Listed for:Listed May 7, 2026
$1,749,900

553763 Road 55

Grey Highlands, ON N0C 1J0

Detached House For Sale
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Sale & Price History for 553763 Road 55, Grey Highlands

No listing history available

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About 553763 Road 55, Grey Highlands

Summarized Description

  • Historic 1884 schoolhouse transformed into luxury estate.
  • Over 5,000 sq ft with modern upgrades.
  • Stunning great room with 22-foot ceilings.
  • Custom garage with heated floors and office space.
  • Located near parks, trails, and fine dining.
  • Ideal for entertaining or multi-generational living.
  • Private 1.57 acres with mature landscaping.

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.

Key Facts & Features

Property Costs

Annual Property Tax Amount
$7,812
Land Transfer Tax Fee
$31,473

Rental Items

Rental Equipment
Propane tank, security system.
Under Contract
Propane Tank, Security System

Basement Type
Finished

Interior Features

Laundry Level
Main Level
Interior Extras
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
View
Pasture
Security Features
Security System
Fireplace/Stove
Yes
Fireplace Features
Propane, Wood
Elevator
No

Exterior Features

Exterior Extras
Deck, Landscaped, Porch, Year Round Living
Pool
None
Property Features
Golf, Level, School Bus Route, Skiing

Building

Building Type
Detached
Building Style
2-Storey
Approx Age
100+

Construction

Exterior Finish
Brick, Wood
Roof
Metal
Foundation Details
Poured Concrete, Stone
Special Designation
Unknown

Lot

Lot Front
298.00 ft
Lot Depth
229.00 ft
Lot Size
1.575
Lot Shape
Rectangular

Inclusions

Inclusions
Pool table & cue rack with cues, Pool table cover, TV & bracket in Primary Bedroom, All built in cabinetry in garage, car lift, 3 Sheds, GDO's x 2, Basement TV, Sound bar & bracket, F/P toolholder, compressor in garage, Central vacs. Built-in Microwave, Dishwasher, Dryer, Garage Door Opener, Refrigerator, Stove, Washer, Hot Water Tank Owned, Window Coverings, Wine Cooler

Exclusions

Exclusions
Shelving in laundry room, Tall wall cabinet in Family room, freezer in basement, refrigerator in garage, TV in garage, wall mounted bookshelf in kitchen, All bathroom mirrors.

Parking & Garages

Garage Type
Detached
Garage Spaces
3
Parking Spaces
10
Total Garage And Parking Spaces
13

Heating & Cooling

Heat Source
Propane
Heat Type
Radiant
Air Conditioning
None
Water
Well
Sewers
Septic
Hydro
Yes
Cable
Yes
Telephone
Yes

Bedrooms
5
Washrooms
4
Kitchens
1
Family / bonus room
Yes

Room sizes

  • Great Room—
    Main level, Gas Fireplace, Cathedral Ceiling(s)
  • Sunroom—
    Main level
  • Kitchen—
    Main level, Combined w/Dining, Hardwood Floor, Cathedral Ceiling(s)
  • Family Room—
    Main level, Hardwood Floor, Cathedral Ceiling(s)
  • Bedroom—
    Main level
  • Primary Bedroom—
    Second level, 5 Pc Ensuite, Hardwood Floor
  • Bedroom—
    Second level, Hardwood Floor
  • Bedroom—
    Second level, Hardwood Floor
  • Bedroom—
    Second level
  • Loft—
    Second level
  • Family Room—
    Basement level

Washrooms

  • 4-piece, Main
  • 3-piece, Main
  • 5-piece, Second
  • 2-piece, Second

Municipality
Grey Highlands
Neighbourhood
Grey Highlands
Main cross streets
4th Concession B
Zoning
Rural
Directions
https://maps.app.goo.gl/oyWhiAutWKorQaSEA
Waterfront
None

MLS® number
X13098426
Data source
Toronto Regional Real Estate Board
Listed on
2026-05-07
Updated on
2026-09-09
Days on market
165 days
Possession date
2026-06-24
Possession type
1-29 days
Co-op commission
2.5% + tax
Seller
Listed by
Chestnut Park Real Estate

Home Market Value

Current home valuation for 553763 Road 55, Grey Highlands, Grey Highlands, ON. Listed for $1,749,900

HOMEH Estimate

?

$2,099,880

Estimated Sales Range

?

$1,259,928 - $2,939,832

HOMEH Estimate for 553763 Road 55, Grey Highlands

Calculated with a real agent's CMA method — 45+ years of experience, codified. Not an AI guess.

$2,099,880Low confidence
Based on 13 comparable properties
− $349,980 (17%) below our estimate — Good deal!
See the full analysisFree Every recent nearby sale behind this number

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Mortgage Payment Calculator

Compare up to 4 down payment scenarios

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Grey Highlands, ON
Minimum Down Payment Required:20.0%

20% required for homes $1.5M or more

Minimum down payment

$349,980

Scenario 1 Scenario 2 Scenario 3 Scenario 4
−Down payment
%
$
%
$
%
$
%
$
+CMHC insurance
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=Total mortgage
$1,399,920$1,312,425$1,224,930$1,137,435
Amortization
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%
%
%
%
Payment frequency
=Mortgage payment
$6,835monthly$6,408monthly$5,981monthly$5,554monthly
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Land Transfer Tax

Provincial

$31,473

Total Land Transfer Tax

$31,473

Around this home

3/100Almost All Errands Require a Car
0/100Minimal Transit
0/100Not rated
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5.8 /10

Grey Highlands

Public·secondary·270m

3.2 /10

Macphail Memorial

Public·elementary·280m

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