Browse 379 cars & trucks for sale in Winter Haven, Florida from 2 dealers. Prices range from $4,499 to $259,969. Median price is $37,761. Each listing includes pricing, high-resolution photos, and detailed specifications. Use the financing calculator on any listing page to estimate monthly payments before visiting the dealer.
Winter Haven is dominated by larger volume dealers — averaging roughly 190 listings per dealer — so you're likely to find current-year inventory and aggressive trade-in offers.
Winter Haven shows a wide price spread (57.8× from cheapest to most expensive), typical of a market with both budget pre-owned units and high-end new inventory in the same listings.
Brand selection in Winter Haven is broad: the top three manufacturers represent only about 70% of listings, so cross-shopping is realistic.
Buyers in Winter Haven who don't find what they want locally regularly cross-shop Tampa, Fort Myers, Vero Beach — all within the same Florida dealer network.
Cars & Trucks for Sale near
2026 Chevrolet Silverado 1500
Unknown
2012 Ford Expedition
Unknown
2022 RAM 1500
Unknown
2026 RAM 1500
Unknown
2014 Chevrolet Equinox
Unknown
2019 Chevrolet Silverado 1500
Unknown
2024 Chevrolet Corvette Z06
Unknown
2025 GMC Sierra 1500
Unknown
2025 GMC Sierra 1500
Unknown
2026 RAM 1500
$79,999
Unknown
2026 Mercedes-Benz GLS
$86,272
Unknown
2025 GMC Sierra 2500 HD
$81,544
Unknown
2026 Ford Super Duty F-250 SRW
$99,999
Unknown
2023 Cadillac Escalade ESV
$71,446
Unknown
2026 Chevrolet Tahoe
$84,994
Unknown
2023 Cadillac Escalade
$71,980
Unknown
2024 GMC Yukon XL
$75,983
Unknown
2025 Ford Super Duty F-350 SRW
$83,419
Unknown
2021 Chevrolet Corvette Stingray
$66,762
Unknown
2021 GMC Sierra 2500 HD
$64,930
Unknown
2024 GMC Sierra 1500
$57,983
Unknown
2024 Chevrolet Tahoe
$65,932
Unknown
2023 Ford Super Duty F-250 SRW
$65,263
Unknown
2020 RAM 3500
$59,999
Unknown
Total Listings
379
Average Price
$45,808
Price Range
$4,499 - $259,969
Avg Mileage
26,662 mi
Popular Year
2026
Dealers
2
Discover 379 vehicles for sale in Winter Haven, Florida. With an average price of $45,808, you'll find options from $4,499 to $259,969. Shop from 2 trusted dealerships.
Last updated: October 9, 2026
