Homes with Pools for Sale in Longboat Key, FL

373 homes

Sort:

Recommended

ABOUT THIS HOME
Home with a Pool for sale in Longboat Key, FL:
Own the ultimate beachfront retreat on the coveted south end of Longboat Key—where your residence comes with a complimentary membership at the brand-new St. Regis Resort next door. Beautifully updated and fully furnished, this rare ground-floor walkout at the direct Gulf-front Aquarius Club offers effortless access to the beach and all the luxuries of coastal living. The 2-bedroom, 2-bath residence showcases soaring 9-foot ceilings, an open kitchen, and expansive living areas with floor-to-ceiling hurricane-impact windows and sliders framing stunning Gulf and Bay views from every room. Situated just one unit from the sand on the north side of the building, this home is perfectly posit

$1,625,000

2 beds2 baths1,551 sq ft

1701 Gulf OF Mexico Dr #109, Longboat Key, FL 34228

Ground-floor walkout • Private balcony • Beachfront retreat

ABOUT THIS HOME
Home with a Pool for sale in Longboat Key, FL:
0.5 mi to Gulf beach access • Two heated pools & tennis courts • Gated Gulf-front community Welcome to Seaplace, a premier Gulf-front condominium community along Longboat Key’s scenic Gulf of Mexico Drive. This two-bedroom, two-bath residence (Unit G4-308) combines coastal living and community amenities in one of Sarasota County’s most desirable barrier-island locations. The open-concept layout flows seamlessly from the kitchen through the main living area to a screened lanai overlooking lush tropical landscaping and the Har-Tru tennis courts. Durable LVP flooring enhances the main living spaces, while neutral finishes allow a bright, airy feel throughout. The

$480,000

2 beds2 baths1,068 sq ft

1975 Gulf OF Mexico Dr Unit G4-308, Longboat Key, FL 34228

Open floor plan • Screened lanai • Walk in closet

ABOUT THIS HOME
Home with a Pool for sale in Longboat Key, FL:
Discover coastal living at its finest with this charming condominium located on Gulf of Mexico Dr, Longboat Key. This residence offers stunning ocean views and easy access to beautiful beaches. The open-concept layout features modern finishes, a spacious living area, and a well-appointed kitchen. Enjoy relaxing on the private balcony overlooking the serene surroundings. The community amenities include a swimming pool, fitness center, and convenient access to local dining and shopping.

$305,000

1 bed1 bath712 sq ft

3806 Gulf OF Mexico Dr Unit C208, Longboat Key, FL 34228

Fitness center • Private balcony • Community amenities

ABOUT THIS HOME
Home with a Pool for sale in Longboat Key, FL:
This stunning 2 bed/2 bath residence comes turnkey furnished offering a full view of the Longboat Key Islandside Golf Course and partial views of the Gulf, Sarasota Bay, and the Sarasota city skyline through Hurricane Impact Sliders installed in 2024. The kitchen has been opened up to the living/dining area providing a beautiful view over the golf course greens while owners are creating culinary delights in the kitchen. There is a breakfast bar, a laundry closet, pantry, and plenty of solid wood cabinet space for storage. The primary suite pampers owners with access to the southeast-facing terrace along with a spacious primary bath offering dual vanities, an updated tile shower, and abundan

$845,000

2 beds2 baths1,392 sq ft

1065 Gulf OF Mexico Dr #402, Longboat Key, FL 34228

Laundry closet • Breakfast bar • $1,633 HOA

ABOUT THIS HOME
Home with a Pool for sale in Longboat Key, FL:
Rare opportunity, two fully furnished TWIN residences (TWO UNITS BEING SOLD AS ONE 4473+4477 Gulf of Mexico Drive ). Directly on the pristine shores of Longboat Key! Combined 8 bedrooms, 8 Bathrooms. Spanning nearly 6,000 sq. ft. , on . 58 GULF-FRONT acres, this two-story property offers mirror-image residences, each thoughtfully decorated with both modern and timeless designs. A true investment gem—live in one, rent the other, enjoy a multi-generational retreat, or explore redevelopment potential on this premier beachfront site. Direct Gulf-front access — step onto the sand from your back door. Sweeping water views from nearly every room! State-of-the-art kitchens with high-en

$10,900,000

8 beds8 baths5,886 sq ft

4473 Gulf OF Mexico Dr #4473, Longboat Key, FL 34228

Gulf-front access • Impact-rated windows • Pavered decks

Property at 311 Firehouse Ct, Longboat Key, FL 34228, 3 beds, 3.5 baths

$2,850,000

3 beds3.5 baths2,352 sq ft

311 Firehouse Ct, Longboat Key, FL 34228

Property at 1591 Gulf OF Mexico Dr #314, Longboat Key, FL 34228, 2 beds, 2.5 baths

$6,650,000

2 beds2.5 baths2,249 sq ft

1591 Gulf OF Mexico Dr #314, Longboat Key, FL 34228

Property at 1591 Gulf OF Mexico Dr #410, Longboat Key, FL 34228, 2 beds, 2.5 baths

$7,100,000

2 beds2.5 baths3,130 sq ft

1591 Gulf OF Mexico Dr #410, Longboat Key, FL 34228

Property at 865 Longboat Club Rd, Longboat Key, FL 34228, 6 beds, 7 baths

$19,750,000

6 beds7 baths9,328 sq ft

865 Longboat Club Rd, Longboat Key, FL 34228

Property at 1591 Gulf OF Mexico Dr #216, Longboat Key, FL 34228, 1 bed, 2.5 baths

$2,800,000

1 bed2.5 baths1,556 sq ft

1591 Gulf OF Mexico Dr #216, Longboat Key, FL 34228

Property at 521 Wedge Ln, Longboat Key, FL 34228, 3 beds, 2 baths

$1,880,000

3 beds2 baths1,758 sq ft

521 Wedge Ln, Longboat Key, FL 34228

Property at 1445 Gulf OF Mexico Dr #304, Longboat Key, FL 34228, 3 beds, 3 baths

$1,475,000

3 beds3 baths1,859 sq ft

1445 Gulf OF Mexico Dr #304, Longboat Key, FL 34228

Property at 847 Evergreen Way, Longboat Key, FL 34228, 2 beds, 2.5 baths

$628,000

2 beds2.5 baths1,440 sq ft

847 Evergreen Way, Longboat Key, FL 34228

Property at 6601 Gulfside Rd, Longboat Key, FL 34228, 5 beds, 3 baths

$5,000,000

5 beds3 baths3,492 sq ft

6601 Gulfside Rd, Longboat Key, FL 34228

Property at 1581 Gulf OF Mexico Dr #507, Longboat Key, FL 34228, 1 bed, 1.5 baths

$3,500,000

1 bed1.5 baths1,721 sq ft

1581 Gulf OF Mexico Dr #507, Longboat Key, FL 34228

Property at 2600 Harbourside Dr Unit J-04, Longboat Key, FL 34228

$350,000

— beds— baths— sq ft

2600 Harbourside Dr Unit J-04, Longboat Key, FL 34228

Property at 7105 Gulf OF Mexico Dr #21, Longboat Key, FL 34228, 2 beds, 2 baths

$1,065,000

2 beds2 baths1,170 sq ft

7105 Gulf OF Mexico Dr #21, Longboat Key, FL 34228

Property at 660 Linley St, Longboat Key, FL 34228, 3 beds, 3 baths

$675,000

3 beds3 baths1,564 sq ft

660 Linley St, Longboat Key, FL 34228

Property at 370 Gulf OF Mexico Dr #432, Longboat Key, FL 34228, 4 beds, 4 baths

$1,750,000

4 beds4 baths2,900 sq ft

370 Gulf OF Mexico Dr #432, Longboat Key, FL 34228

Property at 2600 Harbourside Dr Unit Q-08, Longboat Key, FL 34228

$265,000

— beds— baths— sq ft

2600 Harbourside Dr Unit Q-08, Longboat Key, FL 34228

Property at 4500 Gulf OF Mexico Dr #202, Longboat Key, FL 34228, 2 beds, 2 baths

$775,000

2 beds2 baths1,312 sq ft

4500 Gulf OF Mexico Dr #202, Longboat Key, FL 34228

Property at 667 EL Centro, Longboat Key, FL 34228, 2 beds, 2 baths

$380,000

2 beds2 baths1,327 sq ft

667 EL Centro, Longboat Key, FL 34228

Property at 4485 Gulf OF Mexico Dr #402, Longboat Key, FL 34228, 2 beds, 2 baths

$875,000

2 beds2 baths1,022 sq ft

4485 Gulf OF Mexico Dr #402, Longboat Key, FL 34228

Property at 1055 Gulf OF Mexico Dr #504, Longboat Key, FL 34228, 2 beds, 2 baths

$1,299,000

2 beds2 baths1,503 sq ft

1055 Gulf OF Mexico Dr #504, Longboat Key, FL 34228

Property at 658 Spanish Dr S #108, Longboat Key, FL 34228, 2 beds, 2 baths

$295,000

2 beds2 baths1,093 sq ft

658 Spanish Dr S #108, Longboat Key, FL 34228

Property at 562 Ranger Ln, Longboat Key, FL 34228, 4 beds, 3 baths

$3,290,000

4 beds3 baths2,346 sq ft

562 Ranger Ln, Longboat Key, FL 34228

Property at 565 Sanctuary Dr Unit B106, Longboat Key, FL 34228, 3 beds, 3 baths

$1,999,000

3 beds3 baths2,375 sq ft

565 Sanctuary Dr Unit B106, Longboat Key, FL 34228

Property at 3617 Fair Oaks Pl, Longboat Key, FL 34228, 3 beds, 3.5 baths

$2,159,000

3 beds3.5 baths2,950 sq ft

3617 Fair Oaks Pl, Longboat Key, FL 34228

Property at 210 Sands Point Rd #2405, Longboat Key, FL 34228, 1 bed, 1 bath

$1,175,000

1 bed1 bath650 sq ft

210 Sands Point Rd #2405, Longboat Key, FL 34228

Property at 1975 Gulf OF Mexico Dr Unit G4-206, Longboat Key, FL 34228, 2 beds, 2 baths

$479,000

2 beds2 baths1,068 sq ft

1975 Gulf OF Mexico Dr Unit G4-206, Longboat Key, FL 34228

Property at 1904 Harbourside Dr #202, Longboat Key, FL 34228, 2 beds, 2.5 baths

$517,000

2 beds2.5 baths1,590 sq ft

1904 Harbourside Dr #202, Longboat Key, FL 34228

Property at 240 Sands Point Rd #4102, Longboat Key, FL 34228, 1 bed, 1 bath

$950,000

1 bed1 bath640 sq ft

240 Sands Point Rd #4102, Longboat Key, FL 34228

Property at 1926 Harbourside Dr #1302, Longboat Key, FL 34228, 2 beds, 2.5 baths

$899,000

2 beds2.5 baths2,606 sq ft

1926 Harbourside Dr #1302, Longboat Key, FL 34228

Property at 3810 Gulf OF Mexico Dr Unit F302, Longboat Key, FL 34228, 2 beds, 2 baths

$355,000

2 beds2 baths1,007 sq ft

3810 Gulf OF Mexico Dr Unit F302, Longboat Key, FL 34228

Property at 524 Halyard Ln, Longboat Key, FL 34228, 4 beds, 5 baths

$5,650,000

4 beds5 baths3,737 sq ft

524 Halyard Ln, Longboat Key, FL 34228

Property at 408 Gulf OF Mexico Dr #2112, Longboat Key, FL 34228

$43,500

— beds— baths— sq ft

408 Gulf OF Mexico Dr #2112, Longboat Key, FL 34228

Property at 2600 Harbourside Dr Unit I-09, Longboat Key, FL 34228

$300,000

— beds— baths— sq ft

2600 Harbourside Dr Unit I-09, Longboat Key, FL 34228

Property at 725 Penfield St, Longboat Key, FL 34228, 4 beds, 4 baths

$2,475,000

4 beds4 baths2,902 sq ft

725 Penfield St, Longboat Key, FL 34228

Property at 2600 Harbourside Dr Unit R9, Longboat Key, FL 34228

$335,000

— beds— baths1,575 sq ft

2600 Harbourside Dr Unit R9, Longboat Key, FL 34228

Property at 5310 Gulf OF Mexico Dr #18, Longboat Key, FL 34228, 1 bed, 1 bath

$425,000

1 bed1 bath711 sq ft

5310 Gulf OF Mexico Dr #18, Longboat Key, FL 34228

Property at 601 Triton Bnd, Longboat Key, FL 34228, 4 beds, 4 baths

$3,450,000

4 beds4 baths3,313 sq ft

601 Triton Bnd, Longboat Key, FL 34228

Viewing page 5 of 9

Based on information submitted to the MLS GRID as of Mon Dec 01 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Homes with Pools for Sale in Longboat Key

There are currently 373 homes with pools for sale in Longboat Key at a median listing price of $1.25M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Longboat Key stay on the market for 91 days. Popular neighborhoods include Longboat Key Club, The Terraces at Wild Oak Bay, Longboat Harbour, Spanish Main Yacht Club Condominiums, and Longboat Shores. This map is refreshed with the newest listings in Longboat Key every 15 minutes.

In the past month, 39 homes have been sold in Longboat Key. In addition to houses in Longboat Key, there were also 233 condos, 5 townhouses, and 1 multi-family unit for sale in Longboat Key last month. Find your dream home in Longboat Key using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Longboat Key are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Longboat Key. Our Longboat Key real estate stats and trends will give you more information about home buying and selling trends in Longboat Key. If you're looking to sell your home in the Longboat Key area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Longboat Key with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Longboat Key, FL

Zip Codes

Neighborhoods

Nearby Cities

Nearby Cities with Homes with Pools

Nearby Neighborhoods with Homes with Pools

More to explore in Longboat Key, FL

How to buy a house in Longboat Key, FL

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Florida

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.