An exclusive luxury retreat
in the heart of Caledon.
Luxurious five bedroom estate set upon twenty-five acres of pristine countryside, offering panoramic views of the world class Paintbrush Golf Course.
Available for occupancy beginning Fall 2026. Availability is limited.
Welcome to Churchill House
Set on 25 acres of serene countryside, Churchill House offers privacy, comfort, and unforgettable views directly across from Paintbrush Golf Club. This fully furnished residence is thoughtfully designed for weekend escapes, extended stays, executive retreats, and special gatherings.
01
Play
Guests have the opportunity to enjoy exclusive access to the renowned Paintbrush Golf Club, Pulpit Club, and Caledon Ski Club.
Whether your ideal getaway includes championship golf, skiing, outdoor adventure, fine dining, or simply unwinding in complete tranquility, Churchill House provides an exceptional setting from which to experience the very best of Caledon.
Championship golf
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Skiing
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Outdoor adventure
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Fine Dining
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Championship golf ● Skiing ● Outdoor adventure ● Fine Dining ●
02
Stay
Designed for discerning guests, this beautifully appointed five-bedroom residence is fully furnished and thoughtfully curated for weekend escapes, extended stays, executive retreats, and special gatherings.
Unlike traditional vacation homes, Churchill House features a masterful primary suite with grand ensuite and four other equitable bedrooms (two with ensuites), each freshly furnished with a king-sized bed, premium linens, and luxury appointments, ensuring every guest enjoys the same exceptional level of comfort and privacy.
5 bedrooms
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King beds
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Premium linens
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Primary suite + ensuite
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Two additional ensuites
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5 bedrooms ● King beds ● Premium linens ● Primary suite + ensuite ● Two additional ensuites ●
03
Dine
The Churchill house has a fully appointed in house kitchen for those wishing to stay onsite and enjoy all of the retreats privacy.
Of course there is an option to enhance your stay with personalized recommendations for local five-star dining or arrange private catering services for a truly effortless experience.
Fully appointed in-house kitchen
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Local five-star dining recommendations
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Private catering arrangement
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Fully appointed in-house kitchen ● Local five-star dining recommendations ● Private catering arrangement ●
A first look at the Churchill House
Plan Your Stay
Experience the balance of tranquility, recreation, and refined country living.
Churchill House is currently preparing for guest stays beginning Fall 2026. Share your interest and we’ll follow up as availability and booking details are confirmed.