14294 Winston Churchill Boulevard, Caledon, ON

Caledon, Rural Caledon Hood
Winston Churchill Boulevard / King Street
4 Br | 3 Bath | 3500-5000 Sqft
$1,988,000 For Sale

Property Overview

  • Detached — 2-Storey
  • SqFt: | 3500-5000 Sqft
  • Lot Size: 232.35 x 416.18 Feet
  • Age: 31-50 Years
  • Basement: Finished, Full
  • Exterior: Stone, Vinyl Siding
  • Taxes: 7,275 / 2025
  • Zoning: n/a
  • MLS #: W14114964
  • Sewer: Septic
  • Heat Source: Propane , Forced Air

Property Description

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.

All Window Coverings and Screens, Including Hardware; Electric Light Fixtures and Ceiling Fans with Remotes; Water Softener; Water Heater; Closet Organizers; All Bathroom Shower Rods and Mirrors; Existing Microwave, Oven, Cooktop, Range Hood, Fridge, Dishwasher; All Garage Door Openers and Remotes; Clothes Washer and Clothes Dryer; Central Vacuum and all Related Equipment; TV Wall Mounts; Pool, Pump and all Related Equipment; Water Collection Barrels; Satellite Dish

Property Details

  • For: For Sale
  • Type: Detached
  • Style: 2-Storey
  • Lot: 232.35 x 416.18 Feet
  • Region: Peel
  • Hood: Rural Caledon
  • Zoning: n/a
  • Lot Irreg: Fronting on: West
  • Fronting On: West

Building Details

  • Age: 31-50 Years
  • Exterior: Stone, Vinyl Siding
  • Heat: Propane , Forced Air
  • A/C: Central Air
  • Interior Features: Auto Garage Door Remote, Central Vacuum, Propane Tank, Storage, Sump Pump, Water Heater Owned, Water Softener, Water Treatment, Bar Fridge
  • Pool: Inground, Salt
  • Sewer: Septic
  • Garage: Attached
  • Total Parking: 8.00
  • Driveway: Private Double

Property Interior

  • Sqft: 3500-5000 Sqft
  • Bed: 4
  • Bath: 3
  • Kitchen: 1
  • Family Room: No
  • Basement: Finished, Full
Rooms Details

Foyer

Main Level

5.67 x 3.41

Hardwood Floor, Double Closet, Vaulted Ceiling(s)

Dining Room

Main Level

3.89 x 4.04

Hardwood Floor, French Doors, Crown Moulding

Living Room

Main Level

3.89 x 4.78

Hardwood Floor, 2 Way Fireplace, Vaulted Ceiling(s)

Kitchen

Main Level

3.67 x 4.6

Hardwood Floor, Quartz Counter, Centre Island

Breakfast

Main Level

3.84 x 3.73

Hardwood Floor, 2 Way Fireplace, Large Window

Family Room

Main Level

5.82 x 5.82

Broadloom, Sunken Room, W/O To Pool

Laundry

Main Level

2.53 x 1.68

Tile Floor, W/O To Yard, Laundry Sink

Primary Bedroom

Second Level

6.41 x 5.83

Broadloom, Sunken Room, His and Hers Closets

Bedroom

Second Level

3.99 x 3.63

Broadloom, Closet, Window

Bedroom

Second Level

4.67 x 2.87

Broadloom, Closet, Window

Bedroom

Second Level

4.83 x 2.93

Broadloom, Closet, Window

Recreation

Basement Level

9.46 x 8.49

Broadloom, Fireplace, Above Grade Window

Exercise Room

Basement Level

7.71 x 4.09

Broadloom, Above Grade Window, Recessed Lighting

Property Listed by: RE/MAX HALLMARK REALTY LTD.
Virtual Tour: n/a

Home Valuation Estimate

What is 14294 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 3500-5000 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

Location

  • Address: 14294 Winston Churchill Boulevard
  • Neighborhood: Rural Caledon
  • Zip/Postal Code: L7C 3E8
  • Nearby Amenities: Fenced Yard, Greenbelt/Conservation, Lake/Pond, Wooded/Treed
Map preview placeholder for 14294 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 14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8, Caledon

Located at 14294 Winston Churchill Boulevard, Caledon, ON in Caledon (Rural Caledon neighbourhood), near Winston Churchill Boulevard / King Street. This freehold home offers Detached, ["2-Storey"], 4 bedrooms, 3 bathrooms and 3500-5000 sq.ft. (approx.) in a layout suited to everyday family living. Basement: Finished, Full • 8 parking spots • Garage: Attached • Heating: Propane Forced Air • Cooling: Central Air. Property taxes are approximately $7,275 for 2025. 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 aftern.

FAQs for 14294 Winston Churchill Boulevard, Caledon, ON , Rural Caledon , Caledon

What are the listing details for 14294 Winston Churchill Boulevard, Caledon, ON?
14294 Winston Churchill Boulevard, Caledon, ON is a Detached for sale in Caledon, in the Rural Caledon neighbourhood, Peel. The current list price is $1,988,000. MLS number: W14114964.
How many bedrooms and bathrooms does this home have?
14294 Winston Churchill Boulevard, Caledon, ON is listed as a Detached with a ["2-Storey"] style, featuring 4 bedroom(s) and 3 bathroom(s). The listed interior size range is 3500-5000 sq. ft..
What lot, basement, garage, or parking details are listed?
The lot size is listed as approximately 232.35 x 416.18 Feet. The basement is listed as: Finished, Full. Garage type: Attached. Total parking: 8 space(s).
What heating, cooling, and exterior details are shown?
Heating is listed as: Propane, Forced Air. Cooling is listed as: Central Air. Exterior/construction materials are listed as: Stone, Vinyl Siding.
Where is this property located?
14294 Winston Churchill Boulevard, Caledon, ON is located in the Rural Caledon neighbourhood of Caledon. The listed cross street is Winston Churchill Boulevard / King Street.
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 $7,275 / 2025. 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.