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 $264,000 and $750,000. There are currently a total of 50 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 $466 to $2,050 and range from $679 to $1,120 for a Windsor Hills condo and $505 to $1,624 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 February 2026) reflects 83 homes changing hands, with an average asking price of $492,574 and an average selling price of $477,709. This represents a healthy list-to-sell price ratio of 97% and $224 per square foot. During this period, Windsor Hills homes for sale have taken an average of 94 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

$750,000

MLS#MFRO6368643

7772 Basnett Cir
Kissimmee, FL 34747

6

4

2

3,568 SqFt

Pool

0.14 Acres

59 Days

Under Contract

$749,000

$849,000

MLS#MFRO6365819

2607 Daulby St
Kissimmee, FL 34747

6

4

2

3,548 SqFt

Pool

0.15 Acres

67 Days

$740,000

MLS#MFRO6298445

7790 Teascone Blvd
Kissimmee, FL 34747

5

5

2

2,297 SqFt

Pool

0.32 Acres

307 Days

$718,000

MLS#MFRO6373708

7793 Basnett Cir
Kissimmee, FL 34747

6

4

2

3,568 SqFt

Pool

0.19 Acres

33 Days

$695,000

MLS#MFRO6364292

7757 Basnett Cir
Kissimmee, FL 34747

6

4

2

2,469 SqFt

Pool

0.16 Acres

76 Days

Under Contract

$685,000

MLS#MFRS5142681

2596 Archfeld Blvd
Kissimmee, FL 34747

6

4

2

3,612 SqFt

Pool

0.15 Acres

19 Days

$675,000

MLS#MFRO6377645

7751 Basnett Cir
Kissimmee, FL 34747

6

4

2

3,568 SqFt

Pool

0.16 Acres

19 Days

Under Contract

$665,000

$700,000

MLS#MFRO6367961

2619 Daulby St
Kissimmee, FL 34747

5

5

2

2,342 SqFt

Pool

0.16 Acres

61 Days

$659,000

MLS#MFRO6371195

7788 Basnett Cir
Kissimmee, FL 34747

5

5

2

2,342 SqFt

Pool

0.19 Acres

37 Days

Reduced

$655,000

$689,000

MLS#MFRO6353180

2693 Manesty Ln
Kissimmee, FL 34747

6

4

2

3,548 SqFt

Pool

0.14 Acres

104 Days

$650,000

MLS#MFRO6376480

7761 Tosteth St
Kissimmee, FL 34747

6

4

2

3,612 SqFt

Pool

0.14 Acres

21 Days

Under Contract

$649,500

$649,800

MLS#MFRO6358850

7730 Teascone Blvd
Kissimmee, FL 34747

6

4

2

3,093 SqFt

Pool

0.14 Acres

97 Days

50 Active Listings in Windsor Hills