Used convertibles for sale near Stow, MA under $50,000

I have purchased a couple vehicles here for my family and Kevin and his team have always been super helpful. I appreciate the time you take to review the different options on financing and help us understand the process. Thank you!

I bought this car as the baseis of a new hobby build. It had the performance options I wanted and was an automatic. Two items the dealer failed to disclose were worn tires and two curb checked wheels.

John and Kieran were exceptional throughout the entire transaction. John was a pure pleasure and professional. Our vehicle purchase process was truly the easiest and smoothest we ever experienced. We highly recommend John and his team.

Bought my 2016 Mustang GT used have had it exactly one year it has 45,000 miles on it, haven't had one problem it runs great and is fast! . And I'm always still getting compliments on it. It looks great, is fun to drive, and still turns heads. This is my 8th Mustang I'm a Mustang fantatic! Love them.

I had an excellent experience. My salesman was knowledgeable and helpful. I was there for a total of three hours and drove away with a Porsche Macan!

Great driving comfort,loaded with features. Safety is definitely a priority with the MB engineering . I have leased a total of 4 Mercedes and totally satisfied with every single one.

Thank you Ahmed for your professionalism and assistance. Almost 1 year after I purchased my car with Ahmed, he still follows up and even helped me during my latest maintenance appointment....That's what I call continuous and AWESOME customer service!!! "Shokran = Thank you" my friend.

I love, love, love my new Cooper S convertible! She is paying for herself in compliments already. Literally everywhere I go, someone stops me and says "your car is so cute!" She is so fun to drive and it isn't even convertible weather yet lol. I ordered black on black and I couldn't be happier with the aesthetics and performance! I hope she and I have mini happy years together!!

Buying a car from Mo was great. I do not like buying cars. I do not like the standard buying script. Thankfully, Mo talked me through the process. Showed me a coupe of vehicles and never pressured me to buy. With his assistance, I was able to make the buying decision that was best for me. In my experience, the prices were more than fair. The team was awesome and they continue to work with you after the sale closes. If you have researched your desired vehicle. Know the prices and what is available. Go see Mo. He probably has the car for you at a great price.

I bought a 07 CLK 63 AMG about a year and a half ago and never had so much fun in a car since a 62 Shelby Cobra! The CLK is very well appointed and it looks a bit of a sleeper but it does not when you wick it up. I have a Dragy and use it to do 0-60, 1/4 mile and Speed mile. I am getting better at driving this car as times will show. If you are looking for one of these you will have your work cut out. I took me 6 mon. and nation wide search. I found a perfect one with 22K. Love it.

During my search for my next vehicle I recalled the hassle of buying a vehicle. I read the reviews on Drum Hill website. I was pleasantly impressed. Especially the reviews that mentioned John. I’m a very skeptical person and is cautious what I read especially on someone’s own website. I had already seen a vehicle that I was quite interested in. It was time to test the validity of these reviews. I was treated incredibly well and you could feel that they weren’t doing a song and dance. When I typically ask a car salesman about something on a vehicle, it seemed at time they would be squirming. Not here and especially not with John! I don’t like using an explanation mark but I had to in this case. The most impressive thing was being in the background while he was with a customer. He had zero to hide! He would insist to customers to take the vehicle to the manufacturers and have them inspect it before they buy it. You could tell in his voice that he was truly looking out for your best interest! He has been in the business for some 35 years and his knowledge is impeccable. From a vehicle’s options and what they do. Financing, recalls, different state laws and so much more! You can tell as there is zero hesitation when he speaks. I like you, maybe right now, this does sound to good to be true. Like John would say, “Challenge me and I am 100 % positive, my word is the most important thing to me”. I have one more explanation point left. I say to you “Take my word in believing Auto Hill autos”. It’s a must check before completing your search!

This Beetle was my car that I traded in recently for a new Tiguan. The car was excellent, and always reliable. We wanted to own one of the last Beetles made, and glad that we purchased it from Mt. Prospect VW (AutoBarn) four years ago. Whoever purchases this bug, is getting a great car, and we will miss it!

IVE DONE BUSINESS HERE MANY TIMES- I HAVE NOTHING BUT KIND WORDS AND PRAISE TO SAY ABOUT THIS CAR DEALER - THE TVERY BEST BEST DEALER AROUND TOWN

So glad I got my fun car for myself. I got it mint condition. I love the hard top convertible, automatic and manual driving. It actually has great trunk space for a weekend bag.

Thank you very much for your help and great service and your support with the issue

I have my 1999 CLK 320 Convertible for 12 years , It is great car , fast, comfortable , stylish , good gas mileage , has 12 sparkplugs , 2 for each cylinder ,if you live in a city with good weather like where I live in San Diego,CA you will gett great experience with convertible car ,my top is down most of the year.

Very prompt, professional and attentive. It was a pleasure to deal with them. They are definitely a dealership I will contact again in the future!

The EOS is a great hardtop convertible with a flair for fun and sun comfort. The car rides well, get good gas milage and looks great. I would recommend one of these care to anyone wanting a sexy convertible.

I bought a 2011 Chevy Suburban. Liam and John were fantastic. Amazing is an understatement. I did not know there are actually car dealerships anymore that go this above and beyond and as pleasurable to deal with. A+++++++++

A few concerns to address, the first is ABC active body control is a concern for this car. I own Phone Doctor in Frederick Maryland and hardware tech is my passion so I want to give my feedback. I love the classy lines of the exterior. The interior is equally elegant and tasteful without gaudy disco lights. I was mesmerized into test driving a 2005 SL500 because my daily driver is a 2001 Mercedes s600. The audio system is lackluster, next weakness is the headlights, but the biggest problem is the ABC (active body control) hydraulic suspension. The audio system is disappointing and leaves me feeling flaccid but I’m used to twelve inches of JL systems shimmed into my high school hoopties. The audio system is not the deal-breaker for this $90,000 machine. And the mediocre headlights can be remedied with aftermarket auxiliary lights. The biggest weakness is the high performance suspension system. Mercedes likes to call it ABC (active body control). The hydraulic pump, seals, and mechanical moving parts gets weak and loses its performance anywhere between 80,000 to 150,000 miles. It’ll cost just as much to replace the ABC system than it does to purchase your 2nd hand sl500. If you’re in the market for one make sure you have an extra $20,000 in socked up before you drop your drawers and plop $15k on your first SL500. A dream ride with one last caveat: This car will draw a lot of attention from single ladies!

John at Drum Hill is the best buying experience I have had in years. He is very professional, his office manager is very responsive to her customers. They shipped my Mini Cooper to Maryland thru the snow. My Wife has since taken it from me. Their prices are very fair and the vehicle was in excellent condition!! We are very happy with Them and will buy another car from them in the future and can count on a wonderful buying experience. From Massachusetts to Maryland with an understanding and honest dealership!!! Fantastic

My wife and I have been looking for a midsize midrange convertible for years and after seeing a Cascada in a parking lot knew this was the car we wanted. It has all the bells and whistles you’d find in a BMW, Mercedes or Audi at a fraction of the cost to purchase and maintain. Although they’ve been discontinued as of 2019 now is the perfect time to find a newer used car with low miles for half the sticker price. The only drawbacks are the MPG isn’t optimal and you can’t link your iPhone to the display screen, but the pros (beautiful car, tons of standard features, handles great, decent back seat / trunk space) far outweigh those two potential cons.

The whole experience was very positive. All the people were friendly and professional. Have had the car now over a week. It’s everything that I hoped it would be.

plenty of head room and usb ports. i have gotten used to it slowly and hope to have lots os fun as i learn more about this fine car.

We bought a used 2020 Cooper S convertible in December 2022 with only 6,000 mile on the odometer. It is a blast to drive! Don't plan on taking passengers unless they are very small children or pets. Looking forward to warmer weather and many cruises although we did put the top down and took a spin in it on Christmas day.

I had an exceptional experience purchasing a vehicle from Highline Group. Upon expressing interest in a test drive, Sales Manager Ted promptly contacted me to arrange the appointment. During the test drive, Salesperson Robert exhibited remarkable enthusiasm and provided a comprehensive overview of the vehicle’s features, addressing all of my questions and concerns. The vehicle was in impeccable condition, as Robert explained that Highline Group maintains an in-house service facility to ensure rigorous quality control. The dealership’s showroom was impressively stocked with a diverse collection of Ferrari, Ducati, and other high-performance vehicles. I promptly finalized the purchase, secured by Highline Group’s competitive loan rate that surpassed offerings from other institutions. I collected the vehicle within one week and have been thoroughly satisfied with the experience. I look forward to returning for future purchases and will confidently recommend this dealership to my associates.

Recently purchased a 2024 4 series convertible. Love the way it looks and drives. ‘Ordered the car with the assumption that it had the cruise control and lane as dust that I was used to in my other vehicles. This car does not come standard with a front facing camera. Also does not come standard with the cruise that is what I call “radar” cruise. Just putting it out there for anyone shopping. I do love the car.

I love the M-sport package look on this car. It looks sleek and sporty. With a cold air intake this car sound beautiful. Rides great and can save a lot of gas in eco mode vs sport mode. Paddle shifters are fun and responsive.

I was working with a few different dealerships and none of the salespeople had the knowledge of Thomas at tulley they where very upfront and honest didn’t play and dealership games and got to my number no fighting back and forth

Absolutely love it, loaded with features including self parking. Sports car with different drive modes and yet luxury comfortable. So far not a single issue, very reliable. Highly recommend.

It looks just as good as a 911 without the sticker price a head turner whenever it’s on the street I am always asked if I want to sell the car the answer is no way

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!

Best covertible under $30k used. Italian styling/handling and Japanese reliability. What a car. As a previous 911 and SL 300 owner, I prefer this as a toy without the expensive repairs. All parts are Japanese and repairs are minimum. Best KEPT secret, buy a classic car, and enjoy for years! Handling is insane! Not a daily driver!