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5 Beds
4 Baths

C$1,749,900

553763 Road 55, Grey Highlands ON, N0C 1J0

Property typeResidential

Overview

Active

New

Listed May 7, 2026

Updated 4 weeks ago

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.

Additional information

MLS® ID
X13098426

Interior Features

Bedrooms
5
Bathrooms
4
Fireplace
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
1.58 Acres

Other Property Details

Taxes
$7,812
Tax Frequency
Annually
Garage
Yes
View
Yes
55+/Senior Community
No

 

Courtesy of Listed by , Chestnut Park Real Estate,

Based on information from the Toronto Regional Real Estate Board. The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate and may not be used for any commercial purpose or any other purpose. Information is deemed reliable but is not guaranteed accurate.

©2026 Toronto Real Estate Board. All rights reserved. 

Data last updated 2:29 AM UTC, 9/10/2026

 

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