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Luxury homes for sale in Whitby

This page gathers Whitby listings asking $1.5 million and up. In this town that threshold buys a few distinct kinds of property: estate homes on large lots in and around Brooklin, acreages and hobby farms in Rural Whitby toward Ashburn and Myrtle, the newest and largest builds in Taunton North and West Whitby, houses on the lakeside streets of Port Whitby, and restored heritage homes in Downtown Whitby near Trafalgar Castle. Buyers at this level tend to arrive from Toronto, Markham or Pickering looking for land, privacy and a shorter drive on the 407 rather than a train schedule. Each of those property types is judged differently, so the map and community filter matter more here than anywhere else on the site. The Miller team has sold at this level across the town and will tell you plainly what a premium buys on a given street.

Luxury homes: Whitby (38)

See all 38 listings

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What to weigh at this price

Above $2 million, Ontario's land transfer tax charges 2.5 percent on the portion over that line for a home with one or two single-family residences, on top of the lower brackets, so closing costs deserve a line in the budget early. Rural properties need a water potability test, a septic inspection, a check of the conservation authority's regulated area and a look at the zoning and the Oak Ridges Moraine plan before you fall for the view. Newer estate homes in Brooklin and Taunton North should come with builder drawings, permits for any finished basement or pool and Tarion records. Heritage houses downtown may carry an Ontario Heritage Act designation or sit inside the Werden's Plan district, which limits exterior changes; have your lawyer confirm the status. Lakefront and creek-side lots involve the conservation authority for any future work. At this level an inspection by specialists (roof, HVAC, pool, well) is money well spent.

Questions people ask about Luxury homes for sale in Whitby

Where are Whitby's most expensive streets?

The largest homes cluster on the estate lots around Brooklin and Ashburn, the acreages of Rural Whitby, the lake-facing streets in Port Whitby and the biggest new builds north of Taunton Road. Downtown Whitby's restored century homes near Trafalgar Castle and Centre Street are the other high end, valued for character rather than size.

Are there waterfront homes in Whitby?

A limited number. Much of the shoreline is public parkland, the harbour, the Waterfront Trail and the Ontario Shores grounds, so true lakefront lots are scarce. Homes on the streets closest to the water in Port Whitby and near Lynde Shores offer lake views or a short walk to the beach rather than private frontage.

Do luxury listings in Whitby hold offers?

Less often than mid-priced homes, because the pool of buyers is smaller and the marketing runs longer. Many sellers at this level prefer offers as they come, with conditions for financing and inspection. The team will confirm the seller's process before you invest in due diligence.