Rosebank & Sheppard Real Estate for Sale

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.

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

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.

Located on one of Pickering's most prestigious streets, this stone and brick residence offers over 3,300 sqft. Main Floor with hardwood throughout, modern kitchen, family room and separate living and dining rooms. Upstairs, you'll find 5 spacious bedrooms (3 with ensuite baths), plus a finished 2-bedroom basement suite, with a second kitchen this home is ideal for large or multi-generational families. Large landscaped backyard with endless potential to make this truly your own. A rare opportunity in one of Pickering's most sought-after neighbourhoods. Minutes To Shopping, Parks And Great Schools.

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.

Welcome to this exceptional 3-storey family home in the highly sought-after Woodland community of Pickering-where space, flexibility, and lifestyle come together beautifully. Offering 2,918 sq ft, this rare true 5-bedroom, 4-bathroom home features a versatile third-floor loft-perfect as a private nanny or in-law suite, home office, or retreat for adult children. Thoughtfully updated with professionally painted interiors in modern, neutral tones (2023 & 2026), the home feels fresh, bright, and move-in ready. The spacious kitchen features stainless steel appliances, including New Dishwasher (March 2026), loads of cabinet space, LED lighting and flows to a sun-filled, south-facing solarium-where your family can eat and large enough for year-round entertaining. The mostly finished basement is perfect for in-laws, children, entertainment and storage. Families will love the unbeatable location-just steps to parks, schools, transit, and shopping-making everyday living effortless. A rare opportunity to own a home that truly grows with you in one of Pickering's most family-friendly neighbourhoods. One seller is a RREA.

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, 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!