553763 Road 55
Grey Highlands, Grey Highlands, N0C 1J0
FOR SALE
$1,899,900
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BEDROOMS4
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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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Located along the historic Old Mail Road, this extraordinary 34.74-acre property has been cherished by the same family for over 40 years. A picturesque circular driveway, lined with mature fruit trees, leads to the original two-storey cottage, built in 1974. From its expansive windows and deck, the home captures sweeping views of the Beaver Valley and Escarpment, overlooking a stunning 60-foot spring-fed swimming pond.The original cottage offers a traditional layout with four bedrooms, two full bathrooms, a kitchen, and an open-concept living and dining area centered around a wood-burning fireplace. A practical mudroom/storage area complete the space. A thoughtfully designed addition, completed in 2004, provides a separate living area ideal for extended family or guests. This wing features a main-floor bedroom with a two-piece semi-ensuite, a spacious recreation room, and a charming screened-in porch. The main level features tons of windows and The lower level includes a full four-piece bathroom with laundry and two additional bedrooms.The grounds have been lovingly cultivated over the years and were once part of a 15-year forestry program The property showcases thousands of planted trees, including approximately 5,000 pines, along with apple and pear trees, spruce, cedar, and naturalized permaculture type gardens throughout (organic). Formerly operated as a garlic farm, the property includes a 25' x 12' drying shed along with four additional outbuildings. Recreational amenities abound, featuring a volleyball court, limestone tennis court, and cement shuffleboard court-making this a true haven for outdoor enthusiasts. Located 2 mins from Heathcote Village, 18 mins to Beaver Valley Ski Club & Blue Mountain Resort, 10 mins to dowtown Thornbury & 22 mins from downtown Collingwood this property is centrally located for all local amenities!
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Rare opportunity to own a true ski-in, ski-out chalet at the prestigious Beaver Valley Ski Club, ideally located in Beaver South. Privately set at the end of a quiet dead-end road, this custom-built chalet offers the perfect blend of luxury, warmth, and functionality. A spacious stone-floored foyer welcomes you into the stunning open-concept great room, featuring soaring vaulted tongue-and-groove pine ceilings, dramatic timber beams with metal hardware, oversized windows, and views of skiers on Southern Comfort. The floor-to-ceiling wood-burning fireplace with hand-laid stone serves as a striking centerpiece. The custom kitchen is designed for entertaining, with modern appliances, double sinks, and a large island that naturally becomes a gathering place for family and friends. A light-filled formal dining room with vaulted ceilings and solid wood floors opens to a sunny south-facing deck and a separate covered porch with hot tub provides the perfect après-ski retreat. The main floor includes a bedroom with access to a three-piece bath, ideal for guests or senior family members. Life is easy with a generous boot room with dedicated ski entry. Upstairs, the primary suite features vaulted ceilings, custom furnishings, and beautiful hardwood trim. Additional bedrooms include a spectacular bunk room with custom triple-stacked bunks, plus a spacious guest bedroom and shared three-piece bath. The lower level offers a large games and family room with a custom pool table convertible to ping pong, an additional flex room, and a third bathroom. Solidly built and thoughtfully detailed throughout, it comfortably sleeps 12 and comes furnished. A rare offering in one of Grey Highlands' most exclusive private ski communities.
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