Proudly Canadian
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 1 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 2 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 3 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 4 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 5 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 6 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 7 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 8 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 9 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 10 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 11 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 12 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 13 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 14 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 15 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 16 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 17 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 18 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 19 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 20 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 21 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 22 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 23 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 24 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 25 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 26 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 27 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 28 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 29 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 30 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 31 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 32 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 33 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 34 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 35 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 36 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 37 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 38 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 39 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 40 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 41 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 42 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 43 of 44
Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 44 of 44
1 / 4441 locked
View on map
Active

$3,850,000

55 Chisholm St

Oakville, ON L6K 3H6

55 Chisholm St, OakvilleListed at $3,850,000. 4 bedroom, 4 bathroom 2-Storey Detached. MLS® W13018186.

Possession · seller's timeline

Flexible

4Beds
4Baths
3000-3500sqft
Detached
2-Storey
3Parking
$17,811.05Taxes/yr · 2025

What's this home worth?

Get a free estimate for 55 Chisholm St

Description

It is rare to find a home that respects its history while boldly defining its future. Set within Oakville's prestigious West Harbour neighbourhood, 55 Chisholm Street is a study in modern heritage, where a century-old stone foundation anchors a home defined by thoughtful design and sustainable innovation. Superior craftsmanship and comfortable, functional spaces create a residence that is both considered and effortlessly livable. Every detail reflects a singular vision. The architecture bridges past and present with quiet confidence, pairing natural plaster walls and custom ironwork with a sculptural three-dimensional stairwell and a professional Valcucine kitchen outfitted with integrated Miele appliances. A striking soapstone fireplace grounds the main living area, while open-concept spaces extend toward landscaped gardens, creating a seamless connection between indoors and out. Its intelligence is expressed through restraint. Geothermal heating, energy-recovery ventilation, and rainwater harvesting are fully integrated, supporting a high level of performance without compromising design integrity. Upstairs, three well-appointed bedrooms and two bathrooms offer calm and privacy. The primary suite opens to a private terrace, while a treetop lookout captures elevated views across the neighbourhood canopy. The lower level includes a modern gym, cedar-lined wine cellar, and guest suite. Outside, the grounds continue the experience with a cedar sauna, outdoor shower, fire pit, and full outdoor kitchen. Steps from the lake and Downtown Oakville, this is a legacy property reimagined for the next century, offering a rare balance of architectural integrity, modern performance, and quiet, enduring livability.

Property Details

Property TypeDetached
Style2-Storey
Community1002 - CO Central
Approximate Age100+
Rooms11
Kitchens1
Washrooms4
Square Feet3000-3500 sqft
Lot Dimensions89.5 × 80 ft
Fronting OnEast
Dir/Cross StLakeshore Rd W / Chisholm St
ViewGarden
Garage TypeDetached
Garage Parking Spaces1
DrivePrivate Double
Parking Drive Spaces2
Total Parking Spaces3
ExteriorStucco (Plaster), Wood
RoofMetal
FoundationPoured Concrete, Stone
BasementFull, Finished
Fireplace FeaturesFreestanding, Wood
Heating TypeRadiant
Heating SourceGround Source
A/COther
SewersSewer
Taxes (2025)$17,811.05
HSTIncluded In
SecurityAlarm System, Security System, Smoke Detector
Other StructuresSauna
UFFINo
Listed Date4/20/2026
Days on Market153 days
PossessionFlexible

Virtual Tour

Powered by YouTube

Same-day showings available
5.0Rated 5 stars on Google ReviewsWhatsApp Us About This Listing

Property Insights

Home Value
Estimate

Listing Courtesy of: Sotheby's International Realty Canada, Brokerage

MLS® #W13018186

TRREBMLS®

The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing data is deemed reliable but is not guaranteed accurate by TRREB. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.

© 2026 Toronto Regional Real Estate Board. All rights reserved.

Thinking about living in Oakville?

Explore the neighbourhood guide for Oakville — market trends, popular areas, buyer tips, and more.

HouseIndex Take: 55 Chisholm Street

This detached (2-Storey) is located in the 1002 - CO Central neighbourhood of Oakville.

The home offers 4+1 bedrooms, 4 bathrooms.

Features include a full, finished basement, 3 parking spaces including a 1-car garage, a fireplace.

Additional details: lot dimensions of 89.5 × 80 feet.

Listed at $3,850,000 CAD with annual property taxes of $17,811.05 (2025). This listing has been on the market for 52 days.

About Oakville Real Estate

This Detached is located in the 1002 - CO Central community in Oakville. Oakville is an affluent lakefront town in Halton Region known for heritage estates in Old Oakville, a thriving downtown core along Lakeshore Road, and excellent schools. The QEW provides quick access to Toronto and Hamilton, while the Oakville GO station offers 30-minute service to Union. It consistently ranks among Canada's best places to live. Detached homes in Oakville are in high demand among families seeking space, privacy, and long-term equity growth.

Lakefront trails & Bronte HarbourTop-ranked Halton District School Board30-minute GO Train to Union StationBoutique shops along Lakeshore Road
~35 min commute to downtown TorontoWalkability: Walkable downtown — suburban outer areas
View full Oakville neighbourhood guide →