Waters Boulevard runs through the Dempsey neighbourhood in northeast Milton, a corridor of newer construction that reflects the area's steady outward expansion.
Waters Boulevard runs through the Dempsey neighbourhood in northeast Milton, a corridor of newer construction that reflects the area's steady outward expansion. The street sits a short drive from the 401, with Milton District Hospital and several grocery anchors within five minutes by car. Sidewalks line both sides, and the lots are uniformly sized, giving the street a consistent, planned feel. Chris Hadfield Public School sits right at the corner, anchoring the block with a daily rhythm of drop-offs and pickups. This is a street built for families, with wide roads and a quiet, residential character that remains close to the city's major arteries.
Homes on Waters Boulevard are a mix of semis and townhouses, all built within the last decade. The semis offer two storeys with attached garages, typically three bedrooms and two and a half bathrooms. The townhouses follow a similar footprint, with brick and stone exteriors and private driveways. Lot sizes are consistent, with shallow front yards and deeper rear yards that back onto laneways or green space. The street's housing stock is uniform in era and scale, with no single detached homes breaking the roofline.
The architecture leans toward modern suburban: open-concept main floors, laminate and hardwood finishes, and kitchens with granite or quartz counters. Many homes have finished basements, adding living space without altering the street's tidy exterior. Exterior colours are restrained, with beige, grey, and cream brick dominating. The semis and townhouses share similar square footage, typically between 1,400 and 1,600 square feet above grade. Across the Dempsey area, semis of this vintage trade around $870,000, reflecting the neighbourhood's steady demand for entry-level family housing.
Waters Boulevard sits within a five-minute drive of several grocery options, including Walmart, FreshCo, and Sobeys. Milton District Hospital is also five minutes away by car. For daily errands, the strip plazas along Derry Road and Thompson Road cover most needs. Chris Hadfield Public School is at the street's edge, making the morning walk a matter of steps rather than minutes.
Parks are a short drive away. Coates Park and Velodrome Park are each six minutes by car, offering sports fields and playgrounds. Milton Community Park is walkable at eleven minutes, with a splash pad and walking trails. The Milton GO Station is ten minutes by car, and Highway 401 is four minutes from the street's northern end. For weekend outings, Kelso Conservation Area is ten minutes away, with hiking and skiing in season.
Waters Boulevard trades rarely, with only a handful of recorded transactions over the past year. The street's mix of semis and townhouses, set in the Dempsey neighbourhood, attracts buyers drawn to a quieter residential corridor with strong school access and convenient highway proximity. The limited activity means the street's price range is not publicly reportable, but the surrounding area provides useful context. Comparable semis across Dempsey have traded around $869,000 over the past year, with a slight softening in values year over year. Days on market average around 72, and sales have generally closed at or near asking price, suggesting balanced conditions. For buyers who value the street's specific character and location, the thin trade record is less a limitation than a reflection of its niche appeal.
Across 1029 - DE Dempsey, comparable semi-detached homes have sold at broadly similar levels. The typical sold price sits around $869,000, drawn from a substantial sample of recent trades. Values have eased back modestly over the past year, while the sold-to-ask ratio near 1.0 indicates that buyers are generally paying at or close to list price. Neighbourhood-wide pace runs slightly faster than the street's own days on market, with comparable homes typically clearing in around 72 days.
Waters Boulevard sits in Dempsey, a pocket where the 401 on-ramp at Regional Road 25 is a four-minute drive, making Mississauga a 22-minute run and Pearson reachable in just over half an hour. The Milton GO Station is ten minutes by car, which puts Union Station at about 70 minutes total with the walk to the platform. The street itself is quiet enough that the road network handles the load without the through-traffic noise that defines busier corridors.
Public elementary catchment falls to Chris Hadfield Public School, which sits directly on the street, making it walkable for families at the north end. Other nearby public options include Robert Baldwin and Anne J. MacArthur, both within a five-minute drive. Catholic students draw to Guardian Angels Catholic Elementary, four minutes away, with St. Francis Xavier Catholic Secondary School serving the high school years at a six-minute drive.
Waters Boulevard suits buyers who want a newer Dempsey address with quick highway access and a walkable elementary school. The stock here is semi-detached and townhouse, which tends to draw first-time buyers and young families who prioritize commute efficiency over lot size. The tradeoff is proximity to the 401 corridor rather than a walkable downtown core. Those who value a short drive to grocery and the hospital will find the street practical, while those seeking larger detached homes or older character will look elsewhere.
If you are considering alternatives in similar pockets, Wettlaufer Terrace offers detached homes trading around $1.8M, a step up in space and price for those who want more square footage. Apple Terrace presents a mixed profile with homes around $1.6M, suiting buyers who want a wider range of property types. Both are within Dempsey, so the commute and school catchment remain similar, but the price point and lot characteristics shift meaningfully.
Semi inventory on Waters Boulevard has seen 1 closed sales recently. Details below.
Townhouse inventory on Waters Boulevard has seen 1 closed sales recently. Details below.
Sale activity on Waters Boulevard in the recent period. Stats reflect closed transactions only.
| Date | Address | Beds | Sold | vs Ask | DOM | Listing brokerage |
|---|---|---|---|---|---|---|
| Loading sold records… | ||||||
A thoughtful conversation grounded in every sale we have tracked on Waters Boulevard.
Request a valuation →