Luxury Homes in Winter Haven, FL

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4 Listings

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Luxury Homes in Winter Haven, FL

4 Listings

32Active
$1,200,000

4 listings

Luxury Homes in Winter Haven, FL

Show Map

4 Listings

Map

Luxury Homes in Winter Haven, FL

4 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

32Active
$1,200,000

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

3 bd · 2 ba · 2,129 sqft

4401 Chambliss Rd, Winter Haven, FL

Cyleste Goodson · FLORIDA REAL ESTATE COMPANY

63Active

$1,399,900

4 bd · 3 ba · 3,309 sqft

3640 Crump Rd, Winter Haven, FL

Amy Reynolds · LOCKHART & ASSOCIATES INC

67Active

$1,195,000

5 bd · 6 ba · 3,235 sqft

250 Brigham Rd NW, Winter Haven, FL

David Small · KELLER WILLIAMS REALTY SMART 1

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

29Active

$1,150,000

6 bd · 6 ba · 6,100 sqft

1200 W Lake Otis Dr SE, Winter Haven, FL

Caspian Collany · COLLANY PROPERTIES

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

August 2026

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 187 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $280,000$204,200–$384,975 typical range
Price per sq. ft.: $154
Sales: 290
Paid in cash: 45.2%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 34 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -5.1%

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

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

August 2026

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 187 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $280,000$204,200–$384,975 typical range
Price per sq. ft.: $154
Sales: 290
Paid in cash: 45.2%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 34 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -5.1%

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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 Aug 31, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Winter Haven, FL community profile

Your local brokerage

Listing data & MLS disclosures

Winter Haven, FL community profile

Winter Haven housing market

Homes that sold · County records, as of Aug 31, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026