Deer Island

Deer Island is a gated community of single family homes in Winter Garden, Florida, with a range of options priced between $469,000 and $2,199,900. There are currently a total of 4 homes for sale on Deer Island. The smallest Deer Island home presently available is a three bedroom two bathroom residence that is 2,490 square feet (2,027SF Under Air living space), and the largest of the Deer Island homes currently on the market has five beds and four baths and is a 7,796 square foot (4,945SF 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 Deer Island range from $190 to $1,240. This fee includes grounds maintenance, maintaining the community roads, the community pool, real estate taxes for common areas, Cable TV & internet, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Deer Island home.

Sports facilities include tennis courts, racquetball, and basketball court. There is also a community park, as well as walking or jogging trails.

The Deer Island HOA rules do allow homeowners to have pets. Dogs and cats are allowed.

There are four commercial airports that serve Deer Island - Orlando Executive (ORL), which is nineteen miles away; Kissimmee Gateway (ISM), which is twenty one miles away; Orlando International (MCO), which is twenty two miles away, and Orlando Sanford International (SFB), which is 30 miles away from Deer Island.

Deer Island real estate activity on the Winter Garden MLS during the past year (as of October 2025) reflects five homes changing hands, with an average asking price of $1,151,454 and an average selling price of $1,107,805. This represents a healthy list-to-sell price ratio of 96% and $245 per square foot. During this period, Deer Island homes for sale have taken an average of a long 204 or more days to sell.

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

Deer Island Homes For Sale

Under Contract

$2,199,900

MLS#MFRO6336529

17585 Deer Isle Cir
Winter Garden, FL 34787

5

4

2

5,472 SqFt

Pool

1 Acre

52 Days

Reduced

$1,299,999

$1,400,000

MLS#MFRO6332919

17556 Deer Isle Cir
Winter Garden, FL 34787

4

4

2

4,610 SqFt

Pool

1.03 Acres

63 Days

Under Contract

$916,521

MLS#MFRO6336045

11093 Hollow Bay Dr
Winter Garden, FL 34787

4

4

2

3,790 SqFt

0.36 Acres

53 Days

New Construction

Under Contract

$549,990

$568,950

MLS#MFRO6308482

11176 Hollow Bay Dr
Winter Garden, FL 34787

3

3

2

2,490 SqFt

0.12 Acres

146 Days

New Construction

4 Active Listings in Deer Island