Price ChangeFor Sale

553763 Road 55
Grey Highlands, Grey County, ON, N0C 1J0

Detached
TRREB
MLS® Number: X13098426

Chestnut Park Real Estate

Listing brokerage
Estimated Value
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$1,749,900List Price
5Bedrooms
4Bathrooms
3Garages
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Listing History

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Current valuation for 553763 Road 55, Grey Highlands, ON N0C 1J0. Listed for $1,749,900 on 2026-10-19

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Description

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

GolfLevelSchool Bus RouteSkiing

Amenities

No amenities available

Summary

Tax:$7,812 / 2025
Listing #:X13098426
Property Type:Detached, 2-Storey
Building Age:100+
Size:3500-5000 feet²
Land Size:298 x 229 | .50-1.99 acres
Days on CPRB:
Garage:Detached 3 garage
Locker:None
On CPRB Since:
Listing Brokerage:Chestnut Park Real Estate

Details

Property

Property Type:Detached
Style:2-Storey
Community:Grey Highlands
Municipality:Grey County

Building

Size:3500-5000 feet²
Building Age:100+
Construction:Brick, Wood

Inside

Bedrooms:5
Bedrooms Above Grade:5
Bathrooms:4
Bathrooms Detail:1, 4pc Main floor
Bathrooms Detail:1, 3pc Main floor
Bathrooms Detail:1, 5pc Second floor
Bathrooms Detail:1, 2pc Second floor
Kitchens:1
Family Room:Yes
Appliances Included: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
Basement:Finished

Parking

Driveway:Private
Garage Type:Detached
Garage Spaces:3
Total Parking Spaces:13

Utilities

Cooling:None
Heating Type:Radiant
Heating Fuel:Propane
Utility Sewer:Septic

Highlights

Fireplace Type:Propane, Wood

Land

Cross Street:4th Concession B

$1,749,900

List price

553763 Road 55, Grey Highlands – 5 bed Detached for sale · MLS® # X13098426