$10,750,000
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155 Gloucester Avenue, Oakville on L6J 3W3, Oakville, ON L6J 3W3

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5 Beds
8 Baths
7,355 Sq Ft

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 chefs 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 By: Brad Miller - Century 21 Miller Real Estate Ltd. cnitso Realty.com
  • MLS® 40833571
  • Date Listed05/26/2026
  • Days on Realty 12 Days
  • Bedrooms 5
  • Bathrooms 6 Full baths, 2 Half baths
  • Lot Size 0.64 acres (27,966 sq. ft)
  • County Halton
  • Year Built 2004
  • Square Feet 7,355 sq. ft
  • Price Per Sq. Ft $1461.59

Interior Features

  • Cooling Central Air
  • Heating Forced Air

Exterior / Lot Features

  • Exterior Built-in Barbecue, Landscape Lighting, Landscaped, Lawn Sprinkler System, Lighting, Privacy
  • Roof -
  • Lot Size Acres 0.64
  • Lot Size SQFT 27,965.52
  • Lot Features Urban, Rectangular, City Lot, Library, Major Highway, Park, Rec./ Community Centre, Schools

Directions

Lakeshore Rd E, North on Gloucester

Sales & Tax History

Source: Public Records

Local Neighborhood Highlights for L6J 3W3

Discover key demographics, population statistics, and environmental insights for the Oakville, ON area.

Walkability in ON / L6J 3W3

Source: Walk Score

77/100

Very Walkable

Walk Score ®

33/100

Some Transit

Transit Score ®

63/100

Bikable

Bike Score ®

Overview

Most errands can be accomplished on foot. A few nearby public transportation options. Some bike infrastructure.

Transit Summary

4 nearby routes: 4 bus, 0 rail, 0 other

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 40/100, Transit Score: 38/100, Bike Score: 49/100.

Points of Interest near 155 Gloucester Avenue, Oakville ON L6J 3W3, Oakville, ON L6J 3W3

Frequently Asked Questions for 155 Gloucester Avenue, Oakville ON L6J 3W3

Source: Realty.com

155 Gloucester Avenue, Oakville ON L6J 3W3, Oakville, ON L6J 3W3 in Oakville, ON L6J 3W3 is a single family residence listed at $10,750,000. Highlights include 5 bedrooms, 8 bathrooms, 7,355 sq. ft., built in 2004, 0.64 acre lot, $1,462 per sq. ft.. Realty.ca has 44 photos, sales history, school insights, and mortga...

Realty.com has 44 photos of 155 Gloucester Avenue, Oakville ON L6J 3W3.

Our records indicate that 155 Gloucester Avenue, Oakville ON L6J 3W3 was built in 2004.

The full address for this home is 155 Gloucester Avenue, Oakville ON L6J 3W3, Oakville, ON L6J 3W3.

155 Gloucester Avenue, Oakville ON L6J 3W3 has been listed on Realty.com since Tue May 26, 2026

Most errands can be accomplished on foot. A few nearby public transportation options. Some bike infrastructure.

The average walkability score in the surrounding area is Walk Score: 40/100, Transit Score: 38/100, Bike Score: 49/100.

Listing provided courtesy of: Century 21 Miller Real Estate Ltd. - itso (tel: 905-845-9180)
Listing agent: Brad Miller - UnknownState (tel: 905-338-2121)

This content last refreshed on 2026-06-07 04:10:30. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.