We independently select everything we recommend.
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Buying through us may earn us a commission, which supports our work.
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Rural retreat loaded with freedom and flexibility
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.
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“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.
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Every part of the property offers a different experience, but it all feels connected.
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That combination of luxury, nature and privacy is what makes it so special.
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“It will appeal to someone who appreciates exceptional design and craftsmanship, but also wants the freedom, privacy and connection to nature.”
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The approximately 9,500-square-foot house was renovated from top to bottom four years ago.
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Cohen’s top three interior features include the great room.
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“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.
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From the moment you enter, there’s a feeling reminiscent of walking into an exceptional private country club or an elegant golf resort.”
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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.
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“Another feature I love is the lower-level entertainment and wellness space.
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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.
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You can work out, unwind, spend time with family or friends.
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It’s designed for someone who wants to enjoy a resort-like experience without having to leave home.
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What also makes the property so unique is the flexibility of having multiple fully liveable spaces.
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It gives the property an incredible versatility,” Cohen says.
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Luxury isn’t limited to finishes inside the home, he says.
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The 52.5 acres offer “a lifestyle that is both incredibly sophisticated and wonderfully relaxed.”
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Listing Broker: ReMax Realtron Barry Cohen Homes (Tyler Cohen and Barry Cohen)
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Estate designed as an enclave for family enjoyment
King
12800 8th 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.
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“But what comes through most strongly is that Wingberry was created as a family property.
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Three generations were able to live here, and the homes, pool, great room and riding facilities all became places where they gathered.”
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The country estate was developed over time.
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“The main house was built in the 1970s.
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The current owners have continued to expand and improve the property,” Smith says.
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“The gatehouse was completed in 2018 and the indoor pool and spa addition to the main residence was completed in 2019.”
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The three residences vary in size and each includes staff and nanny accommodations.
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The main house offers about 5,000 square feet of above-ground living space.
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“For me, it is the great room in the main residence that is the best interior feature,” Smith says.
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“It has wonderful scale, with a stunning high ceiling and floor-to-ceiling glass sliding doors but still feels warm and comfortable.
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It connects beautifully to the backyard and forest.
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The indoor pool is adjacent to the grand room so you feel like you are in a lovely resort.”
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The equestrian facilities include more than 30 stalls, a heated indoor arena, professional outdoor riding rings, paddocks and supporting workshops.
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“One of the most personal stories is that the owners’ daughter was married on the farm.
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She and her father both rode into the ceremony on horseback.
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She rode Serengeti, a horse she had owned since childhood.”
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The Aporia
