For Sale - 155 Gloucester Avenue, Oakville, Ontario

Est payment $51,620/mo
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Time on Jump  1 days
  • Rare landmark architecture on a coveted street in Old Oakville.
  • Extensive renovation in 2021 yields nearly 12,000 square feet of luxury.
  • Designer chef's kitchen with custom cabinetry and professional-grade appliances.
  • Resort-like outdoor space with gunite pool and fully equipped kitchen.
  • Close to the lake, downtown, schools, and parks for convenient living.



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.
Listing IDW13176888
Address155 Gloucester Avenue
CityOakville, Ontario
Price$10,750,000
Bed / Bath5 / 8 Full
Style2-Storey, Detached
ConstructionStone, Wood
Land Size0.642
TypeResidential
StatusFor Sale
Subtype DetachedIndoor Features Auto Garage Door Remote, Built-In Oven, Separate Heating ControlsOutdoor Features Built-In-BBQ, Hot Tub, Landscape Lighting, Landscaped, Lawn Sprinkler System, Lighting, Patio, PrivacyAmenities Lake/Pond, Library, Marina, Park, Rec./Commun.Centre, SchoolOwnership FreeholdViews Trees/WoodsBasement Full, Walk-Up, FinishedFoundation Poured ConcreteHeating / Cooling Forced AirHeating Fuel GasSewer Sewer
Parking 9.00
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Listing Agency:  CENTURY 21 MILLER REAL ESTATE LTD.

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155 Gloucester Avenue
Oakville , Ontario
5 8 $10,750,000
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