Oakville has long been one of Canada’s most coveted addresses for luxury living, and 2025 is proving no different. From glamorous waterfront estates to architectural masterpieces in Old Oakville, some of this year’s biggest transactions showcase the very best of design, lifestyle, and location. Here are Oakville’s five most expensive homes sold so far this year.
1. 27 Park Avenue — $10,100,000
Where the Hamptons meet Lake Ontario. Designed by Gus Ricci with interiors by Studio H, this Orchard Beach estate spans over 10,000 sq. ft. and is packed with jaw-dropping amenities. Think infinity pool, a 950 sq. ft. pool house with a bar and vaulted ceiling, personal putting green, in-ground trampoline, theatre, gym, wine cellar, and even a safe room.
LISTED BY: Royal LePage Real Estate Services Ltd., Brokerage
2. 1441 Lakeshore Road East — $9,500,000
Behind wrought-iron gates in Morrison, the Stonehaven Estate offers over 10,700 sq. ft. of refined living space on 2.24 acres. From its spiral staircase and chef’s kitchen to its saltwater pool, sauna, illuminated tennis/pickleball court, and collector’s garage, this home embodies resort-style luxury.
LISTED BY: Re/Max Hallmark Alliance Realty, Brokerage
3. 45 First Street — $7,400,000
Steps to the lake and downtown Oakville, this Muskoka Living Interiors creation strikes the perfect balance between coastal chic and modern luxury. With nearly 4,900 sq. ft. above grade, a La Cornue kitchen, 775 sq. ft. of outdoor living space, and a show-stopping principal suite, it’s designed for both entertaining and everyday elegance.
LISTED BY: Century 21 Miller Real Estate Ltd., Brokerage
4. 149 Dianne Avenue — $6,565,000
Classic Southeast Oakville elegance meets contemporary comfort. The backyard is a true entertainer’s playground with a pool, hot tub, Muskoka room with fireplace, and built-in BBQ. Inside, a grand office, chef’s kitchen, custom-finished basement with sauna and gym, and a nanny suite complete this family-friendly luxury residence.
LISTED BY: RE/MAX Escarpment Realty Inc., Brokerage
5. 47 Allan Street — $6,450,000
A gated showpiece in Old Oakville blending heritage character with modern design. This one-of-a-kind home includes a main-floor primary suite, five-car garage with a hidden lift, 1,500+ bottle wine cellar, and radiant heated floors. Outdoor living is just as impressive, with a cedar-roofed porch and wood-burning fireplace.
LISTED BY: Century 21 Miller Real Estate Ltd., Brokerage
What These Sales Say About Oakville’s Luxury Market
So far in 2025, Oakville’s luxury buyers have focused on turnkey lifestyle estates, properties with architectural pedigree, private resort-style amenities, and prime lake-adjacent locations. While last year’s record-breaking $18.6M sale still holds the crown, this year’s top transactions prove Oakville remains one of the most desirable luxury markets in the country.
