House for sale in Whitby homes over 2000000

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Whitby homes for sale above 2,000,000

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1-10/13

  • 15 Shepherd Road in Whitby: Rural Whitby E12616700 - House

    15 Shepherd Road Rural Whitby Whitby L1M 1G8
    Main Photo: 15 Shepherd Road in Whitby: Rural Whitby E12616700 - House

    15 Shepherd Road Whitby L1M 1G8 Rural Whitby

    $2,800,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12616700
    Bedrooms:
    7
    Bathrooms:
    7
    Discover winter luxury at 15 Shepherd Road, a custom luxury bungalow set on a premium 102.48 ft x 352.51 ft lot backing onto the peaceful winter landscape of Heber Down Conservation Area. This beautifully updated home features four main-floor bedrooms, each with its own en-suite and walk-in closet, 10-foot ceilings, new engineered hardwood floors, fresh paint (2025), and a stunning great room with a 16-foot cathedral ceiling and gas fireplace. The brand-new kitchen includes stainless steel appliances, crown moulding, large baseboards, and California shutters. The primary suite offers a custom ceiling with pot lights, a spacious walk-in dressing room, and a 5-piece spa-like en-suite with views of the pool and conservation area. The finished walk-out basement adds exceptional versatility with three additional bedrooms, a gym, two recreation rooms, a gas fireplace, and a rough-in kitchen ideal for multi-generational living. The attached workshop with 60 Amp service provides space for hobbies, a golf simulator, or storage. With its brick, stone, and stucco exterior, updated pool system (new liner, heater, UV system Aug 2025), and no rental items, this is a rare opportunity in prestigious Macedonian Village-luxury, privacy, and comfort in every season. More details
    Listed by RE/MAX HALLMARK FIRST GROUP REALTY LTD.
    LISTING DETAILS
    John Owen, Broker

  • 10 Philips Road in Whitby: Rural Whitby E12610450 - House

    10 Philips Road Rural Whitby Whitby L1M 1G7
    Main Photo: 10 Philips Road in Whitby: Rural Whitby E12610450 - House

    10 Philips Road Whitby L1M 1G7 Rural Whitby

    $3,500,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12610450
    Bedrooms:
    5
    Bathrooms:
    5
    Winter-Ready Estate-Style Bungaloft in Macedonian Village - Brand New with Tarion Warranty. Welcome to 10 Phillips Road, a custom-built luxury bungaloft with a walkout Basement nestled on a 125' x 278' premium lot in the exclusive, private community of Macedonian Village, Whitby. Surrounded by mature trees and winter scenery, and just a short walk to Heber Down Conservation Area, this Tarion-warranted residence offers over 4,000 sq. ft. of meticulously crafted living space-perfect for cozy winter living and year-round enjoyment. Step into the impressive 12-ft foyer, where an open-concept layout and expansive windows capture serene seasonal views and natural light. The great room is a true winter showpiece, featuring a 17-ft cathedral ceiling and a gas fireplace-an ideal setting for gathering, relaxing, and enjoying the warmth of home. The chef-inspired kitchen elevates every meal with Fisher & Paykel built-in appliances, quartz countertops, and a full-height quartz backsplash. A formal dining area allows for effortless entertaining throughout the winter season. The main-floor primary suite is a peaceful retreat, complete with an 11-foot tray ceiling with pot lights, an oversized walk-in dressing room with custom built-ins, and a spa-like 5-piece ensuite featuring a curbless glass shower and double vanity. Built-in speakers, a central vacuum, and upscale finishes add to the home's refined comfort. A third main-floor bedroom doubles perfectly as a home office. 10 Phillips blends architectural elegance with everyday functionality, all set within a tranquil community steps from trails and a neighbourhood park. Enjoy the peace of nature while staying close to town conveniences. Immediate occupancy available. More details
    Listed by RE/MAX HALLMARK FIRST GROUP REALTY LTD.
    LISTING DETAILS
    John Owen, Broker

  • 10 Franklin Crescent in Whitby: Rural Whitby E12597062 - House

    10 Franklin Crescent Rural Whitby Whitby L0B 1A0
    Main Photo: 10 Franklin Crescent in Whitby: Rural Whitby E12597062 - House

    10 Franklin Crescent Whitby L0B 1A0 Rural Whitby

    $2,750,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12597062
    Bedrooms:
    3
    Bathrooms:
    4
    Experience luxury and tranquility in this stunning new build on 1.43 acres in Whitby, Ontario. Boasting 3,210 sq ft of sophisticated living space above the basement, this elegant home offers 3 spacious bedrooms, 4 bathrooms, and dual 2-car garages with 14 ceilings. Nestled between two 18-hole golf courses and just minutes from Highway 407 and downtown Brooklin, enjoy the perfect blend of privacy and convenience. Inside, white oak hardwood floors, 12' ceilings with coffered designs, custom trim, and a modern open-concept kitchen with a walk-in pantry create a welcoming and stylish atmosphere. The fully sodded and irrigated lot, covered rear Loggia with BBQ gas line, and state-of-the-art mechanicals including zoned HVAC, central air, heated ensuite floors, and remote-controlled blinds ensure comfort and ease. Live your dream lifestyle with elegance and space to entertain in every corner. More details
    Listed by ROYAL LEPAGE SIGNATURE REALTY and ROYAL LEPAGE CONNECT REALTY
    LISTING DETAILS
    John Owen, Broker

  • 6540 Coronation Road in Whitby: Rural Whitby E12583930 - House

    6540 Coronation Road Rural Whitby Whitby L0B 1C0
    Main Photo: 6540 Coronation Road in Whitby: Rural Whitby E12583930 - House

    6540 Coronation Road Whitby L0B 1C0 Rural Whitby

    $3,499,999
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12583930
    Bedrooms:
    5
    Bathrooms:
    8
    Welcome to this brand new custom-built luxury home offering over 8,500 sq. ft. of elegant living space with top-of-the-line finishes throughout. The main floor features 12-ft ceilings, a spacious open-concept layout with a grand 24-ft open-to-above living room, a modern gourmet kitchen with high-end finishes, an office with an attached bath and closet, and large windows that fill the home with natural light. The second floor offers 10-ft ceilings, 4 generous bedrooms each with ensuite baths and walk-in closets, a large sitting area, a walkout to the balcony, and a convenient laundry room. The finished basement includes 10-ft ceilings, a stylish bar, media room, gym, and an additional bedroom with ensuite bath. Complete with a 3-car garage and parking for over 10 vehicles, this stunning home truly combines luxury, comfort, and modern design. More details
    Listed by KING REALTY INC.
    LISTING DETAILS
    John Owen, Broker

  • 28 Scott Street in Whitby: Blue Grass Meadows E12576808 - House

    28 Scott Street Blue Grass Meadows Whitby L1N 3L1
    Main Photo: 28 Scott Street in Whitby: Blue Grass Meadows E12576808 - House

    28 Scott Street Whitby L1N 3L1 Blue Grass Meadows

    $2,499,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12576808
    Bedrooms:
    6
    Bathrooms:
    6
    Luxury Custom Home in the Heart of Whitby! Experience refined living in this stunning custom-built home showcasing elegance, sophistication, and superior craftsmanship throughout. A grand foyer with 10-ft ceilings welcomes you into bright, open principal rooms filled with natural light. The gourmet kitchen features premium Jenn Air appliances, a large centre island, and seamless flow into the formal dining room and open-concept living area - perfect for entertaining in style. The primary suite offers a spa-inspired ensuite and spacious walk-in closet. Each additional bedroom includes its own ensuite, providing exceptional comfort and privacy. The fully finished lower level adds versatility with two extra bedrooms, a full bath, and a large recreation area - ideal for a home theatre, gym, games room, or in-law suite. Step outside to a beautifully landscaped backyard designed for summer entertaining, complete with areas for dining and relaxation. Located in one of Whitby's most prestigious neighbourhoods, close to top-rated schools, parks, and all essential amenities. A true showpiece for the discerning buyer! More details
    Listed by DREAM HOME REALTY INC.
    LISTING DETAILS
    John Owen, Broker

  • 50 Carnwith Drive W in Whitby: Brooklin E12559938 - House

    50 Carnwith Drive W Brooklin Whitby L1M 2N1
    Main Photo: 50 Carnwith Drive W in Whitby: Brooklin E12559938 - House

    50 Carnwith Drive W Whitby L1M 2N1 Brooklin

    $2,495,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12559938
    Bedrooms:
    4
    Bathrooms:
    6
    Backing onto a picturesque wooded ravine, this exceptional Fulton Homes "Flatbush" Elevation B sits on a rare 52x133 ft premium lot with a desirable walk-up basement-perfect for future in-law or multi-generational living. Offering approximately 4,220 sq ft of executive space + the fully finished basement, this home blends luxury craftsmanship with modern family functionality. The main & 2nd level feature stunning hardwood floors, an elegant staircase with wrought-iron spindles, a private main-floor office, and a mudroom with direct garage access. The gourmet kitchen impresses with a butler's pantry, walk-in pantry, top-of-the-line Jennair built-in appliances including gas range, upgraded cabinetry with gold hardware, pot filler, and quartz counters with a dramatic waterfall island. The spacious breakfast area offers a walk-out to a large deck with serene ravine views. The formal dining room, complete with a coffered ceiling, is ideal for entertaining, while the family room features a custom gas fireplace and abundant natural light. Upstairs, a skylight enhances the bright, open atmosphere. The large laundry room includes quartz counters and a walk-in linen closet. All four bedrooms offer ensuites and walk-in closets, providing comfort and privacy for the entire family. The primary retreat is a true standout, featuring his-and-hers walk-in closets, a vanity/coffee bar, and a spa-like 5-piece ensuite with heated floors, freestanding soaker tub, and glass rain shower. Fully finished walk-up basement offering exceptional versatility with a wet bar, great windows, cold cellar, and ample storage space-ideal for recreation or extended family living. Premium construction backed by Tarion warranty provides peace of mind and long-term value. Located within walking distance to parks, top-rated schools, and charming downtown Brooklin, with quick access to Hwy 407/418 for commuters, this luxurious ravine-lot residence is designed for the most discerning buyer! More details
    Listed by TANYA TIERNEY TEAM REALTY INC.
    LISTING DETAILS
    John Owen, Broker

  • 134 Front Street E in Whitby: Port Whitby E12504364 - House

    134 Front Street E Port Whitby Whitby L1N 1A1
    Main Photo: 134 Front Street E in Whitby: Port Whitby E12504364 - House

    134 Front Street E Whitby L1N 1A1 Port Whitby

    $2,399,898
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12504364
    Bedrooms:
    4
    Bathrooms:
    5
    Welcome to your dream home close to the lake - a place that celebrates individuality, community, and connection. Nestled just steps from Whitby's stunning waterfront, this spectacular 4-bedroom residence offers over 4,000 sq ft of thoughtfully designed space - where sophistication meets serenity. Wake up to peaceful river views and enjoy your morning coffee on the wraparound porch overlooking the park - an inviting space where friends gather, paddleboards launch, and sunsets linger. Inside, experience grand 11-ft ceilings, a beautiful two-way fireplace, and refined details like 8-ft doors, California shutters, and a custom waffle ceiling in the office - perfect for working or creating in style. The chef-inspired kitchen features Bosch appliances, quartz countertops, and a 6-burner gas stove - ideal for entertaining, hosting dinner parties, or simply living your best life. A main-floor bedroom with a 3-piece bath offers flexibility for guests or multigenerational living. Upstairs, your primary suite is a private retreat with a spa-like ensuite featuring heated floors and a Victoria + Albert soaker tub. Step out onto your private second-floor terrace or retreat to the above-garage loft - a peaceful, light-filled space perfect for a home studio, office, or meditation nook. The basement features a separate entrance with plumbing and electrical ready for a future suite - offering versatility for guests, creative space, or potential rental income. All this, in one of Whitby's most desirable lakeside communities - where nature, connection, and inclusivity thrive. Love where you live! More details
    Listed by RE/MAX HALLMARK FIRST GROUP REALTY LTD.
    LISTING DETAILS
    John Owen, Broker

  • 780 Garden Street in Whitby: Pringle Creek E12491464 - House

    780 Garden Street Pringle Creek Whitby L1N 8P2
    Main Photo: 780 Garden Street in Whitby: Pringle Creek E12491464 - House

    780 Garden Street Whitby L1N 8P2 Pringle Creek

    $2,199,990
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12491464
    Bedrooms:
    5
    Bathrooms:
    4
    Built in 1845, the distinguished Mayfield Residence is a landmark estate that has gracefully stood the test of centuries. Once home to esteemed politicians, this historic property now offers a rare and versatile opportunity, uniquely perched above the celebrated Mayfield Towns by Sakmet Developments. Set on over an acre of manicured grounds, the residence commands attention with timeless curb appeal that simply cannot be replicated. The architecture is both stately and inviting-an enduring reflection of heritage, elegance, and permanence. Inside, a flexible and grand floorplan adapts effortlessly to today's modern demands. With designated Mixed-Use zoning, the property is approved for all office uses and presents the potential for a daycare facility (speak to Listing Agent regarding daycare use). This rare zoning unlocks the opportunity to integrate professional life with the comforts of home, creating a seamless live/work environment with unparalleled character. A 1,100 sq. ft. Coach House complements the main residence, offering housing for three vehicles and abundant storage. The grounds further accommodate 11 exterior parking spaces, ensuring ample room for clientele, guests, or extended family. This is more than a property; it is a once-in-a-generation opportunity to acquire a piece of Whitby's history while embracing its extraordinary potential for the future. More details
    Listed by REAL BROKER ONTARIO LTD.
    LISTING DETAILS
    John Owen, Broker

  • 40 Endeavour Court in Whitby: Williamsburg E12487334 - House

    40 Endeavour Court Williamsburg Whitby L1P 0B5
    Main Photo: 40 Endeavour Court in Whitby: Williamsburg E12487334 - House

    40 Endeavour Court Whitby L1P 0B5 Williamsburg

    $2,375,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12487334
    Bedrooms:
    6
    Bathrooms:
    5
    Welcome to 40 Endeavour Court, a rare offering tucked at the end of a quiet court and bordered by ravine on two sides. This custom 5+1 bedroom, 5 bath home spans over 5,000 sq. ft. of finished living space and is designed for both everyday comfort and exceptional entertaining.Step inside to soaring ceilings, sun-filled rooms, and an open layout that flows seamlessly from the family room with gas fireplace to the chefs kitchen. The kitchen is a showpiece, featuring a 6-burner Thermador gas stove with pot filler, Thermador double ovens and fridge, Bosch dishwasher, wine fridge, large centre island, and walk-out to a heated covered deck with gas fireplaceperfect for year-round enjoyment.The primary suite offers sunset views, two walk-in closets, and a spa-like ensuite with Jacuzzi tub and multi-jet shower. Four additional bedrooms, each with ensuite or shared bath, provide abundant space for family and guests.The finished walk-out basement adds a second kitchen, 6th bedroom, 3-pc bath, gym, recreation room, and direct access to your own resort-style oasis. A sparkling inground pool, relaxing hot tub, and expansive multi-level deck are set against dramatic armour stone landscaping and mature trees. With hundreds of thousands invested, this backyard was created for unforgettable family gatherings and elegant entertaining. Additional highlights include a heated tandem garage (3 car) with interior access via custom mudroom, Hunter Douglas blinds, main floor office, and upper-level laundry. Located in coveted Williamsburg, steps to trails, parks, and four schools within walking distance, this is a true lifestyle home. Experience the best of all seasons swim all summer, watch the leaves change in fall from your hot tub, or cozy up by the outdoor fireplace in winter all surrounded by mature trees, ravine, and birdsong.40 Endeavour Court is more than a home its a retreat. More details
    Listed by RE/MAX HALLMARK FIRST GROUP REALTY LTD.
    LISTING DETAILS
    John Owen, Broker

  • 305 Trent Street W in Whitby: Downtown Whitby E12472978 - House

    305 Trent Street W Downtown Whitby Whitby L1N 1M3
    Main Photo: 305 Trent Street W in Whitby: Downtown Whitby E12472978 - House

    305 Trent Street W Whitby L1N 1M3 Downtown Whitby

    $2,299,900
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12472978
    Bedrooms:
    4
    Bathrooms:
    4
    Create your very own Downton Abbey and experience the perfect blend of historic charm and contemporary elegance. This remarkable residence showcases timeless character alongside modern finishings, inviting you to live your best life surrounded by beauty and sophistication.From the moment you enter, soaring grand ceilings on both the main and second floors set the tone for the home's stately presence. Original hardwood floors span the first two levels, preserving the rich charm of yesteryear, while tasteful décor and oversized rooms create an atmosphere of refined comfort.The beautifully appointed kitchen features travertine flooring, an inviting eat-in area, and a walkout to the backyard oasis. Enjoy quiet mornings or evening gatherings on the cozy wraparound porch with pot lights, or in the enclosed sunroom overlooking lush, English-inspired gardens and a tranquil babbling brook pond.Upstairs, each spacious bedroom offers walk-in closets and grand ceilings, while the large laundry room-with its own walkout to a deck-makes chores a pleasure. The deck connects to a private gym and 3-piece bath located above the heated garage.The third floor is your private master retreat-a true sanctuary featuring a wraparound walk-in closet with custom built-ins and a stunning ensuite. Relax in the claw-foot tub or steamer shower, warmed by the gentle glow of a Napoleon electric fireplace.The large heated loft garage includes hydro, a garage door opener with remotes, and access from both the backyard and laundry room.Outdoors, the property is an absolute haven. Set on a rare double lot, the backyard offers mature perennial gardens, two ponds, a serene fire pit area, and a new fence providing privacy and peace. Enjoy natural gas hookups for your BBQ and future outdoor fireplace-perfect for entertaining in every season. New Fencing installed Fall 2024. Survey on File 2023. Walking distance to Trafalgar Castle (Private School) and Henry St High. More details
    Listed by Royal LePage Our Neighbourhood Realty
    LISTING DETAILS
    John Owen, Broker
1-10/13
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Data was last updated December 13, 2025 at 10:15 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.