O'Neil Property Group
Windsor’s 1979–early-1990s neighborhood west of 8th Street — single-family homes on 0.7-acre lots plus the village’s only townhomes and condos, from under $200K to $570K.
Surrey Ridge is Sleepy Hollow’s widest-spectrum neighborhood—the only place in the village where a $155K condo and a $570K single-family home share the same streets. Built primarily by Windsor from 1979 into the early 1990s, west of 8th Street off Route 72, the neighborhood runs along Surrey Lane, Acorn Drive, Locust Drive, and Glen Oak Drive. The single-family side offered plans including the Adams, Ashley, Cambridge, Heritage, Homestead, Queen Anne, and Quincy—mostly 2,300–2,900 square feet, with resales now spanning roughly 2,300 to 4,500 square feet on lots averaging about 0.7 acre.
The attached section is what makes Surrey Ridge singular: the village’s only townhomes and condominiums, units around 1,100 square feet that have recently traded between roughly $155K and $200K with monthly assessments generally in the $230–$330 range. Single-family homes carry no association fee. Recent single-family sales have run from about $345K to $570K, and average property taxes land near $7,700—modest for the village. Turnover across both sections is thin: a handful of sales a year combined.
The neighborhood’s position puts the Dundee Township Park District’s Sleepy Hollow Center—tennis, basketball, sand volleyball, playground, preschool—essentially next door on Winmoor Drive, with Sabatino Park’s festival grounds close behind. For buyers, Surrey Ridge is the village’s pragmatic answer: the same wooded, no-commercial-district setting as everywhere else in Sleepy Hollow, at the widest range of entry prices.
Pricing reflects Surrey Ridge sales and MLS-fed sources as of summer 2026.
The village’s only attached housing — two-bedroom units around 1,100 sq ft with assessments covering exterior, lawn, and snow. The lowest entry price in Sleepy Hollow and a steady rental performer.
See listings →The neighborhood’s core two-stories in original-to-partially-updated condition. Recent sales from about $345K make these the village’s most attainable detached homes after the Manor’s entry tier.
See listings →Renovated and larger plans up to roughly 4,500 sq ft — recent top sales at $532K and $570K. Updated Surrey Ridge homes benefit from the neighborhood’s wide price spectrum: they’re the affordable end of the village’s updated-home market.
See listings →Surrey Ridge listings appear within the full Sleepy Hollow search — inventory here is a handful of homes a year, so tell us if you want alerts the day one hits.
The DTPD facility on Winmoor Drive — tennis, basketball, sand volleyball, playground, and preschool — sits at the neighborhood’s edge, the closest recreation access of any village neighborhood.
Attached units and 0.7-acre single-family lots share the same wooded streetscape — the neighborhood reads as village, not complex, which keeps attached-unit demand strong.
Single-family lots average about 0.73 acre with the village’s signature mature tree cover — privacy that newer corridor subdivisions can’t match at these prices.
The neighborhood sits off Route 72, minutes from both the Randall Road corridor and downtown West Dundee — errands and dining split the difference between the two.
Surrey Ridge is served by Community Unit School District 300. Verify current attendance boundaries with the district, as they can change.
The village’s own elementary school, located inside Sleepy Hollow. Confirm the current attendance boundary with District 300 for any specific address.
Located in West Dundee, serving Sleepy Hollow and the surrounding Dundee-area communities; district bus service covers the village.
The area’s comprehensive high school, located in Carpentersville, with academic, athletic, arts, and career-technical programs.
Surrey Ridge’s west-of-8th-Street position puts the Sleepy Hollow Center at its edge and Sabatino Park a few minutes away. Groceries and retail run about ten minutes via Route 72 to Randall Road; downtown West Dundee’s Main Street is just east.
Route 72 west to Randall Road reaches the I-90 interchange in about ten minutes; O’Hare is roughly 35–40 minutes via I-90 and the Loop about 40 miles. Elgin employers and Advocate Sherman Hospital are about ten minutes south.
The Metra Milwaukee District West line’s Big Timber Road station in Elgin is about ten minutes by car, with runs to Union Station in roughly 65–75 minutes.
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