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3 beds New construction With a pool

Homes Under $300K in Winter Haven, FL

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24 of 457 Listings

Map

24 of 457 Listings

Homes Under $300K in Winter Haven, FL — Page 2

457 listings

Homes Under $300K in Winter Haven, FL

Hide Map

24 of 457 Listings

Map

Homes Under $300K in Winter Haven, FL

24 of 457 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$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

$79,000

1 bd · 1 ba · 1,078 sqft

200 El Camino #106, Winter Haven, FL

Cynthia Cole · FLORIDA REALTY MARKETPLACE

27Active

$299,900

4 bd · 2 ba · 1,867 sqft

988 Cambridge Dr, Winter Haven, FL

Adrian Alanis Arredondo · THE ORANGE REAL ESTATE GROUP

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

21Active

$200,000

2 bd · 2 ba · 1,776 sqft

104 13th St SE, Winter Haven, FL

Chuck Ferdinandsen · CHARLES RUTENBERG REALTY ORLANDO

52Active

$259,900

3 bd · 3 ba · 1,394 sqft

5101 Magnolia Preserve Blvd, Winter Haven, FL

Manny Quiros · RE/MAX HERITAGE PROFESSIONALS

Open house Tue, Oct 20 · 4:00 PM48Active

$217,000

2 bd · 3 ba · 1,281 sqft

2352 Isle Royale Ct SE, Winter Haven, FL

Michelle Armbruster · LOCKHART & ASSOCIATES INC

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

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

33Active

$289,900

4 bd · 2 ba · 1,999 sqft

4766 Osprey Way, Winter Haven, FL

Mark D'Italia · PROPERTY LOGIC RE

22Active

$285,000

3 bd · 2 ba · 1,420 sqft

276 Arbuthnot St, Winter Haven, FL

Carmen Montes · CHARLES RUTENBERG REALTY ORLANDO

4Active

$262,950

3 bd · 2 ba · 1,286 sqft

3877 Avenue O NW, Winter Haven, FL

Angie Reynolds · PORCHLIGHT HOMES LLC

52Active

$225,000

2 bd · 2 ba · 1,471 sqft

2825 Wingfoot Ct, Winter Haven, FL

Hugo Hernandez · COLDWELL BANKER REALTY

17Active

$249,900

2 bd · 2 ba · 1,719 sqft

4035 Carteret Dr, Winter Haven, FL

Bryan Rhoads · LKV REALTY, LLC

28Active

$175,000

2 bd · 2 ba · 1,248 sqft

1578 Marshall Rd SW, Winter Haven, FL

CarLee Marchetti · STAR REALTY OF WINTER HAVEN

25Active

$289,800

5 bd · 3 ba · 1,726 sqft

702 Avenue C SW, Winter Haven, FL

Jose Villafana · AGENT TRUST REALTY CORPORATION

24Active

$229,900

3 bd · 2 ba · 1,034 sqft

827 Avenue O SW, Winter Haven, FL

Josh Postlewait · PALMANO GROUP RE BROKERAGE LLC

40Active

$275,000

3 bd · 2 ba · 1,392 sqft

3406 Fox Ridge St, Winter Haven, FL

Lisa Aportadera · GLOBAL LUXURY REALTY LLC

33Active

$279,990

4 bd · 2 ba · 1,851 sqft

3101 Royal Tern Dr, Winter Haven, FL

Paul Jacques · XCELLENCE

19Active

$175,000

2 bd · 2 ba · 1,103 sqft

1905 Garden Lake Dr, Winter Haven, FL

Renee Butler · BROKERS REALTY OF CENTRAL FLOR

4Active

$262,950

3 bd · 2 ba · 1,286 sqft

3883 Avenue O NW, Winter Haven, FL

Angie Reynolds · PORCHLIGHT HOMES LLC

Open house Fri, Oct 16 · 10:00 AM43Active

$259,900

2 bd · 2 ba · 1,843 sqft

441 San Jose Dr, Winter Haven, FL

Brian Cox · KELLER WILLIAMS REALTY SMART 1

Price Reduced23Active

$299,900

3 bd · 2 ba · 1,525 sqft

3304 Costello Cir, Winter Haven, FL

Jason Stone · BHHS FLORIDA PROPERTIES GROUP

1 2 3…20

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.