553763 Road 55 Grey Highlands, Ontario N0C 1J0
$1,899,900
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. (id:40227)
Property Details
| MLS® Number | X13098426 |
| Property Type | Single Family |
| Community Name | Grey Highlands |
| AmenitiesNearBy | Golf Nearby, Ski Area |
| CommunityFeatures | School Bus |
| EquipmentType | Propane Tank |
| Features | Level Lot, Open Space, Flat Site, Sauna |
| ParkingSpaceTotal | 13 |
| RentalEquipmentType | Propane Tank |
| Structure | Deck, Porch |
Building
| BathroomTotal | 5 |
| BedroomsAboveGround | 5 |
| BedroomsTotal | 5 |
| Age | 100+ Years |
| Amenities | Fireplace(s), Separate Heating Controls |
| Appliances | Garage Door Opener Remote(s), Central Vacuum, Water Heater, Water Purifier, Water Softener, Water Treatment, Dishwasher, Dryer, Garage Door Opener, Microwave, Stove, Washer, Window Coverings, Wine Fridge, Refrigerator |
| BasementDevelopment | Finished |
| BasementType | N/a (finished) |
| ConstructionStyleAttachment | Detached |
| CoolingType | None |
| ExteriorFinish | Brick, Wood |
| FireProtection | Security System |
| FireplacePresent | Yes |
| FireplaceTotal | 2 |
| FlooringType | Hardwood |
| FoundationType | Poured Concrete, Stone |
| HalfBathTotal | 2 |
| HeatingFuel | Propane |
| HeatingType | Radiant Heat |
| StoriesTotal | 2 |
| SizeInterior | 3500 - 5000 Sqft |
| Type | House |
| UtilityPower | Generator |
| UtilityWater | Drilled Well |
Parking
| Detached Garage | |
| Garage |
Land
| AccessType | Public Road |
| Acreage | No |
| LandAmenities | Golf Nearby, Ski Area |
| LandscapeFeatures | Landscaped |
| Sewer | Septic System |
| SizeDepth | 229 Ft |
| SizeFrontage | 298 Ft |
| SizeIrregular | 298 X 229 Ft |
| SizeTotalText | 298 X 229 Ft|1/2 - 1.99 Acres |
| ZoningDescription | Rural |
Rooms
| Level | Type | Length | Width | Dimensions |
|---|---|---|---|---|
| Second Level | Primary Bedroom | 4.63 m | 3.99 m | 4.63 m x 3.99 m |
| Second Level | Bedroom | 3.18 m | 2.91 m | 3.18 m x 2.91 m |
| Second Level | Bedroom | 3.18 m | 2.96 m | 3.18 m x 2.96 m |
| Second Level | Bedroom | 7.31 m | 2.73 m | 7.31 m x 2.73 m |
| Second Level | Loft | 4.98 m | 2.82 m | 4.98 m x 2.82 m |
| Basement | Family Room | 8.66 m | 6.46 m | 8.66 m x 6.46 m |
| Main Level | Great Room | 13.1 m | 4.11 m | 13.1 m x 4.11 m |
| Main Level | Sunroom | 6.55 m | 3.32 m | 6.55 m x 3.32 m |
| Main Level | Kitchen | 8.86 m | 4.51 m | 8.86 m x 4.51 m |
| Main Level | Family Room | 4.11 m | 3.4 m | 4.11 m x 3.4 m |
| Main Level | Bedroom | 3.76 m | 3.4 m | 3.76 m x 3.4 m |
Utilities
| Cable | Installed |
| Electricity | Installed |
| Electricity Connected | Connected |
| Telephone | Nearby |
https://www.realtor.ca/real-estate/29718077/553763-road-55-grey-highlands-grey-highlands
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393 First Street, Suite 100
Collingwood, Ontario L9Y 1B3
393 First Street, Suite 100
Collingwood, Ontario L9Y 1B3
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May 08 2026 04:03:06
Muskoka Haliburton Orillia – The Lakelands Association of REALTORS®
Chestnut Park Real Estate