Used Porsche convertibles for sale near Montgomery, IL

I have spent my entire life in and around the auto industry and these guys are the only dealer I buy from outside of my own. Dempsey isn't your typical car dealer, and the experience is far more laid back. If you are looking for Unique cars at fair prices, make this place your destination.

I've dreamed of owning a 911 Turbo since I was in my teens. I'm now 63 years old and don't need to drive 150mph anymore. Last year my wife and I decided to look for a convertible to recapture the days of when we first started dating in 1987 when she had a 1982 Fiat Spyder 2000 convertible. We traded that in 2004 on a BMW 330Xi. We had a pretty sweet deal lined up on a 2008 BMW Z4 until the day before we went to pick it up and found out the dealer sold it from under us. What could have really sucked turned into a golden opportunity: we chanced upon a 2001 Boxster S with 59,000 original miles. We have not regretted the decision one bit. Yes, the ergonomics are somewhat dated compared to today and it's not the latest and greatest technology, but we bought it to drive, not to be distracted with all sorts of gizmos. (I'm employed as a Sales representative at a local Chrysler/Dodge/Jeep Dealer for over 35 years. I'm exposed to all the technology). This little Bavarian bomber is an absolute blast to drive; comfortable, quick, sticks to the road like burnt eggs to a cast iron frying pan, and turns heads everywhere. It's capable of 160+ mph, but the right road at 55 mph brings grins all the time. We just went for a weekend trip with it and had no problem with room for our luggage, a tote bag, and a small soft-sided cooler. And as an added bonus, we took it through the famed Hawk's Nest Highway on Route 97 north of Port Jervis, NY. Wonderful to drive, comfortable even after a couple hours, fuel-efficient (except when I play with the Tiptronic on a twisty road), and so far, dead-bolt reliable. So I didn't get my 911 Turbo; the Boxster S is a more than welcome consolation prize. You owe it to yourself. P.S- My wife drives it more than I do!

I chose a used boxster after spending several years reviewing every roadster out there. Everyone you can think of. This car was designed by a genius Harm Lagaay. This is the car that saved Porsche. I know why, design, engineering, fun, performance, reliabilty, every adjective you can tell how great a roadster is doesn't describe how you feel when you drive this car. It is an absolute work of art. Best sports car I ever owned.

I had a fantastic experience at this dealership! From the moment I contacted the dealership while I was in Tennessee, I flew in, and the staff was incredibly friendly, welcoming, and professional. Uri (The rep) took the time to answer all my questions, made sure I felt comfortable, and went above and beyond to help me find the right car. The entire process was smooth, transparent, and stress-free. It’s refreshing to deal with a team that truly values customer satisfaction. Highly recommend this dealership to anyone looking for great service and an amazing team!

I have had 3 Boxster s over the years and this one for over 10. Loved every minute driving it. Great pick up and handling plus two trunks to allow for hauling things. A real head turner. Just need to maintain it for it to keep running well. I'm only selling mine cause we moved down a dirt road and its too rutted for a sports car. I got it for a great price, so letting it go for thousands less than it's blue book.

Professional employees, clean environment, and well maintained vehicles. As a returning customer, this dealer has come a long way and always prioritizes customer satisfaction

I have owned old and new 911’s, including a 2004 911 Turbo, and my current 2006 Boxster Base with the silky smooth 5 speed manual has been the most fun to drive. Small, light, nimble, great exhaust note, etc. It’s just a well-refined, well-engineered and perfectly balanced roadster. I love it. My dad once said “The Germans will always be the world’s best toy makers, and he was right!”

This Boxster has super low mileage (40,500 miles). Its great fun and in very good condition. It has a new clutch, new brakes, and new mats. Needs drivers' seat refurbished. Price: $12,000.

Even though I didn't purchase the vehicle I initially was interested in, the entire encounter with this dealership was impeccable. The owner and his salesman were helpful, patient and respectful. As an individual with autobody and mechanical knowledge, I highly recommend this dealer.

Second Porsche Boxster this lifetime. Fully equipped top down fun with the finest in modern technology. Best value sports car on the market for reliability and motoring enjoyment.

Made the trip from Aurora for my 2018 Audi Q5. Eddie Baker really knows his stuff, and Adam went above and beyond walking me through the tech features. Smoothest buying experience I’ve had.

Incredibly fun car, a blast to toss around in the corners. Not particularly fast cars but they age well and still look fantastic. The convertible top is just the icing on the cake.

I have owned 2 Boxters. First one was a 2001 S series. Currently own a 2008 Base model. These cars are just fantastic to drive. Both were Triptonic. The exterior update on the 2008 is perfect. Only 47,000 miles on it. Bought the car with 34,000 miles on the odometer. Near mint condition. One tip for new owners is to change oil and filter every 5,000miles. I have a great mechanic who specializes Porsches and Land Rovers, I have both. Saves me me big $$$ over dealerships cost costs on repair. Follow the maintenance ‘schedule and you will have a blast. My wife and I love driving through New England with the top down. God I love the car….

We had a great experience working with Noman. He was informative, no pressure, easy to work with, and negotiated fairly. We found a quality used car. After a test drive we had a mechanic check. Along with the Carfax report Noman provided (we also ran our own report which matched), we were confident we knew what we were buying. Plus Noman delivered the car to my home. The car is great! We are very happy. We did shop a few other places and this was the absolute best! Thank you Noman for your good service and am thankful we got a great car!

the Boxter handles like no other Porsche it may not have 911 power but I believe it handles better, a great car I highly recommend it

Had a wonderful experience buying by 2016 Mercedes AMG G63 from Chicago Motor Cars. Seraj “Raj”Abughoush was an amazing sales representative and cares for me start to finish. I was an out of town purchase and Raj walked the car with me twice, did a road test and even fixed an issue he saw with the windshield during our drive together. His manager was very great with his customer service and I will definitely be back to buy another car with Raj and the whole team at Chicago Motor Cars. Was an amazing experience!

What can I say, the benchmark of sports cars. I have a 4S Cabrio. I chose the 4 as I like all-wheel-drive, even in Florida. Better grip. The S also has more horsepower. Build quality and fit and finish our superb. The ultimate sports car without all the problems of the Italian cars. You’d be hard to find a car with better handling and Performance. The look is timeless. There’s no mistake at what you’re looking at when you see a Porsche. Great car.

Amazing service from start to finish! The staff helped me find exactly what I was looking for and made the whole process simple. Definitely a five-star experience.

Incredible car. Perfectly balanced. A true super car that you can daily drive or race around a track. Get the S. Get a manual if you can!

Just purchased a Porsche Cayenne Hybrid, and the experience was fantastic! Simon was knowledgeable, professional, and made the process seamless. The car is a perfect blend of power and efficiency—exceeded my expectations. Highly recommend Simon for anyone looking for a Porsche! 🚘🔋 JD

Good review of a very desirable car but if you want credibility, research why the key is on the left. It's there for Le Mans starts ... remember, drivers ran across the track, jumped in the car and drove off without seatbelts fastened. Having the key on the left allowed the drivers to start the engine with the left hand and shift to first with the right - the cars were all angled off in the direction of the track so as soon as the engine started and the car was in gear, the hands would be brought back to steering.

Purchased a used Audi 8L sight unseen. Bill indicated it was excellent, like perfect and he new the owner and traded it for a different car. I searched many sites for a lower milage vehicle. This one was higher priced but lower milage and pics looked great. It arrived as promised withing a few days of the purchase and wire. Have had the car a few weeks, it does look perfect and runs perfectly. I haven't driven many miles, but am happy and expect it will last many years.

Very fun and surprisingly reliable. Known problems are somewhat commonplace but can be remedied. But pricey which is reflected in the price of the car. No other car I have driven matches the smiles and fun.

Although I didn't buy a high end exotic, I was treated like I was buying one. The 2007 XKR was wonderful and Jackson went above and beyond to answer all my questions, inquiries and upfront about everything with respect to the car. It was prepared beautifully and the transaction was as smooth as could be for an out of state buyer. I would recommend them to anyone looking for a specialty vehicle and hope to deal with them again in the future.

This car is a rocket on 4 wheels. The PDK transmission shifts very quickly with no lag or delay in torque. In fact the torque seems to increase in addition to achieving great gas mileage. That's a formidable task compared to other performance cars. The car does sit low to the ground so if you have bad knees or hips then it might not be a good fit for you.

I contacted them and had a quick response. I was able to test drive the car that night. Everyone there was extremely courteous and able to answer any questions. I ended up buying the car that night. No pressure, no gimmicks, just honest and pleasant. I highly recommend working with these folks, they put the customer first! Thank you, Simon.

Best used car dealership I've been to during my car search. Adam and Eddie were some of the most helpful people that I met at a used car dealership.

Owner of Porsche's since my first purchase new in 1970. 12 registered to me and another 20 or so I bought, drove on dealer plate when I was in used car business.M y 2006 997.1 Carrera 4 Cab with 30k on the odometer is one of the most dialed in cars I have driven. PASM along with the AWD helps keep this one glued to the road. The 4 is Wider than a 2 the S is not necessary. All season road runner. Top down warm weather, AWD for the rest. 😎

I do not provide feedback to anyone unless the experience was excellent (Prior bad experiences). My experience at Napleton was excellent! Jessica, Brian and Julian were friendly, personable and yet professional. Email responses were timely and addressed any concerns or questions I had. The ppf was a late minute addition that was quickly addressed so that the car could be picked up on schedule. The car was prepared and detailed, looked new (CPO). The hospitality was very accommodating. The show room was filled with some really impressive cars. Overall a I left with a very satisfying experience and would recommend this dealership to anyone.

This is my 3rd Porsche and this time I chose the 911 T. I wanted a xxxxx to the wall driving experience in the Smokie Mountains near my home. The T does not disappoint. It performs flawlessly. It hugs the corners -I can easily take 25 mph at 50 mph or more in perfect control. The engine/weight ratio gives more power than can ever be realistically used even if you have a long stretch that is police free. Overall it is a thrill to drive, the cabin is comfortable without being fussy and it growls like a caged tiger with the sport exhaust.

Really outstanding service. Made transactions very easy and fast. People working there super friendly and courteous.

After owning ~20 cars, I find the 2009 911 Turbo to be the perfect understated example of class and performance. Great handling, ride quality and just raw power.