Gallery
Open House: Sun - Nov 1 4:00 - 6:00 PM
50
$1,988,000

CindySEZ

$1,819,976

CindySEZ

$1,819,976

14294 Winston Churchill Boulevard, Caledon
Rural Caledon
4 Beds
3 Baths

MLS#W14114964

14294 Winston Churchill Boulevard, Caledon

$1,988,000

Rural Caledon
4 Beds
3 Baths

MLS#W14114964

CindySEZ

$1,819,976

CindySEZ

$1,819,976

Home DetailsFeaturesExterior FeatureRoomsSales History

Backing onto protected conservation land with no rear neighbours, this 2.43-acre Terra Cotta estate sits steps from the Caledon Trailway and Terra Cotta Conservation Area. Mature forest frames the property, while open lawn and established perennial beds create spaces to play, entertain and unwind. Garden paths wind past the perennials and beneath a charming arbour to quiet seating areas, with fresh blooms from spring through fall and blazing autumn colour in the forest beyond. The fully fenced pool and patio area make your backyard a private resort. The heated saltwater pool is soft and gentle on skin and eyes, with no harsh chlorine smell, and the waterfall adds a soothing soundtrack to long summer afternoons. Heating extends the swim season from late spring into fall. The large patio offers room for dining, lounging and barbecues, all with the forest as your backdrop. Inside are 3,716 sq ft above grade plus a finished lower level, over 4,700 sq ft in all. The two-storey living room has a vaulted ceiling and a two-way wood-burning fireplace shared with the breakfast room. The kitchen features Miele appliances, including an oversized fridge, built-in oven, cooktop and flush-mount hood, and opens to a sunken family room that walks out to the yard. The main floor also has a formal dining room behind French doors, laundry with a walkout, and a 3-pc bath with heated floor and glass shower, steps from the pool. Upstairs, an open loft works as an office or reading nook, and four bedrooms include a primary suite with his-and-hers walk-in closets. The finished basement adds a large rec room plus a bonus room for a gym, guest room or office. Insulated double garage with epoxy floor. Morning coffee under the arbour, an evening swim beneath the trees: this is country living, minutes from town. Offers welcome Sunday, November 8 at 6 PM. Ontario's Conservation Land Tax incentive program reduces taxable property amount by 1.39 acres from the total area of 2.42 acres.

Home Details

Home Details

  • Category

  • Residential

  • Status

  • New

  • Days on Market

  • 5 Days

  • List date

  • 10/23/2026

  • Listing Updated On

  • 10/27/2026

  • Taxes / Year

  • $7,275.21 / 2025

  • Style

  • Detached

  • Type

  • 2-Storey

  • Year Built

  • 31-50

  • Lot Size

  • 2.22 Acres

Features

Features

Beds & Baths

  • Total Beds

  • 4

  • Baths

  • 3

Heating & Cooling

  • Heating Type

  • Forced Air

  • Air Conditioning

  • Central Air

  • Number of Fireplaces

  • 2

Parking & Garage

  • Total Parking

  • 10

  • Number of Garage Spaces

  • 2

Basement

  • Desc

  • Finished, Full

Appliances & Equipment

Appliances & Equipment

Exclusions

Ping Pong Table; Outdoor Fireplace
Patio Furniture
Accessories
Hammock and Stand
Neighbourhood Influences

Neighbourhood Influences

Fenced Yard
Greenbelt/Conservation
Lake/Pond
Wooded/Treed
Exterior Feature

Exterior Feature

Construction

  • Year Built

  • 31-50

Lot

  • Acres

  • 2.22 Acres

  • Frontage

  • 232 Ft

  • Depth

  • 416 Ft

Construction Details

  • Foundation Type

  • Concrete Block

  • Roof Material

  • Shingles

  • Exterior

  • Stone, Vinyl Siding

Water & Sewer

  • Sewer

  • Septic

Legal

  • Brokerage

  • Re/Max Hallmark Realty Ltd.

  • Legal Description

  • Pt Lt 29 Con 6 Whs Chinguacousy , Pt 1, 43r13519 ; Caledon

Rooms

Rooms

Main Floor

  • Family Room

  • 5.82 / 5.82

  • Foyer

  • 3.41 / 5.67

  • Dining Room

  • 4.04 / 3.89

  • Laundry

  • 1.68 / 2.53

  • Breakfast

  • 3.73 / 3.84

  • Living Room

  • 4.78 / 3.89

  • Kitchen

  • 4.6 / 3.67

Second

  • Bedroom

  • 2.93 / 4.83

  • Primary Bedroom

  • 5.83 / 6.41

  • Bedroom(2)

  • 2.87 / 4.67

  • Bedroom(3)

  • 3.63 / 3.99

Lower Floor

  • Exercise Room

  • 4.09 / 7.71

  • Recreation

  • 8.49 / 9.46

Sales History

Sales History

Active

(5 days on market)

Viewing now

New

2026-10-23

Listed For Sale

$1,988,000

MLS# W14114964

1900-06-21

0

View

1900-06-21

1900-06-21

Listed For Sale

$0

MLS# W12591338

1900-06-21

0

View

1900-06-21

1900-06-21

Listed For Sale

$0

MLS# W12352229

14294 Winston Churchill Boulevard
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