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. The smallest Cobblestone home in the community 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 has five beds and three 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 $100 to $330. 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 November 2025) reflects four homes changing hands, with an average asking price of $553,250 and an average selling price of $540,675. This represents a healthy list-to-sell price ratio of 98% and $193 per square foot. During this period, Cobblestone homes for sale have taken an average of 58 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

SOLD 05/30/23

$499,000

$529,900

MLS#MFRG5064001

240 Country Cottage Ln
Winter Garden, FL 34787

4

3

2

2,668 SqFt

0.28 Acres

SOLD 10/10/25

$559,000

MLS#MFRO6342570

421 Cobblestone Pointe Dr
Winter Garden, FL 34787

3

2

2

2,832 SqFt

0.38 Acres

SOLD 02/25/22

$585,000

MLS#MFRO5995491

312 Country Cottage Ln
Winter Garden, FL 34787

5

3

2

3,583 SqFt

0.24 Acres

SOLD 01/27/15

$310,000

MLS#MFRO5330748

241 Country Cottage Ln
Winter Garden, FL 34787

3

3

2

3,516 SqFt

Pool

0.24 Acres

SOLD 02/03/22

$628,000

MLS#MFRO5995244

307 Country Cottage Ln
Winter Garden, FL 34787

4

3

2

3,018 SqFt

0.24 Acres

SOLD 05/20/24

$655,000

MLS#MFRO6192761

235 Country Cottage Ln
Winter Garden, FL 34787

3

2

2

2,915 SqFt

Pool

0.26 Acres

SOLD 09/17/14

$240,000

$275,000

MLS#MFRO5191705

349 Country Cottage Ln
Winter Garden, FL 34787

4

3

2

3,523 SqFt

0.24 Acres

SOLD 04/18/22

$588,780

MLS#MFRO6010767

235 Country Cottage Ln
Winter Garden, FL 34787

4

2

2

2,238 SqFt

Pool

0.26 Acres

SOLD 08/14/25

$555,000

MLS#MFRO6324650

218 Black Springs Ln
Winter Garden, FL 34787

4

2

2

2,782 SqFt

0.27 Acres

SOLD 04/15/24

$625,000

MLS#MFRO6174780

453 Black Springs Ln
Winter Garden, FL 34787

4

2

3

3,045 SqFt

0.27 Acres

SOLD 11/05/21

$445,000

MLS#MFRO5973388

344 Black Springs Ln
Winter Garden, FL 34787

3

2

2

2,605 SqFt

Pool

0.24 Acres

SOLD 04/28/17

$369,800

MLS#MFRO5496331

302 Black Springs Ln
Winter Garden, FL 34787

5

3

2

4,219 SqFt

0.24 Acres

SOLD 12/28/16

$274,900

MLS#MFRO5470620

248 Black Springs Ln
Winter Garden, FL 34787

3

2

2

2,667 SqFt

0.24 Acres

SOLD 03/14/24

$549,900

MLS#MFRO6175768

344 Black Springs Ln
Winter Garden, FL 34787

3

2

2

2,604 SqFt

Pool

0.24 Acres

SOLD 05/21/25

$549,000

MLS#MFRO6296111

350 Black Springs Ln
Winter Garden, FL 34787

3

2

2

2,569 SqFt

Pool

0.24 Acres

SOLD 12/03/14

$249,900

MLS#MFRO5322686

242 Black Springs Ln
Winter Garden, FL 34787

3

2

2

2,425 SqFt

0.24 Acres

SOLD 03/18/24

$549,900

MLS#1003531

344 Black Springs
Winter Garden, FL 34787

3

2

2

2,604 SqFt

Pool

0.24 Acres

SOLD 08/22/25

$550,000

$580,000

MLS#MFRO6310754

309 Black Springs Ln
Winter Garden, FL 34787

3

3

2

3,013 SqFt

0.26 Acres

SOLD 05/09/24

$699,900

MLS#MFRG5080496

339 Black Springs Ln
Winter Garden, FL 34787

5

4

2

4,233 SqFt

Pool

0.26 Acres

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We do not have any properties available for sale in Cobblestone.

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0 Active Listings in Cobblestone