$4,500,000
16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
5 Beds
3 Baths
25 Parking
A Victorian reimagined, complete with a secret English garden. Just outside Belfountain, on nearly 15 acres of Caledon countryside, it is steeped in character and completely its own. The main house holds four bedrooms and three bathrooms, anchored by a bright central kitchen with the family room close at hand, cozy with its own fireplace. A breakfast nook looks out over perennial gardens and the pool beyond, with a screened Muskoka room just around the corner. The living room, with a dramatic architectural staircase as its focal point, overlooks the gardens and pond. A home you fall deeper into with every room. Waking up to gardens and pond, the main floor primary wing is a true sanctuary. A spa-like five piece ensuite, marble throughout, with soaker tub and steam shower. Upstairs, three additional bedrooms and a lovely five piece bath. Outside, the property opens into something rare. A 40 foot rectangular pool at the heart of the grounds, with a pool house and al fresco dining zone built for summer entertaining. A spring-fed pond with fountain and trails winding throughout. Heritage barn ruins that carry their own romance. (A family wedding was once held there, and the potential remains.) Once featured on the Caledon Garden Tour, the gardens include a spectacular Rhododendron forest. The outbuildings are exceptional. A detached two-car garage for the everyday and a heated three-bay garage for hobbies, toys, and your car collection, with one bay currently fitted as a sculpture studio. The garden cottage, a gym today complete with bathroom plus kitchen and laundry hookups, converts easily into a private one-bedroom suite for in-laws, older kids, or guests wanting their own world. A garden tea house overlooking the spring-fed pond, perfect for yoga or meditation. Minutes from Belfountain, close to great schools, skiing, hiking trails, golf, equestrian, local shops and restaurants. This is a home that holds everything.

Property Summary

Property Type Residential Freehold
Property Sub Type Detached
Transaction Type For Sale
Style 2-Storey
Approximate Age 100+
Bedrooms Above Grade 4
Bedrooms Below Grade 1
Bathrooms 3
Kitchens 2
Basement Partially Finished, Partial Basement
Exposure East
Possession TBD

Building

Building Type Detached
Square Footage 2500-3000
Exterior Brick, Wood
Foundation Stone
Roof Shingles
Heating Forced Air
Heat Source Propane
Cooling Wall Unit(s)
Fireplace Yes

Measurements

Lot Size 1006.41 x 597
Lot Size Units Feet
Frontage 1006.41
Depth 597
Total Living Area 2500-3000

Land

Address 16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9
City Caledon
Community Rural Caledon
County / Area Peel
Cross Street Grange/Winston Churchill
Sewer Septic
Water Source Drilled Well
Pool Inground
Parcel Number 142670224

Parking and Garage

Total Parking 25
Garage Spaces 5
Garage Type Detached
Parking Features Private

Taxes and Listing Info

List Price $4,500,000
Annual Taxes $4,145
Tax Year 2026
Status Active
Listing Date 2026-06-01T19:00:30Z
Updated 2026-06-01T19:24:23Z
MLS Number W13224014
Local Market Insight

What Buyers Should Know About 16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9

This editorial summary helps buyers look beyond the headline price and review the neighbourhood, transit, schools, rental demand, long-term value, and due-diligence items that often matter before booking a showing or submitting an offer.

Neighbourhood Analysis

16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9 is positioned in Rural Caledon, a part of Caledon where buyers should compare the street setting, nearby amenities, daily travel routes, and surrounding housing stock. For a 2-Storey, the strongest fit often depends on whether the location supports everyday routine as well as the numbers on paper.

School And Family Considerations

Families reviewing this Detached should confirm school boundaries directly with the local school boards before relying on listing notes. It is also worth checking walkability to parks, childcare, recreation centres, libraries, and community facilities because these details can influence both lifestyle value and future resale demand.

Transit And Access

The location should be assessed around commute patterns, access to Grange/Winston Churchill, public transit options, parking availability, and drive times to employment areas. A property with 25 parking and practical road access can appeal to buyers who need convenience without giving up neighbourhood quality.

Investment Potential

At $4,500,000, buyers should compare recent nearby sales, days on market, condition, lot utility, and the cost of future repairs or upgrades. The property shows 5 bedrooms, 3 bathrooms, basement details marked as Partially Finished, Partial Basement, and a lot size of 1006.41 x 597, all of which can affect value.

Rental Demand

If this property is being reviewed as a rental or investment, demand should be measured by bedroom count, transit access, employment access, nearby schools, parking, and the condition of the unit or home. In Caledon, rental appeal usually improves when a property is easy to maintain and simple for tenants to live in.

Local Attractions And Amenities

Buyers should look at grocery access, restaurants, trails, parks, shopping, medical services, and weekend amenities around Rural Caledon. These features do not always appear in the MLS data, but they can make a major difference in how the home feels after move-in and how future buyers compare it.

Builder, Condition, And Due Diligence

For resale homes, review renovations, permits, roof and mechanical age, exterior condition, inclusions, and rental items. For condo or newer properties, review building history, maintenance fees, reserve fund information, rules, amenities, and future cost exposure. A showing and document review should confirm anything not visible in the listing.

Nearby Infrastructure

Infrastructure matters because transit improvements, road projects, schools, parks, commercial growth, and employment nodes can change how an area performs over time. For 16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9, buyers should check municipal plans, nearby construction, zoning context, and future projects that may affect enjoyment or resale value.

This section is informational only. Buyers should verify schools, measurements, rental rules, taxes, zoning, and property condition with the appropriate professionals before making a decision.

Listing data is provided through PropTx/MLS data services and is deemed reliable but not guaranteed. Listings are subject to change without notice.