553763 Road 55
Grey Highlands, Grey Highlands, N0C 1J0
FOR SALE
$1,899,900
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BEDROOMS4
BATHROOMS1
KITCHENS10 + 1
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Property 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.
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Property Features
Golf, Level, School Bus Route, Skiing, 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, Private, Security System, Propane, Wood
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Property Details
Address
553763 Road 55
Community
City
Postal Code
N0C 1J0
Property Type
Detached, Detached
Zoning
Rural
Lot Size
298' x 229'
Acreage
1.6 Feet
Taxes
$7,812 (2025
Basement
Finished
Exterior
Deck, Landscaped, Porch, Year Round Living
Heat Type
Radiant
Heat Source
Propane
Water
Well
Parking Spaces
10
Garage Type
Detached
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Listing contracted with Chestnut Park Real Estate
Hidden country gem. Winding drive through trees ushers you to a wonderful country offering. Home completely redone and lovely addition built complete with wood burning fireplace, cathedrals, library, den, family room, rec room, 4+1 bedrooms, 4 baths, wood floors, verandahs, rear patios and fully landscaped. A shop/garage, large parking area and privacy in this 10+ setting. Will not disappoint! 6.4 acres that's hard to duplicate. Completion of severance pending.
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Brewster's Lake - over 200' waterfront with a bungalow, shop and garage on a 3.2 acre hardwood lot. Lake views from nearly every room in the home. Spacious rooms throughout the 2,500 square foot main level including open concept kitchen, dining and living areas with vaulted ceilings and a wood-burning fireplace. The walkout basement is fully finished with massive family room, office or 5th bedroom with ensuite; walkout to hot tub, patio and lakeside. SHOP 30x52 with in-floor heat, spray foam insulation, Trusscore interior, 3 roll up doors; detached single garage and attached double garage with in-floor heat. On demand hot water, generator back up, metal roof, new windows (2018), central air, water system, greenhouse, hot tub and more. The private waterfront boasts a sandy beach, dock and firepit. Four season living in a four season playground 20 minutes to Collingwood and Blue Mountain, 10 minutes to Devils Glen Country Club (private) and minutes away from year-round trails and recreational activities. Includes part ownership of additional waterfront lot.
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The "Westwind" Retreat is a one of a kind county estate tucked away on almost 16 acres of natural beauty. Completely out of sight from the main road, discover this serene property with it's beautiful 5 bedroom home with in-law suite, cultivated trails throughout the property, multiple outbuildings, 2 large ponds which flow into Little Beaver River, connecting to Lake Eugenia. From the moment you step onto its grounds, you are transported into a realm of enchantment and serenity that captures your imagination. This 5 bedroom chalet style home has a grand open living space, main floor primary bedroom with ensuite bath, 3 bedrooms on the upper level with 3 piece bath and a fully finished lower level with walkout and complete in-law suite featuring a separate kitchen. The home's architecture blends seamlessly with the natural surroundings. Enjoy truly spectacular sunsets off your back deck or back covered patio. Large windows offer panoramic views of the expansive ponds from every corner of the home while multiple outdoor seating areas bring you at one with nature. This property is more than just a place to live, it's a place to unwind, relax and call home. Fish from your own dock, take the kayak for a paddle and fall in love with this spectacular property. With year-round activities such as skiing at Beaver Valley/Devils Glen/Blue Mountain, snowmobiling, and golfing, this property is your gateway to Grey Highlands' all-season recreational paradise. Located just 5 minutes from Flesherton for all your day to day needs with Markdale Hospital close by, 35 minutes to Collingwood and Blue Mountain, and less than 2 hours from Toronto, this home makes for a rare getaway with endless possibilities. Discover the perfect blend of privacy, beauty, and convenience all in one property.
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