| 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. |
| Price | $1,899,900 |
| Taxes: | $7812.00 |
| Assessment Year: | 2026 |
| Occupancy: | Owner |
| Address: | 553763 Road 55 N/A , Grey Highlands, N0C 1J0, Grey County |
| Acreage: | .50-1.99 |
| Directions/Cross Streets: | 4th Concession B |
| Rooms: | 10 |
| Rooms +: | 1 |
| Bedrooms: | 5 |
| Bedrooms +: | 0 |
| Family Room: | T |
| Basement: | Finished |
| Level/Floor | Room | Length(ft) | Width(ft) | Descriptions | |
| Room 1 | Main | Great Roo | 42.97 | 13.48 | Gas Fireplace, Cathedral Ceiling(s) |
| Room 2 | Main | Sunroom | 21.48 | 10.89 | |
| Room 3 | Main | Kitchen | 29.06 | 14.79 | Combined w/Dining, Hardwood Floor, Cathedral Ceiling(s) |
| Room 4 | Main | Family Ro | 13.48 | 11.15 | Hardwood Floor, Cathedral Ceiling(s) |
| Room 5 | Main | Bedroom | 12.33 | 11.15 | |
| Room 6 | Second | Primary B | 15.19 | 13.09 | 5 Pc Ensuite, Hardwood Floor |
| Room 7 | Second | Bedroom | 10.43 | 9.54 | Hardwood Floor |
| Room 8 | Second | Bedroom | 10.43 | 9.71 | Hardwood Floor |
| Room 9 | Second | Bedroom | 23.98 | 8.95 | |
| Room 10 | Second | Loft | 16.33 | 9.25 | |
| Room 11 | Basement | Family Ro | 28.4 | 21.19 |
| Washroom Type | No. of Pieces | Level |
| Washroom Type 1 | 4 | Main |
| Washroom Type 2 | 3 | Main |
| Washroom Type 3 | 5 | Second |
| Washroom Type 4 | 2 | Second |
| Washroom Type 5 | 2 | Ground |
| Total Area: | 0.00 |
| Approximatly Age: | 100+ |
| Property Type: | Detached |
| Style: | 2-Storey |
| Exterior: | Brick, Wood |
| Garage Type: | Detached |
| (Parking/)Drive: | Private |
| Drive Parking Spaces: | 10 |
| Park #1 | |
| Parking Type: | Private |
| Park #2 | |
| Parking Type: | Private |
| Pool: | None |
| Approximatly Age: | 100+ |
| Approximatly Square Footage: | 3500-5000 |
| Property Features: | Golf, Level |
| CAC Included: | N |
| Water Included: | N |
| Cabel TV Included: | N |
| Common Elements Included: | N |
| Heat Included: | N |
| Parking Included: | N |
| Condo Tax Included: | N |
| Building Insurance Included: | N |
| Fireplace/Stove: | Y |
| Heat Type: | Radiant |
| Central Air Conditioning: | None |
| Central Vac: | Y |
| Laundry Level: | Syste |
| Ensuite Laundry: | F |
| Elevator Lift: | False |
| Sewers: | Septic |
| Water: | Drilled W |
| Water Supply Types: | Drilled Well |
| Utilities-Cable: | Y |
| Utilities-Hydro: | Y |
| Although the information displayed is believed to be accurate, no warranties or representations are made of any kind. |
| Chestnut Park Real Estate |
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| Book Showing | Email a Friend |
| Type: | Freehold - Detached |
| Area: | Grey County |
| Municipality: | Grey Highlands |
| Neighbourhood: | Grey Highlands |
| Style: | 2-Storey |
| Lot Size: | x 229.00(Feet) |
| Approximate Age: | 100+ |
| Tax: | $7,812 |
| Maintenance Fee: | $0 |
| Beds: | 5 |
| Baths: | 5 |
| Garage: | 0 |
| Fireplace: | Y |
| Air Conditioning: | |
| Pool: | None |