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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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1095 GULF OF MEXICO DR #303, Longboat Key, FL 34228
Open Sat 12PM-2PM
44

$775,000

2 Beds 2 Baths 1,503 SqFt

1095 GULF OF MEXICO DR #303, Longboat Key, FL 34228

Listed by Abigail Lange HOUSE MATCH

Stellar MLS
Stellar MLS
617 WESTON POINTE CT, Longboat Key, FL 34228
Pending
70

$3,100,000

4 Beds 5 Baths 4,395 SqFt

617 WESTON POINTE CT, Longboat Key, FL 34228

Listed by Jason Kranz, PA LPT REALTY, LLC

Stellar MLS
Stellar MLS
3527 FAIR OAKS LN, Longboat Key, FL 34228
Open Sun 1PM-4PM
91

$2,550,000

4 Beds 5 Baths 4,154 SqFt

3527 FAIR OAKS LN, Longboat Key, FL 34228

Listed by Miriam Pearson COLDWELL BANKER REALTY

Stellar MLS
Stellar MLS
4720 GULF OF MEXICO DR #Villa 2, Longboat Key, FL 34228
Open Wed 5PM-7PM
59

$585,000

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
548 GUNWALE LN, Longboat Key, FL 34228
Open Fri 1PM-4PM
56

$1,950,000

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
1591 GULF OF MEXICO DR #312, Longboat Key, FL 34228
New
40

$4,290,000

2 Beds 3 Baths 2,154 SqFt

1591 GULF OF MEXICO DR #312, Longboat Key, FL 34228

Listed by Lynn Morris, PLLC MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
4600 GULF OF MEXICO DR #301, Longboat Key, FL 34228
New
28

$670,000

2 Beds 2 Baths 1,561 SqFt

4600 GULF OF MEXICO DR #301, Longboat Key, FL 34228

Listed by Janice Buehl FUTURE HOME REALTY INC

Stellar MLS
Stellar MLS
843 BAYPORT WAY #843, Longboat Key, FL 34228
New
87

$645,000

2 Beds 2 Baths 1,260 SqFt

843 BAYPORT WAY #843, Longboat Key, FL 34228

Listed by Jennifer Thompson, PA COLDWELL BANKER REALTY

Stellar MLS
Stellar MLS
732 BAYPORT WAY, Longboat Key, FL 34228
New
42

$1,050,000

2 Beds 2 Baths 1,456 SqFt

732 BAYPORT WAY, Longboat Key, FL 34228

Listed by Jennifer Kenna EXP REALTY, LLC

Stellar MLS
Stellar MLS
691 TARAWITT DR, Longboat Key, FL 34228
New
35

$815,000

2 Beds 2 Baths 1,490 SqFt

691 TARAWITT DR, Longboat Key, FL 34228

Listed by JoDene Moneuse, PA MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
521 FOREST WAY, Longboat Key, FL 34228
New
48

$599,900

2 Beds 3 Baths 1,440 SqFt

521 FOREST WAY, Longboat Key, FL 34228

Listed by Jesse Griffin CENTURY 21 BEGGINS ENTERPRISES

Stellar MLS
Stellar MLS
3453 GULF OF MEXICO DR #237, Longboat Key, FL 34228
New
25

$495,000

1 Baths 368 SqFt

3453 GULF OF MEXICO DR #237, Longboat Key, FL 34228

Listed by Rogers Moore COLDWELL BANKER REALTY

Stellar MLS
Stellar MLS
2101 HARBOURSIDE DR #1103, Longboat Key, FL 34228
New
65

$1,495,000

3 Beds 3 Baths 2,204 SqFt

2101 HARBOURSIDE DR #1103, Longboat Key, FL 34228

Listed by Steve Walter MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
5461 GULF OF MEXICO DR #304, Longboat Key, FL 34228
Coming Soon
50

$1,495,000

2 Beds 2 Baths 1,516 SqFt

5461 GULF OF MEXICO DR #304, Longboat Key, FL 34228

Listed by Maggie Hicks COLDWELL BANKER REALTY

Stellar MLS
Stellar MLS
2020 HARBOURSIDE DR #442, Longboat Key, FL 34228
New
56

$699,000

2 Beds 2 Baths 1,192 SqFt

2020 HARBOURSIDE DR #442, Longboat Key, FL 34228

Listed by Steve Walter MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
1932 HARBOURSIDE DR #214, Longboat Key, FL 34228
Active Under Contract
38

$449,000

2 Beds 2 Baths 1,192 SqFt

1932 HARBOURSIDE DR #214, Longboat Key, FL 34228

Listed by Sherri Mills MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
3802 GULF OF MEXICO DR #A203, Longboat Key, FL 34228
New
72

$399,000

2 Beds 2 Baths 1,007 SqFt

3802 GULF OF MEXICO DR #A203, Longboat Key, FL 34228

Listed by Holly Switow PREMIER SOTHEBY'S INTERNATIONAL REALTY

Stellar MLS
Stellar MLS
1211 GULF OF MEXICO DR #603, Longboat Key, FL 34228
New
44

$1,595,000

2 Beds 2 Baths 1,585 SqFt

1211 GULF OF MEXICO DR #603, Longboat Key, FL 34228

Listed by Roger Pettingell COLDWELL BANKER REALTY

Stellar MLS
Stellar MLS
3453 GULF OF MEXICO DR #242, Longboat Key, FL 34228
New
37

$489,900

1 Bed 1 Bath 528 SqFt

3453 GULF OF MEXICO DR #242, Longboat Key, FL 34228

Listed by Eileen Saunders MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
96 TWIN SHORES BLVD, Longboat Key, FL 34228
New
9

$399,000

2 Beds 2 Baths 758 SqFt

96 TWIN SHORES BLVD, Longboat Key, FL 34228

Listed by Kyle Adams EVENTIDE REALTY LLC

Stellar MLS
Stellar MLS
510 GOLF LINKS LN, Longboat Key, FL 34228
New
87

$34,000

5 Beds 7 Baths 4,290 SqFt

510 GOLF LINKS LN, Longboat Key, FL 34228

Listed by C. Alison Hunter JENNETTE PROPERTIES INC

Stellar MLS
Stellar MLS
4540 GULF OF MEXICO DR #PH2, Longboat Key, FL 34228
New
78

$9,000

2 Beds 2 Baths 1,325 SqFt

4540 GULF OF MEXICO DR #PH2, Longboat Key, FL 34228

Listed by Debby McCaig COLDWELL BANKER REALTY

Stellar MLS
Stellar MLS
3808 GULF OF MEXICO DR #E111, Longboat Key, FL 34228
New
35

$4,500

2 Beds 2 Baths 1,085 SqFt

3808 GULF OF MEXICO DR #E111, Longboat Key, FL 34228

Listed by Kathleen Magnus FLORIDA GALLERY REAL ESTATE

Stellar MLS
Stellar MLS
1561 GULF OF MEXICO DR #404, Longboat Key, FL 34228
New
69

$12,750,000

3 Beds 4 Baths 4,967 SqFt

1561 GULF OF MEXICO DR #404, Longboat Key, FL 34228

Listed by Lynn Morris, PLLC 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: 09/21/2026 21:01

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