Highside Drive is a residential street in Old Milton, the historic core of the town, where the grid tightens and the streets run shorter than they do in the newer subdivisions to the south and west.
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Updated September 13, 2026. Listings live.
Highside Drive is a residential street in Old Milton, the historic core of the town, where the grid tightens and the streets run shorter than they do in the newer subdivisions to the south and west. Old Milton frames the address on every side, with the town's older institutional and commercial spine close by.
Highside Drive is a detached street. Every home recorded here is a detached house, and no semi, townhouse, or condo stock appears in the mix. That single-type profile is unusual for Milton, where most streets carry at least two forms, and it gives Highside a consistent built character from end to end.
Highside Drive sits in Old Milton, a position that makes the car the practical instrument for most of the week's movements. Nothing here is remote; the distances simply favour the highway over the platform.
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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 49 civic addresses on Highside Drive, numbered 320–444, with Mountainview Drive, Elm Avenue and Ridge Drive 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 Highside Drive is listed for sale. Nothing else, and no account.
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