Forgot password Extend Verify Contact

14294 Winston Churchill Boulevard
Rural Caledon Caledon L7C 3E8

$2,389,000
Residential Freehold beds: 4 baths: 3.0

Main Photo: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 1: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 2: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 3: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 4: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 5: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 6: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 7: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 8: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 9: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 10: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 11: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 12: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 13: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 14: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 15: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 16: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 17: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 18: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 19: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 20: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 21: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 22: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 23: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 24: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 25: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 26: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 27: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 28: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 29: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 30: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 31: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 32: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 33: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 34: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 35: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 36: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 37: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 38: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 39: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 40: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 41: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 42: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 43: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 44: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Photo 45: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
W12591338
Bedrooms:
4
Bathrooms:
3
In the storybook hamlet of Terra Cotta, Caledon, just steps from the Cataract Trailway and Terra Cotta Conservation Area, this exceptional property offers elegance and a deep connection to nature. Nearly 2.5 acres back onto protected conservation land with no rear neighbours - only forest, fresh air, and birdsong. The lot blends cleared lawn and woodland, with sunny spaces for entertaining and shaded spots for quiet reflection. Your fenced backyard oasis is anchored by a heated saltwater pool with a waterfall, an expansive patio for barbecues and lounging, and the ultimate privacy of your own forest. Inside, vaulted ceilings and large windows flood the main living areas with natural light. The formal dining room sits off the foyer behind French doors, while the grand two-storey living room features a two-way wood-burning fireplace shared with the breakfast room. The chefs kitchen boasts top-of-the-line Miele appliances, including an oversized fridge, built-in oven, sleek cooktop, and flush-mount range hood. A spacious sunken family room off the breakfast and kitchen opens to the backyard. The main floor also offers a laundry room with a walkout and a spa-inspired 3-pc bath with heated floors and a glass shower, perfect after a swim. Upstairs, the open loft hallway provides space for an office, hangout space, or reading nook. Four bedrooms include a sprawling primary suite with his-and-hers walk-in closets. The finished basement offers a huge rec/games room plus a bonus room - ideal as a gym, extra bedroom, or office. An insulated double-car garage with epoxy flooring completes this property. From sunrise coffee on the patio to starlit swims beneath the trees, this Terra Cotta retreat is more than a home - its a lifestyle.
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
2-Storey
Approx. Age:
31-50
Total Approx Floor Area:
3500-5000
Lot Size:
2-4.99
Lot Depth:
416'2"
Lot Frontage:
232'4"
Direction Faces:
West
Bedrooms:
4
Bathrooms:
3.0
Water supply:
Well
Kitchens:
1
Bedrooms Above Grade:
4
Kitchens Above Grade:
1
Rooms Above Grade:
10
Rooms Below Grade:
2
Zoning:
A1*
Heating type:
Forced Air
Heating Fuel:
Propane
Fireplaces:
2
Foundation:
Concrete Block
Roof:
Shingles
Basement:
Finished, Full
Fireplace Features:
Propane, Wood
Fireplace/Stove:
Yes
Garage:
Attached
Garage Spaces:
2.0
Other Structures:
Fence - Full, Fence - Partial, Other
Parking Features:
Private Double
Parking Spaces:
6
Total Parking Spaces:
8.0
Family Room:
Yes
Possession Details:
TBA
Pool:
Inground, Salt
Link:
No
HST Applicable To Sale Price:
Included In
Taxes:
$6,607.3 / 2024
Assessment:
$- / -
Peel
Caledon
Rural Caledon
Fenced Yard, Greenbelt/Conservation, Lake/Pond, Wooded/Treed
Auto Garage Door Remote, Central Vacuum, Propane Tank, Storage, Sump Pump, Water Heater Owned, Water Softener, Water Treatment
Backs On Green Belt, Landscaped, Patio, Privacy
Security System, Monitored
Propane Tank
All Window Coverings and Screens, Including Hardware; Electric Light Fixtures and Ceiling Fans with Remotes; Water Softener; Water Heater; Closet Organizers; All Bathroom Shower Rods and Mirrors; Existing Microwave, Oven, Cooktop, Range Hood, Fridge, Dishwasher; All Garage Door Openers and Remotes; Clothes Washer and Clothes Dryer; Central Vacuum and all Related Equipment; TV Wall Mounts; Pool, Pump and all Related Equipment; Water Collection Barrels; Satellite Dish
Ping Pong Table; Outdoor Fireplace, Patio Furniture & Accessories, Hammock and Stand;
Stone, Vinyl Siding
Floor
Type
Size
Other
Main
Foyer
18'7¼" × 11'2¼"
Hardwood Floor, Double Closet, Vaulted Ceiling(s)
Main
Dining Room
13'3" × 12'9"
Hardwood Floor, French Doors, Crown Moulding
Main
Living Room
15'8" × 12'9"
Hardwood Floor, 2 Way Fireplace, Vaulted Ceiling(s)
Main
Kitchen
15'1" × 12'½"
Hardwood Floor, Quartz Counter, Centre Island
Main
Breakfast
12'7" × 12'3"
Hardwood Floor, 2 Way Fireplace, Large Window
Main
Family Room
19'1" × 19'1"
Broadloom, Sunken Room, W/O To Pool
Main
Laundry
8'4" × 5'6"
Tile Floor, W/O To Yard, Laundry Sink
Second
Primary Bedroom
21' × 19'1½"
Broadloom, Sunken Room, His and Hers Closets
Second
Bedroom
13'1" × 11'11"
Broadloom, Closet, Window
Second
Bedroom
15'4" × 9'5"
Broadloom, Closet, Window
Second
Bedroom
15'10" × 9'7"
Broadloom, Closet, Window
Basement
Recreation
31'½" × 27'10¼"
Broadloom, Fireplace, Above Grade Window
Basement
Exercise Room
25'3½" × 13'5"
Broadloom, Above Grade Window, Recessed Lighting
Special Designation:
Unknown
Sewers:
Septic
Air Conditioning:
Central Air
Central Vacuum:
Yes
Seller Property Info Statement:
No
Laundry Level:
Main Level
Date Listed:
Dec 01, 2025
  • Photo 1: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 1 of 45
  • Photo 2: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 2 of 45
  • Photo 3: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 3 of 45
  • Photo 4: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 4 of 45
  • Photo 5: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 5 of 45
  • Photo 6: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 6 of 45
  • Photo 7: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 7 of 45
  • Photo 8: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 8 of 45
  • Photo 9: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 9 of 45
  • Photo 10: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 10 of 45
  • Photo 11: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 11 of 45
  • Photo 12: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 12 of 45
  • Photo 13: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 13 of 45
  • Photo 14: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 14 of 45
  • Photo 15: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 15 of 45
  • Photo 16: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 16 of 45
  • Photo 17: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 17 of 45
  • Photo 18: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 18 of 45
  • Photo 19: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 19 of 45
  • Photo 20: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 20 of 45
  • Photo 21: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 21 of 45
  • Photo 22: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 22 of 45
  • Photo 23: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 23 of 45
  • Photo 24: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 24 of 45
  • Photo 25: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 25 of 45
  • Photo 26: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 26 of 45
  • Photo 27: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 27 of 45
  • Photo 28: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 28 of 45
  • Photo 29: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 29 of 45
  • Photo 30: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 30 of 45
  • Photo 31: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 31 of 45
  • Photo 32: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 32 of 45
  • Photo 33: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 33 of 45
  • Photo 34: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 34 of 45
  • Photo 35: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 35 of 45
  • Photo 36: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 36 of 45
  • Photo 37: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 37 of 45
  • Photo 38: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 38 of 45
  • Photo 39: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 39 of 45
  • Photo 40: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 40 of 45
  • Photo 41: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 41 of 45
  • Photo 42: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 42 of 45
  • Photo 43: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 43 of 45
  • Photo 44: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 44 of 45
  • Photo 45: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W12591338
    Photo 45 of 45
Listed by Coldwell Banker Elevate Realty
Data was last updated May 18, 2026 at 12:15 AM (UTC)
Area Statistics
Listings on market:
188
Avg list price:
$1,537,000
Min list price:
$495,000
Max list price:
$16,800,000
Avg days on market:
33
Min days on market:
1
Max days on market:
619
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.
WEI WANG
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.