19919 Winston Churchill Boulevard
About this property
Nestled in the heart of Caledon, this sprawling 23.16-acre country estate offers a total of 3676 sq ft of living space, exuding the charm of a raised side-spilt. Upon entering, you're greeted by an open-concept gourmet kitchen with an eat-in breakfast space, seamlessly flowing into the living and dining rooms, bathed in natural light. The breakfast room leads to an oversized terrace overlooking the backyard oasis and inground pool. A wood stove in the living room and custom-built shelving add to the cozy atmosphere. Ascend half a flight to discover three spacious bedrooms, including a primary suite with ensuite bath. Large- vast family room spanning the length of the house, with potential to be divided into two rooms or a second primary suite with ensuite. Access to the mudroom, garage, and backyard oasis is available. At the lower level, a full walk-out to the outdoor pool and cabana. Here, a large rec room with a 3-piece washroom offers potential for conversion into an apartment or fourth bedroom. Entertainers dream backyard as it features a Cabana, a large pond with an island for fishing and cleared land to the north with three paddocks. *** An approx. 1500 sqft workshop, features heat and hydro*** . With ample land for trails, hiking, farming, or creating a mini-farm, this estate invites you to embrace the serenity and versatility of country living at its finest.
Features & finishes
Property details
| MLS® Number | W9511276 |
| Status | Sold |
| Listing Type | For Sale |
| Property Type | Single Family Home |
| Interior Size | 2,500 sq ft |
| Beds / Baths | 3 bed · 4 bath |
| City | Caledon |
| Postal Code | L7K 1J6 |
| Province | ON |
| Listed Date | February 1, 2026 |
| Brokerage | RE/MAX SPECIALISTS TEAM SUKHVINDER |
Location
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