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Jeep Dealership near Leamington, ON

Experience the Difference at Countryside Chrysler!

Jeep Cherokee

Jeep Grand Cherokee

Jeep Wrangler

Jeep Renegade

Countryside Chrysler - Thrill of Adventure

You can't deny it-you love the thrill of adventure and discovering new places and experiences. Whether that thrill lies within well-established, populated area areas, or in the deepest reaches of untouched wilderness, or anything in between, you're aching to get out there and see it for yourself. For a vehicle that tackles the toughest challenges Mother Nature can muster just as well as blends into an urban environment, nothing does it better than a Jeep vehicle from Countryside Chrysler - your Jeep dealership near Leamington.

Countryside Chrysler - Vehicles for You

Whether you need the compact agility of the all-new Compass, the classic versatility of the Cherokee, the power and refinement of the Grand Cherokee, or the legendary off-road capability of the Wrangler, Jeep has the perfect vehicle to suit your lifestyle, and the best place to take your first step is with the experts at Countryside Chrysler. At our Jeep dealership near Leamington, we know Jeep crossovers and SUVs inside and out, and can assist you with customizing it to your personal preferences so you can drive off with the perfect Jeep-off into new adventures on your own terms.

Our dedicated team is well known around Essex County for their honesty

Award-winning service department, warm hospitality and exceptional attention to you... our customer!

Founded in 1973, the business was built on the premise that "Your Word is What You Are"

Our strong values and customer service were ingrained in our employees that you see here today.

At Countryside, we want to look after all your automotive needs

We believe sales sells the first car but parts and service sell the next two!

Why Choose Countryside Chrysler

Countryside Chrysler - Efficient and Versatile

Efficient and Versatile

With the Cherokee, you're not only getting the iconic Jeep style and capability at your disposal, you're also taking advantage of incredible interior space, advanced safety and technology features, and the best towing capacity of any SUV of its class of up to 2,041 kg (4,500 lb)-all while running at an incredible fuel economy as efficient as 7.8L/100 km (36 mpg) highway! No matter your next challenge, a Jeep Cherokee is set to face it with you.

Countryside Chrysler - Made to Overcome

Made to Overcome

When you drive a Wrangler, you're driving something way beyond your conventional vehicle. You're behind the wheel of Canada's most capable SUV, sporting Best-in-Class 285 horsepower and unrelenting 260 lb-ft of torque. Named "4x4 of the Decade" by FOUR WHEELER, nothing can stand in your way of your destination with a Wrangler by your side.

The only question left is: Where do you want to go first?

Countryside Chrysler - Pillar of the Community

Your Jeep Dealership near Leamington

As the oldest Chrysler dealer in Essex county, Countryside Chrysler has been a part of the local community for over 44 years. Ever since, we have established a reputation for exceptional customer service, honest deals, competitive pricing, and unbeatable knowledge when it comes to the latest Chrysler, Dodge, Jeep and RAM models. Based on the belief that "Your Word is What You Are", our family-owned dealership strives to keep up the high standard that have made us our customers' number one stop for decades.

Countryside Chrysler - All New and All Improved

All New and All Improved

The all-new Compass may seem like a compact crossover with an urban look with an upscale attitude on the outside, but inside it holds all the superior Jeep class and capability you've come to expect. Remarkable versatility is coupled with innovative technology and efficient engineering that come together to deliver Best-in-Class 4x4 capability. As the class-defining crossover, the Compass delivers on both style and substance.


Countryside Chrysler is the oldest Chrysler dealership in Essex County and has enjoyed being the go-to store for clients around the province for decades. In fact, we have become such a staple in the community that we have kept customers coming back repeatedly for over 40 years. Founded in 1973, the business was built on the premise that "Your Word is What You Are". We want you to have the opportunities that you deserve when you reach out to us or walk in our doors. Without hassle or complications, you're going to love what awaits you at Countryside Chrysler.

Take a few moments and explore our online inventory or speak with one of our fantastic representative. We're here for you every step of the way to answer all the questions you might have. This ensures that you receive the care and the commitment to give you every reason in the world to make our dealership into your dealership, too. Let's make your time with us as valuable and enjoyable as possible - come and meet us today at 458 Talbot Road North in Essex-Windsor, Ontario. We can't wait to meet you and reward you with the amazing and professional service you should expect from an award-winning and modern dealership! Your dealership is Countryside Chrysler!

Our Customers Love Us


Finally, a dealership that understands what good service is all about. From sales to service and parts without exception, Countryside delivers what I've been looking for in a dealership. When you see the customers are generational that buy and service here, you begin to think maybe these guys got it right. Well done Countryside, well done.


Giovanni M.


I have only had great experiences at countryside dodge. I love the sales, service and parts i get here. This place is the BOMB. Two nice young men named Sterling and Terry Q work on my vehicle on a regular basis. Those 2 are amazing. I will keep coming back again and again and again.


Taylor B.


The salesman Marco was so genuine and helpful. We felt very comfortable and didn't feel pressured at all. We felt that he cared about our needs and went above and beyond to make us happy. We were treated so well that we actually ended up buying 2 vehicles the same day, 1 new and 1 used. The management team was fantastic too, they all worked together to make the buying experience not only a happy one but one that we will tell all of our friends and family about. Thanks Countryside Chrysler!!


Monica H.

Jeep Dealership near Leamington, ON