House for sale in Whitby homes over 2000000

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Whitby homes for sale above 2,000,000

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1-10/15

  • 33 North Street in Whitby: Brooklin E13214732 - House

    33 North Street Brooklin Whitby L1M 1C2
    Main Photo: 33 North Street in Whitby: Brooklin E13214732 - House

    33 North Street Whitby L1M 1C2 Brooklin

    $2,679,900
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13214732
    Bedrooms:
    6
    Bathrooms:
    5
    Welcome To 6,000+ Sq Ft Of Elegantly Finished Living Space. On A Premium 97 x 150ft Lot In One Of Brooklin's Most Sought-After Pockets. Custom Built By "Delta-Rae" In July 2020, This 4+2 Bedroom, 5 Bath Home Has Been Enhanced With Nearly Half A Million Dollars In Post-Build Upgrades - Every Dollar Spent With Purpose And Precision. Inside, The Soaring 21' Great Room Captivates With A Stunning Ceiling Treatment That Commands Attention The Moment You Enter. Wide Plank Hardwood, A Chef-Inspired Kitchen, Main Floor Office, Designer Lighting Throughout, Heated Floors In All Washrooms & Tiled Areas, And Electric Motorized Window Coverings Complete The Main Level Experience. The Primary Retreat Is A True Sanctuary - Featuring A Gorgeous Walk-In Closet With Custom Built-Ins And A Spa-Like Ensuite. The Fully Finished Basement (2021) Is An Entertainer's Dream - Expansive Rec Room, Dedicated Gym, Two Additional Bedrooms And A Sleek 3-Piece Bath - Perfect For Extended Family Or Guests. Step Outside To A Backyard That Genuinely Rivals Any Resort - A Complete Landscape Transformation (2022) Featuring Beautifully Established Trees, Lush Shrubs, Full Irrigation, A Large Saltwater Pool With Triple Fountain Feature, 9' Deep End, Bench Seating At Both Ends, Generous Entry Steps, Spillover Spa, Dedicated Equipment Area & Private Change Room Shed. The Built-In Outdoor Kitchen With Gas BBQ & Fridge Completes The Experience. The Garage Is In A League Of Its Own - Professionally Transformed By "Garage Interiors" Of Woodbridge (2021): Epoxy Floors, Wall Panels, Finished Ceiling, 20' Built-In Shelving, Counter, Deep Freezer, Car Lift & Industrial Gas Heater. Total Parking For 16 - 12-Car Driveway Plus 4-Car Garage. Stroll To Downtown Brooklin's Shops, Restaurants, Parks & More Via A Charming Pedestrian Path. Minutes To Hwy 407 & Top-Ranked Schools. No Sidewalk. You Won't Just Want To Live Here - You'll Never Want To Leave. More details
    Listed by RE/MAX Rouge River Realty Ltd.
    LISTING DETAILS
    John Owen, Broker

  • 39 Glengowan Street in Whitby: Taunton North E13198378 - House

    39 Glengowan Street Taunton North Whitby L1R 0K9
    Main Photo: 39 Glengowan Street in Whitby: Taunton North E13198378 - House

    39 Glengowan Street Whitby L1R 0K9 Taunton North

    $2,350,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13198378
    Bedrooms:
    5
    Bathrooms:
    5
    A striking expression of modern luxury, this architecturally refined residence offers over 3,517 sq. ft. above grade with a seamless blend of bespoke craftsmanship, designer finishes, and resort-inspired living.The impressive stone and stucco façade, framed by professional landscape lighting and manicured grounds, opens to interiors defined by soaring ceilings, oversized windows, expansive principal rooms, and exceptional architectural detail. Custom paneled feature walls painted in timeless Oxford White add depth and elegance throughout, while a dramatic lacquered black library creates a bold focal point that elevates the home's design narrative.The dining room showcases intricate waffle ceilings, extensive wall paneling, a stunning double-sided fireplace, and rich Fornasetti designer wallpaper, creating a space that feels both timeless and editorial in design.The chef-inspired kitchen features a premium Wolf gas range, high-end integrated refrigeration, Restoration Hardware lighting, generous prep space, and effortless flow into the dining and living areas. Towering rear windows flood the home with natural light while creating a seamless connection to the backyard retreat.A fully integrated Control4 system powers zoned audio, surround sound, and integrated speakers throughout the main level and outdoor living spaces.The fully finished lower level delivers a boutique wellness experience with a dedicated fitness area, spa-inspired sauna, additional living space, and beautifully appointed guest accommodations.Outside, the backyard rivals a private resort with expansive limestone hardscaping, ambient lighting, mature landscaping, custom surround sound, waterfall pool features, and a pergola lounge with integrated fire table.Sophisticated yet welcoming, every inch of this residence has been intentionally curated to deliver an extraordinary lifestyle experience. More details
    Listed by SUTTON GROUP-HERITAGE REALTY INC.
    LISTING DETAILS
    John Owen, Broker

  • 7925 Cedarbrook Trail in Whitby: Rural Whitby E13156428 - House

    7925 Cedarbrook Trail Rural Whitby Whitby L1M 1L9
    Main Photo: 7925 Cedarbrook Trail in Whitby: Rural Whitby E13156428 - House

    7925 Cedarbrook Trail Whitby L1M 1L9 Rural Whitby

    $2,875,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13156428
    Bedrooms:
    6
    Bathrooms:
    8
    Extraordinary French-inspired country estate set on approximately 10 private acres in Rural Whitby, just minutes to downtown Brooklin, Highways 412 & 407, offering the perfect blend of luxury country living and everyday convenience. This impressive residence offers approximately 8,000 sq. ft. of finished living space with 5+1 bedrooms, 8 bathrooms, a full in-law apartment ideal for extended family or income potential, and an expansive walk-out lower level designed for entertaining and multi-generational living. A standout feature of the property is the exceptional detached workshop offering approximately 4,400 sq. ft. across two levels (50' x 44'). Designed with functionality and versatility in mind, the shop features 12-foot ceilings on the main floor, oversized drive-in doors, 100-amp service, water service, excellent insulation for year-round use, and expansive open-concept space ideal for contractors, trades, car enthusiasts, hobbyists, entrepreneurs, storage, or recreational use. The grounds are equally spectacular, featuring Lynde Creek running through the property with a picturesque bridge leading to the barn and open green space beyond. Beautifully landscaped with breathtaking views in every direction, this rare estate property offers incredible privacy, versatility, and lifestyle appeal all within minutes of Brooklin and major commuter routes. More details
    Listed by Keller Williams Energy Real Estate
    LISTING DETAILS
    John Owen, Broker

  • 19 Wilson House Drive in Whitby: Rural Whitby E13139116 - House

    19 Wilson House Drive Rural Whitby Whitby L0B 1A0
    Main Photo: 19 Wilson House Drive in Whitby: Rural Whitby E13139116 - House

    19 Wilson House Drive Whitby L0B 1A0 Rural Whitby

    $2,499,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13139116
    Bedrooms:
    5
    Bathrooms:
    5
    An exceptional custom-built bungalow by Andelwood Homes, set within the prestigious Chateaus of Wilson House Drive in the quiet hamlet of Ashburn. Positioned on a beautifully landscaped 0.80-acre lot, this executive residence offers over 6,000 SF of finished living space, combining timeless craftsmanship, refined architectural detail, and rare bungalow living in one of Durham Region's most established estate communities. The main floor features 9-foot ceilings, stained red oak hardwood flooring, Carrara marble tile in the foyer, coffered ceilings, crystal chandeliers, and extensive custom millwork throughout. A bright, open-concept layout connects the kitchen, breakfast area, and family room, creating a natural flow for entertaining and everyday living. The chef's kitchen includes granite countertops and backsplash, professional-grade appliances including a 36-inch Wolf gas range, custom island with breakfast bar, built-in refrigerator, beverage centre, and French doors leading to the upper deck with gas BBQ hookup. The family room features a gas fireplace with marble surround and overlooks the private backyard through French-style windows. The main-floor primary retreat offers a comfortable seating area and a well-appointed ensuite. The professionally finished walk-out lower level expands the home's usable living space with 9-foot ceilings, large windows, an entertainment area with custom bar, additional bedrooms, and direct access to the interlock patio and garage. Ideal for hosting, extended family, guests, or multi-generational living. Additional features include a four-car garage, hard-wired gas generator, irrigation system, owned security system, upgraded mechanicals, and built-in surround sound, and a private landscaped setting. A rare opportunity to own a thoughtfully designed executive bungalow with estate-level scale, privacy, and craftsmanship. More details
    Listed by CENTURY 21 PERCY FULTON LTD.
    LISTING DETAILS
    John Owen, Broker

  • 47 Knightsbridge Court in Whitby: Pringle Creek E13067532 - House

    47 Knightsbridge Court Pringle Creek Whitby L1R 2T9
    Main Photo: 47 Knightsbridge Court in Whitby: Pringle Creek E13067532 - House

    47 Knightsbridge Court Whitby L1R 2T9 Pringle Creek

    $2,999,999
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13067532
    Bedrooms:
    7
    Bathrooms:
    5
    Experience the perfect harmony of sophisticated living and strategic opportunity. Nestled on an expansive, mature-treed lot in high-demand Pringle Creek, this beautifully renovated estate offers extreme privacy while keeping you 5 minutes from the 401, 407, and 412 corridor. Designed for the discerning homeowner, the interior features rich hardwood floors and sun-lavished spaces. The primary retreat is a true sanctuary, boasting a skylight-lit ensuite and a private sitting area. Start your mornings with ease as both the primary suite and the first bedroom offer direct access to a sprawling walk-out balcony. For the ultimate escape, the massive upper terrace serves as your private "staycation" destination. Beyond the luxury, this property is a functional powerhouse. The fully finished basement-complete with a separate entrance, master ensuite, and its own laundry-presents an incredible opportunity for a high-end rental, multi-generational living, or a professional home-based business. More details
    Listed by ROYAL LEPAGE REAL ESTATE SERVICES LTD.
    LISTING DETAILS
    John Owen, Broker

  • 105 Franklin Crescent in Whitby: Rural Whitby E13047934 - House

    105 Franklin Crescent Rural Whitby Whitby L0B 1A0
    Main Photo: 105 Franklin Crescent in Whitby: Rural Whitby E13047934 - House

    105 Franklin Crescent Whitby L0B 1A0 Rural Whitby

    $3,799,999
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13047934
    Bedrooms:
    6
    Bathrooms:
    6
    This Isn't Just A Home - It's A Lifestyle Upgrade. Wake Up Every Day Feeling Like You're On Vacation In This Show-Stopping Modern Estate Tucked Inside The Exclusive Lakeridge Links Estates Of Ashburn, Whitby. Set On Over 1.2 Private Acres, Surrounded By Golf Course Greens And Untouched Nature, This Is Where Luxury Meets Escape. Spanning Approximately 8,800 Sq. Ft Of Finished Living Space., This Owner-Built Masterpiece Was Crafted With Intention, Passion, And Uncompromising Standards. From The Upgraded Foundation With A Double Weeping System To The Flawless Finishes Throughout, This Home Was Built To Impress - And Built To Last. Sunlight Pours Through Soaring Ceilings And Wall-To-Wall Windows, Setting The Stage For Unforgettable Entertaining. The Chef'S Kitchen Anchors The Open-Concept Layout, Flowing Effortlessly To The Outdoors For Seamless Indoor-Outdoor Living. Every Space Feels Grand, Yet Warm. Elevated, Yet Inviting. Slip Away To Your Spa-Worthy Primary Retreat With Heated Floors And Dual Walk-Ins - Your Own Private Sanctuary After A Long Day. Downstairs, The Lower Level Delivers Serious Versatility With Full In-Law Or Nanny Suite Potential, Complete With A Kitchen, Rec Space, And Separate Walk-Up Entrance. Loaded With Smart Home Technology, A Four-Car Garage With EV Charging, And Premium Finishes In Every Corner, This Home Checks Every Box - And Then Some. Spend Weekends Apple Picking At Nature's Bounty Farm, Browsing Brooklin Farmers' Market, Unwinding At Thermea Spa, Or Carving Fresh Powder At Dagmar And LakeRidge Ski Resorts. With Highways 407 & 412 Just Minutes Away, Luxury Living Has Never Been So Effortless. Homes Like This Don't Come Around Often. Rare. Refined. Remarkable. Book Your Private Showing And Feel It For Yourself. More details
    Listed by REALTY WEALTH GROUP INC.
    LISTING DETAILS
    John Owen, Broker

  • 15 Shepherd Road in Whitby: Rural Whitby E13020368 - House

    15 Shepherd Road Rural Whitby Whitby L1M 1G8
    Main Photo: 15 Shepherd Road in Whitby: Rural Whitby E13020368 - House

    15 Shepherd Road Whitby L1M 1G8 Rural Whitby

    $2,647,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13020368
    Bedrooms:
    7
    Bathrooms:
    7
    Macedonian Village Opportunity - Bungalow Living on a Premium Conservation Lot, this custom-built bungalow offers exceptional space, privacy, and long-term versatility on a premium 102.48 ft x 352.51 ft lot backing onto the natural beauty of Heber Down Conservation Area.Designed for both everyday comfort and multi-generational living, the main level features four spacious bedrooms, each with its own en-suite and walk-in closet, along with 10-ft ceilings, new engineered hardwood flooring, and fresh paint throughout (2025). The great room impresses with a 16-ft cathedral ceiling and gas fireplace, while the updated kitchen showcases stainless steel appliances, waffle ceilings, crown moulding, and California shutters.The primary suite is a true retreat, complete with a custom ceiling, walk-in dressing room, and a 5-piece en-suite overlooking the private backyard and conservation setting.The finished walk-out basement adds outstanding flexibility with three additional bedrooms, a gym, two large recreation areas, a gas fireplace, and a rough-in kitchen ideal for extended family, in-law potential, or future customization.Additional highlights include a main-floor office, laundry room, central vacuum system, and an attached garage with workshop and 60 Amp service perfect for a hobby space, studio, or future golf simulator.Outdoors, enjoy a private backyard oasis with an in-ground pool featuring an updated liner, heater, and UV system (Aug 2025), along with interlocking landscaping and direct access to nature.With its timeless brick, stone, and stucco exterior, no rental items, and a highly sought-after location, this is a standout opportunity for buyers seeking space, privacy, and long-term value in one of Whitby's most exclusive communities. More details
    Listed by RE/MAX HALLMARK FIRST GROUP REALTY LTD.
    LISTING DETAILS
    John Owen, Broker

  • 10 Philips Road in Whitby: Rural Whitby E13020390 - House

    10 Philips Road Rural Whitby Whitby L1M 1G7
    Main Photo: 10 Philips Road in Whitby: Rural Whitby E13020390 - House

    10 Philips Road Whitby L1M 1G7 Rural Whitby

    $3,347,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13020390
    Bedrooms:
    5
    Bathrooms:
    5
    Luxury Estate Bungaloft in Macedonian Village | Brand New with Tarion Warranty. Welcome to 10 Phillips Road, a rare opportunity to own a brand-new custom bungaloft on a premium 125' x 278' estate lot in the prestigious community of Macedonian Village, Whitby. Surrounded by nature and just steps to Heber Down Conservation Area, this home offers the perfect blend of luxury, privacy, and everyday functionality-now positioned for today's market. Offering over 4,000 sq. ft. of above-grade space, this residence showcases exceptional craftsmanship and timeless design throughout. A grand 12-ft foyer welcomes you into an open-concept layout filled with natural light and expansive sightlines. The great room is a true focal point, featuring a dramatic 17-ft cathedral ceiling and a gas fireplace, perfect for both relaxing evenings and entertaining. The space flows seamlessly into a chef-inspired kitchen complete with Fisher & Paykel built-in appliances, quartz countertops, and a full-height quartz backsplash, as well as a formal dining area ideal for hosting. The main-floor primary suite delivers comfort and sophistication, highlighted by an 11-ft tray ceiling, a spacious walk-in dressing room with custom built-ins, and a spa-inspired 5-piece ensuite with a curbless glass shower and double vanity. Additional features include built-in speakers, a central vacuum, and premium finishes throughout. A third main-floor bedroom offers flexibility as a home office or guest space. Walkout Basement with Endless Potential. The unfinished walkout basement features oversized above-grade windows and is thoughtfully equipped with rough-ins for two 3-piece bathrooms and one 2-piece bathroom, along with a security system ready to be customized to suit your lifestyle. Set on a deep, private lot in one of Whitby's most exclusive enclaves, this home offers peaceful surroundings with convenient access to trails, parks, and nearby amenities. Tarion warranty included. Immediate occupancy available. More details
    Listed by RE/MAX HALLMARK FIRST GROUP REALTY LTD.
    LISTING DETAILS
    John Owen, Broker

  • 9285 Dagmar Road in Whitby: Rural Whitby E13001942 - House

    9285 Dagmar Road Rural Whitby Whitby L0B 1A0
    Main Photo: 9285 Dagmar Road in Whitby: Rural Whitby E13001942 - House

    9285 Dagmar Road Whitby L0B 1A0 Rural Whitby

    $2,199,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E13001942
    Bedrooms:
    3
    Bathrooms:
    2
    Picturesque, serene, and unassuming, 9285 Dagmar is a gorgeous, stunningly renovated, three bedroom bunglalow situated on 13 acres of beautiful, private land! Set back from the road with large hedges and an electronic gate separating you, this enviable home feels completely private. The large circular driveway has ample parking, plus an oversized two car garage and carport.The well proportioned, and open concept, living room, dining room, and kitchen are beautifully renovated with stunning details throughout, featuring: Custom millwork, built in cabinetry, a fabulous island in the kitchen, and a vaulted ceiling in the family room, complete with custom wainscotting. The herringbone white oak flooring, and carefully chosen paint colours, compliment the gorgeous stone surround of the wood burning fireplace.As you step through the front door and take two steps into the house, you have a straight line view through the back of the house to the breathtaking scenery behind. Beyond the back deck is a natural, spring fed, pond, charming rounded bridges to cross the water, ample grass to run and play in, and your own private forest.Situated just minutes from the 407, 412, and the 401, the city is easily accessible. In the immediate vicinity, there are several golf courses, ski resorts (Dagmar and Lake Ridge are only 3 minutes away!), parks with walking trails, and downtown Whitby is a short drive away. A truly special property! More details
    Listed by REAL BROKER ONTARIO LTD.
    LISTING DETAILS
    John Owen, Broker

  • 28 Scott Street in Whitby: Blue Grass Meadows E12967818 - House

    28 Scott Street Blue Grass Meadows Whitby L1N 3L1
    Main Photo: 28 Scott Street in Whitby: Blue Grass Meadows E12967818 - House

    28 Scott Street Whitby L1N 3L1 Blue Grass Meadows

    $2,399,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12967818
    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
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Data was last updated June 1, 2026 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.