Homes over $1M in Winter Haven, FL

5 for sale · 9 homes listed · Updated November 9, 2026

• 4401 Chambliss Road, Winter Haven 33884 $1,100,000 · 3 bd · 2 ba · 2,129 sqft
• 13 Bogey Drive, Winter Haven 33881 $1,750,000 · 4 bd · 4 ba · 3,476 sqft
• 1921 Manor Circle Southeast, Winter Haven 33880 $1,295,000 · 3 bd · 3 ba · 2,375 sqft
• 888 Twin Oaks Lane, Winter Haven 33880 $2,000,000 · 5 bd · 5 ba · 4,565 sqft
• 100 Island Way, Winter Haven 33884 $1,100,000 · 4 bd · 6 ba · 4,179 sqft
• 1645 Crump Road, Winter Haven 33881 Pending $1,050,000 · 5 bd · 4 ba · 3,612 sqft
• 1307 North Lake Howard Drive, Winter Haven 33881 Pending $1,250,000 · 5 bd · 4 ba · 3,300 sqft
• 3640 Crump Road, Winter Haven 33881 Active Under Contract $1,399,900 · 4 bd · 3 ba · 3,309 sqft
• 250 Brigham Road Northwest, Winter Haven 33881 Off market since Sep 2026 $1,195,000 · 5 bd · 6 ba · 3,235 sqft