155 Gloucester Avenue, Oakville ON

About 155 Gloucester Avenue

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. (id:56071). Get more information on 155 Gloucester Avenue

Property Features

Appliances:  Wet Bar
Features:  Wet bar, Paved driveway, Automatic Garage Door Opener
Landscape:  Lawn sprinkler
Rental Equipment:  
Fireplace Total:  3
Fireplace:   Other - See remarks
Pool Type:  Inground pool
Directions:  Lakeshore Rd E, North on Gloucester
Zoning Description:  RL1-0
Interior Size:  11719 sqft
Community Features:  Community Centre
Access:  Highway Nearby
Lot:  0.642 ac|1/2 - 1.99 acres 0.642
Exterior Finish:  Stone, Wood
Water:  Municipal water, Municipal sewage system
Heating / Cooling:   / Central air conditioning
Age:  2004
Foundation: Poured Concrete
Construction:  Wood frame
Constructed Date:  2004
Basement:  Full (Finished) Finished

Rooms & Sizes

3pc Bathroom Second level Measurements not available	Bedroom Second level 13 5 x 11 10	3pc Bathroom Second level Measurements not available
Bedroom Second level 13 0 x 12 0	3pc Bathroom Second level Measurements not available	Bedroom Second level 16 11 x 14 11
3pc Bathroom Second level Measurements not available	Bedroom Second level 17 10 x 15 0	Sitting room Second level 15 0 x 14 11
Full bathroom Second level Measurements not available	Primary Bedroom Second level 18 3 x 17 8	Cold room Basement 9 9 x 9 1
Wine Cellar Basement 9 11 x 7 0	Utility room Basement 17 7 x 6 9	Utility room Basement 30 2 x 16 6
Other Basement 14 11 x 14 6	Other Basement 11 3 x 11 0	3pc Bathroom Basement Measurements not available
Gym Basement 54 0 x 10 3	Other Basement 14 0 x 8 1