553763 Road 55 N/A, Grey Highlands, ON

Grey Highlands, Grey Highlands Hood
4th Concession B
5 Br | 4 Bath | 3500-5000 Sqft
$1,899,900 For Sale

Property Overview

  • Detached — 2-Storey
  • SqFt: | 3500-5000 Sqft
  • Lot Size: 298.00 x 229.00 Feet
  • Age: 100+ Years
  • Basement: Finished
  • Exterior: Brick, Wood
  • Taxes: 7,812 / 2025
  • Zoning: n/a
  • MLS #: X13098426
  • Water: Drilled Well
  • Sewer: Septic
  • Heat Source: Propane , Radiant

Property 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.

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

Property Details

  • For: For Sale
  • Type: Detached
  • Style: 2-Storey
  • Lot: 298.00 x 229.00 Feet
  • Region: Grey County
  • Hood: Grey Highlands
  • Zoning: n/a
  • Lot Irreg: Fronting on: East
  • Fronting On: East

Building Details

  • Age: 100+ Years
  • Exterior: Brick, Wood
  • Heat: Propane , Radiant
  • A/C: None
  • 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
  • Pool: None
  • Water: Drilled Well
  • Sewer: Septic
  • Garage: Detached
  • Total Parking: 13.00
  • Driveway: Private

Property Interior

  • Sqft: 3500-5000 Sqft
  • Bed: 5
  • Bath: 4
  • Kitchen: 1
  • Family Room: No
  • Basement: Finished
Rooms Details

Great Room

Main Level

13.1 x 4.11

Gas Fireplace, Cathedral Ceiling(s)

Sunroom

Main Level

6.55 x 3.32

Kitchen

Main Level

8.86 x 4.51

Combined w/Dining, Hardwood Floor, Cathedral Ceiling(s)

Family Room

Main Level

4.11 x 3.4

Hardwood Floor, Cathedral Ceiling(s)

Bedroom

Main Level

3.76 x 3.4

Primary Bedroom

Second Level

4.63 x 3.99

5 Pc Ensuite, Hardwood Floor

Bedroom

Second Level

3.18 x 2.91

Hardwood Floor

Bedroom

Second Level

3.18 x 2.96

Hardwood Floor

Bedroom

Second Level

7.31 x 2.73

Loft

Second Level

4.98 x 2.82

Family Room

Basement Level

8.66 x 6.46

Property Listed by: Chestnut Park Real Estate
Virtual Tour: n/a

Home Valuation Estimate

What is 553763 Road 55 N/A, Grey Highlands, ON worth in today’s Grey Highlands, Grey Highlands market?

This HomeZira valuation preview helps buyers and sellers think through the asking price for this 5-bedroom Detached with 3500-5000 sq. ft. in Grey Highlands, Grey Highlands. The full estimate reviews the property’s location, home type, bedroom count, size range, age, and nearby comparable market activity after sign-in.

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Location

  • Address: 553763 Road 55 N/A
  • Neighborhood: Grey Highlands
  • Zip/Postal Code: N0C 1J0
  • Nearby Amenities: Golf, Level, School Bus Route, Skiing
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About 553763 Road 55 N/A, Grey Highlands, ON N0C 1J0, Grey Highlands

Located at 553763 Road 55 N/A, Grey Highlands, ON in Grey Highlands (Grey Highlands neighbourhood), near 4th Concession B. This freehold home offers Detached, ["2-Storey"], 5 bedrooms, 4 bathrooms and 3500-5000 sq.ft. (approx.) in a layout suited to everyday family living. Basement: Finished • 13 parking spots • Garage: Detached • Heating: Propane Radiant • Cooling: None. Property taxes are approximately $7,812 for 2025. 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 a.

FAQs for 553763 Road 55 N/A, Grey Highlands, ON , Grey Highlands , Grey Highlands

What are the listing details for 553763 Road 55 N/A, Grey Highlands, ON?
553763 Road 55 N/A, Grey Highlands, ON is a Detached for sale in Grey Highlands, in the Grey Highlands neighbourhood, Grey County. The current list price is $1,899,900. MLS number: X13098426.
How many bedrooms and bathrooms does this home have?
553763 Road 55 N/A, Grey Highlands, ON is listed as a Detached with a ["2-Storey"] style, featuring 5 bedroom(s) and 4 bathroom(s). The listed interior size range is 3500-5000 sq. ft..
What lot, basement, garage, or parking details are listed?
The lot size is listed as approximately 298.00 x 229.00 Feet. The basement is listed as: Finished. Garage type: Detached. Total parking: 13 space(s).
What heating, cooling, and exterior details are shown?
Heating is listed as: Propane, Radiant. Cooling is listed as: None. Exterior/construction materials are listed as: Brick, Wood .
Where is this property located?
553763 Road 55 N/A, Grey Highlands, ON is located in the Grey Highlands neighbourhood of Grey Highlands. The listed cross street is 4th Concession B.
What information is available on this public listing page?
The public listing page shows current active listing information, property photos, room details when available, map location, listed price, property features, and contact options. Annual taxes are listed as $7,812 / 2025. Valuation tools and similar sold-property previews are available after sign-in where applicable, without displaying sold data in this public FAQ.

FAQ content is based on current active listing fields shown on this page. Sold prices, sold comparables, and VOW-only details are not included in this public FAQ.