Dempsey
Milton Real Estate
Housing stock in Dempsey: New-build detached (2005–2020s) on former farmland. CREA's townhouse benchmark for the Oakville Milton region covering Milton is $702,800 (May 2026) — the index is published per board, not per neighbourhood.
Living in Dempsey
Architectural era · New-build detached (2005–2020s) on former farmland
Dempsey is one of Milton's original 2000s-era master-planned subdivisions, developed as Milton transitioned from a small town of 32,000 (2001) to a 130,000+ population commuter city by the 2020s — the fastest per-capita growth in Canada during that period. Housing stock is nearly entirely new-build detached and townhouse.
Thinking about Dempsey?
A licensed Milton advisor will reach out to walk you through your options.
Who buys here
First-time buyers, young families priced out of Oakville and Mississauga, and Milton GO commuters.
On neighbourhood pricing: CREA publishes the MLS® Home Price Index per real estate board, not per neighbourhood, and IndiBrick does not currently license an MLS® feed — so we publish no median price, inventory count or days-on-market for Dempsey specifically. For regional context, the Oakville Milton townhouse benchmark is $702,800 as of the May 2026 release. A licensed advisor can pull current Dempsey listings and recent comparables from the MLS® on request.
Browse Milton inventory by type + price.
Dempsey FAQ
What is Dempsey in Milton known for?
Dempsey is one of Milton's original 2000s-era master-planned subdivisions, developed as Milton transitioned from a small town of 32,000 (2001) to a 130,000+ population commuter city by the 2020s — the fastest per-capita growth in Canada during that period. Housing stock is nearly entirely new-build detached and townhouse.
What kind of homes are in Dempsey?
Dempsey's housing stock is predominantly new-build detached (2005–2020s) on former farmland. Buyers here are typically first-time buyers, young families priced out of Oakville and Mississauga, and Milton GO commuters.
What do homes cost around Dempsey?
CREA publishes the MLS® Home Price Index at the real estate board level, not per neighbourhood, so there is no published benchmark specific to Dempsey. The townhouse benchmark for the Oakville Milton reporting region that covers Milton is $702,800 as of the May 2026 release. Neighbourhood-level pricing varies substantially within any city — a licensed advisor can pull current Dempsey inventory and recent comparables from the MLS® for you.
Talk to a Milton advisor about Dempsey.
A licensed Milton advisor will reach out to walk you through active Dempsey listings, current prices, and your financing options.
Dempsey, Milton
Milton · Licensed FSRA advisor