For Sale: 553763 55 Road, Grey Highlands, ON - REW
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$1,899,900
5 bd • 4 ba • 3500 - 4999 sf • House
553763 55 Road
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$1,899,900
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553763 Road 55Grey Highlands, ON, N0C 1J0

Rural Grey Highlands
  • 5 Bed
  • 4 Bath
  • 3500 - 4999 Sqft
  • House

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. (id:63626)
Listed by: ROB MCALEER, Salesperson, Chestnut Park Real Estate

Home facts and features

Price details
List Price
$1,899,900
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Gross Taxes for 2026
$7,812
Home facts
Bedrooms
5
Full Bathrooms
3
Partial Bathrooms
1
Parking Spaces
13
Parking Details
Detached Garage, Garage
Property Type
House
Depth
229 feet
Frontage
298.0 feet
Title
Freehold
Exterior Finish
Wood, Brick
Heating Type
Radiant heat, Propane
Basement Details
Finished,
Features
Fireplace(s), Flat site, Level lot, Open space, Sauna, Security system, Separate Heating Controls
Appliances
Central Vacuum, Dishwasher, Dryer, Garage door opener, Garage door opener remote(s), Microwave, Refrigerator, Stove, Washer, Water Heater, Water Treatment, Water purifier, Water softener, Window Coverings, Wine Fridge
Community
Agent details
Primary Agent
ROB MCALEER
Primary Broker
Chestnut Park Real Estate
Secondary Agent
JEFF MCALEER
Secondary Broker
Chestnut Park Real Estate
Listing details
Days on REW
30 Days
MLS® Number
X13098426
Source
Canadian Real Estate Association
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Property Insights

Osprey Central School
  • Public
  • JK - 8
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Call Agent
Salesperson
ROB MCALEER
Phone:
(705) 445-5454
Cell:
705-888-3981
Office:
705-445-5454
Salesperson
JEFF MCALEER
Phone:
(705) 351-2738
Cell:
705-351-2738
Office:
705-445-5454
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