
1591 GULF OF MEXICO DR #410, Longboat Key, FL 34228
A rare opportunity to own the largest two-bedroom floor plan at the exclusive St. Regis Longboat Key. This premier corne...
Listed by Lynn Morris, PLLC MICHAEL SAUNDERS & COMPANY


$19,750,000
Single Family Home
865 LONGBOAT CLUB RD, Longboat Key, FL 34228
Regent's Court: The Pinnacle of Luxury on Florida's West Coast <br>Regents Court: Where Legend Meets Luxury <br> <br>Bey...
Listed by Reid Murphy DEVELOPERS REALTY LBK, INC


$628,000
Townhouse
847 EVERGREEN WAY, Longboat Key, FL 34228
Income-Producing Coastal Gem – This TURNKEY FURNISHED 2BR/2.5BA townhome in the exclusive Cedars East Tennis Resort isn'...
Listed by Kiki Bowers COLDWELL BANKER REALTY


$949,500
Condo
2012 HARBOURSIDE DR #2104, Longboat Key, FL 34228
Discover Refined Coastal Living at Fairway Bay <br>Impeccably renovated from top to bottom, this three-bedroom, three-b...
Listed by Steve Walter MICHAEL SAUNDERS & COMPANY


$3,290,000
Single Family Home
562 RANGER LN, Longboat Key, FL 34228
A rare opportunity to secure a single-family home with 100' of canal frontage that has direct access to beautiful Saraso...
Listed by Camilo Perez HOME SOLD REALTY LLC


$12,000
Condo
2425 GULF OF MEXICO DR #11F, Longboat Key, FL 34228
ELEGANT BEACH FRONT CONDO ON LONGBOAT KEY. This exquisite 2 bedroom, 2 bathroom condo has been totally updated. The kitc...
Listed by Teresa Ribaudo JENNETTE PROPERTIES INC


$899,000
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


$874,900
Condo
1050 LONGBOAT CLUB RD #204, Longboat Key, FL 34228
**Pirce Improvement ~ Motivated Seller** Step into the island lifestyle you've always imagined at Privateer North, locat...
Listed by Chris Carpenter COLDWELL BANKER SARASOTA CENT.


$4,424,000
Single Family Home
5005 GULF OF MEXICO DR #5, Longboat Key, FL 34228
The Quintessence of Coastal Living: A British West Indies Masterpiece on Longboat Key - Where Architecture Meets Paradis...
Listed by Kathy Callahan MICHAEL SAUNDERS & COMPANY


$11,000
Condo
1000 LONGBOAT CLUB RD, Longboat Key, FL 34228
Welcome to your elevated coastal retreat on Longboat Key, located behind the gate of the prestigious Longboat Key Club. ...
Listed by Jenna Genovese KELLER WILLIAMS ON THE WATER S


$8,000
Single Family Home
2377 HARBOUR OAKS DR, Longboat Key, FL 34228
AVAILABLE - APRIL 2026 - ANNUAL RENTAL - Welcome home! Enjoy the serenity of this 3 bed, 3 bath, 2 car garage residence...
Listed by Antonietta Car KELLER WILLIAMS SUBURBAN TAMPA


$585,000
Condo
1945 GULF OF MEXICO DR #M2-207, Longboat Key, FL 34228
Partial Gulf View Condo in Highly Sought-After Seaplace Community. <br> <br>Selling as Fully furnished. Don't miss this ...
Listed by Harold Kaufman PREFERRED SHORE LLC

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