Carolyn Estates

Carolyn Estates is a community of single family homes in Winter Park, Florida, with a range of options priced between $179,900 and $495,000. The smallest Carolyn Estates home in the community is a three bedroom two bathroom residence that is 1,550 square feet, and the largest of the Carolyn Estates homes has four beds and two baths and is a 2,836 square foot (2,014SF 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 Carolyn Estates are $100. This fee includes grounds maintenance. Please check the individual listing pages for the exact homeowners association fees for a particular Carolyn Estates home.

The Carolyn Estates HOA rules do allow homeowners to have pets.

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

Carolyn Estates real estate activity on the Winter Park MLS during the past year (as of March 2026) reflects that just one home changed hands during this time. Offered with an asking price of $478,700 and selling for $465,000, this represents a list/sell ratio of 97%. It took 100 days from the time it was listed until it sold.

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

Carolyn Estates Homes For Sale

SOLD 07/30/25

$478,700

$495,700

MLS#MFRA4644849

1776 E Cheryl Dr
Winter Park, FL 32792

4

2

2

2,836 SqFt

Pool

0.25 Acres

SOLD 07/18/22

$495,000

MLS#MFRO6026815

1788 E Cheryl Dr
Winter Park, FL 32792

4

2

2

2,556 SqFt

Pool

0.24 Acres

SOLD 10/23/24

$335,000

MLS#MFRTB8309977

1748 W Cheryl Dr
Winter Park, FL 32792

4

2

2

2,338 SqFt

0.2 Acres

SOLD 01/14/25

$480,000

MLS#MFRO6263521

1748 W Cheryl Dr
Winter Park, FL 32792

3

2

2

2,338 SqFt

0.23 Acres

SOLD 06/04/24

$425,000

$475,999

MLS#MFRS5100154

1744 W Cheryl Dr
Winter Park, FL 32792

4

2

2

2,201 SqFt

0.18 Acres

SOLD 09/08/22

$350,000

MLS#MFRO6055662

1796 E Cheryl Dr
Winter Park, FL 32792

3

2

2

1,906 SqFt

0.19 Acres

SOLD 04/28/23

$446,900

$449,900

MLS#MFRO6091664

1796 E Cheryl Dr
Winter Park, FL 32792

3

2

2

2,502 SqFt

0.19 Acres

SOLD 10/26/15

$184,900

MLS#MFRO5355362

4211 Beau James Ct
Winter Park, FL 32792

4

2

2

2,666 SqFt

Pool

0.3 Acres

SOLD 11/03/22

$440,000

MLS#MFRO6056057

1741 W Cheryl Dr
Winter Park, FL 32792

3

2

2

1,550 SqFt

Pool

0.19 Acres

SOLD 04/05/24

$485,000

MLS#MFRO6182771

1741 W Cheryl Dr
Winter Park, FL 32792

3

2

2

1,550 SqFt

Pool

0.19 Acres

SOLD 01/05/23

$455,000

$485,000

MLS#MFRO6047067

1800 E Cheryl Dr
Winter Park, FL 32792

4

2

2

2,480 SqFt

Pool

0.19 Acres

SOLD 07/12/22

$425,000

MLS#MFRO6030732

1737 W Cheryl Dr
Winter Park, FL 32792

4

2

2

2,062 SqFt

Pool

0.19 Acres

SOLD 10/04/17

$239,900

$269,900

MLS#MFRO5520309

1732 W Cheryl Dr
Winter Park, FL 32792

3

2

2

2,316 SqFt

Pool

0.17 Acres

SOLD 08/17/15

$199,900

MLS#MFRO5361467

1728 W Cheryl Dr
Winter Park, FL 32792

3

2

2

2,734 SqFt

Pool

0.17 Acres

SOLD 12/21/23

$445,000

MLS#MFRO6158267

1724 W Cheryl Dr
Winter Park, FL 32792

3

2

2

2,242 SqFt

0.18 Acres

SOLD 04/13/16

$245,000

$249,900

MLS#MFRO5421328

1720 W Cheryl Dr
Winter Park, FL 32792

4

2

2

2,191 SqFt

0.19 Acres

SOLD 08/30/13

$179,900

MLS#MFRO5172227

1716 W Cheryl Dr
Winter Park, FL 32792

3

2

2

2,416 SqFt

Pool

0.2 Acres

SOLD 12/20/21

$349,999

MLS#MFRO5983261

1708 W Cheryl Dr
Winter Park, FL 32792

4

2

2

1,818 SqFt

0.23 Acres

SOLD 08/07/23

$447,999

MLS#MFRS5087584

1704 W Cheryl Dr
Winter Park, FL 32792

4

2

2

2,513 SqFt

0.26 Acres

SOLD 08/10/23

$450,000

MLS#MFRO6125593

1852 E Cheryl Dr
Winter Park, FL 32792

4

2

2

2,788 SqFt

Pool

0.37 Acres

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We do not have any properties available for sale in Carolyn Estates.

0 Active Listings in Carolyn Estates