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Detached for sale at 415 Highside Drive, Milton - 6 bedroom, 4 bathroom - Photo 1 of 50
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$1,350,000

415 Highside Dr

Milton, ON L9T 1W9

415 Highside Dr, MiltonListed at $1,350,000. 6 bedroom, 4 bathroom 2-Storey. MLS® W13556930.

Just listed — 1 day ago
6Beds
4Baths
2000-2500sqft
2-Storey
8Parking
$6,938 (2025)

What's this home worth?

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Description

Rare 93 x 181 ft lot (0.34 acres), approx. 50% larger than many premium downtown parcels. Mature trees, wide frontage, and depth you feel immediately. Quiet, tree-lined street with low traffic and long-term neighbours. Walk to downtown, Mill Pond, shops, and local amenities. Tucked away feel with access to the core. Georgian-style home with full-width front porch. Approx. 2,174 sq.ft. plus 2-bedroom in-law suite with separate entrance. 4 bedrooms up, 2 down. Multiple entrances offer flexibility for extended family. Functional layout with separate living, dining, and family rooms. Large family room with exposed beams and fireplace. Space to spread out with privacy throughout. Backyard is a standout. Deep, private, and usable. Room for play, entertaining, skating rink potential, and quiet sitting areas. Mature trees, open space, and regular wildlife make it feel like your own park. Heated shed with electricity ideal for workshop or office. Parking for 6 in driveway plus oversized double garage. Custom built in 1967 and well maintained. For those with a bigger vision, zoning allows potential for a custom home up to approx. 6,000 sq.ft. with a 3-car garage. Enjoy it as-is, update over time, or build new. One of Milton's most unique properties.

Property Details

Property TypeDetached
Style2-Storey
Community1035 - OM Old Milton
Rooms8+4
Kitchens2
Washrooms4
Square Feet2000-2500 sqft
Lot Dimensions92.72 × 181.02 ft
Fronting OnWest
Dir/Cross StOntario St N & Steeles Ave E
Garage TypeAttached
Garage Parking Spaces2
DrivePrivate Double
Parking Drive Spaces6
Total Parking Spaces8
ExteriorBrick
RoofAsphalt Shingle
FoundationUnknown
BasementFull, Finished
Fireplace FeaturesYes
Heating TypeRadiant
Heating SourceGas
A/CWall Unit(s)
SewersSewer
Taxes (2025)$6,938
HSTNot Subject to HST
Other StructuresGarden Shed
UFFINo
Listed Date7/13/2026
Days on Market1 days
Possession60/90 days/TBA

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REALTOR® · RE/MAX Realtron Realty Inc.

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Listing Courtesy of: ROYAL LEPAGE MEADOWTOWNE REALTY

MLS® #W13556930

TRREBMLS®

The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing data is deemed reliable but is not guaranteed accurate by TRREB. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.

© 2026 Toronto Regional Real Estate Board. All rights reserved.

HouseIndex Take: 415 Highside Drive

This detached (2-Storey) is located in the 1035 - OM Old Milton neighbourhood of Milton.

The home offers 6+2 bedrooms, 4 bathrooms.

Features include a full, finished basement, 8 parking spaces including a 2-car garage, a fireplace.

Additional details: lot dimensions of 92.72 × 181.02 feet.

Listed at $1,350,000 CAD with annual property taxes of $6,938 (2025).

About Milton Real Estate

This Detached is located in the 1035 - OM Old Milton community in Milton. Milton is one of Canada's fastest-growing towns, nestled against the Niagara Escarpment in Halton Region. New master-planned communities offer modern homes at competitive prices, while the historic downtown retains small-town character. Milton GO provides commuter access, and the escarpment trails are a draw for outdoor enthusiasts. Detached homes in Milton are in high demand among families seeking space, privacy, and long-term equity growth.

Niagara Escarpment trailsMilton GO stationRapidly growing new communitiesHalton District School Board
~55 min commute to downtown TorontoWalkability: Car-oriented — walkable historic downtown