55 Chisholm Street, Oakville, ON
Central, Oakville · MLS® W13018186
About this home
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.
Key facts
- Property type
- Detached, 2-Storey
- MLS®
- W13018186
- Bedrooms
- 4 (3 + 1)
- Bathrooms
- 4 (1 half)
- Size
- 3000-3500
- Lot
- 89.5 × 80 ft
- Cross streets
- Lakeshore Rd W / Chisholm St
- Parking
- 1 garage · 3 parking (detached)
- Driveway
- Private Double
- Basement
- Full, Finished
- Heating
- Radiant
- A/C
- Other
- Exterior
- Stucco (Plaster), Wood
- Foundation
- Poured Concrete, Stone
- Roof
- Metal
- Sewer
- Sewer
- Property tax
- $17,811 / 2025
- Days on market
- 88
- Listing brokerage
- Sotheby's International Realty Canada, Brokerage
Rooms
Listed at $3,850,000, this home is about 33% above what comparable homes suggest. The number above is my independent estimate of value, not the asking price.
There were not many closely comparable homes right in Central, so I widened the search to the surrounding area.
Based on 7 similar homes nearby, adjusted for size, beds, and baths.Median of 7 comparable active listings, adjusted for size, beds, and baths. The city (MPAC) assessment points to about $4.11M, higher than the comparables and worth a second look.
How I got there
Here is the exact math behind the estimate. I start from the closest comparable listing and adjust for the real differences (size, beds, baths) to land on a like-for-like value for this home.
- Closest comparable, listed at $3.50M
- Bedrooms −$30K
- Bathrooms −$15K
- Adjusts to $3.45M
That comparable adjusts to $3.45M; the $2.90M estimate above is the median of all 7 comparables, which is steadier than any single home.This uses comparable active listings, not sold prices. Lot, condition, and finishes are my in-person call, and I can run a full CMA with recent solds.
On location, this is a very walkable address with everyday errands close by. Rebecca St. + Chisholm St. is about a 4-minute walk away. Walkable, transit-friendly spots tend to hold value and widen your resale pool.
Total price vs nearby homes. Fair value about $2.90M, median of 7 comparables.
What the listing highlightsThese are claims from the listing. The only way to know for sure is to see it in person, and I am happy to book you a private showing.
- Upscale kitchen: a genuine value driver, verify the appliances, stone, and finishes in person.
- Premium lot / gardens: lot size and privacy hold value and cannot be changed, verify frontage, depth, and any easements.
- Open-concept layout: modern, sought-after flow.
- Value driver
- Lifestyle
The closest active listings by size, beds, and price, so you can see what this home is up against.
The 5 closest of 7 active listings nearby.
See all comparable homesThis home lists 11% above the area average of $1,072/sqft.
83 days longer than the Oakville average (5 days).
View comparable listingsPrice per square foot vs the area average.
Neighbourhood & location
Central, Oakville, ON
Enter a workplace or destination and we’ll show the door-to-door time by car, transit and bike.
Getting around
Very WalkableA walkability read built from the amenities around this home: how close the nearest transit stop is, and how many grocery, dining, park, and pharmacy destinations fall within a 15-minute walk. It is a guide, not a guarantee. Places data from Google.
Most daily errands can be done on foot.
🚉 Nearest transit: Rebecca St. + Chisholm St., about 346 m away
Within a 15-minute (1.5 km) walk.
How asking prices compare in the closest areas to this home. Longer bars mean a pricier market.
Typical asking price of active listings of the same type, per area (outliers removed). Oakville.
Get the full neighbourhood report (schools, parks, transit & safety) →
Affordability & Mortgage
Income needed assumes a ~32% GDS ratio; weekly is mortgage principal & interest only. Price ÷ income is the home price over the income needed. Fixed reference assumptions so listings compare on equal footing, not a lending decision.
Calculate and customize your mortgage and other expenses
Adjust the down payment, rate, and amortization, and add property tax, condo fees, and heating to see your true monthly cost.
Your numbers
Homes over $1.5M can't be insured, so 20% down or more is required.
Conventional (20%+ down). Best insured 5-year fixed 3.99% via Ratehub.ca (as of July 17, 2026); conventional rates run a little higher.
Mortgage amount $3,080,000 · 4.14% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $16,436
- Property tax
- $1,484
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $17,920
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $82,725
- Estimated closing costs
- $82,725
Plus your down payment of $770,000. Legal fees, title insurance, and adjustments are extra and vary by deal.
Mortgage stress test
Lenders qualify you at the greater of your rate plus 2% or 5.25%. You do not pay this rate. It just shows you could still handle payments if rates rose, so aim to stay comfortable at this higher number.
Over the full 25 years
At the end of your 5-year term
- Total paid over the term
- $986,161
- Principal paid down
- $392,239
- Interest paid
- $593,923
- Balance remaining
- $2,687,761
Talk to Team Asgarian about your options
Rates and programs change often. We will connect you with a trusted mortgage professional and build a plan that fits your budget and goals.
Estimates only, not a mortgage quote or pre-approval. Figures use Canadian semi-annual compounding, current minimum down-payment rules, CMHC premium tiers, and Ontario (plus Toronto, when selected) land transfer tax. Actual rates, taxes, insurance, and closing costs vary by lender and property. Confirm every number with your mortgage professional.
Investor snapshot
Thinking of this home as an investment? We will pull real comparable rents and run the full numbers with you.
Talk about the numbersEstimates only. Rent is modelled on above-grade size and local norms, so a finished basement or second suite (a separate entrance often means one) can push real rent well above this. Taxes, fees, and vacancy vary by property, and cap rate is before financing. A starting point, not a final number, let us run the real ones with you.
Helpful resources
All information deemed reliable but not guaranteed. For personal, non-commercial use only. Listing courtesy of Sotheby's International Realty Canada, Brokerage. MLS®/PropTx.