Houses for sale in Pickering Woodlands

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Homes for sale in Pickering Woodlands

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1-10/19

  • 840 Sheppard Avenue in Pickering: Woodlands E13593332 - House

    840 Sheppard Avenue Woodlands Pickering L1V 1G5
    Main Photo: 840 Sheppard Avenue in Pickering: Woodlands E13593332 - House

    840 Sheppard Avenue Pickering L1V 1G5 Woodlands

    $1,389,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13593332
    Bedrooms:
    6
    Bathrooms:
    4
    Welcome to 840 Sheppard Avenue, where space, privacy, and timeless family living come together on an exceptional oversized lot in one of Pickering's most desirable neighbourhoods. Nestled beside a peaceful ravine, this beautifully maintained custom built home offers a rare combination of natural surroundings, generous living spaces, and incredible versatility for families of every stage. Thoughtfully designed with an exceptional layout, the home features four spacious bedrooms on the upper level, including a serene primary retreat complete with a spa inspired ensuite and an oversized private balcony overlooking the backyard - perfect for enjoying your morning coffee or unwinding at the end of the day. The main floor offers bright, sun filled principal rooms, a beautiful family room, and flexible living spaces ideal for entertaining, a home office, playroom, or reading lounge. Large windows throughout fill the home with natural light, creating a warm and inviting atmosphere. Downstairs, the fully finished lower level (with separate entrance) offers endless possibilities with two additional bedrooms, full bathroom and expansive living space, making it ideal as a recreation room, nanny or in-law suite, multigenerational living, guest accommodations, or home gym. Outside, discover your own private backyard oasis featuring a stunning swim spa, generous outdoor entertaining space, and one of the area's most coveted oversized lots. With the ravine providing additional privacy and a picturesque natural backdrop, this property truly feels like an everyday escape.Lovingly cared for and meticulously maintained, this home also offers exceptional storage throughout-a feature families will truly appreciate. Combining thoughtful design, incredible flexibility, and an unbeatable setting, 840 Sheppard Avenue is a rare opportunity to own a home that offers comfort, function, and room to grow for years to come. More details
    Listed by ROYAL LEPAGE SIGNATURE REALTY
    LISTING DETAILS
    John Owen, Broker

  • 568 Rainy Day Drive in Pickering: Woodlands E13584128 - House

    568 Rainy Day Drive Woodlands Pickering L1V 5Z2
    Main Photo: 568 Rainy Day Drive in Pickering: Woodlands E13584128 - House

    568 Rainy Day Drive Pickering L1V 5Z2 Woodlands

    $1,200,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13584128
    Bedrooms:
    5
    Bathrooms:
    3
    Welcome to this beautifully maintained 4-bedroom, 3-bathroom all-brick home, nestled on a quiet, friendly street where neighbours are kind, helpful, and truly look out for one another. This is the kind of community where everyone knows each other in the very best way. Situated on a generous pie-shaped lot, this home offers an open-concept main floor that is perfect for entertaining and everyday family living. The flexible layout allows you to tailor the space to your lifestyle, whether you need a formal dining area or a spacious gathering room for family and friends. The backyard is truly a private retreat, like having your own cottage at home. Professionally landscaped with easy-to-maintain gardens, it features a heated pool, hot tub, and dedicated BBQ area, creating the ultimate space for entertaining. Spend 3 seasons of the year enjoying this outdoor oasis, where you can treat your friends and family to a little getaway. Upstairs, the spacious primary bedroom includes a fully renovated ensuite with a soaker tub and walk-in shower. The main-floor laundry room is also fully renovated, making laundry easy. It's a room you'll actually want to be in. The finished basement is ideal for movie nights, game nights, and holiday celebrations. Storage is abundant throughout the home, so much so that the current owners park both cars in the garage, a rare convenience. The location is exceptional, offering the perfect balance of peaceful living and everyday convenience. Enjoy walking distance to restaurants, Shoppers Drug Mart, Second Cup, and groceries. Commuters will appreciate being just minutes from Highway 401 and 10 minutes from Highway 407. Exiting at Whites Road means avoiding the bottleneck after Brock Road, and commuting to Bayview can take as little as 30 minutes-comparable to many downtown Toronto commutes. This is more than just a house; it's a home designed for connection, comfort, and creating unforgettable memories. See feature sheet for additional upgrades. More details
    Listed by REALTY ONE GROUP REVEAL
    LISTING DETAILS
    John Owen, Broker

  • 432 Sheppard Avenue in Pickering: Woodlands E13580966 - House

    432 Sheppard Avenue Woodlands Pickering L1V 1E5
    Main Photo: 432 Sheppard Avenue in Pickering: Woodlands E13580966 - House

    432 Sheppard Avenue Pickering L1V 1E5 Woodlands

    $2,689,900
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13580966
    Bedrooms:
    6
    Bathrooms:
    7
    A landmark custom residence by Zippy Custom Homes, where timeless elegance, exceptional craftsmanship and contemporary design come together in one of Pickering's most coveted neighbourhoods. This distinguished home offers 6 bedrooms, 7 bathrooms, 2 kitchens, a 3-car garage and parking for up to 10 vehicles. A grand foyer introduces beautifully proportioned living and dining spaces with soaring 10-ft ceilings, abundant natural light and refined architectural detailing throughout. Behind elegant double doors, the dramatic 14-ft executive office creates an impressive work-from-home retreat. The family room captures beautiful backyard views and flows effortlessly into a chef-inspired designer kitchen created for everyday living and memorable entertaining. The luxurious primary suite is a private sanctuary with a spa-inspired 6-piece ensuite and oversized walk-in closet, while each additional bedroom enjoys its own ensuite and generous walk-in closet. Thoughtful features include a dedicated home theatre, second-floor laundry, built-in speakers, remote-controlled blinds, glass railings, more than 200 pot lights and a professionally installed 6-camera security system. Outdoors, an expansive backyard and premium composite deck extend the living space, offering an exceptional setting for gatherings or quiet relaxation. The professionally finished lower level includes a private 2-bedroom apartment with its own kitchen and separate entrance, providing outstanding flexibility for extended family, guests or income potential. Every element has been carefully considered to balance beauty with function, from the elegant finishes and impressive ceiling heights to the seamless layout designed for modern family life. Meticulously built with uncompromising attention to detail, this rare statement residence delivers remarkable scale, privacy, comfort and enduring luxury. More details
    Listed by CENTURY 21 LEADING EDGE REALTY INC.
    LISTING DETAILS
    John Owen, Broker

  • 1488 Rosebank Road in Pickering: Woodlands E13544892 - House

    1488 Rosebank Road Woodlands Pickering L1V 1P4
    Main Photo: 1488 Rosebank Road in Pickering: Woodlands E13544892 - House

    1488 Rosebank Road Pickering L1V 1P4 Woodlands

    $2,288,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13544892
    Bedrooms:
    4
    Bathrooms:
    4
    Welcome to a "Home & Garden" on a T-Shape of 1/2 ACRE Lot (21033.50 sq. ft). This is an elegant gem hidden by the lush front garden and set against a manicured back garden with an abundance of shrubs, plants, flowers, and trees, creating a cottage-like atmosphere, where privacy, peace and tranquility prevail. The house was renovated and extended with excellence in aesthetics, function, and structure. The materials are of good quality, including top-of-the-line windows and doors. The layout is spacious and imaginative, with high ceilings, including the basement, with a series of skylights. The enormous living and TV area is lit by large windows, as are other parts of the house, where careful thoughts were given to light and shade. The dining area is the strategic center of interest, as from here one can enjoy the colourful garden during summer and a Christmas wonderland during winter. The modern kitchen with a large natural quartz countertop is served by high-quality appliances. On the upper floor, the bedrooms are of good size and well finished. The basement floor is insulated. The garage is fully insulated, providing enhanced temperature control and protection for vehicles. A new furnace was installed in 2025, and the attic has R60 insulation. This magnificent home has been meticulously maintained and upgraded by the owners over the years. Conveniently located near grocery stores, restaurants, banks, primary and high schools and private Montessori school, and also within 10 minutes drive to Rosebank Station, Rouge Beach, Conservation Park and Bay /west Park. With a land area of 21033.50 sq. ft. and the existing house has 2,800 sq. ft. (excluding the finished basement), there is room for further extension, provided it is in compliance with the Planning & Building Bylaw. In addition, a separate bungalow with about 1,600 sq. ft. that has a connection to the main house is permissible. ** Drone views are marked up for ref. and a couple of pics are virtually staged. More details
    Listed by HARVEST REALTY LTD.
    LISTING DETAILS
    John Owen, Broker

  • 832 Sheppard Avenue in Pickering: Woodlands E13530404 - House

    832 Sheppard Avenue Woodlands Pickering L1V 1G5
    Main Photo: 832 Sheppard Avenue in Pickering: Woodlands E13530404 - House

    832 Sheppard Avenue Pickering L1V 1G5 Woodlands

    $1,999,999
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13530404
    Bedrooms:
    6
    Bathrooms:
    7
    Welcome to this exceptional custom built residence offering luxurious above grade living space, plus a fully finished walkout basement. Thoughtfully designed for both family living and entertaining, this stunning home features 4 spacious bedrooms, 5 bathrooms, upper level laundry, elegant formal living and dining rooms, a main floor office and a sun-dashed filled family room with a fireplace. The chefs kitchen is appointed with a quartz countertop, premium appliances and a bright breakfast area, while hardwood flooring, pot-lights and a striking wrought iron staircase elevate the homes timeless design. The fully finished walk out basement offers incredible in-law or multi-generational living potential, with a separate entrance, full kitchen, spacious living area with a fireplace, full bathroom, additional powder room, laundry room and direct access to the private backyard. Enjoy outdoor living on the large deck over looking the yard. Completing this exceptional property is a large interlocked drive-way and a double car garage. Ideally located close to excellent schools, parks, shopping. restaurants, go station, public transit and highway 401. A rare opportunity to own a beautifully crafted custom home in a prime Pickering location. More details
    Listed by PINNACLE ONE REAL ESTATE INC.
    LISTING DETAILS
    John Owen, Broker

  • 218 755 Omega Drive in Pickering: Woodlands E13527386 - Condo Townhouse

    218 755 Omega Drive Woodlands Pickering L1V 0H1
    Main Photo: 218 755 Omega Drive in Pickering: Woodlands E13527386 - Condo Townhouse

    218 755 Omega Drive Pickering L1V 0H1 Woodlands

    $569,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    E13527386
    Bedrooms:
    2
    Bathrooms:
    2
    Gorgeous Park-Facing 2-Bedroom, 2-Bath Stacked Townhome In Pickering's Highly Desirable Woodlands Community Discover The Perfect Blend Of Modern Comfort, Natural Surroundings, And Everyday Convenience .This Exceptional Unit Offers Unobstructed Views Of The Park, Creating A Peaceful And Scenic Backdrop That Enhances Your Daily Living Experience. Step Inside To A Bright And Inviting Open-Concept Living And Dining Area, Designed To Accommodate Both Relaxation And Entertaining. Large Windows Fill The Space With Natural Light, While The Seamless Flow Leads To A Spacious Private Balcony Ideal For Enjoying Morning Coffee, Hosting Friends, Or Grilling On Warm Summer Evenings. The Outdoor Space Truly Extends Your Living Area And Provides A Tranquil Retreat Overlooking Lush Greenery. The Modern Kitchen Features Granite Countertops, Stainless Steel Appliances, And Ample Cabinetry, Making Meal Preparation Both Stylish And Convenient. 9-Ft Ceilings Add A Sense Of Openness, While Vinyl Flooring Throughout Offers Durability And Contemporary Appeal. The Convenience Of Ensuite Laundry Ensures Everyday Practicality. This Unit Also Includes One Underground Parking Spot, Providing Secure And Hassle-Free Parking Year-Round. The Location Is One Of The Home's Greatest Strengths. Situated Just Steps From Schools, Parks, Shopping, Restaurants, And Essential Amenities, You'll Enjoy A Lifestyle Where Everything You Need Is Within Easy Reach. Commuters Will Appreciate The Quick Access To The Pickering Go Station And Highway?401, Making Travel To Toronto And Surrounding Areas Effortless. Nature Lovers Will Enjoy Being Surrounded By Ravine Trails, Green Spaces, And Family-Friendly Parks, Creating A Perfect Environment For Walking, Biking, And Outdoor Activities. The Woodlands Community Is Known For Its Welcoming Atmosphere, Walkability, And Strong Sense Of Neighbourhood. More details
    Listed by RE/MAX PRESIDENT REALTY
    LISTING DETAILS
    John Owen, Broker

  • 560 Steeple Hill in Pickering: Woodlands E13508370 - House

    560 Steeple Hill Woodlands Pickering L1V 5Z3
    Main Photo: 560 Steeple Hill in Pickering: Woodlands E13508370 - House

    560 Steeple Hill Pickering L1V 5Z3 Woodlands

    $1,039,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13508370
    Bedrooms:
    6
    Bathrooms:
    4
    Power Of Sale - Spacious All Brick 4+2 Bedroom, 1+1 Kitchen Home, Located In The Desirable Woodlands Neighbourhood. Featuring Main Floor Living And Dining Rooms, Large Family Room W/ Gas Fireplace, Family Size Eat-In Kitchen With Walk-Out To Deck, Main Floor Laundry, Separate Side Entrance, And Entrance To Basement From Garage. 2nd Floor Grand Size Primary Bedroom Invites You To A Beautiful Light & Bright Sitting Area With Walk-In Closet And 4 Piece Ensuite Bath, 3 Good Size Bedrooms, And Full 4-Piece Family Bathroom. The Basement Is Finished With Direct Entrance From Garage, A Large Living Area, 2 Bedrooms, Kitchen, And Full Bathroom With Laundry Area. Prime Location Close To All Amenities And Easy Access To Hyw 401. Property Being Sold "As Is, Where Is" And Does Require Some Work. More details
    Listed by Career Real Estate Services Ltd.
    LISTING DETAILS
    John Owen, Broker
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  • 1449 Rosebank Road in Pickering: Woodlands E13509302 - House

    1449 Rosebank Road Woodlands Pickering L1V 1P3
    Main Photo: 1449 Rosebank Road in Pickering: Woodlands E13509302 - House

    1449 Rosebank Road Pickering L1V 1P3 Woodlands

    $1,850,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13509302
    Bedrooms:
    5
    Bathrooms:
    4
    Rare 120' x 200' lot! Upscale Pickering Woodlands neighbourhood. Minutes to 401/Toronto border, GO Train, 407, schools, and shopping. Fantastic, larger, custom-built stone and brick bungalow approximately 2976 sf. Ample parking for approximately ten cars in the courtyard driveway. Oversized triple garage (double front door width & one tandem). This custom bungalow offers a unique open-concept main floor, perfect for entertaining family and friends. The open-concept kitchen features granite countertops, a large center island, a wall-to-wall pantry, stainless steel appliances, numerous skylights, cathedral ceilings, and a spacious eating area with a walkout to an oversized, maintenance-free deck. A gas fireplace separates the kitchen and great room. Step down to the spacious ground-floor family room, featuring a stone gas fireplace, hardwood floors, and California shutters for added privacy. The Primary Bedroom is a unique space featuring a 5-piece custom en-suite bath with a private staircase to the lower-level walk-in dressing room, complete with built-in custom cabinets. Off the Primary bedroom is a second bedroom, which can also serve as a main-floor den or be customized into a walk-in dressing room. Two additional spacious bedrooms on the main floor, one of which features a 5-piece custom semi-ensuite. Also, for convenience, there is a main-floor 2-pc designer powder room. The main staircase leads down to the spacious recreation room, an additional bedroom, both with above-grade windows, and a three-piece custom bath. There is also ample unfinished storage space in the basement area. The sprinklers are located in the front and back yards on timers. The oversized backyard offers multiple options for family enjoyment, including a hot tub on a private patio off the deck. More details
    Listed by ROYAL LEPAGE TERREQUITY REALTY
    LISTING DETAILS
    John Owen, Broker

  • 561 Cattail Court in Pickering: Woodlands E13494064 - House

    561 Cattail Court Woodlands Pickering L1V 6A2
    Main Photo: 561 Cattail Court in Pickering: Woodlands E13494064 - House

    561 Cattail Court Pickering L1V 6A2 Woodlands

    $1,187,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13494064
    Bedrooms:
    4
    Bathrooms:
    3
    WELCOME TO 561 CATTAIL COURT, PICKERING Stunning All-Brick Detached Home on a Quiet Court in the Highly Sought-After Woodlands Community, A beautifully maintained and updated all-brick detached home, ideally situated on a quiet court in the highly desirable Woodlands neighbourhood. The newly renovated modern kitchen features stylish finishes, granite countertops, and updated stainless steel appliances, making it perfect for both everyday living and entertaining.The main floor offers the convenience of a laundry room, while the cozy Separate Family Room, Dining Room and Living Room provides a warm and inviting space to relax. Additional upgrades include updated windows and a durable metal roof for long-term peace of mind.The spacious primary bedroom boasts a walk-in closet and a luxurious 5-piece ensuite. A double-car garage with direct access to the home, along with a large double Newly Paved Driveway accommodating up to four vehicles, provides ample parking for family and guests.This exceptional home combines comfort, functionality, and a prime location in one of the area's most sought-after communities.Minutes to parks, shopping, schools, Rouge Hill & Pickering GO Stations, Highways 401 & 407, and just 20 minutes to downtown. Quick drive to the lake and close to the scenic hiking and biking trails of Rouge National Urban Park. More details
    Listed by RE/MAX ROUGE RIVER REALTY LTD.
    LISTING DETAILS
    John Owen, Broker

  • 522 Sheppard Avenue in Pickering: Woodlands E13477614 - House

    522 Sheppard Avenue Woodlands Pickering L1V 1E8
    Main Photo: 522 Sheppard Avenue in Pickering: Woodlands E13477614 - House

    522 Sheppard Avenue Pickering L1V 1E8 Woodlands

    $1,098,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13477614
    Bedrooms:
    3
    Bathrooms:
    2
    A rare opportunity in Pickering's highly sought-after Woodlands community to own an expansive 75' x 180' ft lot surrounded by custom-built homes. Whether you choose to move in, renovate, or design and build your dream luxury residence, this property offers exceptional potential in one of Pickering's most desirable communities. The updated interior offers a bright open-concept living and dining area with a walk-out to the backyard deck, creating a natural indoor-outdoor connection, along with a renovated kitchen featuring stainless steel appliances and a functional layout for everyday living and entertaining. The home also includes a private second-level primary retreat with a cozy sitting area, a flexible main-floor second bedroom, and a finished basement with separate entrance complete with a kitchenette, third bedroom, 4-piece bathroom, and additional living space suitable for extended family or in-law potential. A standout feature is the impressive 900sqft garage, with 11' ceilings, a dedicated 200-amp electrical panel, and EV charger, ideal for hobbyists or additional workspace. Enjoy a private backyard setting with mature trees and multiple outdoor entertaining areas, all while being conveniently located close to Highway 401, transit, top schools, parks, The Rouge conservation areas, shopping, restaurants, and everyday amenities. More details
    Listed by RE/MAX ALL-STARS BENCZIK KAVANAGH TEAM
    LISTING DETAILS
    John Owen, Broker
1-10/19
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Data was last updated July 23, 2026 at 04:15 PM (UTC)
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.
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This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.