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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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729 SAINT JUDES DR S #3, Longboat Key, FL 34228
Open Sun 1PM-4PM
68

$449,000

1 Bed 1 Bath 630 SqFt

729 SAINT JUDES DR S #3, Longboat Key, FL 34228

Listed by Steven Schield MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
4234 GULF OF MEXICO DR #J1, Longboat Key, FL 34228
Open Sun 12PM-2PM
48

$599,000

2 Beds 2 Baths 1,150 SqFt

4234 GULF OF MEXICO DR #J1, Longboat Key, FL 34228

Listed by Michael Seamon PREMIER SOTHEBY'S INTERNATIONAL REALTY

Stellar MLS
Stellar MLS
3511 FAIR OAKS CT, Longboat Key, FL 34228
Open Sun 1PM-4PM
58

$1,559,000

3 Beds 3 Baths 2,579 SqFt

3511 FAIR OAKS CT, Longboat Key, FL 34228

Listed by Kathy Callahan MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
1912 HARBOURSIDE DR #604, Longboat Key, FL 34228
Open Sun 1PM-4PM
88

$850,000

3 Beds 3 Baths 1,316 SqFt

1912 HARBOURSIDE DR #604, Longboat Key, FL 34228

Listed by Darlena Nelms S&N REAL ESTATE, INC.

Stellar MLS
Stellar MLS
691 GULF BAY RD, Longboat Key, FL 34228
Open Sun 11AM-2PM
34

$950,000

3 Beds 2 Baths 1,581 SqFt

691 GULF BAY RD, Longboat Key, FL 34228

Listed by Angela Scott MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
4835 GULF OF MEXICO DR #105, Longboat Key, FL 34228
Open Sun 12PM-2PM
33

$725,000

2 Beds 2 Baths 1,393 SqFt

4835 GULF OF MEXICO DR #105, Longboat Key, FL 34228

Listed by Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

Stellar MLS
Stellar MLS
2326 HARBOUR OAKS DR, Longboat Key, FL 34228
Open 3/28 1PM-3PM
98

$985,000

3 Beds 3 Baths 2,282 SqFt

2326 HARBOUR OAKS DR, Longboat Key, FL 34228

Listed by Rachel Tritschler RE/MAX ALLIANCE GROUP

Stellar MLS
Stellar MLS
1445 GULF OF MEXICO DR #103, Longboat Key, FL 34228
Open Sun 1PM-4PM
65

$989,900

3 Beds 3 Baths 1,933 SqFt

1445 GULF OF MEXICO DR #103, Longboat Key, FL 34228

Listed by Steve Nursey MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
4720 GULF OF MEXICO DR #Villa 2, Longboat Key, FL 34228
Open Sun 1PM-3PM
59

$599,000

2 Beds 2 Baths 912 SqFt

4720 GULF OF MEXICO DR #Villa 2, Longboat Key, FL 34228

Listed by Sharon Austin PREMIER SOTHEBY'S INTERNATIONAL REALTY

Stellar MLS
Stellar MLS
563 SPANISH DR S, Longboat Key, FL 34228
Open Sun 11AM-1PM
44

$615,000

2 Beds 2 Baths 1,516 SqFt

563 SPANISH DR S, Longboat Key, FL 34228

Listed by Victoria Campbell LPT REALTY LLC

Stellar MLS
Stellar MLS
677 LANDS END DR, Longboat Key, FL 34228
Open Sat 12PM-2:30PM
76

$2,850,000

3 Beds 3 Baths 4,000 SqFt

677 LANDS END DR, Longboat Key, FL 34228

Listed by Cindy Fischer PREMIER SOTHEBY'S INTERNATIONAL REALTY

Stellar MLS
Stellar MLS
1918 HARBOURSIDE DR #902, Longboat Key, FL 34228
Open Sun 1PM-4PM
55

$1,299,000

2 Beds 3 Baths 1,748 SqFt

1918 HARBOURSIDE DR #902, Longboat Key, FL 34228

Listed by Liz Nason PREMIER SOTHEBY'S INTERNATIONAL REALTY

Stellar MLS
Stellar MLS
4320 FALMOUTH DR #103, Longboat Key, FL 34228
Open Sun 1PM-3:30PM
69

$525,000

2 Beds 2 Baths 1,072 SqFt

4320 FALMOUTH DR #103, Longboat Key, FL 34228

Listed by Malihe Karimi MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
552 JUAN ANASCO DRIVE, Longboat Key, FL 34228
Open Sat 1PM-3PM
46

$999,999

3 Beds 4 Baths 1,846 SqFt

552 JUAN ANASCO DRIVE, Longboat Key, FL 34228

Listed by Kathy Cahill KELLER WILLIAMS ON THE WATER

Stellar MLS
Stellar MLS
548 GUNWALE LN, Longboat Key, FL 34228
Open Sat 1PM-4PM
62

$2,200,000

3 Beds 2 Baths 1,853 SqFt

548 GUNWALE LN, Longboat Key, FL 34228

Listed by John August MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
4750 GULF OF MEXICO DR #Villa 8, Longboat Key, FL 34228
Open Sun 3PM-5PM
76

$850,000

3 Beds 2 Baths 1,504 SqFt

4750 GULF OF MEXICO DR #Villa 8, Longboat Key, FL 34228

Listed by Debby McCaig COLDWELL BANKER REALTY

Stellar MLS
Stellar MLS
4311 GULF OF MEXICO DR #501, Longboat Key, FL 34228
Open Sun 1PM-4PM
34

$1,095,000

2 Beds 2 Baths 1,239 SqFt

4311 GULF OF MEXICO DR #501, Longboat Key, FL 34228

Listed by Richard Perlman MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
4310 FALMOUTH DR #102, Longboat Key, FL 34228
Open Sat 1PM-3PM
94

$675,000

2 Beds 2 Baths 1,072 SqFt

4310 FALMOUTH DR #102, Longboat Key, FL 34228

Listed by Kerre Allman MARCUS & COMPANY REALTY

Stellar MLS
Stellar MLS
1571 HARBOR CAY LN, Longboat Key, FL 34228
Open Sun 1PM-4PM
93

$4,750,000

4 Beds 4 Baths 4,209 SqFt

1571 HARBOR CAY LN, Longboat Key, FL 34228

Listed by Julie Klick MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
4310 FALMOUTH DR #304, Longboat Key, FL 34228
Open Sun 11AM-2PM
44

$399,000

1 Bed 1 Bath 747 SqFt

4310 FALMOUTH DR #304, Longboat Key, FL 34228

Listed by Rachel Rademacher HOUSE MATCH

Stellar MLS
Stellar MLS
4805 GULF OF MEXICO DR #103, Longboat Key, FL 34228
Open Sun 1PM-3:30PM
58

$774,900

2 Beds 2 Baths 1,393 SqFt

4805 GULF OF MEXICO DR #103, Longboat Key, FL 34228

Listed by Malihe Karimi MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
3598 FAIR OAKS LN, Longboat Key, FL 34228
Open Sun 1PM-4PM
43

$2,795,000

4 Beds 4 Baths 3,417 SqFt

3598 FAIR OAKS LN, Longboat Key, FL 34228

Listed by Roger Pettingell COLDWELL BANKER REALTY

Stellar MLS
Stellar MLS
2109 GULF OF MEXICO DR #1303, Longboat Key, FL 34228
Open Sun 1PM-4PM
44

$1,125,000

2 Beds 2 Baths 1,463 SqFt

2109 GULF OF MEXICO DR #1303, Longboat Key, FL 34228

Listed by Wendy Leventhal COLDWELL BANKER REALTY

Stellar MLS
Stellar MLS
5260 GULF OF MEXICO DR #403, Longboat Key, FL 34228
Open Sat 11AM-1PM
42

$649,999

2 Beds 2 Baths 1,128 SqFt

5260 GULF OF MEXICO DR #403, Longboat Key, FL 34228

Listed by Kaitlin Kuhn MICHAEL SAUNDERS & COMPANY

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: 03/21/2026 11:01

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