20643 Kennedy Road, Caledon

A Century Home Steeped in History-With Space to Live, Grow & Play Nestled on a private, tree-lined 2-acre lot just 5 minutes from Orangeville, this enchanting century heritage home is where timeless charm meets modern convenience. Set behind a gated entry & long driveway, this majestic property offers not only a rich historical backdrop but also room to grow, play & dream. At the heart of the home is a thoughtfully transformed living space-what was once an attached garage has been reimagined into a stunning open-concept kitchen & great room. With soaring ceilings, radiant in-floor heating & custom centre island, its the perfect place to gather. One-of-a-kind automated trap door offers access to the crawlspace, while custom Andersen windows & oversized sliding doors (still under warranty) flood the space with natural light & bring the outdoors in. The original homestead still exudes the warmth & authenticity century-home lovers crave-complete with rustic wood floors, exposed brick & cozy wood stove that adds a country feel. Electrical & plumbing have been updated over the years & the layout is both functional & adaptable. Upper-level primary bedroom can easily be converted into 2, creating a 3-bedroom setup. Outdoors, the possibilities are endless. Enjoy the harvest from mature fruit trees & tend to your 10 raised garden beds. Large garden shed & fully stocked wood shed support a self-sufficient lifestyle, while the expansive lot offers a fenced-in area ideal for kids & pets alike & for those who need serious storage or workshop space, a massive 40x60 steel Quonset hut awaits-capable of housing 12 vehicles, boats, trailers or recreational toys. This is more than a home-its a piece of history with a future. With heritage grants available to help preserve character, this property is perfect for those who value craftsmanship, charm, & a connection to the past. Your dream century home awaits-book your private tour today & experience its timeless appeal firsthand.