O'Neil Property Group
Sleepy Hollow Home Search

Sleepy Hollow Homes Under $400K

Live Sleepy Hollow listings updated daily from the MLS — plus what local buyers should know before making a move.

~$467K
Median Sale Price
~3,200
Population
27
Schools in District 300
5★
Google Rating

About Sleepy Hollow Homes Under $400K

Under $400K is where detached Sleepy Hollow becomes possible. The candidates are usually the village’s original homes—ranches and split-levels in Sleepy Hollow Manor from the late 1950s through the 1970s—plus the occasional smaller Surrey Ridge single-family and everything in the attached section. With the village median running near $467K, sub-$400K detached listings are the exception rather than the rule, but they do come: recent Manor sales have started around $415K with list prices occasionally dipping below $400K. For buyers who want a half-acre wooded lot in District 300 at the lowest possible detached price, this is the bracket to watch.

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.

Sleepy Hollow Homes Under $400K — Updated Daily

Active listings pulled directly from the MLS.

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What You Can Expect from Sleepy Hollow Homes Under $400K

Expect original-era construction: ranches, split-levels, and modest two-stories from roughly 1,600 to 2,400 square feet, many on half-acre-plus wooded lots with no HOA. Some will be updated; many will be priced to reflect original kitchens, baths, or mechanicals—which is exactly the opportunity. Surrey Ridge attached units (roughly $155K–$200K) also fall in this bracket and suit buyers who prioritize price over land.

Sleepy Hollow Neighborhoods & Local Insight

Sleepy Hollow Manor is the neighborhood to know at this price—the original Falese development, laid out in the late 1950s with winding roads around the village’s three lakes. Homes here have recently sold between about $415K and $635K, so the under-$400K entries are typically the smaller or original-condition properties. Taxes in the Manor run the lowest in the village, averaging in the low-to-mid $7,000s.

Buyer Tips & Financing

Conventional and FHA financing both work here, and for homes needing updates, ask us about renovation loan options (FHA 203k or conventional equivalents) that roll improvement costs into the mortgage. On older homes, budget for a thorough inspection—1950s–70s construction means checking septic/sewer, electrical service, and any original mechanicals. We bring inspectors who know this housing stock.

Good to Know Before You Buy

The math that makes this bracket work: a $380K Manor ranch on a half acre, plus $60K–$80K of updates over a few years, lands you in a house that trades in the mid-$500s in updated condition. Buyers who can see past dated finishes are buying the village’s best value. Be ready to move quickly—entry-priced detached listings draw the widest buyer pool in Sleepy Hollow.

Frequently Asked Questions

Can I really find a house in Sleepy Hollow under $400K?
Occasionally, yes—usually an original-condition ranch or split-level in Sleepy Hollow Manor, where recent sales have started around $415K and list prices sometimes dip below $400K. Surrey Ridge attached homes are reliably under $400K.
What condition are homes under $400K in?
Many are original or partially updated—1950s–70s construction with dated kitchens, baths, or mechanicals priced accordingly. Updated homes in the same neighborhoods typically trade $450K–$600K+.
Do these homes have HOAs?
Detached homes in Sleepy Hollow Manor and most of Surrey Ridge have no HOA. Only the Surrey Ridge attached section carries a monthly assessment (roughly $230–$330).
What are property taxes like at this price point?
Sleepy Hollow Manor averages roughly $7,200–$7,800 a year—the lowest in the village. The overall village effective rate runs about 2.47%. Always verify the actual bill on a specific property.
Is under $400K a good investment in Sleepy Hollow?
The rental pool is small but steady—Manor homes have recently leased between roughly $1,800 and $3,000 a month—and entry-priced homes with update potential have a clear path to equity. We run the numbers for investor clients regularly.

Ready to Find Your Sleepy Hollow Home?

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.