A pic from outside/outdoor area/front of a property/back of a property/a pic from drone, street for 553763 Road 55, Grey Highlands Ontario N0C 1J0
5 days on Market

553763 Road 55, Grey Highlands, Ontario N0C 1J0

Detached
5
5
~3500-5000 sqft
$1,899,900
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Detached
5
5
~3500-5000 sqft

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Highlights

Property Estimate

Days on market5 days

Estimated valueNot available

Price/Sqft$461/sqft

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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.


Property Details

Style2-Storey
ViewPasture
Age of property100+
SqFt~3500-5000 SqFt
Lot Size68,242 SqFt(229 x 298)
Parking Spaces13
MLS ®NumberX13098426
Community NameGrey Highlands
Data SourceTRREB
Listing byChestnut Park Real Estate

Features

Heating: Radiant
Central Vacuum
Fireplace
Basement: Finished

Main Floor

Great Rm

13.1 x 4.11

Gas Fireplace / Cathedral Ceiling

Sunroom

6.55 x 3.32

Kitchen

8.86 x 4.51

Combined W/Dining / hardwood floor / Cathedral Ceiling

Family

4.11 x 3.4

hardwood floor / Cathedral Ceiling


Features

Lot size: 68,242 SqFt

Parking

Garage spaces 3

Garage type Detached

Other parking spaces 10

Total parking spaces 13


Property listed by Chestnut Park Real Estate, Brokerage
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Market Data - Grey Highlands

Geo Zone Map ThumbnailGrey Highlands

Strong Buyer's Market

View Market Data

Detached house - for the past 30 days

Buyer's market Seller's market

Avg. Days on Market

Past 30 days

54 days

Compared to

2025

84 days

2024

69 days

2023

60 days

New Listings

Past 30 days

37 listings

Compared to

2025

35 listings

2024

48 listings

2023

35 listings

Units sold

Past 30 days

11 units

Compared to

2025

11 units

2024

19 units

2023

20 units

Median Sold Price

Past 30 days

$725,000

Compared to

2025

$670,000

2024

$585,000

2023

$500,000


Population and Demographics

Overview

Total population 10107
Average household income $123,530

Age (%)

0 to 19
23%
20 to 34
15%
35 to 49
15%
50 to 64
23%
65 and plus
24%

Household composition (%)

Single family
70%
Single person
26%
Multi person
3%
Multi family
1%

Mother tongue (%)

English
87%
Pennsylvania German
6%
German
3%
Others
3%
Dutch
2%

House tenancy (%)

Owners
87%
Renters
13%

What’s nearby?Essentials within 5 km

Local Logic

Transportation Scores

Estimated Budget