miltonly.
Miltonly›Buy›Old Milton›415 Highside Drive
415 Highside Drive, Milton, on L9t 1w9
FOR SALE9d on market

$1,475,000

$656/sqft

6 bd · 4 ba · Detached · 2,250 sqft

415 Highside Drive, Milton, on L9t 1w9

👁 16 people viewed today
🎥 Take the 3D tour →
🏠

Detached

2-Storey

🚗

8 parking

Attached

📋

$6,938/yr

Tax (2025)

Listed 9 days ago · Source: TREB MLS® W13070264 · Royal Lepage Meadowtowne Realty · Near Ontario St N & Steeles Ave E

About this home

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.

Features

Auto Garage Door RemotePorch🔥 FireplaceBasement

Property details

Parking & Garage

Parking spaces8
GarageAttached

Heating & Cooling

Heat typeRadiant
Heat sourceGas
CoolingWall Unit(s)

Building

Style2-Storey
ConstructionBrick
RoofAsphalt Shingle
FoundationUnknown
FacesWest

Lot

Lot size92.72' × 181.02'
SewerSewer

What's nearby

🏙️
Downtown Toronto

~55 min drive from Milton

Directions →
🛍️
Square One

~25 min drive from Milton

Directions →
✈️
Pearson Airport

~35 min drive from Milton

Directions →
🚉
Bronte GO

~20 min drive from Milton

Directions →
🚉
Trafalgar GO

~22 min drive from Milton

Directions →
🛍️
Oakville Place

~24 min drive from Milton

Directions →
🎓
Sheridan College

~30 min drive from Milton

Directions →
🏥
Milton Hospital

~8 min drive from Milton

Directions →

Mortgage & monthly cost

$7,976/month estimated total

Mortgage

$6,898

Tax

$578

Maintenance

$350

Insurance

$150

Estimated Ontario Land Transfer Tax$25,975

Estimates only. Call Aamir for a full cost breakdown and pre-approval guidance.

Investment analysis

Est. monthly rent

$2,581

Gross cap rate

2.1%

Monthly cashflow

$-7,147

Negative cashflow reflects current mortgage rates. Contact Aamir for a full investment strategy — down-payment sizing, rate-shopping, and Milton-specific rental benchmarks can all move this number.

Assumes 20% down · 5% rate · 25-yr amortization · $300/mo maintenance · est. rent from live Milton rental data. Estimates only — contact Aamir for a full investment analysis.

Milton homeowner?

Own a similar home in Milton?

Get a free valuation in 24 hours — see what a home like this could list for today.

Quick facts

MLS®W13070264
Statusactive
TypeDetached
Listed9 days ago
BrokerageRoyal Lepage Meadowtowne Realty
FacesWest
Cross streetOntario St N & Steeles Ave E
Annual tax$6,938

Aamir Yaqoob

Sales Representative · RE/MAX Realty Specialists Inc.

Have questions about this property?

With 14 years of full-time experience, Aamir knows that real estate is about far more than price — it is about finding the right fit, the right protection, and the right outcome. Whether you are a tenant, a landlord, or ready to buy or sell, Aamir represents your interests completely.

🏆 RE/MAX Hall of Fame Award
🏆 RE/MAX Executive Award
🏆 RE/MAX 100% Club Award
14 Years Full-TimeTenants & LandlordsBuyers & SellersMilton Specialist
gtahomequest@gmail.com

Data provided by TREB via Miltonly. MLS® W13070264. Information deemed reliable but not guaranteed. Updated daily.

$1,475,000

📞