Houses for sale in Pickering Woodlands

Newest MLS listings in Pickering Woodlands area

Homes for sale in Pickering Woodlands

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  • 33 735 Sheppard Avenue in Pickering: Woodlands E12985610 - Condo Townhouse

    33 735 Sheppard Avenue Woodlands Pickering L1V 7K5
    Main Photo: 33 735 Sheppard Avenue in Pickering: Woodlands E12985610 - Condo Townhouse

    33 735 Sheppard Avenue Pickering L1V 7K5 Woodlands

    $779,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    E12985610
    Bedrooms:
    3
    Bathrooms:
    3
    Rarely Available, Stunningly RENOVATED, 3 Bedroom, 3 Bathroom Townhome in One of The Most Sought After Areas of Pickering! Private Complex Nestled in Beautiful Greenery. A Perfect Home for Any Family! Gorgeous Updated Kitchen with New Stainless-Steel Appliances, Under-mounted Sink, Backsplash, Quartz Counters, Island and Pot Lights. Very Bright Living Spaces, Large Bedrooms, Fully Renovated Main and 2nd Floor Bathrooms & DirectAccess to the Home from the Garage! Spacious Terrace/Deck off the Family Room Extends the Living Space Outdoors! Close To Every Convenience You Can Imagine. Minutes to: Transit, Groceries, Hwy 401/412/407, The Go Station, Restaurants, Banks, Pickering Town Centre, Parks, Conservation Area, Library, Schools & Places of Worship. VERY LOW maintenance fees cover Water, Building Insurance and Property Management(Landscaping/Grass/Snow). Ideal Location in a Coveted Complex! Move-In Ready & A Must See! More details
    Listed by CENTURY 21 NEW CONCEPT
    LISTING DETAILS
    John Owen, Broker

  • 1449 Rosebank Road in Pickering: Woodlands E12965508 - House

    1449 Rosebank Road Woodlands Pickering L1V 1P3
    Main Photo: 1449 Rosebank Road in Pickering: Woodlands E12965508 - House

    1449 Rosebank Road Pickering L1V 1P3 Woodlands

    $1,950,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12965508
    Bedrooms:
    5
    Bathrooms:
    4
    Prestigious Woodlands Pickering neighbourhood minutes to 401/Toronto border, GO Train, 407, schools, and shopping. Fantastic, larger, custom-built stone and brick bungalow approximately 2976 sf, nestled on a 120' x 200' mature level lot. Ample parking for approximately ten cars in the courtyard driveway. Oversized triple garage (double width & one tandem). This oversized bungalow offers a unique open-concept main floor, perfect for a large family to entertain family and friends. The open concept kitchen features granite countertops, an island, a wall-to-wall pantry, stainless steel appliances, numerous skylights, and a spacious dining area with a walkout to an oversized composite deck. A gas fireplace separates the kitchen and great room. Step down to the spacious family room, featuring a 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 and a private staircase to the lower-level walk-in custom dressing room, complete with built-in cabinets. This dressing room also provides access to an office/den area, offering a private workspace at home with a large window overlooking the yard. Off the Primary bedroom is the nursery, which can be used to keep the little ones close, serve as a main-floor den, or be customized into a walk-in dressing room. There are two additional generously sized 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 basement offers access from the front entry hall to the recreation room and an additional bedroom, both with above-grade windows, and a three-piece custom bath. There is ample unfinished storage space in the basement area. The sprinklers are located in the front and back yards and are on timers. The oversized backyard offers multiple options for family enjoyment! More details
    Listed by ROYAL LEPAGE TERREQUITY REALTY
    LISTING DETAILS
    John Owen, Broker

  • 319 755 Omega Drive in Pickering: Woodlands E12931800 - Condo Townhouse

    319 755 Omega Drive Woodlands Pickering L1V 0H1
    Main Photo: 319 755 Omega Drive in Pickering: Woodlands E12931800 - Condo Townhouse

    319 755 Omega Drive Pickering L1V 0H1 Woodlands

    $548,999
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    E12931800
    Bedrooms:
    2
    Bathrooms:
    3
    Welcome to this executive modern 2-storey townhouse in highly desired Woodlands, Pickering. Offering 1,100+ sq ft of well-designed living space, this home combines contemporary style with everyday comfort. The main level features a bright open-concept living and dining area with wide-plank flooring and a modern kitchen equipped with stainless steel appliances and ample cabinetry-perfect for entertaining or relaxed daily living. Step out to your private balcony and enjoy open views. The lower level hosts two generously sized bedrooms, each offering excellent privacy and natural light. The primary bedroom includes a 3-piece ensuite bathroom, while a second full bathroom serves the additional bedroom. A convenient powder room is located on the main level. In-unit laundry and numerous builder upgrades throughout complete this impressive home. Ideally situated close to shopping malls, schools, transit, Highway 401, bus stops, Tim Hortons, LCBO, and all major amenities-making commuting and daily errands effortless. A fantastic opportunity for a small family, first time home buyer or investor. More details
    Listed by ROYAL LEPAGE MEADOWTOWNE REALTY
    LISTING DETAILS
    John Owen, Broker

  • 415 Sheppard Avenue in Pickering: Woodlands E12919796 - House

    415 Sheppard Avenue Woodlands Pickering L1V 1E6
    Main Photo: 415 Sheppard Avenue in Pickering: Woodlands E12919796 - House

    415 Sheppard Avenue Pickering L1V 1E6 Woodlands

    $2,699,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12919796
    Bedrooms:
    7
    Bathrooms:
    6
    Welcome To 415 Sheppard Ave Located In Prestigious Woodlands. This Custom 5+2 Bedroom, 6 Bathroom Home Boasts Over 7,500 Sqft Of Above Ground Living Space. Step Into The Californian Open Concept Grand Main Floor, Backsplit To Soaring 15 Ft Ceilings In Family Room and Designer Kitchen, With 3 Elevated South Facing Garden Doors With Transoms For A Sun Filled Home. Chefs Kitchen With Top of The Line Sub Zero Fridge and Wolf Range, Custom Venta Hood, 12 X 8 Island Accented By Suspended Waffle and Floor To Ceiling Cabinets. The Main Floor Also Includes A Formal Dining Room, Office, And 2 Elevated Living Rooms Finished With Large Bookmatch Tile and Herringbone Hardwood Throughout. Spacious Master Bedroom With Juliette Balcony Has A Spa Oasis W/ 5 X 7 Shower and Soaker Tub, Accessible to W/I Closet With Centre Island. Additional Spacious Bedrooms Surround A Central Study Nook With Large Skylight Open To 3rd Floor Loft Retreat With A Large 22 X 22 Room Plus Covered Balcony Overlooking The Rouge Forest. An Entertainers Dream! Basement Features A Theatre Room, 2 Bedrooms and 2 Bathrooms W/ Rough-In For Kitchen For Separate Apartment, With Open Rec Area With Walkout To Backyard. Backyard Bliss With South Facing 16 X 32 Saltwater Pool And Two Large Sports Pads For Trampoline, Basketball, Etc. Accented By Mature Willow Tree, Dozens Of Cedar Trees And Turf So No Grass Avoiding Excess Lawn Maintenance. Perfect For Families, In Top Ranked EB Phin School District and Steps To Dunbarton and St. Mary's Highschools. No Expenses Spared - Over 200 Potlights, 200 Amp Service, Fully Spray Foamed, Wood Interior Doors, 9 1/4 Baseboard and Crown Mouldings, And More. Must See For Yourself! More details
    Listed by BEG BROTHERS REAL ESTATE
    LISTING DETAILS
    John Owen, Broker

  • 556 Rainy Day Drive in Pickering: Woodlands E12915482 - House

    556 Rainy Day Drive Woodlands Pickering L1V 5Z9
    Main Photo: 556 Rainy Day Drive in Pickering: Woodlands E12915482 - House

    556 Rainy Day Drive Pickering L1V 5Z9 Woodlands

    $1,199,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12915482
    Bedrooms:
    4
    Bathrooms:
    4
    You've never experienced a street quite like this-where neighbours truly know and look out for one another, creating a warm and welcoming sense of community. This meticulously maintained all-brick home offers 4 bedrooms and 4 bathrooms, and has been filled with years of love, laughter, and family memories. Thoughtfully designed for both everyday living and entertaining, the layout is flexible to suit your lifestyle. The main floor offers versatile spaces-currently configured with a home office and a large dining/gathering area-while the kitchen easily accommodates additional seating with an eat-in option. Step outside and discover a backyard that truly feels like an extension of the home. Complete with a natural gas fire pit, hot tub, pergola, covered deck, and perennial gardens, this outdoor space is both low maintenance and ideal for relaxing or hosting. It's your very own outdoor family room. Upstairs, the spacious primary bedroom features additional wardrobe storage, while the fully finished basement provides the perfect setting for movie nights, game nights, and holiday gatherings. Ample storage throughout the home ensures there's space for everything-from seasonal décor to pantry essentials. The widened driveway adds convenience, and the location is unbeatable. With quick access to Highway 401, transit, shopping, and everyday amenities, everything you need is within easy reach. Enjoy walks around the neighbourhood with a Second Cup Coffee or Booster Juice. Walking distance to Dunbarton High School, George Ashe Library, Freshco, Shopper's Drug Mart and more nearby shops-making daily life effortless and connected.This is more than a house-it's a place to grow, gather, and create your next chapter. Closing our chapter, and opening yours. See attached feature sheet for updates. More details
    Listed by REALTY ONE GROUP REVEAL
    LISTING DETAILS
    John Owen, Broker

  • 501 Sundown Crescent in Pickering: Woodlands E12875898 - House

    501 Sundown Crescent Woodlands Pickering L1V 6A7
    Main Photo: 501 Sundown Crescent in Pickering: Woodlands E12875898 - House

    501 Sundown Crescent Pickering L1V 6A7 Woodlands

    $1,299,900
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12875898
    Bedrooms:
    4
    Bathrooms:
    3
    Welcome to 501 Sundown Crescent, where traditional elegance meets modern functionality. 2 storey all brick home loaded with elegant upgrades and located on a quiet family friendly street. The updated, sun filled family sized kitchen is equipped with high end finishes including designer cabinetry, granite counter tops, stainless steel appliances, built-in wine fridge, pot lights and a walkout to the private backyard oasis. Hardwood flooring, crown moulding and wainscotting throughout main floor. Separate formal family room overlooking backyard with natural stone wood burning fireplace. Combined living/dining offers the perfect space to entertain, main floor updated laundry room with inside access to garage and separate side door entrance. The primary bedroom retreat offers a walk-in closet and updated, spa like bathroom including a seamless glass shower and free standing soaker tub. Updated main bathroom, great sized bedrooms and loads of closet space. Fully finished basement with second family/rec. room, natural gas fireplace, pot lights, large cold room/cantina and additional storage space. Enjoy warm summer nights in the fully private backyard which includes an integrated deck, hot tub with gazebo and matures hedges for added privacy. Exterior sprinkles system, updated light fixtures and window covering throughout. Full double car garage and 4 car driveway, no sidewalk. Great location with easy highway access, minutes to shopping, public transits, schools, parks and restaurants. More details
    Listed by MINCOM SOLUTIONS REALTY INC.
    LISTING DETAILS
    John Owen, Broker
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  • 1459 Old Forest Road in Pickering: Woodlands E12876926 - House

    1459 Old Forest Road Woodlands Pickering L1V 1N8
    Main Photo: 1459 Old Forest Road in Pickering: Woodlands E12876926 - House

    1459 Old Forest Road Pickering L1V 1N8 Woodlands

    $2,949,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12876926
    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

  • 1406 Old Forest Road in Pickering: Woodlands E12841612 - House

    1406 Old Forest Road Woodlands Pickering L1V 1N7
    Main Photo: 1406 Old Forest Road in Pickering: Woodlands E12841612 - House

    1406 Old Forest Road Pickering L1V 1N7 Woodlands

    $1,399,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12841612
    Bedrooms:
    4
    Bathrooms:
    4
    If you're looking for something truly unique, this is it! A stunning stone home on nearly 1/2 acre, backing onto the Petticoat Creek Ravine. Set back from the street, the property features a landscaped 50 ft frontage, a circular driveway, and a double car garage. Inside, the home has been beautifully renovated with an open-concept kitchen, a large breakfast bar, oversized windows that offer a fantastic view and so much light, and a walk-out to a balcony overlooking a breathtaking 385 ft deep lot surrounded by nature. The main floor includes a cozy family room with a stone fireplace, a bright and open living and dining area, and a large laundry room as well as a 2 piece powder room. Upstairs offers three spacious bedrooms, including a primary suite with beamed ceilings, a luxurious ensuite with walk-in shower, and a private deck with panoramic views. The finished lower level features a walk-out to the garden, a beautifully renovated bathroom, laminate floors, and a versatile study currently used as a bedroom. There is more space currently being used for an office. This exceptional property combines character, charm, and privacy-offering the best of country living in the city. Move-in ready and truly one of a kind! Located in Pickering's sought-after Woodlands community, just minutes to Petticoat Creek Conservation Area, waterfront trails, parks, and schools. Enjoy quick access to Highway 401, GO Transit, shopping, and restaurants while living on a quiet, tree-lined street surrounded by nature-offering the perfect blend of convenience and tranquility. More details
    Listed by REMAX CONNECT REALTY
    LISTING DETAILS
    John Owen, Broker

  • 127 755 Omega Drive in Pickering: Woodlands E12831568 - Condo Apartment

    127 755 Omega Drive Woodlands Pickering L1V 0H1
    Main Photo: 127 755 Omega Drive in Pickering: Woodlands E12831568 - Condo Apartment

    127 755 Omega Drive Pickering L1V 0H1 Woodlands

    $549,900
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    E12831568
    Bedrooms:
    2
    Bathrooms:
    2
    CENTRAL DISTRICT TOWNS - BRAND NEW HOME IN PRIME PICKERING LOCATION - AVAILABLE NOW AND READY FOR QUICK FINAL CLOSING - ONLY 5% DOWN This stunning new 2 Bedroom Bungalow Model, comes complete with Quartz Counters, S/S Appliances, One Underground Parking Space. Large Outdoor Terrace for your outdoor enjoyment. Walking distance to many shops and restaurants. Minutes to 401, Pickering Go and Pickering Town Centre... Perfect for the first time buyer - Buyer to confirm Eligibility for the GST/HST Rebate More details
    Listed by HARTLAND REALTY INC.
    LISTING DETAILS
    John Owen, Broker
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Data was last updated April 13, 2026 at 01:00 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.