Windermere Trails

Windermere Trails is a community of single family homes, and townhomes in Windermere, Florida, with a range of options priced between $401,990 and $1,200,000. There are currently a total of 15 homes for sale in Windermere Trails. The smallest Windermere Trails home presently available is a three bedroom two bathroom residence that is 1,818 square feet (1,554SF Under Air living space), and the largest of the Windermere Trails homes currently on the market has seven beds and four baths and is a 5,501 square foot (4,056SF 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 $81 to $244 and $275 to $356 for a townhome. This fee includes common area maintenance, grounds maintenance, building maintenance, the community pool, real estate taxes for common areas, property insurance, 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 September 2025) reflects 35 homes changing hands, with an average asking price of $620,005 and an average selling price of $603,409. This represents a healthy list-to-sell price ratio of 97% and $186 per square foot. During this period, Windermere Trails homes for sale have taken an average of 85 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 ZFC Real Estate agent, who would happily assist you further with all your Central Florida real estate needs.

Windermere Trails Homes For Sale

$1,200,000

MLS#MFRO6327082

12023 Gold Creek Trl
Windermere, FL 34786

7

4

2

4,856 SqFt

Water Front

0.21 Acres

78 Days

$1,040,000

MLS#MFRO6341873

9197 Outlook Rock Trail
Windermere, FL 34786

5

4

2

5,501 SqFt

Pool

0.17 Acres

25 Days

Reduced

$929,999

$940,000

MLS#MFRO6315160

9257 Outlook Rock Trl
Windermere, FL 34786

5

5

3

4,840 SqFt

0.17 Acres

118 Days

Reduced

$899,000

$929,000

MLS#MFRO6322639

8752 Lookout Pointe Dr
Windermere, FL 34786

4

4

2

4,055 SqFt

Water Front

0.14 Acres

93 Days

Reduced

$799,000

$830,000

MLS#MFRO6338823

11849 Cave Run Ave
Windermere, FL 34786

4

4

2

4,506 SqFt

0.15 Acres

34 Days

Reduced

$795,000

$815,000

MLS#MFRO6328443

11922 Angle Pond Ave
Windermere, FL 34786

4

4

2

3,382 SqFt

0.15 Acres

74 Days

$779,000

MLS#MFRO6346151

8626 Crescendo Ave
Windermere, FL 34786

4

4

2

4,061 SqFt

0.14 Acres

10 Days

Reduced

$759,900

$789,900

MLS#MFRO6321333

11837 Cave Run Ave
Windermere, FL 34786

4

4

2

4,422 SqFt

0.14 Acres

94 Days

Reduced

$680,000

$695,000

MLS#MFRS5132123

8582 Powder Ridge Trl
Windermere, FL 34786

4

4

2

2,297 SqFt

0.09 Acres

56 Days

Reduced

$539,900

$550,000

MLS#MFRO6318359

8575 Lookout Pointe Dr
Windermere, FL 34786

3

3

2

2,937 SqFt

0.09 Acres

75 Days

Reduced

$539,000

$565,000

MLS#MFRO6309028

8160 Iron Mountain Trl
Windermere, FL 34786

3

3

2

2,815 SqFt

0.09 Acres

135 Days

Reduced

$525,000

$540,000

MLS#MFRO6326716

10750 Reams Rd
Windermere, FL 34786

3

3

2

2,712 SqFt

0.14 Acres

78 Days

15 Active Listings in Windermere Trails