Windsong Kissimmee

Windsong is a community of single family homes in Kissimmee, Florida, with a range of options priced between $64,900 and $345,000. The smallest Windsong home in the community is a three bedroom two bathroom residence that is 1,260 square feet (1,173SF Under Air living space), and the largest of the Windsong homes has five beds and three baths and is a 3,720 square foot (3,157SF Under Air) residence.

Property management fees in Osceola County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Windsong range from $120 to $300. Please check the individual listing pages for the exact homeowners association fees for a particular Windsong home.

The Windsong HOA rules do allow homeowners to have pets.

There are four commercial airports that serve Windsong - Kissimmee Gateway (ISM), which is three miles away; Orlando International (MCO), which is nine miles away; Orlando Executive (ORL), which is sixteen miles away, and Orlando Sanford International (SFB), which is 33 miles away from Windsong.

Windsong real estate activity on the Kissimmee MLS during the past year (as of September 2025) reflects that just one home changed hands during this time. Offered with an asking price of $305,000 and selling for $300,000, this represents a list/sell ratio of 98%. It took 57 days from the time it was listed until it sold.

In addition, there are numerous other communities in Kissimmee to choose from, or you may browse all available Kissimmee 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

SOLD 03/27/17

$144,900

MLS#MFRO5490231

1120 Windway Cir
Kissimmee, FL 34744

3

2

1

1,467 SqFt

0.26 Acres

SOLD 01/04/23

$330,000

$340,000

MLS#MFRO6050608

1011 Longwind Way
Kissimmee, FL 34744

3

3

2

1,260 SqFt

0.29 Acres

SOLD 11/27/23

$340,000

MLS#MFRG5072101

1145 Windway Cir
Kissimmee, FL 34744

3

3

2

1,260 SqFt

0.25 Acres

SOLD 01/31/23

$330,000

MLS#MFRS5077360

1145 Windway Cir
Kissimmee, FL 34744

3

3

2

2,019 SqFt

0.25 Acres

SOLD 06/10/22

$345,000

MLS#MFRS5066559

1015 Windway Cir
Kissimmee, FL 34744

3

2

2

1,224 SqFt

0.25 Acres

SOLD 06/10/22

$345,000

MLS#AX-11197729

1015 Windway Cir
Kissimmee, FL 34744

3

2

2

SOLD 11/03/17

$209,900

MLS#MFRS4852769

1030 Longwind Way
Kissimmee, FL 34744

3

2

1

1,851 SqFt

Pool

0.29 Acres

SOLD 06/24/15

$230,000

$245,000

MLS#MFRS4811168

1160 Windway Cir
Kissimmee, FL 34744

5

4

1

3,720 SqFt

0.25 Acres

SOLD 02/02/18

$180,000

$189,900

MLS#MFRO5546106

995 Windway Cir
Kissimmee, FL 34744

3

2

2

1,920 SqFt

0.25 Acres

SOLD 12/26/13

$84,900

MLS#MFRS4720205

995 Windway Cir
Kissimmee, FL 34744

3

2

2

1,920 SqFt

0.25 Acres

SOLD 01/06/15

$87,500

$104,000

MLS#MFRS4800427

1170 Windway Cir
Kissimmee, FL 34744

3

2

1

1,620 SqFt

0.25 Acres

SOLD 10/14/22

$324,000

MLS#MFRO6036373

985 Windway Cir
Kissimmee, FL 34744

3

3

2

1,260 SqFt

0.27 Acres

SOLD 08/25/15

$134,900

MLS#MFRO5371960

1180 Windway Cir
Kissimmee, FL 34744

3

2

1

1,412 SqFt

0.25 Acres

SOLD 01/13/23

$319,900

MLS#MFRS5076946

2295 Softwind Ct
Kissimmee, FL 34744

4

3

1,644 SqFt

0.25 Acres

SOLD 01/07/13

$64,900

MLS#MFRS4700863

1195 Windway Cir
Kissimmee, FL 34744

3

2

1

1,963 SqFt

0.25 Acres

SOLD 12/17/21

$285,000

MLS#MFRS5058830

955 Windway Cir
Kissimmee, FL 34744

3

2

2

1,224 SqFt

Pool

0.25 Acres

SOLD 06/20/14

$135,000

MLS#MFRS4720097

955 Windway Cir
Kissimmee, FL 34744

3

2

2

1,684 SqFt

Pool

0.25 Acres

SOLD 12/30/15

$135,000

MLS#MFRS4823269

2114 Wind Jammer Ct
Kissimmee, FL 34744

3

2

1

1,467 SqFt

Pool

0.27 Acres

SOLD 08/05/25

$305,000

MLS#MFRV4941871

950 Windway Cir
Kissimmee, FL 34744

3

2

1

2,319 SqFt

Water Front

0.25 Acres

SOLD 07/08/22

$329,900

MLS#MFRT3378345

935 Windway Cir
Kissimmee, FL 34744

3

2

2

1,504 SqFt

0.25 Acres

SOLD 07/27/17

$190,000

MLS#MFRS4847308

1245 Windway Cir
Kissimmee, FL 34744

3

2

2

2,508 SqFt

0.26 Acres

SOLD 07/15/22

$325,000

MLS#MFRS5069089

1240 Windway Cir
Kissimmee, FL 34744

3

2

1

1,533 SqFt

Pool

0.26 Acres

SOLD 09/28/17

$177,500

MLS#MFRO5522225

910 Windway Cir
Kissimmee, FL 34744

3

2

2

1,900 SqFt

0.36 Acres

SOLD 02/12/13

$114,900

$149,900

MLS#MFRO5081079

1260 Windway Cir
Kissimmee, FL 34744

5

3

2,731 SqFt

0.3 Acres

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

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0 Active Listings in Windsong