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Winter Haven, FL Homes for Sale — Page 26 | 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 Reduced17Active
$199,000
3 bd · 1 ba · 1,092 sqft
2710 Woodlawn Drive, Winter Haven, FL
Jeff Jones · MARK SPAIN REAL ESTATE
42Active
$115,000
2 bd · 2 ba · 1,368 sqft
113 Lake Hazel Dr, Winter Haven, FL
Chris Cain · MOSAIC SERVICES LLC
25Active
$269,990
3 bd · 2 ba · 1,302 sqft
5580 Taverna Loop, Winter Haven, FL
Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

48Active
$425,000
4 bd · 3 ba · 2,434 sqft
5009 Strada Drive, Winter Haven, FL
Florentino Beltran · KELLER WILLIAMS ADVANTAGE 2 REALTY
Price Reduced27Active
$209,000
2 bd · 1 ba · 900 sqft
434 Avenue D SE, Winter Haven, FL
Kellie Hicks · LOCKHART & ASSOCIATES INC
40Active
$310,000
4 bd · 3 ba · 1,933 sqft
1325 Diego Terrace, Winter Haven, FL
Maritza Saint Hilaire · COMPASS FLORIDA LLC
Price Reduced48Active
$289,990
4 bd · 2 ba · 1,625 sqft
296 Meredith Boulevard, Winter Haven, FL
Nancy Pruitt, PA · OLYMPUS EXECUTIVE REALTY INC
Price Reduced27Active
$209,000
2 bd · 1 ba · 900 sqft
434 Avenue D SE, Winter Haven, FL
Kellie Hicks · LOCKHART & ASSOCIATES INC
15Active
$580,000
4 bd · 3 ba · 2,050 sqft
915 Hillside Ct S, Winter Haven, FL
Karen Myers · UNITED REALTY GROUP INC
15Active
$580,000
4 bd · 3 ba · 2,050 sqft
915 Hillside Court S, Winter Haven, FL
Karen Myers · UNITED REALTY GROUP INC
Price Reduced4Active
$336,900
3 bd · 2 ba · 2,005 sqft
544 Ituna Cir, Winter Haven, FL
George Lindsey, III · CAMBRIDGE REALTY OF CENTRAL FL
33Active
$129,500
2 bd · 1 ba · 826 sqft
1100 Martinique Drive 106, Winter Haven, FL
David Small · KELLER WILLIAMS REALTY SMART 1
25Active
$292,900
3 bd · 2 ba · 1,302 sqft
3328 White Indigo Rd, Winter Haven, FL
Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC
62Active
$110,000
2 bd · 2 ba · 1,104 sqft
4807 Plumwood Street, Winter Haven, FL
KATHY Devor · COLDWELL BANKER REALTY
Price Reduced35Active
$298,900
3 bd · 2 ba · 1,930 sqft
2523 Avenue E SW, Winter Haven, FL
Gloria Johnpierre · SIVEN PREMIER REAL ESTATE
37Active
$376,990
4 bd · 3 ba · 2,308 sqft
1734 Hummingbird Rd, Winter Haven, FL
Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC
Price Reduced35Active
$298,900
3 bd · 2 ba · 1,930 sqft
2523 Avenue E SW, Winter Haven, FL
Gloria Johnpierre · SIVEN PREMIER REAL ESTATE
26Active
$185,000
2 bd · 1 ba · 934 sqft
790 Avenue Q SE, Winter Haven, FL
Amy Reynolds · LOCKHART & ASSOCIATES INC
32Active
$379,900
5 bd · 3 ba · 2,696 sqft
204 Inman Boulevard, Winter Haven, FL
Veronica Bard · LA ROSA REALTY PRESTIGE
14Active
$124,800
1 bd · 1 ba · 475 sqft
1103 Cypress Gardens Boulevard 13, Winter Haven, FL
Linda Andre · COLDWELL BANKER REALTY
25Active
$276,900
3 bd · 2 ba · 1,302 sqft
3328 White Indigo Road, Winter Haven, FL
Paul King · DR HORTON REALTY OF CENTRAL FLORIDA LLC
62Active
$110,000
2 bd · 2 ba · 1,104 sqft
4807 Plumwood St, Winter Haven, FL
KATHY Devor · COLDWELL BANKER REALTY
32Active
$379,900
5 bd · 3 ba · 2,696 sqft
204 Inman Blvd, Winter Haven, FL
Veronica Bard · LA ROSA REALTY PRESTIGE
14Active
$124,800
1 bd · 1 ba · 475 sqft
1103 Cypress Gardens Blvd #13, Winter Haven, FL
Linda Andre · COLDWELL BANKER REALTY

1…25 26 27…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)