Houses for sale in Pickering Woodlands

Newest MLS listings in Pickering Woodlands area

Homes for sale in Pickering Woodlands

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1-10/18

  • 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

  • 499 Lightfoot Place in Pickering: Woodlands E13471486 - House

    499 Lightfoot Place Woodlands Pickering L1V 5Z6
    Main Photo: 499 Lightfoot Place in Pickering: Woodlands E13471486 - House

    499 Lightfoot Place Pickering L1V 5Z6 Woodlands

    $1,025,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13471486
    Bedrooms:
    5
    Bathrooms:
    4
    Looking for a place to make your own?Rare opportunity to secure a spacious family home on a premium cul-de-sac lot backing directly onto Ernie Stroud Park in one of Pickering's most established and sought-after neighbourhoods. Offering an exceptional combination of location, lot size, and living space, this property presents tremendous potential for buyers looking to renovate, personalize, and create long-term value.Designed with family living in mind, the home features a functional and spacious layout that includes a dramatic curved staircase, main floor laundry, a double car garage, and two kitchens, providing flexibility for multigenerational living, extended family, or future income potential. The walkout basement opens directly to the backyard, creating seamless view to the park setting beyond and offering endless possibilities.The true standout feature is the remarkable setting. Backing onto Steeple Hill Park and just a short walk to the trails, forests, and natural beauty of Rouge National Urban Park, this property offers a rare connection to nature while remaining close to everyday conveniences. Families will appreciate the proximity to parks, schools, shopping, restaurants, public transit, GO Transit, Highway 401, and major commuter routes.Whether you are an end-user seeking the opportunity to create your dream home, an investor looking to add value, or a buyer searching for a property with space and flexibility in an outstanding location, this is a rare chance to secure a home with exceptional potential in a truly desirable setting. More details
    Listed by RE/MAX ULTIMATE REALTY INC.
    LISTING DETAILS
    John Owen, Broker

  • 1482 Old Forest Road in Pickering: Woodlands E13459550 - House

    1482 Old Forest Road Woodlands Pickering L1V 1N9
    Main Photo: 1482 Old Forest Road in Pickering: Woodlands E13459550 - House

    1482 Old Forest Road Pickering L1V 1N9 Woodlands

    $1,699,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13459550
    Bedrooms:
    6
    Bathrooms:
    5
    Fully renovated, Newly Completed Home on a Premium approx. 55 x 150 Ft Lot, 4180 sqf of Livable Area ( for the three levels) in One of Pickering's Most Desirable Rouge River Communities, 10 minutes to GO Train, 3 minutes to Hwy 401, Located on a quiet upscale street backing onto a private forested setting. Offering full of sun and above grade legal tenanted apartment providing immediate steady income helping offset carrying cost and enhancing overall affordability (can be combined with the main home).Main floor features a spacious family room with gas fireplace, formal living/dining room, a chef's kitchen with premium appliances, designer cabinetry, quartz backsplash, oversized waterfall island with prep sink, plus a spectacular solarium, outstanding entertainer's all-seasons gem of a breakfast area, U.F. heating porcelain floors, walk-out to a scenic deck overlooking the highly sought-after Rouge Forest. Additional features include glass railings, accent walls, rough-in gas for BBQ and Garage heaterUpper level offers 4 spacious bedrooms, including a luxurious primary retreat with fireplace, walk-in closet and spa-inspired ensuite plus a second master bedroom, coffee station, upper-level laundry, and linen closet.Fully finished above-grade legal 2-bedroom apartment with separate entrance, private deck overlooking great views, in-suite laundry, generating $2,300/month + 40% utilities, excellent A+ one tenant and willing to stay.Minutes to top-rated schools, parks, shopping, transit, Library. *** WIFI (G.F.) windows shutters, fridge, doorbell and heat control. More details
    Listed by RIGHT AT HOME REALTY
    LISTING DETAILS
    John Owen, Broker

  • 1436 Highbush Trail in Pickering: Woodlands E13214954 - House

    1436 Highbush Trail Woodlands Pickering L1V 1N5
    Main Photo: 1436 Highbush Trail in Pickering: Woodlands E13214954 - House

    1436 Highbush Trail Pickering L1V 1N5 Woodlands

    $2,250,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13214954
    Bedrooms:
    4
    Bathrooms:
    4
    Welcome to this custom built, Victorian farmhouse-style home on a double premium lot backing onto tranquil Petticoat Creek in one of Pickering's most desirable neighbourhoods. This 4 bedroom, 2 storey home features an inviting wrap-around porch that offers the perfect place to relax and unwind. Walking through the front door, the magnificent wooden staircase rises before you & is banked by the formal living and dining rooms. It is the ideal space for entertaining, featuring hardwood floors, detailed millwork & high ceilings. The hallway leads to an open-concept kitchen & family room to expand your entertaining area & forms the heart of the home. The large windows showcase the lush ravine & fill the space with natural light. The double-sided fireplace adds warmth & charm throughout the area & into the adjoining den. Accessible from the family room is the main floor laundry room, which provides access to outside. Upstairs, 4 spacious bedrooms provide comfort & privacy. The primary suite offers a serene retreat with a large walk-in closet, ensuite bath & a ravine view. A unique feature of the 2nd floor is a linen closet with a laundry chute to the laundry room. Downstairs is a large entertainment room featuring a walk out to the ravine & accommodates a pool table, games table, a comfortable area to watch TV & an area ready for a bar of your design. This level also has a laundry room, 3 pc washroom, a room for crafting & relaxing, a storage room & a workroom, with sink & additional storage. Outdoors, the property continues to impress with an oversized detached 2 car garage, mature trees & a large private yard for relaxation & entertaining while listening to the gentle sounds of Petticoat Creek. Located close to parks, trails, library, schools, transit, shopping, & only minutes from Toronto, this home offers a rare blend of natural beauty, privacy, & convenience. A perfect balance of Victorian farmhouse elegance & modern living - truly a place to call home. More details
    Listed by REMAX CONNECT REALTY
    LISTING DETAILS
    John Owen, Broker

  • 522 Sheppard Avenue in Pickering: Woodlands E13175322 - House

    522 Sheppard Avenue Woodlands Pickering L1V 1E8
    Main Photo: 522 Sheppard Avenue in Pickering: Woodlands E13175322 - House

    522 Sheppard Avenue Pickering L1V 1E8 Woodlands

    $1,298,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13175322
    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
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  • 212 1655 Pickering Parkway in Pickering: Woodlands E13175932 - Condo Apartment

    212 1655 Pickering Parkway Woodlands Pickering L1V 6L3
    Main Photo: 212 1655 Pickering Parkway in Pickering: Woodlands E13175932 - Condo Apartment

    212 1655 Pickering Parkway Pickering L1V 6L3 Woodlands

    $515,900
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    E13175932
    Bedrooms:
    2
    Bathrooms:
    2
    Welcome to 1655 Pickering Parkway! Fabulous 2 Bedroom, 2 Bathroom, spacious condo available for sale in a prime pickering location. Laminate floors throughout, beautiful sun-filled solarium with tons of natural light, upgraded light fixtures, newer kitchen with built in dishwasher, ensuite laundry, primary bedroom with walk-in closet and so much more. Unit Shows 10+++. Steps to all shopping amenities, parks, 401 and place of worship. Book your appointment today, you won't be disappointed. More details
    Listed by REVEL REALTY INC.
    LISTING DETAILS
    John Owen, Broker

  • 1459 Old Forest Road in Pickering: Woodlands E13169064 - House

    1459 Old Forest Road Woodlands Pickering L1V 1N8
    Main Photo: 1459 Old Forest Road in Pickering: Woodlands E13169064 - House

    1459 Old Forest Road Pickering L1V 1N8 Woodlands

    $2,699,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13169064
    Bedrooms:
    8
    Bathrooms:
    6
    This stunning 5-bedroom, 6-bathroom modern and sleek home is nestled in one of Pickering's prestigious neighborhoods offering luxurious living at its finest, and it is roughed in for an elevator and will be installed if requested. This contemporary and elegant home offers 5100 sq ft of open concept living on the main and second floor. The main floor has 11.5ft ceilings and 10ft ceilings on the second floor. Every room in this home has lots of natural light that comes through the upgraded aluminum windows and feather touch Aluprof aluminum sliding doors. The sleek and clean lines along with high end finishes make this home perfect for both intimate gatherings and large-scale entertaining. Each room has been thoughtfully crafted with top-of-line materials, from the gourmet kitchen to the spa-like bathrooms that give you a sense of tranquility and luxury. The grand primary suite is a highlight, featuring a private balcony, a spacious walk-in closet, and a spa like ensuite bathroom with a soaker tub, separate dual vanities and a large 8'x4' seamless glass shower with 2 rain shower heads. Each additional bedroom is generously sized, with ample closet space and access to beautifully appointed bathrooms. The home also boasts a fully finished lower level with its own separate entrance, 3 generous sized bedrooms, a 4 piece bathroom, 9' ceilings and a full kitchen that is open to the living area. Outside, the meticulously landscaped yard offers a private oasis. Off of the kitchen you have a 29'x16' deck perfect for relaxation or entertaining, there is also a natural gas hook-up for your BBQ. The home's location is located in an upscale neighborhood and is close to schools, dining and shopping, making it an unparalleled opportunity for those looking for a blend of modern luxury and exclusive living. This home is in one of Pickering's sought after areas. There are too many features to list, please see attached "Feature Sheet" for more details More details
    Listed by SUTTON GROUP-HERITAGE REALTY INC.
    LISTING DETAILS
    John Owen, Broker

  • 1427 Rosebank Road in Pickering: Woodlands E13170706 - House

    1427 Rosebank Road Woodlands Pickering L1V 1P3
    Main Photo: 1427 Rosebank Road in Pickering: Woodlands E13170706 - House

    1427 Rosebank Road Pickering L1V 1P3 Woodlands

    $2,649,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13170706
    Bedrooms:
    7
    Bathrooms:
    7
    Absolutely Stunning 4 years Brand new Custom built Luxury Detached home, Approx 4200 Sq Ft Grand Living, High Quality home with *ELEVATOR* all 3 Floors, 5 & 4 PC Ensuite all bedrooms, Main floor Office, Extra large Interlocking Drive way, Cathedral Ceiling, Gorgeous gourmet chef's Kitchen W/Center Island, ***Spiral Staircase*** Walk-Up basement, Separate entrance, with 3 bedrooms, Rec/Games Room, High Ceiling in Basement w/2 Separate 4 Pc Ensutis, *****Your Clients will fall in-Love with this beautiful Custom design home.***** More details
    Listed by RE/MAX CROSSROADS REALTY INC.
    LISTING DETAILS
    John Owen, Broker

  • 1411 Old Forest Road in Pickering: Woodlands E13169162 - House

    1411 Old Forest Road Woodlands Pickering L1V 1N8
    Main Photo: 1411 Old Forest Road in Pickering: Woodlands E13169162 - House

    1411 Old Forest Road Pickering L1V 1N8 Woodlands

    $3,450,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13169162
    Bedrooms:
    7
    Bathrooms:
    6
    Welcome to The Bridge House - Where Family Stays Connected. A thoughtfully designed generational estate on a 50x238 ft lot in one of Pickering's most private, low-density pockets - just 1.3km to Hwy 401, 300m to Kingston Rd transit & minutes to shopping, restaurants & everyday amenities | 4,932 sq ft above grade | 1,850 sq ft finished basement | 6+1 beds | 6 baths | 3-car garage | Elevator to all floors | 10 parking spaces | The centrepiece: a custom enclosed second-floor bridge connects the main house to a fully self-contained 1-bed suite above the garage - complete with its own kitchen, living/dining area, laundry & independent HVAC system. True privacy. Total connection | Main floor: 10 ft smooth ceilings, open-concept living/dining/family room with gas fireplace & custom TV niche | A chef's kitchen w/ SubZero, Wolf & Miele appliances, hidden walk-in pantry w/ auto sensor lighting, pot filler, quartz counters, & servery with SubZero beverage centre | Office with window, closet & frosted pocket doors - functions as main floor bedroom | Primary retreat: 16-ft walk-through closet, tray ceilings, spa-inspired 5-pc ensuite w/ freestanding tub, glass shower with niche, heated floors, & water closet | Basement 9 ft smooth ceilings with Dricore subfloor | Absolute show stopper wet bar w/ dual Marvel beverage centres & glass rinser, glass-enclosed gym w/ full mirrored wall & hardwired internet | Pre-wired for future home theatre | Kohler steam shower w/ essential oil diffuser, heated floors | double-door walkout | Garage: fully insulated, high-lift track doors (car-lift ready every bay), hot water line & Cat-5 | Massive Backyard w/ gas BBQ line, 60-amp rough-in & hot water tap. 226 pot lights | 2 furnaces + 1 air handler | 3 AC's/HRV | Rain Bird WiFi irrigation system | 3 built-in WiFi routers | Pre-wired speakers | This Home Truly Has It All - See Attached Lists & Media Links For Details. More details
    Listed by RE/MAX ROUGE RIVER REALTY LTD.
    LISTING DETAILS
    John Owen, Broker

  • 413 Sheppard Avenue in Pickering: Woodlands E13149064 - House

    413 Sheppard Avenue Woodlands Pickering L1V 1E6
    Main Photo: 413 Sheppard Avenue in Pickering: Woodlands E13149064 - House

    413 Sheppard Avenue Pickering L1V 1E6 Woodlands

    $2,499,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13149064
    Bedrooms:
    6
    Bathrooms:
    6
    Welcome To 413 Sheppard Ave Located In Prestigious Woodlands. This Exceptional 4+2 Bedroom, 6 Bathroom Family Home Offers Almost 5000 Sqft Of Above Grade Living Space plus fully finished basement With A Bright, Open Concept Layout Designed For Modern Living And Entertaining. Grand Principal Rooms, Soaring Ceilings, Expansive Windows, And Elegant Finishes Create A Warm Yet Sophisticated Atmosphere Throughout.The Main Floor Features Spacious Living And Dining Areas, A Stunning Family Room Open To The Kitchen, A Private Office, And Seamless Walkouts To The Backyard. The Chef-Inspired Kitchen Includes Premium Appliances, Oversized Island, Extensive Cabinetry, And A Functional Layout Ideal For Families And Hosting.The Luxurious Primary Retreat Features A Spa-Like Ensuite, Walk-In Closet, And Private Balcony. Generously Sized Secondary Bedrooms Filled With Natural Light. The Finished Walkout Basement Includes A Large Recreation Area, Theatre Room, Additional Bedrooms And Bathrooms, Plus a Full Kitchen Offering Excellent In-Law Or Income Potential. Located In A Highly Sought-After Family Community Close To Top Ranked Schools, Parks, Trails, Shopping, And Major Amenities. A Rare Opportunity To Own A Truly Impressive Luxury Home In One Of Pickering's Most Desirable Neighbourhoods. More details
    Listed by RE/MAX MILLENNIUM REAL ESTATE
    LISTING DETAILS
    John Owen, Broker
1-10/18
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Data was last updated June 23, 2026 at 12:15 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.