Oakville’s highest sales of 2026 so far show a clear pattern: the very top of the market continues to be driven by rare South Oakville properties with exceptional land, privacy, lake exposure, and architectural significance. Waterfront and near-waterfront estates remain the clear standouts, while buyers at this level continue to place a premium on setting, scale, and long-term scarcity.
From landmark lakefront residences in Morrison to modern architectural homes in Old Oakville and Ford, these five sales reflect the strength of Oakville’s most established luxury neighbourhoods.
#1 - 21 Ennisclare Dr E
Sale Price: $12,600,000
Set on a rare 1.15-acre riparian lakefront lot in Morrison, 21 Ennisclare Dr E was the highest sale in Oakville so far in 2026. The property offered significant frontage, sweeping lake views, a large two-storey residence, finished walk-out lower level, inground pool, and the kind of land value that continues to define the upper end of the Oakville market.
Listed by: Canada Home Group Realty Inc.
#2 - 1092 Argyle Dr
Sale Price: $11,700,000
Located on a prized stretch of Lake Ontario shoreline in Morrison, 1092 Argyle Dr combined scale, architecture, and direct waterfront views. The estate featured over 14,000 square feet of finished living space, elevator access, multiple formal entertaining areas, a tennis court, terraces, and expansive lake-facing principal rooms.
Listed by: RE/MAX Escarpment Realty Inc.
#3 - 49 Cox Dr
Sale Price: $9,900,000
On one of South East Oakville’s most private lakefront streets, 49 Cox Dr offered nearly 9,300 square feet of finished living space on a 2.38-acre waterfront lot. With riparian rights, mature landscaping, a gated drive, pool, terraces, and lake views from many of the principal rooms, this sale reflects the ongoing demand for privacy and true waterfront land.
Listed by: Re/Max Hallmark Alliance Realty
#4 - 2250 Chancery Lane W
Sale Price: $7,500,000
2250 Chancery Lane W brought a more contemporary luxury offering to the list. Located in Ford with lake views, the home featured over 9,000 square feet of finished living space, modern interiors, an elevator, infinity pool, theatre, golf simulator, wine wall, exercise room, and multiple walkouts to outdoor entertaining areas.
Listed by: RE/MAX Escarpment Realty Inc., Brokerage
#5 - 116 Chartwell Rd
Sale Price: $7,000,000
Rounding out the top five, 116 Chartwell Rd stood apart as a modern, architecturally significant residence in Old Oakville. Built to Net-Zero specifications, the home combined sustainability, smart-home technology, geothermal systems, solar power, high-end finishes, a four-car garage, and a refined contemporary design in one of Oakville’s most established neighbourhoods.
Listed by: Sotheby’s International Realty Canada, Brokerage
While each property is different, the common thread is clear: Oakville’s top luxury buyers continue to focus on irreplaceable locations, oversized lots, lake views or waterfront access, privacy, and homes with either architectural pedigree or long-term land value. At the highest end of the market, scarcity remains one of the strongest drivers of value.
