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155 Gloucester Avenue, Oakville, ON L6J 3W3
155 Gloucester Avenue, Oakville, ON L6J 3W3 — photo 1
155 Gloucester Avenue, Oakville, ON L6J 3W3 — photo 2
155 Gloucester Avenue, Oakville, ON L6J 3W3 — photo 3
155 Gloucester Avenue, Oakville, ON L6J 3W3 — photo 4

$10,750,000

155 Gloucester Avenue, Oakville, ON L6J 3W3

Oakville

Bedrooms
5
Bathrooms
8
Parking
9
Type
Detached
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About this listing

Set on one of the most coveted streets in Old Oakville, this extraordinary residence offers a rare combination of landmark architecture, timeless design, and resort-inspired living on an irreplaceable 0.6-acre property. Originally designed by renowned architect Bill Hicks and built by Legend Homes, the home underwent an extensive renovation in 2021, resulting in nearly 12,000 square feet of impeccably finished living space that blends classic elegance with modern luxury. Surrounded by mature trees and lush landscaping, the home makes an unforgettable first impression with its sweeping drive, triple car garage, and striking architectural presence. Inside, beautifully scaled principal rooms, soaring ceilings, expansive windows, and refined finishes create an atmosphere equally suited for grand entertaining and everyday family living. The chef's kitchen features custom Downsview cabinetry, extensive stone surfaces, and professional-grade appliances, seamlessly connecting to the surrounding family and entertaining spaces. A dramatic extra-wide staircase leads to the second level, where each bedroom is designed as a private suite with semi-vaulted ceilings and luxurious ensuites. The primary retreat is exceptional in scale, offering a private sitting room with balcony access, a boutique-inspired dressing room with extensive custom cabinetry, and a spa-like ensuite designed for complete relaxation. The lower level is thoughtfully designed with an oversized fitness studio, temperature-controlled wine cellar, sophisticated wet bar, expansive recreation spaces, and a walk-up to the backyard. Outdoors, the resort-like setting was refreshed in 2025 and features a gunite pool, winter-operational hot tub, extensive natural stone patios, and a fully equipped outdoor kitchen beneath the mature tree canopy. Located just moments from the lake, downtown Oakville, top-ranked schools, and parks. This home represents one of the finest luxury offerings to come to market in Old Oakville.

Walkability

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Walkability, transit, and bike-friendliness for 155 Gloucester Avenue, Oakville, ON L6J 3W3

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MLS# W13176888

Listed by CENTURY 21 MILLER REAL ESTATE LTD.

On market since May 26, 2026

About 155 Gloucester Avenue, Oakville, ON L6J 3W3

How much is 155 Gloucester Avenue, Oakville, ON L6J 3W3?

155 Gloucester Avenue, Oakville, ON L6J 3W3 is listed for $10,750,000 CAD.

How many bedrooms and bathrooms does 155 Gloucester Avenue, Oakville, ON L6J 3W3 have?

155 Gloucester Avenue, Oakville, ON L6J 3W3 has 5 bedrooms and 8 bathrooms.

What type of property is 155 Gloucester Avenue, Oakville, ON L6J 3W3?

155 Gloucester Avenue, Oakville, ON L6J 3W3 is a Detached.

What neighbourhood is 155 Gloucester Avenue, Oakville, ON L6J 3W3 in?

155 Gloucester Avenue, Oakville, ON L6J 3W3 is in Oakville, Ontario.

Is 155 Gloucester Avenue, Oakville, ON L6J 3W3 for sale or for rent?

155 Gloucester Avenue, Oakville, ON L6J 3W3 is currently for sale.

How do I book a showing for 155 Gloucester Avenue, Oakville, ON L6J 3W3?

Contact Michael Mezheritsky to arrange a private showing of 155 Gloucester Avenue, Oakville, ON L6J 3W3 (MLS# W13176888). You can also send a message through the contact form on this site.