Winterset

Winterset is a gated community of single family homes, condos, and townhomes in Winter Haven, Florida, with a range of options priced between $158,000 and $425,000. There are currently a total of 14 homes for sale in Winterset. The smallest Winterset home presently available is a three bedroom two bathroom residence that is 930 square feet (781SF Under Air living space), and the largest of the Winterset homes currently on the market has four beds and two baths and is a 2,900 square foot (2,257SF 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 Winterset range from $44 to $230 and range from $369 to $475 for a Winterset condo and $217 for a townhome. This fee includes common area maintenance, grounds maintenance, building maintenance, maintaining the community roads, the community pool, and security. Also included is a 24-hour guard, real estate taxes for common areas, property insurance, electric, trash removal, pest control, Cable TV, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Winterset home.

Winterset amenities include a clubhouse, swimming pool, spa / hot tub, and a state-of-the-art fitness center. Sports facilities include a championship golf course, tennis courts, pickleball courts, basketball court, and shuffleboard.

Boating enthusiasts will love the fact that the community has boat facilities including a boat ramp. There is also a community park, as well as a playground.

The Winterset 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 Winterset - Lakeland Linder International (LAL), which is twenty one miles away; Kissimmee Gateway (ISM), which is twenty six miles away; Orlando International (MCO), which is 38 miles away, and Orlando Executive (ORL), which is 44 miles away from Winterset.

Winterset real estate activity on the Winter Haven MLS during the past year (as of February 2026) reflects seventeen homes changing hands, with an average asking price of $255,599 and an average selling price of $246,230. This represents a healthy list-to-sell price ratio of 96% and $145 per square foot. During this period, Winterset homes for sale have taken an average of 102 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 Winterset are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Winterset 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.

Winterset Homes For Sale

Under Contract

$387,500

MLS#MFRP4936943

168 Morning Glory Cir
Winter Haven, FL 33884

3

2

2

2,415 SqFt

Pool

0.19 Acres

94 Days

Reduced

$315,000

$345,000

MLS#MFRP4932234

142 Morning Glory Cir
Winter Haven, FL 33884

3

2

2

2,562 SqFt

0.2 Acres

499 Days

$298,000

MLS#MFRO6198152

2586 San Marco Way
Winter Haven, FL 33884

4

2

2

2,214 SqFt

0.13 Acres

663 Days

New Construction

$289,900

MLS#MFRL4958217

100 Morning Glory Cir
Winter Haven, FL 33884

3

2

2

2,246 SqFt

0.2 Acres

36 Days

$289,000

MLS#MFRP4937101

110 Morning Glory Cir
Winter Haven, FL 33884

3

3

2

2,442 SqFt

0.17 Acres

81 Days

Under Contract

$269,900

$289,900

MLS#MFRP4935547

160 Morning Glory Cir
Winter Haven, FL 33884

3

2

2

2,064 SqFt

0.18 Acres

207 Days

$264,900

MLS#MFRP4937345

2202 Garden Lake Dr
Winter Haven, FL 33884

3

2

1

1,689 SqFt

0.09 Acres

49 Days

$235,000

MLS#MFRP4936867

714 Magnolia Pl #714
Winter Haven, FL 33884

2

2

1

1,330 Sq Ft

Water Front

0.02 Acres

107 Days

Reduced

$225,000

$235,000

MLS#MFRP4936544

802 Magnolia Pl
Winter Haven, FL 33884

2

2

1

1,302 Sq Ft

Water Front

132 Days

Reduced

$219,000

$240,000

MLS#MFRP4936224

715 Magnolia Pl
Winter Haven, FL 33884

2

2

1

1,330 Sq Ft

Water Front

154 Days

Under Contract

$209,900

$234,900

MLS#MFRL4954685

506 Sweet Bay Cir #506
Winter Haven, FL 33884

2

2

1,230 Sq Ft

0.02 Acres

205 Days

Reduced

$174,500

$189,500

MLS#MFRL4957843

7904 Waterview Way #7904
Winter Haven, FL 33884

2

2

930 Sq Ft

0.01 Acres

59 Days

14 Active Listings in Winterset