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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 811 Listings

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24 of 811 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

New9Active
$180,000
2 bd · 2 ba · 826 sqft
2037 San Marcos Dr SE #325, Winter Haven, FL
Hoover Yap · PRIMESTATE REALTY, INC.
New18Active
$278,000
3 bd · 2 ba · 1,844 sqft
516 McKenna Dr, Winter Haven, FL
Jesse Carriedo · REALTYCITY INC
New57Active
$329,900
5 bd · 4 ba · 2,331 sqft
1364 Salisbury Dr, Winter Haven, FL
Vivian Ortiz · OAK AVENUE REAL ESTATE LLC

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
New45Active
$290,000
4 bd · 3 ba · 2,526 sqft
5780 Lakeside Landings Blvd, Winter Haven, FL
Monica Hawkinson · LIVE FLORIDA REALTY
New68Active
$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
New65Active
$375,000
3 bd · 2 ba · 2,200 sqft
1501 N Lake Howard Dr, Winter Haven, FL
Kennedy Matthews · JULIE MATTHEWS GROUP LLC
New6Active
$344,720
4 bd · 2 ba · 1,840 sqft
3937 Giorgio Dr, Winter Haven, FL
Bryan Sumner · MERITAGE HOMES OF FL REALTY
21Active
$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
New36Active
$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
72Active
$415,000
3 bd · 2 ba · 1,502 sqft
230 Shore Dr, Winter Haven, FL
Perry Kemp · LPT REALTY, LLC
32Active
$259,000
3 bd · 2 ba · 1,248 sqft
138 Saint Kitts Cir, Winter Haven, FL
Erik McGinnis · HOMEVEST REALTY
Open house Sun, Nov 8 · 11:00 AM48Active
$795,000
4 bd · 3 ba · 2,346 sqft
1010 Edgewater Dr, Winter Haven, FL
David Small · KELLER WILLIAMS REALTY SMART 1
38Active
$319,999
5 bd · 2 ba · 1,744 sqft
3429 Sherry Ave, Winter Haven, FL
Sandra Canales · LA ROSA REALTY PRESTIGE
21Active
$201,790
3 bd · 3 ba · 1,386 sqft
3115 Captain Jax Way, Winter Haven, FL
Ben Goldstein · LENNAR REALTY
41Active
$155,000
2 bd · 2 ba · 1,017 sqft
1606 Eagle Pond Dr, Winter Haven, FL
Lienyvette Grimaldo · MAZELG REALTY
Open house Sat, Nov 7 · 11:00 AM56Active
$375,000
4 bd · 3 ba · 2,200 sqft
6052 Kaley Dr, Winter Haven, FL
Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS
33Active
$182,900
2 bd · 1 ba · 728 sqft
3223 Avenue S NW, Winter Haven, FL
Carrie Sanchez · THE BARNETT GROUP, INC.
47Active
$975,000
4 bd · 3 ba · 2,825 sqft
4462 Emerald Palms Ln, Winter Haven, FL
Stephen Hachey · FLAT FEE MLS REALTY

1 2…34

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

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

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 (1,252)
34746 (852)
33837 (772)
33896 (585)
33844 (578)
34759 (493)
33897 (438)
33884 (365)

Cities

Kissimmee (3,043)
Davenport (1,760)
Lakeland (1,185)
Haines City (566)
Lake Wales (422)
Orlando (348)
Auburndale (241)
Winter Garden (221)

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 (1,252)
34746 (852)
33837 (772)
33896 (585)
33844 (578)
34759 (493)
33897 (438)
33884 (365)

Cities

Kissimmee (3,043)
Davenport (1,760)
Lakeland (1,185)
Haines City (566)
Lake Wales (422)
Orlando (348)
Auburndale (241)
Winter Garden (221)