Woodlands Homes for Sale

Woodlands Homes for Sale

Welcome to Woodlands, a charming neighborhood nestled in the heart of Pickering, Ontario. Known for its serene environment and family-friendly atmosphere, Woodlands offers a perfect blend of suburban tranquility and urban convenience. With lush green spaces, scenic walking trails, and proximity to beautiful Lake Ontario, residents enjoy a lifestyle that embraces both nature and community.

Woodlands is characterized by its diverse range of homes, making it an ideal location for families, young professionals, and retirees alike. From cozy bungalows to spacious two-story homes, there’s something for everyone. Many properties feature well-maintained gardens, ample backyard space, and modern amenities that cater to today’s discerning homeowner. The neighborhood is also known for its strong sense of community, where neighbors become friends and local events foster connections.

Families will appreciate the top-rated schools within the area, as well as the abundance of parks and recreational facilities that encourage an active lifestyle. The nearby Woodlands Park is a favorite spot for picnics, sports, and leisurely strolls, providing a perfect escape for residents of all ages.

For those seeking a vibrant community with a variety of homes for sale, Woodlands is an excellent choice. With its convenient access to major highways, shopping centers, and public transit, commuting to Toronto or other nearby cities is a breeze. Discover the charm of Woodlands and explore the available homes for sale—your dream home awaits in this delightful Pickering neighborhood!

Newest Woodlands Homes for Sale

$1,199,000
5 Beds ⋅ 3 Baths ⋅ E13637938 MLS
Exceptional Income Opportunity! This property features a fully legal basement apartment, permitted by the City as a Two-Dwelling House, currently generating $2,100 per month in rental income. Whether you're looking to offset your mortgage, invest in a high-performing income property, or accommodate extended family, this legal suite offers outstanding flexibility and long-term value.Welcome to 696 Sheppard Avenue, Pickering, a rare opportunity to own a spacious home on a premium square-shaped lot backing onto a ravine, combining privacy, convenience, and exceptional investment potential.Perfectly situated directly across from a high school and just 2 minutes from Highway 401, this home offers unbeatable accessibility for commuters and families. You'll also enjoy easy access to shopping, parks, public transit, and everyday amenities.This well-maintained home has seen significant updates, including a new roof (2022), new furnace (2022), and a brand-new asphalt driveway (2025). The expansive driveway accommodates up to 10 vehicles, in addition to a large attached garage, making it ideal for large families, car enthusiasts, or those who love to entertain their friends and familyThe picturesque ravine setting creates a peaceful backyard retreat while maintaining the convenience of city living. With its legal income-generating suite, premium lot, major mechanical updates, extensive parking, and prime location, 696 Sheppard Avenue is an exceptional opportunity for homeowners, investors, and multigenerational families alike.Don't miss your chance to own a property that offers the perfect balance of lifestyle, functionality, and reliable rental income.

696 Sheppard Avenue, Pickering
$2,689,900
6 Beds ⋅ 7 Baths ⋅ E13580966 MLS
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.

432 Sheppard Avenue, Pickering
$2,288,000
4 Beds ⋅ 4 Baths ⋅ E13544892 MLS
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.

1488 Rosebank Road, Pickering
$1,999,999
6 Beds ⋅ 7 Baths ⋅ E13530404 MLS
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.

832 Sheppard Avenue, Pickering
$1,850,000
5 Beds ⋅ 4 Baths ⋅ E13509302 MLS
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.

1449 Rosebank Road, Pickering
$1,187,000
4 Beds ⋅ 3 Baths ⋅ E13494064 MLS
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.

561 Cattail Court, Pickering
$1,649,000
6 Beds ⋅ 5 Baths ⋅ E13459550 MLS
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.

1482 Old Forest Road, Pickering
$2,250,000
4 Beds ⋅ 4 Baths ⋅ E13214954 MLS
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.

1436 Highbush Trail, Pickering
$2,649,000
7 Beds ⋅ 7 Baths ⋅ E13170706 MLS
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.*****

1427 Rosebank Road, Pickering
$2,800,000
7 Beds ⋅ 6 Baths ⋅ E13169162 MLS
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.

1411 Old Forest Road, Pickering
$2,499,000
6 Beds ⋅ 6 Baths ⋅ E13149064 MLS
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.

413 Sheppard Avenue, Pickering
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