155 Gloucester Avenue, Oakville, ON

Oakville, 1013 - OO Old Oakville Hood
Lakeshore Road E/Gloucester Ave
5 Br | 8 Bath | 5000 + Sqft
$10,750,000 For Sale

Property Overview

  • Detached — 2-Storey
  • SqFt: | 5000 + Sqft
  • Lot Size: 149.89 x 187.50 Feet
  • Age: 16-30 Years
  • Basement: Full, Walk-Up, Finished
  • Exterior: Stone, Wood
  • Taxes: 46,602 / 2026
  • Zoning: n/a
  • MLS #: W13176888
  • Sewer: Sewer
  • Heat Source: Gas , Forced Air

Property Description

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.

Property Details

  • For: For Sale
  • Type: Detached
  • Style: 2-Storey
  • Lot: 149.89 x 187.50 Feet
  • Region: Halton
  • Hood: 1013 - OO Old Oakville
  • Zoning: n/a
  • Lot Irreg: 149.89' x 187.50' x 151.06' x 186.61'
  • Fronting On: East

Building Details

  • Age: 16-30 Years
  • Exterior: Stone, Wood
  • Heat: Gas , Forced Air
  • A/C: Central Air
  • Interior Features: Auto Garage Door Remote, Built-In Oven, Separate Heating Controls
  • Pool: Inground, Salt
  • Sewer: Sewer
  • Garage: Attached
  • Total Parking: 9.00
  • Driveway: Private Triple

Property Interior

  • Sqft: 5000 + Sqft
  • Bed: 5
  • Bath: 8
  • Kitchen: 1
  • Family Room: No
  • Basement: Full, Walk-Up, Finished
Rooms Details

Foyer

Main Level

4.57 x 3.07

Kitchen

Main Level

7.24 x 5.97

Breakfast

Main Level

3.66 x 3.66

Living Room

Main Level

5.84 x 4.55

Dining Room

Main Level

5.44 x 4.57

Family Room

Main Level

7.9 x 6.3

Den

Main Level

4.57 x 4.55

Office

Main Level

4.06 x 3.73

Primary Bedroom

Second Level

5.56 x 5.38

Sitting

Second Level

4.57 x 4.55

Bedroom 2

Second Level

5.44 x 4.57

Bedroom 3

Second Level

5.16 x 4.55

Bedroom 4

Second Level

3.96 x 3.66

Bedroom 5

Second Level

4.09 x 3.61

Recreation

Basement Level

8.25 x 7.67

Game Room

Basement Level

6.55 x 5.82

Exercise Room

Basement Level

16.46 x 3.12

Other

Basement Level

3.43 x 3.35

Other

Basement Level

4.55 x 4.42

Utility Room

Basement Level

9.19 x 5.03

Other

Basement Level

3.02 x 2.13

Cold Room/Cantina

Basement Level

2.97 x 2.77

Property Listed by: CENTURY 21 MILLER REAL ESTATE LTD.
Virtual Tour: n/a

Home Valuation Estimate

What is 155 Gloucester Avenue, Oakville, ON worth in today’s 1013 - OO Old Oakville, Oakville market?

This HomeZira valuation preview helps buyers and sellers think through the asking price for this 5-bedroom Detached with 5000 + sq. ft. in 1013 - OO Old Oakville, Oakville. The full estimate reviews the property’s location, home type, bedroom count, size range, age, and nearby comparable market activity after sign-in.

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Location

  • Address: 155 Gloucester Avenue
  • Neighborhood: 1013 - OO Old Oakville
  • Zip/Postal Code: L6J 3W3
  • Nearby Amenities: Lake/Pond, Library, Marina, Park, Rec./Commun.Centre, School
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About 155 Gloucester Avenue, Oakville, ON L6J 3W3, Oakville

Located at 155 Gloucester Avenue, Oakville, ON in Oakville (1013 - OO Old Oakville neighbourhood), near Lakeshore Road E/Gloucester Ave. This freehold home offers Detached, ["2-Storey"], 5 bedrooms, 8 bathrooms and 5000 + sq.ft. (approx.) in a layout suited to everyday family living. Basement: Full, Walk-Up, Finished • 9 parking spots • Garage: Attached • Heating: Gas Forced Air • Cooling: Central Air. Property taxes are approximately $46,602 for 2026. 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, expans.

FAQs for 155 Gloucester Avenue, Oakville, ON , 1013 - OO Old Oakville , Oakville

What are the listing details for 155 Gloucester Avenue, Oakville, ON?
155 Gloucester Avenue, Oakville, ON is a Detached for sale in Oakville, in the 1013 - OO Old Oakville neighbourhood, Halton. The current list price is $10,750,000. MLS number: W13176888.
How many bedrooms and bathrooms does this home have?
155 Gloucester Avenue, Oakville, ON is listed as a Detached with a ["2-Storey"] style, featuring 5 bedroom(s) and 8 bathroom(s). The listed interior size range is 5000 + sq. ft..
What lot, basement, garage, or parking details are listed?
The lot size is listed as approximately 149.89 x 187.50 Feet. The basement is listed as: Full, Walk-Up, Finished. Garage type: Attached. Total parking: 9 space(s).
What heating, cooling, and exterior details are shown?
Heating is listed as: Gas, Forced Air. Cooling is listed as: Central Air. Exterior/construction materials are listed as: Stone, Wood .
Where is this property located?
155 Gloucester Avenue, Oakville, ON is located in the 1013 - OO Old Oakville neighbourhood of Oakville. The listed cross street is Lakeshore Road E/Gloucester Ave.
What information is available on this public listing page?
The public listing page shows current active listing information, property photos, room details when available, map location, listed price, property features, and contact options. Annual taxes are listed as $46,602 / 2026. Valuation tools and similar sold-property previews are available after sign-in where applicable, without displaying sold data in this public FAQ.

FAQ content is based on current active listing fields shown on this page. Sold prices, sold comparables, and VOW-only details are not included in this public FAQ.