Whitby Real Estate | Whitby Properties between $2,000,000 and $3,000,000 for Sale

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.

7925 Cedarbrook Trail, Whitby

$2,100,000

5 Beds ⋅ 5 Baths ⋅ E13659920 MLS

Welcome to an exceptional custom-built bungalow by Andelwood Homes, set within the prestigious Chateaus of Wilson House Drive in the quiet hamlet of Ashburn. Situated on a beautifully landscaped 0.80-acre lot, this impressive residence offers over 6,000 SF of finished living space, a 4-car garage, and a rare combination of space, privacy, craftsmanship, and versatile multi-generational living. The expansive main level features 9-ft ceilings, stained red oak hardwood flooring, Carrara marble tile, coffered ceilings, crystal chandeliers, and extensive custom millwork. At the heart of the home, the open-concept kitchen, breakfast area, and family room provide an ideal setting for everyday living and entertaining. The chef's kitchen features granite countertops and backsplash, a 36" Wolf gas range, professional-grade appliances, custom island with breakfast bar, built-in refrigerator, beverage centre, and French doors opening to the upper deck with gas BBQ hookup. The family room is highlighted by a marble-surround gas fireplace and French-style windows overlooking the private grounds. The main floor primary retreat offers a spacious sitting area and well-appointed ensuite, while additional bedrooms provide flexibility for family, guests, or home offices. The professionally finished walk-out lower level offers 9-ft ceilings, large windows, additional bedrooms, an expansive recreation and entertainment area with custom bar, and direct access to the interlock patio and garage-ideal for extended family or multi-generational living. Additional features include a hard-wired gas generator, irrigation system, owned security system, upgraded mechanicals, built-in surround sound, extensive parking, and beautifully maintained grounds. A rare estate bungalow offering exceptional scale and versatility in one of Durham Region's established estate communities.

19 Wilson House Drive, Whitby

$2,289,900

4 Beds ⋅ 4 Baths ⋅ E13644832 MLS

Views of the park-like 10+ acre lot from every room of this updated family home in picturesque Ashburn! Enjoy the tranquil, private setting just minutes from Brooklin's amenities. Relax and entertain in the beautiful family room, featuring a soaring cathedral ceiling, floor-to-ceiling stone fireplace, and an open flow to the family-sized kitchen.The contemporary, practical layout lets each room suit your individual needs: the formal dining room (currently used as an office) walks out to a wrap-around porch with a finished ceiling. Glass doors offer privacy without sacrificing views or light.The 2nd floor features 4 bedrooms and updated bathrooms. The partially finished basement offers a separate entrance from the oversized 2-car garage, high ceilings, 2 large cold cellars, a partially finished 2-piece bath, and a finished rec room with an above-grade window. Move right in - this home is freshly painted, well-maintained, has plenty of parking and storage, and is pet and smoke free!Recent updates include: windows (2022), eaves and fascia (2020), porch ceiling (2025), new trim and interior doors, new toilets, updated 2nd-floor bathrooms, and new broadloom and hardwood flooring. Septic pumped out August 2026.

365 Townline Road W, Whitby

$2,099,900

5 Beds ⋅ 5 Baths ⋅ E13639882 MLS

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 facade, 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.

39 Glengowan Street, Whitby

$2,450,000

5 Beds ⋅ 5 Baths ⋅ E13633596 MLS

Rarely offered in the prestigious Chateaus of Woodington, this exceptional custom-built "Royale" model is perfectly positioned on one of the area's most sought-after family-friendly courts, just steps from protected treed space and walking paths for an unmatched sense of privacy and tranquility. Set on a premium 60 x 123 ft lot, this extensively updated executive residence offers approximately 3,713 sq ft above grade plus a professionally finished lower level, delivering over 5200 sq ft of luxurious finished living space. Thoughtfully designed with timeless architecture and refined finishes throughout, the home features 10-ft ceilings on the main floor, 9-ft ceilings on the upper and lower levels, oversized principal rooms, and a seamless blend of elegance and functionality. The heart of the home is the beautifully updated chef-inspired kitchen featuring quartz countertops, custom backsplash, a Wolf gas range, premium finishes, and an open-concept design ideal for both everyday living and entertaining. Freshly painted throughout with updated lighting and beautifully renovated bathrooms, every detail has been carefully curated to offer a sophisticated, move-in ready luxury experience. Offering 5 bedrooms and 5 bathrooms, this home is designed to accommodate growing families and multi-generational living with ease. The professionally finished lower level is an entertainer's dream, complete with a wine cellar, hobby room, spacious great room with wet bar, gym/workout area, and a spa-inspired washroom featuring heated floors and a steam shower. Step outside to your private backyard oasis surrounded by mature trees and extensive landscaping, featuring a natural stone patio and exceptional outdoor living spaces designed for relaxation and entertaining. An extraordinary opportunity to own a turnkey luxury residence in one of the area's most exclusive and tightly held enclaves.

7 Woodington Court, Whitby

$2,850,000

6 Beds ⋅ 5 Baths ⋅ E13632490 MLS

Beautifully situated in Whitby's sought-after Blue Grass Meadows community, this brand-new custom home by award-winning builder, Desousa Homes Inc. offers exceptional craftsmanship and modern luxury throughout featuring close to 4,000 sq ft of living space. Set on an impressive 85' x 190' mature lot, the property features a long driveway with parking for up to eight vehicles and unobstructed west-facing views reaching all the way to Downtown Toronto on clear days. The main and second floors showcase white oak engineered hardwood, custom cabinety, a thoughtfully designed mudroom off the garage, five well-appointed bedrooms, four bathrooms, with a second floor dedicated laundry room and a stunning custom kitchen open to a large living area and spacious dining room. The Muskoka room offers year-round enjoyment overlooking the mature backyard. The home is fully landscaped with an irrigation system and the home is equipped with networking cable throughout including a camera system. A legal accessory apartment with its own ground-level entrance or integrated access from the main home provides outstanding flexibility. This bright, spacious suite includes large windows, luxury vinyl plank flooring, a full kitchen, generous bedroom, spa-inspired bathroom, independent heating controls, heat pump, separate hydro meter and HRV. Ideal as a private unit or seamless extension of the main home. Built with energy efficiency in mind, the home features spray foam insulation, dual HRV systems a heat pump for the ADU and a furnace, & A/C for main and second floors. Tarion New Home Warranty included. A truly one-of-a-kind residence in a mature, highly desirable neighbourhood. Experience luxury living at 153 Elizabeth Crescent.*Taxes not yet assessed on new build. Price is inclusive of HST.

153 Elizabeth Crescent N, Whitby

$2,259,900

5 Beds ⋅ 5 Baths ⋅ E13610930 MLS

Welcome to 51 Gloria Cres, a custom-built bungalow on a 39 x 184 ft lot in the prestigious Williamsburg community. Step inside and feel at home right away. Featuring hardwood floors throughout, this inviting home offers a spacious open-concept layout with a granite kitchen, eat-in area, and great room perfect for family living. Built-in speakers add extra comfort and charm. The main level features two large bedrooms, including a primary suite with a walk-in closet and ensuite with jacuzzi tub. Also included are a large office, powder room, and laundry room with access to the two-car garage with high ceilings. The great room walks out to a large deck with a gas line for your BBQ or smoker. The walkout lower-level features two large bedrooms both with ensuites, exercise space, and a spacious open-concept living area with a kitchenette. It is rare to find a home like this For Sale on a quiet crescent. Just steps to amenities, schools, parks, Thermea Spa, big box stores, transit, and Highways 412, 407, and 401. Do not miss this rare opportunity to own an exceptional bungalow in Williamsburg. This is a must-see home!

51 Gloria Crescent, Whitby

$2,650,000

E13559128 MLS

**Turnkey Opportunity: Highly Profitable Established Multi-Division Food and Hospitality Company for Sale**Confidential opportunity to acquire 100% of an established operating corporation with three complementary business divisions: a full-service licensed restaurant, a dedicated commercial kitchen and private event space, and an established catering operation.The company benefits from multiple revenue streams, a loyal base of repeat private, corporate and institutional clientele, and confirmed future bookings. The operation includes an extensive inventory of commercial-grade restaurant, kitchen, catering and event equipment, including equipment and improvements added during the current ownership. Together, the divisions provide an integrated operating platform with established clientele, infrastructure and revenue-generating capacity.The business is cash-flow positive and is being offered as a corporate share sale, subject to the final structure agreed upon by the parties and their respective legal and accounting advisors.The existing liquor sales licence forms part of the current operation. Any continued use or transfer following a sale is subject to applicable AGCO requirements and approval. Perfect for an experienced restauranteur or expanding hospitality group looking for a premium opportunity.

Whitby

$2,100,000

E13041390 MLS

This property has been under the same meticulous ownership for over 50 years. Very clean, well-maintained 8-unit brick & block apartment building located in one of Whitby's most sought-after rental locations. All 2 bedroom units. Long history of stable rents and high occupancy. Rental upside offers the opportunity to increase yield and maximize return on investment. Ample on-site parking. Laundry room in building with coin-operated machines for additional income. The building has benefited from many recent updates, ensuring a turnkey acquisition for the next investor. Properties of this calibre with deep-rooted history and an excellent maintenance record are rarely available on the market.

300 Athol Street, Whitby

$2,950,000

4 Beds ⋅ 3 Baths ⋅ E12915192 MLS

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.

680 Winchester Road W, Whitby

$2,179,000

E12901988 MLS

Calling all developers, builders, and investors! PREMIUM DEVELOPMENT SITE! Buttoned down and permit ready to be built on. All lots are completely ready to be built on. All costs of development are paid for and included in the purchase price. Note: Completely serviced to the lot line. 4 Semi-Detached Bungalows with full walk outs to supersized backyard. Creatively inspired for a single family home and/or with fully legal basement apartment. Located in the downtown core of Whitby these extra deep lots are truly a rare find. All the parcels back onto and overlook Peel Park - Tennis courts, baseball diamond, soccer field etc. Situated in a highly desirable, family-friendly neighbourhood, this location offers close proximity to schools, parks, and convenient access to Highways 401, 412, and 407, as well as public transit. Walking distance to all amenities, restaurants, shopping & more!

805-807 Athol Street, Whitby

$2,179,000

E12901986 MLS

Calling all developers, builders, and investors! PREMIUM DEVELOPMENT SITE! Buttoned down and permit ready to be built on. All lots are completely ready to be built on. All costs of development are paid for and included in the purchase price. Note: Completely serviced to the lot line. 4 Semi-Detached Bungalows with full walk outs to supersized backyard. Creatively inspired for a single family home and/or with fully legal basement apartment. Located in the downtown core of Whitby these extra deep lots are truly a rare find. All the parcels back onto and overlook Peel Park - Tennis courts, baseball diamond, soccer field etc. Situated in a highly desirable, family-friendly neighbourhood, this location offers close proximity to schools, parks, and convenient access to Highways 401, 412, and 407, as well as public transit. Walking distance to all amenities, restaurants, shopping & more!

805-807 Athol Street, Whitby

$2,500,000

E12491398 MLS

Ready to move your medical business to your own medical building? 1533 Dundas St E in Whitby is the location you want to be. This building was completely renovated for medical uses in 2019, with modern design and excellent flow. Approximately 1550 sqft per floor. Lots of onsite parking for clients and staff. There is another medical tenant to assume on lower level providing some additional income. Why rent when you can own your own space. Location is perfect on busy 4 lanes for Dundas Street E (Highway 2) just west of Thickson Road and five minutes north of Highway 401. Do not delay in booking a showing for this fantastic property.

1533 Dundas Street E, Whitby

Whitby Properties between $2,000,000 and $3,000,000 for Sale

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