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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  • 413 Sheppard Avenue in Pickering: Woodlands E13859658 - House

    413 Sheppard Avenue Woodlands Pickering L1V 1E6
    Main Photo: 413 Sheppard Avenue in Pickering: Woodlands E13859658 - House

    413 Sheppard Avenue Pickering L1V 1E6 Woodlands

    $2,299,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13859658
    Bedrooms:
    6
    Bathrooms:
    6
    Detached home in Pickering's Woodlands community, offering 4,920 sq. ft. above grade, 4+2bedrooms and 6 bathrooms. Built in 2020, with a finished walk-out basement, spacious principal rooms and a family room open to the kitchen. Set on a 50 x 157 ft. lot with an attached double garage and parking for eight vehicles. Municipal water and sewer. Flexible possession. More details
    Listed by RE/MAX MILLENNIUM REAL ESTATE
    LISTING DETAILS
    John Owen, Broker

  • 369 Toynevale Road in Pickering: Rosebank E13858210 - House

    369 Toynevale Road Rosebank Pickering L1W 2G9
    Main Photo: 369 Toynevale Road in Pickering: Rosebank E13858210 - House

    369 Toynevale Road Pickering L1W 2G9 Rosebank

    $1,999,999
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13858210
    Bedrooms:
    5
    Bathrooms:
    4
    Home custom-made in 2015, Urban retreat/mins to Toronto in coveted area/walk to lake & conservation areas, parks, shopping, transit & schools/stunning design w/5600 sf liv/entertainment area & dressed to impress/featuring hardwood & porcelain tiles thru-out, vaulted & cathedral ceilings, Custom B.I. cabinetry, Servers, Bookcases, Fireplaces, Floating Staircases, Home Theatre/Finished Lower Level W/Access to garages/skylights, Stone countertops/Fully Fenced & Landscaped Mature Lot... Gar Dr Opener & Remote (S), Bbq Bib, Upgraded trim, Baseboards, Plumbing Fixtures, 9,10,12 & 22 & Coffered Ceilings. More details
    Listed by HOMELIFE/MIRACLE REALTY LTD
    LISTING DETAILS
    John Owen, Broker

  • 732 West Shore Boulevard in Pickering: West Shore E13851934 - House

    732 West Shore Boulevard West Shore Pickering L1W 2V1
    Main Photo: 732 West Shore Boulevard in Pickering: West Shore E13851934 - House

    732 West Shore Boulevard Pickering L1W 2V1 West Shore

    $2,799,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13851934
    Bedrooms:
    7
    Bathrooms:
    5
    Experience refined waterfront community living in this extraordinary custom luxury residence,ideally situated in one of Pickering's most coveted lakeside communities. Showcasing aspectacular 20-foot ceiling in the family room, elevator access to all levels including thegarage, and a rare third-floor primary retreat, this one-of-a-kind home is thoughtfullydesigned to blend architectural grandeur with exceptional everyday living. An impressiveeight-vehicle parking capacity provides exceptional convenience for both everyday living andentertaining.Perfectly positioned to capture natural light from sunrise to sunset, soaring windowsilluminate beautiful living spaces, where timeless design and premium finishes create anatmosphere of effortless elegance. At the heart of the home, the chef-inspired kitchen is atrue showpiece, featuring premium Wolf appliances, an oversized island, separate prep kitchen,breakfast nook, serving station, and wet bar-creating the perfect setting for both intimatefamily moments and unforgettable entertaining.The second level offers four spacious bedrooms, each with direct ensuite access, while theprivate third-floor primary retreat serves as a luxurious sanctuary complete with its ownbalcony, an expansive walk-in closet and a spa-inspired ensuite featuring dual rainfallshowers, an integrated steam shower, and heated floors. The bright, mostly above-grade basement is a standout feature, offering the rare combinationof soaring 10-foot ceilings, oversized windows, a full kitchen, a cozy fireplace, and aseparate entrance. This thoughtfully designed space delivers exceptional flexibility formulti-generational living, guest accommodations, or income potential. Step outside to a beautiful backyard oasis surrounded by mature trees, where an expansivedeck, generous green space, and natural gas connections for both a BBQ and fire pit create aninviting backdrop for effortless outdoor entertaining in all seasons. More details
    Listed by ROYAL LEPAGE VISION REALTY
    LISTING DETAILS
    John Owen, Broker

  • 1275 Wharf Street in Pickering: Bay Ridges E13849130 - House

    1275 Wharf Street Bay Ridges Pickering L1W 1A2
    Main Photo: 1275 Wharf Street in Pickering: Bay Ridges E13849130 - House

    1275 Wharf Street Pickering L1W 1A2 Bay Ridges

    $2,600,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13849130
    Bedrooms:
    4
    Bathrooms:
    3
    An impressive 90 feet of private shoreline on Frenchman's Bay! This amazing property offers true direct and sheltered waterfront access a rarity anywhere in the GTA. Complete with 4-bedrooms and three full baths, this custom home offers a unique layout with breathtaking views from the second-story kitchen and living room, where expansive windows open onto a spacious wraparound veranda. Nestled in the heart of Frenchman's Bay Nautical Village, you're steps from the beach, scenic trails, marinas, and restaurants in a vibrant, southern-inspired community. This property offers an exceptional waterfront lifestyle. Paddleboarding, sailing, and kitesurfing in the summer or skating and ice fishing just steps from home in the winter. No matter what season, the views are always exceptional. The property also features a rebuilt seawall and private dock above all previous flood levels with capacity for multiple vessels with direct access to Lake Ontario. Lovingly maintained by its original owners, this timeless home is ready for its next chapter of sunsets, waterfront beauty, and year-round recreation. More details
    Listed by RE/MAX HALLMARK REALTY LTD.
    LISTING DETAILS
    John Owen, Broker

  • 1436 Highbush Trail in Pickering: Woodlands E13831620 - House

    1436 Highbush Trail Woodlands Pickering L1V 1N5
    Main Photo: 1436 Highbush Trail in Pickering: Woodlands E13831620 - House

    1436 Highbush Trail Pickering L1V 1N5 Woodlands

    $2,250,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13831620
    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

  • 5295 - 5315 Sideline 16 Road in Pickering: Rural Pickering E13819414 - House

    5295 - 5315 Sideline 16 Road Rural Pickering Pickering L1Y 1A1
    Main Photo: 5295 - 5315 Sideline 16 Road in Pickering: Rural Pickering E13819414 - House

    5295 - 5315 Sideline 16 Road Pickering L1Y 1A1 Rural Pickering

    $9,800,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13819414
    Bedrooms:
    8
    Bathrooms:
    6
    Welcome to Happy Valley Estate featuring 3 beautiful homes on 50+ acres that is breathtaking with its unmatchable rolling hills scenery and privacy. This "one-of-a-kind" property is an unparalleled estate that has been meticulously maintained and enjoyed for over 34 years. This impressive estate offers 3+acre bass fishing pond, 2+ km of groomed walking trails, 3 over-sized garages, large nautical themed party room, huge 2-story barn, unlimited wildlife plus a 100 ft. bridge crossing the pond with gazebo where you can sit and ponder the majestic beauty of it all. It is a retreat of timeless elegance once owned by the famous "Kortright" family of the Kortright Conservation Centre. This amazing property is 10 minutes north of Hwy. 407 and is centrally located between Uxbridge, Stouffville and Pickering. The 3 homes have a total of 8 bedrooms, 3 kitchens and 6 bathrooms. #5295 -1st home is approx. 3,000sq.ft. century style timeless masterpiece located upon the hill overlooking the pond. This home boasts vaulted ceilings, original homestead beams, massive stone fireplace, 3-car garage, walkout to cozy porch, 3 bdrms. huge 2-story 62' barn. #5305 - 2nd home is a beautiful spacious bungalow approx. 2000sq.ft. situated at the water's edge. This home boasts rare hand-cut fieldstone fireplace, floor-to-ceiling windows to maximize the water and nature view from inside or from the huge wrap around deck. There are 2 Bdrms., 4-season sunroom w/walkout and a 2-car detached garage w/huge party room above it. #5315 - 3rd home is approx. 1850sq.ft. 1-1/2 story nestled back in the towering mature trees featuring stunning custom-built 23' x 23' gazebo for enjoying the serenity and privacy. This home boasts cathedral ceilings, shiplap accent-wall, cozy woodburning stove, quartz counter tops, 3 bdrms, attached 2-car garage & single car garage w/tandem style carport. More details
    Listed by CENTURY 21 WENDA ALLEN REALTY
    LISTING DETAILS
    John Owen, Broker

  • House in Pickering

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    Main Photo: House in Pickering

    Contact for address details

    Residential Freehold
    LISTING DETAILS
    John Owen, Broker
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  • 700 Hillcrest Road in Pickering: West Shore E13814076 - House

    700 Hillcrest Road West Shore Pickering L1W 2P1
    Main Photo: 700 Hillcrest Road in Pickering: West Shore E13814076 - House

    700 Hillcrest Road Pickering L1W 2P1 West Shore

    $2,298,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13814076
    Bedrooms:
    4
    Bathrooms:
    5
    A spectacular newly built custom home in the prestigious West Shore community, proudly recognized as the winning home featured on HGTV's Top of the Block and one that should be at the top of your list. Offering 4,469 sq. ft. of thoughtfully designed luxury living space, this exceptional residence showcases award-winning design, outstanding craftsmanship, and premium finishes throughout. Striking curb appeal is defined by black-framed windows and a timeless natural stone and stucco facade. Inside, a bright open-concept layout is filled with natural light and features 10-ft ceilings, expansive windows, wide-plank hardwood floors, custom millwork, and a stunning fireplace surround. The chef-inspired kitchen is designed for both entertaining and everyday living, complete with premium appliances, quartz countertops, an oversized island, servery, and walk-in pantry. The second level offers 9-ft ceilings and a luxurious primary retreat featuring a bar area, walk-in closet, and spa-inspired ensuite, while additional bedrooms are generously sized with custom organizers and second-floor laundry adds everyday convenience. The fully finished lower level provides versatile living space with a gas fireplace and full bath, ideal for recreation, guests, a home gym, or media room. Outside, enjoy a private backyard with a large patio and BBQ gas line. Located just steps from the lake, waterfront trails, parks, top-rated schools, shopping, and with easy access to Highway 401, this remarkable property delivers the perfect blend of award-winning design, quality construction, and modern family living. Featured on HGTV's Top of the Block. Built to stand out. Designed to be remembered. More details
    Listed by RE/MAX REALTY ENTERPRISES INC.
    LISTING DETAILS
    John Owen, Broker

  • 3325 Hollywood Court in Pickering: Rural Pickering E13814006 - House

    3325 Hollywood Court Rural Pickering Pickering L1X 0A3
    Main Photo: 3325 Hollywood Court in Pickering: Rural Pickering E13814006 - House

    3325 Hollywood Court Pickering L1X 0A3 Rural Pickering

    $4,995,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13814006
    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 private1.5-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 kitchens how cases 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

  • 1486 Ashwood Gate in Pickering: Rougemount E13807930 - House

    1486 Ashwood Gate Rougemount Pickering L1V 6L1
    Main Photo: 1486 Ashwood Gate in Pickering: Rougemount E13807930 - House

    1486 Ashwood Gate Pickering L1V 6L1 Rougemount

    $1,980,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13807930
    Bedrooms:
    5
    Bathrooms:
    6
    Welcome to 1486 Ashwood Gate, a rare offering in the prestigious "Tall Trees Enclave" of Rougemount, where timeless architecture meets thoughtful customization on a quiet, family-friendly court steps to Rouge National Urban Park. This exceptional, 5 bedroom residence has been meticulously maintained and beautifully evolved over the years, offering expansive living space designed for both everyday comfort and elevated entertaining. The heart of the home is a stunning custom European-designed kitchen featuring premium built-in appliances including Sub-Zero fridge/freezer & Miele wall oven & microwave, complemented by an impressive oversized walk-in pantry-perfect for the modern family & avid entertainer alike. A unique and valuable addition sets this home apart: an expanded upper level retreat complete with a spacious bedroom, private ensuite, and walk-in closet-ideal for multigenerational living, guests or a private sanctuary. Generous principal rooms, refined finishes, and a functional layout provide exceptional versatility throughout. Step outside to a truly spectacular backyard oasis.Surrounded by mature trees for ultimate privacy, this resort-style setting features an inground swimming pool, extensive professional landscaping, and a covered gazebo- creating the perfect environment for relaxing, entertaining and enjoying summer to the fullest. Pride of ownership is evident throughout this warm and inviting home, lovingly cared for by the same family over the years.A rare opportunity to own a one-of-a-kind property in one of Pickering's most sought -after executive communities. More details
    Listed by REVEL REALTY INC.
    LISTING DETAILS
    John Owen, Broker
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Data was last updated October 5, 2026 at 06:15 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.