O'Neil Property Group
Live Sleepy Hollow listings updated daily from the MLS — plus what local buyers should know before making a move.
Under $500K covers the heart of the Sleepy Hollow market—the village median sits near $467K, so roughly half of everything that sells falls in this bracket. The candidates span three neighborhoods: Sleepy Hollow Manor’s ranches, split-levels, and custom builds on half-acre lots (recent sales $415K–$635K), Surrey Ridge single-family homes west of 8th Street (recent sales from about $345K), and the entry end of Saddle Club Estates, Pulte’s late-1980s community, where sales have recently started around $487K. This is the bracket where most first-and-second-home buyers land, and where well-priced listings draw multiple offers.
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 genuine variety: mid-century ranches on wooded half-acres, 1980s two-stories around 2,000–2,600 square feet, and the occasional larger home in original condition. Nearly everything is detached with no HOA, on lots from roughly a half acre to three-quarters of an acre. At the top of the bracket you’re choosing between an updated mid-size home or a larger home that needs work—we help clients price that trade-off street by street.
Three neighborhoods do the work here. Sleepy Hollow Manor is the original—winding lakeside streets from the Falese plan. Surrey Ridge mixes 2,300–4,500 sq ft singles with the village’s only attached homes. Saddle Club Estates brings horse-racing street names and Pulte two-stories from 1986–1991 that have appreciated steadily—its 2023 median of about $454K became roughly $565K by 2025, so its under-$500K listings are increasingly the smaller floor plans.
Come pre-approved with proof of funds ready—the average Sleepy Hollow sale has closed at 100.9% of list and about 44% of recent sales went over asking, which means clean, fast offers win. If you’re selling elsewhere to buy here, get your listing live before you shop; sellers in this village rarely take home-sale contingencies on well-priced homes. And walk the lot as carefully as the house—trees, grade, and lake proximity move value here more than in any nearby town.
Sleepy Hollow inventory averages about a dozen active listings across all prices, so the under-$500K slice might be four to six homes at any moment. The village trades on scarcity: 18 homes closed in the three months ending June 2026 and the median was still $467K. If your target is a specific neighborhood—lakeside Manor, say—tell us and we’ll watch it daily, including coming-soon and off-market conversations.
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.