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Winter Haven, FL Homes for Sale — Page 30 | 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 775 Listings

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24 of 775 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced25Active
$445,000
4 bd · 3 ba · 2,850 sqft
240 Santa Rosa Dr, Winter Haven, FL
Brian Surrency · LIVE FLORIDA REALTY
Price Reduced62Active
$284,500
3 bd · 2 ba · 2,109 sqft
2925 Dayton Dr, Winter Haven, FL
Eileen Belanger · CENTURY 21 MYERS REALTY LAKE WALES
27Active
$288,900
4 bd · 2 ba · 1,665 sqft
4160 Giorgio Dr, Winter Haven, FL
Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

Price Reduced16Active
$112,000
2 bd · 2 ba · 851 sqft
831 Orchid Springs Dr ##831, Winter Haven, FL
Steven Perkins · CLARK REALTY LLC
Price Reduced54Active
$335,000
2 bd · 2 ba · 1,677 sqft
5197 Pebble Beach Blvd, Winter Haven, FL
Lori Raath · LAKE ASHTON REALTY INC.
Price Reduced32Active
$269,000
3 bd · 2 ba · 1,688 sqft
440 Kensington View Dr, Winter Haven, FL
Michael Huculak · PREFERRED RE BROKERS III
Price Reduced19Active
$84,900
2 bd · 2 ba · 1,152 sqft
4165 Rolling Oaks Dr, Winter Haven, FL
Reta Stead · SOUTHERN BELLE REALTY
Price Reduced40Active
$265,000
3 bd · 1 ba · 1,602 sqft
3022 Hickory St NW, Winter Haven, FL
Ashlee Morrell · THE URBAN GROUP, INC.
Price Reduced64Active
$106,000
2 bd · 2 ba · 1,216 sqft
4251 Cedarwood St, Winter Haven, FL
KATHY Devor · COLDWELL BANKER REALTY
Price Reduced41Active
$340,000
5 bd · 3 ba · 2,274 sqft
271 Inman Blvd, Winter Haven, FL
Isabelle Maye · BHHS FLORIDA PROPERTIES GROUP
21Active
$239,500
3 bd · 2 ba · 1,560 sqft
109 Rebecca Dr NE, Winter Haven, FL
David Small · KELLER WILLIAMS REALTY SMART 1
Price Reduced52Active
$410,000
4 bd · 3 ba · 2,495 sqft
108 Lake Region Blvd N, Winter Haven, FL
Michael Stone · THE STONES REAL ESTATE FIRM
Price Reduced19Active
$237,490
3 bd · 2 ba · 1,516 sqft
3349 Costello Cir, Winter Haven, FL
Marian Benson · VALOR REALTY SERVICES LLC
Price Reduced50Active
$259,900
4 bd · 3 ba · 2,159 sqft
511 Marcia Loop, Winter Haven, FL
Deanna Stone · THE STONES REAL ESTATE FIRM
Price Reduced32Active
$399,999
5 bd · 4 ba · 3,040 sqft
205 Tifton St, Winter Haven, FL
Paul Shearn · FUTURE HOME REALTY INC
43Active
$350,000
3 bd · 2 ba · 2,431 sqft
1218 37th St NW, Winter Haven, FL
Prudy Cole · CENTURY 21 BE3
Open house Wed, Oct 7 · 12:00 PM16Active
$308,950
3 bd · 2 ba · 1,700 sqft
5351 Mickey Ave, Winter Haven, FL
Stephanie Morales, LLC · AXEN REALTY, LLC
Price Reduced22Active
$180,000
2 bd · 2 ba · 1,439 sqft
2270 Firestone Pl, Winter Haven, FL
Darin Dobson · COMPASS FLORIDA LLC
Price Reduced24Active
$214,000
3 bd · 2 ba · 1,419 sqft
2739 Rutledge Ct, Winter Haven, FL
David Small · KELLER WILLIAMS REALTY SMART 1
Price Reduced43Active
$287,500
4 bd · 2 ba · 1,836 sqft
1864 Emily Dr, Winter Haven, FL
Octavia Cheveresan · RE/MAX ACTION FIRST OF FLORIDA
Price Reduced46Active
$158,000
2 bd · 2 ba · 1,248 sqft
6315 Grove Pointe Dr SE, Winter Haven, FL
Anita Lowe · LOCKHART & ASSOCIATES INC
1Active
$285,000
3 bd · 2 ba · 1,265 sqft
200 Black Skimmer Ln, Winter Haven, FL
Linda Andre · COLDWELL BANKER REALTY
Price Reduced31Active
$104,900
2 bd · 2 ba · 1,056 sqft
4179 Rolling Oaks Dr, Winter Haven, FL
Reta Stead · SOUTHERN BELLE REALTY
Price Reduced87Active
$349,999
3 bd · 3 ba · 2,263 sqft
239 Golf Aire Blvd, Winter Haven, FL
Christina Ashley · DALTON WADE INC

1…29 30 31…33

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.

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.

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)

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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)