Sinclair Boulevard is a residential street in Milton's Dempsey neighbourhood, a district that took shape as the town pushed east of its historic core.
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Updated September 22, 2026. Listings live.
Sinclair Boulevard is a residential street in Milton's Dempsey neighbourhood, a district that took shape as the town pushed east of its historic core. Dempsey is a largely built-out part of Milton, and Sinclair Boulevard reads as one of its quieter interior streets rather than a through route. What frames the street is residential calm: parkland at one end, houses along its length, and the everyday infrastructure of a settled suburban district close at hand.
Sinclair Boulevard sits in Dempsey, a position that makes the GO station the realistic Toronto commute. Nothing about the routing is complicated; the street sits close enough to the highway spine that the usual Milton bottlenecks are largely avoided.
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The Town records 6 civic addresses on Sinclair Boulevard, numbered 37–45, with Alexander Crescent, Main Street, Featherstone Road, Sherwood Road and Hampshire Way 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.
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