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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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4545 GULF OF MEXICO DR #311, Longboat Key, FL 34228
Open Sun 1PM-3PM
36

$1,200,000

2 Beds 2 Baths 1,398 SqFt

4545 GULF OF MEXICO DR #311, Longboat Key, FL 34228

Listed by Janis Collier MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
617 WESTON POINTE CT, Longboat Key, FL 34228
Open 9/13 1PM-4PM
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 Sat 11AM-1PM
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 Sun 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
836 EVERGREEN WAY, Longboat Key, FL 34228
Open Sun 12PM-4PM
49

$875,000

3 Beds 3 Baths 2,813 SqFt

836 EVERGREEN WAY, Longboat Key, FL 34228

Listed by Eileen Saunders MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
1075 GULF OF MEXICO DR #303, Longboat Key, FL 34228
New
50

$925,000

2 Beds 2 Baths 1,503 SqFt

1075 GULF OF MEXICO DR #303, Longboat Key, FL 34228

Listed by Michael Moulton MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
714 NORTON ST, Longboat Key, FL 34228
New
39

$12,000

3 Beds 3 Baths 1,518 SqFt

714 NORTON ST, Longboat Key, FL 34228

Listed by Traci de Wid RESIDENTIAL WEALTH PARTNERS

Stellar MLS
Stellar MLS
2850 GULF OF MEXICO DR #2, Longboat Key, FL 34228
New
19

$2,700

2 Beds 1 Baths 695 SqFt

2850 GULF OF MEXICO DR #2, Longboat Key, FL 34228

Listed by Deserea Hardy ROSSI & COMPANY INC

Stellar MLS
Stellar MLS
3453 GULF OF MEXICO DR #200, Longboat Key, FL 34228
New
30

$390,000

1 Bed 1 Bath 876 SqFt

3453 GULF OF MEXICO DR #200, Longboat Key, FL 34228

Listed by Kelly Baldwin COLDWELL BANKER REALTY

Stellar MLS
Stellar MLS
1906 HARBOURSIDE DR #303, Longboat Key, FL 34228
New
55

$799,000

2 Beds 3 Baths 1,590 SqFt

1906 HARBOURSIDE DR #303, Longboat Key, FL 34228

Listed by Bruce Myer COLDWELL BANKER REALTY

Stellar MLS
Stellar MLS
3320 GULF OF MEXICO DR #206C, Longboat Key, FL 34228
New
48

$624,900

2 Beds 2 Baths 1,186 SqFt

3320 GULF OF MEXICO DR #206C, Longboat Key, FL 34228

Listed by Steve Walter MICHAEL SAUNDERS & COMPANY

Stellar MLS
Stellar MLS
707 SAINT JUDES DR S #1, Longboat Key, FL 34228
New
60

$399,000

1 Bed 1 Bath 630 SqFt

707 SAINT JUDES DR S #1, Longboat Key, FL 34228

Listed by Kristy Gentile RE/MAX ALLIANCE GROUP

Stellar MLS
Stellar MLS
592 JUAN ANASCO DR, Longboat Key, FL 34228
New
1

$4,000,000

5 Beds 6 Baths 3,600 SqFt

592 JUAN ANASCO DR, Longboat Key, FL 34228

Listed by Cory Jursik SHORE PROPERTY GROUP

Stellar MLS
Stellar MLS
4310 FALMOUTH DR #307, Longboat Key, FL 34228
New
47

$520,000

2 Beds 2 Baths 1,072 SqFt

4310 FALMOUTH DR #307, Longboat Key, FL 34228

Listed by Rachel Rademacher HOUSE MATCH

Stellar MLS
Stellar MLS
1055 GULF OF MEXICO DR #105, Longboat Key, FL 34228
New
78

$1,395,000

2 Beds 2 Baths 1,503 SqFt

1055 GULF OF MEXICO DR #105, Longboat Key, FL 34228

Listed by Sharon Austin PREMIER SOTHEBY'S INTERNATIONAL REALTY

Stellar MLS
Stellar MLS
1095 GULF OF MEXICO DR #104, Longboat Key, FL 34228
New
55

$599,000

2 Beds 2 Baths 1,503 SqFt

1095 GULF OF MEXICO DR #104, Longboat Key, FL 34228

Listed by Michael Renick PLLC MANGROVE REALTY ASSOCIATES

Stellar MLS
Stellar MLS
713 SAINT JUDES DR S #2, Longboat Key, FL 34228
New
45

$565,000

2 Beds 2 Baths 1,088 SqFt

713 SAINT JUDES DR S #2, Longboat Key, FL 34228

Listed by Rex Glasson DOUGLAS ELLIMAN

Stellar MLS
Stellar MLS
2089 GULF OF MEXICO DR #G1-302, Longboat Key, FL 34228
New
67

$3,500

2 Beds 2 Baths 1,257 SqFt

2089 GULF OF MEXICO DR #G1-302, Longboat Key, FL 34228

Listed by Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

Stellar MLS
Stellar MLS
2321 HARBOUR OAKS DR, Longboat Key, FL 34228
Active
37

$835,000

3 Beds 3 Baths 2,478 SqFt

2321 HARBOUR OAKS DR, Longboat Key, FL 34228

Listed by Susanna Condon WHITE SANDS REALTY GROUP FL

Stellar MLS
Stellar MLS
Longboat Key, FL 34228
Active
52

$14,500

3 Beds 3 Baths 1,498 SqFt

Longboat Key, FL 34228

Listed by David Holt PMI SOUTHWEST FLORIDA

Stellar MLS
Stellar MLS
36 TWIN SHORES BLVD, Longboat Key, FL 34228
Active
46

$149,900

1 Bed 1 Bath 564 SqFt

36 TWIN SHORES BLVD, Longboat Key, FL 34228

Listed by Sharon Austin PREMIER SOTHEBY'S INTERNATIONAL REALTY

Stellar MLS
Stellar MLS
6700 GULF OF MEXICO DR #117, Longboat Key, FL 34228
Active
51

$4,500

2 Beds 2 Baths 1,449 SqFt

6700 GULF OF MEXICO DR #117, Longboat Key, FL 34228

Listed by Kim Blakeney JENNETTE PROPERTIES INC

Stellar MLS
Stellar MLS
885 SPANISH DR N, Longboat Key, FL 34228
Active
50

$2,600

2 Beds 2 Baths 1,423 SqFt

885 SPANISH DR N, Longboat Key, FL 34228

Listed by Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

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: 09/01/2026 05:01

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