Cobblestone Winter Garden

Cobblestone is a gated community of single family homes in Winter Garden, Florida, with a range of options priced between $240,000 and $699,900. There are currently a total of 2 homes for sale in Cobblestone. The smallest Cobblestone home presently available is a three bedroom two bathroom residence that is 2,425 square feet (1,901SF Under Air living space), and the largest of the Cobblestone homes currently on the market has three beds and two baths and is a 4,233 square foot (3,589SF 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 Cobblestone range from $345 to $375. This fee includes maintaining the community roads, and security. Please check the individual listing pages for the exact homeowners association fees for a particular Cobblestone home.

The Cobblestone 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 Cobblestone - Orlando Executive (ORL), which is fifteen miles away; Orlando International (MCO), which is eighteen miles away; Kissimmee Gateway (ISM), which is nineteen miles away, and Orlando Sanford International (SFB), which is twenty seven miles away from Cobblestone.

Cobblestone real estate activity on the Winter Garden MLS during the past year (as of September 2025) reflects three homes changing hands, with an average asking price of $551,333 and an average selling price of $541,333. This represents a healthy list-to-sell price ratio of 98% and $194 per square foot. During this period, Cobblestone homes for sale have taken an average of 73 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 Cobblestone are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Cobblestone 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.

Cobblestone Homes For Sale

Reduced

$610,000

$635,000

MLS#1049414

413 Country Cottage Ln
Winter Garden, FL 34787

3

3

2

3,022 SqFt

0.24 Acres

103 Days

Under Contract

$559,000

MLS#MFRO6342570

421 Cobblestone Pointe Dr
Winter Garden, FL 34787

3

2

2

2,832 SqFt

0.38 Acres

20 Days

You may also be interested in Cobblestone in Vero Beach, Cobblestone in Pembroke Pines, Cobblestone in Palm City, Cobblestone in Sarasota or Cobblestone in Zephyrhills.

2 Active Listings in Cobblestone