5906 Winston Churchill Boulevard

5906 Winston Churchill Boulevard
5906 Winston Churchill Boulevard
5906 Winston Churchill Boulevard
+45
4
 bed
5
 bath
20
 parking
3560
 sqft
Detached
* This unit size is calculated from property.ca data
$3,000,000
Instant Estimate Not Available
For Sale
1 day
 on site
$3,000,000
Instant Estimate Not Available
* This unit size is calculated from property.ca data
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Size
3560 sqft
Lot size
18 sqft
Street frontage
-
Possession
-
Price per sqft
$843
Taxes
$10,015.24 (2024)
Parking Type
-
Style
Two Story
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Description
A world of timeless sophistication and unparalleled exclusivity unfolds. Nestled on approx. 20 acres, this estate boasts over 5,450 sqft of exquisitely designed living space, set against the backdrop of a mature forest. Every step onto this estate unveils an extraordinary lifestyle. The moment you arrive, panoramic views of the water, modern crafted outdoor living space, pool area & woodland greet you, centering around your private pond. Trails weaving through the untouched serenity of nature, offering an idyllic escape for exploration & tranquility. Crafted with superior level of artistry, Post-and-beam construction, soaring cathedral ceilings & rich thick plank flooring throughout the home create warmth. The grand primary suite serves as a personal retreat with a sitting room, yoga studio, private balcony with enriched views that inspire morning reflection or evening serenity. The heart of the home is its gourmet kitchen, complemented by four well-appointed bedrooms & four + one bathrooms. Invision, unwinding by a stunning wood-burning fireplace, beautifully set against a dramatic stone wall. Whether it's the soft crackle of the fire or the serene views of your outdoor haven, every moment here invites you to relax, recharge, & revel in the luxury of your surroundings. This estate is a true entertainer's dream. Seamless indoor & outdoor venues, multiple lounging areas, outdoor kitchen, reflective glassed-in pool area, infinity edge saltwater pool, elegant thermal ash-clad cabana includes a wood-burning fireplace, pop-up TV, sauna, wet bar, change room, two-piece bathroom & outdoor shower, meticulously designed by Adrian Gale. The rejuvenating hot tub integrates into your private resort-like haven, Enjoy exclusive amenities including private trails, fishing, skating, all designed havens for discerning nature lovers seeking the pinnacle of luxury living. Conveniently located 1 hr from Toronto, minutes to TPC Toronto at Osprey Valley golf course & Caledon Ski Club
Broker: Sotheby's International Realty Canada
MLS®#: 40794924
Property details
Parking:
20
Parking type:
-
Property type:
Detached
Heating type:
Fireplace-
Style:
Two Story
MLS Size:
3560 sqft
Lot front:
500 Ft
Lot depth:
1638 Ft
Listed on:
Jan 7, 2026
Show all details
Rooms
LevelNameSizeFeatures
Main
Foyer
3.25 x 2.34 ft
Main
Kitchen
5.46 x 4.01 ft
Main
Dining Room
4.06 x 4.01 ft
Instant estimate:
Not Available

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About 5906 Winston Churchill Boulevard

5906 Winston Churchill Boulevard is a Caledon detached house for sale. It was listed at $3000000 in January 2026 and has 4 beds and 5 bathrooms.

Nearby grocery options: Ray Third Bistro Bakery is a 4-minute drive.

Getting around the area will require a vehicle, as the nearest transit stop is a Bus Stop (Riddell Rd / Town Line) and is an 8-minute drive

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