$1,899,900
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553763 Road 55, Grey Highlands, ON N0C1J0

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5 Beds
4 Baths
- Sq Ft

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. (id:58753)

Listing By: ROB MCALEER - Chestnut Park Real Estate cncrea2 Realty.com
  • MLS® X13098426
  • Date Listed05/07/2026
  • Days on Realty 30 Days
  • Bedrooms 5
  • Bathrooms 4 baths
  • Lot Size -
  • Sewer Septic Tank
  • Property Type Single Family Residence
  • Water Well

Interior Features

  • Appliances Washer, Refrigerator, Water purifier, Water softener, Central Vacuum, Dishwasher, Wine Fridge, Stove, Dryer, Microwave, Water Treatment, Window Coverings, Garage door opener, Garage door opener remote(s), Water Heater
  • Flooring Hardwood
  • Cooling None
  • Heating Radiant heat, Propane

Exterior / Lot Features

  • Roof -
  • Lot Size Acres -
  • Lot Size SQFT -
  • Lot Features Level lot, Open space, Flat site, Sauna

Directions

Cross Streets: 4th Concession B. ** Directions: https://maps.app.goo.gl/oyWhiAutWKorQaSEA.

Sales & Tax History

Source: Public Records

Local Neighborhood Highlights for N0C1J0

Discover key demographics, population statistics, and environmental insights for the Grey Highlands, ON area.

Walkability in ON / N0C1J0

Source: Walk Score

1/100

Car-Dependent

Walk Score ®

0/100

Minimal Transit

Transit Score ®

11/100

Bikable

Bike Score ®

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 1/100, Transit Score: 0/100, Bike Score: 11/100.

Points of Interest near 553763 ROAD 55, Grey Highlands, ON N0C1J0

Frequently Asked Questions for 553763 ROAD 55

Source: Realty.com

553763 ROAD 55, Grey Highlands, ON N0C1J0 in Grey Highlands, ON N0C1J0 is a single family residence listed at $1,899,900. Highlights include 5 bedrooms, 4 bathrooms. Realty.ca has 50 photos, sales history, school insights, and mortgage tools for this listing.

Realty.com has 50 photos of 553763 ROAD 55.

The full address for this home is 553763 ROAD 55, Grey Highlands, ON N0C1J0.

553763 ROAD 55 has been listed on Realty.com since Thu May 07, 2026

The average walkability score in the surrounding area is Walk Score: 1/100, Transit Score: 0/100, Bike Score: 11/100.

Listing provided courtesy of: Chestnut Park Real Estate
Listing agent: ROB MCALEER

This content last refreshed on 2026-06-06 11:52:16. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.