553763 Road 55 N/A

ActiveGrey Highlands · Grey Highlands91 days on marketMLS® X13098426

$1,899,900

$543 / sq ft

Bedrooms5

Bathrooms4

Interior3,500 sq ft

Lot Size2 sq ft

TypeSingle Family Home

ListingFor Sale

Days on Market91

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.

Features & finishes

View

Fireplace

Air Conditioning

Basement

Property details

MLS® Number	X13098426
Status	Active
Listing Type	For Sale
Property Type	Single Family Home
Interior Size	3,500 sq ft
Lot Size	2 sq ft
Beds / Baths	5 bed · 4 bath
Neighbourhood	Grey Highlands
City	Grey Highlands
Postal Code	N0C 1J0
Province	ON
Listed Date	May 7, 2026
Days on Market	91
Price per Sq Ft	$543
Brokerage	Chestnut Park Real Estate