16927 Winston Churchill Boulevard

ActiveCaledon · Rural Caledon66 days on marketMLS® W13224014

$4,500,000

$1,800 / sq ft

Bedrooms5

Bathrooms3

Interior2,500 sq ft

TypeSingle Family Home

ListingFor Sale

Days on Market66

About this property

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.

Features & finishes

View

Fireplace

Air Conditioning

Basement

Property details

MLS® Number	W13224014
Status	Active
Listing Type	For Sale
Property Type	Single Family Home
Interior Size	2,500 sq ft
Beds / Baths	5 bed · 3 bath
Neighbourhood	Rural Caledon
City	Caledon
Postal Code	L7K 1H9
Province	ON
Listed Date	June 1, 2026
Days on Market	66
Price per Sq Ft	$1,800
Brokerage	ROYAL LEPAGE RCR REALTY