PLAINFIELD REAL ESTATE
Sleepy Hollow Homes for Sale
Browse the latest active homes for sale in Sleepy Hollow, IL — updated daily with new listings.
Recent Sleepy Hollow Listings
A live sample of the 100+ active homes for sale in Sleepy Hollow. Use the filters to narrow your view — or scroll down to see all listings.
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Buying a Home in Sleepy Hollow
Sleepy Hollow is a small, wooded Kane County village northwest of West Dundee, most active in the $375K–$575K range. Most lots are 1/2 acre or larger and feature heavy tree cover — Sleepy Hollow appeals to buyers seeking a quieter, more rural feel within reach of I-90. Heritage Hills and the in-town pockets see steady move-up activity.
CUSD 300 (Dundee-Crown HS) is the school district. The village is mostly residential with limited commercial — the appeal is the lots and the trees. Listings update daily — bookmark this page or save your search to stay current.
→ Read the full Sleepy Hollow community guide for schools, lifestyle, and relocating details.
Sleepy Hollow Market Snapshot
A quick look at what the Sleepy Hollow housing market is doing right now. Last updated May 18, 2026 · Updated daily.
Common Questions About Buying in Sleepy Hollow
Answers to the questions buyers actively shopping Sleepy Hollow ask most.
How fast are homes selling in Sleepy Hollow right now?
Median days on market in Sleepy Hollow is approximately 16 days as of May 2026. Well-priced homes in the $400K–$650K range, particularly in Wesmere Country Club, Liberty Grove, and Lakelands, typically receive multiple offers within the first 7–10 days on market.
What's driving new construction activity in Sleepy Hollow?
Lennar and M/I Homes are actively building in Lakelands, Liberty Grove, Creekside Crossing, and Heritage Meadows. New single-family floor plans start in the high-$400s and many feature open-concept layouts and 3-car garages. Sleepy Hollow's lower property taxes versus DuPage County drive significant relocation demand.
Which Sleepy Hollow subdivisions are most active for buyers?
Wesmere Country Club, Liberty Grove, and Lakelands lead on activity. Heritage Meadows offers larger-lot established homes, and newer subdivisions like Creekside Crossing draw families relocating from Naperville and Bolingbrook. Wesmere has a golf course community appeal that attracts move-up buyers.
What school district serves Sleepy Hollow homes?
Sleepy Hollow homes are served primarily by Sleepy Hollow Community Consolidated School District 202, one of the strongest districts in Will County. District 202 includes Sleepy Hollow North, Sleepy Hollow Central, Sleepy Hollow East, and Sleepy Hollow South High Schools. Always verify school assignment by exact address as boundaries vary across the district.
Are bidding wars common in Sleepy Hollow right now?
Bidding wars happen most frequently in the $400K–$550K range, especially for move-in-ready homes in District 202 boundaries. Above $700K, the market is more balanced with negotiating room available. Our team typically sees 2–5 competing offers on entry- and mid-priced homes within the first week.
How do I schedule a Sleepy Hollow home tour with O'Neil Property Group?
Call or text Kealan O'Neil at (630) 425-8815, or use our contact form. Our office is at 201 E Veterans Pkwy in Yorkville — about 20 minutes from Sleepy Hollow. Buyer consultations are free and we can typically schedule showings within 24–48 hours.
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We've spent years showing homes in Sleepy Hollow and the surrounding area. We know which streets flood, which builders cut corners, and which subdivisions hold value. Reach out — buyer consultations are free.