Houses for sale in Pickering over 2000000 | 2 million

Newest MLS listings in Pickering over 2000000 - Rouge Park, Highbush, Rougemount, Amberlea, Woodlands, Dunbarton, Liverpool, Town Centre, Rosebank, West Shore, Bay Ridges

Pickering houses for sale over 2 million | 2,000,000

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  • 334 Dyson Road in Pickering: Rosebank E13171242 - House

    334 Dyson Road Rosebank Pickering L1W 2M9
    Main Photo: 334 Dyson Road in Pickering: Rosebank E13171242 - House

    334 Dyson Road Pickering L1W 2M9 Rosebank

    $2,299,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13171242
    Bedrooms:
    4
    Bathrooms:
    4
    Absolutely stunning custom-built waterfront home on an exceptional 75 x 314 ft lot in Pickering's prestigious Rosebank community, featuring 23 feet of frontage on the Rouge River. This impressive 2-storey detached residence offers approximately 5,000 sq ft of beautifully designed living space, including a fully finished walkout basement with home theatre, gym, and steam room. The main floor showcases a bright open-concept layout with dramatic floor-to-ceiling bi-fold glass doors throughout, seamlessly connecting the interior to the resort-style backyard with luxury pool setting, mature treetops, and breathtaking Rouge River views. Designer AYA kitchen features a massive centre island, premium Miele stainless steel appliances, custom cabinetry, and a spacious walk-in pantry with additional prep area, sink, and built-ins. Elegant family room with stunning brick fireplace, oversized dining area, and rare indoor barbecue lounge with soaring 20-ft cathedral ceilings, exposed wood beam, wood-burning stove, and walkout to the pool area. Main floor also includes a private home office with AYA custom built-in desk and cabinetry. Upper-level features 3 spacious bedrooms, including a luxurious primary retreat overlooking the Rouge River with spa-inspired 5-piece ensuite, glass shower, freestanding tub, two-way fireplace, sitting area, oversized walk-in closet with custom built-ins, and ample space for king-size furnishings. Over $250,000 spent on professional landscaping and interlocking throughout the front, side, and rear grounds. Resort-inspired backyard features an $200,000 custom pool and hot tub built with insulated ICF construction and concrete finish. Located in one of Pickering's most exclusive waterfront communities, close to Rouge National Urban Park, top-rated schools, waterfront trails, GO Transit, and Highway 401. More details
    Listed by RE/MAX HALLMARK REALTY LTD.
    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

  • 389 Rosebank Road in Pickering: Rosebank E13170160 - House

    389 Rosebank Road Rosebank Pickering L1W 2N3
    Main Photo: 389 Rosebank Road in Pickering: Rosebank E13170160 - House

    389 Rosebank Road Pickering L1W 2N3 Rosebank

    $1,998,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13170160
    Bedrooms:
    6
    Bathrooms:
    6
    Be the first to live in this brand new custom home, move-in ready for Fall 2026. Built by award-winning Highglen Homes-over 35 years of crafting homes! This transitional design features a stone exterior, blending traditional style with a bright, contemporary interior layout. Spanning 5,207 sq ft of living space, this 5 +1 bed, 6 bath home comes with a finished basement and separate walk-up entrance. Includes full 7-year Tarion warranty protection. Custom kitchen with appliance package, and plenty of storage with the attached servery, walk-in butler's pantry, and a double row of upper cabinets. Predominant ceiling heights: 10' main, 9' second, 8' third, with architectural coffered, tray, and vaulted ceiling upgrades. An extra-wide 4' oak staircase leads to upper levels where you'll find 4 bathrooms and 5 large bedrooms, each with walk-in closets, including a large primary suite with double walk-ins, custom millwork, and a 5pc ensuite bath. Floor plans attached. Sample finishing photos from neighbouring model home. Taxes not yet assessed. More details
    Listed by REMAX CONNECT REALTY
    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

  • 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

    $2,799,000
    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

  • 363 Rosebank Road in Pickering: Rosebank E13162808 - House

    363 Rosebank Road Rosebank Pickering L1W 2N3
    Main Photo: 363 Rosebank Road in Pickering: Rosebank E13162808 - House

    363 Rosebank Road Pickering L1W 2N3 Rosebank

    $1,925,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13162808
    Bedrooms:
    5
    Bathrooms:
    5
    Welcome To 363 Rosebank Road, A Stunning Custom-Built Masterpiece (2021) With 4+1 Bedrooms & 5 Bathrooms In The Heart Of Durham Region.Each Room Is A Statement. Built With Impeccable Craftsmanship And Designer Finishes, This Home Effortlessly Blends Sophistication With Warmth. A Grand Entryway Welcomes You Through Oversized Windows, Flooding The Interior With Natural Light And Offering Inviting Glimpses Of The Serene Backyard. The Chef's Kitchen Is A Showstopper. With Premium Appliances, Sleek Cabinetry, Pot Filler & Generous Island The Doubles As A Gathering Spot. From Casual Mornings To Festive Evenings, It's Built For Both Function & Flair.On The Main Level, You'll Find Luxe Finishes And Thoughtful Details At Every Turn, With Easy Access To A Beautiful Outdoor Space That's Perfect For Summer BBQs or Quiet Mornings With Coffee.Upstairs, The Primary Suite Is A Sanctuary With A Generous Bedroom, Soothing Views, A Spa-Style Ensuite And Ample Closet Space. Three Additional Bedrooms Plus Two More Bathrooms Make This Level Ideal For Families, Guests Or Even A Home-Office Setup.The Third Floor Features A Spacious 980 Sq Ft Loft With A Wet Bar That Can Be Used For Recreation Or An Additional Bedroom.The Lower Level Has 2 Cold Storage Rooms & Further Extends Your Living Space With A Fully Finished Bonus Room (Bedroom #5), A Finished Bathroom & Endless Possibilities - Gym? Media Room? Playroom? You Choose.Behind It All: Smart Systems, Quality Building Materials And A Location That Brings Convenience And Lifestyle. Minutes To Shopping, Parks, And Great Schools, This Home Helps You Feel Connected With Nature While Enjoying Your Own Private Retreat. More details
    Listed by LPT REALTY
    LISTING DETAILS
    John Owen, Broker

  • 5455 Hoxton Street in Pickering: Rural Pickering E13158814 - House

    5455 Hoxton Street Rural Pickering Pickering L1Y 1A3
    Main Photo: 5455 Hoxton Street in Pickering: Rural Pickering E13158814 - House

    5455 Hoxton Street Pickering L1Y 1A3 Rural Pickering

    $2,199,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13158814
    Bedrooms:
    6
    Bathrooms:
    4
    Welcome to 5455 Hoxton Street, a private country estate in Claremont, one of Durham's most prestigious and sought-after neighborhoods. Situated on 8 acres, backing up onto the Oak Ridges Moraine. Offering approximately 5,000 sq. ft. of thoughtfully curated living space, the home makes a striking first impression with its elegant façade. Inside you will find 3+2 bedrooms, a sauna and 4 bathrooms, including an in-law suite or professional home office with a private entrance. The estate features zoned controlled heating for year round comfort and entertainment. Extensively updated with major improvements throughout, including a new roof (2022), water heater (2022), furnace (2025), brand-new deck (2025), 2 pergolas (2025), in-law suite deck (2025), pool (2025), and interlocking stonework (2025). The backyard is fully enclosed with a wooden fence (2023), plus a separate fenced pool area (2023) for added safety and privacy. An invisible fence surrounding the entire property (2022) adds convenience for pet owners. Outdoor living is second to none with a beautiful pool, expansive entertaining areas, 2 pergolas, and endless room to enjoy nature. The barn is fully serviced with water heater, plumbing, and electricity, offering incredible potential for hobbies, storage, workshop space, or future use. A rare opportunity to own a turnkey country property with modern upgrades, income or multi-family potential, and unmatched outdoor amenities. More details
    Listed by RE/MAX ACE REALTY INC.
    LISTING DETAILS
    John Owen, Broker

  • 1779 WOODVIEW Avenue in Pickering: Highbush E13149428 - House

    1779 WOODVIEW Avenue Highbush Pickering L1V 1L3
    Main Photo: 1779 WOODVIEW Avenue in Pickering: Highbush E13149428 - House

    1779 WOODVIEW Avenue Pickering L1V 1L3 Highbush

    $2,185,898
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13149428
    Bedrooms:
    6
    Bathrooms:
    5
    An unmatched real estate opportunity in prime Pickering! This custom-built, all-brick executive home boasts over 3,400 sq ft of massive above-grade square footage and sits on an exceptionally deep 60 x 263 ft lot, offering rare scale and privacy. Built by a builder for his own family, the home features outstanding structural integrity-the ultimate canvas to customize and create your dream estate.The main level features a sprawling layout with a large kitchen opening to a bright family room, a formal living room with cathedral ceilings, a dining room, and a private office. Upstairs, discover 4 massive bedrooms, including a primary suite with a 6-piece ensuite.The lower level maximizes the home's immense size, offering a fully self-contained 1-bedroom in-law suite with its own separate enclosed entrance. Strategically designed, the basement also features an additional large living room and separate bedroom independent of the apartment. This versatile layout gives you the perfect opportunity to easily expand the suite, or retain a massive private recreation space for your own family's use.Capitalize on premium exterior features: a circular driveway, a rare double-car garage with a tandem workshop configuration, and a park-like backyard. Major elements offer excellent peace of mind, featuring updated bathrooms, roof shingles updated in 2013 with a 50-year manufacturer's warranty, and a furnace and central A/C updated approximately 5 years ago. A home of this size, on a lot this magnificent, in this location, is truly hard to find. More details
    Listed by RE/MAX HALLMARK FIRST GROUP 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

  • 752 Hillview Crescent in Pickering: West Shore E13125872 - House

    752 Hillview Crescent West Shore Pickering L1W 2S1
    Main Photo: 752 Hillview Crescent in Pickering: West Shore E13125872 - House

    752 Hillview Crescent Pickering L1W 2S1 West Shore

    $2,298,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13125872
    Bedrooms:
    5
    Bathrooms:
    5
    Welcome to this elegant, custom-built family home, where no expense was spared in achieving the finest attention to detail and modern luxury. This impressive retreat is ideally located just minutes from the stunning views of Frenchman's Bay, adjacent to a park and scenic trail system. The interior features rich hardwood floors, premium tiling, and a chef's kitchen boasting granite countertops, a giant island, and a walkout to the backyard. The main living area includes a cozy built-in gas fireplace and sophisticated built-in shelving, while the entire home is smart-wired with built-in speakers and security cameras for ultimate convenience and peace of mind. With quick access to public transit, shopping centers, and the 401, this home offers a perfect blend of high-end features and prime, convenient location near the lake.Welcome to this elegant, custom-built family home, where no expense was spared in achieving the finest attention to detail and modern luxury. This impressive retreat is ideally located just minutes from the stunning views of Frenchman's Bay, adjacent to a park and scenic trail system. The interior features rich hardwood floors, premium tiling, and a chef's kitchen boasting granite countertops, a giant island, and a walkout to the backyard. The main living area includes a cozy built-in gas fireplace and sophisticated built-in shelving, while the entire home is smart-wired with built-in speakers and security cameras for ultimate convenience and peace of mind. With quick access to public transit, shopping centers, and the 401, this home offers a perfect blend of high-end features and prime, convenient location near the lake. More details
    Listed by RE/MAX HALLMARK FIRST GROUP REALTY LTD.
    LISTING DETAILS
    John Owen, Broker
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Data was last updated May 26, 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.