
Welcome to this remarkable 2-Storey detached located in the coveted neighborhood of Rural Caledon. Expertly crafted featuring premium stone and vinyl siding construction, this residence presents an exceptional opportunity offered at $1,988,000 to acquire a beautiful home in a highly sought-after setting. Designed for both comfortable daily living and elegant entertaining, the layout maximizes natural light, functional flow, and lifestyle utility.
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.
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This detached home located at 14294 Winston Churchill Boulevard, Caledon is currently for sale and has been available for 7 days. This property is listed at $1,988,000 with an estimated mortgage of $6,617* per month. It has 4 beds, 3 bathrooms, and is 3500-5000 square feet. 14294 Winston Churchill Boulevard, Caledon is in the Rural Caledon neighborhood.
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* Estimated mortgage assumes a 30% down payment, 4.00% interest rate, and 30-year amortization.Yes! Featuring 4 bedrooms and 3 bathrooms, this home offers ample space and comfort for growing families in Rural Caledon, Caledon.
Growing families needing multi-bedroom flexibility and space in Rural Caledon, Caledon.
None listed
No historical data available for this property.
This could be the first listing for this address.
If you are looking for a house in Caledon or researching Caledon real estate for sale, this 4-bedroom detached at 14294 Winston Churchill Boulevard, Caledon, ON offers an exceptional opportunity to buy a home in Caledon, Ontario. Whether you are a first-time Caledon home buyer or comparing active Caledon MLS® homes for sale, working with a dedicated Caledon buyer agent ensures you receive priority showing access, unrepresented buyer protection, and aggressive price negotiation.
Browse all verified Caledon real estate listings, compare active Caledon houses for sale, and view brand new MLS® inventory before it hits the open market.
Under Ontario REBBA/TRESA regulations, the listing brokerage is legally bound to the seller's financial interests. Work with an experienced Caledon realtor & real estate broker who represents you 100%—at zero cost to you as a buyer.
Estimated mortgage: $6,617*/month*. Estimated Ontario Land Transfer Tax: $36,235. First-time Caledon home buyers may qualify for up to $8,475 in rebates.
The current listing price for 14294 Winston Churchill Boulevard, Caledon, ON in Rural Caledon, Caledon is $1,988,000.
This property features 4 bedrooms and 3 bathrooms across approximately 3500-5000 sqft.
14294 Winston Churchill Boulevard, Caledon, ON is a Detached (2-Storey) featuring a Finished, Full basement.
Key property features include: Fenced Yard, Greenbelt/Conservation, Lake/Pond, Wooded/Treed.
Interior highlights include: Auto Garage Door Remote, Central Vacuum, Propane Tank, Storage, Sump Pump, Water Heater Owned, Water Softener, Water Treatment, Bar Fridge.
Security features include: Security System, Monitored.
Yes, this property offers parking space for 8.0 vehicles (Attached).
Heating is provided via Propane and cooling via Central Air.
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Rural Caledon, Caledon
5 assaults (45.0/100k)
4 B&E (40.0/100k)
7 thefts (45.0/100k)
Improving vs previous year
Formula: (Annual Occurrences / Population) Ă— 100,000. This standard policing calculation normalizes incident frequencies across different population sizes, allowing accurate safety comparisons between quiet residential pockets and dense urban centres.
Disclaimer: Crime and safety analytics are compiled from official municipal and regional police open data records for general consumer informational and demographic research purposes only. Data is deemed reliable but is not guaranteed and does not constitute a legal representation or guarantee of future safety.
Data-driven valuation for 14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8
Based on 0 recent similar sales in the pocket.
Properties in this area are selling at a steady pace.
Calculate your monthly payment, minimum downpayment, and land transfer taxes for this home in Caledon.
About Purchasing a Home in Caledon, ON
For a property listed at $1,988,000 in Caledon, the legal minimum down payment is $397,600 under current Canadian banking regulations. This calculation applies a 5% requirement on the first $500,000, 10% on the next $499,999, and a flat 20% on any amount exceeding $1,000,000.
Additionally, buyers in Ontario must budget for the Provincial Land Transfer Tax, which is estimated at $36,235 for this transaction. As this listing is in Caledon (outside the City of Toronto), no additional municipal land transfer tax is levied, resulting in total estimated land transfer taxes of $36,235.
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Disclaimer: AI Insights are generated by an automated system and should be used for informational purposes only. While we strive for accuracy using current market data and deep-learning models, these assessments do not constitute professional real estate, legal, or financial advice. All property values, predictions, and scores are estimates. We strongly recommend verifying all property details and conducting independent due diligence with a licensed professional before making any purchase decisions.
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