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Buy

Start here

Homes for sale by state
Home buying tips
Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

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Rentals
Commercial

801 listings

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Compare selling options
Get an instant cash offer
Buy before you sell

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3 beds New construction With a pool

801 listings

Homes for Sale in Winter Haven, FL

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24 of 801 Listings

Map

24 of 801 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

New10

Active

$210,000

3 bd · 2 ba · 1,160 sqft

922 Martin Luther King Blvd NE, Winter Haven, FL

Jairo Serrano PA · AROD PARTNERS REALTY

New28Active

$299,900

3 bd · 2 ba · 1,714 sqft

168 Waterside Cir, Winter Haven, FL

Steven Koleno · BEYCOME OF FLORIDA LLC

36Active

$129,900

2 bd · 2 ba · 828 sqft

6066 SE Southern Oaks Dr, Winter Haven, FL

Ryan Odenweller, LLC · RE/MAX HERITAGE PROFESSIONALS

36Active

$254,900

3 bd · 2 ba · 1,249 sqft

3420 Cove Ct E, Winter Haven, FL

Tina Winter · LA ROSA REALTY PRESTIGE

10Active

$270,000

3 bd · 2 ba · 1,820 sqft

1358 Buckeye Trace Blvd, Winter Haven, FL

Don Jerue · KELLER WILLIAMS REALTY SMART 1

38Active

$295,000

4 bd · 2 ba · 1,876 sqft

4956 Jackson St, Winter Haven, FL

Anthony Medina · KELLER WILLIAMS REALTY SMART 1

65Active

$359,900

2 bd · 2 ba · 1,871 sqft

4043 Bedford Ave, Winter Haven, FL

Deanna Stone · THE STONES REAL ESTATE FIRM

7Active

$275,000

4 bd · 2 ba · 1,607 sqft

3944 Giorgio Dr, Winter Haven, FL

Bryan Sumner · MERITAGE HOMES OF FL REALTY

25Active

$269,900

3 bd · 2 ba · 1,372 sqft

503 William Ave, Winter Haven, FL

Miriam Adame · OAKSTRAND REALTY

44Active

$134,990

1 bd · 1 ba · 481 sqft

7060 Fairview Village Cir, Winter Haven, FL

AJ Alvarez · LPT REALTY, LLC

23Active

$170,000

2 bd · 2 ba · 1,093 sqft

395 San Jose Dr, Winter Haven, FL

Chrissi Jasso · ASSOCIATE REALTY

21Active

$295,000

3 bd · 2 ba · 1,292 sqft

1354 Haines Dr, Winter Haven, FL

Aizat Tuleeva · LPT REALTY, LLC

27Active

$211,000

2 bd · 2 ba · 1,017 sqft

306 Eagle Pond Drive #306, Winter Haven, FL

Amy Sullivan · FLORIDA HOME REALTY GROUP, LLC

42Active

$285,000

3 bd · 2 ba · 1,432 sqft

668 Reggie Rd, Winter Haven, FL

Kenny Medina · LPT REALTY, LLC

36Active

$325,000

3 bd · 2 ba · 1,690 sqft

2021 Canton Park Dr, Winter Haven, FL

Maria Olmos, LLC · LA ROSA REALTY ORLANDO LLC

71Active

$165,500

2 bd · 2 ba · 1,224 sqft

6733 Kensington Dr NE, Winter Haven, FL

Cynthia Cole · FLORIDA REALTY MARKETPLACE

42Active

$380,000

3 bd · 2 ba · 1,020 sqft

417 Avenue G SE, Winter Haven, FL

Arlin De Leon, PA · LA ROSA REALTY KISSIMMEE

34Active

$299,999

4 bd · 3 ba · 1,933 sqft

997 Harold Pass, Winter Haven, FL

Andrea Heck · KELLER WILLIAMS TAMPA CENTRAL

39Active

$459,000

4 bd · 2 ba · 2,069 sqft

114 Belmont Dr, Winter Haven, FL

Mark Bouchard · MLB FREEDOM DESTINATIONS

33Active

$225,000

3 bd · 2 ba · 1,245 sqft

125 Whittier Ln, Winter Haven, FL

Lori Roberts · GOLD HEART REALTY LLC

32Active

$369,900

4 bd · 3 ba · 3,020 sqft

829 Sun Ridge Village Dr, Winter Haven, FL

Robert Salmons · ENTERA REALTY LLC

64Active

$249,900

3 bd · 2 ba · 1,140 sqft

240 Westwood Ave, Winter Haven, FL

Nicole Silva · RE/MAX COLLECTIVE

Open house Mon, Oct 19 · 9:00 AM22Active

$300,000

3 bd · 3 ba · 1,867 sqft

222 Cloverdale Rd, Winter Haven, FL

Karen Albright · OPENDOOR BROKERAGE LLC

87Active

$1,295,000

3 bd · 3 ba · 2,375 sqft

1921 Manor Cir SE, Winter Haven, FL

Dee Norris · NEXTHOME NORRIS & COMPANY REAL

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

September 2026 · This period is still settling

Selling at 99.9% of asking price

Sales here are closing essentially at asking. MLS · 138 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 30, 2026

Median sale price: $270,000$195,000–$332,030 typical range
Price per sq. ft.: $159
Sales: 200
Paid in cash: 38.0%

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

Median list price: $294,400

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

Explore Winter Haven homes

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Single-Family Homes
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By feature

New Construction Homes

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.

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 (1,216)
34746 (840)
33837 (757)
33896 (572)
33844 (568)
34759 (486)
33897 (442)
33884 (350)

Cities

Kissimmee (2,966)
Davenport (1,742)
Lakeland (1,172)
Haines City (564)
Lake Wales (415)

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Nearby areas

ZIP codes

34747 (1,216)
34746 (840)
33837 (757)
33896 (572)
33844 (568)
34759 (486)
33897 (442)
33884 (350)

Cities

Kissimmee (2,966)
Davenport (1,742)
Lakeland (1,172)
Haines City (564)
Lake Wales (415)

Auburndale (245)

Orlando (148)

Lake Alfred (144)

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 99.9% of asking price

Sales here are closing essentially at asking. MLS · 138 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 30, 2026

Median sale price: $270,000$195,000–$332,030 typical range
Price per sq. ft.: $159
Sales: 200
Paid in cash: 38.0%

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

42 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 Homes for Sale | Realty.com