Front of 14451 Winston Churchill Boulevard
14451 Winston Churchill BoulevardCaledon (Rural Caledon)
Sold
1/49
Ontario Real Estate › Caledon › Rural Caledon
Front of 14451 Winston Churchill Boulevard
14451 Winston Churchill BoulevardCaledon (Rural Caledon)
Sold
See all 49 photos
DetachedMLS W13445462
Sold for:Sold Oct 21, 2026
4 Bedrooms
4 Bathrooms
8 Garage
3.5K~5K Sq.Ft.
150.17 x 300.48 ft Lot
$4,705 Tax/yr

Property history

1 saleSign in to see sold prices

This home has sold. It is no longer available.

Property not available for sale or for rent.

See similar homes for saleFree Home EvaluationHow Much Is My Home Worth?Sell with HOMEHHOMEH One: full-service selling for a 1% listing fee. The buyer's agent commission is separate.

Contact agent

Leave your name and number. A HOMEH agent calls you back.

Ask about this home

A HOMEH agent will answer your questions about this home.
Ask a question

Ask HOMEH

Ask about this home

About this home

14451 Winston Churchill Boulevard, Caledon

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.

Carpet FreeCountertop RangeGenerator - FullPropane TankWater HeaterWater Softener

Facts & features

TypeDetached
Style2-storey
Size3.5K~5K Sq.Ft.
Lot150.17 x 300.48 ft
Tax$4,705 (2025)
HeatingForced air, propane
CoolingCentral air
BasementCrawl space
Parking17 drive
WaterWell
FireplaceYes, wood stove

Ask about this home

A HOMEH agent will answer your questions about this home.

Ask a question

Rooms

9 rooms · 4 bathrooms
Main floor5 rooms
  • Mud room10′ × 6′60 sq.ft.
  • Living room17′5″ × 11′1″194 sq.ft.
  • Kitchen9′9″ × 9′88 sq.ft.
  • Family room37′4″ × 11′5″425 sq.ft.
  • Dining room37′4″ × 11′5″425 sq.ft.
Second floor4 rooms
  • Bedroom 39′9″ × 9′3″90 sq.ft.
  • Bedroom 216′7″ × 12′9″211 sq.ft.
  • Bedroom 49′8″ × 8′77 sq.ft.
  • Primary bedroom20′8″ × 15′8″325 sq.ft.
Bathrooms4
5-pcSecond3-pcSecond3-pcSecond2-pcMain
Thinking of selling your home?See what your home is worth today.

Around this home

Winston Churchill Blvd / King St.

Listing details

MLS® numberW13445462
Listed onJun 15, 2026
Days on market128
UpdatedOct 21, 2026
Listing brokerageRE/MAX REALTY SPECIALISTS INC.
Possession2026-09-15 / Flexible

Helpful tools

Mortgage calculator
Closing costs
Land transfer tax
Buyer guide

Your HOMEH agent

NimaHOMEH agent · Caledon

"I would see it this week."

Ask Nima

Ask HOMEH about this home

Price, neighbourhood, monthly cost. Ask anything.

HOMEH Intelligent Agent is an AI, not a licensed representative. Check anything important with your agent.

© 2026 HOMEH Inc., Brokerage · RECO Registration #6000380 · 505 Highway 7 East, Units 308 & 309, Thornhill, ON L3T 7T1 · Listing data courtesy of the MLS® System of the listing brokerage, deemed reliable but not guaranteed.

Disclaimers and terms

HOMEH is operated by HOMEH Inc., a licensed Ontario real estate brokerage regulated by the Real Estate Council of Ontario (RECO) under the Trust in Real Estate Services Act, 2002 (TRESA). Under TRESA, consumers are entitled to the RECO Information Guide before entering into a representation agreement. Broker of Record Licence #5034208. Toronto Regional Real Estate Board Member #20004000.

Cashback Rebate. Paid by HOMEH Inc., Brokerage from the commission it receives, on closing, to eligible buyers who came to HOMEH as HOMEH leads. Subject to the buyer representation agreement, lender approval and legal limits; amounts vary with price, commission received and transaction type. Not a government incentive, tax credit or refund. Full terms and conditions apply.

Mortgage. Payment figures are estimates for illustration only, not an offer to lend; all financing is on approved credit (OAC). HOMEH Inc., Brokerage is not a mortgage broker, agent or lender; mortgage products and advice come from independent professionals licensed by the Financial Services Regulatory Authority of Ontario (FSRA).

HOMEH Estimate. Worked out with automated tools from recent nearby sales of similar homes. For information only, not an appraisal.

Accuracy. Listings, market data, photos, school, transit and neighbourhood information come from sources believed reliable, including the MLS® System and the Toronto Regional Real Estate Board (TRREB), but are not warranted accurate, current or complete. MLS® listing data is copyright TRREB. It must only be used by consumers with a bona fide interest in the purchase, sale or lease of real estate, and not for any commercial purpose.

Programs. Programs, incentives and benefits on this website are privately administered, may change or end without notice, and imply no government authority, endorsement or affiliation.

Not intended to solicit clients currently under contract with another brokerage.

The trademarks REALTOR®, REALTORS® and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under licence.