5906 Winston Churchill Boulevard photo 1
5906 Winston Churchill Boulevard photo 2
5906 Winston Churchill Boulevard photo 3
5906 Winston Churchill Boulevard photo 4
5906 Winston Churchill Boulevard photo 5
5906 Winston Churchill Boulevard photo 6
5906 Winston Churchill Boulevard photo 7
5906 Winston Churchill Boulevard photo 8
5906 Winston Churchill Boulevard photo 9
5906 Winston Churchill Boulevard photo 10
5906 Winston Churchill Boulevard photo 11
5906 Winston Churchill Boulevard photo 12
5906 Winston Churchill Boulevard photo 13
5906 Winston Churchill Boulevard photo 14
5906 Winston Churchill Boulevard photo 15
5906 Winston Churchill Boulevard photo 16
5906 Winston Churchill Boulevard photo 17
5906 Winston Churchill Boulevard photo 18
5906 Winston Churchill Boulevard photo 19
5906 Winston Churchill Boulevard photo 20
5906 Winston Churchill Boulevard photo 21
5906 Winston Churchill Boulevard photo 22
5906 Winston Churchill Boulevard photo 23
5906 Winston Churchill Boulevard photo 24
5906 Winston Churchill Boulevard photo 25
5906 Winston Churchill Boulevard photo 26
5906 Winston Churchill Boulevard photo 27
5906 Winston Churchill Boulevard photo 28
5906 Winston Churchill Boulevard photo 29
5906 Winston Churchill Boulevard photo 30
5906 Winston Churchill Boulevard photo 31
5906 Winston Churchill Boulevard photo 32
5906 Winston Churchill Boulevard photo 33
5906 Winston Churchill Boulevard photo 34
5906 Winston Churchill Boulevard photo 35
5906 Winston Churchill Boulevard photo 36
5906 Winston Churchill Boulevard photo 37
5906 Winston Churchill Boulevard photo 38
5906 Winston Churchill Boulevard photo 39
5906 Winston Churchill Boulevard photo 40
5906 Winston Churchill Boulevard photo 41
5906 Winston Churchill Boulevard photo 42
5906 Winston Churchill Boulevard photo 43
5906 Winston Churchill Boulevard photo 44
5906 Winston Churchill Boulevard photo 45
5906 Winston Churchill Boulevard photo 46
5906 Winston Churchill Boulevard photo 47
Geo Warehouse Lot Lines

5906 Winston Churchill Boulevard

Rural Erin / Erin, ON N0B 1T0

SoldFor Sale
4 Beds
5 Baths
3,500 Sq Ft
19 Lot Sq Ft
Single Family Home
This property has sold. Interested in something similar? Ask Filipe →

About This Property

A world of timeless sophistication and unparalleled exclusivity unfolds. Nestled on approx. 19 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 4 well-appointed bedrooms & 4+1(Cabana) 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 Adriane 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

Property Details

StatusSold
Property TypeSingle Family Home
Listing TypeFor Sale
Interior Size3,500 sq ft
Lot Size19 sq ft
Bedrooms4
Bathrooms5
ListedMay 6, 2026
Postal CodeN0B 1T0

Features & Amenities

  • View
  • Fireplace
  • Air Conditioning
  • Basement

TRREB MLS® Attribution

MLS® X12671694

Listed by SOTHEBY'S INTERNATIONAL REALTY CANADA

The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA. The trademarks REALTOR®, REALTORS® and the REALTOR® logo are controlled by CREA and identify real estate professionals who are members of CREA. Listing data provided by the Toronto Regional Real Estate Board (TRREB). The information contained herein is from sources believed to be reliable but is not guaranteed. Information deemed reliable but not guaranteed accurate by TRREB or Team Filipe / RE/MAX.

MLS®X12671694
TypeSingle Family Home
CityErin

Team Filipe · RE/MAX · (647) 210-6070

Listed By

SOTHEBY'S INTERNATIONAL REALTY CANADA