Windsor Hill Windermere

Windsor Hill is a luxury community of single family homes in Windermere, Florida, with a range of options priced between $775,000 and $13,935,000. There are currently a total of 2 homes for sale in Windsor Hill. The smallest Windsor Hill home presently available is a five bedroom ten bathroom residence that is 3,883 square feet (2,878SF Under Air living space), and the largest of the Windsor Hill homes currently on the market has nine beds and four baths and is a 27,432 square foot (20,445SF 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 Windsor Hill are $1,335. This fee includes real estate taxes for common areas, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Windsor Hill home.

Sports facilities include tennis courts.

The Windsor Hill HOA rules do allow homeowners to have pets although there are certain breed restrictions.

There are four commercial airports that serve Windsor Hill - Orlando Executive (ORL), which is eleven miles away; Orlando International (MCO), which is fourteen miles away; Kissimmee Gateway (ISM), which is sixteen miles away, and Orlando Sanford International (SFB), which is twenty five miles away from Windsor Hill.

Windsor Hill real estate activity on the Windermere MLS during the past year (as of September 2025) reflects five homes changing hands, with an average asking price of $1,058,980 and an average selling price of $983,600. This represents a healthy list-to-sell price ratio of 93% and $185 per square foot. During this period, Windsor Hill homes for sale have taken an average of 46 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 Windsor Hill are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Windsor Hill 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.

Windsor Hill Homes For Sale

Reduced

$13,935,000

$13,995,000

MLS#MFRO6333091

9621 Windy Ridge Rd
Windermere, FL 34786

9

16

8

27,432 SqFt

Pool

2.5 Acres

57 Days

New Construction

Under Contract

$1,100,000

MLS#MFRO6340049

9641 Crown Prince Ln
Windermere, FL 34786

5

4

3

5,164 SqFt

Pool

1.04 Acres

32 Days

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2 Active Listings in Windsor Hill