Waters Boulevard is a residential street in Milton's Dempsey district, a pocket of the town that sits north of the downtown core and east of the escarpment line.
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Updated September 11, 2026. Listings live.
Waters Boulevard is a residential street in Milton's Dempsey district, a pocket of the town that sits north of the downtown core and east of the escarpment line. Dempsey is largely built out, so the street's frame is settled rather than changing: established parks, schools, and a grid of residential blocks that connect toward the commercial corridors along Steeles and Derry.
Housing on Waters Boulevard is a mix of semi-detached and townhouse forms, with townhouses holding the slight majority of the street's recent activity. Both types are represented in small numbers, so the street reads as a compact, low-rise pocket rather than a uniform run of one product.
Waters Boulevard sits in Dempsey, a position that makes the GO train the realistic Toronto commute. The street's real advantage is that it does not force a choice between the two modes; both are within easy reach.
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The Town records 58 civic addresses on Waters Boulevard, numbered 91–170, with Featherstone Road and Weller Crossing 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 Waters Boulevard is listed for sale. Nothing else, and no account.
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