553763 Road 55, Grey Highlands, ON N0C 1J0
Grey Highlands · Near 4th Concession B · View map
About this home
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.
The home
- Type
- 2-storey detached home
- Style
- 2-Storey
- Square footage
- 3500-5000 sq ft
- Bedrooms
- 5
- Bathrooms
- 4
- Kitchens
- 1
- Rooms
- 10
- Basement
- Finished
- Lot size
- 298 x 229 ft
- Faces
- East
- View
- Pasture
- Approximate age
- 100+ years
Ownership & fees
- Ownership
- Freehold
- Monthly condo fee
- None
- Security
- Security System
- Exterior
- Brick, Wood
Heating & cooling
- Heating fuel
- Propane
- Heating type
- Radiant
- Fireplace
- Yes
- Central vacuum
- Yes
Garage & parking
- Garage
- Detached
- Garage spaces
- 3
- Driveway spaces
- 10
- Total parking
- 13
- Parking features
- Private
Taxes & other
- Property taxes
- $7,812/yr
- Tax year
- 2025
- Occupancy
- Owner
- Possession
- ASAP
- Cross street
- 4th Concession B
- Neighbourhood
- Grey Highlands
More
- Price per sq ft
- ~$412 (at 4,250 sq ft)
- MLS® number
- X13098426
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The home and its surroundings
- 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
- Golf
- Level
- School Bus Route
- Skiing
- Deck
- Landscaped
- Porch
- Year Round Living
- Mortgage
- Property tax
- Maintenance fee
Cash needed to close
Estimates only, using Canadian semi-annual compounding, Ontario land transfer tax. Mortgage default insurance is added when you put down less than 20%. Your lender and lawyer will confirm exact numbers.
553763 Road 55 N/A, Grey Highlands, ON N0C 1J0
Grey Highlands · Near 4th Concession B
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Listing history for 553763 Road 55 N/A
See what this home and others at the same address were listed for, what they sold for, and how long it took.
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Frequently asked questions about 553763 Road 55
Answers come straight from this home’s MLS® listing.
How much is 553763 Road 55 listed for, and what would it cost each month?
553763 Road 55 is listed for $1,749,900. With 20% down ($349,980), the mortgage payment would be roughly $7,059 a month at 4.5% over 30 years. Add property tax and the estimate comes to about $7,710 a month, all in. That figure is an illustration, not a quote.
Is 553763 Road 55 freehold or a condo, and is there a monthly fee?
553763 Road 55 is a 2-storey detached home in Grey Highlands. Ownership is freehold: you own the home and the lot. There is no monthly condo fee, so the roof, windows, driveway, snow and lawn are yours to look after.
How many bedrooms and bathrooms does 553763 Road 55 have?
553763 Road 55 has 5 bedrooms and 4 bathrooms.
Does 553763 Road 55 have a garage and parking?
Yes. The listing shows the garage as detached, with room for 3 cars. The driveway adds 10 spaces. In total the listing counts 13 parking spaces.
Does 553763 Road 55 have a finished basement?
The listing describes the basement as finished. Finished basement space is usually not counted in the square footage shown.
What style of home is 553763 Road 55?
553763 Road 55 is a 2-storey detached home. A 2-storey detached house has its living space on the main floor and the bedrooms upstairs, on its own lot with no shared walls.
How big is 553763 Road 55, and what is the lot size?
The listing puts the home between 3,500 and 5,000 sq ft. The board reports a range rather than an exact figure, and it usually leaves out the basement. The lot is listed as 298 x 229 ft.
How is 553763 Road 55 heated and cooled?
Heating is radiant (propane). The listing does not show air conditioning.
What are the property taxes for 553763 Road 55?
Property taxes are $7,812 a year (2025), or about $651 a month.
Where is 553763 Road 55?
553763 Road 55 is in Grey Highlands. The nearest main intersection is 4th Concession B. The postal code is N0C 1J0.
Is 553763 Road 55 still for sale?
Yes. It is an active listing (MLS® X13098426). Listings here update from the board through the day and come down once a home sells.
What are similar detached homes near 553763 Road 55 asking?
Similar detached homes for sale nearby right now include 222 Plantt's Point Road at $1,499,900 (5 bed), 129 Blue Jay Crescent at $1,298,000 (5+2 bed) and 123 Lakeview Road at $1,699,900 (4+1 bed). These are asking prices, not sold prices. The Sold history tab shows what homes at this address went for.
What have homes at 553763 Road 55 N/A sold for?
Recent sales, leases and expired listings for this home and others at the same address are in the Sold history tab, with the price and date of each. It is free for members.
How do I book a showing at 553763 Road 55?
Pick a day and time with Book a Tour on this page. Tours are free, with no obligation, in person or by video. You can also call or text 647-931-3923.
Have a different question? Ask about this home and get an answer, usually within the hour.
Similar detached homes nearby
More detached homes for sale near Grey Highlands, picked by style, size and price.
2-storey detached home$1,499,900222 Plantt's Point Road, Grey Highlands5 bed · 2 bath · Grey HighlandsCourtesy of: Forest Hill Real Estate Inc.View home →
2-storey detached home$1,298,000129 Blue Jay Crescent, Grey Highlands5+2 bed · 4 bath · Grey HighlandsCourtesy of: RIGHT AT HOME REALTYView home →
2-storey detached home$1,699,900123 Lakeview Road, Grey Highlands4+1 bed · 3 bath · Grey HighlandsCourtesy of: Royal LePage RCR RealtyView home →Courtesy of: Chestnut Park Real Estate
Listing information comes from the Toronto Regional Real Estate Board through PropTx and is deemed reliable but is not guaranteed accurate. It is provided for consumers' personal, non-commercial use. 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.
*Estimated monthly cost assumes 20% down, a 4.5% rate and a 30-year amortization, plus property tax. For illustration only.