Windermere Real Estate

Some of the best housing options in Orange County are in the Windermere Real Estate market, with a variety of single family homes for sale priced between $500,000 and as high as $19,995,000 two to nine bedroom homes that range in size from 1,492 to 47,418 square feet. Options for Condos in Windermere range from $304,900 for an apartment with three bedrooms and two bathrooms to three bedrooms and two bathroom luxury condominiums that sell for up to $375,000. Suppose a Townhome for sale in Windermere is what you are looking for, a two-bedroom, two bathroom 1,460 square foot villa or a four-bed, three-bath home as large as 2,864 sq ft ranging in price from $330,000 to $515,000.

We have detailed information regarding 72 communities in Windermere, including 37 non-gated communities of single family homes, three condo buildings, 26 gated communities, two waterfront communities, and one country club including some new construction opportunities and open houses. Windermere real estate activity on the MLS indicates 252 properties are currently on the market (as of January 2nd, 2026). Whether relocating to Windermere from another state or upsizing or downsizing, whichever of the many luxury homes for sale in Windermere and the entire Central Florida region you choose, our professional Realtors in Windermere Florida can guide you through the home-buying process.

Windermere Homes For Sale

Reduced

$19.995 Million

$22,995,000

MLS#RX-11136385

9508 Windy Ridge Road
Windermere, FL 34786

6

14

50

47,418 SqFt

Pool

Water Front

18.163 Acres

64 Days

Reduced

$18.5 Million

$20,000,000

MLS#MFRO6275556

11900 Lake Butler Blvd
Windermere, FL 34786

7

9

6

22,728 SqFt

Pool

Water Front

3.75 Acres

293 Days

$14,250,000

Isleworth

5525 Isleworth Country Club Dr
Windermere, FL 34786

5

6

6

12,319 SqFt

Pool

1.02 Acres

228 Days

Reduced

$13,650,000

$13,995,000

Windsor Hill

9621 Windy Ridge Rd
Windermere, FL 34786

9

16

8

27,432 SqFt

Pool

2.5 Acres

151 Days

New Construction

Reduced

$11,800,000

$14,800,000

MLS#MFRO6355233

4226 Downeast Ln
Windermere, FL 34786

5

3

4

8,516 SqFt

Pool

Water Front

9.03 Acres

70 Days

$9,999,000

Keenes Pointe

6149 Grosvenor Shore Dr
Windermere, FL 34786

6

8

7

9,122 SqFt

Pool

Water Front

2.65 Acres

53 Days

Reduced

$8.995 Million

$9,995,000

Keenes Pointe

6137 Grosvenor Shore Dr
Windermere, FL 34786

6

9

5

14,934 SqFt

Pool

Water Front

2.2 Acres

274 Days

$7,750,000

Keenes Pointe

6507 Rosella Ct
Windermere, FL 34786

7

8

4

14,560 SqFt

Pool

Water Front

2.19 Acres

60 Days

$6.95 Million

Isleworth

9725 Chestnut Ridge Dr
Windermere, FL 34786

7

7

3

11,952 SqFt

Pool

Water Front

0.56 Acres

0 Days

$6,800,000

Keenes Pointe

9259 Tibet Pointe Cir
Windermere, FL 34786

5

6

4

8,225 SqFt

Pool

Water Front

2.21 Acres

220 Days

$6,395,000

MLS#MFRO6341883

9639 Westover Roberts Rd
Windermere, FL 34786

5

9

7

19,706 SqFt

Pool

Water Front

4.43 Acres

116 Days

$5.9 Million

Isleworth

9826 Laurel Valley Dr
Windermere, FL 34786

5

6

3

12,171 SqFt

Pool

Water Front

0.66 Acres

106 Days

252 Active Listings in Windermere, FL

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Living in Windermere affords you easy access to nearby golf courses, fine dining, entertainment venues and various other amenities and conveniences in the city of Windermere. The I-4 or Florida's Turnpike provide an easy transition to nearby cities such as Ocoee, Gotha, Winter Haven, Oakland, Labelle, Apopka, Montverde, Winter Garden, Orlando, Clermont, and Minneola.

Boating and watersports are integral to the Central Florida lifestyle, offering year-round access to an abundance of lakes, vibrant marine life, and a culture centered around outdoor leisure and recreation. Windermere real estate prices are directly correlated to it's proximity to these amenities.

Additionally, four local airports are easily accessible - Kissimmee Gateway (ISM) in Orlando, Orlando Executive (ORL), Orlando International (MCO), and Orlando Sanford International (SFB).

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. All listings featuring the BMLS logo are provided by Beaches Multiple Listing Service, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 Beaches MLS, Inc. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.