14294 Winston Churchill Boulevard, photo 1

For sale Rural Caledon, Caledon, ON

14294 Winston Churchill Boulevard

List price
$1,988,000
Sq ft
3500-5000
Bedrooms
4
Bathrooms
3

About this home

Backing onto protected conservation land with no rear neighbours, this 2.43-acre Terra Cotta estate sits steps from the Caledon 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 pool and patio area make your backyard 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. Ontario's Conservation Land Tax incentive program reduces taxable property amount by 1.39 acres from the total area of 2.42 acres.

Photos of 14294 Winston Churchill Boulevard

Facts and features of 14294 Winston Churchill Boulevard

Key facts
TypeDetached
Style2-Storey
Bedrooms4
Bathrooms3
Size3500-5000 sq ft
Lot232.35 x 416.18 Feet
Parking8
GarageAttached
HeatingForced Air
CoolingCentral Air
BasementFinished, Full
ExteriorStone, Vinyl Siding
Age31-50
Taxes$7,275 (2025)
Days on market5
Listing brokerageRE/MAX HALLMARK REALTY LTD.

Rooms

13 rooms, with sizes

RoomLevelSizeFeatures
Family Room Main 19′ 1″ × 19′ 1″ broadloom, sunken room, w/o to pool
Foyer Main 18′ 7″ × 11′ 2″ hardwood floor, double closet, vaulted ceiling(s)
Bedroom Second 15′ 10″ × 9′ 7″ broadloom, closet, window
Exercise Room Basement 25′ 4″ × 13′ 5″ broadloom, above grade window, recessed lighting
Dining Room Main 12′ 9″ × 13′ 3″ hardwood floor, french doors, crown moulding
Laundry Main 8′ 4″ × 5′ 6″ tile floor, w/o to yard, laundry sink
Primary Bedroom Second 21′ 0″ × 19′ 2″ broadloom, sunken room, his and hers closets
Breakfast Main 12′ 7″ × 12′ 3″ hardwood floor, 2 way fireplace, large window
Living Room Main 12′ 9″ × 15′ 8″ hardwood floor, 2 way fireplace, vaulted ceiling(s)
Recreation Basement 31′ 0″ × 27′ 10″ broadloom, fireplace, above grade window
Bedroom Second 15′ 4″ × 9′ 5″ broadloom, closet, window
Kitchen Main 12′ 0″ × 15′ 1″ hardwood floor, quartz counter, centre island
Bedroom Second 13′ 1″ × 11′ 11″ broadloom, closet, window

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MLS® W14114964 Data source: PropTx Listed October 25, 2026