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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  • 1779 Woodview Avenue in Pickering: Highbush E13215732 - House

    1779 Woodview Avenue Highbush Pickering L1V 1L3
    Main Photo: 1779 Woodview Avenue in Pickering: Highbush E13215732 - House

    1779 Woodview Avenue Pickering L1V 1L3 Highbush

    $1,949,898
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13215732
    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

  • 3325 Hollywood Court in Pickering: Rural Pickering E13215550 - House

    3325 Hollywood Court Rural Pickering Pickering L1X 0A3
    Main Photo: 3325 Hollywood Court in Pickering: Rural Pickering E13215550 - House

    3325 Hollywood Court Pickering L1X 0A3 Rural Pickering

    $4,995,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13215550
    Bedrooms:
    7
    Bathrooms:
    9
    Set in a quiet enclave of prestigious homes, this exceptional 11,500 sq. ft. estate (including built in garage) sits on a private 1.5-acre lot backing onto a serene forest. This elegant residence offers 7 spacious bedrooms, all with walk-in closets, including 6 with ensuite baths, and a total of 9 washrooms. The open-concept main floor features soaring 20 ft. cathedral ceilings, and dramatic floor-to-ceiling windows overlooking the expansive, private backyard. Designed for both effortless entertaining and elevated everyday living, the kitchen showcases the rare luxury of two expansive islands; a standout feature in sophisticated, open-concept homes. Thoughtfully designed to create both beauty and flow, the dual-island layout allows for dedicated culinary and social spaces, balancing function and style. The main floor primary suite spans nearly 1,000 sq. ft., offering a luxurious retreat. The second level hosts 4 generously sized bedrooms, while the finished lower level with 10 ft. ceilings includes 2 additional bedrooms and extensive additional living space all with floor to ceiling windows, perfect for extended family or guests. Two staircases seamlessly connect all three levels, enhancing both flow and functionality. A circular driveway leads to a 1,700 sf four-car garage with double height ceilings, ideal for car lifts. Additional features include 3 fireplaces, a home gym with glass wall and doors, a beautifully appointed, temperature controlled wine cellar with room for over 300 bottles tucked behind a bar and kitchen area. This is a thoughtfully designed home ideal for large families and multi-generational living. A rare offering combining scale, privacy, and refined living in an exclusive setting. More details
    Listed by BOSLEY REAL ESTATE LTD.
    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

  • 1771 Woodview Avenue in Pickering: Highbush E13207788 - House

    1771 Woodview Avenue Highbush Pickering L1V 1L3
    Main Photo: 1771 Woodview Avenue in Pickering: Highbush E13207788 - House

    1771 Woodview Avenue Pickering L1V 1L3 Highbush

    $2,158,800
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13207788
    Bedrooms:
    4
    Bathrooms:
    5
    Exceptional Custom Built Residence with over 4600 Sqft of Finished Luxurious Details & Thoughtful Design Throughout!! Main Floor Features Dramatic 10 Ft Ceilings! Second Floor and Basement Offer Generous 9 Ft Ceilings for an Airy, Spacious Feel!! The Gourmet Luxury Kitchen is a Chef's Dream, Showcasing Premium NIICO Custom Cabinetry, an Extra-Large Island Ideal for Entertaining, Built-In Panelled Refrigerator, Built-In Ovens, and a High-End 36" Gas Cooktop!! Adjacent Butler Servery with Walk-In Pantry Provides Ample Storage and Convenience! Step Out From the Kitchen to a Beautiful Covered Finished Patio For Seamless Indoor-Outdoor Living. The Open-Concept Family Room Impresses with Custom Built-In Cabinets, a Cozy Gas Fireplace, and Elegant Waffled Ceilings!! Separate Formal Living and Dining Rooms Feature Exquisite Wainscoting & Plaster Moldings! Spacious Mud Room with Built-In Cabinets and Coat Closet adds Everyday Practicality. The 2nd Floor Features the Luxurious Primary Suite and Includes a Spa-Like 5-Piece Ensuite Bath and an Extra-Large Walk-In Closet with Custom Built-In Cabinetry!! The Convenient Second-Floor Laundry Features Custom Cabinets and Granite Counters. All Additional Bedrooms Offer Private Ensuite Baths and Walk-In Closets For Ultimate Comfort and Privacy! Set On a Premium 50 Ft X 230 Ft Lot, this Property Provides Ample Space, Privacy, and Endless Outdoor Potential. A Rare Opportunity to own a Meticulously Crafted Custom Home Combining Modern Luxury with Timeless Elegance!! More details
    Listed by REALTY EXECUTIVES PLUS LTD
    LISTING DETAILS
    John Owen, Broker

  • 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
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Data was last updated May 30, 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.