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Winter Haven, FL Homes for Sale — Page 29 | Realty.com

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3 beds New construction With a pool

Homes for Sale in Winter Haven, FL

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24 of 1,549 Listings

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24 of 1,549 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced19Active
$230,000
3 bd · 2 ba · 1,426 sqft
297 Meadowbrook Blvd, Winter Haven, FL
Karina Alfonso · LPT REALTY, LLC
60Active
$399,900
4 bd · 3 ba · 1,894 sqft
4132 Martindale Loop, Winter Haven, FL
Mike Webb · TRADE WINDS REALTY
51Active
$149,900
2 bd · 2 ba · 1,190 sqft
700 Mirror Ter NW #511, Winter Haven, FL
David Small · KELLER WILLIAMS REALTY SMART 1

16Active
$380,000
5 bd · 3 ba · 2,696 sqft
210 Meadowbrook Boulevard, Winter Haven, FL
Lancey Lewis · HOMELIFE REALTY COASTAL PROPERTIES LLC
Price Reduced25Active
$249,000
3 bd · 2 ba · 1,258 sqft
392 Kensington View Dr, Winter Haven, FL
Dayna Grimmett · LIVE FLORIDA REALTY
Price Reduced56Active
$92,000
2 bd · 1 ba · 840 sqft
1700 6th St NW C24, Winter Haven, FL
Chrissi Jasso · ASSOCIATE REALTY
51Active
$149,900
2 bd · 2 ba · 1,190 sqft
700 Mirror Terrace NW 511, Winter Haven, FL
David Small · KELLER WILLIAMS REALTY SMART 1
Price Reduced25Active
$255,000
3 bd · 2 ba · 1,258 sqft
392 Kensington View Drive, Winter Haven, FL
Dayna Grimmett · LIVE FLORIDA REALTY
Price Reduced56Active
$92,000
2 bd · 1 ba · 840 sqft
1700 6th St NW #C24, Winter Haven, FL
Chrissi Jasso · ASSOCIATE REALTY
16Active
$380,000
5 bd · 3 ba · 2,696 sqft
210 Meadowbrook Blvd, Winter Haven, FL
Lancey Lewis · HOMELIFE REALTY COASTAL PROPERTIES LLC
Price Reduced83Active
$488,500
4 bd · 3 ba · 2,552 sqft
3158 Beauchamp Court, Winter Haven, FL
Kennedy Matthews · JULIE MATTHEWS GROUP LLC
32Active
$280,000
3 bd · 2 ba · 1,935 sqft
2470 Salzburg Loop, Winter Haven, FL
Ron Denney · LAND SOUTH REALTY, LLC
Price Reduced45Active
$274,989
3 bd · 2 ba · 1,507 sqft
2021 Oliver Pl, Winter Haven, FL
Ray Colon · TRUE FLORIDA REALTY LLC
45Active
$274,990
3 bd · 2 ba · 1,507 sqft
2021 Oliver Place, Winter Haven, FL
Ray Colon · TRUE FLORIDA REALTY LLC
Price Reduced83Active
$484,900
4 bd · 3 ba · 2,552 sqft
3158 Beauchamp Ct, Winter Haven, FL
Kennedy Matthews · JULIE MATTHEWS GROUP LLC
42Active
$349,900
3 bd · 2 ba · 2,035 sqft
1514 Hamlin Street, Winter Haven, FL
Scott Kline · KLINE REAL ESTATE SERVICES
42Active
$349,900
3 bd · 2 ba · 2,035 sqft
1514 Hamlin St, Winter Haven, FL
Scott Kline · KLINE REAL ESTATE SERVICES
32Active
$280,000
3 bd · 2 ba · 1,935 sqft
2470 Salzburg Loop, Winter Haven, FL
Ron Denney · LAND SOUTH REALTY, LLC
Price Reduced31Active
$94,900
1 bd · 1 ba · 1,078 sqft
200 el Camino Drive 306, Winter Haven, FL
Suzie Rudd · KELLER WILLIAMS REALTY SMART 1
31Active
$292,990
3 bd · 3 ba · 1,673 sqft
2759 Gladiola Rd, Winter Haven, FL
Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC
Price Reduced34Active
$278,000
4 bd · 2 ba · 1,680 sqft
1831 Carnostie Road, Winter Haven, FL
Natalie Citarelli · CITARELLI REALTY GROUP LLC
31Active
$263,990
3 bd · 3 ba · 1,673 sqft
2753 Gladiola Road, Winter Haven, FL
Paul King · DR HORTON REALTY OF CENTRAL FLORIDA LLC
31Active
$263,990
3 bd · 3 ba · 1,673 sqft
2759 Gladiola Road, Winter Haven, FL
Paul King · DR HORTON REALTY OF CENTRAL FLORIDA LLC
9Active
$109,900
3 bd · 2 ba · 860 sqft
3915 Avenue Q NW, Winter Haven, FL
Jorge Fanani · SOLARE REALTY LLC

1…28 29 30…65

Listing data & MLS disclosures

Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Winter Haven housing market

September 2026 · This period is still settling

Selling at 99.7% of asking price

Sales here are closing essentially at asking. MLS · 137 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 18, 2026

Median sale price: $270,000$207,500–$329,495 typical range
Price per sq. ft.: $161
Sales: 135
Paid in cash: 36.3%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $294,400
Homes for sale: 762
Median days on market: 48 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: -18.2%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Median home size: 1,632 sq. ft.

Winter Haven, FL community profile

Population: 58,351
Median income: $56,564
Housing units: 26,800
People per sq. mi.: 605.3
Area: 96.4 sq. mi.

Source: HJN community data

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Listing data & MLS disclosures

Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Foreclosures & Short Sales

55+ Community Homes

Nearby areas

ZIP codes

34747 (2,310)
34746 (1,665)
33837 (1,454)
33896 (1,129)
33844 (1,103)
34759 (925)
33897 (895)
33884 (687)

Cities

Kissimmee (2,913)
KISSIMMEE (2,856)
DAVENPORT (1,727)
Davenport (1,708)
Lakeland (1,157)
LAKELAND (1,121)
HAINES CITY (550)
Haines City (549)

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Winter Haven, FL community profile

Population: 58,351
Median income: $56,564
Housing units: 26,800
People per sq. mi.: 605.3
Area: 96.4 sq. mi.

Source: HJN community data

Winter Haven housing market

September 2026 · This period is still settling

Selling at 99.7% of asking price

Sales here are closing essentially at asking. MLS · 137 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 18, 2026

Median sale price: $270,000$207,500–$329,495 typical range
Price per sq. ft.: $161
Sales: 135
Paid in cash: 36.3%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $294,400
Homes for sale: 762
Median days on market: 48 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: -18.2%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Median home size: 1,632 sq. ft.

Nearby areas

ZIP codes

34747 (2,310)
34746 (1,665)
33837 (1,454)
33896 (1,129)
33844 (1,103)
34759 (925)
33897 (895)
33884 (687)

Cities

Kissimmee (2,913)
KISSIMMEE (2,856)
DAVENPORT (1,727)
Davenport (1,708)
Lakeland (1,157)
LAKELAND (1,121)
HAINES CITY (550)
Haines City (549)