O'Neil Property Group
Live Naperville listings updated daily from the MLS — plus what local buyers should know before making a move.
The two-story is Naperville’s signature product — the colonials, Georgians, and modern traditionals that fill every subdivision from Moser’s 1960s streets to Ashwood Park’s newest customs. This is the deepest inventory slice in the city, which makes it the bracket where comparison shopping actually works: at any given moment you can weigh a 1970s colonial near downtown against a 1990s five-bedroom in a south-side swim community against new construction at the edge, all at overlapping prices.
Looking for help narrowing down your search? Call or text Kealan at 630-381-4995 for a personalized list of homes that match your budget and priorities.
Active listings pulled directly from the MLS.
Expect four bedrooms up, two-and-a-half baths, and a basement as the standard configuration, from roughly 1,800 square feet in the older stock to 3,500–5,000+ in the 90s–2000s communities. Later homes add first-floor offices, three-car garages, and open kitchens; older ones counter with mature lots and locations closer to downtown and the Metra. Primary-suite quality and kitchen updates drive pricing within any vintage.
Vintage maps to geography: 1960s–70s two-stories cluster in central and north Naperville (District 203, closer to downtown), 1980s–90s fill the south side (District 204, swim-club amenities), and 2000s+ concentrate in the luxury communities and infill. The same $700K buys a renovated older colonial near downtown or a larger, younger home further south — that trade-off is the two-story market in one sentence.
Shop by total fit, not square footage alone — a 2,400-square-foot Moser colonial with a finished basement lives larger than its sheet suggests. On 1990s homes, inspect the original roof/windows/HVAC generation; many are at replacement age and negotiable. And decide your district and commute-mode priorities before touring, because the two-story inventory is deep enough to drown an unfocused search.
Because this is the deepest segment, it’s also where pricing discipline shows most: well-priced two-stories go pending in about two weeks while over-ambitious listings accumulate days on market in public view. Buyers can and should use that visibility — stale listings in this bracket are the most negotiable homes in Naperville.
Whether you are just starting your search or ready to schedule a showing, Kealan O’Neil is here to help you every step of the way.
