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.
About this home
Photos of 14294 Winston Churchill Boulevard
Facts and features of 14294 Winston Churchill Boulevard
| Type | Detached |
|---|---|
| Style | 2-Storey |
| Bedrooms | 4 |
| Bathrooms | 3 |
| Size | 3500-5000 sq ft |
| Lot | 232.35 x 416.18 Feet |
| Parking | 8 |
| Garage | Attached |
| Heating | Forced Air |
| Cooling | Central Air |
| Basement | Finished, Full |
| Exterior | Stone, Vinyl Siding |
| Age | 31-50 |
| Taxes | $7,275 (2025) |
| Days on market | 5 |
| Listing brokerage | RE/MAX HALLMARK REALTY LTD. |
Rooms
13 rooms, with sizes
| Room | Level | Size | Features |
|---|---|---|---|
| Family Room | Main | 19′ 1″ × 19′ 1″ 5.82 × 5.82 m | broadloom, sunken room, w/o to pool |
| Foyer | Main | 18′ 7″ × 11′ 2″ 5.67 × 3.41 m | hardwood floor, double closet, vaulted ceiling(s) |
| Bedroom | Second | 15′ 10″ × 9′ 7″ 4.83 × 2.93 m | broadloom, closet, window |
| Exercise Room | Basement | 25′ 4″ × 13′ 5″ 7.71 × 4.09 m | broadloom, above grade window, recessed lighting |
| Dining Room | Main | 12′ 9″ × 13′ 3″ 3.89 × 4.04 m | hardwood floor, french doors, crown moulding |
| Laundry | Main | 8′ 4″ × 5′ 6″ 2.53 × 1.68 m | tile floor, w/o to yard, laundry sink |
| Primary Bedroom | Second | 21′ 0″ × 19′ 2″ 6.41 × 5.83 m | broadloom, sunken room, his and hers closets |
| Breakfast | Main | 12′ 7″ × 12′ 3″ 3.84 × 3.73 m | hardwood floor, 2 way fireplace, large window |
| Living Room | Main | 12′ 9″ × 15′ 8″ 3.89 × 4.78 m | hardwood floor, 2 way fireplace, vaulted ceiling(s) |
| Recreation | Basement | 31′ 0″ × 27′ 10″ 9.46 × 8.49 m | broadloom, fireplace, above grade window |
| Bedroom | Second | 15′ 4″ × 9′ 5″ 4.67 × 2.87 m | broadloom, closet, window |
| Kitchen | Main | 12′ 0″ × 15′ 1″ 3.67 × 4.6 m | hardwood floor, quartz counter, centre island |
| Bedroom | Second | 13′ 1″ × 11′ 11″ 3.99 × 3.63 m | broadloom, closet, window |
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14294 Winston Churchill Boulevard
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MLS® W14114964 Data source: PropTx Listed October 25, 2026