Overlook Estates

Overlook Estates is a gated community of single family homes, and townhomes in Winter Haven, Florida, with a range of options priced between $349,000 and $499,900. There are currently a total of 3 homes for sale in Overlook Estates. The smallest Overlook Estates home presently available is a three bedroom two bathroom residence that is 2,585 square feet (1,860SF Under Air living space), and the largest of the Overlook Estates homes currently on the market has four beds and two baths and is a 4,216 square foot (2,850SF Under Air) residence.

Property management fees in Polk County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Overlook Estates are $550 and $550 for a townhome. This fee includes grounds maintenance, maintaining the community roads, and real estate taxes for common areas. Please check the individual listing pages for the exact homeowners association fees for a particular Overlook Estates home.

The Overlook Estates HOA rules do allow homeowners to have pets although there are certain breed restrictions. There is a limitation on pet size. Dogs and cats are allowed.

There are four commercial airports that serve Overlook Estates - Lakeland Linder International (LAL), which is twenty miles away; Kissimmee Gateway (ISM), which is twenty five miles away; Orlando International (MCO), which is 37 miles away, and Orlando Executive (ORL), which is 43 miles away from Overlook Estates.

Overlook Estates real estate activity on the Winter Haven MLS during the past year (as of March 2026) reflects two homes changing hands, with an average asking price of $474,950 and an average selling price of $455,000. This represents a healthy list-to-sell price ratio of 96% and $141 per square foot. During this period, Overlook Estates homes for sale have taken an average of just 15 days to sell.

In addition, there are numerous other communities in Winter Haven to choose from, or you may browse all available Winter Haven Real Estate, including some new construction opportunities. Homes for sale in Overlook Estates are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Overlook 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.

Overlook Estates Homes For Sale

Reduced

$445,000

$462,900

MLS#MFRL4958092

240 Santa Rosa Dr
Winter Haven, FL 33884

4

3

2

4,216 SqFt

Pool

0.28 Acres

75 Days

Reduced

$399,900

$425,000

MLS#MFRS5139735

716 Santa Maria Dr
Winter Haven, FL 33884

3

2

2

2,938 SqFt

Pool

Water Front

0.33 Acres

94 Days

Reduced

$349,000

$365,000

MLS#MFRP4937320

720 Santa Maria Dr
Winter Haven, FL 33884

3

2

2

2,964 SqFt

0.59 Acres

52 Days

3 Active Listings in Overlook Estates