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14294 Winston Churchill Boulevard
Rural Caledon Caledon L7C 3E8

$1,988,000
Residential Freehold beds: 4 baths: 3.0

Main Photo: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W14114964
Photo 1: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W14114964
Photo 2: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W14114964
Photo 3: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W14114964
Photo 4: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W14114964
Photo 5: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W14114964
Photo 6: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W14114964
Photo 7: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W14114964
Photo 8: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W14114964
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Photo 10: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W14114964
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Photo 22: 14294 Winston Churchill Boulevard in Caledon: Rural Caledon House for sale : MLS®# W14114964
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Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
W14114964
Bedrooms:
4
Bathrooms:
3
Backing onto protected conservation land with no rear neighbours, this 2.43-acre Terra Cotta estate sits steps from the Cataract Trailway and Terra Cotta Conservation Area. Mature forest frames the property, while open lawn and established perennial beds create spaces to play, entertain and unwind. Garden paths wind past the perennials and beneath a charming arbour to quiet seating areas, with fresh blooms from spring through fall and blazing autumn colour in the forest beyond. The fully fenced backyard is a private resort. The heated saltwater pool is soft and gentle on skin and eyes, with no harsh chlorine smell, and the waterfall adds a soothing soundtrack to long summer afternoons. Heating extends the swim season from late spring into fall. The large patio offers room for dining, lounging and barbecues, all with the forest as your backdrop. Inside are 3,716 sq ft above grade plus a finished lower level, over 4,700 sq ft in all. The two-storey living room has a vaulted ceiling and a two-way wood-burning fireplace shared with the breakfast room. The kitchen features Miele appliances, including an oversized fridge, built-in oven, cooktop and flush-mount hood, and opens to a sunken family room that walks out to the yard. The main floor also has a formal dining room behind French doors, laundry with a walkout, and a 3-pc bath with heated floor and glass shower, steps from the pool. Upstairs, an open loft works as an office or reading nook, and four bedrooms include a primary suite with his-and-hers walk-in closets. The finished basement adds a large rec room plus a bonus room for a gym, guest room or office. Insulated double garage with epoxy floor. Morning coffee under the arbour, an evening swim beneath the trees: this is country living, minutes from town. Offers welcome Sunday, November 8 at 6 PM.
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:
Immedaite
Pool:
Inground, Salt
Link:
No
HST Applicable To Sale Price:
Included In
Taxes:
$2,025 / 2025
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, Bar Fridge
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
Energy Certification:
No
Green Property Information Statement:
No
Special Designation:
Unknown
Sewers:
Septic
Air Conditioning:
Central Air
Central Vacuum:
Yes
Seller Property Info Statement:
No
Laundry Level:
Main Level
Date Listed:
Oct 25, 2026
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Listed by RE/MAX HALLMARK REALTY LTD.
Data was last updated October 25, 2026 at 03:15 PM (UTC)
Area Statistics
Listings on market:
174
Avg list price:
$1,599,000
Min list price:
$449,900
Max list price:
$16,800,000
Avg days on market:
51
Min days on market:
0
Max days on market:
361
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.
DENNIS CHAN, BROKER
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.