Character
Rupert's Landing was built in the late 1980s and is one of the original waterfront condo communities on the west side of town. It's gated, so it feels private and calm, and the townhomes are set among mature trees with the bay always close by.
Homes you'll find
Most homes are townhomes (156 of them), plus 51 condos in the Bayview Tower building. Because these homes date from 1986–89, many have been updated over the years, and some haven't. I always compare finishes, window and roof age, and the condo corporation's reserve fund study.
Amenities & walkability
Residents share an indoor pool, squash court and fitness room, plus tennis and pickleball, a marina and kayak racks. West-end shopping on Highway 26 is a few minutes' drive, and Blue Mountain is just down the road.
Trails nearby
The Georgian Trail and the Town's West Circle route are close by, so you can bike east to downtown or west to Thornbury without loading the car.
Who it suits
Retirees and semi-retirees, skiers who want a four-season base, and anyone who values the extra security of a gated community.
Schools & shops
Collingwood's public elementary schools are Admiral Collingwood, Cameron Street, Connaught and Mountain View; high school students attend Collingwood Collegiate Institute (public) or Our Lady of the Bay (Catholic). School boundaries shift as town grows, so I always have buyers confirm the school for a specific address with the board's school locator before they fall in love with a house.
Peter's take
Rupert's Landing is a good fit if you want waterfront amenities but a smaller, quieter community than Lighthouse Point.
Last updated November 1, 2026. Neighbourhood boundaries are informal, and details come from the public sources below. Please confirm anything important (school catchment, condo rules, fees) for a specific property.