Homes Under $300K in Winter Haven, FL

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24 of 461 Listings

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24 of 461 Listings

New1Active

461 listings

Homes Under $300K in Winter Haven, FL

Show Map

24 of 461 Listings

Map

Homes Under $300K in Winter Haven, FL

24 of 461 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

New1Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$289,900

4 bd · 2 ba · 1,999 sqft

4766 Osprey Way, Winter Haven, FL

Mark D'Italia · PROPERTY LOGIC RE

New4Active

$262,950

3 bd · 2 ba · 1,286 sqft

3877 Avenue O NW, Winter Haven, FL

Angie Reynolds · PORCHLIGHT HOMES LLC

New22Active

$285,000

3 bd · 2 ba · 1,420 sqft

276 Arbuthnot St, Winter Haven, FL

Carmen Montes · CHARLES RUTENBERG REALTY ORLANDO

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

New25Active

$289,800

4 bd · 2 ba · 1,500 sqft

702 Avenue C SW, Winter Haven, FL

Jose Villafana · AGENT TRUST REALTY CORPORATION

New32Active

$175,000

2 bd · 2 ba · 1,248 sqft

1578 Marshall Rd SW, Winter Haven, FL

CarLee Marchetti · STAR REALTY OF WINTER HAVEN

New17Active

$249,900

2 bd · 2 ba · 1,719 sqft

4035 Carteret Dr, Winter Haven, FL

Bryan Rhoads · LKV REALTY, LLC

New33Active

$279,990

4 bd · 2 ba · 1,851 sqft

3101 Royal Tern Dr, Winter Haven, FL

Paul Jacques · XCELLENCE

New40Active

$275,000

3 bd · 2 ba · 1,392 sqft

3406 Fox Ridge St, Winter Haven, FL

Lisa Aportadera · GLOBAL LUXURY REALTY LLC

New24Active

$229,900

3 bd · 2 ba · 1,034 sqft

827 Avenue O SW, Winter Haven, FL

Josh Postlewait · PALMANO GROUP RE BROKERAGE LLC

New29Active

$245,000

4 bd · 2 ba · 1,683 sqft

720 Lake Ned Rd, Winter Haven, FL

Jeff Jones · MARK SPAIN REAL ESTATE

19Active

$175,000

2 bd · 2 ba · 1,103 sqft

1905 Garden Lake Dr, Winter Haven, FL

Renee Butler · BROKERS REALTY OF CENTRAL FLOR

New43Active

$259,900

2 bd · 2 ba · 1,843 sqft

441 San Jose Dr, Winter Haven, FL

Brian Cox · KELLER WILLIAMS REALTY SMART 1

New4Active

$262,950

3 bd · 2 ba · 1,286 sqft

3883 Avenue O NW, Winter Haven, FL

Angie Reynolds · PORCHLIGHT HOMES LLC

New74Active

$179,000

3 bd · 3 ba · 1,584 sqft

5850 Cypress Gardens Blvd #303, Winter Haven, FL

Michael Stone · THE STONES REAL ESTATE FIRM

30Active

$295,000

3 bd · 2 ba · 1,246 sqft

5814 Driftwood Dr, Winter Haven, FL

Solomon Gallant · S & D REAL ESTATE SERVICE LLC

New24Active

$200,000

3 bd · 2 ba · 1,345 sqft

651 Lake Dexter Cir, Winter Haven, FL

Renee Butler · BROKERS REALTY OF CENTRAL FLOR

New38Active

$250,000

2 bd · 2 ba · 1,507 sqft

4302 Shadow Wood Ln, Winter Haven, FL

Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

Open house Sun, Oct 4 · 1:00 PM52Active

$249,000

2 bd · 3 ba · 1,380 sqft

950 14th St NE, Winter Haven, FL

Laura Slocumb · REMAX EXPERTS

New27Active

$145,000

2 bd · 1 ba · 1,209 sqft

624 Lake Elizabeth Dr, Winter Haven, FL

Cheryl Kypreos · HOMESMART

27Active

$236,990

3 bd · 3 ba · 1,423 sqft

3039 Captain Jax Way, Winter Haven, FL

Ben Goldstein · LENNAR REALTY

27Active

$236,990

3 bd · 3 ba · 1,423 sqft

3059 Captain Jax Way, Winter Haven, FL

Ben Goldstein · LENNAR REALTY

35Active

$149,900

3 bd · 3 ba · 1,622 sqft

100 El Camino Dr #301, Winter Haven, FL

Craig Burke · CRAIG BURKE REAL ESTATE GROUP, LLC

35Active

$275,000

3 bd · 2 ba · 1,285 sqft

Address withheld · Winter Haven, FL

Adriana Vazquez · HOME BANKERS REALTY, LLC

Open house Sat, Oct 3 · 11:00 AM25Active

$232,000

3 bd · 2 ba · 1,419 sqft

2668 Rutledge Ct, Winter Haven, FL

Christa Ramirez · KELLER WILLIAMS REALTY

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 100.0% of asking price

Sales here are closing essentially at asking. MLS · 118 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 15, 2026

Median sale price: $266,900$198,500–$329,995 typical range
Price per sq. ft.: $160
Sales: 111
Paid in cash: 38.7%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 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

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 100.0% of asking price

Sales here are closing essentially at asking. MLS · 118 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 15, 2026

Median sale price: $266,900$198,500–$329,995 typical range
Price per sq. ft.: $160
Sales: 111
Paid in cash: 38.7%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $294,400

Homes for sale

762

Median days on market

49 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: -20.9%

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.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Winter Haven housing market

Homes that sold · County records, as of Sep 15, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Winter Haven, FL community profile

Explore Winter Haven homes

Your local brokerage

Listing data & MLS disclosures

Winter Haven, FL community profile

Winter Haven housing market

Homes that sold · County records, as of Sep 15, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Price trend · Assessor repeat sales, as of Sep 30, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026