This property was sold on January 31, 2026. This listing is for reference purposes only. to view the sold price.
Welcome to this remarkable 2-Storey detached located in the coveted neighborhood of Grey Highlands. Expertly crafted featuring premium brick construction, this residence presents an exceptional opportunity offered at $585,000 to acquire a beautiful home in a highly sought-after setting. Designed for both comfortable daily living and elegant entertaining, the layout maximizes natural light, functional flow, and lifestyle utility.
Built in 1875, this home is filled with the timeless charm of its historic roots. Step inside and you're welcomed by an inviting foyer that hints at the character waiting within. To your right, the sunlit dining room feels instantly comforting-ideal for family meals or hosting friends. Original hardwood floors, soaring ceilings, and detailed moldings carry the warmth of the past into every room. The spacious living room is full of potential, whether you're curling up with a book or entertaining a crowd. Built-in bookshelves create a cozy nook for reading or showcasing cherished keepsakes. The kitchen blends old-world charm with modern convenience, offering space for casual dining around an eat-in table, and a traditional woodstove that brings rustic comfort and winter warmth. This updated kitchen is a dream for anyone who loves to cook. A four-piece bath and laundry on the main level add everyday ease. Just off the kitchen, a flexible room-once an office-could become a sun-drenched studio, den, or quiet retreat, thanks to its south-facing windows and views of the backyard. Step outside to a peaceful patio overlooking a lovingly maintained garden with flowering trees, perennials, and your own veggie patch. The charm continues upstairs with a second full bath, and four large bedrooms. The property also includes 27 Main St E., a separate detached building with its own entrance. Formerly a doctor's office, bakery, and bookkeeping service, it's ideal for a home-based business, in-law suite, or income-generating rental. Perfectly located just steps from Markdale's main intersection, you're within walking distance to the new hospital, school, and all downtown conveniences.
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This detached home located at 27-29 MAIN Street, Grey Highlands is currently for sale and has been available on SousaSells for 274 days. This property is listed at $585,000 with an estimated mortgage of $1,947* per month. It has 4 beds, 2 bathrooms, and is 2000-2500 square feet. 27-29 MAIN Street, Grey Highlands is in the Grey Highlands neighborhood.
* Estimated mortgage assumes a 30% down payment, 4.00% interest rate, and 30-year amortization.Hospital, School, Rec./Commun.Centre, Fenced Yard, Library, Park
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No historical data available for this property.
This could be the first listing for this address.
Data-driven valuation for 27-29 MAIN Street E, Grey Highlands, ON N0C 1H0
Based on 0 recent similar sales in the pocket.
Properties in this area are selling at a steady pace.
Calculate your monthly payment, minimum downpayment, and land transfer taxes for this home in Grey Highlands.
About Purchasing a Home in Grey Highlands, ON
For a property listed at $585,000 in Grey Highlands, the legal minimum down payment is $33,500 under current Canadian banking regulations. This calculation applies a 5% requirement on the first $500,000, 10% on the next $499,999, and a flat 20% on any amount exceeding $1,000,000.
Additionally, buyers in Ontario must budget for the Provincial Land Transfer Tax, which is estimated at $8,175 for this transaction. As this listing is in Grey Highlands (outside the City of Toronto), no additional municipal land transfer tax is levied, resulting in total estimated land transfer taxes of $8,175.
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Disclaimer: AI Insights are generated by an automated system and should be used for informational purposes only. While we strive for accuracy using current market data and deep-learning models, these assessments do not constitute professional real estate, legal, or financial advice. All property values, predictions, and scores are estimates. We strongly recommend verifying all property details and conducting independent due diligence with a licensed professional before making any purchase decisions.