Windsor Hills

Windsor Hills is a gated community of single family homes, condos, and townhomes in Kissimmee, Florida, with a range of options priced between $274,500 and $740,000. There are currently a total of 54 homes for sale in Windsor Hills. The smallest Windsor Hills home presently available is a four bedroom three bathroom residence that is 1,081 square feet, and the largest of the Windsor Hills homes currently on the market has six beds and five baths and is a 3,612 square foot (2,812SF 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 Hills range from $488 to $2,050 and range from $737 to $1,120 for a Windsor Hills condo and $445 to $1,117 for a townhome. This fee includes common area maintenance, grounds maintenance, building maintenance, maintaining the community roads, roof repair and replacement, and the community pool. Also included is security, 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 Hills home.

The Windsor Hills community offers a plethora of amenities for its residents to enjoy, including a clubhouse, swimming pool, spa / hot tub, cabana, a state-of-the-art fitness center, billiards room, and hobby room. Sports facilities include a championship golf course, tennis courts, pickleball courts, basketball court, and shuffleboard. Onsite dining venues consist of a restaurant, picnic area, and a barbecue area. There is also a community park, a playground, a dog park, as well as walking or jogging trails.

The Windsor Hills 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 Hills - Kissimmee Gateway (ISM), which is ten miles away; Orlando International (MCO), which is nineteen miles away; Orlando Executive (ORL), which is twenty two miles away, and Lakeland Linder International (LAL), which is 35 miles away from Windsor Hills.

Windsor Hills real estate activity on the Kissimmee MLS during the past year (as of November 2025) reflects 81 homes changing hands, with an average asking price of $488,318 and an average selling price of $469,286. This represents a healthy list-to-sell price ratio of 96% and $222 per square foot. During this period, Windsor Hills homes for sale have taken an average of 99 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 Hills are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Windsor Hills 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 Hills Homes For Sale

Featured

$620,000

MLS#MFRTB8409242

Kissimmee, FL 34747

5

5

2

3,030 SqFt

Pool

0.14 Acres

118 Days

$740,000

MLS#MFRO6298445

7790 Teascone Blvd
Kissimmee, FL 34747

5

5

2

2,297 SqFt

Pool

0.32 Acres

216 Days

Under Contract

$725,000

MLS#MFRO6352182

2677 Manesty Ln
Kissimmee, FL 34747

6

4

2

3,568 SqFt

Pool

0.16 Acres

32 Days

Reduced

$725,000

$750,000

MLS#MFRO6270582

2715 Manesty Ln
Kissimmee, FL 34747

6

4

2

2,812 SqFt

Pool

0.27 Acres

309 Days

Reduced

$714,900

$729,500

MLS#MFRO6297216

2509 Archfeld Blvd
Kissimmee, FL 34746

6

4

2

3,612 SqFt

Pool

0.14 Acres

221 Days

Reduced

$699,000

$729,900

MLS#MFRO6318132

2669 Manesty Ln
Kissimmee, FL 34747

6

4

2

3,548 SqFt

Pool

0.33 Acres

154 Days

Under Contract

$689,000

$709,000

MLS#MFRO6296461

2530 Holtrock St
Kissimmee, FL 34747

6

4

2

2,812 SqFt

Pool

0.28 Acres

216 Days

$689,000

MLS#MFRO6353180

2693 Manesty Ln
Kissimmee, FL 34747

6

4

2

3,548 SqFt

Pool

0.14 Acres

13 Days

Reduced

$659,999

$669,999

MLS#MFRS5128304

7751 Tosteth St
Kissimmee, FL 34747

6

4

2

3,612 SqFt

Pool

0.2 Acres

166 Days

$649,800

MLS#MFRO6358850

7730 Teascone Blvd
Kissimmee, FL 34747

6

4

2

3,093 SqFt

Pool

0.14 Acres

6 Days

$639,000

MLS#MFRO6325816

7763 Tosteth St
Kissimmee, FL 34747

6

4

2

3,568 SqFt

Pool

0.14 Acres

129 Days

Reduced

$623,000

$650,000

MLS#MFRS5118985

2615 Pawnall St
Kissimmee, FL 34747

5

5

2

3,160 SqFt

Pool

0.16 Acres

300 Days

54 Active Listings in Windsor Hills