$4,200,000
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16927 Winston Churchill Boulevard, Caledon, ON L7K1H9

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5 Beds
3 Baths
- Sq Ft

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:58753)

Listing By: JADE SKUCE - ROYAL LEPAGE RCR REALTY
Source: CREA #W13224014 Listing provided courtesy of Canadian Real Estate Association
  • MLS® W13224014
  • Date Listed06/01/2026
  • Days on Realty 120 Days
  • Bedrooms 5
  • Bathrooms 3 baths
  • Lot Size -
  • Sewer Septic Tank
  • Property Type Single Family Residence
  • Water Well

Interior Features

  • Appliances All, Refrigerator, Water softener, Water Treatment, Window Coverings
  • Cooling Wall unit
  • Heating Forced air, Propane

Exterior / Lot Features

  • Roof -
  • Lot Size Acres -
  • Lot Size SQFT -
  • Lot Features Wooded area, Guest Suite

Directions

Grange/Winston Churchill

Sales & Tax History

Source: Public Records

Local Neighborhood Highlights for L7K1H9

Discover key demographics, population statistics, and environmental insights for the Caledon, ON area.

Walkability in ON / L7K1H9

Source: Walk Score

8/100

Car-Dependent

Walk Score ®

0/100

Minimal Transit

Transit Score ®

23/100

Bikable

Bike Score ®

Overview

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 6/100, Transit Score: 0/100, Bike Score: 22/100.

Points of Interest near 16927 WINSTON CHURCHILL BOULEVARD, Caledon, ON L7K1H9

Frequently Asked Questions for 16927 WINSTON CHURCHILL BOULEVARD

Source: Realty.com

16927 WINSTON CHURCHILL BOULEVARD, Caledon, ON L7K1H9 in Caledon, ON L7K1H9 is a single family residence listed at $4,200,000. Highlights include 5 bedrooms, 3 bathrooms. Realty.ca has 50 photos, sales history, school insights, and mortgage tools for this listing.

Realty.com has 50 photos of 16927 WINSTON CHURCHILL BOULEVARD.

The full address for this home is 16927 WINSTON CHURCHILL BOULEVARD, Caledon, ON L7K1H9.

16927 WINSTON CHURCHILL BOULEVARD has been listed on Realty.com since Mon June 01, 2026

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

The average walkability score in the surrounding area is Walk Score: 6/100, Transit Score: 0/100, Bike Score: 22/100.

This content last refreshed on 2026-09-29 23:41:36. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.