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13 Most Expensive Luxury Homes in Ontario

The most expensive house in Canada isn’t in Vancouver. It isn’t even in Toronto. It’s on the outskirts of Calgary:

Most Expensive Home in Canada

Most Expensive Home in Canada

Property values are going up in the ultra-luxury market. Of the 20 Most Expensive Homes In The World owned by members of the Forbes Billionaires List, only six were priced at less than $100 million. Several either traded hands or boast an assessed value of more than twice that figure. The least expensive of these ultra-pricey homes traded hands for $88 million.

For the first time in a long time, the most expensive house in Canada isn’t in Vancouver. It isn’t even in Toronto. It’s on the outskirts of Calgary, a sure sign that the long-running oil boom has added the Alberta city to the list of Canadian markets with outrageous prices. A $37.8-million property once belonged to Ford family (the car, not the major).

Luxury Homes in Ontario:

The following is the list of 13 of Ontario’s most expensive properties, and the prices are as unique as the homes.

#13.) 163 Chartwell Road, Oakville

Price: $11,388,000.00

Approximately 14,700 sq. ft. of elegantly finished living space, on a full 1.15-acre lot on one of south-east Oakville’s most exclusive streets.

163 Chartwell Road , Oakville

163 Chartwell Road, Oakville

Entertainer’s delight, grand kitchen plus a summer kitchen & a servery; a handsome wine room accents the dining room; the great room boasts a soaring ceiling, 2-storey wood burning fireplace & wet bar.

163 Chartwell Road Back

Back Yard

5,121 sq. ft. in the lower level houses a soundproofed theatre, games & rec rooms, wet bar, gym, bedroom & walk-out. All of that on the 334′ deep lot with its infinity pool, hot tub, cabana with bar and a terrace with a fireplace & retractable screens.

Granite exterior, copper topped portico & lush landscaping add old world charm. Extensive use of black walnut on floors, staircase and main floor den. Custom millwork abounds.

163 Chartwell Road Interior

Entrance Hall

Built-in cabinetry throughout. Opulent master bedroom walks out to a balcony & offers a romantic fireplace, dressing room plus walk-in closet, vaulted ceiling plus a 5-piece spa inspired ensuite.

The second level boasts a den & a gallery hall with barrel roll ceiling. Seven fireplaces; 5 + 4 baths; built-in audio system; elevator; gated entry; detached office.

#12.) Bass Island, Muskoka

Price: $11,800,000.00

Elegantly Designed Architectural Masterpiece On Lake Muskoka Presenting 11,000 Square Feet Of Luxury Living.

Bass Island

Bass Island

Expert Craftsmanship and exquisite building materials sourced from around the globe offer the best quality available. Bi-folding Doors & Glass Walls Made With Pacific Reflective Blue Glass Show Off Panoramic Sunset Views.

Flooring Includes Tile Imported From Italy, Spain & Walnut From The USA.

Gourmet Kitchen With Glass Illuminated countertop is elegantly finished with top of the line Bosch and Electrolux appliances and handmade cabinetry.

Bass Island Kitchen

Bass Island Kitchen

Each room has individual Digital touch screen thermostat panels to regulate the temperature from anywhere in the world with just the touch of your smartphone or computer.

Bass Island Master

Bass Island Master

Bask in the luxury of the state of the art Finnish dry sauna or Turkish steam room.Some of the features of the 1200 sq ft spa include handmade heated marble benches, a six ft deep cold plunge pool and resistance swimming pool with Badu jets and heated stone flooring.

#11.) 61 The Bridle Path, Toronto

Price: $12,788,000.00

A world class luxury residence situated on most spectacular secluded 2 acres gated estate, located on prestigious Bridle Path. The home was owned by acclaimed international music celebrity.

61 Bridle Path front

61 Bridle Path

Approx. 14,280 Sq Ft of living space. This sensational bungalow offers a dramatic floor plan and a majestic ambience for entertaining.

61 The Bridle Path 3

Entrance Hall

Chef inspired Downsview kitchen! Oversized skylights.

61 THE BRIDLE PATH kitchen


Encompassed by lavish foliage, sprawling grounds tennis court, award winning pool, heated cabana with 3 Pc. Ensuite and kitchen. Serene tranquility abounds!

#10.)  2533 Ridge Road West, Oro-Medonte

Price: $13,000,000.00

Welcome to your private resort. Gated 17 1/2 acres of exquisite living,

2533 Ridge Rd. W., Oro-Medonte

2533 Ridge Road West, Oro-Medonte

4 treed acres for your complete privacy with 730 Ft of pristine water frontage on Kempenfelt Bay.

Just 10 minutes from downtown Barrie and one hour from Toronto.

2533 Ridge Rd. W., Oro-Medonte2

The View From the Back Door of the House

This property consists of a 6100 Sq.Ft of living space.

2533 Ridge Rd. W., Oro-Medonte7

View from the Living Room

5 Bedrooms, 6 Bathrooms. Inground custom made infinity pool with a swim-up bar and hot tub.

2533 Ridge Rd. W., Oro-Medonte9


Another hot tub located on the water with a custom bar to just lay back and relax.

#9.)  75 Highland Crescent, Toronto

Price: $13,950,000.00

Awe-inspiring views over The Rosedale Ravine and golf course.  A 4 bedroom and five bathrooms cutting-edge design of approximately 13,000 Sq. Ft. (Inc. Lower Level)


75 Highland Crescent

Property with the steel frame and concrete construction.  Private spa, wine cellar and wet bar.  Indoor walk-in pool, whirlpool and cold plunge.

75 HIGHLAND CRES, Toronto2

Central Hallway

Smart Home Integration And Underground Hydraulic Garage Lift.

75 HIGHLAND CRES - kitchen

Custom Boffi Kitchen

Custom Boffi Kitchen. White oak flooring, three mechanical rooms, 18′ deep cooling tower.

75 Highland Crescent, Toronto, Canada | Luxury Real Estate

Lower Level Swimming Pool

Radiant heat flooring, power entry gate, security cameras and driveway snow melting system.

#8.)  5 Park Lane Circle, Toronto

Price: $13,980,000.00

Stately gated 15,785 custom built residence on a beautiful 2-acre lot.


5 Park Lane Circle

Lowest price per foot in Bridle Path Estates area. Pristine manicured gardens with circular driveway, tennis court, indoor pool, hot tub and spa.

5 PARK LANE CIRC, Toronto2

2 Storey Grand Salon Entry

Two storey grand salon entry. Crema Marfil marble floors. Extensive millwork and crown moulding. Gourmet size kitchen. Main floor theatre, Library.  Lavish seven pc. ensuite. Grand 5 bedroom suites with 10-foot ceilings

5 PARK LANE CIRC, Toronto3

Great Room

Upper lounge and bar.  & Bd. Study. Gold leaf detailing, gold plated hardware, wrought iron & marble grand staircase.

5 PARK LANE CIRC, Toronto5

Catering Kitchen


5 Car garage, Dectron pool system.  Shutters. Hardwood and marble throughout. In-ground sprinkler system.

#7.)  40 Park Lane Circle, Toronto

Price: $13,980,000.00

The Bridle Path Estate. Offered at final stages of completion.

40 Park Lane Circle 1

40 Park Lane Circle

Fashioned after the palace of Versailles in France, influenced by Louis the 14 era and the Palladian styles of Europe.

40 PARK LANE CIRC, Toronto4

Unfinished Front Hall

Over 21,000 square feet of living space. The Bridle Path Estate is a one-of-a-kind property situated on a lush 2.3 acres with panoramic views overlooking an immense conservation area and nestled within the famed Bridle Path area of Toronto.

40 PARK LANE CIRC, Toronto2


Grand Ballroom, In+Outdoor Pools, W/O To Terraces, Mn Flr. Hm.Theatre Rm. Sep.Winged Off.Or In-Laws Suite W/Fp, Lr Or Boardroom,

40 PARK LANE CIRC, Toronto6

Walk-in Closet


#6.)  14 The Bridle Path, Toronto

Price: $14,950,000.00

Opulent Gated Palatial Estate On Most Prestigious Bridle Path.

14 The Bridle Path, Toronto1

14 Bridle Path

Boasting over 22,000 square feet of luxurious living space. 2-story grand salon entry with spectacular millwork.

14 The Bridle Path, Toronto8

2 Storey Grand Salon Entry

Auto gated entries. Elevator. 4 car garage. Crestron system.

14 The Bridle Path, Toronto3


Two gourmet Neff Kitchens. Magazine featured. Chef inspired kitchen. An entertainers dream with a movie theatre, ballroom, indoor pool & 3rd kitchen. Awe inspiring private master bedroom retreat with boudoir.

14 The Bridle Path, Toronto2

Theatre Room

Separate in-law suite with two bathrooms  & 2 bedrooms. Wine cellar. Heated floors. Built-in speakers, antique vanities & light fixtures.

#5.)  263 Warren Road, Toronto

Price: $15,680,000

Spectacular custom built residence graced with impeccable appointments & finest of architectural details.

263 Warren Road

263 Warren Road

Mahogany framed glass front door with decorative iron & 24 carats gilded grill. Polished mahogany cabinetry in library & office.

French doors from living & family rooms open to the terrace, gardens & pool. There is an 8′ radial breakfast area in family room.

263 Warren Road1

Entrance Hall

Gas fireplaces (convert to wood ) in living, dining, library & master suite. Custom Falcon kitchen. Mud room with change room & 3-piece bathroom. Loggia with limestone and granite floor.

263 Warren Road2

Great Room

Glass domed coffered ceiling. Outdoor kitchen with freezer, fridge, Wolf grill. Lower level lounge, wet bar with kitchen, Wine cellar, massage room, spa, yoga room, gym.

263 Warren Road3

Lower Level

Double entry to potential home theatre Landscaped gardens, heated walkway to the hot tub, dramatic lighting. Pool ( 30′ X 16′). Snowmelt on major walkways.

#4.)  28 Valleyanna Dr, Toronto

Price: $16,800,000

Framed in broad, verdant beauty, this Valleyanna masterpiece stands majestically in a storybook setting surrounded by the beauty of exquisite gardens.

28 Valleyanna Dr

28 Valleyanna Dr

Natural light freely cascades through w-w windows in living & dining rooms, library, master suite & other bedrooms creating an ambience of spacious flow.

28 Valleyanna Dr2

Exquisite Gardens

Lower family room features fieldstone wood-burning fireplace, walk-out to terrace & games room complimented by a fully-serviced wet bar. . 32 seat home theatre. Indoor pool & lounge area with walk-out & 2 change rooms Expansive north & south terraces provide dramatic vistas of the valley.

28 Valleyanna Dr1

More Gardens

Reflecting pool, manicured hedges, waterfalls descending 100 feet to Don River & bucolic, pastoral meadow to enjoy the natural habitat.

28 Valleyanna Dr6

Catering Kitchen

Coach house (1,375 sq. ft). 2 bedrooms, finished lower level. Excellent location. Close to best private & public schools, recreation facilities & parks, easy access downtown& public transit on Bayview Ave.

#3.)  46 Park Lane Circle, Toronto

Price: $16,900,000

Magnificent three years new French country chateau inspired masterpiece on most prestigious Park Lane Circle.

46 Park Lane Circle

46 Park Lane Circle

Grandeur and elegance abound at this gated, custom 13,385 total square foot home (+2,650 square foot garage). Built by renowned Mazenga Building Group. Situated on approximately 4 acres of private, pristine ravine.

46 Park Lane Circle2

Situated on approximately 4 acres of private, pristine ravine

Manicured extensively landscaped gardens with Infiniti hot tub, circular drive and flagstone terraces. Chef inspired kitchen with walk-in pantry. Anteroom, butler’s server and convenient centre island with breakfast bar. Unparalleled master bedroom retreat with soaring ceilings, stone terrace balcony overlooking ravine.

46 Park Lane Circle3

Entrance Hall

Lavish his and hers closets and opulent seven-piece ensuite. Upper-level family room and office. Heated marble floors throughout and extensive millwork. Separate nanny apartment with kitchen, living room, laundry room and four pieces ensuite.

46 Park Lane Circle5


Lower Level Boasts Recreation Room, Games Room, Spa, Gym And Wine Cellar. Grand Marble Slab Staircase With Wrought-Iron Detailing. Snowmelt For Driveway, Front Steps And Stone Terrace. Slate Roof. Elevator. 8 Car Garage. Oasis Awaits!

#2.) 35 High Point Road, Toronto

Price: $19,800,000

The house has more amenities than some condominiums in the city. With its very own indoor pool and spa, exercise room, his and hers change rooms, party room with commercial grade kitchen, wine cellar, billiards room, home theatre and tennis court, it truly has something for everyone.

35 High Point Road3

35 High Point Road3

It even features its own playroom with specialized rubber for the little ones.

35 High Point Road4

35 High Point Road Rear of the House

The exquisitely landscaped grounds make living in the city feel like cottage country.Hand carved marble mantles.

2-Stry pool/ball room-50′ Pool with Dedon furniture.

35 High Point Road6


Stn Terr W/Euro.Kettal/Tucci Furn. Aged Ital.Marb.Flrs. Elab.C/Mould. Fr.Drs. Downsv Kit, Eleven, Mbr W/H+H Ens+Boudoirs, Butlers Loft, 7 Wood Fps, Dectron Pl Sys,

35 High Point Road8

Pool/Ball Room

Tennis, gazebo, potting cabin. Gently sloping to Wilket Creek ravine.

#1.) 68 Bridle Path, Toronto

Price: $25,000,000

The gated four-acre property and 28,000 sq. ft. home at 68 The Bridle Path was built by financier and real estate developer Robert Campeau in the early 1980s.


68 Bridle Path

An extravagant 10-bedroom, 14-washroom gated French-style chateau on the Bridle Path has an Olympic-sized swimming pool with a retractable floor that turns the space into a ballroom.



The home has played host to notable guests like Pierre Elliott Trudeau and Jane Fonda. Even better, it played the home of one of the Olsen twins in the movie It Takes Two.



Space is now move-in ready and equipped with antique furnishings, crystal chandeliers and original artwork.



40-car garage, seven wood-burning fireplaces, three storeys, elevator, tennis court.


Night Time

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