5 Ontario Estate Homes and Heritage Country Retreats Under $4M

Set on 18 acres in Port Hope, Durham House traces its heritage to 1820, established by the Massey family and meticulously preserved as a 5,300-square-foot sanctuary where 19th-century elegance meets 21st-century comfort. Century-old trees frame rolling lawns and formal gardens, while inside, soaring ceilings and rich period details elevate the principal rooms, including a private library and a formal dining room made for unhurried hosting. A chef’s kitchen anchors daily life with an oversized island and a sun-drenched breakfast area. The light-filled sunroom looks out to a sprawling pool and manicured grounds, echoing the spirit of garden-party entertaining. Beyond the main house, a reclaimed historic barn has been transformed into a guest cottage or creative studio. A 7-acre river-fed pond, private dock, and boathouse complete the setting for quiet afternoons on the water.

Size: 18.00 acres

Surrounded by nearly 99 acres of productive farmland, this five-generation family farm pairs long-held stewardship with a practical, spacious residence. Built in 2001, the brick bungalow offers 3+ bedrooms, 4 baths, and more than 4,600 square feet of living space designed for flexibility across daily life and extended stays. A walk-out basement lends itself to a generous in-law suite or potential rental income, while two laundry rooms keep routines efficient on busy farm days. An attached two-car garage connects directly to both levels, simplifying everything from groceries to gear. Extensive outbuildings broaden the possibilities for storage, hobbies, or additional income opportunities. Set along a paved road in Erin, the property is conveniently located near Highway 401, Guelph, Milton, Rockwood, and GO Train service—balancing rural space with everyday reach.

Size: 98.89 acres

Set on A2 agricultural land bordering the planned growth boundary of Moffat in the Town of Milton, this property balances working countryside with space to roam. A long driveway leads to a potential residential and farm building site, while the acreage unfolds in a compelling mix of cultivated fields, hay, and mixed forest. Approximately 80 acres are in hay and cash crop–producing farmland, complemented by roughly 30 forested acres suited to recreational use and quiet walks at the edge of the treeline. Practical advantages include CLTIP and OFA credits that help reduce property taxes, plus a paved-road approach with proximity to Highway 401 and essential services. It’s a setting designed for days shaped by the land—productive, private, and thoughtfully connected.

Size: 115+ acres

Set on a private, wooded lot in London, this extraordinary bungaloft pairs architectural detail with a highly functional layout. Twelve-foot ceilings, walnut flooring, and high-end finishes set a refined tone, while tray and coffered ceilings, solid core doors, transom windows, and high baseboards bring texture and light throughout. The main-floor principal suite feels quietly removed, with garden doors to the rear yard and a marble-tiled ensuite featuring inlay, a freestanding tub, glass-enclosed shower, dual vanities, and a walk-in closet with custom built-ins and dual access. Entertaining flows from a kitchen with Wolf appliances, farmhouse sink, pot filler, and a large island to an adjacent servery with added appliances and a secondary sink. Two mudrooms, two fireplaces, a loft, and a two-tier backyard with covered porch round out daily life with ease.

Set within a highly sought-after estate community in Springwater, this residence speaks directly to nature lovers, pairing a practical layout with an everyday connection to the outdoors. Step inside and you’re immediately met with gorgeous forest views—an ever-changing backdrop that brings a sense of calm to daily life. The interior is thoughtfully arranged to accommodate a multitude of needs, making it easy to imagine spaces that flex with the rhythms of work, gathering, and quiet downtime. More than simply a place to live, the setting and layout lean into a lifestyle shaped by privacy, scenery, and the simple pleasure of looking out to the trees. It’s a home that invites slower mornings, unhurried evenings, and a constant awareness of the natural world just beyond the windows.