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3 beds New construction With a pool

Homes Under $500K in Winter Haven, FL

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24 of 734 Listings

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24 of 734 Listings

46Active

Homes Under $500K in Winter Haven, FL — Page 2

734 listings

Homes Under $500K in Winter Haven, FL

Hide Map

24 of 734 Listings

Map

Homes Under $500K in Winter Haven, FL

24 of 734 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

46Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$240,000

3 bd · 2 ba · 1,447 sqft

2426 6th St NE, Winter Haven, FL

Frankie Eizere · RE/MAX HERITAGE PROFESSIONALS

Open house Sat, Oct 17 · 11:00 AM50Active

$319,900

3 bd · 2 ba · 1,484 sqft

1097 Carefree Cove Dr, Winter Haven, FL

Frankie Eizere · RE/MAX HERITAGE PROFESSIONALS

39Active

$160,000

2 bd · 2 ba · 1,344 sqft

217 Grove Ridge Dr, Winter Haven, FL

Maria Guillen-Hug · LA ROSA REALTY PRESTIGE

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

36Active

$249,000

3 bd · 2 ba · 1,471 sqft

1331 Haines Dr, Winter Haven, FL

David Small · KELLER WILLIAMS REALTY SMART 1

27Active

$79,000

1 bd · 1 ba · 1,078 sqft

200 El Camino #106, Winter Haven, FL

Cynthia Cole · FLORIDA REALTY MARKETPLACE

26Active

$309,990

4 bd · 2 ba · 1,758 sqft

1044 Luke Ave, Winter Haven, FL

Nancy Pruitt, PA · OLYMPUS EXECUTIVE REALTY INC

1Active

$314,990

4 bd · 2 ba · 1,938 sqft

1048 Luke Ave, Winter Haven, FL

Nancy Pruitt, PA · OLYMPUS EXECUTIVE REALTY INC

1Active

$309,990

4 bd · 2 ba · 1,938 sqft

1056 Luke Ave, Winter Haven, FL

Nancy Pruitt, PA · OLYMPUS EXECUTIVE REALTY INC

64Active

$314,000

3 bd · 2 ba · 1,847 sqft

5288 Green Dr, Winter Haven, FL

Pat Pearson · VIEWPOINT VALUE REALTY

33Active

$359,900

5 bd · 2 ba · 2,104 sqft

714 Avenue O SE, Winter Haven, FL

Ileana Perez · HOUWZER INC

35Active

$97,000

2 bd · 2 ba · 1,378 sqft

200 El Camino Dr #102, Winter Haven, FL

Dawn Perkins · LEGACY REAL ESTATE CENTER INC

27Active

$299,900

4 bd · 2 ba · 1,867 sqft

988 Cambridge Dr, Winter Haven, FL

Adrian Alanis Arredondo · THE ORANGE REAL ESTATE GROUP

48Active

$217,000

2 bd · 3 ba · 1,281 sqft

2352 Isle Royale Ct SE, Winter Haven, FL

Michelle Armbruster · LOCKHART & ASSOCIATES INC

52Active

$259,900

3 bd · 3 ba · 1,394 sqft

5101 Magnolia Preserve Blvd, Winter Haven, FL

Manny Quiros · RE/MAX HERITAGE PROFESSIONALS

70Active

$339,000

3 bd · 2 ba · 1,917 sqft

1841 5th St SE, Winter Haven, FL

Juan Jose JR Sanchez, PA · KELLER WILLIAMS REALTY AT THE LAKES

33Active

$286,000

2 bd · 2 ba · 1,429 sqft

575 Saint Andrews Rd, Winter Haven, FL

Elaine Sanders · HOUSE OF GLASS REAL ESTATE PM

18Active

$175,000

3 bd · 1 ba · 1,056 sqft

842 Avenue N SW, Winter Haven, FL

Brooke Madden · KELLER WILLIAMS TAMPA CENTRAL

36Active

$485,000

4 bd · 2 ba · 2,400 sqft

10 W Lake Hamilton Cir, Winter Haven, FL

John Keller, III · JACK KELLER INC

43Active

$284,900

3 bd · 2 ba · 1,576 sqft

1015 Mockingbird Cir, Winter Haven, FL

Annie Wood · HARPER REALTY FL, LLC

Price Reduced13Active

$239,000

3 bd · 2 ba · 2,145 sqft

208 Golf Aire Blvd, Winter Haven, FL

Chris Davies · LINCOLN MADISON REAL ESTATE LLC

57Active

$369,900

4 bd · 3 ba · 2,836 sqft

5809 Windridge Dr, Winter Haven, FL

Kimberly Davis · CROSBY & ASSOCIATES, INC.

66Active

$310,000

3 bd · 2 ba · 1,680 sqft

5344 Nicklaus Dr, Winter Haven, FL

Lori Raath · LAKE ASHTON REALTY INC.

33Active

$289,900

4 bd · 2 ba · 1,999 sqft

4766 Osprey Way, Winter Haven, FL

Mark D'Italia · PROPERTY LOGIC RE

32Active

$302,990

5 bd · 2 ba · 1,708 sqft

2758 Adeline Ave, Winter Haven, FL

Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC

1 2 3…31

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

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Homes with a Pool
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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 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.