14020 Winston Churchill Boulevard
Rural Caledon Peel L7C 1P2

$4,998,888
Residential Freehold beds: 6+1 baths: 10.0

Main Photo: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 1: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 2: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 3: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 4: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 5: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 6: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 7: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 8: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 9: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 10: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 11: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 12: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 13: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 14: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 15: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 16: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 17: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 18: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 19: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 20: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 21: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 22: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 23: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 24: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 25: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 26: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 27: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 28: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 29: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 30: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 31: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 32: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 33: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 34: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 35: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 36: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 37: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 38: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 39: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 40: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 41: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Photo 42: 14020 Winston Churchill Boulevard in Peel: Rural Caledon House for sale (Caledon)  : MLS®# W12257849
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
W12257849
Bedrooms:
6+1
Bathrooms:
10
Architectural Masterpiece on 10 Private Acres! A true one-of-a-kind in Canada, this custom-designed modern estate is an architectural icon, privately nestled on 10 acres of pristine forest. Gated and set far back from the road, the home offers complete seclusion and a striking design that's unlike anything else featuring a dramatic rounded tower and sweeping arched lines, clad in high-end limestone. Step through the grand circular entrance into a show-stopping foyer with soaring cathedral ceilings, natural stone accents, and a custom-designed chandelier imported from England. A floating bridge on the second floor adds architectural drama, while floor-to-ceiling windows fill the home with natural light including a breathtaking 15x10 ft circular window in the family room. The chefs kitchen is outfitted with top-tier appliances, an oversized island with natural stone countertops, and an open flow perfect for entertaining. The main level also features formal living and dining rooms with a double-sided fireplace, a private office, and a large laundry room with custom cabinetry. Upstairs, six bedrooms offer stunning treetop views, complete privacy, and custom closets. The primary suite features a spa-like ensuite and spacious walk-in. The full walk-out basement offers a home theatre, bar, gym, steam shower, an additional bedroom and bath, and floor-to-ceiling windows for seamless indoor-outdoor living. Every inch of this home was built with comfort and technology in mind: radiant heated floors, built-in speakers throughout, individual thermostats for precise climate control. Outside, an in-ground pool surrounded by untouched natural beauty offers a tranquil escape and endless potential.
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
2-Storey
Approx. Age:
0-5
Total Approx Floor Area:
5000 +
Lot Size:
5-9.99
Depth:
1018'3"
Frontage:
317'3"
Direction Faces:
West
Bedrooms:
6+1
Bathrooms:
10.0
Water supply:
Municipal
Kitchens:
1
Bedrooms Above Grade:
6
Bedrooms Below Grade:
1
Kitchens Above Grade:
1
Rooms Above Grade:
17
Heating type:
Forced Air
Heating Fuel:
Gas
Foundation:
Concrete
Roof:
Metal, Flat
Basement:
Finished with Walk-Out, Separate Entrance
Fireplace/Stove:
Yes
Garage:
Attached
Garage Spaces:
3.0
Parking Features:
Available, Circular Drive, Private
Parking Spaces:
25
Total Parking Spaces:
28.0
Family Room:
Yes
Pool:
Inground
Link:
No
HST Applicable To Sale Price:
Included In
Taxes:
$5,004 / 2025
Assessment:
$- / -
Caledon
Rural Caledon
Peel
Clear View, Park, Ravine, Wooded/Treed
Auto Garage Door Remote, Built-In Oven, Carpet Free, Central Vacuum, Guest Accommodations, In-Law Suite, Steam Room, Storage, Sump Pump, Water Heater Owned, Water Softener, Water Treatment, Water Purifier
Controlled Entry, Privacy, Security Gate
Alarm System, Monitored, Security System, Smoke Detector
All electrical light fixtures, window coverings, S/S kitchen appliances: Wolfe stove and ovens, Sub Zero fridge, Miele coffee maker. Samsung Washer & Dryer, auto garage door remote (s), B/I speakers, pool (sold as is), 3 furnaces, 3 AC's & HWT.
Stone
Clear, Panoramic, Trees/Woods
Multiple Entrances, Open Floor Plan, Parking
Floor
Type
Size
Other
Ground
Kitchen
22'6" × 15'5"
Ground
Dining Room
33'9" × 21'1"
Ground
Living Room
51'3" × 24'
Ground
Foyer
22' × 16'9"
Ground
Laundry
19'6" × 15'9"
Second
Primary Bedroom
25'5" × 17'9"
4 Pc Ensuite, Double Sink
Second
Bedroom
19'3" × 16'2"
2 Pc Ensuite
Second
Bedroom 2
20'9" × 13'5"
3 Pc Ensuite
Second
Bedroom 3
20'9" × 13'7"
3 Pc Ensuite
Second
Bedroom 4
20'9" × 15'10"
3 Pc Ensuite
Second
Bedroom 5
20'7" × 14'2"
3 Pc Ensuite
Basement
Bedroom
15'3" × 12'
3 Pc Ensuite
Basement
Recreation
32'6" × 14'2"
Wet Bar
Basement
Recreation
39'10" × 21'5"
Floor
Ensuite
Pieces
Other
Ground
No
-
7'9" x 5'
Basement
No
3
10'4" x 8'5" 3 Pc Bath
Special Designation:
Unknown
Sewers:
Septic
Air Conditioning:
Central Air
Central Vacuum:
Yes
Seller Property Info Statement:
No
Date Listed:
Jul 02, 2025
Original Price:
$4,998,888
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Listed by ROYAL LEPAGE REALTY PLUS
Data was last updated August 5, 2025 at 08:15 PM (UTC)
Area Statistics
Listings on market:
202
Avg list price:
$1,597,450
Min list price:
$698,000
Max list price:
$29,000,000
Avg days on market:
52
Min days on market:
2
Max days on market:
564
These statistics are generated based on the current listing's property type and located in Rural Caledon. Average values are derived using median calculations. This data is not produced by the MLS® system.
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.