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

Welcome to 82 Bridlewood Boulevard, a stunning custom-built Delta-Rae home where luxury, craftsmanship, and design come together seamlessly. Offering approximately 5,000 sq. ft. of finished living space, this exceptional 4+1 bedroom, 4.5 bathroom residence features white oak flooring throughout, a spectacular 16-foot Venetian plaster fireplace, and an award-winning Rocpal kitchen complete with Cambria Britannica Surfaces and fully panelled JennAir appliances. Designed with modern convenience in mind, the home is equipped with smart home technology, Somfy automated shades and drapery, and a professionally finished lower level. The resort-inspired backyard is an entertainer's dream, showcasing premium stonework, outdoor inlay lighting, a Rain Bird irrigation system, and an oversized saltwater pool surrounded by beautifully landscaped grounds. A truly rare offering and one of Whitby's finest luxury homes.

82 Bridlewood Boulevard, Whitby

Listing courtesy of RE/MAX Jazz INC..

$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

Listing courtesy of REVEL REALTY INC..

$2,199,000

5 Beds ⋅ 5 Baths ⋅ E13557216 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

Listing courtesy of SUTTON GROUP-HERITAGE REALTY INC..

$2,875,000

6 Beds ⋅ 8 Baths ⋅ E13537286 MLS® #

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. (id:5764)

7925 Cedarbrook Trail, Whitby

Listing courtesy of Keller Williams Energy Real Estate.

$2,875,000

6 Beds ⋅ 8 Baths ⋅ E13537286 MLS® #

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

Listing courtesy of Keller Williams Energy Real Estate.

$2,299,900

5 Beds ⋅ 4 Baths ⋅ E13519274 MLS® #

Amazing location! This exceptional custom home with over 5,000 sq ft of total living space features 4+1 bedrooms, 4 bathrooms, a finished in-law suite, and a detached 2-storey carriage house offering incredible flexibility. The natural stone exterior, cedar shake siding and roof, professionally landscaped grounds, stone walls, and gated entrance create outstanding curb appeal. Enjoy a private backyard oasis complete with irrigation, landscape lighting, a tranquil fountain, and a wood-burning outdoor fireplace. Inside, soaring and tray ceilings, crown moulding, custom wood paneling, solid wood doors, wood-framed windows, designer lighting, hardwood flooring, and a striking herringbone-tiled foyer showcase exceptional craftsmanship. The chef's kitchen features premium Sub-Zero, Wolf, and Cove appliances, marble countertops and backsplash, custom solid wood cabinetry with illuminated glass display cabinets, a large centre island, and a butler's pantry. French doors from the breakfast area open to the beautifully landscaped backyard. The living room features a wood-burning fireplace, while the dining room is perfect for entertaining. The luxurious primary suite offers designer lighting, a spa-inspired ensuite and large walk-in closet. An upper-level fitness room with a built-in sauna creates a private wellness retreat. The lower level includes an in-law suite with a bathroom, kitchenette, laundry, slate flooring and a wood-burning fireplace. The heated and air-conditioned carriage house features vaulted ceilings, a wood-burning fireplace, Saltillo tile, hardwood flooring, and custom wood staircases. Additional highlights include hardwired security with cameras, a full-home generator, multiple laundry areas, a cold room, and countless luxury upgrades. Located in a coveted historic downtown neighbourhood with mature, tree-lined streets, this home offers easy walking to restaurants, shops, and cafés. Ideal for commuters close to the GO Train and Highway 401.

505 King Street, Whitby

Listing courtesy of RE/MAX Rouge River Realty Ltd..

$2,450,000

5 Beds ⋅ 5 Baths ⋅ E13235390 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

Listing courtesy of Keller Williams Energy Real Estate.

$2,349,900

5 Beds ⋅ 5 Baths ⋅ E13139116 MLS® #

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. (id:5764)

19 Wilson House Drive, Whitby

Listing courtesy of CENTURY 21 PERCY FULTON LTD..

$2,349,900

5 Beds ⋅ 5 Baths ⋅ E13139116 MLS® #

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.

19 Wilson House Drive, Whitby

Listing courtesy of CENTURY 21 PERCY FULTON LTD..

$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

Listing courtesy of Royal LePage Frank Real Estate.

$2,647,000

7 Beds ⋅ 7 Baths ⋅ E13020368 MLS® #

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. (id:5764)

15 Shepherd Road, Whitby

Listing courtesy of Re/Max Hallmark First Group Realty Ltd..

$2,647,000

7 Beds ⋅ 7 Baths ⋅ E13020368 MLS® #

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.

15 Shepherd Road, Whitby

Listing courtesy of RE/MAX HALLMARK FIRST GROUP REALTY LTD..

$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

Listing courtesy of ROYAL HERITAGE REALTY LTD..

$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

Listing courtesy of ROYAL HERITAGE REALTY LTD..

$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

Listing courtesy of RE/MAX Jazz INC..

$2,199,000

6 Beds ⋅ 5 Baths ⋅ E11995895 MLS® #

Welcome to 65 Preservation Place. This 4,442 Sq. Ft Executive Home Sits On A 69x180 ft Lot Located In The Prestigious Williamsburg Community And Built By The Luxury Homebuilder, DeNoble Homes. The Home Features Over $500,000 Worth Of landscaping Including Inground Pool With Water Features And Slide, Hottub, Outdoor Kitchen, Gazebo And Forested Rear. Step Inside The Home To A Sprawling Atrium That Is So Inviting You Feel Like You Are At Home The Moment You Walk In. Large Living And Dining Room Welcomes Your Family With A 2-Way Floor To Ceiling Fireplace Centering The Rooms. Large Office For The Stay At Home Business Person. Chefs Kitchen With Stone Backsplash Feature, S/S Appliances Including Double Wolf Stove, Servery featuring Bar And Large Walk-in Pantry. The Two-Storey Family Room Is A Showpiece With Floor To Ceiling Built-Ins And Large Windows To View Your Resort Style Pool And Landscaping Outside. Upstairs Boasts A Massive Primary Bedroom With Sitting Area, Juliet Balcony Overlooking Family Room, Smooth Ceilings, Pot Lites And A 5 Piece Bath. A Second Primary Is Featured In This Home with A 4 pc Bath. Bedrooms 3&4 Share A Jack And Jill And Offer W/I Closets. The Professionally Finished Basement Provides For An Extra 1800 sq. ft Of Living Space And Includes Wet Bar, Living Room With Stone Fireplace, B/I Speakers, 2 More Bedrooms, Exercise Room And Games Room. The Perfect Home For A Large Family. This Home Offers A 3 Car Garage With High Ceilings. It Is rare To Find Homes For Sale On This Quiet Cul de Sac And This Property Is One Of The Largest And Most Luxurious. No Need To Escape In The Summer, When Your Vacation Is In Your Own Backyard. Steps To Thermea Spa, Big Box Stores, Transit And Hwy 407.

65 Preservation Place, Whitby

Listing courtesy of GET SOLD REALTY INC..

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

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