Windward Cay Winter Garden

Windward Cay is a gated community of single family homes in Winter Garden, Florida, with a range of options priced between $339,900 and $1,050,000. The smallest Windward Cay home in the community is a four bedroom three bathroom residence that is 3,599 square feet (2,687SF Under Air living space), and the largest of the Windward Cay homes has five beds and four baths and is a 4,627 square foot (3,519SF 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 Windward Cay range from $100 to $265. This fee includes grounds maintenance, maintaining the community roads, and security. Please check the individual listing pages for the exact homeowners association fees for a particular Windward Cay home.

The Windward Cay HOA rules do allow homeowners to have pets. Dogs and cats are allowed.

There are four commercial airports that serve Windward Cay - Orlando Executive (ORL), which is sixteen miles away; Kissimmee Gateway (ISM), which is seventeen miles away; Orlando International (MCO), which is eighteen miles away, and Orlando Sanford International (SFB), which is twenty nine miles away from Windward Cay.

Windward Cay real estate activity on the Winter Garden MLS during the past year (as of November 2025) reflects that just one home changed hands during this time. Offered with an asking price of $1,050,000 and selling for $998,000, this represents a list/sell ratio of 95%. It took just 13 days from the time it was listed until it sold.

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 Windward Cay are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Windward Cay 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.

Windward Cay Homes For Sale

SOLD 12/20/22

$659,999

$749,000

MLS#MFRR4906008

3626 Turningwind Ln
Winter Garden, FL 34787

5

3

3

4,206 SqFt

Water Front

0.25 Acres

SOLD 03/09/22

$579,800

MLS#MFRO5987251

3524 Turningwind Ln
Winter Garden, FL 34787

5

4

3

4,110 SqFt

0.24 Acres

SOLD 08/08/24

$899,900

MLS#MFRO6216001

3424 Turningwind Ln
Winter Garden, FL 34787

5

4

3

4,145 SqFt

Pool

0.24 Acres

SOLD 08/02/24

$859,900

MLS#MFRG5083656

3543 Turningwind Ln
Winter Garden, FL 34787

6

4

3

4,506 SqFt

Pool

0.24 Acres

SOLD 01/13/24

$939,000

MLS#MFRO6158712

3418 Turningwind Ln
Winter Garden, FL 34787

5

4

2

4,627 SqFt

Pool

Water Front

0.25 Acres

SOLD 06/20/25

$1,050,000

MLS#MFRO6297996

3418 Turningwind Ln
Winter Garden, FL 34787

5

4

2

4,627 SqFt

Pool

0.25 Acres

SOLD 06/21/22

$700,000

$849,900

MLS#MFRO6015212

3415 Tempest Way
Winter Garden, FL 34787

5

3

3

4,152 SqFt

Pool

0.24 Acres

SOLD 02/28/23

$750,000

MLS#MFRO6081758

3415 Tempest Way
Winter Garden, FL 34787

5

3

3

4,152 SqFt

Pool

0.24 Acres

SOLD 10/28/21

$588,800

MLS#MFRO5975028

14043 Zephermoor Ln
Winter Garden, FL 34787

5

3

3

4,163 SqFt

Pool

0.26 Acres

SOLD 06/07/22

$628,800

MLS#MFRO6021634

13915 Zephermoor Ln
Winter Garden, FL 34787

4

3

3

3,599 SqFt

Pool

0.24 Acres

SOLD 08/08/13

$339,900

MLS#MFRO5168050

13915 Zephermoor Ln
Winter Garden, FL 34787

4

3

3

3,599 SqFt

Pool

0.24 Acres

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We do not have any properties available for sale in Windward Cay.

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0 Active Listings in Windward Cay