Rolling Acres, Whitby
Rolling Acres detached homes for sale
Detached houses in Rolling Acres are late-1980s to early-2000s two-storeys with four bedrooms, brick fronts, two-car garages and lots wide enough for a pool on the older streets. The Fallingbrook and Bassett pockets are the earliest and have the largest trees and deepest yards; the streets closest to Taunton and Garrard Road North are the newest and often carry larger floor plans on tighter lots. Bungalows are few and get taken quickly by downsizers. Look for the usual 1990s items: roof and window replacement dates, furnace and air-conditioner age, poly-B plumbing in the earliest phase, and whether the basement was finished with permits. Houses backing onto a park, a pond or the school field are the ones buyers compete for; those backing onto Thickson or Taunton come with noise walls. Because plans repeat, walk three comparable houses before you decide what an updated kitchen is worth to you.
Rolling Acres detached homes by the numbers
Live from the MLS® feed · updated October 8, 2026
What homes here actually sold for
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Based on information from the Toronto Regional Real Estate Board.
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Questions people ask about Rolling Acres
Which streets in Rolling Acres have the biggest lots?
The late-1980s phase around Fallingbrook Street and Bassett Boulevard and the courts off them, where pie-shaped and corner lots are common. Lots shrink as you move north toward Taunton Road and east toward Garrard Road North, where the early-2000s houses sit on narrower frontages with larger footprints.
Do the houses here have basement apartments?
Some do. Side entrances and finished basements are common, and Ontario's additional residential unit rules allow a legal suite if parking, ceiling height, egress and fire separation comply. Many existing suites predate permits. Ask for the building permit and the electrical inspection, and price a retrofit into your offer if there is none.
What should I check when a Rolling Acres house backs onto a pond?
The stormwater ponds are engineered features with fluctuating levels, mosquitoes in summer and a maintenance easement along the edge. Confirm the lot line, whether any part is in a conservation regulated area, the grading toward the house, and whether the fence is yours or the Town's. The view and privacy are the reward.
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