16927 Winston Churchill Boulevard, Caledon, ON

Caledon, Rural Caledon Hood
Grange/Winston Churchill
4+1 Br | 3 Bath | 2500-3000 Sqft
$4,500,000 For Sale

Property Overview

  • Detached — 2-Storey
  • SqFt: | 2500-3000 Sqft
  • Lot Size: 1006.41 x 597.00 Feet
  • Age: 100+ Years
  • Basement: Partially Finished, Partial Basement
  • Exterior: Brick, Wood
  • Taxes: 4,145 / 2026
  • Zoning: n/a
  • MLS #: W13224014
  • Water: Drilled Well
  • Sewer: Septic
  • Heat Source: Propane , Forced Air

Property Description

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.

All appliances, electrical light fixtures, and window coverings. UV system, water softener. Pool accessories, pool fridge and pool sound system. EV charger.

Property Details

  • For: For Sale
  • Type: Detached
  • Style: 2-Storey
  • Lot: 1006.41 x 597.00 Feet
  • Region: Peel
  • Hood: Rural Caledon
  • Zoning: n/a
  • Lot Irreg: Fronting on: East
  • Fronting On: East

Building Details

  • Age: 100+ Years
  • Exterior: Brick, Wood
  • Heat: Propane , Forced Air
  • A/C: Wall Unit(s)
  • Interior Features: In-Law Capability, Primary Bedroom - Main Floor, Guest Accommodations, Water Treatment, Generator - Partial
  • Pool: Inground
  • Water: Drilled Well
  • Sewer: Septic
  • Garage: Detached
  • Total Parking: 25.00
  • Driveway: Private

Property Interior

  • Sqft: 2500-3000 Sqft
  • Bed: 4 +1
  • Bath: 3
  • Kitchen: 1 +1
  • Family Room: No
  • Basement: Partially Finished, Partial Basement
Property Listed by: ROYAL LEPAGE RCR REALTY
Virtual Tour: https://youtu.be/opuhU3Lcp_I

Home Valuation Estimate

What is 16927 Winston Churchill Boulevard, Caledon, ON worth in today’s Rural Caledon, Caledon market?

This HomeZira valuation preview helps buyers and sellers think through the asking price for this 4-bedroom Detached with 2500-3000 sq. ft. in Rural Caledon, Caledon. The full estimate reviews the property’s location, home type, bedroom count, size range, age, and nearby comparable market activity after sign-in.

Property-specific estimate See a valuation range built around this listing’s local profile.
Comparable market context Review how similar nearby homes help frame value.
Buyer and seller guidance Use the estimate as a starting point before an offer or pricing decision.
Sign in to view the full valuation estimate.
Log in to view valuation Create free account

Similar Recently Sold Properties

Compare 16927 Winston Churchill Boulevard, Caledon, ON with nearby homes that recently sold in the same market area.

Similar sold property preview
Sold recently

Sold price locked

List price available after sign-in

Similar sold home nearby

Hood, city and sold details available after sign-in
  • Beds
  • Baths
  • SqFt.
Type: Similar property type
DOM: Available after sign-in
Similar sold property preview
Sold recently

Sold price locked

List price available after sign-in

Similar sold home nearby

Hood, city and sold details available after sign-in
  • Beds
  • Baths
  • SqFt.
Type: Similar property type
DOM: Available after sign-in
Similar sold property preview
Sold recently

Sold price locked

List price available after sign-in

Similar sold home nearby

Hood, city and sold details available after sign-in
  • Beds
  • Baths
  • SqFt.
Type: Similar property type
DOM: Available after sign-in

Sign in to view recent similar sold properties

View recently sold comparable homes, including sold prices, list prices, sale dates, and property details.

Log in Register

Location

  • Address: 16927 Winston Churchill Boulevard
  • Neighborhood: Rural Caledon
  • Zip/Postal Code: L7K 1H9
  • Nearby Amenities: Lake/Pond, Wooded/Treed
Map preview placeholder for 16927 Winston Churchill Boulevard, Caledon, ON, Canada
Loads interactive map with Street View + zoom.

Mortgage Calculator

Mortgage Amount:$0
Monthly Mortgage (est.):$0
Payment (per period): $0
Estimated Monthly Total*$0
*Monthly total = monthlyized mortgage payment + taxes/12 + condo fee.

About 16927 Winston Churchill Boulevard, Caledon, ON L7K 1H9, Caledon

Located at 16927 Winston Churchill Boulevard, Caledon, ON in Caledon (Rural Caledon neighbourhood), near Grange/Winston Churchill. This freehold home offers Detached, ["2-Storey"], 4 bedrooms, 3 bathrooms, 8 total rooms and 2500-3000 sq.ft. (approx.) in a layout suited to everyday family living. Basement: Partially Finished, Partial Basement • 25 parking spots • Garage: Detached • Heating: Propane Forced Air • Cooling: Wall Unit(s). Property taxes are approximately $4,145 for 2026. 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 sanct.

FAQs for 16927 Winston Churchill Boulevard, Caledon, ON , Rural Caledon , Caledon

What are the listing details for 16927 Winston Churchill Boulevard, Caledon, ON?
16927 Winston Churchill Boulevard, Caledon, ON is a Detached for sale in Caledon, in the Rural Caledon neighbourhood, Peel. The current list price is $4,500,000. MLS number: W13224014.
How many bedrooms and bathrooms does this home have?
16927 Winston Churchill Boulevard, Caledon, ON is listed as a Detached with a ["2-Storey"] style, featuring 4+1 bedroom(s) and 3 bathroom(s). The listed interior size range is 2500-3000 sq. ft..
What lot, basement, garage, or parking details are listed?
The lot size is listed as approximately 1006.41 x 597.00 Feet. The basement is listed as: Partially Finished, Partial Basement. Garage type: Detached. Total parking: 25 space(s).
What heating, cooling, and exterior details are shown?
Heating is listed as: Propane, Forced Air. Cooling is listed as: Wall Unit(s). Exterior/construction materials are listed as: Brick, Wood .
Where is this property located?
16927 Winston Churchill Boulevard, Caledon, ON is located in the Rural Caledon neighbourhood of Caledon. The listed cross street is Grange/Winston Churchill.
What information is available on this public listing page?
The public listing page shows current active listing information, property photos, room details when available, map location, listed price, property features, and contact options. Annual taxes are listed as $4,145 / 2026. Valuation tools and similar sold-property previews are available after sign-in where applicable, without displaying sold data in this public FAQ.

FAQ content is based on current active listing fields shown on this page. Sold prices, sold comparables, and VOW-only details are not included in this public FAQ.