553763 Road 55 Grey Highlands, ON N0C 1J0
Listing Courtesy of:  CREA / Listed By: Chestnut Park Real Estate

  553763 Road 55 Grey Highlands, ON N0C 1J0

Active (113 Days)
$1,899,900 (CAD)
5
BED
4
BATH

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. (id:41440)

MLS®:
X13098426
Taxes
$7,812(2026)
Type
Single-Family Home
County
Grey County

Listed By

Rob McAleer, Chestnut Park Real Estate
Source
CREA
Last checked Aug 28 2026 at 10:13 PM EDT
Bathroom Details
  • Full Bathrooms: 3
  • Partial Bathroom: 1
Interior Features
  • Washer
  • Refrigerator
  • Dishwasher
  • Microwave
  • Central Vacuum
  • Stove
  • Dryer
  • Window Coverings
  • Garage Door Opener
  • Garage Door Opener Remote(s)
  • Water Softener
  • Wine Fridge
  • Water Purifier
  • Water Treatment
  • Water Heater
Lot Information
  • Flat Site
  • Level Lot
  • Sauna
  • Open Space
Property Features
  • Fireplace: Total: 2
  • Foundation: Poured Concrete
  • Foundation: Stone
Heating and Cooling
  • Radiant Heat
  • Propane
  • None
Basement Information
  • Finished
  • N/a
Flooring
  • Hardwood
Exterior Features
  • Brick
  • Wood
Utility Information
  • Sewer: Septic System
Parking
  • Total: 13
  • Garage
  • Detached Garage
Stories
  • 2
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by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. Listing Data Last Updated: 8/28/26 15:13