Winter Hill

Winter Hill is a community of single family homes in Orlando, Florida, with a range of options priced between $120,000 and $479,900. The smallest Winter Hill home in the community is a three bedroom two bathroom residence that is 1,550 square feet (1,220SF Under Air living space), and the largest of the Winter Hill homes has four beds and three baths and is a 2,932 square foot (2,249SF 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 range from $204 to $350. 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 June 2026) reflects five homes changing hands, with an average asking price of $368,140 and an average selling price of $364,390. This represents a healthy list-to-sell price ratio of 99% and $186 per square foot. During this period, Winter Hill homes for sale have taken an average of 88 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 BEX Realty agent, who would happily assist you further with all your Central Florida real estate needs.

Winter Hill Homes For Sale

SOLD 10/25/16

$265,000

$275,000

MLS#MFRO5460417

107 Killington Way
Orlando, FL 32835

4

3

2

2,555 SqFt

0.25 Acres

SOLD 05/31/13

$209,900

MLS#MFRO5149057

204 Killington Ct
Orlando, FL 32835

3

2

2

2,472 SqFt

Pool

0.22 Acres

SOLD 06/20/24

$479,900

MLS#MFRO6199256

119 Killington Way
Orlando, FL 32835

4

3

2

2,503 SqFt

0.27 Acres

SOLD 03/27/26

$385,000

MLS#MFRG5105927

222 Killington Ct
Orlando, FL 32835

3

2

2

2,510 SqFt

Pool

0.19 Acres

SOLD 04/02/14

$189,000

MLS#MFRO5214706

202 Killington Way
Orlando, FL 32835

3

2

2

2,236 SqFt

0.24 Acres

SOLD 10/29/21

$380,000

MLS#MFRS5056854

8006 Addison Ct
Orlando, FL 32835

4

2

2

1,970 SqFt

Pool

0.19 Acres

SOLD 05/29/14

$199,990

$215,000

MLS#MFRO5220878

239 Killington Way
Orlando, FL 32835

4

2

2

2,427 SqFt

0.19 Acres

SOLD 08/22/17

$289,900

$299,900

MLS#MFRO5521291

334 Killington Way
Orlando, FL 32835

4

2

2

2,932 SqFt

Pool

0.22 Acres

SOLD 09/23/22

$380,000

MLS#MFRO6048607

317 Killington Way
Orlando, FL 32835

4

2

2

2,560 SqFt

0.19 Acres

SOLD 04/29/15

$225,000

MLS#MFRO5353801

300 Snowshoe Ct
Orlando, FL 32835

3

3

2

2,591 SqFt

0.2 Acres

SOLD 12/03/25

$339,999

MLS#MFRO6359622

8044 Aspencrest Ct
Orlando, FL 32835

3

2

2

1,550 SqFt

0.14 Acres

SOLD 11/21/22

$379,999

$399,999

MLS#MFRO6059604

8048 Aspencrest Ct
Orlando, FL 32835

4

2

2

1,629 SqFt

0.15 Acres

SOLD 04/11/14

$120,000

MLS#MFRO5209919

8008 Aspencrest Ct
Orlando, FL 32835

3

2

2

1,701 SqFt

Pool

0.14 Acres

SOLD 01/27/26

$339,900

MLS#MFRO6364477

8000 Aspencrest Ct
Orlando, FL 32835

3

2

2

1,816 SqFt

0.25 Acres

SOLD 04/30/26

$445,900

$484,900

MLS#MFRO6343225

8076 Aspencrest Ct
Orlando, FL 32835

4

3

2

2,158 SqFt

Pool

0.2 Acres

SOLD 11/10/14

$170,000

$180,000

MLS#MFRS4803080

8076 Aspencrest Ct
Orlando, FL 32835

4

3

2

2,158 SqFt

Pool

0.2 Acres

SOLD 05/19/26

$329,900

MLS#MFRO6384462

8013 Aspencrest Ct
Orlando, FL 32835

3

2

2

1,772 SqFt

0.19 Acres

SOLD 10/12/15

$125,000

MLS#MFRO5380584

8005 Aspencrest Ct
Orlando, FL 32835

3

2

2

1,804 SqFt

Pool

0.15 Acres

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We do not have any properties available for sale in Winter Hill.

0 Active Listings in Winter Hill