Welcome, Chester Customers!

Discover the Eastern Shore in your new car from Bayside Chrysler Dodge Jeep Ram, where all roads lead to the water! As your local Chester, MD, Jeep dealer, we serve the region by providing quality vehicles, services, and guarantees. While you're stopping to purchase or lease one of our vehicles, explore all that Annapolis has to offer. As the state capital of Maryland, this beautiful city boasts centuries-old architecture with a contemporary feel. Shop at the local Annapolis Harbour and Town Centers or take a stroll down Main Street and visit Annapolis's thriving art district. This paradise, located on the shores of the Chesapeake Bay, is famous for its crab cakes, gorgeous shoreline, and is home to the US Naval Academy. Catch a football game at Navy-Marine Corps Memorial Stadium and maybe see the famous U.S. Navy Blue Angels flyover. Finding something to do is easy, all close to your local Chester, MD, Jeep dealer.

Options for Your Needs

As the leading Dodge dealer near Chester, MD, we pride ourselves on offering a wide range of selections. We are also a leading Chrysler dealer near Chester, MD, and the leading Ram dealer near Chester, MD, meaning you have many models from which to choose. We have options for you from the reliable Chrysler Pacifica, to the fast and sporty Dodge Challenger, that combines comfort with looks and performance. With every purchase of a vehicle from Bayside CDJR comes a promise. Simple. Honest. Fair. Don't choose just any used car dealer near Chester, MD, Choose a dealer you can trust to give you transparency every step of the way, making the process of buying your vehicle simple and easy to understand.

Bayside Cares

Buying a car can be intimidating, but it doesn't have to be at your Jeep Dealer near Chester, MD. Visit our finance center online and fill out our financing application to make buying quick and easy or give us a call at 410-934-0752 with any questions. We also have a payment calculator readily available so you can forecast your price point in advance of visiting us. We want you to leave our lot completely satisfied with your purchase, which is why we offer a 7-day exchange policy allowing you to bring your pre-owned vehicle back to the dealership for full credit towards your next purchase. At Bayside CDJR, we believe when you become a customer, you become family, which is why we have Bayside For Life. All qualified new and used vehicles come with a Limited Lifetime Engine Guarantee. At your local Chester, MD, Jeep dealer, we offer car buying without the stress.

Shop Bayside Today

Bayside CDJR is the preferred Jeep dealer near Chester, MD, you can trust. We build our relationship with customers by offering competitive prices and the Bayside For Life guarantee. We value you as a customer and want to see you leave with the car of your dreams. Schedule a test drive today!

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76 Vehicles matching:
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  • 2026 Jeep Wrangler 4-DOOR WILLYS

    • MSRP:$53,005
    • Bayside Savings:$5,505
    • Sale Price:$47,500
    • Confirm Availability
    • Get Pre Approved
    Stock #:
    TW232187,
    Bodystyle:
    Sport Utility,
    Drive Line:
    4x4,
    MPG Range:
    20/22,
    Exterior Color:
    Anvil Clear-Coat Paint,
    Interior Color:
    Black Interior Color,
    Model Code:
    JLJL74,
    Transmission:
    8-Speed Automatic Transmission,
    Engine:
    2.0L I4 DOHC DI Turbo Engine w/ ESS
    VIN:
    1C4PJXDN0TW232187
    More
    Convenience Group, Steel Power Dome Hood Package
  • 2026 Jeep Grand Cherokee ALTITUDE 4X4

    Stock #:
    TC202936,
    Bodystyle:
    Sport Utility,
    Drive Line:
    4x4,
    MPG Range:
    19/26,
    Exterior Color:
    Diamond Black Crystal Pearl-Coat Paint,
    Interior Color:
    Black Interior Color,
    Model Code:
    WLJH74,
    Transmission:
    8-Spd Auto 8HP80 Trans (Buy-US),
    Engine:
    2.0L I4 Turbo GME EVO w/ESS
    VIN:
    1C4RJHAR9TC202936
    More
  • 2026 Jeep Grand Cherokee ALTITUDE 4X4

    Stock #:
    TC201721,
    Bodystyle:
    Sport Utility,
    Drive Line:
    4x4,
    MPG Range:
    19/26,
    Exterior Color:
    Baltic Gray Metallic Clear-Coat Paint,
    Interior Color:
    Black Interior Color,
    Model Code:
    WLJH74,
    Transmission:
    8-Spd Auto 8HP80 Trans (Buy-US),
    Engine:
    2.0L I4 Turbo GME EVO w/ESS
    VIN:
    1C4RJHAR5TC201721
    More
  • 2026 Jeep Grand Cherokee ALTITUDE 4X4

    Stock #:
    TC202935,
    Bodystyle:
    Sport Utility,
    Drive Line:
    4x4,
    MPG Range:
    19/26,
    Exterior Color:
    Bright White Clear-Coat Paint,
    Interior Color:
    Black Interior Color,
    Model Code:
    WLJH74,
    Transmission:
    8-Spd Auto 8HP80 Trans (Buy-US),
    Engine:
    2.0L I4 Turbo GME EVO w/ESS
    VIN:
    1C4RJHAR7TC202935
    More