Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 1 of 50

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 2 of 50

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 3 of 50

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 4 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 5 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 6 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 7 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 8 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 9 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 10 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 11 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 12 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 13 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 14 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 15 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 16 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 17 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 18 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 19 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 20 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 21 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 22 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 23 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 24 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 25 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 26 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 27 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 28 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 29 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 30 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 31 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 32 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 33 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 34 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 35 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 36 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 37 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 38 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 39 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 40 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 41 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 42 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 43 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 44 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 45 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 46 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 47 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 48 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 49 of 50

Unlock All 50 Photos

Enter your email for instant access

Detached for sale at 55 Chisholm Street, Oakville - 4 bedroom, 4 bathroom - Photo 50 of 50

Unlock All 50 Photos

Enter your email for instant access

1 / 50• 47 locked

Active

MLS® W12708196

55 Chisholm St

Name: HouseIndex
Address: 100 King Street West, Toronto, ON, M5X 1A9, CA
Telephone: +1-647-849-9977
Price range: Free

Oakville, ON L6K 3H6

$4,120,000

Bedrooms

Bathrooms

Size

3000-3500 sqft

Type

2-Storey

Parking

3 spaces

Age

100+ yrs

Taxes (2025)

$17,811.05

Get Verified Property Details

Know the exact year built and above grade square footage — verified and sent to you within 2 hours.

Free service · No spam · Data verified by our team

Description

Set within Oakville's West Harbour, 55 Chisholm Street is defined by originality and intent. Located steps from Tannery Park and Lake Ontario, this home was conceived as a work of art for those who value architecture, sustainability, and livability in equal measure. Inside, innovation drives the home as much as artistry geothermal heating and cooling, energy-recovery ventilation, and rainwater harvesting provide modern sustainability without sacrificing comfort. Natural plaster walls, custom ironwork, and a sculptural three-dimensional stairwell create moments of discovery at every turn. A dramatic soapstone fireplace anchors the main level, where open living and dining spaces frame views of the landscaped grounds and flow around a Scavolini kitchen with Miele appliances. The second floor offers three bedrooms and two bathrooms, including a primary suite that opens to a private terrace overlooking the property. Above, a treetop lookout provides a quiet, elevated perspective above the neighbourhood canopy, marking an unexpected and compelling architectural moment. The lower level thoughtfully integrates the home's original stone foundation with contemporary function, housing a den, guest suite, full bath, gym, laundry, and a cedar-lined wine cellar. Outdoors, nine distinct gathering spaces await, designed for both relaxation and entertaining. A cedar sauna and outdoor shower invite quiet unwinding, while a fire pit and full outdoor kitchen create an effortless setting, surrounded by lush landscaping. With access to the lake, trails, and the shops and restaurants of Downtown Oakville 55 Chisholm Street offers a rare balance of privacy and connection. This is a home for those who value craftsmanship over convention, restraint over excess, and design that reveals itself slowly. Every material, surface, and hidden detail reflects a life lived with intention. Singular in vision and execution, it stands apart for the few who recognize extraordinary design when they see it.

Price & Status History

Price history is locked

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 Date1/19/2026

Days on Market82 days

PossessionFlexible

Virtual Tour

View Virtual Tour

Book a Private Showing with HouseIndex

Guided by Vick Yogeswaran • REALTOR®

RE/MAX Realtron Realty Inc., Brokerage

15+ years experience in GTA real estate

Private showings arranged quickly

Expert negotiation support

No pressure • 100% free consultation

Get Exclusive Property Insights

Access information not available to the public – no agent pressure, just the facts you need.

Listing Courtesy of:

Sotheby's International Realty Canada, Brokerage

This listing is provided through the TRREB MLS® System.

Same-day showings available across the GTA

MLS® #W12708196

MLS® Data Disclaimer: The listing data provided is courtesy of the Toronto Regional Real Estate Board (TRREB) and its members. The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate and may not be used for any commercial purpose or any other purpose. The information is deemed reliable but is not guaranteed accurate by TRREB. MLS® and the associated logos are trademarks of The Canadian Real Estate Association (CREA) and identify the quality of services provided by members of CREA. REALTOR® is a trademark of REALTOR® Canada Inc., a corporation owned by CREA and the National Association of REALTORS®.

Data Accuracy: While every effort has been made to ensure the accuracy of the information, HouseIndex.ca makes no warranties or representations as to the accuracy, completeness, or reliability of this data. All information should be independently verified. Last updated data may not reflect the most current MLS® listings.