Winter Haven Real Estate

Some of the best housing options in Polk County are in the Winter Haven Real Estate market, with a variety of single family homes for sale priced between $30 thousand and as high as $1,950,000 two to nine bedroom homes that range in size from 696 to 39,733 square feet. Options for Condos in Winter Haven range from $59,900 for an apartment with one bedroom and one bathroom to three bedrooms and three bathroom luxury condominiums that sell for up to $269,900. Suppose a Townhome for sale in Winter Haven is what you are looking for, a two-bedroom, one bathroom 972 square foot villa or a three-bed, three-bath home as large as 2,743 sq ft ranging in price from $124,000 to $405,000.

We have detailed information regarding 128 communities in Winter Haven, including 95 non-gated communities of single family homes, two condo buildings, 29 gated communities, one country club, and one retirement community including some new construction opportunities and open houses. Winter Haven real estate activity on the MLS indicates 1,051 properties are currently on the market (as of February 21st, 2026). Whether relocating to Winter Haven from another state or upsizing or downsizing, whichever of the many homes for sale in Winter Haven and the entire Central Florida region you choose, our professional Realtors in Winter Haven Florida can guide you through the home-buying process.

Winter Haven Homes For Sale

$1.95 Million

MLS#MFRL4958559

13 Bogey Dr
Winter Haven, FL 33881

4

4

2

5,671 SqFt

Pool

Water Front

10.98 Acres

39 Days

$1,799,999

Gaines Cove

3826 Gaines Ct
Winter Haven, FL 33884

6

6

4

7,395 SqFt

Pool

Water Front

1.86 Acres

21 Days

Under Contract

$1.499 Million

$1,575,000

Gaines Cove

3824 Gaines Dr
Winter Haven, FL 33884

7

7

2

8,705 SqFt

Pool

Water Front

0.64 Acres

130 Days

Under Contract

$1,450,000

MLS#MFRL4958470

3800 Gerber Dairy Rd
Winter Haven, FL 33880

3

2

2

3,510 SqFt

Pool

30.36 Acres

32 Days

$1,200,000

MLS#MFRL4958708

209 Frenchmans Creek Way
Winter Haven, FL 33884

5

4

2

7,619 SqFt

Pool

2.62 Acres

32 Days

Reduced

$1,199,000

$1,300,000

Cypress Point

1123 Cypress Pt W
Winter Haven, FL 33884

3

4

2

3,927 SqFt

Pool

Water Front

0.72 Acres

216 Days

$1,195,000

MLS#MFRP4934742

250 Brigham Rd Nw
Winter Haven, FL 33881

5

6

4

5,235 SqFt

Pool

Water Front

1.3 Acres

289 Days

$1,150,000

MLS#MFRP4919411

1200 W Lake Otis Dr Se
Winter Haven, FL 33880

6

6

6,500 SqFt

Pool

Water Front

0.74 Acres

1460 Days

$1 Million

MLS#MFRB4901530

103 Eagle Lake Loop Rd
Winter Haven, FL 33884

2

1

1,128 SqFt

0.93 Acres

670 Days

Under Contract

$919,000

MLS#MFRL4957283

157 Lake Roy Dr
Winter Haven, FL 33884

5

5

4

4,558 SqFt

Pool

Water Front

0.65 Acres

98 Days

Reduced

$899,900

$975,000

MLS#MFRP4935447

200 Island Way
Winter Haven, FL 33884

4

4

2

5,351 SqFt

Pool

Water Front

1.05 Acres

229 Days

$880,000

MLS#MFRL4957757

906 Lake Jessie Dr
Winter Haven, FL 33881

9

7

2

6,551 SqFt

Water Front

0.47 Acres

77 Days

1,051 Active Listings in Winter Haven, FL

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Living in Winter Haven affords you easy access to nearby golf courses, fine dining, entertainment venues and various other amenities and conveniences in the city of Winter Haven. Local and interstate highways provide an easy transition to nearby cities such as Eagle Lake, Lake Alfred, Dundee, Auburndale, Davenport, Polk City, Haines City, Poinciana, Kissimmee, Lakeland, Bartow, and Lake Wales.

Boating and watersports are integral to the Central Florida lifestyle, offering year-round access to an abundance of lakes, vibrant marine life, and a culture centered around outdoor leisure and recreation. Winter Haven real estate prices are directly correlated to it's proximity to these amenities.

Additionally, four local airports are easily accessible - Lakeland Linder International (LAL), Kissimmee Gateway (ISM) in Orlando, Orlando International (MCO), and Orlando Executive (ORL). Finally, for private air travel, you may utilize Winter Haven Regional (GIF), and Bartow Executive (BOW).

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.