Winter Hill

Winter Hill is a community of single family homes in Orlando, Florida, with a range of options priced between $329,900 and $550,000. There are currently a total of 4 homes for sale in Winter Hill. The smallest Winter Hill home presently available is a three bedroom two bathroom residence that is 1,772 square feet (1,220SF Under Air living space), and the largest of the Winter Hill homes currently on the market has four beds and three baths and is a 2,510 square foot (2,057SF 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 Winter Hill are $208. This fee includes real estate taxes for common areas, and property insurance. Please check the individual listing pages for the exact homeowners association fees for a particular Winter Hill home.

The Winter Hill HOA rules do allow homeowners to have pets. Dogs and cats are allowed.

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

Winter Hill real estate activity on the Orlando MLS during the past year (as of March 2026) reflects two homes changing hands, with an average asking price of $339,950 and an average selling price of $335,000. This represents a healthy list-to-sell price ratio of 99% and $199 per square foot. During this period, Winter Hill homes for sale have taken an average of just 5 days to sell.

In addition, there are numerous other communities in Orlando to choose from, or you may browse all available Orlando Real Estate, including some new construction opportunities. Homes for sale in Winter Hill are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Winter 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.

Winter Hill Homes For Sale

$550,000

MLS#MFRO6388327

119 Killington Way
Orlando, FL 32835

4

3

2

2,503 SqFt

0.27 Acres

9 Days

Reduced

$445,900

$484,900

MLS#MFRO6343225

8076 Aspencrest Ct
Orlando, FL 32835

4

3

2

2,158 SqFt

Pool

0.2 Acres

186 Days

Under Contract

$385,000

MLS#MFRG5105927

222 Killington Ct
Orlando, FL 32835

3

2

2

2,510 SqFt

Pool

0.19 Acres

54 Days

Under Contract

$329,900

MLS#MFRO6384462

8013 Aspencrest Ct
Orlando, FL 32835

3

2

2

1,772 SqFt

0.19 Acres

23 Days

4 Active Listings in Winter Hill