Windsor At Waterside

Windsor At Waterside is a community of single family homes, and townhomes in Kissimmee, Florida, with a range of options priced between $395,000 and $849,000. There are currently a total of 101 homes for sale in Windsor At Waterside. The smallest Windsor At Waterside home presently available is a ten bedroom four bathroom residence that is 2,102 square feet, and the largest of the Windsor At Waterside homes currently on the market has nine beds and six baths and is a 6,548 square foot (4,396SF 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 Windsor At Waterside range from $516 to $721 and $420 to $672 for a townhome. This fee includes common area maintenance, grounds maintenance, building maintenance, maintaining the community roads, the community pool, and security. Also included is a 24-hour guard, real estate taxes for common areas, property insurance, water, electric, trash removal, sewer, pest control, Cable TV & internet, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Windsor At Waterside home.

Windsor At Waterside amenities include a clubhouse, swimming pool, spa / hot tub, and a state-of-the-art fitness center. Sports facilities include a championship golf course, tennis courts, pickleball courts, racquetball, and basketball court.

Boating enthusiasts will love the fact that the community has boat facilities including a boat dock. There is also a community park, a playground, as well as walking or jogging trails.

The Windsor At Waterside HOA rules do allow homeowners to have pets although there are certain breed restrictions. There is a limit of how many pets you may have, and there is a restriction on pet size. Dogs and cats are allowed.

There are four commercial airports that serve Windsor At Waterside - Kissimmee Gateway (ISM), which is thirteen miles away; Orlando International (MCO), which is twenty two miles away; Orlando Executive (ORL), which is twenty five miles away, and Lakeland Linder International (LAL), which is 32 miles away from Windsor At Waterside.

Windsor At Waterside real estate activity on the Kissimmee MLS during the past year (as of March 2026) reflects 82 homes changing hands, with an average asking price of $548,647 and an average selling price of $534,086. This represents a healthy list-to-sell price ratio of 97% and $141 per square foot. During this period, Windsor At Waterside homes for sale have taken an average of 178 days to sell.

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

Windsor At Waterside Homes For Sale

$849,000

MLS#MFRS5141136

1949 Nice Ct
Kissimmee, FL 34747

9

6

2

5,214 SqFt

Pool

0.15 Acres

78 Days

$790,000

MLS#MFRO6382041

8811 Macapa Dr
Kissimmee, FL 34747

9

6

2

5,214 SqFt

Pool

0.18 Acres

45 Days

Reduced

$789,000

$849,990

MLS#MFRO6247686

8844 Corcovado Dr
Kissimmee, FL 34747

8

6

2

4,481 SqFt

Pool

0.13 Acres

530 Days

$785,000

MLS#MFRO6383464

1885 Gobi Dr
Kissimmee, FL 34747

8

6

2

4,860 SqFt

Pool

0.13 Acres

42 Days

Reduced

$785,000

$790,000

MLS#MFRO6383484

2199 Tripoli Ct
Kissimmee, FL 34747

9

6

2

4,860 SqFt

Pool

0.15 Acres

41 Days

$749,000

MLS#MFRO6339934

1940 Nice Ct
Kissimmee, FL 34747

9

6

4,396 SqFt

Pool

0.13 Acres

215 Days

Reduced

$737,000

$747,000

MLS#MFRS5119586

1610 Lima Ave
Kissimmee, FL 34747

8

6

2

4,041 SqFt

Pool

0.15 Acres

426 Days

$720,000

MLS#MFRO6365123

2100 Rome Dr
Kissimmee, FL 34747

7

6

2

4,051 SqFt

Pool

0.12 Acres

117 Days

$720,000

MLS#MFRS5142261

1599 Lima Ave
Kissimmee, FL 34747

8

6

2

4,860 SqFt

Pool

0.16 Acres

67 Days

$699,900

MLS#MFRS5146750

8825 Corcovado Dr
Kissimmee, FL 34747

8

6

2

4,860 SqFt

Pool

0.16 Acres

2 Days

Reduced

$699,000

$710,000

MLS#MFRO6252445

8832 Macapa Dr
Kissimmee, FL 34747

8

6

2

4,860 SqFt

Pool

0.13 Acres

518 Days

Reduced

$699,000

$750,000

MLS#MFRO6292964

1639 Lima Ave W
Kissimmee, FL 34747

8

6

2

4,860 SqFt

Pool

0.13 Acres

371 Days

101 Active Listings in Windsor At Waterside