Windermere Trails

Windermere Trails is a community of single family homes, and townhomes in Windermere, Florida, with a range of options priced between $459,000 and $915,000. There are currently a total of 16 homes for sale in Windermere Trails. The smallest Windermere Trails home presently available is a three bedroom two bathroom residence that is 2,297 square feet (1,600SF Under Air living space), and the largest of the Windermere Trails homes currently on the market has five beds and four baths and is a 7,201 square foot (3,724SF Under Air) residence.

Property management fees in Orange County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Windermere Trails range from $85 to $363 and $285 for a townhome. This fee includes common area maintenance, grounds maintenance, building maintenance, the community pool, real estate taxes for common areas, property insurance, trash removal, pest control, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Windermere Trails home.

Windermere Trails amenities include a clubhouse, swimming pool, and a state-of-the-art fitness center. Sports facilities include tennis courts. There is also a community park, a playground, a dog park, as well as walking or jogging trails.

The Windermere Trails HOA rules do allow homeowners to have pets although there are certain breed restrictions. Dogs and cats are allowed.

There are four commercial airports that serve Windermere Trails - Kissimmee Gateway (ISM), which is thirteen miles away; Orlando International (MCO), which is fifteen miles away; Orlando Executive (ORL), which is sixteen miles away, and Orlando Sanford International (SFB), which is 31 miles away from Windermere Trails.

Windermere Trails real estate activity on the Windermere MLS during the past year (as of June 2026) reflects twenty seven homes changing hands, with an average asking price of $656,585 and an average selling price of $638,144. This represents a healthy list-to-sell price ratio of 97% and $187 per square foot. During this period, Windermere Trails homes for sale have taken an average of 90 days to sell.

In addition, there are numerous other communities in Windermere to choose from, or you may browse all available Windermere Real Estate, including some new construction opportunities. Homes for sale in Windermere Trails are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Windermere Trails hits the market. You can also always contact your BEX Realty agent, who would happily assist you further with all your Central Florida real estate needs.

Windermere Trails Homes For Sale

$1,150,000

MLS#MFRO6413196

8394 Lookout Pointe Dr
Windermere, FL 34786

5

4

2

4,916 SqFt

Pool

0.17 Acres

16 Days

$1,125,000

MLS#MFRO6413948

9117 Outlook Rock Trl
Windermere, FL 34786

5

5

3

5,917 SqFt

Pool

0.18 Acres

5 Days

$915,000

MLS#MFRS5145642

9150 Outlook Rock Trl
Windermere, FL 34786

4

3

2

6,544 SqFt

Pool

0.15 Acres

104 Days

$900,000

MLS#MFRO6382068

11835 Gold Creek Trl
Windermere, FL 34786

4

5

2

4,412 SqFt

0.17 Acres

132 Days

Under Contract

$879,999

$899,990

MLS#MFRS5143447

9257 Outlook Rock Trl
Windermere, FL 34786

5

5

3

7,201 SqFt

0.17 Acres

136 Days

Under Contract

$825,000

$840,000

MLS#MFRO6410762

8715 Quiet Meadows Trl
Windermere, FL 34786

4

4

2

3,388 SqFt

Pool

0.2 Acres

30 Days

Under Contract

$750,000

MLS#MFRO6392757

11903 Cave Run Ave
Windermere, FL 34786

4

4

2

4,365 SqFt

0.15 Acres

93 Days

Reduced

$680,000

$690,000

MLS#MFRS5144276

8552 Powder Ridge Trl
Windermere, FL 34786

5

4

2

4,290 SqFt

0.09 Acres

119 Days

Reduced

$670,000

$695,000

MLS#MFRS5132123

8582 Powder Ridge Trl
Windermere, FL 34786

4

4

2

2,297 SqFt

0.09 Acres

323 Days

$560,000

MLS#MFRO6371960

8225 Bryce Canyon Ave
Windermere, FL 34786

4

3

2

2,554 SqFt

0.13 Acres

167 Days

Reduced

$509,000

$530,000

MLS#MFRO6389547

8272 Bryce Canyon Ave
Windermere, FL 34786

3

3

2

2,588 SqFt

0.09 Acres

106 Days

$495,000

MLS#MFRO6409301

11822 Silverlake Park Dr
Windermere, FL 34786

3

3

2

2,501 SqFt

0.09 Acres

27 Days

16 Active Listings in Windermere Trails