553763 Road 55
553763 Road 55
553763 Road 55
553763 Road 55
553763 Road 55
553763 Road 55
553763 Road 55
553763 Road 55
553763 Road 55
553763 Road 55
553763 Road 55
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553763 Road 55
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50 photos

553763 Road 55

Grey Highlands, Grey Highlands, ON
Listed 51 days ago
$1,899,900For Sale
$1,551,680Estimated value
5Bedrooms
4Bathrooms
3500-5000 sqftSize
13 (3 garage)Parking
298 ft × 229 ftLot Size
DetachedProperty Type

553763 Road 55

Grey Highlands, ON · Grey Highlands

Listed 51 days ago
Bedrooms5
Bathrooms4
Size3500-5000 sqft
Parking13 (3 garage)
Lot Size298 ft × 229 ft
Property TypeDetached
$1,899,900
For Sale
MLS# X13098426
$1,551,680Estimated value

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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 sp…

Features & Details

Property Type
Detached
Tax
$7,812 / 2025
Building Age
100+ years
Size
3500-5000 sqft
Lot Size
298 x 229 Feet
Basement Info
Finished
Total Parking Spaces
13 (3 Garage)
Title
Residential Freehold
Property Style
2-Storey
Community
Grey Highlands
Municipality
Grey Highlands
Construction
Brick, Wood
Cross Street
4th Concession B
Front Door Facing
East
Local Amenities
Golf, Level, School Bus Route, Skiing
Lot Legal Description
PT LT 21 CON 4 OSPREY AS IN R45340; GREY HIGHLANDS
Data Source
One Point Association of REALTORS
Brokerage
Chestnut Park Real Estate
Listed On
May 07, 2026
Listing Expires On
Aug 28, 2026
Listing Updated On
May 17, 2026
Bedrooms
5
Bathrooms
4
Kitchens
1
Rooms
10
Bathroom Detail
4 Pcs on Main Level
Bathroom Detail
3 Pcs on Main Level
Bathroom Detail
5 Pcs on 2nd Level
Bathroom Detail
2 Pcs on 2nd Level
Driveway
Private
Garage Type
Detached
Garage
3
Parking
13
Heating
Radiant
Heat Source
Propane
Cooling
None
Sewer
Septic
Den / Family Room
Yes
Fireplace
Propane, Wood
Swimming Pool
None
Roof Material
Metal
Foundation Type
Poured Concrete, Stone
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

Listing History

Active51 days on marketCurrently viewingMLS #X13098426
May 7, 20261 month ago
Listed for Sale
Sign in to view
Terminated170 days on marketMLS #X12210814
Nov 28, 20257 months ago
Terminated
Sign in to view
Jun 10, 20251 year ago
Listed for Sale
Sign in to view

Estimate History

Estimated value, last 24 months
Jul 2024 – Jun 2026
$1.72M
$1.52M
$1.31M
$1.1M
Jul
Dec
May
Oct
Mar
Jun

Automated estimate from Polsinello Predictive AI. Not an appraisal. Actual market value may differ.

Mortgage calculator

Estimated monthly payment
$9,269

Estimated payment. Does not include property tax, insurance, or condo fees.

Location & nearby

Grey Highlands Real Estate Market

Grey Highlands · last 90 days
$712,500
Median sold price
55 days
Avg days on market
46
Homes sold (90 days)
2%
Sold above asking
91%
Sold below asking
$498–$686/ft²
Price per sq ft
Median price trend
Jul 2025 – Jun 2026
$1.17M
$0.92M
$0.68M
$0.43M
Jul
Oct
Jan
Apr
Jun

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(905) 830-9111