O'Neil Property Group
The Bluffs, Deer Creek customs, and the village’s largest homes — live listings updated daily from the MLS.
Sleepy Hollow’s top end—$600K and up—lives mostly in two neighborhoods. The Bluffs, built between the early 1990s and 2003 near Jelke Creek Bird Sanctuary, holds the village’s newest and largest homes: roughly 2,750 to 4,538 square feet on 0.7-acre lots, with recent sales between $630K and $845K. Deer Creek answers with custom builds averaging about 3,300 square feet on three-quarter-acre lots, where 2026 closings have trended in the mid-$600s and topped $742K. Add the occasional oversized custom in the Manor or Saddle Club Estates and you have the whole luxury market—small, distinctive, and quietly one of the strongest-performing segments in the Dundee area.
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. At this price point inventory is measured in ones and twos — ask us about off-market opportunities.
Expect four-to-five-bedroom homes with three-plus baths, three-car garages, and serious square footage—several Bluffs and Deer Creek homes exceed 4,500 square feet, and the village’s largest run past 5,000. Lots average 0.7–0.8 acres, frequently wooded, with Bluffs homes backing to preserved sanctuary land. HOAs are minimal to none: Deer Creek has no association and The Bluffs carries only a modest assessment—verify the current amount per listing.
The Bluffs is the address buyers name first—streets like River Ridge Drive, Katrina Lane, and Brom Court carry the village’s newest construction and back to Jelke Creek’s trails and ponds. Deer Creek trades newer construction for one-of-a-kind custom builds on Jamestowne Road, Red Bud Circle, and Timber Drive. The 2025 median in The Bluffs ran about $712K; taxes there average $12,000–$13,000, versus roughly $9,200–$10,600 in Deer Creek.
Jumbo financing thresholds matter less here than in Chicago proper—many purchases stay within conforming limits—but appraisals deserve attention: with so few comparable sales, an experienced local agent’s comp package can make or break a deal. Selling? Photography and lot presentation carry disproportionate weight. These homes sell on land, light, and privacy—not just finishes—and marketing that leads with the setting outperforms.
The luxury segment here is thin by design—a handful of sales a year—so both sides need patience and preparation. Buyers should expect to move fast when a Bluffs or Deer Creek home lists, because the $600K–$850K buyer pool in the Dundee area is deeper than the inventory. Sellers should expect a shorter marketing window than the price point suggests: recent Bluffs sales at $845K show what well-presented homes here can do.
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.