Central · L6K 3H6
$3,850,000
$1,283 / sq ft4 months on market
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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.
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What this home costs beyond the asking price, and how that price compares to what else is on the market.
This home is priced in line with comparable listings — about 69% of comparable detached listings in Central are asking less.
Based on 16 comparable active detached listings in Central. These are asking prices, not sale prices.
Estimate only. Excludes CMHC insurance premiums, which apply below 20% down, and does not constitute a mortgage approval or an offer of credit.
Payable on closing, on top of the purchase price.
An estimate on the asking price of $3,850,000. Rates current as of September 2026; confirm the final figure with your real estate lawyer.
Listing courtesy of Sotheby's International Realty Canada, Brokerage. Listing data is provided in part by the Toronto Regional Real Estate Board (TRREB) and is deemed reliable but is not guaranteed accurate. Information is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties. Data is updated every 15 minutes.
Listing courtesy of CENTURY 21 MILLER REAL ESTATE LTD.
$3,998,900
Central
Listing courtesy of Royal LePage Real Estate Services Ltd., Brokerage
$4,390,000
Central
Listing courtesy of RE/MAX Aboutowne Realty Corp., Brokerage
$3,199,900
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Listing courtesy of Re/Max Alliance Realty
$3,980,000
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Listing courtesy of RIGHT AT HOME REALTY