Sleepy Hollow · Kane County · IL
Homes for sale in
Sleepy Hollow Manor.
- Active listings
- 2
- Median list
- $467K
- Avg time on market
- 21 days
- Sold · last year
- 15
Active listings
2 homes on the market
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About the community
The wooded, large-lot village where Sleepy Hollow began.
Sleepy Hollow Manor is the original subdivision that grew into the Village of Sleepy Hollow, a small, heavily wooded community in northern Kane County between West Dundee, Elgin, and Carpentersville. Developer Floyd T. Falese began subdividing the former Sleepy Hollow Farm in 1953 and deliberately rejected the gridded, sidewalk-lined tract of the era: his planner laid out meandering, curbless roads that wind into cul-de-sacs, set homes on lots of at least a half acre, and preserved the tree canopy. Residents voted to incorporate their own village in 1958. The character today is semi-rural and quiet, with mature trees, rolling terrain, large lots, and no commercial or industrial district inside the village.
At a glance
Half-acre-plus wooded lots
Large, tree-covered lots original to the 1950s plan, with mature canopy throughout.
Curbless, no-sidewalk lanes
Meandering roads and cul-de-sacs laid out to preserve a rural, wooded feel.
Voluntary recreation club
The Sleepy Hollow Recreation Association runs a members-only swim and recreation club with a swim team.
Spring-fed lakes
Community lakes original to the developer's plan, historically used for fishing.
Strong event tradition
A volunteer service club runs Fourth of July fireworks, a Halloween bonfire, and other village events.
District 300 schools
Community Unit School District 300, with Sleepy Hollow Elementary located in the village.
Metra access nearby
The Big Timber Road / Elgin station on the Milwaukee District West line is a short drive away.
Residential-only village
No commercial or industrial district inside the village, so day-to-day shopping is a short drive to Randall Road.
What’s close
Sleepy Hollow sits between Randall Road to the west and Route 72 (Higgins Road) to the north, with the Dundees and the Fox River just east and I-90 a short drive south.
- Amenities on-site
- Wooded large lots, spring-fed community lakes, and the voluntary Sleepy Hollow Recreation Association swim club.
- Shopping
- The Randall Road corridor for grocery, big-box, and dining. Note that Spring Hill Mall in West Dundee closed in 2024, so retail has shifted toward Randall Road.
- Hospital
- Advocate Sherman Hospital in Elgin is the nearest full-service hospital, with immediate-care options in West Dundee.
- Highway
- Randall Road connects south to I-90 (Jane Addams Tollway) for the trip toward O'Hare and Chicago.
- Schools
- Community Unit School District 300. The village lists Sleepy Hollow Elementary, Dundee Middle, and Dundee-Crown High School, but assignment is not guaranteed by subdivision, so confirm by address.
- Train
- The Big Timber Road / Elgin Metra station (Milwaukee District West line) into Chicago Union Station is roughly a few miles away.
What it’s actually like to live here
Sleepy Hollow Manor offers a genuinely wooded, low-density lifestyle that is unusual this close to the Randall Road corridor and the I-90 commute. The half-acre-plus lots, curving roads, cul-de-sacs, and mature trees give the village a quiet, semi-rural feel, and residents tend to prize the privacy and the tree canopy. Community identity runs strong for a place this size: the volunteer service club's Fourth of July fireworks and Halloween bonfire, plus the members-only recreation club, give newcomers real ways to plug in.
The tradeoffs are the flip side of that same design. Much of the village has no sidewalks by original intent, which appeals to buyers who want a countrified look but can be a drawback for families who want walkable, stroller-friendly streets. There is no downtown and no commercial base inside the village, so shopping, dining, and services mean a short drive to Randall Road or the Dundees. That lack of a commercial tax base is also part of why property taxes sit on the higher side for the area.
For the right buyer, the value is clear: mature trees, larger lots, and an established neighborhood with easy Metra and I-90 access to Chicago, District 300 schools, and Advocate Sherman Hospital nearby. Homes here are older on average and vary a lot by lot and by updates, so setting and condition matter more than any single home type. Buyers who want a newer, uniform, amenity-HOA subdivision with sidewalks and a clubhouse will find this village is intentionally not that.
Market trends
Why this market moves the way it does
Sleepy Hollow Manor trades on lot, setting, and updates rather than uniform tract pricing. Homes range from original 1950s ranches to larger later builds on wooded lots, so square footage, tree cover, and condition drive value more than any headline figure.
What holds value
The fundamentals matter more than the cosmetics here. Buyers want floor plan, lot, and basement, in that order. Cosmetics are the tiebreaker.
- Lot size and tree cover
- The half-acre-plus wooded lots are the core of the appeal, and larger or more private parcels command a premium.
- Home vintage and updates
- With construction spanning the mid-1950s into the 2010s, an updated home and an original one sit far apart on price.
- The village character
- The curbless, wooded, residential-only setting is a durable draw for buyers who specifically want it.
- Walkability tradeoff
- No sidewalks on many streets appeals to some buyers and deters others, which shapes demand for specific homes.
- Kane County taxes
- Effective rates on the higher side for the area factor into affordability alongside the purchase price.
Real talk
Who shouldn’t buy here
Here is the honest version before you tour.
This is a large-lot, older-home village, so budget for the realities of the housing stock. Many homes date to the mid-century and vary widely in updates and systems, and larger wooded lots mean more grounds to maintain. Tour the specific home, get it inspected, and match the lot to how you actually want to live.
The no-sidewalk, curbless design is intentional and part of the charm, but walk a street before you buy if walkability matters to you. There is also no in-village shopping or downtown, so plan on a short drive to Randall Road or the Dundees for daily errands.
Kane County property taxes run typical-to-high for the area, partly because the village has no commercial tax base, so the residential burden sits on the higher side. Always pull the current bill for the specific parcel with the Kane County Treasurer rather than estimating.
One piece of advice
“If you want mature trees, a big wooded lot, and a quiet village with real community traditions, Sleepy Hollow Manor delivers something you cannot get in a newer subdivision. Just go in clear-eyed: the homes are older and vary a lot, there are no sidewalks on many streets by design, and Kane County taxes are real. Confirm schools by address, inspect the specific home, and you have a distinctive, established place to live.”
The questions buyers actually ask
Sleepy Hollow Manor FAQ
The questions I get most from buyers shopping Sleepy Hollow Manor. If yours isn't here, text 224-385-8779, same-day reply.
- What are property taxes like?
- Roughly $9,000 – $15,000 per year, depending on home size and value. Kane County assessor records are the source of truth. Happy to pull a specific bill on any home you're considering.
- When was Sleepy Hollow Manor built?
- Floyd T. Falese (original developer, planned by Raymond W. Hazekamp) built the community between 1955 and 2012.
- What's the typical closing timeline?
- 30 to 60 days from accepted offer to keys. Cash deals can close in two weeks. Conventional financing is usually closer to 60.
- Does Sleepy Hollow Manor have an HOA?
- The original single-family homes are not governed by a mandatory village-wide HOA. Recreation runs through a separate, voluntary swim and recreation club. If you are looking at a newer attached or townhome product marketed under the same name, confirm whether it carries its own association dues for that specific address.
- What schools would my kids attend?
- The community is in Community Unit School District 300, and the village states children generally attend Sleepy Hollow Elementary, Dundee Middle, and Dundee-Crown High School. Assignment is not guaranteed by subdivision, so confirm the exact schools for a specific address with District 300 before relying on it.
- Why are there no sidewalks on some streets?
- That was intentional. The developer and his planner laid out curbless, sidewalk-free meandering roads in the 1950s to preserve a rural, wooded character. It is part of the village's identity, though it is worth walking a street before you buy if walkability matters to you.
- What do homes cost here and how is the market?
- Prices vary widely because homes range from 1950s ranches to larger later builds on different lot sizes, so there is no single number. Check the live Market snapshot on this page for current active listings and pricing rather than a stale figure.
- How is the commute to Chicago?
- The Big Timber Road / Elgin Metra station on the Milwaukee District West line is a short drive away and runs into Chicago Union Station. Drivers reach I-90 via Randall Road to the south. It is a suburban commute, so plan for a park-and-ride or a highway drive rather than an in-village station.
- Are property taxes high?
- Kane County effective rates run typical-to-high for the area and above national averages, partly because the village has no commercial tax base. Always verify the current bill for a specific parcel with the Kane County Treasurer before you buy.
- Who is the real estate agent for Sleepy Hollow Manor?
- Joe Keegan is the local licensed Illinois real estate broker who covers Sleepy Hollow Manor in Sleepy Hollow, IL through Subdiview, a neighborhood-first home search for the Chicago suburbs and collar counties. Joe prices and negotiates from the live MRED sold comps for Sleepy Hollow Manor specifically, not national averages, and can help you buy or sell here. Reach Joe at 224-385-8779 or joe@joekeeganhomes.com.
Your local agent
Joe knows Sleepy Hollow Manor
Most agents will list anything. I focus on the places I actually know, and the things that move value here don't show up in the MLS write-up: which streets and buildings hold demand, what the HOA or assessments really cover, how the comps read once you account for condition and location, and where buyers consistently want to be.
When you're ready to tour or list, you want someone who has read the last 50 closed comps in this specific market, not a national average, and can tell you what they actually mean for your price. That's how I work. Text or call any time, and I'll give you a real take, not a brochure.
- Licensed Illinois broker
- Comp-driven pricing
- Sleepy Hollow specialist
- Honest local market take
- Brokerocity
Market snapshot
Sleepy Hollow Manor, by the numbers
Live MRED data, refreshed daily. The numbers below tell you what this market is doing today, not what Zillow's algorithm thinks it might be doing six weeks from now.
Typical list price
$467,400
Typical sale price · last 90 days
$470,000
Homes for sale right now
2
Avg time on market
21 days
Sold in the last year
15
This representation is based in whole or in part on data supplied by Midwest Real Estate Data, LLC for the period August 2, 2025 through August 2, 2026. Midwest Real Estate Data, LLC does not guarantee nor is it in any way responsible for its accuracy. Data maintained by Midwest Real Estate Data LLC may not reflect all real estate activity in the market.
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Schools serving Sleepy Hollow Manor
Where Sleepy Hollow Manor homes go to school
Homes in Sleepy Hollow Manor are most often zoned to Dundee-Crown HS. Open a school to see its area, the district, and every home for sale that feeds it.
School assignment is derived from the school the MRED listing agent entered and is not a guarantee. Always verify current attendance boundaries with the district before writing an offer.
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