O'Neil Property Group
Live Sleepy Hollow listings updated daily from the MLS — plus what local buyers should know before making a move.
Under $300K, Sleepy Hollow comes down to one address: the attached section of Surrey Ridge. These townhomes and condos—units around 1,100 square feet—have recently traded between roughly $155K and $200K, making them the only consistent path into the village below $300K and one of the least expensive entries into any Kane County village this side of Elgin. What you’re buying at this number is the Sleepy Hollow setup itself: District 300 schools including the village’s own elementary, wooded surroundings, and the Randall Road corridor and I-90 about ten minutes away. Listings at this price appear a handful of times a year, so the buyers who win here are the ones watching daily.
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. Inventory under $300K here is limited to a handful of units a year — if nothing shows below, ask us about coming-soon and off-market options.
Expect two-bedroom attached homes around 1,100 square feet, built between about 1979 and the early 1990s, with monthly assessments generally in the $230–$330 range covering exterior maintenance, lawn, and snow. Detached homes below $300K are rare in Sleepy Hollow—the village’s single-family stock starts in the $300s on its worst day and the $400s more typically. Units with updated kitchens and baths command a clear premium and often draw multiple offers within days.
All of the village’s attached housing sits in Surrey Ridge, west of 8th Street—a Windsor-built neighborhood from the 1979–early-1990s wave that mixes these units in with larger single-family homes on wooded lots. The location puts you near the Dundee Township Park District’s Sleepy Hollow Center on Winmoor Drive (tennis, basketball, sand volleyball, playground) and a short drive from Jelke Creek Bird Sanctuary’s trails. It’s a lot of setting for the price point.
FHA financing with 3.5% down is workable at this price, and Illinois Housing Development Authority programs can layer in down payment assistance for eligible first-time buyers. For any attached unit, have your lender confirm the association is warrantable early—it determines which loan programs apply—and get the assessment amount, what it covers, and the association’s financials before you offer. We pull this for every client automatically.
Because this is the village’s only sub-$300K product, demand is structural: first-time buyers, downsizers who want to stay in Sleepy Hollow, and investors all watch the same handful of units. When one lists well-priced, it moves in days, not weeks. Come pre-approved, tour same-day, and be ready to write. If your budget stretches past $300K, the under-$400K bracket opens up occasional detached homes in Sleepy Hollow Manor—worth a look before you commit to attached living.
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.
