Whispering Trails Winter Haven

Whispering Trails is a community of single family homes in Winter Haven, Florida, with a range of options priced between $215,500 and $370,000. There are currently a total of 5 homes for sale in Whispering Trails. The smallest Whispering Trails home presently available is a three bedroom two bathroom residence that is 1,148 square feet, and the largest of the Whispering Trails homes currently on the market has four beds and two baths and is a 2,603 square foot (2,203SF 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 Whispering Trails range from $233 to $286. This fee includes grounds maintenance, building maintenance, maintaining the community roads, the community pool, real estate taxes for common areas, property insurance, electric, trash removal, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Whispering Trails home.

Whispering Trails amenities include a clubhouse, and swimming pool. There is also walking or jogging trails.

The Whispering Trails 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 Whispering Trails - Lakeland Linder International (LAL), which is twenty two miles away; Kissimmee Gateway (ISM), which is twenty three miles away; Orlando International (MCO), which is 36 miles away, and Orlando Executive (ORL), which is 42 miles away from Whispering Trails.

Whispering Trails real estate activity on the Winter Haven MLS during the past year (as of March 2026) reflects eleven homes changing hands, with an average asking price of $253,718 and an average selling price of $252,582. This represents a healthy list-to-sell price ratio of 100% and $139 per square foot. During this period, Whispering Trails homes for sale have taken an average of 161 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 Whispering Trails are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Whispering Trails 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.

Whispering Trails Homes For Sale

$370,000

MLS#MFRO6386254

3142 Whispering Trails St
Winter Haven, FL 33884

4

3

2

2,603 SqFt

0.15 Acres

7 Days

Under Contract

$239,900

$254,500

MLS#MFRO6336904

2033 Whispering Trails Blvd
Winter Haven, FL 33884

3

2

2

1,756 SqFt

0.12 Acres

192 Days

$230,000

MLS#MFRS5138803

2893 Whispering Trails Dr
Winter Haven, FL 33884

3

2

2

1,774 SqFt

0.11 Acres

108 Days

$230,000

MLS#MFRP4937721

2036 Whispering Trails Blvd
Winter Haven, FL 33884

3

2

1

1,148 SqFt

0.17 Acres

8 Days

Under Contract

$215,500

$230,000

MLS#MFRS5114687

2796 Whispering Trails Dr
Winter Haven, FL 33884

3

2

2

1,558 SqFt

0.15 Acres

493 Days

You may also be interested in Whispering Trails in Jupiter or Whispering Trails in Coconut Creek.

5 Active Listings in Whispering Trails