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Semi-Detached  for sale at 1286 Winding Woods Trail, Pickering - 4 bedroom, 3 bathroom - Photo 1 of 1
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$929,000

1286 Winding Woods Trl

Pickering, ON L1X 0R9

1286 Winding Woods Trl, PickeringListed at $929,000. 4 bedroom, 3 bathroom 2 1/2 Storey Semi-Detached. MLS® E13586462.

4Beds
3Baths
2000-2500sqft
Semi-Detached
2 1/2 Storey
2Parking
$1,825.39Taxes/yr · 2026

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Description

**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.

Property Details

Property TypeSemi-Detached
Style2 1/2 Storey
CommunityRural Pickering
Approximate AgeNew
Rooms9
Kitchens1
Washrooms3
Square Feet2000-2500 sqft
Lot Dimensions23.91 × 88 ft
Fronting OnEast
Dir/Cross StPeter Matthews Drive and Talisman Manor
Garage TypeAttached
Garage Parking Spaces1
DriveAvailable
Parking Drive Spaces1
Total Parking Spaces2
ExteriorBrick
RoofAsphalt Shingle
FoundationPoured Concrete
BasementUnfinished
Fireplace FeaturesElectric
Heating TypeForced Air
Heating SourceElectric
A/CCentral Air
SewersSewer
Taxes (2026)$1,825.39
HSTIncluded In
UFFINo
Listed Date7/21/2026
Days on Market15 days
PossessionTBD
Same-day showings available
5.0Rated 5 stars on Google ReviewsWhatsApp Us About This Listing

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Home Value
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Listing Courtesy of: ROYAL LEPAGE TERREQUITY REALTY

MLS® #E13586462

TRREBMLS®

The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing data is deemed reliable but is not guaranteed accurate by TRREB. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.

© 2026 Toronto Regional Real Estate Board. All rights reserved.

Thinking about living in Pickering?

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HouseIndex Take: 1286 Winding Woods Trail

This semi-detached (2 1/2 Storey) is located in the Rural Pickering neighbourhood of Pickering.

The home offers 4 bedrooms, 3 bathrooms.

Features include a unfinished basement, 2 parking spaces including a 1-car garage, a fireplace.

Additional details: lot dimensions of 23.91 × 88 feet.

Listed at $929,000 CAD with annual property taxes of $1,825.39 (2026).

About Pickering Real Estate

This Semi-Detached is located in the Rural Pickering community in Pickering. Pickering bridges Toronto's east end and Durham Region, offering relatively affordable homes with direct GO Train connectivity. The Pickering Town Centre area is undergoing major intensification, while established neighbourhoods like Rougemount and Liverpool offer mature streetscapes. Rouge National Urban Park is a unique asset for nature enthusiasts. Semi-detached homes in Pickering provide freehold ownership at a more accessible price point, appealing to first-time buyers and young families.

Rouge National Urban ParkPickering GO — 35 min to UnionPickering Town Centre intensificationWaterfront & Frenchman's Bay marina
~40 min commute to downtown TorontoWalkability: Moderate near Town Centre — suburban elsewhere
View full Pickering neighbourhood guide →