Windsong Winter Park

Windsong is a community of single family homes in Winter Park, Florida, with a range of options priced between $484,000 and $5,695,000. There are currently a total of 4 homes for sale in Windsong. The smallest Windsong home presently available is a three bedroom two bathroom residence that is 2,302 square feet (1,936SF Under Air living space), and the largest of the Windsong homes currently on the market has six beds and seven baths and is a 12,137 square foot (8,930SF 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 Windsong range from $235 to $735. This fee includes the community pool, real estate taxes for common areas, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Windsong home.

Windsong amenities include a clubhouse, and swimming pool. There is also a community park, as well as a playground.

The Windsong HOA rules do allow homeowners to have pets although there are certain breed restrictions.

There are four commercial airports that serve Windsong - Orlando Executive (ORL), which is three miles away; Orlando International (MCO), which is eleven miles away; Orlando Sanford International (SFB), which is fourteen miles away, and Kissimmee Gateway (ISM), which is twenty two miles away from Windsong.

Windsong real estate activity on the Winter Park MLS during the past year (as of December 2025) reflects five homes changing hands, with an average asking price of $2,713,000 and an average selling price of $2,532,000. This represents a healthy list-to-sell price ratio of 93% and $452 per square foot. During this period, Windsong homes for sale have taken an average of 77 days to sell.

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

Windsong Homes For Sale

$8.95 Million

MLS#MFRO6350054

1120 Preserve Point Dr
Winter Park, FL 32789

7

11

4

13,377 SqFt

Pool

Water Front

1.63 Acres

71 Days

$8.5 Million

MLS#MFRO6312768

1112 Preserve Point Dr
Winter Park, FL 32789

5

6

3

9,159 SqFt

Pool

Water Front

1.94 Acres

202 Days

Reduced

$1,525,000

$1,549,000

MLS#MFRO6357486

1408 Chapman Cir
Winter Park, FL 32789

4

4

2

3,717 SqFt

Pool

0.18 Acres

42 Days

Reduced

$1,349,950

$1,699,000

MLS#MFRO6257912

1429 Chapman Cir
Winter Park, FL 32789

4

4

2

3,774 SqFt

0.14 Acres

396 Days

You may also be interested in Windsong in Fort Myers, Windsong in Kissimmee, Windsong in Leesburg, Windsong in Bonita Springs or Windsong in Flagler Beach.

4 Active Listings in Windsong