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553763 Road 55 N/A

Grey Highlands / Grey Highlands, ON N0C 1J0

ActiveFor Sale
5 Beds
4 Baths
3,500 Sq Ft
2 Lot Sq Ft
Single Family Home

About This Property

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.

Property Details

StatusActive
Property TypeSingle Family Home
Listing TypeFor Sale
Interior Size3,500 sq ft
Lot Size2 sq ft
Bedrooms5
Bathrooms4
Postal CodeN0C 1J0
Last UpdatedSep 14, 2026 · 11:00 a.m.

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Features & Amenities

  • View
  • Fireplace
  • Air Conditioning
  • Basement

TRREB MLS® Attribution

MLS® X13098426

Listed by Chestnut Park Real Estate

The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA. The trademarks REALTOR®, REALTORS® and the REALTOR® logo are controlled by CREA and identify real estate professionals who are members of CREA. Listing data provided by the Toronto Regional Real Estate Board (TRREB). The information contained herein is from sources believed to be reliable but is not guaranteed. Information deemed reliable but not guaranteed accurate by TRREB or Team Filipe / RE/MAX.

$1,749,900

asking price

MLS®X13098426
TypeSingle Family Home
CityGrey Highlands
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Team Filipe · RE/MAX · (647) 210-6070

Mortgage Estimate

Est. Monthly Payment

$8,545

/month · $1,399,920 mortgage

Down Payment20% — $349,980
Interest Rate5.5%

Amortization

Total Interest

$1,163,578

Total Cost

$2,563,498

Estimate only. Based on Canadian semi-annual compounding, 25-yr amortization at 5.5%.

Full Mortgage Calculator →

Listed By

Chestnut Park Real Estate