Miltonly/Streets/Highside Drive
Street Profile · Old Milton · Milton, ON

Highside Drive

A street in Milton Ontario.

Detached
Housing mix
$1.05M
Typical price
across 8 sales in the last ~2 years
4
Transactions tracked
sales + leases · last 12 months
0
Active right now
live listings · today
Recent sales · last 12 monthsDetached3sample too small
Sales tracked
3
last 12 months
Typical sold
$1.05M
across 8 sales in the last ~2 years
Detached sold
3
3 sales · last 12 months
Activity
1
sales · last 90 days
Active right now
0
live listings · today
Leases
1
closed · last 12 months

Highside Drive at a glance

The street runs north-south between Martin Street and Wettlaufer Terrace, framed by mature trees and established homes. The street feels settled, with a quiet residential rhythm that reflects its central location. It is a street where the town's older character remains visible in the lot sizes and the spacing between houses.

Own on Highside? Typical is $1.05M.
Value my home

The homes here

Highside Drive is lined with detached homes, the dominant type on the street. The houses date from an earlier era of Milton's growth, with generous lot sizes that are less common in newer subdivisions. The street's housing stock is consistent in form but varied in detail, reflecting the individual choices of original owners.

Exterior treatments range from full brick to brick-and-vinyl combinations. Many homes have attached garages and private driveways.

What's nearby

Robert Baldwin Public School sits at the street's edge, making it a practical choice for families with elementary-aged children.

The market right now

Highside Drive trades rarely, with only a handful of recorded transactions over the past year. The street is composed almost entirely of detached homes, a property type that commands substantial prices in Old Milton.

The absence of published price ranges reflects the thinness of the trade record, and suitability is evaluated elsewhere on the page through neighbourhood context. Highside's own transaction record is too limited to establish price direction, but the broader neighbourhood pattern suggests measured conditions and realistic seller expectations.

Getting around

The street itself is quiet, with through-traffic routed to larger arterials, so the road network handles the load without noise.

The market

Recent activity on Highside

Sales

Stats reflect closed transactions only.

Recent sales · last 90 days
1
Typical sold · last ~2 years
$1.05M
Days on market · last 12 months

Leases

Rental activity on Highside Drive across recent months. Breakdown by bed count below.

Recent leases · last 12 months
1
Typical rent
Days on market · last 12 months
Recent closed sales, Highside Drive
DateAddressBedsSoldvs AskDOMListing brokerage
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TREB VOW · Registered access
See every closed sale on Highside Drive
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Freehold vs. condo — see them side by side
Live Milton prices, fees, and the three trades laid out plainly to help you decide.
Freehold ~$1.13MvsCondo ~$569K
Compare freehold vs condo
Getting around

Commute & reach from Highside

Transit & highways
Milton GO, 401, and major routes
Milton GO Station4 min drive · 17 min walk
Highway 401 on-ramp5 min drive
Union Station (GO)58 min transit
Schools
Public and Catholic boards
Chris Hadfield PS8 min drive
Anne J. MacArthur PS5 min drive
Irma Coulson PS6 min drive
E.W. Foster PS5 min drive
Tiger Jeet Singh PS4 min drive
Health
Hospital and nearby care
Milton District Hospital3 min drive
Parks & recreation
Trails, pools, and conservation areas
Kelso Conservation Area12 min drive
Rattlesnake Point Conservation20 min drive
Shopping & groceries
Plazas, grocers, and big-box
Walmart Milton3 min drive
Canadian Superstore8 min drive
FreshCo Milton3 min drive
Places of worship
Mosques, churches, gurdwaras
Halton Islamic Community Centre13 min drive
Milton Muslim Community Centre3 min drive
Islamic Community Centre of Milton8 min drive
Common questions

About Highside

What kinds of homes are on Highside Drive?
The street is exclusively detached homes, typical of the established Old Milton neighbourhood.
If Highside Drive isn't the right fit, what similar streets should I look at?
Wettlaufer Terrace offers detached homes at a higher price point, while Martin Street provides a more mixed stock at a lower entry price. Both are in Old Milton, so the neighbourhood feel is similar.
Your move on Highside

Selling on Highside

A thoughtful conversation grounded in every sale we have tracked on Highside Drive.

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Buying on Highside

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