5906 Winston Churchill Boulevard
Rural Erin Wellington N0B 1T0

$3,299,999
Residential Freehold beds: 4 baths: 5.0

Professional Landscape
Photo 1: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 2: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 3: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 4: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 5: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 6: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 7: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 8: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 9: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 10: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 11: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 12: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 13: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 14: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 15: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 16: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 17: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 18: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 19: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 20: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 21: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 22: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 23: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 24: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 25: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 26: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 27: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 28: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 29: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 30: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 31: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 32: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 33: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 34: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 35: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 36: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 37: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 38: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 39: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 40: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 41: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 42: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 43: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 44: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 45: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 46: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 47: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 48: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Photo 49: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
X12141857
Bedrooms:
4
Bathrooms:
5
A world of timeless sophistication and unparalleled exclusivity unfolds. Nestled on 18 secluded acres, this estate boasts over 5,450 square feet 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, Miami-style modern landscaped pool area, and woodland greet you, centering around your private pond. Meandering trails weave through the untouched serenity of nature, offering an idyllic escape for exploration and tranquility. Crafted with a superior level of artistry and bespoke finishes, the residence combines timeless design with modern functionality. The grand primary suite serves as a personal retreat with its sitting room, a private balcony, and views that inspire morning reflection or evening serenity. The heart of the home is its gourmet kitchen, complemented by four well-appointed bedrooms & five 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 and outdoor venues blend into the meticulously landscaped grounds, with multiple lounging areas, outdoor kitchen, 2520 sqft of reflective glassed-in pool area with an infinity edge saltwater pool. An elegant covered cabana provides a wood-burning fireplace, pop-up TV, sauna, wet bar, changing room, two-piece bathroom, and an outdoor shower. 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 Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
2-Storey
Total Approx Floor Area:
3500-5000
Lot Size:
10-24.99
Depth:
1638'
Frontage:
500'
Lot Shape:
Rectangular
Topography:
Wooded/Treed
Direction Faces:
West
Bedrooms:
4
Bathrooms:
5.0
Water supply:
Well
Kitchens:
1
Bedrooms Above Grade:
4
Kitchens Above Grade:
1
Rooms Above Grade:
7
Rooms Below Grade:
3
Ensuite Laundry:
No
Heating type:
Forced Air
Heating Fuel:
Propane
Fireplaces:
2
Foundation:
Concrete Block
Roof:
Asphalt Shingle
Basement:
Finished, Full
Fireplace Features:
Fireplace Insert, Propane
Fireplace/Stove:
Yes
Alternative Power:
Generator-Wired
Garage:
Detached
Garage Spaces:
2.0
Parking Features:
Circular Drive, Private Triple, Front Yard Parking, Private Double, Private
Parking Spaces:
16
Total Parking Spaces:
18.0
Family Room:
Yes
Possession Details:
T.B.D.
Lot Irregularities:
18.4 ACRES
Pool:
Inground
Link:
No
HST Applicable To Sale Price:
Included In
Taxes:
$10,015.24 / 2024
Assessment:
$- / -
Erin
Rural Erin
Wellington
Wooded/Treed, Golf, Greenbelt/Conservation, Lake/Pond, River/Stream
Bar Fridge, Generator - Full, Propane Tank, Water Purifier, Water Treatment
Security System
Conservation Regulations
Propane tank to main home
Fridge, Stove, Range, D/W, Washer & Dryer, Projector and Screen in Media rm, Pool Solar & propane pool heating system, Bar Fridge, Pop up TV, Sauna in Cabana, HotTub, All Pool related Equipment, Outdoor Fridge and BBQ , Playground. Refer to list attached.
Traeger smoker, Pizza oven
Board & Batten, Stone
Direct
Unknown
Direct
Pond
Floor
Type
Size
Other
Main
Kitchen
10'11½" × 10'8"
Stone Counters, Breakfast Bar, Beamed Ceilings
Main
Dining Room
13'4" × 13'2"
W/O To Porch, Breakfast Bar, Plank
Main
Living Room
28'10" × 17'6"
Fireplace Insert, W/O To Patio, Beamed Ceilings
Main
Bedroom 3
16'6" × 14'5"
Walk-In Closet(s), Ceiling Fan(s), Picture Window
Main
Bedroom 4
13'1" × 11'6"
Hardwood Floor, Picture Window, Plank
Second
Primary Bedroom
28'10" × 16'11"
3 Pc Ensuite, Juliette Balcony, Fireplace
Second
Loft
16'11" × 7'6"
Combined w/Primary, Overlooks Backyard, Laminate
Second
Bedroom 2
19'3" × 16'6"
Juliette Balcony, Beamed Ceilings, Overlooks Frontyard
Basement
Media Room
25' × 17'10"
Laminate, Pot Lights
Basement
Family Room
17'8" × 11'9"
3 Pc Ensuite, Laminate
Basement
Office
13'6" × 11'9"
Laminate
Main
Laundry
7'10⅞" × 7'3"
Picture Window
Utilities Hydro:
Yes
Water Supply Types:
Drilled Well
Special Designation:
Unknown
Sewers:
Septic
Air Conditioning:
Central Air
Central Vacuum:
No
Seller Property Info Statement:
No
Laundry Level:
Main Level
Date Listed:
May 12, 2025
Original Price:
$3,299,999
  • Photo 1: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Professional Landscape
  • Photo 2: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Outdoor Living Space
  • Photo 3: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    18 Acres
  • Photo 4: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Private Backyard
  • Photo 5: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    2nd Outdoors Living Area
  • Photo 6: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Infinity Pool
  • Photo 7: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Glass Surrounding Pool
  • Photo 8: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Evening Photos of the Cabana and Pool
  • Photo 9: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Evening View
  • Photo 10: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Multiple Fire Places
  • Photo 11: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Chef's Kitchen
  • Photo 12: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Island
  • Photo 13: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Photo 13 of 49
  • Photo 14: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Spacious Dining Room
  • Photo 15: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Cathedral Ceiling Dining Room
  • Photo 16: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Living Room with Wood burning Fireplace
  • Photo 17: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Walk-out to Patio and Pool
  • Photo 18: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Stone Wood Fireplace
  • Photo 19: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Main floor Bathroom
  • Photo 20: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Mudroom - Side Entrance
  • Photo 21: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Primary Bedroom Gas Stone Wall Fireplace
  • Photo 22: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Cathedral Ceilings
  • Photo 23: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Private Balcony overlooking the Pool
  • Photo 24: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    2nd Bedroom with Private Balcony
  • Photo 25: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    2nd Bedroom with Private Balcony
  • Photo 26: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Basement Family Room
  • Photo 27: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Media/Theatre Room
  • Photo 28: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Steam Shower and Heated Flooring
  • Photo 29: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Outdoor Kitchen
  • Photo 30: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Outdoor Dining Area
  • Photo 31: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Covered Cabana
  • Photo 32: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Photo 32 of 49
  • Photo 33: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Photo 33 of 49
  • Photo 34: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Photo 34 of 49
  • Photo 35: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Cabana with Wood Fireplace
  • Photo 36: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Cabana with Wet Bar
  • Photo 37: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Cabana with Sauna
  • Photo 38: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Cabana with Change Room and 2 Pcs Bathroom
  • Photo 39: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Photo 39 of 49
  • Photo 40: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Side Private Patio are
  • Photo 41: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Photo 41 of 49
  • Photo 42: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Photo 42 of 49
  • Photo 43: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Solar Heating for Pool
  • Photo 44: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Photo 44 of 49
  • Photo 45: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Photo 45 of 49
  • Photo 46: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Pond including Fountain
  • Photo 47: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Photo 47 of 49
  • Photo 48: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
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  • Photo 49: 5906 Winston Churchill Boulevard in Wellington: Rural Erin House for sale (Erin)  : MLS®# X12141857
    Photo 49 of 49

Virtual Tour

Listed by SOTHEBY'S INTERNATIONAL REALTY CANADA
Data was last updated May 13, 2025 at 12:15 AM (UTC)
Area Statistics
Listings on market:
70
Avg list price:
$1,849,000
Min list price:
$598,000
Max list price:
$4,999,000
Avg days on market:
54
Min days on market:
1
Max days on market:
406
These statistics are generated based on the current listing's property type and located in Rural Erin. Average values are derived using median calculations.
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.