AutoSmart

AutoSmart is a classic car dealership on U.S. Route 20 east of Freeport, in northwest Illinois. It is owned by Brian and Donna Caldwell of Lake Carroll, and according to a September 2025 profile in the Shaw Local newspaper, the business first opened in 2010 in Oswego, in Kendall County, and moved to Freeport in 2025. Most of its inventory is classic and vintage vehicles, though the Caldwells also sell newer cars and trucks.

History and the move to Freeport

Shaw Local reports that classic cars were not AutoSmart's priority in 2010. The dealership was licensed for cars, motorcycles and campers, and carried a little of everything. Brian Caldwell told the paper that a friend with a 1960s Corvette convertible asked them to sell it, and that one car pointed the business toward classics. Shaw Local says he has sold classics for about 15 years. After roughly three years of planning, the Caldwells moved the dealership into the former Stephenson County Visitor Center on U.S. 20, with a soft opening on April 1, 2025 and a grand opening with a ribbon cutting and car show on June 11, 2025. The business moved, not closed, and it is operating at the Freeport address. The company says the owners have more than 30 years of experience in the auto industry.

What AutoSmart sells

Caldwell told Shaw Local that the dealership largely deals in classics, which he defined as vehicles 25 years or older, and that it also sells newer vehicles. That fits the way the company describes itself: its site mentions weekend cruisers, muscle cars and classic trucks. Some cars date from before World War II, and at the grand opening one of the oldest was a 1936 Ford roadster street rod. The dealership uses lifts to fit more cars in its showroom, and Shaw Local pictured a 1955 Chevrolet Bel Air displayed that way. The company's home page lists recently delivered cars, including a 1937 Ford roadster sent to Texas, a 1934 Ford Victoria sent to Wisconsin, a 1972 Oldsmobile Cutlass sent to Iowa and a 1962 Chevrolet Impala sent to Calgary, Alberta. Those are the dealer's own examples. Its inventory page loads dynamically, so check it for what is available now.

Buying from AutoSmart

The company's sales page says it offers financing, warranty options, trade-ins, test drives and vehicle inspections, and nationwide shipping. Its financing page says it works with banks, credit unions and finance companies and encourages pre-approval, but no rates or terms are published. For shipping, it says it coordinates with insured transport companies and gives quotes on request. AutoSmart also says every vehicle is inspected and appraised before sale by independent third-party appraisers, and it lists optional warranty contracts for classic and collector cars. Those are company statements, so ask to see the inspection or appraisal paperwork for any car you are considering. A concierge service is also offered for buyers who want the company to locate a vehicle elsewhere, negotiate with sellers and arrange inspection and delivery, for a fee that varies by search.

Selling through AutoSmart

AutoSmart also takes classic, collector and specialty vehicles on consignment, including muscle cars, vintage cruisers and classic trucks. Its consignment page says the company evaluates the car, recommends minor improvements, analyzes the market to set a price, photographs the vehicle, lists it on multiple online platforms, and handles buyer inquiries, showings and negotiations. It states that local consignment is available in Freeport. The fee and the length of the agreement are not published, so ask for both in writing. If you are weighing your options, our guide to consigning a classic explains the usual structure and costs.

Community and events

The Caldwells say they want the dealership to be a gathering place for car people. Shaw Local reported summer cruise nights on the second Wednesday of the month in 2025, with a different make or theme each month, and said the business sponsors local car shows. The company's 2026 event list includes the Spring Rod Run and Pontiacs in Pigeon Forge, Tennessee, a Goodguys show in Des Moines, Iowa, and a Mopar show in Belvidere, Illinois. The owners also run Chicago Jax Wax, a franchise selling car-care products, and AutoSmart carries those products.

Reputation

AutoSmart has operated since 2010, though in a different part of the state until 2025. Its website publishes customer testimonials, including one from a buyer who flew in from California and described buying a car in April 2026. These are selected by the company, so they are not a full picture. We could not open the dealer's Google, Facebook or BBB pages to confirm a current rating, and we did not find a verified BBB profile for this location. Read recent reviews on independent platforms, and verify the title and condition of the specific car.

Visiting AutoSmart

AutoSmart is at 4596 U.S. Highway 20 East, Freeport, Illinois 61032, phone 630-554-2285. Shaw Local listed hours in September 2025 of 10 a.m. to 6 p.m. Monday through Friday and 10 a.m. to 3 p.m. Saturday, but hours can change, so call ahead. To compare other options in the region, see more classic cars in Illinois.