$1,899,900
FOR SALE

Detached 2-Storey

Bedrooms: 5Bathrooms: 4Lot: 298 x 229 ft
2025 Taxes: $7,812

553763 Road 55 N/A
Grey Highlands, ON N0C 1J0 | Grey County

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.
Extras
Auto Garage Door Remote, Bar Fridge, Central Vacuum, Generator - Partial, Propane Tank, Sauna, Separate Heating Controls, Water Heater Owned, Water Purifier, Water Softener, Water Treatment
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Listed By Chestnut Park Real Estate
Data Provided By Toronto Regional Real Estate Board
MLS® Listing Number X13098426
Last Updated May 17, 2026
Property Summary
Property Type Detached

More like this:
PIN 372610123
Legal Description PT LT 21 CON 4 OSPREY AS IN R45340; GREY HIGHLANDS
Possession Date ASAP
Taxes (2025) $7,812
Directions/Cross Streets 4th Concession B
Neighbourhood Grey Highlands
Area Grey County
Price History

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Detailed Information
Fronting On East
Special Designations Unknown
Included Cable TV
Bedrooms 5
Bathrooms 4
Lot 298 x 229 ft
Exterior Brick
Air Conditioning None
Family Room Y
Fireplace/Stove Y
Basement Finished
Garage Type Detached
Garage/Park Spaces Y
Parking Spaces 10
Heat Source Propane
Heat Type Radiant
Sewers Septic
Water Drilled Well

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