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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

795 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

795 listings

Homes for Sale in Winter Haven, FL

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24 of 795 Listings

Map

24 of 795 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

New42

Active

$285,000

3 bd · 2 ba · 1,432 sqft

668 Reggie Rd, Winter Haven, FL

Kenny Medina · LPT REALTY, LLC

New71Active

$165,500

2 bd · 2 ba · 1,176 sqft

6733 Kensington Dr NE, Winter Haven, FL

Cynthia Cole · FLORIDA REALTY MARKETPLACE

New42Active

$380,000

3 bd · 2 ba · 1,020 sqft

417 Avenue G SE, Winter Haven, FL

Arlin De Leon, PA · LA ROSA REALTY KISSIMMEE

New37Active

$459,000

4 bd · 2 ba · 2,069 sqft

114 Belmont Dr, Winter Haven, FL

Mark Bouchard · MLB FREEDOM DESTINATIONS

New64Active

$249,900

3 bd · 2 ba · 1,140 sqft

240 Westwood Ave, Winter Haven, FL

Nicole Silva · RE/MAX COLLECTIVE

New33Active

$225,000

3 bd · 2 ba · 1,245 sqft

125 Whittier Ln, Winter Haven, FL

Lori Roberts · GOLD HEART REALTY LLC

New87Active

$1,295,000

3 bd · 3 ba · 2,375 sqft

1921 Manor Cir SE, Winter Haven, FL

Dee Norris · NEXTHOME NORRIS & COMPANY REAL

New42Active

$289,000

4 bd · 2 ba · 1,851 sqft

138 Grove Branch Rd, Winter Haven, FL

Michael Stone · THE STONES REAL ESTATE FIRM

New1Active

$319,999

4 bd · 3 ba · 2,039 sqft

5365 San Pietro Dr, Winter Haven, FL

Michael Human · CASA FRESCA REALTY

New15Active

$294,990

5 bd · 3 ba · 2,112 sqft

6245 Botticella Blvd, Winter Haven, FL

Ben Goldstein · LENNAR REALTY

New22Active

$278,000

4 bd · 2 ba · 1,830 sqft

703 Avenue L SE, Winter Haven, FL

Sandra Wyhnanskyj, PA · OLYMPUS EXECUTIVE REALTY INC

New1Active

$364,745

5 bd · 3 ba · 2,470 sqft

1759 Vanilla St, Winter Haven, FL

Michael Human · CASA FRESCA REALTY

New1Active

$410,620

4 bd · 3 ba · 2,292 sqft

1764 Vanilla St, Winter Haven, FL

Michael Human · CASA FRESCA REALTY

New1Active

$333,090

4 bd · 3 ba · 2,039 sqft

1767 Vanilla St, Winter Haven, FL

Michael Human · CASA FRESCA REALTY

New31Active

$428,000

5 bd · 3 ba · 2,549 sqft

219 Terranova Blvd, Winter Haven, FL

Dwight Head · ALLSTATE REALTY SERVICES

72Active

$399,999

4 bd · 4 ba · 2,960 sqft

1217 Michelangelo Ln, Winter Haven, FL

Jocelyne Yanez · HOMESMART

New25Active

$515,000

5 bd · 3 ba · 2,685 sqft

2022 Kapree Ct, Winter Haven, FL

Jerome Baker · BAKER REAL ESTATE PRO. GR LLC

New48Active

$319,990

4 bd · 2 ba · 2,004 sqft

1127 Seedorf Dr, Winter Haven, FL

Juan Acevedo · FORTUNE INTERNATIONAL REALTY

New30Active

$337,500

3 bd · 2 ba · 2,034 sqft

1400 Avenue D NE, Winter Haven, FL

Glenda Pruitt · FLORIDA HOME CHOICE REALTY

New42Active

$279,900

3 bd · 2 ba · 1,556 sqft

420 Hillcrest Dr SE, Winter Haven, FL

Raymond Thomas · STAR BAY REALTY CORP.

New49Active

$327,700

4 bd · 2 ba · 1,830 sqft

221 Avenue P NW, Winter Haven, FL

Madeline Rivera · INNOVATION GROUP REALTY LLC

19Active

$380,000

4 bd · 3 ba · 2,509 sqft

1652 Lemon Ave, Winter Haven, FL

Danny Chandler, Jr · COLDWELL BANKER REALTY

New65Active

$559,900

4 bd · 3 ba · 2,775 sqft

7380 Bent Grass Dr, Winter Haven, FL

Twanna Dewdney · LA ROSA REALTY PRESTIGE

New21Active

$130,000

3 bd · 2 ba · 1,678 sqft

1406 Meadow Dr NE, Winter Haven, FL

Cesar Estrada, PA · EXP REALTY LLC

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 28, 2026

Median sale price: $270,000$196,000–$334,500 typical range
Price per sq. ft.: $160
Sales: 175
Paid in cash: 37.7%

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 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

By price

Homes Under $100K
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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 (841)
33837 (754)
33896 (573)
33844 (570)
34759 (484)
33897 (443)
33884 (347)

Cities

Kissimmee (2,966)
Davenport (1,742)
Lakeland (1,159)
Haines City (567)
Lake Wales (409)
Orlando (339)
Auburndale (252)
Winter Garden (203)

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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, FL Homes for Sale | Realty.com

Nearby areas

ZIP codes

34747 (1,216)
34746 (841)
33837 (754)
33896 (573)
33844 (570)
34759 (484)
33897 (443)
33884 (347)

Cities

Kissimmee (2,966)
Davenport (1,742)
Lakeland (1,159)
Haines City (567)
Lake Wales (409)
Orlando (339)
Auburndale (252)
Winter Garden (203)

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 28, 2026

Median sale price: $270,000$196,000–$334,500 typical range
Price per sq. ft.: $160
Sales: 175
Paid in cash: 37.7%

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.