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.
Address
155 Gloucester Avenue
List Price
$10,750,000
MLS® Status
New
Property Type
Residential Freehold
Type of Dwelling
Detached
Style of Home
2-Storey
Transaction Type
Sale
Area
Oakville
Sub-Area
1013 - OO Old Oakville
Region
Halton
Bedrooms
5
Bedrooms (Total)
5
Rooms Above Grade
16
Rooms Below Grade
10
Bathrooms
8
Floor Area
5000 + Sq. Ft.
Lot Size Source
GeoWarehouse
Lot Depth
187.5
Lot Shape
Rectangular
Lot Irregularities
149.89' x 187.50' x 151.06' x 186.61'
Lot Size Range (Acres)
.50 - 1.99
Lot Size Units
Feet
Lot Width
149.89
Parcel Number
248100007
Occupant Type
Owner
Cross Street
Lakeshore Road E/Gloucester Ave
Approx. Age
16 - 30 Years
MLS® Number
W13176888
Listing Brokerage
CENTURY 21 MILLER REAL ESTATE LTD.
Basement Area
Full, Walk-Up, Finished
Postal Code
L6J 3W3
Posession Details
TBD
Parking
Private Triple
Parking Places (Total)
9
Parking Spaces
6
Tax Amount
$46,602.00
Tax Year
2026
Site Influences
Built-In-BBQ, Hot Tub, Lake/Pond, Landscape Lighting, Landscaped, Lawn Sprinkler System, Library, Lighting, Marina, Park, Patio, Privacy, Rec./Commun.Centre, School
Exterior Features
Built-In-BBQ, Hot Tub, Landscape Lighting, Landscaped, Lawn Sprinkler System, Lighting, Patio, Privacy
Interior Features
Auto Garage Door Remote, Built-In Oven, Separate Heating Controls
Property Features
Lake/Pond, Library, Marina, Park, Rec./Commun.Centre, School
Central Vacuum
No
Family Room
Yes
Elevator
No
Ensuite Laundry
No
Special Designation
Unknown
Standard Status
Active
Board Or Association
Toronto Regional Real Estate Board
Heat Source
Gas
Heat Type
Forced Air
Cooling Features
Central Air
Construction Materials
Stone, Wood
Direction Faces
East
Fireplace
Yes
Fireplace Features
Family Room, Living Room, Natural Gas
Foundation Details
Poured Concrete
Garage
Yes
Garage Type
Attached
Covered Spaces
3
Kitchens Total
1
Kitchens Above Grade
1
Other Structures
Garden Shed
Pool Features
Inground, Salt
Roof
Asphalt Shingle
Tax Legal Description
PT LT 11, CON 3 TRAFALGAR, SOUTH OF DUNDAS STREET , AS IN 57162 ; NOW KNOWN AS ; LT 6, PL 1009 ; OAKVILLE
Security Features
Alarm System
Topography
Flat
View Type
Trees/Woods
Waterfront
No
Sewer
Sewer
Rooms
| Floor | Type | Dimensions | Features |
|---|---|---|---|
| Main | Foyer | 4.57 x 3.07 | |
| Main | Kitchen | 7.24 x 5.97 | |
| Main | Breakfast | 3.66 x 3.66 | |
| Main | Living Room | 5.84 x 4.55 | |
| Main | Dining Room | 5.44 x 4.57 | |
| Main | Family Room | 7.9 x 6.3 | |
| Main | Den | 4.57 x 4.55 | |
| Main | Office | 4.06 x 3.73 | |
| Second | Primary Bedroom | 5.56 x 5.38 | |
| Second | Sitting | 4.57 x 4.55 | |
| Second | Bedroom 2 | 5.44 x 4.57 | |
| Second | Bedroom 3 | 5.16 x 4.55 | |
| Second | Bedroom 4 | 3.96 x 3.66 | |
| Second | Bedroom 5 | 4.09 x 3.61 | |
| Basement | Recreation | 8.25 x 7.67 | |
| Basement | Game Room | 6.55 x 5.82 | |
| Basement | Exercise Room | 16.46 x 3.12 | |
| Basement | Other | 3.43 x 3.35 | |
| Basement | Other | 4.55 x 4.42 | |
| Basement | Utility Room | 9.19 x 5.03 | |
| Basement | Other | 3.02 x 2.13 | |
| Basement | Cold Room/Cantina | 2.97 x 2.77 |