For Sale · Caledon · Single Family

$1,900,000

14451 WINSTON CHURCHILL BOULEVARD, Caledon

Beds

4 (1 half)

Baths

About This Home

The details.

Escape The Ordinary. Discover Your Private Estate In Prestigious South Caledon Where Sophisticated Country Living Meets Modern Luxury. Nestled On A Breathtaking One-Acre Lot (150X300 Ft), This Newly Extended 4-Bedroom, Over 3,600 Sq Ft Masterpiece Backs Onto A Ravine With Terra Cotta Conservation At Your Doorstep, Privacy And Nature Embrace You At Every Turn. Extensively Renovated Top To Bottom In 2024-All With Permits-This Home Features New Plumbing, Electrical With 200 Amp Service, Septic, Furnace, A/C, Generator, Roof, Doors & Windows Throughout. Designed For Both Grand Entertaining And Intimate Family Living, The Open-Concept Kitchen, Dining & Family Rooms Flow Seamlessly Together. The Brand-New Chef's Kitchen Showcases A Large Island, Stone Counters, Matching Backsplash, And Top-Of-The-Line Stainless Steel Appliances. Large Windows Fill The Home With Natural Light. The Upper-Level Retreat Showcases Two Luxurious Primary Suites. The First Offers A Fireplace, Juliet Balcony Overlooking The Greenspace, Dual Walk-In Closets, And A Spa-Inspired Ensuite Complete With Heated Floors, A Soaker Tub, And An Oversized Glass Shower. The Second Includes Its Own Fireplace, Walk-In Closet, And Heated Ensuite Floors. Ceiling Fans Throughout The Bedrooms And Motorized Blinds Provide Year-Round Comfort, While Convenient Second-Floor Laundry Adds Everyday Ease. Attached Double Garage Plus An Incredible Detached 6-Car Garage/Workshop Offer Endless Possibilities For Car Collectors, Hobbyists, Home Gyms, Or Dream Workspaces. Enjoy A Large Gazebo, Fire Pit Area, And An Unmatched Outdoor Lifestyle. A Rare Opportunity For Families Or Anyone Seeking Space, Privacy, And Refined Country Living Near Town Amenities. (id:66635)

Summarizing the highlights...

MLS® W13445462Listing courtesy of RE/MAX REALTY SPECIALISTS INC.View on map Street view

Property Details

Facts & features.

Property type: Single Family
Ownership: Freehold
Storeys: 2
Parking: 25 spaces
Listed on: 2026-06-15
Days on market: 30
MLS number: W13445462
Data source: Toronto Regional Real Estate Board

July Value

What this home is worth.

Calculating a July Value estimate...

Realtor Recommended

JULY advisors for this home.

Bart Pukacz
Real Estate Advisor
Residential, Investment Properties, Presale Condos
Profile 604.721.1439
Han Lee
Real Estate Advisor
Residential, Investment Properties, Luxury Properties
Profile
Iñaki Sarmiento
Real Estate Advisor
Residential, Investment Properties
Profile 778.954.6254

My Notes

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Location

Where it sits.

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Run The Numbers

Mortgage and cash flow.

Mortgage calculator.

Home priceDown payment20%Rate (%)Amortization

Monthly mortgage payment

$8,886

$1,520,000 financed over 25 years at 5%. For guidance only, not a quote or approval.

Cash flow analysis.

Property tax / moMaintenance / moRental income / mo

Monthly cost (mortgage + tax + maintenance)

$8,886

Cash flow

-$8,886

Estimates for education only. Talk to a JULY advisor for real numbers on this home.

Caledon right now

Active listings

New this week

$1,298,000

Median asking price

Live snapshot from the MLS® feed. Sold-price history and trend charts arrive with our VOW data feed.

The Neighbourhood

Living in Caledon.

Household and demographic stats for Caledon, from the Statistics Canada 2021 Census.

76,581
Population (2021): 40.8
Median age: 23,700
Households: 3.2
Avg household size: 89.4%
Home ownership: $133,000
Median household income

Caledon market trends

Source: Statistics Canada 2021 Census, Caledon, Town, Ontario.

Schools

Nearby schools.

K-12 schools closest to this home, with straight-line distances.

Wildbeasts Outdoor Education
independent · elementary
5.0 km

Source: Statistics Canada, Open Database of Educational Facilities. Distances are straight-line, not walking routes. Catchment boundaries change; always confirm with the school district.

Similar Homes

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Rental Market

Renting nearby.

Active rentals close to this home, for rent-versus-buy context and investors sizing up cash flow.

Price on request / month
18831 WINSTON CHURCHILL BOULEVARD, Caledon
2 bed · 1 bath

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Listing information is provided courtesy of the Canadian Real Estate Association's Data Distribution Facility (DDF®) and is deemed reliable but is not guaranteed accurate by JULY Realty or CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos identify professional services rendered by REALTOR® members of CREA to effect the purchase, sale and lease of real estate as part of a cooperative selling system. The trademarks REALTOR®, REALTORS® and the REALTOR® logo are controlled by CREA and identify real estate professionals who are members of CREA.