155 Gloucester Avenue

Set on one of the most coveted streets in Old Oakville, this extraordinary residence represents a rare offering of architectural significance, timeless design, and resort-inspired living on an irreplaceable 0.6-acre property. Originally designed by locally renowned architect Bill Hicks and masterfully built by Legend Homes, the residence underwent a comprehensive renovation in 2021 where no detail was overlooked and no room was left untouched, resulting in almost 12,000 square feet of exquisitely finished living space that seamlessly blends classic elegance with modern luxury.

 

Surrounded by mature trees and impeccable mature landscaping, the home commands a remarkable presence from the moment of arrival. A sweeping drive and triple car garage set the tone, while the striking façade, natural stone walkways and perfectly proportioned architecture create a sense of understated grandeur rarely found in today’s market. Inside, the residence unfolds through a series of beautifully scaled principal rooms, soaring ceilings, expansive windows, and refined finishes curated to the highest standard. Every element has been thoughtfully considered to create a home equally suited for large-scale entertaining and intimate family living.

 

At the heart of the home is a spectacular chef’s kitchen anchored by custom Downsview cabinetry, extensive stone surfaces, and professional-grade appliances, all designed with both beauty and functionality in mind. The kitchen flows seamlessly into the adjoining family and entertaining spaces, creating an inviting atmosphere filled with natural light and views of the private backyard retreat. Elegant formal living and dining rooms offer timeless entertaining spaces, while thoughtfully integrated informal areas provide warmth and comfort throughout the home.

 

An impressive extra-wide staircase serves as a stunning architectural focal point and leads to the second level, where each bedroom has been designed as a private suite complete with semi-vaulted ceilings and beautifully appointed ensuites. The primary retreat is exceptional in both scale and sophistication. In addition to the spacious sleeping quarters, the suite features a dedicated sitting room with private balcony, ideal for a quiet lounge or morning retreat. The oversized dressing room is finished with custom wall-to-wall cabinetry, extensive built-ins and display cabinetry, creating a boutique-inspired experience. The accompanying spa-inspired ensuite offers a serene atmosphere with luxurious finishes and exceptional attention to detail.

 

The lower level is expansive and thoughtfully planned, it features an oversized fitness studio, temperature-controlled wine cellar, sophisticated wet bar, and a sprawling recreation space. A walk-up to the backyard creates seamless indoor-outdoor connectivity, while two dedicated music rooms offer exceptional flexibility for musicians, creators or collectors seeking specialized spaces within the home.

 

Last but certainly not least is the extraordinary outdoor setting. Completely refreshed in 2025, the backyard has been transformed into a private resort-like oasis designed for year-round enjoyment. The gunite pool is complemented by two separate sets of pool equipment, allowing the hot tub to operate throughout the winter months for an unmatched four-season experience. Extensive natural stone patios and walkways surround the grounds, creating multiple areas for lounging, dining, and entertaining. A fully equipped outdoor kitchen elevates the space further, offering the ultimate setting for summer gatherings, elegant outdoor dinners and effortless entertaining beneath the mature tree canopy.

 

Situated on one of Old Oakville’s most prestigious streets, this residence offers an unparalleled lifestyle just moments from the lake, downtown Oakville, top-ranked schools, parks, and every amenity imaginable. Combining landmark architecture, extraordinary craftsmanship, resort-calibre amenities and an irreplaceable property, 155 Gloucester Avenue represents one of the finest luxury offerings to come to market in Old Oakville.

Set on one of the most coveted streets in Old Oakville, this extraordinary residence represents a rare offering of architectural significance, timeless design, and resort-inspired living on an irreplaceable 0.6-acre property. Originally designed by locally renowned architect Bill Hicks and masterfully built by Legend Homes, the residence underwent a comprehensive renovation in 2021 where no detail was overlooked and no room was left untouched, resulting in almost 12,000 square feet of exquisitely finished living space that seamlessly blends classic elegance with modern luxury.

 

Surrounded by mature trees and impeccable mature landscaping, the home commands a remarkable presence from the moment of arrival. A sweeping drive and triple car garage set the tone, while the striking façade, natural stone walkways and perfectly proportioned architecture create a sense of understated grandeur rarely found in today’s market. Inside, the residence unfolds through a series of beautifully scaled principal rooms, soaring ceilings, expansive windows, and refined finishes curated to the highest standard. Every element has been thoughtfully considered to create a home equally suited for large-scale entertaining and intimate family living.

 

At the heart of the home is a spectacular chef’s kitchen anchored by custom Downsview cabinetry, extensive stone surfaces, and professional-grade appliances, all designed with both beauty and functionality in mind. The kitchen flows seamlessly into the adjoining family and entertaining spaces, creating an inviting atmosphere filled with natural light and views of the private backyard retreat. Elegant formal living and dining rooms offer timeless entertaining spaces, while thoughtfully integrated informal areas provide warmth and comfort throughout the home.

 

An impressive extra-wide staircase serves as a stunning architectural focal point and leads to the second level, where each bedroom has been designed as a private suite complete with semi-vaulted ceilings and beautifully appointed ensuites. The primary retreat is exceptional in both scale and sophistication. In addition to the spacious sleeping quarters, the suite features a dedicated sitting room with private balcony, ideal for a quiet lounge or morning retreat. The oversized dressing room is finished with custom wall-to-wall cabinetry, extensive built-ins and display cabinetry, creating a boutique-inspired experience. The accompanying spa-inspired ensuite offers a serene atmosphere with luxurious finishes and exceptional attention to detail.

 

The lower level is expansive and thoughtfully planned, it features an oversized fitness studio, temperature-controlled wine cellar, sophisticated wet bar, and a sprawling recreation space. A walk-up to the backyard creates seamless indoor-outdoor connectivity, while two dedicated music rooms offer exceptional flexibility for musicians, creators or collectors seeking specialized spaces within the home.

 

Last but certainly not least is the extraordinary outdoor setting. Completely refreshed in 2025, the backyard has been transformed into a private resort-like oasis designed for year-round enjoyment. The gunite pool is complemented by two separate sets of pool equipment, allowing the hot tub to operate throughout the winter months for an unmatched four-season experience. Extensive natural stone patios and walkways surround the grounds, creating multiple areas for lounging, dining, and entertaining. A fully equipped outdoor kitchen elevates the space further, offering the ultimate setting for summer gatherings, elegant outdoor dinners and effortless entertaining beneath the mature tree canopy.

 

Situated on one of Old Oakville’s most prestigious streets, this residence offers an unparalleled lifestyle just moments from the lake, downtown Oakville, top-ranked schools, parks, and every amenity imaginable. Combining landmark architecture, extraordinary craftsmanship, resort-calibre amenities and an irreplaceable property, 155 Gloucester Avenue represents one of the finest luxury offerings to come to market in Old Oakville.