553763 Road 55 N/A

Grey Highlands, Ontario N0C 1J0

Overview

At a glance

Days on market172 days
ListedMay 7, 2026
UpdatedSep 9, 2026
Building age100+ years
Size3500-5000 sq ft
Lot298 x 229 Feet
Property taxes$7,812 (2025)
Parking13 spaces
BasementFinished
MLS® numberX13098426
Data sourcePropTx MLS® System
Listing brokerageChestnut Park Real Estate

About this home

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

Property

Style
2-Storey
Building age
100+
Fronting on
East
Cross street
4th Concession B
Community
Grey Highlands
Municipality
Grey Highlands

Inside

Bedrooms above grade
5
Bathrooms
4
Kitchens
1
Basement
Finished
Family room
Yes
Fireplace
Propane, Wood
Interior features
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

Utilities

Heating
Radiant
Heating fuel
Propane
Cooling
None
Water
Drilled Well
Sewer
Septic
Electricity
Yes
Cable
Yes

Building

Construction
Brick, Wood
Foundation
Poured Concrete, Stone
Roof
Metal
Exterior features
Deck, Landscaped, Porch, Year Round Living
Pool
None

Parking

Garage
Detached
Parking spaces
10
Total parking
13
Driveway
Private

Land

Frontage
298
Depth
229
Lot size units
Feet
Lot size (acres)
.50-1.99
Waterfront
No
Topography
Flat, Open Space
Property features
Golf, Level, School Bus Route, Skiing
Rooms (11)
RoomLevelSizeFeatures
Great RoomMain13.1 x 4.11Gas Fireplace, Cathedral Ceiling(s)
SunroomMain6.55 x 3.32
KitchenMain8.86 x 4.51Combined w/Dining, Hardwood Floor, Cathedral Ceiling(s)
Family RoomMain4.11 x 3.4Hardwood Floor, Cathedral Ceiling(s)
BedroomMain3.76 x 3.4
Primary BedroomSecond4.63 x 3.995 Pc Ensuite, Hardwood Floor
BedroomSecond3.18 x 2.91Hardwood Floor
BedroomSecond3.18 x 2.96Hardwood Floor
BedroomSecond7.31 x 2.73
LoftSecond4.98 x 2.82
Family RoomBasement8.66 x 6.46
Value

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History

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Community

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Costs

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Every monthEstimate
Mortgage payment$0
Property tax$0
Monthly total$0
At closing
Ontario land transfer tax$0

Estimates only, not financial advice. Uses Canadian semi-annual compounding, the minimum down payment and mortgage insurance rules, and Ontario’s land transfer tax brackets. Your lender and lawyer confirm the real numbers. Legal fees, title insurance and moving costs aren’t included.

Listing courtesy of Chestnut Park Real Estate. Listing information from the PropTx MLS® System. Each listing shows the brokerage that represents it. 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 by PropTx. Last updated October 27, 2026 at 10:53 a.m.

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