415 Highside Drive, Milton

Over 1/3 Acre in the Heart of Milton!

Set on a 93 x 181 ft lot (0.34 acres), this is one of those properties that rarely comes to market.

Mature trees, wide frontage, and a depth that completely changes how you use your outdoor space.

It is roughly 50% larger than many of the premium downtown lots that draw attention, and you feel it the moment you arrive.

The home sits proudly on a quiet, tree-lined street known for low traffic, long-term neighbours, and a true sense of community.

Multiple generations have stayed here, turnover is low, and kids still play outside.

Walk to downtown, grab an ice cream, head to Mill Pond with the dog, or make your way to local churches and amenities.

It is a 15 minute walk to the heart of Milton, but it feels tucked away.

The house itself is a classic Georgian-style design with a full-width front porch that invites you to slow down and stay awhile.

Inside, there is approximately 2,174 sq.ft. above grade, plus a two-bedroom in-law suite with a separate entrance.

Four bedrooms upstairs, two more below, offering flexibility for large families or multi-generational living.

The layout provides space where it matters. Separate living, dining, and family rooms create privacy within the home, whether you are hosting or just trying to spread out.

The family room stands out with exposed beams and a grand fireplace, a space that naturally becomes the centre of the home.

This is a house that has adapted over time.

It has worked for young kids, older kids, and everything in between. Every nook is used, and there are multiple entrances at both the front and back, making it easy to come and go without disruption.

The backyard is where this property separates itself.

It is not just large, it is usable.

Skating rink in the winter, kids jumping into piles of leaves in the fall. There are quiet corners to sit, open areas to play, and a steady presence of wildlife including baby bunnies and birds. It feels more like a private park than a typical backyard.

A heated shed with electricity offers even more flexibility, whether for a workshop, hobby space, or a dedicated home office.

Parking is handled with ease, with space for six vehicles in the driveway plus an oversized double garage.

Custom built in 1967, the home has been well cared for and thoughtfully used. And if your vision goes beyond what is here today, the lot opens the door to something even bigger.

Under current zoning, there is potential to build a custom home of up to approximately 6,000 sq.ft. with a three car garage, taking full advantage of the size and setting.

Enjoy it as it stands, evolve it over time, or start fresh and create something remarkable.

No matter what you choose, you have one of the most unique and special properties in town.

Explore 415 Highside Drive in 3D: