Sherwood Road runs through the Dempsey neighbourhood in north Milton, a quiet residential pocket that feels removed from the town's busier corridors.
Sherwood Road runs through the Dempsey neighbourhood in north Milton, a quiet residential pocket that feels removed from the town's busier corridors. The street is short, lined with a mix of detached homes, semis, and townhouses built in the early 2000s. It sits within walking distance of Chris Hadfield Public School, and the Milton GO Station is a ten-minute drive south. The surrounding area is defined by parks and conservation lands, giving Sherwood a suburban calm that appeals to families. Its position near Highway 401 at Regional Road 25 makes commuting straightforward without sacrificing the street's low-traffic character.
Sherwood Road's housing stock is a compact mix of detached homes, semis, and townhouses, all built in the early 2000s. The street carries a single detached property, one semi-detached home, and two townhouses, each with two-storey layouts and attached garages. Brick and vinyl siding are the dominant exterior treatments, and lots are modest in size, consistent with the neighbourhood's density. The builder is not publicly attributed with high confidence, but the homes share a consistent architectural language typical of Milton's early-2000s infill developments.
Townhouses on Sherwood typically offer three bedrooms and one-and-a-half to two bathrooms, with finished basements in some units. The detached home sits on a slightly wider lot, with a front-facing garage and a private backyard. Across the Dempsey area, townhomes of this era trade around $755,000, reflecting the street's position in a stable, established pocket. The homes are well-maintained, with several showing updated kitchens and flooring. The street's small scale means each property feels distinct, yet the overall character is cohesive.
Sherwood Road is within walking distance of Chris Hadfield Public School, which sits at the street's northern edge. Several other elementary schools are a short drive away, including Robert Baldwin and Anne J. MacArthur. For groceries, Walmart Milton and FreshCo are both four minutes by car, while Sobeys and Canadian Superstore are five to six minutes away. Milton District Hospital is five minutes west, and the Milton GO Station is a ten-minute drive south, connecting to Toronto in about 70 minutes.
Parks are plentiful in the area. Coates Park and Velodrome Park are each a six-minute drive, and the larger Kelso Conservation Area is ten minutes away for hiking and seasonal activities. The Milton Muslim Community Centre is four minutes by car, and the Islamic Community Centre of Milton is nine minutes. Highway 401 at Regional Road 25 is four minutes from the street, making commutes to Mississauga, Oakville, and Burlington straightforward. The street's quiet residential feel is balanced by easy access to daily essentials.
Sherwood Road trades infrequently, with only a handful of recorded transactions over the past year. The street saw four sales across detached, semi-detached, and townhouse stock, reflecting limited resale activity typical of younger or smaller residential pockets. Without sufficient volume to establish a price range or typical price for the street itself, buyer interest appears measured; currently no listings are active on Sherwood. Days on market for the recent period averaged around 89 days, suggesting moderate pace for cleared units once they appear.
The composition tilts toward townhouses, which represent half the street's recent sales activity. Comparable townhouse units across the Dempsey neighbourhood typically trade around $755,000, having softened modestly year-over-year. That broader neighbourhood context provides the closest market read: townhouses in the area are selling near ask (around 99 cents on the dollar), indicating balanced buyer-seller conditions despite the slight annual easing. For prospective buyers on Sherwood, the neighbourhood comparable offers the most grounded sense of typical pricing and competitive stance, given the street's thin local history.
Across Dempsey, comparable townhouse homes have traded at a typical price around $755,000 over the past year. The sample reflects 149 sales, providing a robust foundation for neighbourhood-level observation. Year-over-year, values have softened modestly, with the typical price easing approximately 5 percent from the prior year. Buyer-seller balance remains close to equilibrium, with homes selling near asking price (around 99 cents on the dollar), indicating neither steep discounting nor aggressive bidding pressure. Neighbourhood-wide pace runs slightly faster than Sherwood's own recent DOM, with comparable townhouses typically clearing in around 74 days.
Sherwood Road sits in Milton's Dempsey neighbourhood, a position that makes the 401 the primary artery for most daily trips. The on-ramp at Regional Road 25 is a four-minute drive, putting Mississauga within 22 minutes and Pearson within 32. For the Toronto commute, the Milton GO station is a ten-minute drive; the full trip to Union runs around 70 minutes, a rhythm that suits those who can trade a longer door-to-door for a productive train ride. The street itself is quiet enough that the road network handles the load without the through-traffic noise that defines busier corridors.
Public catchment draws to Chris Hadfield Public School, which sits directly on Sherwood Road itself — a walkable option for families on the street's eastern end. Other public options within a short drive include Robert Baldwin, Anne J. MacArthur, and Tiger Jeet Singh, all within five minutes. Catholic students attend Guardian Angels Elementary, a four-minute drive, or Our Lady of Fatima, five minutes away. Secondary students in the Catholic system draw to St. Francis Xavier, a six-minute drive. The concentration of schools within a tight radius makes Sherwood a practical choice for families with children at different stages.
Sherwood Road tends to suit buyers who want a quiet residential setting within reach of Milton's major commuting infrastructure. The street's mix of detached, semi-detached, and townhouse homes means it accommodates a range of household shapes — first-time buyers in the townhouses, growing families in the semis and detached. The tradeoff is clear: you accept a longer walk to the GO station and a car-dependent daily routine in exchange for a quieter street and a wider selection of home types than tighter townhouse-only pockets. Families with elementary-aged children will appreciate the direct walkability to Chris Hadfield Public School. The street's position in Dempsey also puts grocery shopping and the hospital within a five-minute drive, reducing errand time.
If you're considering alternatives in similar pockets, Wettlaufer Terrace offers detached homes trading around $1.8M, a step up in price and lot size for those who want more space and are willing to pay for it. Apple Terrace presents a mixed profile with homes around $1.6M, suiting buyers who want a similar neighbourhood feel but with a different balance of home types. Both streets sit within Dempsey, so the same school catchments and commute patterns apply. The choice comes down to budget and whether a larger lot or a different home configuration matters more than the specific block.
Semi inventory on Sherwood Road has seen 1 closed sales recently. Details below.
Townhouse inventory on Sherwood Road has seen 2 closed sales recently. Details below.
Sale activity on Sherwood Road in the recent period. Stats reflect closed transactions only.
| Date | Address | Beds | Sold | vs Ask | DOM | Listing brokerage |
|---|---|---|---|---|---|---|
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A thoughtful conversation grounded in every sale we have tracked on Sherwood Road.
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