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Caledon

15466 The Gore Rd. (The Gore Road and Castlederg Side Road)

Asking price: $16.8 million

Taxes: $51,391 (2026)

Bedrooms: 7

Bathrooms: 9

Square footage: 9,500

Garage: 5

Parking: 15

MLS# W13078716

“To me, what stands out about this property is the freedom and flexibility it gives you,” says listing agent Tyler Cohen. “You can be in the main house, take a walk through the forest, spend the afternoon by the pool or multiple ponds, relax at the spa, or escape to the beach house. Every part of the property offers a different experience, but it all feels connected. That combination of luxury, nature and privacy is what makes it so special.

“It will appeal to someone who appreciates exceptional design and craftsmanship, but also wants the freedom, privacy and connection to nature.”

The approximately 9,500-square-foot house was renovated from top to bottom four years ago. Cohen’s top three interior features include the great room. “It’s truly the heart of the home with its dramatic scale, beautiful architectural detailing, a two-way fireplace and a seamless connection to the terrace. From the moment you enter, there’s a feeling reminiscent of walking into an exceptional private country club or an elegant golf resort.”

Cohen’s second favourite is the glass-domed conservatory, which is “perhaps the most distinctive feature. It creates a completely different experience from the rest of the house and is a beautiful example of how the design continually brings the outdoors in,” he says.

“Another feature I love is the lower-level entertainment and wellness space. It feels like having a private club within the home, with a beautifully designed spa, a full gym and a state-of-the-art golf simulator room. You can work out, unwind, spend time with family or friends. It’s designed for someone who wants to enjoy a resort-like experience without having to leave home.”

What also makes the property so unique is the flexibility of having multiple fully liveable spaces. In addition to the main residence, there’s a spacious suite above the garage, a gatehouse with its own living quarters and a fully functional beach house overlooking a private swimming pond with white sand. It gives the property an incredible versatility,” Cohen says.

Luxury isn’t limited to finishes inside the home, he says. The 52.5 acres offer “a lifestyle that is both incredibly sophisticated and wonderfully relaxed.”

Listing Broker: ReMax Realtron Barry Cohen Homes (Tyler Cohen and Barry Cohen)

Estate designed as an enclave for family enjoyment

King

12800 8^th Concession (King and Mill roads)

Asking price: $18.8 million

Taxes: $22,919 (2026)

Bedrooms: 4

Bathrooms: 5

Square footage: 5,000

Garage: 5

Parking: 15

MLS# N13415604

This farm has been home to some exceptional competition horses, including Stuntman, who competed at Spruce Meadows, says listing agent Valerie Smith. “But what comes through most strongly is that Wingberry was created as a family property. Three generations were able to live here, and the homes, pool, great room and riding facilities all became places where they gathered.”

The country estate was developed over time. “The main house was built in the 1970s.  The current owners have continued to expand and improve the property,” Smith says. “The gatehouse was completed in 2018 and the indoor pool and spa addition to the main residence was completed in 2019.”

The three residences vary in size and each includes staff and nanny accommodations. The main house offers about 5,000 square feet of above-ground living space.

“For me, it is the great room in the main residence that is the best interior feature,” Smith says. “It has wonderful scale, with a stunning high ceiling and floor-to-ceiling glass sliding doors but still feels warm and comfortable. It connects beautifully to the backyard and forest. The indoor pool is adjacent to the grand room so you feel like you are in a lovely resort.”

The 75-acre property’s trail system wind through the forest and along the creek, the swimming pond and across the horse pastures. At the highest point is a log cabin-style studio with panoramic views.

The equestrian facilities include more than 30 stalls, a heated indoor arena, professional outdoor riding rings, paddocks and supporting workshops.

“One of the most personal stories is that the owners’ daughter was married on the farm. She and her father both rode into the ceremony on horseback. She rode Serengeti, a horse she had owned since childhood.”

Listing Broker: Sotheby’s International Realty Canada (Valerie Smith, Paul Maranger and Christian Vermast)

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