The Top 5 Most Expensive Oakville Sales of 2025
Oakville’s most expensive home sales in 2025 shared one major thing in common: location. All five were in Southeast Oakville, and more specifically, within a remarkably tight pocket close to the lake, downtown Oakville, and some of the town’s most established residential streets.
From Orchard Beach to Old Oakville and Morrison, these sales show where the highest-end buyers continue to place the greatest value. Mature lots, lake proximity, privacy, walkability, and fully finished luxury remain the defining features at the top of the market.
What They Have In Common
The top five sales ranged from $6.5 million to $10.1 million. Each property offered a different version of Southeast Oakville luxury, but the common themes were clear: large lots, exceptional outdoor spaces, custom interiors, and locations either steps from the lake or within one of Oakville’s most prestigious estate pockets.
Interestingly, they were not spread across Oakville. They were all clustered south of, or very close to, Lakeshore Road East, reinforcing how much value buyers place on the older, more established part of town.
1. 27 Park Avenue - Sold For $10,100,000
The highest sale of the year was 27 Park Avenue in Orchard Beach. The home sold for $10,100,000 after being listed at $10,999,998.
This was a standout because it combined a coveted Old Oakville location with newer estate construction and resort-level amenities. Designed by Gus Ricci with finishes by Studio H, the home offered over 10,000 square feet of living space, an infinity pool, pool house, putting green, theatre room, gym, wine cellar, and a beautifully landscaped lot.
What makes it special is the setting. Orchard Beach is one of Oakville’s most desirable micro-neighbourhoods, with a quiet lakeside feel just moments from downtown Oakville.
2. 1441 Lakeshore Road East - Sold For $9,500,000
1441 Lakeshore Road East, also known as Stonehaven Estate, sold for $9,500,000. Set on a 2.24-acre double lot in Morrison, this was the largest estate-style property in the top five.
The home offered more than 10,700 square feet of finished living space, five bedrooms, nine bathrooms, a saltwater pool, cabana, sauna, tennis and pickleball court, and extensive garage space.
The most important feature was the land. Large estate lots in Southeast Oakville are increasingly rare, and this property also offered future flexibility with two separate deeded lots.
3. 45 First Street - Sold For $7,400,000
45 First Street sold for $7,400,000 after being listed at $7,249,000. It was the only home in the top five to sell over asking and it sold in just one day.
Located just steps from the lake and downtown Oakville, this home showed the strength of turnkey luxury in the right location. Designed by Muskoka Living Interiors, it offered nearly 4,900 square feet above grade, five plus one bedrooms, six bathrooms, a pool, walk-up lower level, and excellent indoor-outdoor living.
This sale is a reminder that when a newer, highly finished home comes available on one of Old Oakville’s best streets, buyers are ready to move quickly.
4. 149 Dianne Avenue - Sold For $6,565,000
149 Dianne Avenue sold for $6,565,000 in Morrison. Set on a large private lot, the home offered over 5,000 square feet, four plus one bedrooms, six bathrooms, and a beautifully finished lower level.
Its biggest strength was lifestyle. The property included a pool, hot tub, stone patio, built-in barbecue, covered Muskoka room, gym, wet bar, cedar sauna, and a private treed setting close to Lawson Park and top local schools.
Compared to the others, this felt like the most complete family home: private, practical, beautifully finished, and designed for everyday living.
5. 6 Chartwell Road - Sold For $6,500,000
6 Chartwell Road sold for $6,500,000, rounding out the top five. This was the only direct lakefront property on the list.
Set at the foot of Chartwell Road in Old Oakville, the home offered lake views, waterfront access, a renovated interior, and a rare position directly on Lake Ontario. It had been reimagined in 2019 with design direction by Rodney Deeprose and construction by Horne Construction.
What makes this sale interesting is that even with a prime waterfront location, it took longer to sell and traded below its original list price. That says something important about the 2025 luxury market: buyers still valued irreplaceable locations, but they remained selective on price.
What These Sales Tell Us
The top of Oakville’s 2025 market was defined by Southeast Oakville. More specifically, it was defined by homes close to the lake, close to downtown, and set within older, established neighbourhoods where land and location are difficult to replicate.
The strongest results came from homes with a clear point of difference. 27 Park Avenue offered newer estate luxury in Orchard Beach. 1441 Lakeshore Road East offered rare land and scale. 45 First Street proved the power of turnkey design. 149 Dianne Avenue delivered a complete family lifestyle. 6 Chartwell Road showed the enduring value of waterfront, even in a more selective market.
For sellers, the message is clear: buyers will still pay exceptional prices for the right property, but the home needs to stand out. For buyers, these sales show just how tightly held Oakville’s best streets remain, especially in Southeast Oakville.
