5 Ontario Properties Blending Heritage Charm with Modern Luxury and Expansive Grounds

Set against the rugged beauty of the escarpment in Barrow Bay, the “Rock House” is a captivating two-story stone cottage that has been a cherished family retreat for generations. Spanning 2.5 acres, this fully renovated estate showcases stunning stonework inside and out, with a thoughtfully designed flagstone patio offering a serene spot to soak in panoramic views of Georgian Bay. The property boasts 664 feet of deeded shoreline, complete with a shore well and a firepit perfect for stargazing under clear night skies. Inside, a warm great room welcomes you, flowing into a cozy living and dining area with a woodstove insert. The main floor also features a galley-style kitchen, two spacious bedrooms, a powder room, laundry amenities, and a three-piece bathroom, all enhanced by in-floor heating. Just a short drive from Lions Head and near the Bruce Trail, this unique haven on a quiet no-exit road offers tranquility and timeless charm.

Size: 2,000 – 2,500 sf

Situated just west of Trout Creek, Ontario, this sprawling 195-acre estate offers a rare blend of rural serenity and entrepreneurial potential with a turnkey 15,000+ tap maple syrup operation. At its heart lies a modern 1,300-square-foot home, featuring contemporary finishes, hardwood floors, four bedrooms, and two bathrooms, complemented by a fully finished walk-out lower level with an open-concept living space. The property’s 2,600-square-foot sugarhouse is equipped with cutting-edge technology, including a high-capacity evaporator and reverse osmosis system, ensuring efficiency for the certified organic operation. A picturesque three-acre pond and a rustic hunting camp add charm, while the surrounding maple-dominated forest sets a tranquil backdrop. With the option to expand to 4,000 additional taps on leased Crown Land, this estate promises a fulfilling lifestyle for families or seasoned producers seeking to immerse themselves in nature and industry.

Situated in the heart of historic Campbellville within the Town of Milton, this circa 1880 heritage gem seamlessly blends timeless charm with modern functionality. Thoughtfully renovated and impeccably maintained, the property boasts mixed-use zoning, making it a versatile haven for families, home-based businesses, or savvy investors. Spanning four levels above grade, the multi-generational layout offers two kitchens, three full bathrooms, and five bedrooms, ensuring ample space for diverse needs. Set on a sprawling 103’ x 186’ lot, the beautifully landscaped grounds feature terraces, a pergola, and a cozy fire pit. With ample parking, a workshop, and garage storage, practicality meets elegance. Directly across from conservation land and minutes from Hilton Falls and Kelso, outdoor enthusiasts will relish proximity to Ontario’s finest trails. Top-ranked schools and a tight-knit community further elevate the allure of this rare live/work sanctuary.

Size: Lot Size: 103.92 X 186.79

Perched atop a scenic mountain ridge, this luxury residence offers an elevated lifestyle with breathtaking views and unparalleled sophistication. Step inside to discover modern elegance, where high-end finishes and thoughtful design create a seamless flow. The main floor captivates with oversized tile flooring, a gourmet chef’s kitchen featuring top-tier Thermador and Fisher & Paykel appliances, and a striking two-story tiled fireplace in the great room. A serene primary suite indulges with a spa-like ensuite and custom walk-in closet, while an executive office exudes refinement with built-in cabinetry.

Size: 2,500 – 3,000 sf

Positioned along the serene shores of Six Mile Lake, this remarkable waterfront retreat at 285 A & B Crooked Bay Road offers a rare opportunity for multi-generational living or shared ownership. Boasting 280 feet of sandy shoreline with eastern exposure, the property captures breathtaking sunrises and provides deep dockside water for effortless boating. Two fully equipped cottages, totaling 4,185 square feet of finished living space, feature nine bedrooms, six bathrooms, and three kitchens, ensuring ample room for large families or guests. A spacious boathouse with three slips—two wet and one dry—complements a 535-square-foot garage for storing toys and tools. Just two minutes from Highway 400, this compound-style haven blends natural beauty with convenience, immersed in a close-knit community near full-service marinas. It’s an idyllic setting for creating lasting memories on tranquil waters.

Size: 3,500 – 5,000 sf