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14451 Winston Churchill Boulevard

Rural Caledon / Caledon, ON L7C 1S7

ActiveFor Sale
4 Beds
4 Baths
3,500 Sq Ft
Single Family Home
Virtual Tour Available

About This Property

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.

Property Details

StatusActive
Property TypeSingle Family Home
Listing TypeFor Sale
Interior Size3,500 sq ft
Bedrooms4
Bathrooms4
Postal CodeL7C 1S7
Last UpdatedAug 8, 2026 · 5:21 p.m.

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Features & Amenities

  • View
  • Fireplace
  • Air Conditioning
  • Basement

TRREB MLS® Attribution

MLS® W13445462

Listed by RE/MAX REALTY SPECIALISTS INC.

The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA. The trademarks REALTOR®, REALTORS® and the REALTOR® logo are controlled by CREA and identify real estate professionals who are members of CREA. Listing data provided by the Toronto Regional Real Estate Board (TRREB). The information contained herein is from sources believed to be reliable but is not guaranteed. Information deemed reliable but not guaranteed accurate by TRREB or Team Filipe / RE/MAX.

$1,900,000

asking price

MLS®W13445462
TypeSingle Family Home
CityCaledon
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Team Filipe · RE/MAX · (647) 210-6070

Mortgage Estimate

Est. Monthly Payment

$9,278

/month · $1,520,000 mortgage

Down Payment20% — $380,000
Interest Rate5.5%

Amortization

Total Interest

$1,263,385

Total Cost

$2,783,385

Estimate only. Based on Canadian semi-annual compounding, 25-yr amortization at 5.5%.

Full Mortgage Calculator →

Listed By

RE/MAX REALTY SPECIALISTS INC.