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3 beds New construction With a pool

Homes Under $400K in Winter Haven, FL

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24 of 699 Listings

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24 of 699 Listings

38Active

Homes Under $400K in Winter Haven, FL — Page 2

699 listings

Homes Under $400K in Winter Haven, FL

Hide Map

24 of 699 Listings

Map

Homes Under $400K in Winter Haven, FL

24 of 699 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

38Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$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

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

44Active

$134,990

1 bd · 1 ba · 481 sqft

7060 Fairview Village Cir, Winter Haven, FL

AJ Alvarez · DALTON WADE INC

23Active

$170,000

2 bd · 2 ba · 1,093 sqft

395 San Jose Dr, Winter Haven, FL

Chrissi Jasso · ASSOCIATE REALTY

25Active

$269,900

3 bd · 2 ba · 1,372 sqft

503 William Ave, Winter Haven, FL

Miriam Adame · OAKSTRAND REALTY

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

25Active

$295,000

3 bd · 2 ba · 1,292 sqft

1354 Haines Dr, Winter Haven, FL

Aizat Tuleeva · LPT REALTY, LLC

42Active

$285,000

3 bd · 2 ba · 1,432 sqft

668 Reggie Rd, Winter Haven, FL

Kenny Medina · LPT REALTY, LLC

56Active

$325,000

3 bd · 2 ba · 1,690 sqft

2021 Canton Park Dr, Winter Haven, FL

Maria Olmos, LLC · LA ROSA REALTY ORLANDO LLC

34Active

$299,999

4 bd · 3 ba · 1,933 sqft

997 Harold Pass, Winter Haven, FL

Andrea Heck · KELLER WILLIAMS TAMPA CENTRAL

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

71Active

$165,500

2 bd · 2 ba · 1,224 sqft

6733 Kensington Dr NE, Winter Haven, FL

Cynthia Cole · FLORIDA REALTY MARKETPLACE

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

33Active

$225,000

3 bd · 2 ba · 1,245 sqft

125 Whittier Ln, Winter Haven, FL

Lori Roberts · GOLD HEART REALTY LLC

Open house Thu, Oct 22 · 9:00 AM22Active

$300,000

3 bd · 3 ba · 1,867 sqft

222 Cloverdale Rd, Winter Haven, FL

Karen Albright · OPENDOOR BROKERAGE LLC

Price Reduced1Active

$309,999

4 bd · 3 ba · 2,039 sqft

5365 San Pietro Dr, Winter Haven, FL

Michael Human · CASA FRESCA REALTY

46Active

$289,000

4 bd · 2 ba · 1,851 sqft

138 Grove Branch Rd, Winter Haven, FL

Michael Stone · THE STONES REAL ESTATE FIRM

15Active

$296,990

5 bd · 3 ba · 2,112 sqft

6245 Botticella Blvd, Winter Haven, FL

Ben Goldstein · LENNAR REALTY

22Active

$278,000

4 bd · 2 ba · 1,830 sqft

703 Avenue L SE, Winter Haven, FL

Sandra Wyhnanskyj, PA · OLYMPUS EXECUTIVE REALTY INC

Price Reduced1Active

$344,999

5 bd · 3 ba · 2,470 sqft

1759 Vanilla St, Winter Haven, FL

Michael Human · CASA FRESCA REALTY

Open house Sat, Oct 24 · 11:00 AM24Active

$340,000

4 bd · 2 ba · 1,701 sqft

128 Lagoon Rd, Winter Haven, FL

Marina Navia, P.A · COLDWELL BANKER REALTY

Price Reduced1Active

$319,999

4 bd · 3 ba · 2,039 sqft

1767 Vanilla St, Winter Haven, FL

Michael Human · CASA FRESCA REALTY

1 2 3…30

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
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

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55+ Community 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

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.