| 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. |
| Price | $10,750,000 |
| Taxes: | $46602.00 |
| Occupancy: | Owner |
| Address: | 155 Gloucester Avenue , Oakville, L6J 3W3, Halton |
| Acreage: | .50-1.99 |
| Directions/Cross Streets: | Lakeshore Road E/Gloucester Ave |
| Rooms: | 16 |
| Rooms +: | 10 |
| Bedrooms: | 5 |
| Bedrooms +: | 0 |
| Family Room: | T |
| Basement: | Full, Walk-Up |
| Level/Floor | Room | Length(m) | Width(m) | Descriptions | |
| Room 1 | Main | Foyer | 4.57 | 3.07 | |
| Room 2 | Main | Kitchen | 7.24 | 5.97 | |
| Room 3 | Main | Breakfast | 3.66 | 3.66 | |
| Room 4 | Main | Living Ro | 5.84 | 4.55 | |
| Room 5 | Main | Dining Ro | 5.44 | 4.57 | |
| Room 6 | Main | Family Ro | 7.9 | 6.3 | |
| Room 7 | Main | Den | 4.57 | 4.55 | |
| Room 8 | Main | Office | 4.06 | 3.73 | |
| Room 9 | Second | Primary B | 5.56 | 5.38 | |
| Room 10 | Second | Sitting | 4.57 | 4.55 | |
| Room 11 | Second | Bedroom 2 | 5.44 | 4.57 | |
| Room 12 | Second | Bedroom 3 | 5.16 | 4.55 | |
| Room 13 | Second | Bedroom 4 | 3.96 | 3.66 | |
| Room 14 | Second | Bedroom 5 | 4.09 | 3.61 | |
| Room 15 | Basement | Recreatio | 8.25 | 7.67 |
| Washroom Type | No. of Pieces | Level |
| Washroom Type 1 | 2 | Main |
| Washroom Type 2 | 3 | Second |
| Washroom Type 3 | 5 | Second |
| Washroom Type 4 | 3 | Basement |
| Washroom Type 5 | 0 | |
| Washroom Type 6 | 2 | Main |
| Washroom Type 7 | 3 | Second |
| Washroom Type 8 | 5 | Second |
| Washroom Type 9 | 3 | Basement |
| Washroom Type 10 | 0 |
| Total Area: | 0.00 |
| Approximatly Age: | 16-30 |
| Property Type: | Detached |
| Style: | 2-Storey |
| Exterior: | Stone, Wood |
| Garage Type: | Attached |
| (Parking/)Drive: | Private Tr |
| Drive Parking Spaces: | 6 |
| Park #1 | |
| Parking Type: | Private Tr |
| Park #2 | |
| Parking Type: | Private Tr |
| Pool: | Inground |
| Other Structures: | Garden Shed |
| Approximatly Age: | 16-30 |
| Approximatly Square Footage: | 5000 + |
| Property Features: | Lake/Pond, Library |
| CAC Included: | N |
| Water Included: | N |
| Cabel TV Included: | N |
| Common Elements Included: | N |
| Heat Included: | N |
| Parking Included: | N |
| Condo Tax Included: | N |
| Building Insurance Included: | N |
| Fireplace/Stove: | Y |
| Heat Type: | Forced Air |
| Central Air Conditioning: | Central Air |
| Central Vac: | N |
| Laundry Level: | Syste |
| Ensuite Laundry: | F |
| Elevator Lift: | False |
| Sewers: | Sewer |
| Although the information displayed is believed to be accurate, no warranties or representations are made of any kind. |
| CENTURY 21 MILLER REAL ESTATE LTD. |
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| Book Showing | Email a Friend |
| Type: | Freehold - Detached |
| Area: | Halton |
| Municipality: | Oakville |
| Neighbourhood: | 1013 - OO Old Oakville |
| Style: | 2-Storey |
| Approximate Age: | 16-30 |
| Tax: | $46,602 |
| Beds: | 5 |
| Baths: | 8 |
| Fireplace: | Y |
| Pool: | Inground |