Rolling Hills Estates

Rolling Hills Estates is a community of single family homes, and townhomes in Kissimmee, Florida, with a range of options priced between $410,000 and $589,000. There are currently a total of 7 homes for sale in Rolling Hills Estates. The smallest Rolling Hills Estates home presently available is a four bedroom two bathroom residence that is 1,662 square feet (1,643SF Under Air living space), and the largest of the Rolling Hills Estates homes currently on the market has six beds and four baths and is a 3,500 square foot (2,857SF 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 Rolling Hills Estates range from $60 to $635 and $354 for a townhome. This fee includes grounds maintenance, real estate taxes for common areas, and trash removal. Please check the individual listing pages for the exact homeowners association fees for a particular Rolling Hills Estates home.

The Rolling Hills Estates HOA rules do allow homeowners to have pets although there are certain breed restrictions. Dogs and cats are allowed.

There are four commercial airports that serve Rolling Hills Estates - Kissimmee Gateway (ISM), which is ten miles away; Orlando International (MCO), which is nineteen miles away; Orlando Executive (ORL), which is twenty three miles away, and Lakeland Linder International (LAL), which is 34 miles away from Rolling Hills Estates.

Rolling Hills Estates real estate activity on the Kissimmee MLS during the past year (as of September 2025) reflects twelve homes changing hands, with an average asking price of $485,135 and an average selling price of $472,108. This represents a healthy list-to-sell price ratio of 97% and $177 per square foot. During this period, Rolling Hills Estates homes for sale have taken an average of 87 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 Rolling Hills Estates are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Rolling Hills Estates 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.

Rolling Hills Estates Homes For Sale

Reduced

$559,000

$610,000

MLS#MFRS5108996

7978 Magnolia Bend Ct
Kissimmee, FL 34747

5

5

3,500 SqFt

Pool

0.17 Acres

429 Days

Reduced

$549,950

$575,000

MLS#MFRS5129692

7912 Golden Pond Cir
Kissimmee, FL 34747

6

5

2

2,677 SqFt

Pool

0.24 Acres

97 Days

Reduced

$549,950

$624,950

MLS#MFRS5106283

7953 Heritage Entrance Blvd
Kissimmee, FL 34747

5

4

2

3,223 SqFt

Pool

0.17 Acres

480 Days

Reduced

$499,900

$499,999

MLS#MFRS5130175

7985 Magnolia Bend Ct
Kissimmee, FL 34747

4

3

2

2,341 SqFt

Pool

0.17 Acres

73 Days

New Construction

Reduced

$477,900

$499,000

MLS#MFRO6301247

8001 Formosa Valley
Kissimmee, FL 34747

4

5

2,314 SqFt

Pool

0.04 Acres

161 Days

$475,000

MLS#MFRO6268242

7947 Golden Pond Cir
Kissimmee, FL 34747

4

2

2

2,042 SqFt

Pool

0.16 Acres

270 Days

Under Contract

$410,000

$430,000

MLS#MFRS5123492

7925 Magnolia Bend Ct
Kissimmee, FL 34747

4

3

2

1,662 SqFt

Pool

0.15 Acres

187 Days

7 Active Listings in Rolling Hills Estates