1286 Winding Woods Trail, Pickering, ON L1X 0R9
Rural Pickering, Pickering · Near Peter Matthews Drive and Talisman Manor · View map
About this home
**The Landmark** offers nearly 2,000 sq. ft. of thoughtfully designed living space, perfect for growing families. This 4-bedroom, 2.5-bath home features an open-concept main floor with a spacious family room, bright breakfast area, and modern kitchen-ideal for everyday living and entertaining. Upstairs, the private primary retreat includes a walk-in closet and luxurious ensuite, while three additional bedrooms and second-floor laundry provide exceptional convenience. Complete with a built-in garage and timeless curb appeal, The Landmark combines style, functionality, and comfort in one exceptional home.
The home
- Type
- Semi-detached home
- Style
- 2 1/2 Storey
- Square footage
- 2000-2500 sq ft
- Bedrooms
- 4
- Bathrooms
- 3
- Kitchens
- 1
- Rooms
- 9
- Basement
- Unfinished
- Lot size
- 23.9 x 88 ft
- Faces
- East
- Approximate age
- New
Ownership & fees
- Ownership
- Freehold
- Monthly condo fee
- None
- Exterior
- Brick
Heating & cooling
- Heating fuel
- Electric
- Heating type
- Forced Air
- Air conditioning
- Central Air
- Fireplace
- Yes
Garage & parking
- Garage
- Attached
- Garage spaces
- 1
- Driveway spaces
- 1
- Total parking
- 2
- Parking features
- Available
Taxes & other
- Property taxes
- $1,825/yr
- Tax year
- 2026
- Occupancy
- Vacant
- Possession
- TBD
- Cross street
- Peter Matthews Drive and Talisman Manor
- Neighbourhood
- Rural Pickering
More
- Price per sq ft
- ~$413 (at 2,250 sq ft)
- MLS® number
- E13586462
No matching details. Ask Will instead
No features listed yet.
- Mortgage
- Property tax
- Maintenance fee
Cash needed to close
Estimates only, using Canadian semi-annual compounding, Ontario land transfer tax. Mortgage default insurance is added when you put down less than 20%. Your lender and lawyer will confirm exact numbers.
1286 Winding Woods Trail, Pickering, ON L1X 0R9
Rural Pickering, Pickering · Near Peter Matthews Drive and Talisman Manor
Get directionsWhat’s nearbySchools nearby
Open this tab to load nearby schools.
Your commute
Enter where you go every day to see real drive times:
Listing history for 1286 Winding Woods Trail
See what this home and others at the same address were listed for, what they sold for, and how long it took.
Sold prices are for members. It’s free, takes a few seconds, and unlocks the sale history on every listing.
Frequently asked questions about 1286 Winding Woods Trail
Answers come straight from this home’s MLS® listing.
How much is 1286 Winding Woods Trail listed for, and what would it cost each month?
1286 Winding Woods Trail is listed for $929,000. With 20% down ($185,800), the mortgage payment would be roughly $3,747 a month at 4.5% over 30 years. Add property tax and the estimate comes to about $3,899 a month, all in. That figure is an illustration, not a quote.
Is 1286 Winding Woods Trail freehold or a condo, and is there a monthly fee?
1286 Winding Woods Trail is a semi-detached home in Rural Pickering, Pickering. Ownership is freehold: you own the home and the lot. There is no monthly condo fee, so the roof, windows, driveway, snow and lawn are yours to look after.
How many bedrooms and bathrooms does 1286 Winding Woods Trail have?
1286 Winding Woods Trail has 4 bedrooms and 3 bathrooms. The listing gives the style as 2 1/2 storey.
Does 1286 Winding Woods Trail have a garage and parking?
Yes. The listing shows the garage as attached, with room for 1 car. The driveway adds 1 space. In total the listing counts 2 parking spaces.
Does 1286 Winding Woods Trail have a finished basement?
The listing describes the basement as unfinished.
What style of home is 1286 Winding Woods Trail?
1286 Winding Woods Trail is a semi-detached home. A semi-detached home shares one side wall with the home next door.
How big is 1286 Winding Woods Trail, and what is the lot size?
The listing puts the home between 2,000 and 2,500 sq ft. The board reports a range rather than an exact figure, and it usually leaves out the basement. The lot is listed as 23.9 x 88 ft.
How is 1286 Winding Woods Trail heated and cooled?
Heating is forced air (electric). Cooling is central air.
What are the property taxes for 1286 Winding Woods Trail?
Property taxes are $1,825 a year (2026), or about $152 a month.
Where is 1286 Winding Woods Trail?
1286 Winding Woods Trail is in the Rural Pickering community of Pickering. The nearest main intersection is Peter Matthews Drive and Talisman Manor. The postal code is L1X 0R9.
Is 1286 Winding Woods Trail still for sale?
Yes. It is an active listing (MLS® E13586462). Listings here update from the board through the day and come down once a home sells.
What are similar properties near 1286 Winding Woods Trail asking?
Similar properties for sale nearby right now include 1284 Winding Woods Trail at $939,990 (4 bed), 1292 Winding Woods Trail at $969,990 (4 bed) and 2429 Angora Street at $910,000 (3 bed). These are asking prices, not sold prices. The Sold history tab shows what homes at this address went for.
What have homes at 1286 Winding Woods Trail sold for?
Recent sales, leases and expired listings for this home and others at the same address are in the Sold history tab, with the price and date of each. It is free for members.
How do I book a showing at 1286 Winding Woods Trail?
Pick a day and time with Book a Tour on this page. Tours are free, with no obligation, in person or by video. You can also call or text 647-931-3923.
Have a different question? Ask about this home and get an answer, usually within the hour.
Similar properties nearby
More properties for sale near Rural Pickering, picked by style, size and price.
Semi-detached home$939,9901284 Winding Woods Trail, Pickering4 bed · 3 bath · Rural PickeringCourtesy of: RE/MAX PREMIER INC.View home →
Semi-detached home$969,9901292 Winding Woods Trail, Pickering4 bed · 3 bath · Rural PickeringCourtesy of: RE/MAX PREMIER INC.View home →
Semi-detached home$910,0002429 Angora Street, Pickering3 bed · 3 bath · Rural PickeringCourtesy of: FOREST HILL REAL ESTATE INC.View home →Courtesy of: ROYAL LEPAGE TERREQUITY REALTY
Listing information comes from the Toronto Regional Real Estate Board through PropTx and is deemed reliable but is not guaranteed accurate. It is provided for consumers' personal, non-commercial use. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA.
*Estimated monthly cost assumes 20% down, a 4.5% rate and a 30-year amortization, plus property tax. For illustration only.