139 South Shores Road

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.

Welcome to easy waterfront living on Lake Eugenia. Offered for sale by the original owners it has 135 feet of south-facing shoreline, 3500 sq ft of living space 4 bedrooms , 3 baths and bonus room. This family-friendly property features a gently sloping beach area, perfect for enjoying fun filled summer days by the water. Large windows fill the home with natural light, while the living room's vaulted ceilings and two-sided fireplace create a warm and inviting space. Sliding doors lead to a full-length deck where you can relax and take in the lake views. The dining room is generously sized for hosting family and friends, and the well-appointed kitchen features new appliances, plenty of cabinetry, and ample counter space. The lake-facing primary bedroom includes a walk-in closet and private ensuite, while two additional bedrooms are tucked into their own wing with a shared bathroom. The finished walk out basement extends the living space with a second kitchen, games area, third bathroom and fourth bedroom. A bonus room gives options for a hobby room or office. A double car garage with interior access from both the kitchen and basement adds everyday convenience. A welcoming Lake Eugenia home that combines beautiful frontage, sunny southern exposure, and space for family, friends, and fun.

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.