Roper Drive sits in the Dempsey neighbourhood of Milton, a residential street that runs quietly through a landscape of detached homes.
Updated September 5, 2026. Sales and leases from the Board’s closed records; listings live.
Roper Drive hasn't had enough recent sales to publish its own typical price, and we won't publish a price the record can't support. The Dempsey typical above is the honest anchor until it does.
Roper Drive sits in the Dempsey neighbourhood of Milton, a residential street that runs quietly through a landscape of detached homes. Roper Drive is not a destination street; it is a place where daily life unfolds at a measured pace, close to the essentials yet removed from the busier arteries.
Roper Drive is a detached-home street. For buyers seeking a detached home in a settled Milton pocket, the street offers a consistent product in a quiet setting.
Roper Drive trades rarely, with only a handful of detached homes changing hands over the past year. Buyers considering this street will find little recent activity to benchmark against, and the absence of current listings suggests a market that moves slowly, with properties appearing sporadically rather than in waves.
Prices have held steady over the past year, with no clear directional shift. Buyers have been paying close to asking, with sold prices averaging just under the list price, indicating a balanced market where negotiation room is modest.
Secondary options sit farther out, though the closest are within a reasonable drive. Families should confirm current school assignment directly with the boards.
For those weighing proximity to specific schools or parks, the nearby options in Dempsey itself already cover most needs. The choice often comes down to how much premium the street's particular setting justifies.
Stats reflect closed transactions only.
| Date | Address | Beds | Sold | vs Ask | DOM | Listing brokerage |
|---|
The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale or lease of real estate and may not be used for any commercial purpose or any other purpose. The information is deemed reliable but is not guaranteed accurate by PropTx.
The Town records 68 civic addresses on Roper Drive, numbered 1253–1356, with Knight Trail, Cooke Crescent and Maple Avenue 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 Roper Drive is listed for sale. Nothing else, and no account.
Watch Roper Drive →Few recent sales on Roper Drive means less to compare against, which is exactly when pricing needs judgement rather than a formula. A conversation grounded in what the record does show, and in the Roper Drive homes we've tracked.
Request a valuation →Too few recent sales on Roper Drive to publish a typical price yet, the record's there, it just can't support a number. Get an email when the next home here is listed for sale.