1 / 50
← All Listings|For SaleMLS® W13224014

16927 Winston Churchill Boulevard

Caledon, Ontario

Also listed as 16927 Winston Churchill Blvd., Caledon, Ontario

$4,500,000
Listed June 2, 2026
5
Bedrooms
3
Bathrooms
N/A
Rooms
Single Family
Type
1006.4 x 597 FT
Lot
Detached Garage
Parking

Key Features

Cooling: Wall unit
Heating: Forced air, Propane
Basement: Partially finished, Partial
Parking: Detached Garage, Garage
Directions: Grange/Winston Churchill

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. (id:64869)

Property Details

Home Snapshot
MLS® NumberW13224014
StatusFor Sale
Property TypeSingle Family
Bedrooms5
Bathrooms3
Lot Dimensions1006.4 x 597 FT
Listed2026-06-02
Condo Fees & Taxes
Property Taxes$4,145
Lot, Views & Setting
DirectionsGrange/Winston Churchill
Construction & Systems
BasementPartially finished, Partial
HeatingForced air, Propane
CoolingWall unit
Water SourceDrilled Well
SewersSeptic System
Parking & Access
Parking Total25
Parking FeaturesDetached Garage, Garage
Listing Timeline
Last UpdatedJun 2, 2026, 2:15 a.m.

Frequently Asked Questions

Where is 16927 Winston Churchill Boulevard located?+

16927 Winston Churchill Boulevard is located in Caledon, ON (L7K1H9).

How much is 16927 Winston Churchill Boulevard?+

16927 Winston Churchill Boulevard is listed for sale at $4,500,000.

How many bedrooms and bathrooms does 16927 Winston Churchill Boulevard have?+

This home offers 5 bedrooms and 3 bathrooms.

What type of property is 16927 Winston Churchill Boulevard?+

It is a home.

What are the property taxes for 16927 Winston Churchill Boulevard?+

Annual property taxes are approximately $4,145.

Is there parking at 16927 Winston Churchill Boulevard?+

Yes — 16927 Winston Churchill Boulevard includes a 25-car garage.

How can I book a showing or learn more about 16927 Winston Churchill Boulevard, Caledon?+

Contact Barbara Beers and the Barbara Beers Real Estate team at +1-905-634-2335 or barbara@barbarabeers.com to book a private showing or request more details.

BB
Barbara Beers
Broker

Royal LePage® Burloak Real Estate Services

Mortgage Calculator

$4,500,000
5.25%
$900,000
Est. Monthly Payment
Principal & Interest only
$21,573

Estimate only. Does not include property taxes, insurance, or fees. Actual rates may vary. Contact us for personalized mortgage guidance.

Ask About This Property

Listing Source

Powered by REALTOR.ca

Listing Brokerage: ROYAL LEPAGE RCR REALTY

Advertised By: Royal LePage® Burloak Real Estate Services

MLS®, REALTOR®, and associated logos are trademarks of CREA.

Location

Similar

Similar Properties

City: Caledon

Price: $4,200,000 - $4,800,000

Type: Residential

Bedrooms: 5+

Bathrooms: 3+

[ SEE MORE ]
Close By

Nearby Listings

[ VIEW MORE ]