$1,899,900
 $10,199 est/mo Sourced by Back At You

553763 Road 55,Grey Highlands, ON N0C 1J0

Grey Highlands, ON N0C 1J0

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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.

Details

MLS #X13098426
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
StatusNew
Year0
Days On Site107
Listing Provided ByChestnut Park Real Estate | X13098426 557206

Features

Bed(s)5
Bath(s)4
Garage3
BasementY
Story(s)2
Acreage1.57
Water FrontNone
Property ViewPasture

Interior

Interior FeaturesAuto Garage Door Remote, Bar Fridge, Central Vacuum, Generator - Partial, Propane Tank, Sauna, Separate Heating Controls, Water Heater Owned, Water Purifier, Water Softener, Water Treatment
CoolingNone
Heat SourcePropane
Fireplace FeaturesPropane, Wood
Fireplace Yes / NoYes

Exterior

Exterior FeaturesDeck, Landscaped, Porch, Year Round Living
RoofMetal
Foundation DetailsPoured Concrete, Stone
TopographyFlat, Open Space
ViewPasture
Construction MaterialsBrick, Wood
Security FeaturesSecurity System

Parking

Garage Yes / NoYes
Parking FeaturesPrivate

Utilities

SewerSeptic

Taxes

Tax Annual Amount7812
Tax Assessed Value553000
Tax Legal DescriptionPT LT 21 CON 4 OSPREY AS IN R45340; GREY HIGHLANDS
Tax Year2025

Area Information

ProvinceON
RegionGrey County
CityGrey Highlands
Postal CodeN0C 1J0
AreaGrey Highlands
Listing VS Median (in N0C 1J0)
Price:
$1,899,900
low | high
Med:
$0
On site:
107
low | high
Med:
Sourced by Back At You

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Additional Information


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Learn More About This Property

ProvinceON
RegionGrey County
CityGrey Highlands
Postal CodeN0C 1J0
AreaGrey Highlands
Listing VS Median (in N0C 1J0)
Price:
$1,899,900
low | high
Med:
$0
On site:
107
low | high
Med:
Sourced by Back At You
Listing Updated: August 7, 2026 at 6:40:05 PM PDT