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Longboat Key

Longboat Key is an idyllic sanctuary combining tranquil beaches and luxury living. Its white sands and clear waters are perfect for those seeking peace or water activities, while upscale condominiums and private communities offer sumptuous amenities. Recreational opportunities are abundant with top-tier golf courses, tennis centers, and marinas for boating enthusiasts. The island's placement between Sarasota Bay and the Gulf of Mexico ensures stunning waterfront vistas and wildlife encounters, adding to the locale's natural charm.

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597 SUTTON PL, Longboat Key, FL 34228
Open Wed 1PM-3PM
50

$499,999

2 Beds 2 Baths 1,008 SqFt

597 SUTTON PL, Longboat Key, FL 34228

Listed by Simone Schaerf MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
3488 MISTLETOE LN, Longboat Key, FL 34228
Open Sun 1PM-4PM
81

$3,275,000

3 Beds 4 Baths 3,341 SqFt

3488 MISTLETOE LN, Longboat Key, FL 34228

Listed by Kim Ogilvie MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
765 SAINT JUDES DR N, Longboat Key, FL 34228
Open Wed 12PM-3PM
58

$1,350,000

4 Beds 2 Baths 1,900 SqFt

765 SAINT JUDES DR N, Longboat Key, FL 34228

Listed by Kalison Nix PREFERRED SHORE LLC

Stellar MLS
Stellar MLS
560 CHIPPING LN, Longboat Key, FL 34228
Open Sun 1PM-4PM
37

$3,999,990

5 Beds 5 Baths 4,315 SqFt

560 CHIPPING LN, Longboat Key, FL 34228

Listed by Monica Verinder COLDWELL BANKER REALTY

Stellar MLS
Stellar MLS
6930 LONGBOAT DR S, Longboat Key, FL 34228
New
48

$2,995,000

4 Beds 5 Baths 2,541 SqFt

6930 LONGBOAT DR S, Longboat Key, FL 34228

Listed by Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

Stellar MLS
Stellar MLS
1241 GULF OF MEXICO DR #506, Longboat Key, FL 34228
Coming Soon
59

$3,750,000

3 Beds 3 Baths 2,650 SqFt

1241 GULF OF MEXICO DR #506, Longboat Key, FL 34228

Listed by Tyler Sajan LPT REALTY, LLC

Stellar MLS
Stellar MLS
2045 GULF OF MEXICO DR #M1-501, Longboat Key, FL 34228
New
42

$5,000

2 Beds 2 Baths 1,265 SqFt

2045 GULF OF MEXICO DR #M1-501, Longboat Key, FL 34228

Listed by Emerson Robbins HARRY ROBBINS ASSOC INC

Stellar MLS
Stellar MLS
435 L AMBIANCE DR #L707, Longboat Key, FL 34228
New
56

$2,850,000

2 Beds 3 Baths 2,525 SqFt

435 L AMBIANCE DR #L707, Longboat Key, FL 34228

Listed by Pam Charron COMPASS FLORIDA LLC

Stellar MLS
Stellar MLS
1591 GULF OF MEXICO DR #514, Longboat Key, FL 34228
Pending
75

$7,195,000

2 Beds 3 Baths 2,249 SqFt

1591 GULF OF MEXICO DR #514, Longboat Key, FL 34228

Listed by Kim Ogilvie MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
2165 GULF OF MEXICO DR #121, Longboat Key, FL 34228
New
60

$2,445,000

3 Beds 3 Baths 2,470 SqFt

2165 GULF OF MEXICO DR #121, Longboat Key, FL 34228

Listed by Nicole Hammons-Dovgopolyi MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
3030 GRAND BAY BLVD #315, Longboat Key, FL 34228
New
62

$1,395,000

3 Beds 4 Baths 2,143 SqFt

3030 GRAND BAY BLVD #315, Longboat Key, FL 34228

Listed by Sherry Dominick MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
775 LONGBOAT CLUB RD, 1008-1007, Longboat Key, FL 34228
New
46

$5,500,000

4 Beds 4 Baths 3,954 SqFt

775 LONGBOAT CLUB RD, 1008-1007, Longboat Key, FL 34228

Listed by Lenore Treiman MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
575 SUTTON PL, Longboat Key, FL 34228
New
61

$589,000

3 Beds 3 Baths 1,450 SqFt

575 SUTTON PL, Longboat Key, FL 34228

Listed by Shayla Twit CORCORAN DWELLINGS REALTY

Stellar MLS
Stellar MLS
2352 HARBOUR OAKS DR, Longboat Key, FL 34228
New
59

$1,249,000

3 Beds 3 Baths 2,487 SqFt

2352 HARBOUR OAKS DR, Longboat Key, FL 34228

Listed by Sherry Dominick MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
1241 GULF OF MEXICO DR #803, Longboat Key, FL 34228
New
37

$3,195,000

3 Beds 4 Baths 3,045 SqFt

1241 GULF OF MEXICO DR #803, Longboat Key, FL 34228

Listed by Ryan Ackerman, PA COLDWELL BANKER REALTY

Stellar MLS
Stellar MLS
595 BOWSPRIT LN, Longboat Key, FL 34228
Coming Soon
49

$2,950,000

4 Beds 3 Baths 2,550 SqFt

595 BOWSPRIT LN, Longboat Key, FL 34228

Listed by Melissa Gissinger MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
2425 GULF OF MEXICO DR #14B, Longboat Key, FL 34228
Coming Soon
33

$1,600,000

2 Beds 2 Baths 1,470 SqFt

2425 GULF OF MEXICO DR #14B, Longboat Key, FL 34228

Listed by Andrey Markov ANMARK REALTY LLC

Stellar MLS
Stellar MLS
2425 GULF OF MEXICO DR #1E, Longboat Key, FL 34228
New
36

$1,450,000

2 Beds 2 Baths 1,472 SqFt

2425 GULF OF MEXICO DR #1E, Longboat Key, FL 34228

Listed by Robert Delaney MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
3070 GRAND BAY BLVD #645, Longboat Key, FL 34228
New
45

$925,000

2 Beds 2 Baths 1,276 SqFt

3070 GRAND BAY BLVD #645, Longboat Key, FL 34228

Listed by Beverly St Hilaire MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
6061 GULF OF MEXICO DR, Longboat Key, FL 34228
New
85

$7,900,000

5 Beds 6 Baths 3,203 SqFt

6061 GULF OF MEXICO DR, Longboat Key, FL 34228

Listed by Reid Murphy DEVELOPERS REALTY LBK, INC

Stellar MLS
Stellar MLS
1241 GULF OF MEXICO DR #PH1102, Longboat Key, FL 34228
New
58

$5,995,000

3 Beds 5 Baths 3,400 SqFt

1241 GULF OF MEXICO DR #PH1102, Longboat Key, FL 34228

Listed by Steve Walter MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
1591 GULF OF MEXICO DR #515, Longboat Key, FL 34228
New
53

$2,670,000

1 Bed 2 Bath 1,556 SqFt

1591 GULF OF MEXICO DR #515, Longboat Key, FL 34228

Listed by Lynn Morris, PLLC MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
1591 GULF OF MEXICO DR #512, Longboat Key, FL 34228
New
65

$1,999,999

2 Beds 3 Baths 2,154 SqFt

1591 GULF OF MEXICO DR #512, Longboat Key, FL 34228

Listed by Frank Golio Jr., PLLC LEGACY BAY PARTNERS

Stellar MLS
Stellar MLS
2245 HARBOURSIDE DR #101, Longboat Key, FL 34228
Active Under Contract
63

$1,150,000

3 Beds 3 Baths 2,219 SqFt

2245 HARBOURSIDE DR #101, Longboat Key, FL 34228

Listed by Scott Rickards, PA RE/MAX ALLIANCE GROUP

Stellar MLS
Stellar MLS

© 2026 My Florida Regional MLS DBA Stellar MLS. All Rights Reserved. The data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data Last Updated: 11/02/2026 10:01

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