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Winter Haven, FL Homes for Sale | 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 809 Listings

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24 of 809 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

New25Active
$698,000
11 bd · 5 ba · 4,465 sqft
2500 Avenue O NW, Winter Haven, FL
Brandy Waters · S & D REAL ESTATE SERVICE LLC
NewActive
$289,990
3 bd · 2 ba · 1,680 sqft
2747 San Marco Way, Winter Haven, FL
Charles Pennant · NEW HOME STAR FLORIDA LLC
NewActive
$330,000
3 bd · 2 ba · 1,718 sqft
2019 Kapree Ct, Winter Haven, FL
Crystal Jenkins · RE/MAX DOWNTOWN

New46Active
$275,000
3 bd · 2 ba · 1,400 sqft
2025 Marilyn Ave, Winter Haven, FL
Casandra Vann · KELLER WILLIAMS REALTY
NewActive
$369,000
3 bd · 2 ba · 2,123 sqft
218 Hartridge Hills Dr, Winter Haven, FL
Veronica Bard · LA ROSA REALTY PRESTIGE
New61Active
$409,900
3 bd · 3 ba · 1,867 sqft
427 W Lake Elbert Dr NE, Winter Haven, FL
Chrissi Jasso · ASSOCIATE REALTY
New6Active
$180,000
3 bd · 2 ba · 1,855 sqft
1328 Buckeye Trace Blvd, Winter Haven, FL
Jamie L Boone · Federa
New62Active
$244,900
2 bd · 2 ba · 1,595 sqft
2332 Salzburg Loop, Winter Haven, FL
Marti Sutton · CENTURY 21 WATSON & MYERS REALTY
New5Active
$210,000
4 bd · 2 ba · 2,836 sqft
165 Fish Hawk Dr, Winter Haven, FL
Jamie L Boone · Federa
57Active
$329,900
5 bd · 4 ba · 2,331 sqft
1364 Salisbury Dr, Winter Haven, FL
Vivian Ortiz · OAK AVENUE REAL ESTATE LLC
18Active
$278,000
3 bd · 2 ba · 1,844 sqft
516 McKenna Dr, Winter Haven, FL
Jesse Carriedo · REALTYCITY INC
New9Active
$180,000
2 bd · 2 ba · 826 sqft
2037 San Marcos Dr SE #325, Winter Haven, FL
Hoover Yap · PRIMESTATE REALTY, INC.
New37Active
$195,000
2 bd · 1 ba · 915 sqft
928 Sunshine Way SW, Winter Haven, FL
Michael Stone · THE STONES REAL ESTATE FIRM
New29Active
$205,000
2 bd · 1 ba · 915 sqft
926 Sunshine Way SW, Winter Haven, FL
Michael Stone · THE STONES REAL ESTATE FIRM
45Active
$290,000
4 bd · 3 ba · 2,526 sqft
5780 Lakeside Landings Blvd, Winter Haven, FL
Monica Hawkinson · LIVE FLORIDA REALTY
68Active
$339,975
3 bd · 2 ba · 2,066 sqft
384 Holly Ridge Rd, Winter Haven, FL
Vivian Ortiz · OAK AVENUE REAL ESTATE LLC
24Active
$710,000
3 bd · 3 ba · 3,292 sqft
9457 Waterford Oaks Dr, Winter Haven, FL
Amy Riggleman · SIGNATURE PROPERTIES OF CENTRAL FLORIDA LLC
65Active
$375,000
3 bd · 2 ba · 2,200 sqft
1501 N Lake Howard Dr, Winter Haven, FL
Kennedy Matthews · JULIE MATTHEWS GROUP LLC
6Active
$344,720
4 bd · 2 ba · 1,840 sqft
3937 Giorgio Dr, Winter Haven, FL
Bryan Sumner · MERITAGE HOMES OF FL REALTY
Open house Sat, Nov 7 · 11:00 AM21Active
$250,000
3 bd · 2 ba · 1,432 sqft
1688 Teagan Ln, Winter Haven, FL
Luana Oliveira · ORANGE SLICE PROPERTIES
44Active
$140,000
1 bd · 1 ba · 714 sqft
235 6th St NW #507, Winter Haven, FL
Blake Denz · KELLER WILLIAMS REALTY
36Active
$308,000
3 bd · 3 ba · 1,933 sqft
1140 Tyler Loop, Winter Haven, FL
Darcy Aguilera · REALTY OF AMERICA
19Active
$197,000
2 bd · 2 ba · 1,369 sqft
1643 Linz Ct, Winter Haven, FL
Jesse Carriedo · REALTYCITY INC
24Active
$399,000
3 bd · 2 ba · 1,734 sqft
1151 Carefree Cove Dr, Winter Haven, FL
Jonathan Minerick · HOMECOIN.COM

1 2…34

Listing data & MLS disclosures

Georgia MLS: The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of GAMLS. All real estate listings are marked with the GAMLS Broker Reciprocity thumbnail logo and detailed information about them includes the name of the listing brokers. The broker providing these data believes them to be correct, but advises interested parties to confirm them before relying on them in a purchase decision. Copyright © 2026 GAMLS. All rights reserved.
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

October 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 126 sales · as of Oct 30, 2026

Homes that sold · County records, as of Oct 15, 2026

Median sale price: $300,000$242,000–$1,281,875 typical range
Price per sq. ft.: $167
Sales: 146
Paid in cash: 44.5%

Homes on the market · MLS, as of Oct 18, 2026–Oct 30, 2026

Median list price: $295,000
Homes for sale: 713
Median days on market: 52 days

Price trend · Assessor repeat sales, as of Oct 31, 2026

Year-over-year: 1.4%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 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

Georgia MLS: The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program of GAMLS. All real estate listings are marked with the GAMLS Broker Reciprocity thumbnail logo and detailed information about them includes the name of the listing brokers. The broker providing these data believes them to be correct, but advises interested parties to confirm them before relying on them in a purchase decision. Copyright © 2026 GAMLS. All rights reserved.
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

Call Thomas

Homes with a Pool

Waterfront Homes

Foreclosures & Short Sales

55+ Community Homes

Nearby areas

ZIP codes

34747 (1,258)
34746 (856)
33837 (760)
33896 (586)
33844 (570)
34759 (496)
33897 (437)
33884 (360)

Cities

Kissimmee (3,048)
Davenport (1,749)
Lakeland (1,165)
Haines City (558)
Lake Wales (423)
Auburndale (242)
St. Cloud (200)
Bartow (149)

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

October 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 126 sales · as of Oct 30, 2026

Homes that sold · County records, as of Oct 15, 2026

Median sale price: $300,000$242,000–$1,281,875 typical range
Price per sq. ft.: $167
Sales: 146
Paid in cash: 44.5%

Homes on the market · MLS, as of Oct 18, 2026–Oct 30, 2026

Median list price: $295,000
Homes for sale: 713
Median days on market: 52 days

Price trend · Assessor repeat sales, as of Oct 31, 2026

Year-over-year: 1.4%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

Median home size: 1,632 sq. ft.

Nearby areas

ZIP codes

34747 (1,258)
34746 (856)
33837 (760)
33896 (586)
33844 (570)
34759 (496)
33897 (437)
33884 (360)

Cities

Kissimmee (3,048)
Davenport (1,749)
Lakeland (1,165)
Haines City (558)
Lake Wales (423)
Auburndale (242)
St. Cloud (200)
Bartow (149)