553763 Road 55 N/A, Grey Highlands, ON N0C 1J0
Grey Highlands
Welcome to one of Grey County's most extraordinary properties - a masterfully restored 1884 red brick schoolhouse transformed into a remarkable country estate with over 5,000 sf of living space where history, architecture, and craftsmanship converge. Originally constructed as S.S. No. 3 Osprey Township, this iconic heritage building has been thoughtfully restored and seamlessly expanded, preserving its historic soul while introducing modern luxury and exceptional scale for contemporary living. Original details including the working school bell, chalkboard, soaring schoolhouse windows, and hand-etched brick remain beautifully intact, blending effortlessly with a dramatic contemporary addition completed in 2017. The original schoolhouse features an open-concept kitchen, dining, and living space beneath 17-foot cathedral ceilings, warmed by a wood stove and hydronic in-floor heating. The newer addition introduces a breathtaking great room with 22-foot ceilings and fireplace, sunroom, sauna, luxurious primary suite with exposed brick, additional guest bedrooms, and expansive lower-level recreation spaces. Offering 5 br and 5 ba, the home is equally suited for refined entertaining, multi-generational living, or peaceful country retreat. Complementing the residence is a custom timber-frame garage inspired by the original schoolhouse architecture. Built to residential standards, it features soaring 27-foot ceilings, heated floors, loft office/lounge space, full bathroom, car lift & premium C Tech Manufacturing cabinetry. Set on approximately 1.57 private acres with mature landscaping, security system, and Generac backup generator, the property is ideally positioned near Pretty River Valley Provincial Park, Kolapore Highlands trails, Devil's Glen, Creemore, & Collingwood, with access to exceptional hiking, cycling, skiing, artisan markets, and Michelin-recognized dining. A rare opportunity to own a beautifully restored historic property reimagined for modern country living.
Estimate only - excludes property tax, condo fees, utilities and home insurance. Rates vary by lender and term; based on semi-annual compounding.
Walkability, transit, and bike-friendliness for 553763 Road 55 N/A, Grey Highlands, ON N0C 1J0
Provided by Walk Score®. Walk Score, Transit Score, and Bike Score are trademarks of Walk Score.
MLS# X13098426
Listed by Chestnut Park Real Estate
On market since May 7, 2026
553763 Road 55 N/A, Grey Highlands, ON N0C 1J0 is listed for $1,899,900 CAD.
553763 Road 55 N/A, Grey Highlands, ON N0C 1J0 has 5 bedrooms and 4 bathrooms.
553763 Road 55 N/A, Grey Highlands, ON N0C 1J0 is a Detached.
553763 Road 55 N/A, Grey Highlands, ON N0C 1J0 is in Grey Highlands, Ontario.
553763 Road 55 N/A, Grey Highlands, ON N0C 1J0 is currently for sale.
Contact Michael Mezheritsky at +1 (416) 716-4439 to arrange a private showing of 553763 Road 55 N/A, Grey Highlands, ON N0C 1J0 (MLS# X13098426). You can also send a message through the contact form on this site.
