Skip to content
EnterHomeREALTY 416-688-HOME
♡ Saved
← Back to resultsGrey Highlands / Property details
For sale · MLS® X13098426

553763 Road 55, Grey Highlands, ON N0C 1J0

Grey Highlands, ON N0C 1J0

$1,749,900Asking price
5 Bedrooms4 Bathrooms— Reported areaDetached Type

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 facts & features

Property type
Detached
MLS® number
X13098426
Source status
New
Bedrooms
5
Bathrooms
4
Reported interior area
Not provided
Neighbourhood
Not provided
Postal code
N0C 1J0
Parking spaces
13
Garage
Detached
Lot depth (source units)
229
Annual property tax
7812
Basement
Finished
Laundry
Not provided
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
Exterior features
Deck, Landscaped, Porch, Year Round Living

Values and units are reported by the listing source. Verify measurements and fees with the brokerage.

Floor plans & room measurements

Floor plans and verified room measurements are not available for this property.

Property value & listing history

Current authorized listing record

New · $1,749,900

Multi-event history, valuations and sold comparables require verified property identity and display permissions. No historical events or estimated values have been inferred.

Sign in to request eligible VOW access →

Plan your monthly ownership costs

Adjust the assumptions for your own scenario. Blank expenses are unknown; enter them for a fuller estimate.

Enter assumptions

Planning estimate with Canadian semiannual compounding. Excludes mortgage insurance, closing costs and special assessments. This is not a lender quote or mortgage approval.

Explore affordability & closing-cost tools →

Location & neighbourhood

A verified map location is not yet available for this listing.

Transit stops, schools and commute information are unavailable until verified sources are connected. Optional overlays remain off.

Explore active properties in Grey Highlands →

Listing brokerage: Chestnut Park Real Estate. Displayed by EnterHome Realty. Source: authorized IDX record, MLS® X13098426. Information deemed reliable but not guaranteed.

Request a showing