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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  • 699 Front Road in Pickering: Bay Ridges E13240426 - House

    699 Front Road Bay Ridges Pickering L1W 1P1
    Main Photo: 699 Front Road in Pickering: Bay Ridges E13240426 - House

    699 Front Road Pickering L1W 1P1 Bay Ridges

    $2,199,900
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13240426
    Bedrooms:
    5
    Bathrooms:
    4
    A masterclass in architectural integrity, this custom-designed residence is situated in the coveted lakeside community of Bay Ridges with gorgeous views of Frenchman's Bay. Located moments from the beach, waterfront trail, marina, restaurants, shops, parks, and the GO station. From the street, the home establishes an immediate presence defined by a unique porte-cochere design, natural stone accents with Indiana limestone sills, and custom standing seam metal roofing accents. Inside, the layout balances grand proportions with refined finishes, featuring soaring 10-foot ceilings, solid Canadian oak flooring and 10-inch plaster crown mouldings. The great room is anchored by a gas fireplace surrounded in natural stone alongside a hidden entertainment center featuring an integrated 5-speaker surround sound system. The kitchen is a chefs and entertainers dream with a massive 10-foot island topped with Brazilian super white quartzite, pure white Italian quartz perimeters, Carrera marble backsplashes, high end appliances including a 36 inch Jenn-Air Gas Oven/Range and a walk-in pantry with a secondary refrigerator. The main level is completed by a practical mudroom with a dedicated dog/pet wash station. Separate area on the main floor complete with a bedroom, living room and washroom...Great potential for an in-law suite. Upstairs, the second level offers 9-foot ceilings, upper-level laundry, and private walk-in closets in all bedrooms. The primary retreat functions as a secluded sanctuary with a tray ceiling, automated blinds, a second gas fireplace, a walk-out balcony with views of Frenchman' Bay, and an ensuite with heated floors and a glass shower. 8-foot double garden doors from the family room open up to a 375-sq-ft flagstone patio with a covered roof and outdoor Napoleon kitchen. Custom built gas fire-pit with patio surround. The lawns have a 5-zone sprinkler system. Completing the estate is a detached garage finished to the same high standard as the main home. More details
    Listed by RE/MAX ROUGE RIVER REALTY LTD.
    LISTING DETAILS
    John Owen, Broker

  • 1995 Concession 8 Road in Pickering: Rural Pickering E13236068 - House

    1995 Concession 8 Road Rural Pickering Pickering L1Y 1A2
    Main Photo: 1995 Concession 8 Road in Pickering: Rural Pickering E13236068 - House

    1995 Concession 8 Road Pickering L1Y 1A2 Rural Pickering

    $2,089,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13236068
    Bedrooms:
    5
    Bathrooms:
    4
    The ultimate in privacy and tranquility. Set on 7 picturesque acres, this expansive and elegant bungalow offers complete serenity without sacrificing accessibility. Inside, an elegant main floor is designed for both everyday living and entertaining, featuring a spacious open-concept kitchen with quartz countertops and generously sized principal rooms. Large bedrooms provide exceptional comfort, while the primary suite is a true retreat, complete with an airy ensuite bath. From the main living space, step out to the backyard deck complete with a hot tub, an inviting extension of the home and perfect for unwinding in a private natural setting. Surrounded by a mature hardwood forest and Crown land, this property provides a rare and opportunity to escape development and enjoy an unparalleled connection to nature. The partially finished basement, featuring impressive 9-foot ceilings, offers a blank canvas ready to be customized to suit your lifestyle and vision. Perfectly positioned across from Four Seasons Country Club and just minutes to the 407, Stouffville, Pickering, and Uxbridge, this exceptional property combines peaceful country living with unmatched convenience. A rare opportunity to enjoy space, privacy, and connection, all in one remarkable setting. More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
    LISTING DETAILS
    John Owen, Broker

  • 4780 Westney Road in Pickering: Rural Pickering E13230918 - House

    4780 Westney Road Rural Pickering Pickering L1Y 1A2
    Main Photo: 4780 Westney Road in Pickering: Rural Pickering E13230918 - House

    4780 Westney Road Pickering L1Y 1A2 Rural Pickering

    $2,395,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13230918
    Bedrooms:
    6
    Bathrooms:
    4
    Welcome to 4780 Westney Rd N, a rare opportunity to own a completely turnkey, meticulously maintained executive home offering peaceful country living & convenient access to the city. Set on over 15 serene acres, this exceptional 5+1 bedroom property offers privacy, space, & versatility for large families or multi-generational living while truly checking all the boxes. A long private driveway & beautiful curb appeal welcomes you to a thoughtfully designed home featuring spacious rooms, a formal dining room & cozy family room. The chef-inspired custom kitchen features high-end appliances, generous prep space, & seamless flow for everyday living & entertaining. Enjoy recent renovations to the kitchen & bathrooms, updated light fixtures, & heated flooring in the living & eating areas adding a fresh upscale feel throughout. Expansive windows showcase stunning views & fill the home with natural light. Thoughtfully designed, this home also features convenient upstairs laundry. The primary suite is a true retreat with custom cabinetry, a spa-inspired 5-pc ensuite, & a private balcony overlooking the property. The fully finished basement offers in-law suite capabilities & incredible flexibility for extended family or guests. Outside, enjoy the tranquility & endless possibilities, along with a beautiful deck & hot tub perfectly positioned to take in the views. An impressive 32' x 64' heated workshop featuring two front loading doors & an additional rear door is ideal for hobbyists or contractors. A Generac generator provides added peace of mind year-round. Conveniently located just minutes to York Region & Toronto with quick access to Hwy 407, you'll enjoy the rare luxury of total privacy without sacrificing convenience. Property currently benefits from farm tax classification, offering exceptionally affordable property taxes for a property of this size & caliber. Surrounded by nature yet close to every amenity imaginable, this is the ultimate blend of town & country living. More details
    Listed by The Nook Realty Inc.
    LISTING DETAILS
    John Owen, Broker

  • 506 Rougemount Drive in Pickering: Rosebank E13230708 - House

    506 Rougemount Drive Rosebank Pickering L1W 2B9
    Main Photo: 506 Rougemount Drive in Pickering: Rosebank E13230708 - House

    506 Rougemount Drive Pickering L1W 2B9 Rosebank

    $2,699,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13230708
    Bedrooms:
    6
    Bathrooms:
    6
    Welcome home to 506 Rougemount Drive, set on one of Pickering's most coveted streets and backing directly onto the protected Rouge Valley. This exceptional ultra-modern residence offers nearly 4,000 square feet above grade, complemented by a fully finished walk-out lower level designed for seamless multi-generational living, along with a three-car garage featuring a tandem configuration. From the moment you arrive, the home's presence is undeniable, defined by clean architectural lines, expansive windows, and a refined façade set against a private natural backdrop. Inside, thoughtfully designed living spaces offer elevated finishes, generous principal rooms, and a layout that balances everyday comfort with upscale entertaining. The main level is filled with natural light and anchored by a sophisticated kitchen with premium materials and timeless design. The upper level features four spacious bedrooms with ensuite access, including a beautifully appointed primary retreat complete with a spa-inspired five-piece bath. The walk-out lower level offers a fully contained two-bedroom in-law suite, ideal for extended family or flexible living arrangements. Positioned on a premium ravine lot, the property offers a rare lifestyle defined by privacy, open views, and direct connection to nature, where sunsets and surrounding wildlife become part of the everyday experience. Conveniently located within close proximity to GO Transit and Highway 401, this home provides efficient access to the downtown core while being just moments from waterfront trails, cycling routes, and scenic green space. More details
    Listed by RE/MAX HALLMARK FIRST GROUP REALTY LTD.
    LISTING DETAILS
    John Owen, Broker

  • 492 Rougemount Drive in Pickering: Rosebank E13223498 - House

    492 Rougemount Drive Rosebank Pickering L1W 2B9
    Main Photo: 492 Rougemount Drive in Pickering: Rosebank E13223498 - House

    492 Rougemount Drive Pickering L1W 2B9 Rosebank

    $3,649,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13223498
    Bedrooms:
    7
    Bathrooms:
    7
    A truly One-of-a-Kind Custom Luxury home, nestled on a ravine lot with lots of sunlight, just minutes from the beach. This meticulously upgraded home blends refined design, advanced technology, and exceptional craftsmanship throughout. Features include heated entrance, 10-ft ceiling throughout home, 18-ft ceiling in Great room with custom dome, 8-ft doors throughout, hardwood flooring, granite finishes, and *two master bedrooms* (main & 2nd floor), both with walk-in closets, 5- piece ensuite with jacuzzi. All bedrooms have adjoining full bathrooms and ample closet space for storage. Enjoy a state-of-the-art audio system, high-speed networking throughout, custom mill work and thoughtfully designed living spaces including a theatre room, home office, and finished walk-out basement. The Great Room stuns with open to above area, with custom dome ceiling, fireplace feature wall, and seamless indoor-outdoor flow with pot lights throughout the home. Step outside to a professionally landscaped backyard oasis with a 700-sq-ft entertainment pad, low maintenance turf throughout the backyard, water features, fire pit, gazebo, glass railings, and LED lighting- all backing onto a beautiful and serene creek. Additional highlights include dual furnaces & amp; 2 A/Cs, tank less water heaters, smart security system, custom closets, 18 car drive-around driveway with fountain, and a heated entrance inside the home. An extraordinary home offering luxury, privacy, and modern living in one of Pickering's most sought-after neighbourhoods. See Attached List Of All Upgrades, $$$ In Landscaping, 21 Invisible Stealth Speakers, 2 Furnaces, 2 Air Conditioners, Hunter Douglas Blinds Throughout, Rough-in for Kitchen in basement and Theatre Room in basement. Over 8000 sq feet of living space; 5455 sq ft above grade and 2800 sq ft walk out basement. More details
    Listed by HOMELIFE SILVERCITY REALTY INC.
    LISTING DETAILS
    John Owen, Broker

  • 1921 Bonita Avenue in Pickering: Dunbarton E13220994 - House

    1921 Bonita Avenue Dunbarton Pickering L1V 3N1
    Main Photo: 1921 Bonita Avenue in Pickering: Dunbarton E13220994 - House

    1921 Bonita Avenue Pickering L1V 3N1 Dunbarton

    $3,300,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13220994
    Bedrooms:
    5
    Bathrooms:
    6
    Exquisite Custom-Built Home in Prestigious Pickering Neighbourhood. Soaring 10' Ceilings on the Main Floor. Gourmet Kitchen with Solid Walnut Tabletop Island, Walk-In Pantry, High-End Appliances, Ceasarstone Counters & Cast Rangehood. Master Is A Retreat with Separate Seating Area, His & Her Walk-In Closets & Spa-Like Ensuite. Extensive Lighting Including Led Pot Lights & 3 Stunning Chandeliers on Electric Hoists. 2 Elegant Town & Country Gas Fireplaces. professionally finished basement with moveable wet bar/dishwasher/fridge, 2 utility rooms, gym room and in law suite. 2Car garage plus 2nd Tandem drive=thru garage, both with heated floors Main floor laundry features abundant cabinetry & Granite countertop, 2nd laundry on 2nd floor,5491 sq ft plus 2764 sq ft finished basement. This house is a true showstopper. More details
    Listed by SUTTON GROUP-HERITAGE REALTY INC.
    LISTING DETAILS
    John Owen, Broker

  • 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
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Data was last updated June 5, 2026 at 02:15 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.