Browse 51 cars & trucks for sale in Winchester, Illinois. Prices range from $19,999 to $86,770. Median price is $44,090. 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.
All 51 cars & trucks listings in Winchester come from a single dealer — expect a consistent inventory mix, but compare prices against the broader Illinois market before committing.
Winchester has a moderate price spread (4.3× from cheapest to most expensive), which usually means a healthy mix of older used inventory and current-year units side-by-side.
Winchester skews heavily toward a few brands — Chevrolet alone accounts for 90% of local inventory.
Buyers in Winchester who don't find what they want locally regularly cross-shop Belleville, Chicago, Morton — all within the same Illinois dealer network.
Cars & Trucks for Sale near
2025 Chevrolet Silverado 1500
WINCHESTER, IL
2026 Chevrolet Silverado 3500 HD Chassis Cab
WINCHESTER, IL
2026 Chevrolet Silverado 2500 HD
WINCHESTER, IL
2026 Chevrolet Silverado 3500 HD
WINCHESTER, IL
2026 Chevrolet Tahoe
WINCHESTER, IL
2026 Chevrolet Silverado 1500
WINCHESTER, IL
2026 Chevrolet Silverado 3500 HD Chassis Cab
WINCHESTER, IL
2025 Chevrolet Express Cutaway 3500
WINCHESTER, IL
2026 Chevrolet Silverado 2500 HD
WINCHESTER, IL
2026 Chevrolet Tahoe
WINCHESTER, IL
2026 Chevrolet Silverado 2500 HD
WINCHESTER, IL
2026 Chevrolet Traverse
WINCHESTER, IL
2021 Chevrolet Suburban
WINCHESTER, IL
2025 Chevrolet Trax
WINCHESTER, IL
2021 Chevrolet Equinox
WINCHESTER, IL
2023 Chevrolet Tahoe
WINCHESTER, IL
2026 Chevrolet Traverse
WINCHESTER, IL
2027 Chevrolet Equinox
WINCHESTER, IL
2026 Chevrolet Trailblazer
WINCHESTER, IL
2022 Chevrolet Equinox
WINCHESTER, IL
2019 Chevrolet Silverado 1500
WINCHESTER, IL
2024 Chevrolet Blazer
WINCHESTER, IL
2022 Chevrolet Silverado 1500 LTD
WINCHESTER, IL
2021 GMC Terrain
WINCHESTER, IL
Total Listings
51
Average Price
$45,277
Price Range
$19,999 - $86,770
Avg Mileage
21,831 mi
Popular Year
2026
Dealers
1
Discover 51 vehicles for sale in Winchester, Illinois. With an average price of $45,277, you'll find options from $19,999 to $86,770. Shop from 1 trusted dealerships.
Last updated: October 23, 2026
