Explore the finest of Ontario’s real estate with these five luxurious estates and properties located in the region’s most desirable areas. From expansive homes boasting private sports facilities, opulent custom interiors, and serene settings near conservation areas, to rare executive residences offering extensive upgrades and entertainment options, each property blends luxury, comfort, and privacy.
Luxury Sports Retreat | $4,850,000
This stunning custom 3+1 bedroom home/chalet on a unique 24-acre property offers both luxury and privacy. The main level features an open-concept chef’s kitchen, stone fireplace, multiple walk- outs, and a spacious primary suite, while the upper level includes two additional bedrooms and a full bath.
Size: acres
Price: $4,850,000
Listing details: The fully finished lower level provides a media room, pool/games room, guest bedroom, and walk-out. A private indoor arena, featured on Hometown Hockey, includes a 45’x95’ ice surface, pickleball court, Zamboni, change rooms, steam shower, and a viewing gallery with a pub/bar. The loft with an 80” TV and hot tub offers a relaxing space after a day of fun. With scenic views, extensive trails, and bordering Osler Bluff Ski Club, this property is ideal for sports enthusiasts and nature lovers, offering a perfect blend of recreation, entertainment, and tranquility.
Contact: Daena Allen-Noxon & Associates, Sotheby’s International Realty Canada, +1 416.960.9995
39 Valleyford Avenue | $4,788,000
Rare executive home in a tranquil cul-de-sac beside a parkette.
Size: sf
Price: $4,788,000
Listing details: This 8000 sq ft custom-built residence features a 4-car garage, 19ft marble foyer, gourmet kitchen, primary suite with a gas fireplace, and an entertainment basement with a rec room and theater. Outside, enjoy a saltwater pool, cabana, sunroom, mini-golf green, and outdoor bar/ kitchenette. Over $400K in upgrades.
Contact: Daryl King, RE/MAX Hallmark Realty Ltd, +1 905.907.5464
3 Rutland Hill Court | $4,340,000
Stunning Victorian Reproduction home with over 6600 square feet total, perfectly located on a dream 15+ acre oasis amongst a quiet collection of estate homes, just minutes from Caledon East and Orangeville. The backyard includes a luxurious oversized copper-ionized pool with built-in safety ledge, custom cabana milled on site with wet bar, wood burning fireplace and laundry. 30’ x 40’ heated and insulated drive shed, approximately 5 acres of cleared land with 10+ acres of forest and trails, custom built stream and waterfall, fully engineered hockey rick with drainage and lighting (potential to convert to a pickleball or tennis court), tobogganing hill and play set, and fully manicured lawns and gorgeous gardens.
Size: sf
Price: $4,340,000
Listing details: Inside, you will find an expansive, yet cozy living space filled with natural light. Custom dove- tailed wood cabinetry in the kitchen with 2 dishwashers and heated slate flooring. Open concept living area with a beautiful view and walk out to the newly refinished patio (2024) and vaulted ceilings in the living room. Formal dining room which could be easily converted to a main floor primary with ensuite. Main floor laundry. High speed internet throughout the home and backyard. 5 large bedrooms on the second floor plus an additional bedroom in the basement. Bright primary bedroom with spa-like ensuite. 6 bathrooms total. Sauna and games room in the walk-out basement. The perfect home for multi-generational living, raising a family or entertaining friends.
Contact: Hilary Matthews, Harvey Kalles Real Estate Ltd., +1 647.354.9506
Zoned And Site Plan Approved For 4 Storey Mixed Use Building Currently In High Demand Location With Full Utilities | $4,288,000
LAND BEING SOLD TO DEVELOPING COMPANY.
Size: – sf
Price: $4,288,000
Listing details: PROPERTY HAS POTENTIAL FOR 6 STORIES CURRENTLY LISTED FOR SALE AS MIXED USE GREAT LOCATION WITH SHOPPING, UTILITIES AND CONVIENIENCES ALL AROUND LAND. **** EXTRAS **** LEVEL GROUND, UTILITIES AT ROAD, GAS, ELECTRICAL, INTERNET, WATER AND SEWER (36476105)
Contact: Richard Miller, RICHART REALTY INC., +1 519.681.9888
The Pinnacle Of Luxury Home | $4,100,000
The pinnacle of luxury is here! Welcome to 241 Tamarack. This home features over 10,000 sq ft of living space and is tucked away on a generous lot backing onto a conservation area. From the moment you drive in you’ll be impressed with the feeling of grandeur. The driveway alone can facilitate parking for over 10 cars, including an oversized triple garage , accommodating 3 cars, plus any other equipment you need! Once inside the home, we have no doubt you’ll be swept away. Stunning center hall plan with a sweeping custom staircase and art exhibit hallway at the top. If you aren’t in the mood for stairs, feel free to take the elevator!
Size: sf
Price: $4,100,000
Listing details: Each room of this home has been thoughtfully designed from the custom art deco solid wood doors, the custom ornate tile work and more. 2 full kitchens, featuring Wolfe appliances 2 laundry rooms and 9 bathrooms total. All exquisitely designed down to the last detail. Generous living spaces like a formal living and dining room make the main floor an excellent space for entertaining . The upper level offers 2 full primary suites, plus an additional bedroom with it’s own bath and walk in closet. The primary has an incredible soapstone fireplace, his and hers dressing rooms and his/hers ensuites both with heated flooring. The room over the garage offers limitless possibilities, from a lounge, to added living space, games area and wet bar with small kitchenette, complete with an air filtration system in case cigars are your fancy! The lower level offers full walk out privileges from all rooms. There are 2 full bedrooms with their own baths. The custom bar with separate wine room is sure to please. A full kitchen in the lower level is perfect for those extended guest stays. Private gym, custom pool with extensive hardscaping, hot tub. 3 deck/lounge areas. The list is extensive and incredible! Don’t miss the chance to own one of the city’s most luxurious homes ever built! Take a tour in the virtual tour to see everything!
Contact: Drew Symons & Jennifer Gale, Gale Group Realty Brokerage Ltd, +1 519.532.5250, 519.535.0357