Our Story
From delivering pizzas to building a classic car business, the journey of Rhuppert Toledo and his family is one of hard work, passion, and persistence. What started as long nights grinding to make ends meet turned into an opportunity to pursue something greater — restoring and sharing the cars that inspired him since childhood.
Together with his son Rhuppert Jr., the family transformed their vision into Old Town Classics. What began as a dream in the garage has grown into a trusted name in Winter Haven, Florida, where timeless vehicles are brought back to life with care and craftsmanship.
Rhuppert & Rhuppert Jr
For Rhuppert Toledo and his son Rhuppert Jr., classic cars aren’t just a business — they’re a bond. Together, they travel across Florida and beyond, picking up vehicles that are waiting for a second life.
From early mornings on the road to late nights in the garage, every trip is a story: father and son behind the wheel, sharing laughs, lessons, and a vision for what each car can become. Whether it’s rescuing a forgotten icon from a barn or hauling home a rare find, Rhuppert and Jr. turn each pickup into an adventure.
This isn’t just about collecting cars — it’s about building memories, honoring history, and shaping the future of Old Town Classics one ride at a time.
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FounderRhuppert Toledo is the heart of Old Town Classics. What began as a passion for cars in his younger years turned into a lifelong dedication to preserving and restoring the vehicles that shaped automotive history.
From delivering pizzas to turning wrenches, Rhuppert has lived the grind, worked the long hours, and built a life around determination. His love for classic cars isn’t just about engines and chrome — it’s about the stories, the craftsmanship, and the pride of bringing something timeless back to life.
In the shop or on the road picking up cars, Rhuppert leads with vision, patience, and precision. Every restoration reflects his belief that classics aren’t just vehicles — they’re living pieces of history worth protecting and passing down.
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Sales Director
At just 24 years old, Rhuppert Jr. has experienced more behind the wheel than many lifelong collectors. From the growl of American muscle to the elegance of Ferraris, he’s driven and connected with cars most people only dream about.
Raised around the sound of engines and the shine of chrome, Jr. developed his instinct for cars early — not just how to handle them, but how to understand them. Where others see horsepower and steel, he sees character, potential, and history waiting to be written.
Confident yet grounded, Jr. represents the next generation of Old Town Classics. Every mile he drives and every car he touches carries forward the vision he and his father share: that classics aren’t just machines — they’re stories worth living.
Satisfied Customers
FAQs
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We are located at 3427 Decker Hwy, Winter Haven, FL 33880, proudly serving Central Florida and buyers across the U.S.
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We buy, sell, and trade classic cars. Our goal is to connect enthusiasts with timeless vehicles while helping owners find the right buyer for their classics.
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We specialize in classic American muscle cars and vintage icons such as Mustangs, Corvettes, Camaros, and GTOs. We also buy and sell unique imports and rare collector vehicles.
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Yes! We offer trade-in options. If you have a classic you’d like to swap for something in our inventory, we’ll work with you to make it happen.
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Absolutely. If you’d like us to sell your classic, we’ll list it, promote it, and connect it with serious buyers.
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Yes, we do. While we’re based in Winter Haven, we work with buyers nationwide and can help coordinate shipping or transport.
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Simply contact us with your car’s details (year, make, model, and condition). We’ll review it and let you know if it’s a fit for our inventory or trade network.
Location
3427 Recker Hwy, Winter Haven, FL 33880, United States
Contact us
Interested in working together? Fill out some info and we will be in touch shortly. We can’t wait to hear from you!