Best used trucks in Chesapeake, VA
used · trucks · in Chesapeake, VA · observed 2026-10-17
As of 2026-10-17, there are 315 used trucks in Chesapeake, VA. Median asking price $29,500. Best-supported: 2024 Chevrolet Silverado 1500 RST at $33,898, a Great Deal — $10,928 below the comparable midpoint (n=13).
Market snapshot
- Matching
- 315
- Median price
- $29,500
- Price range
- $4,950–$77,978
- Verdict-backed
- 21 of 315
Best-supported used deals
Ranked by Price-to-Market: grouped by verdict — Great Deal first, then Fair Price, then Overpriced — and within each group ordered by how far the asking price sits below the midpoint of its comparable range, then by price. Listings with a long time on lot or an implausible discount are demoted within their group and flagged for verification; high-mileage listings are shown separately.
- Miles:
- 50,258
- Below market:
- $10,928
- Comparables:
- n=13
- Days listed:
- 106
2024 Chevrolet Silverado 1500 RST is $10,928 below the comparable midpoint (n=13 comparables) — the strongest supported price-to-market value here.
- Miles:
- 47,674
- Below market:
- $5,375
- Comparables:
- n=44
- Days listed:
- 78
2023 Chevrolet Silverado 1500 RST is $5,375 below the comparable midpoint (n=44 comparables).
- Miles:
- 56,651
- Below market:
- $4,821
- Comparables:
- n=23
- Days listed:
- 129
2021 Jeep Gladiator Overland is $4,821 below the comparable midpoint (n=23 comparables).
- Miles:
- 27,309
- Below market:
- $3,962
- Comparables:
- n=20
- Days listed:
- 23
2026 RAM Ram 1500 Pickup Laramie is $3,962 below the comparable midpoint (n=20 comparables).
- Miles:
- 39,572
- Below market:
- $3,934
- Comparables:
- n=25
- Days listed:
- 45
2023 Chevrolet Silverado 1500 LT is $3,934 below the comparable midpoint (n=25 comparables).
- Miles:
- 96,239
- Below market:
- $3,804
- Comparables:
- n=32
- Days listed:
- 148
2020 Jeep Gladiator Rubicon is $3,804 below the comparable midpoint (n=32 comparables).
- Miles:
- 27,563
- Below market:
- $3,654
- Comparables:
- n=12
- Days listed:
- 137
2024 Toyota Tundra SR5 is $3,654 below the comparable midpoint (n=12 comparables).
- Miles:
- 50,850
- Below market:
- $3,591
- Comparables:
- n=17
- Days listed:
- 61
2023 Nissan Frontier PRO-4X is $3,591 below the comparable midpoint (n=17 comparables).
- Miles:
- 18,869
- Below market:
- $2,563
- Comparables:
- n=11
- Days listed:
- 71
2025 Jeep Gladiator Mojave X is $2,563 below the comparable midpoint (n=11 comparables).
- Miles:
- 51,045
- Below market:
- $1,979
- Comparables:
- n=17
- Days listed:
- 28
2020 Chevrolet Colorado Z71 is $1,979 below the comparable midpoint (n=17 comparables).
- Miles:
- 90,555
- Below market:
- $7,862
- Comparables:
- n=20
- Days listed:
- 309
2022 Ford F-150 XLT is $7,862 below the comparable midpoint (n=20 comparables). ⚠ Verify — 309 days listed; this discount may not reflect real value.
- Miles:
- 14,717
- Below market:
- $5,907
- Comparables:
- n=63
- Days listed:
- 143
2024 Chevrolet Silverado 1500 Custom is $5,907 below the comparable midpoint (n=63 comparables).
- Miles:
- 88,446
- Below market:
- $5,551
- Comparables:
- n=39
- Days listed:
- 27
2021 Ford Ranger XL is $5,551 below the comparable midpoint (n=39 comparables).
- Miles:
- 35,746
- Below market:
- $4,981
- Comparables:
- n=72
- Days listed:
- 48
2025 Ford F-150 XLT is $4,981 below the comparable midpoint (n=72 comparables).
- Miles:
- 16,752
- Below market:
- $4,625
- Comparables:
- n=65
- Days listed:
- 70
2026 RAM Ram 1500 Pickup Rebel is $4,625 below the comparable midpoint (n=65 comparables).
- Miles:
- 119,327
- Below market:
- $4,454
- Comparables:
- n=54
- Days listed:
- 99
2019 RAM Ram 1500 Pickup Laramie is $4,454 below the comparable midpoint (n=54 comparables).
- Miles:
- 22,440
- Below market:
- $3,256
- Comparables:
- n=28
- Days listed:
- 66
2024 Nissan Frontier SL is $3,256 below the comparable midpoint (n=28 comparables).
- Miles:
- 19,240
- Below market:
- $1,982
- Comparables:
- n=43
- Days listed:
- 77
2026 RAM Ram 1500 Pickup Laramie is $1,982 below the comparable midpoint (n=43 comparables).
- Miles:
- 34,166
- Below market:
- $103
- Comparables:
- n=10
- Days listed:
- 64
2023 Toyota Tundra SR5 is $103 below the comparable midpoint (n=10 comparables).
- Miles:
- 113,629
- Comparables:
- n=21
- Days listed:
- 50
2013 Ford F-150 STX: Fair Price at $12,995.
- Miles:
- 94,500
- Below market:
- $2,003
- Comparables:
- n=66
- Days listed:
- 299
2019 RAM Ram 1500 Classic Tradesman is $2,003 below the comparable midpoint (n=66 comparables). ⚠ Verify — 299 days listed; this discount may not reflect real value.
Other matching listings
These match your search but lacked enough comparables for an OAV price verdict — so they are not ranked as deals.
How OAV ranks these: used vehicles are ranked by price-to-market — how far each price sits below the comparable range for similar vehicles. Objective: best-supported deal. A verdict is shown only when enough comparables exist; otherwise the vehicle is left unscored, and anomalous listings are demoted and flagged for verification. OAV does not currently verify title status — confirm the title and a vehicle-history report before purchase.
Snapshot oav-2026-10-17-va-chesapeake-used-truck-any-collection-answer-v1 · methodology collection-answer-v1. Dealers may pay for analytics access, never for a verdict, ranking, or inclusion.