Used Jeep Wrangler for Sale near Chestertown, MD

Summary

• With 9,711 currently listed for sale on CarGurus and an average price of $30,424.00, 33.9% of 2021 Jeep Wranglers for sale on CarGurus are rated as good or great deals.
• Favorably reviewed: Owners rated the 2021 Jeep Wrangler 4.7 / 5 stars and CarGurus experts gave it an 7.7 / 10.
• 83.4% of 2021 Wrangler models on CarGurus are accident free.
• The 2021 Jeep Wrangler introduced the powerful Hemi V8 engine option in the Rubicon 392 trim, delivering 470 hp and unmatched off-road performance.

Why it stands out

The Jeep Wrangler excels due to its iconic design and unparalleled off-road capabilities, rooted in a legacy that dates back to the original Willys Jeep. Its combination of rugged features—such as removable doors and tops, a robust four-wheel drive system, and customizable options—makes it a standout choice for adventurers seeking both tradition and modernity. Additionally, with the introduction of innovative powertrains like the 4xe plug-in hybrid and the powerful Hemi V8, the Wrangler effectively adapts to contemporary demands while maintaining its unique character.

Other model years to consider

The 2023 Jeep Wrangler stands out as a viable option due to its high user satisfaction rating of 4.9/5 and a solid market position with 36% classified as good or great deals, reflecting strong value for those seeking a new vehicle. Additionally, the 2020 model year offers excellent affordability at an average price of $27,497.17 while still maintaining a commendable user rating of 4.5/5, making it a smart choice for budget-conscious buyers who do not want to compromise on quality. Lastly, the 2019 model presents another attractive alternative with its competitive pricing and high deal percentage, appealing to those who prioritize both value and satisfaction in their purchase decision.

Model years to approach with caution

When considering Jeep Wrangler model years, the 2000 and 2001 models stand out as the most suitable options, with both averaging around $10,686 and receiving user ratings of 4.7/5. The 2013 model offers a moderate choice with a lower average price of $14,987 but features a reduced user rating of 4.1/5, indicating comparatively lower satisfaction among owners. Additionally, across various years, there is a notable trend of limited availability for good deals, particularly in the earlier models where high percentages reflect fewer favorable options for buyers.

These recommendations are based on CarGurus' proprietary market data from December 17, 2025, CarGurus experts' opinions, and generative AI.