Homes Under $100K in Winter Haven, FL

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24 of 29 Listings

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24 of 29 Listings

Price Reduced16

29 listings

Homes Under $100K in Winter Haven, FL

Show Map

24 of 29 Listings

Map

Homes Under $100K in Winter Haven, FL

24 of 29 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced16

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$99,000

2 bd · 2 ba · 823 sqft

628 Pavare Ct #1, Winter Haven, FL

Steven Koleno · BEYCOME OF FLORIDA LLC

34Active

$79,500

2 bd · 2 ba · 989 sqft

97 Parson Dr, Winter Haven, FL

Chris Cain · MOSAIC SERVICES LLC

Price Reduced39Active

$98,500

2 bd · 2 ba · 1,347 sqft

1776 6th St NW #304, Winter Haven, FL

Chris Goode · JUDY B CLEAVES PROPERTIES INC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

5Active

$44,900

3 bd · 2 ba · 988 sqft

1116 40th St NW, Winter Haven, FL

Robert Miller, Jr · MILLSHIRE REALTY

Price Reduced12Active

$99,000

2 bd · 2 ba · 1,030 sqft

333 Lake Howard Dr NW #302B, Winter Haven, FL

Karen Myers · UNITED REALTY GROUP INC

11Active

$54,900

2 bd · 1 ba · 672 sqft

213 Lakeside Ranch Cir, Winter Haven, FL

Nadia Aguilar · EXIT REALTY 4CORNERS

12Active

$75,000

2 bd · 2 ba · 864 sqft

187 Sweet Cir, Winter Haven, FL

Darlene Bice · TOWN & COUNTRY REAL ESTATE

Price Reduced57Active

$100,000

2 bd · 2 ba · 942 sqft

345 24th St NW #1, Winter Haven, FL

Ronnie DeCarlo · KELLER WILLIAMS CLASSIC

1Active

$99,900

2 bd · 2 ba · 840 sqft

1700 6th St NW #C31, Winter Haven, FL

Candace Garber · TRUDEALS REALTY CORP

Price Reduced56Active

$92,000

2 bd · 1 ba · 840 sqft

1700 6th St NW #C24, Winter Haven, FL

Chrissi Jasso · ASSOCIATE REALTY

Price Reduced31Active

$83,000

1 bd · 1 ba · 1,078 sqft

200 El Camino Dr #306, Winter Haven, FL

Suzie Rudd · KELLER WILLIAMS REALTY SMART 1

33Active

$78,800

2 bd · 1 ba · 840 sqft

1700 6th St NW #a38, Winter Haven, FL

Shelby Beasley · S & D REAL ESTATE SERVICE LLC

18Active

$92,000

2 bd · 2 ba · 840 sqft

1700 6th St NW #C21, Winter Haven, FL

Don Jerue · KELLER WILLIAMS REALTY SMART 1

32Active

$99,000

3 bd · 2 ba · 1,226 sqft

333 Lake Howard Dr NW #314D, Winter Haven, FL

Justin Cans · IMPACT REALTY TAMPA BAY

28Active

$90,000

2 bd · 2 ba · 1,352 sqft

134 Lake Hazel Dr, Winter Haven, FL

Kelley Blackburn · COLDWELL BANKER REALTY

Price Reduced36Active

$94,900

2 bd · 2 ba · 1,372 sqft

150 El Dorado #105, Winter Haven, FL

Rosalia Abreu · ALLSTATE REALTY SERVICES

70Active

$99,000

2 bd · 2 ba · 1,056 sqft

4253 Cedarwood St, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Price Reduced59Active

$95,000

2 bd · 2 ba · 720 sqft

4173 Rolling Oaks Dr, Winter Haven, FL

KATHY Devor · COLDWELL BANKER REALTY

Price Reduced29Active

$100,000

2 bd · 2 ba · 1,056 sqft

125 Lake Hazel Dr, Winter Haven, FL

Jenn Manzella · FLORIDA REALTY MARKETPLACE

Price Reduced38Active

$90,500

2 bd · 2 ba · 1,176 sqft

188 Sweet Circle Dr, Winter Haven, FL

Chris Cain · MOSAIC SERVICES LLC

Price Reduced33Active

$96,000

3 bd · 3 ba · 1,666 sqft

400 El Camino Dr #210, Winter Haven, FL

Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

Price Reduced21Active

$57,900

2 bd · 1 ba · 248 sqft

7041 Fairview Village Cir, Winter Haven, FL

Sandra Perry · WATSON REALTY CORP.

Price Reduced16Active

$65,000

1 bd · 1 ba · 931 sqft

100 El Camino Dr #111, Winter Haven, FL

Sharon Gastelbondo · LPT REALTY, LLC

Price Reduced19Active

$84,900

2 bd · 2 ba · 1,152 sqft

4165 Rolling Oaks Dr, Winter Haven, FL

Reta Stead · SOUTHERN BELLE 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
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.

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.

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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

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

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