Aldo Udovicic, BrokerRe/Max Crossroads Realty Inc., Brokerage533 Danforth Rd, Scarborough(416) 438-2536getaldonow@gmail.com
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Listings553763 Road 55 N/A

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

$1,899,900

activeNEW
MLS® #X13098426Single Family HomeGrey Highlands
5Beds
4Baths
3,500Sq Ft
2Lot Sq Ft
553763 Road 55 N/A, Grey Highlands, ON N0C 1J0 - Photo 1
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About This Property

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.

Property Details

Property Type

Single Family Home

Status

Active

MLS® Number

X13098426

Bedrooms

5

Bathrooms

4

Interior Sq Ft

3,500

Lot Size

2 sqft

Neighbourhood

Grey Highlands

Listed

May 8, 2026

Features & Amenities

View
Fireplace
Air Conditioning
Basement
0

Listing Information

MLS®# X13098426
Chestnut Park Real Estate
Listed May 8, 2026

$1,899,900

Single Family Home · For Sale

5

Beds

4

Baths

3,500

Sq Ft

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Re/Max Crossroads Realty Inc., Brokerage — 533 Danforth Rd, Scarborough ON M1K 1C9