553763 Road 55

About this home

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.

Details

Type

Detached

Style

2-Storey

Age

100+ years

Size

3500-5000 sq ft

Lot

298 × 229 ft

Basement

Finished

Garage

Detached

Kitchens

1

Property tax

$7,812 (2025)

Neighbourhood

Grey Highlands

Municipality

Grey Highlands

Price per sq ft

~$412 (28% below detached houses in Grey Highlands, $576)

Interior

Bedrooms

5 above ground

Bathrooms

1 × 4-piece (main), 1 × 3-piece (main), 1 × 5-piece (second), 1 × 2-piece (second)

Rooms

10 above ground + 1 below

Family room or den

Yes

Fireplace

Propane, Wood

Features

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

Heating, cooling and services

Heating

Radiant, Propane

Water and sewer

Septic

Building and exterior

Style

2-Storey

Exterior

Brick, Wood

Roof

Metal

Foundation

Poured Concrete, Stone

Age

100+

Faces

East

Outdoor

Deck, Landscaped, Porch, Year Round Living

Parking

Garage spaces

3

Total parking

13

Driveway and parking

Private

Lot

Size

298 × 229 ft (rectangular)

Acreage

.50-1.99

More

Possession

ASAP

Nearby

Golf, Level, School Bus Route, Skiing

Cross street

4th Concession B

Rooms