Sherwood Road runs through the Dempsey neighbourhood in Milton's north end.
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Updated September 5, 2026. Listings live.
Sherwood Road runs through the Dempsey neighbourhood in Milton's north end. It is a quiet residential street, with a mix of detached homes and townhouses set along a tree-lined route. Nearby parks, including Sinclair Park just a minute away on foot, give the area a green, open feel. Sherwood Road is a settled, unassuming part of Milton, where daily life moves at an easy pace.
Sherwood Road holds a modest collection of homes, with townhouses making up the majority of the stock. Detached houses appear as well, though in smaller number.
Outdoor space is plentiful. Several elementary schools, including E.W. Foster and Irma Coulson, are nearby, as are Catholic options like Guardian Angels and Bishop Reding.
| Date | Address | Beds | Sold | vs Ask | DOM | Listing brokerage |
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The Town records 93 civic addresses on Sherwood Road, numbered 165–288, with Livingston Road, Sinclair Boulevard and Alexander Crescent meeting it in that order from the low-number end.
Civic addresses from the Town of Milton under the Open Government Licence. Positions approximate. No sale price or date is shown for any single address.
A written valuation prepared by hand from comparable sales, sent by email. Nothing on this page estimates a single address.
See what it’s worth →An email when a home on Sherwood Road is listed for sale. Nothing else, and no account.
Watch Sherwood Road →A private conversation about your home on Sherwood Road and what is listed around it, before you decide anything.
Request a valuation →An email when a home on Sherwood Road is listed for sale. Nothing else, and no account.