5 Ontario Retreats from Lake Simcoe to Toronto Skyline Views

Along the quiet end of Brambel Road in Shanty Bay, Oro-Medonte, this private woodland retreat unfolds across a serene 2-acre setting with access to Lake Simcoe. The home spans over 2,200 sq. ft., blending rustic charm with modern touches—hardwood floors, a bright updated kitchen, main-floor laundry/mudroom, and an updated ensuite across 3 bedrooms and 3 bathrooms. A newly finished 784 sq. ft. lower level (2023) adds flexible living with a games room, office, and cozy TV lounge. Outdoors, a wraparound cedar porch frames lake views, while a screened-in porch with a built-in BBQ kitchen sets the stage for easy entertaining. A 22×22 century log cabin studio offers guest, workshop, or creative space, and the sports court brings basketball, tetherball, oversized chess, and checkers into everyday life.

Size: 2,000 – 2,500 sf

Set back at the end of a long laneway, this 95+ acre farm just north of Rice Lake in Bailieboro is defined by scenic views and deep privacy. The land balances 70 workable acres of Otonabee loam soil with a 7-acre pasture, a 10-acre old heritage apple orchard, and additional lawn space, woodlot, and a plantation west of the home for wind and noise buffering. At its heart, an all-brick custom bungalow offers hardwood floors, a bright kitchen with custom butternut cabinetry and a centre island, and an open dining area that flows into a cozy living room anchored by an energy-efficient brick trombe wall. A den/office opens to a large composite deck with southern exposure, while the walk-out lower level adds extensive living space and in-law potential. Mature perennial gardens, an above-ground pool, a barn, and thoughtful updates round out a quietly complete rural setting.

Size: 1,100 – 1,500 sf

Along the water’s edge on the Petawawa River, this exceptional custom-built residence unfolds across 2.36 acres with approximately 300 feet of private waterfront shoreline. Set well back from the road, it offers a rare sense of privacy while delivering more than 4,000 square feet of bright, spacious living areas. A grand foyer introduces the home’s striking post-and-beam construction, echoed by large windows that frame views of the river, a pond, and established gardens. The living room pairs new hardwood flooring with a beamed ceiling, while a fully upgraded kitchen supports everyday ease and entertaining alike. A refurbished stone fireplace, now converted to gas, anchors the interior with warmth. Upstairs, hardwood and newly installed high-quality LVF flooring meet new pot lights and updated lighting, and a reconstructed catwalk adds a polished finishing touch. A fully renovated 940-square-foot auxiliary building provides additional recreational space, rounding out a setting designed for unhurried days by the water.

Size: 3,500 – 5,000 sf

Along the water’s edge at Harbour Square, this residence pairs a generous 1,722-square-foot layout with brand new hardwood floors (March 2026) and an open-concept kitchen centered around an island. Two bedrooms plus a den/family room give the plan flexibility—easy to live in day to day, and equally comfortable for entertaining. City views take the spotlight, with a welcome glimpse of the lake as well.

Size: 1,600 – 1,799 sf

Set on 99 acres in Grey Highlands, this country retreat pairs wide-open land with direct access to the Old Baldy Conservation Area and the Bruce Trail. Rolling pastures give way to a tranquil pond and maple forests, all stitched together by a newly built trail network for hiking, cross-country skiing, snowshoeing, or ATVing. The 2+1 bedroom, 2-bath cabin serves as a comfortable home base today, with room to imagine a future country estate. A versatile mix of outbuildings—including a Quonset hut with a new concrete pad, a classic bank barn, and a garage—supports everything from storage to studio or farm use. Minutes from Kimberley, Beaver Valley Ski Club, and Blue Mountain, the setting delivers sweeping valley views, magical sunsets, and an easy rhythm shaped by the outdoors.

Size: 700 – 1,100 sf