Old Town Classics

Old Town Classics is a small, family-run classic car business on Recker Highway in Winter Haven, Florida, in Polk County between Tampa and Orlando. The company says it buys, sells, trades and consigns classic cars, and that it restores them as well. Its online inventory is short and eclectic, mixing American classics with motorcycles, a restored mini tractor and a rollback truck, so it reads more like a hands-on shop than a large showroom dealer.

A father and son business

According to its own website, Old Town Classics was founded by Rhuppert Toledo and is run together with his son, Rhuppert Jr., who is listed as sales director. The company tells its story in plain terms: Toledo went "from delivering pizzas to building a classic car business," and the venture began as a garage project before moving into the Winter Haven location. The site says the two travel around Florida and beyond to pick up cars for the business.

The website does not give a founding year. Florida corporate records show Old Town Classics FL, LLC was filed in January 2023 with its principal address at the Recker Highway site, and an earlier company with a similar name was formed and then voluntarily dissolved in 2022. In its current form, then, this is a young business.

How the business works

Old Town Classics describes several ways to deal with it. It says it buys single vehicles and full collections and offers "fair market appraisals," takes trade-ins, and runs what it calls a "no-fee consignment program" that puts a car in front of buyers across the country. The site also mentions a referral program that pays people who send in an owner whose car the company then buys.

Owners who want to sell are asked to send the year, make, model and condition of the car, and the company says it will decide whether the car fits its inventory or its trade network. The website does not publish written consignment terms, so anyone considering it should ask how long the agreement runs, where the car will be kept, who insures it while it is there and how the sale price is agreed. If you are weighing that route, our guide to consigning a classic covers the questions to settle before you sign anything.

What it sells

The company says its focus is American muscle and vintage icons such as Mustangs, Corvettes, Camaros and GTOs, along with unusual imports and collector vehicles. The inventory we saw in early October 2026 was smaller and more varied than that description suggests. It included a 1965 Ford Mustang convertible with a 289 V8 and four-speed manual, a 1930 Ford Model A pickup built as a street rod, a lowered 1951 Plymouth Suburban wagon with a small-block Chevrolet V8, a 1978 Chevrolet Corvette coupe, a 1987 Mercedes-Benz 560SL and a 1981 Volkswagen Rabbit pickup. Alongside them were custom motorcycles, a 2011 Jaguar XF, a 2007 International rollback and a restored Bush Hog mini tractor. Listed prices ran from $5,000 to $50,000.

With only around fifteen vehicles listed, what is for sale changes quickly. Buyers comparing options can also browse Florida classic cars for sale from other sellers.

Buying from Old Town Classics

Several listings carry a note that $500 is a deposit to hold a vehicle for 30 days and ask buyers to call for the actual price, so the figure shown online may not be the final asking price. Confirm the price, what the deposit covers and whether it is refundable in writing before paying anything.

The company says it works with buyers outside Florida and can help coordinate shipping, and its homepage mentions worldwide shipping. The site does not mention financing or an inspection program, so buyers should plan to arrange both themselves. For any car bought at a distance, ask for the VIN and title status, extra photos or a video, and have an independent inspector look at the car first.

Reputation

We did not find a Better Business Bureau profile or a meaningful body of third-party reviews for this Winter Haven business during our research. The testimonials on the company's own site are signed with first names only and cannot be checked independently. That is common for a business of this age and size, but it means buyers have less public track record to go on, and the usual checks on paperwork and condition matter all the more.

Two practical notes help avoid confusion. Old Town Classics in Winter Haven is not connected to the similarly named Old Town Classics car buyer in San Diego. And parts of the company's website refer to Winter Park, a different city near Orlando, although every listing and the contact page place the business in Winter Haven.

Visiting Old Town Classics

The business is at 3427 Recker Hwy, Winter Haven, FL 33880, which the company describes as minutes from downtown Winter Haven. The shop number is 863-999-1545, and most vehicle listings give a separate mobile number for inquiries. No opening hours are published, so call ahead before driving out to see a particular car.