Gollins Drive runs through the Dempsey neighbourhood in Milton's north end.
Gollins Drive runs through the Dempsey neighbourhood in Milton's north end. It is a quiet residential street lined with townhomes, set back from the main arteries. The street sits within a grid of newer subdivisions, with Chris Hadfield Public School at its southern edge. Mature trees are still establishing themselves, giving the street a fresh, built-recently feel. The surrounding area is defined by family-oriented development, with parks and schools within a short walk.
Gollins Drive is a townhouse street. Every residence on the block is a townhome, built in the early 2000s. The units are attached in rows of three or four, with two storeys and a single-car garage. Floor plans typically offer three bedrooms and two and a half bathrooms. Exteriors are finished in brick and vinyl siding, with neutral tones dominating the palette.
The homes share a consistent architectural language: front doors set back from the street, small front lawns, and driveways that accommodate one vehicle. The builder is not attributed with high confidence, but the uniformity of design suggests a single developer. Some units have been updated with modern kitchens and hardwood flooring, while others retain original finishes. The street feels cohesive, with well-maintained properties and a tidy streetscape.
Gollins Drive is within walking distance of Chris Hadfield Public School, which sits at the street's southern end. A few minutes' drive brings you to Coates Park and Velodrome Park, both offering playgrounds and green space. Grocery shopping is a short drive away at Walmart Milton or FreshCo Milton, both about four minutes by car. Milton District Hospital is five minutes away, and Highway 401 is accessible in four minutes via Regional Road 25.
For daily errands, the Milton Muslim Community Centre is a four-minute drive. The Milton GO Station is ten minutes by car, connecting residents to Toronto in about 70 minutes. The street's position in Dempsey puts it close to several elementary schools, both public and Catholic, making it a practical choice for families.
Gollins Drive trades rarely, with only a handful of recorded transactions over the past year. The street is composed primarily of townhomes, and the limited activity makes it difficult to draw firm conclusions about pricing. Days on market average around 83 days, suggesting a measured pace when units do come up. The neighbourhood character is quiet and family-oriented, with several parks within a short drive and a strong selection of public and Catholic elementary schools within walking distance. Buyers drawn to Gollins are typically looking for a settled, low-turnover enclave in Dempsey, where the trade pattern is clearest when read against the wider neighbourhood comparable. The street's appeal lies in its privacy and consistency rather than frequent market churn.
Across 1029 - DE Dempsey, comparable townhomes have sold at broadly comparable levels. The typical sold price sits around $755,000, based on a substantial sample of 142 transactions over the past year. Prices have softened modestly year over year, easing back by roughly 4%. Buyers are paying near asking, with the sold-to-ask ratio at approximately 0.997, indicating minimal negotiation room. Neighbourhood-wide days on market average 72, slightly faster than the street's own pace, suggesting that well-priced townhomes in Dempsey move at a steady clip.
Gollins Drive sits in Dempsey, a pocket that puts the 401 on-ramp at Regional Road 25 roughly four minutes away. The Milton GO Station is a ten-minute drive, making the Toronto commute a realistic hour-plus proposition via train. For those working in Mississauga or Burlington, the drive runs around 22 and 20 minutes respectively, which draws many residents who need daily access to those corridors. The street itself is quiet, with little through-traffic, so the road network handles the load without the noise of a busier artery.
Public elementary catchment falls to Chris Hadfield Public School, which sits directly on Gollins Drive itself, a walkable option for families on the street. Catholic elementary students attend Guardian Angels Catholic Elementary School, a four-minute drive. For secondary, public students draw to Craig Kielburger Secondary School (not listed but typical for Dempsey), while Catholic students attend St. Francis Xavier Catholic Secondary School, a six-minute drive. The proximity to multiple elementary schools within a short drive makes the street practical for families with younger children.
Gollins Drive tends to suit families and couples looking for a quiet townhouse-oriented pocket in Dempsey. The stock is predominantly townhouses, which keeps entry points more accessible than the detached homes on neighbouring streets. Buyers here accept a tighter lot and attached living in exchange for proximity to the 401 and a handful of parks within a ten-minute drive. The rental segment is anchored by unfurnished long-term tenants, suggesting a stable renter base rather than transient demand. For those who prioritize walkability to schools and highway access over lot size, Gollins Drive offers a practical balance.
If a detached home on a larger lot is the priority, Wettlaufer Terrace trades around $1.8M with a different feel. For those seeking a mix of detached and townhouse options with a similar price point, Apple Terrace offers variety around $1.6M. Both are within Dempsey, so the neighbourhood context and school catchments remain similar. The tradeoff is primarily in home type and lot size rather than location or commute profile.
Townhouse inventory on Gollins Drive has seen 2 closed sales recently. Details below.
Sale activity on Gollins Drive in the recent period. Stats reflect closed transactions only.
Rental activity on Gollins Drive across recent months. Breakdown by bed count below.
| Date | Address | Beds | Sold | vs Ask | DOM | Listing brokerage |
|---|---|---|---|---|---|---|
| Loading sold records⦠| ||||||
A thoughtful conversation grounded in every sale we have tracked on Gollins Drive.
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