Homes with Pools for Sale in Windermere, FL

176 homes

Sort:

Recommended

NEW 12 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Windermere, FL:
Welcome to Villa Cartmel, where privacy lives beautifully. Set behind the gates of Lake Butler Sound, this exceptional Windermere residence offers a rare combination of privacy, tranquility, and effortless Florida living. With 5 bedrooms, 4.5 bathrooms, and a 3-car garage, the home has been thoughtfully designed for everyday comfort, elegant entertaining, and the relaxed lifestyle that makes Central Florida so desirable. From the moment you enter, beautifully appointed living spaces flow naturally from one to the next, creating an atmosphere that feels luxury yet welcoming. Expansive windows bring abundant natural light into the interiors while framing the lush greenery beyond and creating

$2,390,000

5 beds4.5 baths3,975 sq ft

6544 Cartmel Ln, Windermere, FL 34786

Lush landscaping • 0.56 acre lot • 3 garage spots

ABOUT THIS HOME
Home with a Pool for sale in Windermere, FL:
MOVE-IN READY WINDERMERE HOME WITH CONSERVATION POND AREA! Located in desirable Westside Village, this 4-bedroom, 3.5-bath home offers an open floor plan, tiled roof, landscaped yard, spacious front porch, and a peaceful conservation-view backyard. The bright kitchen overlooks the living room and breakfast nook and features granite countertops, stainless steel appliances, and a large center island with seating and storage. French doors open to the patio, creating an easy connection between indoor and outdoor living. Enjoy resort-style amenities including a community pool, clubhouse, playground, paved walking trails, and beautiful water features. Ideally located near top-rated schools, shopp

$799,000

4 beds3.5 baths2,791 sq ft

12785 Westside Village Loop, Windermere, FL 34786

Open floor plan • Tiled roof • Landscaped yard

3D & VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Windermere, FL:
Welcome to 9602 Maywood Drive, a privately gated lakefront estate on Windermere's prestigious Butler Chain of Lakes. The home was reimagined through a renovation of more than $1 million by the award-winning firm KBF Design Gallery, and every detail was carefully considered. From dawn to dusk, the estate looks out over unobstructed sunrises and sunsets on Lake Down, the Butler Chain’s Northernmost lake known for crystal-clear water and premier largemouth bass fishing. As evening falls, it offers front-row views of the Walt Disney World and Universal Studios Orlando fireworks. Oversized custom steel-and-glass doors open to a grand foyer with soaring 26-foot ceilings. Overhead hangs a st

$4,350,000

5 beds5 baths5,305 sq ft

9602 Maywood Dr, Windermere, FL 34786

Gated access • Designer chandelier • 26-foot ceilings

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Windermere, FL:
Virtually Staged. WHIMSICAL POOL HOME | Welcome to the highly desired community of the Lakes Of Windermere. Enjoy the beauty of park-side living and the comfort of your own private pool retreat in this immaculate, move-in-ready home in the desirable Lakes of Windermere community. Featuring four bedrooms, three bathrooms, and 2,455 square feet of thoughtfully arranged living space, this inviting single-story residence features an expansive open floor plan. A roof replaced in 2023, air-conditioning system replaced in 2021, new water heater, and newly replaced pool cage screens add meaningful value to a home that is beautifully prepared for its next chapter. A welcoming covered front porch ove

$649,000

4 beds2.5 baths2,455 sq ft

7030 Mapperton Dr, Windermere, FL 34786

Covered front porch • Expansive kitchen • Community pool

ABOUT THIS HOME
Home with a Pool for sale in Windermere, FL:
Gracious Golf-Course Living in Keene’s Pointe . Welcome to an exceptional retreat in the prestigious, 24-hour guard-gated community where refined interiors, resort-style outdoor living and the coveted Windermere lifestyle come together beautifully. Perfectly positioned on 0.35 acres overlooking the 8th fairway of The Golden Bear Club’s Jack Nicklaus Signature golf course, this extensively updated 4-bedroom, 4-bath residence offers 3,912 square feet of living space designed for both elegant entertaining and comfortable everyday living. From the moment you enter, thoughtful upgrades and sophisticated finishes set the tone. Rich wood floors, designer lighting, custom window treatme

$1,999,000

4 beds4 baths3,912 sq ft

8229 Tibet Butler Dr, Windermere, FL 34786

Flexible floor plan • Gourmet kitchen • Home office

Property at 6858 Merrick Landing Blvd, Windermere, FL 34786, 3 beds, 2 baths

$615,000

3 beds2 baths2,115 sq ft

6858 Merrick Landing Blvd, Windermere, FL 34786

Property at 6533 Cartmel Ln, Windermere, FL 34786, 4 beds, 3.5 baths

$1,598,000

4 beds3.5 baths3,751 sq ft

6533 Cartmel Ln, Windermere, FL 34786

Property at 2009 Westover Reserve Blvd, Windermere, FL 34786, 4 beds, 3.5 baths

$1,100,000

4 beds3.5 baths3,607 sq ft

2009 Westover Reserve Blvd, Windermere, FL 34786

Property at 11963 Vermillion Ave, Windermere, FL 34786, 3 beds, 2.5 baths

$430,000

3 beds2.5 baths1,676 sq ft

11963 Vermillion Ave, Windermere, FL 34786

Property at 8179 Maritime Flag St #206, Windermere, FL 34786, 3 beds, 2 baths

$350,000

3 beds2 baths1,332 sq ft

8179 Maritime Flag St #206, Windermere, FL 34786

Property at 8168 Boat Hook Loop #302, Windermere, FL 34786, 2 beds, 2 baths

$299,997

2 beds2 baths1,161 sq ft

8168 Boat Hook Loop #302, Windermere, FL 34786

Property at 11727 Delwick Dr, Windermere, FL 34786, 4 beds, 3 baths

$875,000

4 beds3 baths2,704 sq ft

11727 Delwick Dr, Windermere, FL 34786

Property at 12721 Jacob Grace Ct, Windermere, FL 34786, 4 beds, 4 baths

$1,488,000

4 beds4 baths3,763 sq ft

12721 Jacob Grace Ct, Windermere, FL 34786

Property at 101 Lee St, Windermere, FL 34786, 5 beds, 4 baths

$1,395,000

5 beds4 baths4,186 sq ft

101 Lee St, Windermere, FL 34786

Property at 13738 Eden Isle Blvd, Windermere, FL 34786, 4 beds, 2 baths

$530,000

4 beds2 baths2,020 sq ft

13738 Eden Isle Blvd, Windermere, FL 34786

Property at 11021 Hawkshead Ct, Windermere, FL 34786, 5 beds, 4 baths

$1,100,000

5 beds4 baths3,557 sq ft

11021 Hawkshead Ct, Windermere, FL 34786

Property at 6113 Grosvenor Shore Dr, Windermere, FL 34786, 7 beds, 7 baths

$6,950,000

7 beds7 baths8,722 sq ft

6113 Grosvenor Shore Dr, Windermere, FL 34786

Property at 104 E 1st Ave, Windermere, FL 34786, 4 beds, 2.5 baths

$1,280,000

4 beds2.5 baths2,441 sq ft

104 E 1st Ave, Windermere, FL 34786

Property at 12809 Holdenbury Ln, Windermere, FL 34786, 4 beds, 2.5 baths

$625,000

4 beds2.5 baths2,683 sq ft

12809 Holdenbury Ln, Windermere, FL 34786

Property at 11532 Waterstone Loop Dr, Windermere, FL 34786, 4 beds, 5 baths

$2,350,000

4 beds5 baths4,169 sq ft

11532 Waterstone Loop Dr, Windermere, FL 34786

Property at 9343 Tibet Pointe Cir, Windermere, FL 34786, 7 beds, 9 baths

$7,450,000

7 beds9 baths8,362 sq ft

9343 Tibet Pointe Cir, Windermere, FL 34786

Property at 4906 Aviva Garden Ct, Windermere, FL 34786, 4 beds, 4.5 baths

$3,850,000

4 beds4.5 baths6,605 sq ft

4906 Aviva Garden Ct, Windermere, FL 34786

Property at 13535 Bramham Ln, Windermere, FL 34786, 3 beds, 2 baths

$489,900

3 beds2 baths1,820 sq ft

13535 Bramham Ln, Windermere, FL 34786

Property at 13324 Jervey St, Windermere, FL 34786, 4 beds, 3.5 baths

$649,000

4 beds3.5 baths2,750 sq ft

13324 Jervey St, Windermere, FL 34786

Property at 6120 Greatwater Dr, Windermere, FL 34786, 5 beds, 5 baths

$3,999,000

5 beds5 baths5,580 sq ft

6120 Greatwater Dr, Windermere, FL 34786

Property at 13424 Hopkinton Ct, Windermere, FL 34786, 4 beds, 2 baths

$500,000

4 beds2 baths2,190 sq ft

13424 Hopkinton Ct, Windermere, FL 34786

Property at 5192 Vardon Dr, Windermere, FL 34786, 6 beds, 9 baths

$19,500,000

6 beds9 baths13,494 sq ft

5192 Vardon Dr, Windermere, FL 34786

Property at 5186 Vardon Dr, Windermere, FL 34786, 6 beds, 6 baths

$4,395,000

6 beds6 baths4,739 sq ft

5186 Vardon Dr, Windermere, FL 34786

Property at 5092 Isleworth Country Club Dr, Windermere, FL 34786, 4 beds, 5 baths

$8,500,000

4 beds5 baths7,100 sq ft

5092 Isleworth Country Club Dr, Windermere, FL 34786

Property at 12934 Vennetta Way, Windermere, FL 34786, 3 beds, 2.5 baths

$369,000

3 beds2.5 baths1,680 sq ft

12934 Vennetta Way, Windermere, FL 34786

Property at 9010 Reflection Pointe Dr, Windermere, FL 34786, 4 beds, 3.5 baths

$945,000

4 beds3.5 baths3,264 sq ft

9010 Reflection Pointe Dr, Windermere, FL 34786

Property at 12909 Cragside Ln, Windermere, FL 34786, 4 beds, 2.5 baths

$639,500

4 beds2.5 baths2,460 sq ft

12909 Cragside Ln, Windermere, FL 34786

Property at 9310 Isleworth Gardens Dr, Windermere, FL 34786, 3 beds, 4 baths

$3,595,000

3 beds4 baths4,333 sq ft

9310 Isleworth Gardens Dr, Windermere, FL 34786

Property at 2540 Hempel Cove Ct, Windermere, FL 34786, 5 beds, 3 baths

$1,349,900

5 beds3 baths3,356 sq ft

2540 Hempel Cove Ct, Windermere, FL 34786

Property at 4243 Isabella Cir, Windermere, FL 34786, 5 beds, 6 baths

$3,290,000

5 beds6 baths5,502 sq ft

4243 Isabella Cir, Windermere, FL 34786

Property at 5036 Latrobe Dr, Windermere, FL 34786, 6 beds, 8 baths

$18,750,000

6 beds8 baths15,337 sq ft

5036 Latrobe Dr, Windermere, FL 34786

Property at 8608 Brookvale Dr, Windermere, FL 34786, 3 beds, 2.5 baths

$379,900

3 beds2.5 baths1,480 sq ft

8608 Brookvale Dr, Windermere, FL 34786

Property at 6126 Payne Stewart Dr, Windermere, FL 34786, 3 beds, 3.5 baths

$3,250,000

3 beds3.5 baths2,848 sq ft

6126 Payne Stewart Dr, Windermere, FL 34786

Property at 8142 Tibet Butler Dr, Windermere, FL 34786, 5 beds, 6.5 baths

$2,685,000

5 beds6.5 baths5,747 sq ft

8142 Tibet Butler Dr, Windermere, FL 34786

Property at 4301 Down Point Ln, Windermere, FL 34786, 5 beds, 4 baths

$2,950,000

5 beds4 baths7,153 sq ft

4301 Down Point Ln, Windermere, FL 34786

Property at 13503 Lake Cawood Dr, Windermere, FL 34786, 5 beds, 6.5 baths

$1,500,000

5 beds6.5 baths5,312 sq ft

13503 Lake Cawood Dr, Windermere, FL 34786

Viewing page 1 of 5

Based on information submitted to the MLS GRID as of Sun Oct 11 2026. 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 Windermere

There are currently 176 homes with pools for sale in Windermere at a median listing price of $1.7M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Windermere stay on the market for 99 days. Popular neighborhoods include Windsor Landing, and Isleworth. This map is refreshed with the newest listings in Windermere every 15 minutes.

In the past month, 5 homes have been sold in Windermere. In addition to houses in Windermere, there was also 1 condo, 1 townhouse, and 0 multi-family units for sale in Windermere last month. Find your dream home in Windermere 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 Windermere are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Windermere. Our Windermere real estate stats and trends will give you more information about home buying and selling trends in Windermere. If you're looking to sell your home in the Windermere area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Windermere 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 Windermere, FL

Neighborhoods

Zip Codes

Nearby Cities

Nearby Cities with Homes with Pools

Nearby Neighborhoods with Homes with Pools

Isleworth homes with pools for sale

More to explore in Windermere, FL

How to buy a house in Windermere, 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

6 Redfin agents serving Windermere

135

Deals*

4.8

Satisfaction

1276

Homes closed*

* Data from the last year

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

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.