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

  • 305 Trent Street W in Whitby: Downtown Whitby E12931920 - House

    305 Trent Street W Downtown Whitby Whitby L1N 1M3
    Main Photo: 305 Trent Street W in Whitby: Downtown Whitby E12931920 - House

    305 Trent Street W Whitby L1N 1M3 Downtown Whitby

    $2,199,900
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12931920
    Bedrooms:
    5
    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 decor 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, corner gas fireplace, and a stunning en-suite. 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 openers 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

  • 680 Winchester Road W in Whitby: Rural Whitby E12915192 - House

    680 Winchester Road W Rural Whitby Whitby L1M 1V2
    Main Photo: 680 Winchester Road W in Whitby: Rural Whitby E12915192 - House

    680 Winchester Road W Whitby L1M 1V2 Rural Whitby

    $3,250,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12915192
    Bedrooms:
    4
    Bathrooms:
    3
    Location/Location/Location. At the crossroads of Country Lane and Highway 7, this stunning 11.82 acre farm offers a ready-to-move-in house or the perfect place to build your dream home or Home-based businesses or secondary suites (Buyer to do own due diligence). In Whitby's Calm Countryside, Adjacent To Hwy 412, 407. Whitby's Brooklin neighborhood is five minutes away. This charming home offers a blend of historical elegance, modern comfort and featuring ceilings that are about 9 feet high. Enjoy The Luxurious 5-Piece Bathroom With A Deep Soak Tub And Generous Shower Upstairs. Add appeal to the home with a hardwood floor. Enjoy the tranquil surroundings by stepping outside onto the spacious second-floor terrace. Custom maple cabinets, premium stainless steel appliances, and sophisticated granite countertops make the kitchen a chef's dream come true. Enjoy The Coziness Of The Kitchen's And Bathroom's Heated Flooring. This property is truly a slice of paradise, offering excellent potential for future development and being close to all amenities. More details
    Listed by RIGHT AT HOME REALTY
    LISTING DETAILS
    John Owen, Broker

  • 9640 Dagmar Road in Whitby: Rural Whitby E12887028 - House

    9640 Dagmar Road Rural Whitby Whitby L0B 1A0
    Main Photo: 9640 Dagmar Road in Whitby: Rural Whitby E12887028 - House

    9640 Dagmar Road Whitby L0B 1A0 Rural Whitby

    $2,200,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12887028
    Bedrooms:
    3
    Bathrooms:
    2
    Private 10-Acre Whitby Retreat - Bungalow with Walkout Basement, Workshop Garage & Space for Family, Business or Hobby Living! Rare opportunity to enjoy country living on 10 acres in Rural Whitby, just minutes from Brooklin and major highways. This 3-bedroom, 2-bathroom detached bungalow with walkout basement offers bright living spaces, hardwood floors, and large windows overlooking the surrounding landscape.The main floor features an eat-in kitchen, formal dining area, and a spacious primary retreat with private balcony, walk-in closet, and 5-piece ensuite with soaker tub and separate shower.The walkout basement offers excellent potential for an in-law suite or multigenerational living, while the detached three-door garage/workshop and extensive parking provide incredible flexibility for entrepreneurs, tradespeople, hobbyists, or vehicle storage.Enjoy the freedom of approx. 10 acres with space for recreation, gardens, hobby farming, or simply peaceful country living, all within a short drive to Whitby amenities, schools, shopping, and Highways 407 & 412 for easy commuting. More details
    Listed by LPT Realty
    LISTING DETAILS
    John Owen, Broker

  • 40 Endeavour Court in Whitby: Williamsburg E12833060 - House

    40 Endeavour Court Williamsburg Whitby L1P 0B5
    Main Photo: 40 Endeavour Court in Whitby: Williamsburg E12833060 - House

    40 Endeavour Court Whitby L1P 0B5 Williamsburg

    $2,275,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12833060
    Bedrooms:
    6
    Bathrooms:
    5
    Welcome to 40 Endeavour Court - a private ravine sanctuary tucked at the end of a quiet Williamsburg court. Bordered by mature trees and ravine on two sides, this custom 5+1 bedroom home offers approximately 3,680 sq. ft. above grade and over 5,000 sq. ft. of finished living space designed for executive living and multigenerational flexibility. Soaring ceilings and expansive windows fill the home with natural light. The family room with gas fireplace flows into a chef-inspired kitchen featuring a 6-burner Thermador gas range with pot filler, Thermador double ovens and fridge, Bosch dishwasher, wine fridge, and a large centre island built for gathering. Walk out to the heated covered deck with outdoor gas fireplace for seamless year-round enjoyment. The primary retreat offers sunset views, two walk-in closets, and a spa-like ensuite with Jacuzzi tub and multi-jet shower. Four additional bedrooms provide ensuite or shared bath access, ideal for growing families.The finished walk-out lower level includes a second kitchen, 6th bedroom, 3-piece bath, gym, recreation space, and direct access to the backyard oasis - perfectly suited for extended family or guests.Outdoors, enjoy a heated saltwater pool, hot tub, multi-level decking, armour stone landscaping, and exceptional privacy. Additional features include a heated tandem 3-car garage, custom mudroom, main floor office, upper-level laundry, and Hunter Douglas blinds. Steps to trails, parks, and four schools within walking distance, this is a rare opportunity to secure space, privacy, and lifestyle in one of Whitby's most desirable communities.40 Endeavour Court is more than a home - it's a retreat. More details
    Listed by RE/MAX HALLMARK FIRST GROUP REALTY LTD.
    LISTING DETAILS
    John Owen, Broker

  • 33 North Street in Whitby: Brooklin E12835010 - House

    33 North Street Brooklin Whitby L1M 1C2
    Main Photo: 33 North Street in Whitby: Brooklin E12835010 - House

    33 North Street Whitby L1M 1C2 Brooklin

    $3,280,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12835010
    Bedrooms:
    6
    Bathrooms:
    5
    Refined Elegance Defined By Curated Craftsmanship Encompassing Over 5000 Square Feet Finished On 95' Footage Corner Lot In Brooklin's Most Desirable Enclave - 4 Plus 2 Bed, 5 Bath Fully Custom Masterpiece Completed By Renowned "Delta-Rae" In 2020 Features Wide Plank Hardwood, Main Floor Office, Gourmet Chef's Kitchen And 21' Ceiling Great Room; Walking Out To Professionally Landscaped, Fully Fenced Backyard - Enjoy Resort Style Amenities From The Comfort Of Your Own Home With A Salt Water Pool, Spill Over Spa, Outdoor Kitchen Features B/I Gas Bbq And Fridge. Enjoy Mature Muskoka Like Trees For Ultimate Privacy. Impressive Primary WOW's With Expansive Walk-In And Bright Ensuite. Fully Finished Basement And Finished Gym Space. 4 Car Garage (3+Lift) Amplifies Functionality With "Garage Living" B/I Storage, Freezer, Purposeful Wall Trim And Epoxy Floor Finish. Walk To Downtown Brooklin In Minutes - Confluences Modern Conveniences With Small Town Feel. Walk To Downtown Through Quaint Unique Pedestrian Path To Bars, Ice Creamery, Restaurants, Parks, Longo's And So Much More. 3 Minutes To 407. Highly Ranked Elementary And Secondary Schools. No Sidewalk! Welcome Home!!! More details
    Listed by REMAX YOUR COMMUNITY REALTY
    LISTING DETAILS
    John Owen, Broker

  • 5785 Halls Road N in Whitby: Rural Whitby E12819660 - House

    5785 Halls Road N Rural Whitby Whitby L1M 1S5
    Main Photo: 5785 Halls Road N in Whitby: Rural Whitby E12819660 - House

    5785 Halls Road N Whitby L1M 1S5 Rural Whitby

    $3,949,999
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12819660
    Bedrooms:
    7
    Bathrooms:
    8
    Power of Sale (mortgage foreclosure) opportunity with financing available. The vendor is willing to provide a first mortgage loan of up to $2,000,000 at a competitive interest rate, offering a rare and flexible financing opportunity for qualified buyers. Built only 10 years ago, this custom 7 bedroom, 8 bathroom estate is privately set behind gates on a serene premium 6+ acre lot. Designed for tranquility, security, and privacy, the fully fenced property features a scenic natural water feature and expansive sports court, creating a resort-style atmosphere.The heart of the home is an impressive open-concept kitchen anchored by a stunning 25-foot quartz centre island with abundant seating, complete with a Wolf gas stove, dual Sub-Zero refrigerators, two Miele built-in ovens, under-cabinet lighting, and premium finishes throughout. The kitchen flows seamlessly into the family and dining areas with walkout access to the backyard patio overlooking the scenic grounds.A separate formal living room opens onto a balcony spanning the front of the home. The main floor also offers a private in-law suite with coffee bar, two bedrooms, 3-piece bath, and a dedicated office. Upstairs features five generously sized bedrooms, each with its own ensuite, plus a convenient second-floor laundry room.The primary suite includes a walk-in closet with custom shelving and a spa-inspired 5-piece ensuite with steam shower, fireplace, and Juliette balcony. The fully finished basement features radiant heated floors. Additional highlights include geothermal heating, gated and fenced grounds, a 5-car garage, and custom motorized blinds with individual remotes. A rare opportunity to own a private estate with flexible vendor financing in place. More details
    Listed by NEW ERA REAL ESTATE
    LISTING DETAILS
    John Owen, Broker

  • 134 Front Street E in Whitby: Port Whitby E12821054 - House

    134 Front Street E Port Whitby Whitby L1N 1A1
    Main Photo: 134 Front Street E in Whitby: Port Whitby E12821054 - House

    134 Front Street E Whitby L1N 1A1 Port Whitby

    $2,299,898
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12821054
    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, paddle boards 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

  • 59 Queen Street in Whitby: Brooklin E12795526 - House

    59 Queen Street Brooklin Whitby L1M 1C4
    Main Photo: 59 Queen Street in Whitby: Brooklin E12795526 - House

    59 Queen Street Whitby L1M 1C4 Brooklin

    $2,045,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12795526
    Bedrooms:
    5
    Bathrooms:
    4
    Custom-built Corvinelli bungalow featuring over 4400+ sqft of finished living space blending comfort, thoughtful design and unmatched quality.Nestled on a generous lot with mature trees this home offers a private retreat with modern luxuries. Exquisite craftsmanship is evident with high-quality upgraded casings, headers, 96" high by 13/4" thick solid doors on main floor and 80" high by 13/4" thick solid doors in basement & taller baseboards throughout.Crown moulding, 9' smooth ceilings, 5" vintage hickory hardwood enhances the warmth and sophistication of the main floor. Open concept living room with custom built-in flows into the family size eat-in kitchen with maple cabinetry, granite counters and honed travertine flooring flowing seamlessly into the butlers pantry with bar fridge, freezer and prep sink offering added convenience and style. Main floor laundry with granite counters, wall-to-wall uppers, under-mount sink and convenient garage access. Primary is a true retreat with a sophisticated tray ceiling, walk-out to covered patio, 5-piece ensuite with heated floors, deep soaker tub, glass shower w/hand held, 4 jets & rain shower, double vanity and spacious walk-in offering ample storage and a touch of luxury. Oak staircase with upgraded railing and wrought iron pickets lead to the expansive lower level with premium 7" Torlys cork flooring, spacious recreation room anchored by a dramatic floor-to-ceiling stone gas fireplace and wet bar featuring leathered granite, fridge and dishwasher. A dedicated gym area provides space for wellness and theatre room is complete with a gas fireplace offering a truly immersive cinematic experience. Lower level also includes two generously sized bedrooms, luxurious 4-piece bath with heated floors, cold cellar and ample storage. Second staircase provides convenient access to the exterior and oversized garage. From high-end finishes to its functional layout and peaceful setting this custom built home is a true oasis and rare find! More details
    Listed by THE NOOK REALTY INC.
    LISTING DETAILS
    John Owen, Broker

  • 535 Myrtle Road W in Whitby: Rural Whitby E12702842 - House

    535 Myrtle Road W Rural Whitby Whitby L0B 1A0
    Main Photo: 535 Myrtle Road W in Whitby: Rural Whitby E12702842 - House

    535 Myrtle Road W Whitby L0B 1A0 Rural Whitby

    $2,500,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12702842
    Bedrooms:
    4
    Bathrooms:
    2
    Welcome to Stone Eden-a place where timeless character and intentional living come together.Set on 10.87 rolling acres in the quiet countryside of Ashburn in Whitby, this remarkable property and home is a legacy meant to be lived in and cherished.From the moment you pass through the custom wrought-iron gate, a sense of calm settles in. The winding private drive leads you past two serene ponds, a mature apple orchard, and a heated in-ground pool, each element adding to the estate's rare privacy and natural beauty. A 37' x 28' barn enhances the possibilities-ideal for equestrian use, a hobby farm, creative workspace, or flexible storage.At the centre of the property stands the original hand-crafted stone residence, meticulously restored and updated to honour its heritage while offering modern comfort. Sunlight fills the inviting living and dining rooms, where warm hardwood floors and a gas fireplace set the tone for family gatherings and quiet evenings. The kitchen blends charm with functionality, featuring built-in appliances, a gas cooktop, and heated floors.The main floor also includes a sophisticated office with custom built-ins, perfect for focused work or study. Upstairs, four well-appointed bedrooms provide space and flexibility for families, guests, or multi-generational living. The finished walk-up basement adds yet another dimension, offering a stylish bar, gas fireplace, and a spacious area for relaxing or entertaining. Every detail of Stone Eden reflects pride of ownership-from the cedar roof (2020) and MagicWindows to the curated gardens and thoughtfully maintained trails. This is a property where history is preserved, nature is celebrated, and future memories are waiting to be made.Whether you're seeking a peaceful retreat, a multi-generational haven, or a place to fully embrace country living without compromise, Stone Eden invites you in. A truly rare and extraordinary opportunity. More details
    Listed by RE/MAX HALLMARK FIRST GROUP REALTY LTD.
    LISTING DETAILS
    John Owen, Broker

  • 9695 Duffs Road in Whitby: Rural Whitby E12692276 - House

    9695 Duffs Road Rural Whitby Whitby L0B 1A0
    Main Photo: 9695 Duffs Road in Whitby: Rural Whitby E12692276 - House

    9695 Duffs Road Whitby L0B 1A0 Rural Whitby

    $2,500,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12692276
    Bedrooms:
    7
    Bathrooms:
    5
    Amazing Opportunity 4 the Right Buyer Unique, Custom Log Home North of Brooklin 40+ acres of Beautiful Country Property Share incredible sunsets w/ family & friends splashing in the IG pool or w/a glass of Wine or Cappuccino on 1 of the many patios or decks Pass the stone gates & follow the driveway meandering to the Main Hse & 3 car garage Indoor/outdoor prkng for 20+ vehicles Tons of space 4 toys or eqpmnt Enter the Main Hse 2b greeted by impressive exposed Log Beams, solid natural wood & quality finishes Spend holidays, long wknds or life's celebrations w/ loved 1's & fill your cup on a regular basis in a warm & inviting atmosphere Prep meals in the custom kitchen & you are bathed in natural light thru a myriad of windows & sliding glass WO's The Great RM w/ sliding glass WO & LG windows continues bringing nature inside, 2 other formal rms on the MF provide family w/ lots of options The 2nd floor has 4 bdrms & 3 bthms Primary w/ LG windows allows you to view sunsets cozied up, under the cathedral ceiling w/ exposed beams A fabulous 5pc ensuite, soaker tub, dual vanity w/ Live Edge counter & heated flooring Bdrm 2 is equipped w/ a 4pc bth & WI closet Bdrm 3 & 4 offer numerous closets & cute Dormer windows There is a 5 th bdrm in the bsmnt & a 3pc bth Heading to the heated 3 car garage there is a new 2 bdrm accessory apartment above, It is a must see, remarkable panelled cathedral ceilings w/ exposed beams, an open concept Great RM & kitchen a luxurious bthrm & laundry closet The property also features a 14x26 Garden Shed a 60x40 Barn/Workshop w/ Oversized Drs The Owner has installed 2, 50 amp RV parking plots w/ septic A GeoThermal closed loop HVAC system, Generac back-up electrical system, Rolling Hills & a 34 Acres Hay Field provide the property w/ tons of options 4 the future. Walking & Bike trails cut through the small wooded section on the North side of the property What an incredible opportunity to create future memories w/ your Family. More details
    Listed by RE/MAX WEST REALTY INC.
    LISTING DETAILS
    John Owen, Broker
1-10/13
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Data was last updated March 29, 2026 at 04:15 AM (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.