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155 Gloucester Avenue — Photo 11 / 47

$10,750,000

155 Gloucester Avenue

1013 - OO Old Oakville · Detached

5

Beds

8

Baths

5000 +

Sqft

9

Parking

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.

Property

TypeDetached
Community1013 - OO Old Oakville
MunicipalityOakville
ListedMay 26, 2026
StatusCancelled
MLS#W13176888

Inside

Bedrooms5
Bathrooms8

Building

Size5000 + sqft

Parking

Total Parking9

Room Sizes

Main Level

Foyer15.0' x 10.1'
Kitchen23.8' x 19.6'
Breakfast12.0' x 12.0'
Living Room19.2' x 14.9'
Dining Room17.8' x 15.0'
Family Room25.9' x 20.7'
Den15.0' x 14.9'
Office13.3' x 12.2'

Upper Level

Primary Bedroom18.2' x 17.7'
Sitting15.0' x 14.9'
Bedroom 217.8' x 15.0'
Bedroom 316.9' x 14.9'
Bedroom 413.0' x 12.0'
Bedroom 513.4' x 11.8'

Basement

Recreation27.1' x 25.2'
Game Room21.5' x 19.1'
Exercise Room54.0' x 10.2'
Other11.3' x 11.0'
Other14.9' x 14.5'
Utility Room30.2' x 16.5'
Other9.9' x 7.0'
Cold Room/Cantina9.7' x 9.1'

Sale History

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Area Stats

1013 - OO Old Oakville · Last 90 days

Sales

$2,375,000

Median Price

52

Avg DOM

48

Sold

Leases

$3,300

Median Rent

23

Avg DOM

22

Leased

Listed by CENTURY 21 MILLER REAL ESTATE LTD.

Quick details

Price$10,750,000
TypeDetached
TransactionFor Sale
StatusCancelled
MLS#W13176888
Beds5
Baths8
Size5000 + sqft

Zoned Schools

Elementary

Secondary