Cheltenham Homes with 100+ Approx Age

Welcome to Cheltenham, a hidden gem nestled within the picturesque landscapes of Caledon, Ontario. This charming neighborhood offers a delightful blend of rural tranquility and vibrant community spirit, making it an ideal place for families, retirees, and anyone seeking a peaceful retreat from the hustle and bustle of urban life.

Cheltenham is renowned for its stunning natural beauty, characterized by lush greenery, rolling hills, and the serene Credit River winding through the area. The neighborhood is perfect for outdoor enthusiasts, with numerous parks and trails that invite you to explore the great outdoors. Whether you enjoy hiking, biking, or simply taking leisurely strolls, Cheltenham's scenic surroundings provide the perfect backdrop for your adventures.

One of the unique aspects of Cheltenham is its rich history, with many homes boasting an impressive age of 100 years or more. These charming residences reflect the area's heritage and architectural diversity, offering a glimpse into the past while providing modern comforts. Imagine living in a home that tells a story, with character-filled details and timeless elegance. The community's commitment to preserving its historical charm is evident in the lovingly maintained properties that line its streets.

In addition to its beautiful homes, Cheltenham fosters a strong sense of community. Residents often come together for local events and gatherings, creating lasting friendships and connections. With its close-knit atmosphere, Cheltenham is not just a place to live; it’s a place to belong.

If you’re looking for a neighborhood that combines history, natural beauty, and a warm community vibe, Cheltenham in Caledon is the perfect place to call home. Come explore the charm and character that await you!

Newest Cheltenham Homes with 100+ Approx Age

$1,999,900

4 Beds ⋅ 3 Baths ⋅ W13428472 MLS

Welcome to a truly exceptional country estate nestled in the heart of Cheltenham, One of Caledon's most picturesque and historic villages. Set on a private 1.4-acre property with approximately 200 feet of frontage within the settlement area of Cheltenham, offering the potential for a lot severance! This beautifully preserved 1862 farmhouse offers over 3,700 Sq Ft of living space. Where historic character and modern comfort blend seamlessly. A tree-lined driveway leads to the stately home, Where tall windows, soaring ceilings, and spacious principal rooms create a bright and inviting atmosphere throughout. The flexible floor plan features four bedrooms, three bathrooms, multiple living and entertaining areas, a dedicated office, library/dining room, family room, and a versatile loft perfect for a studio, home gym, creative space, or additional living area. Modern geothermal heating and cooling, along with heated tile floors, provide efficient year-round comfort while preserving the home's timeless appeal. Outdoors, the property is a private retreat surrounded by mature trees and beautiful landscaping, featuring multiple patios, a sun-filled solarium, and a tranquil pond. Whether enjoyed as a full-time residence, weekend escape, or future investment opportunity with potential severance possibilities, the property offers exceptional versatility. Located within walking distance to the Cheltenham General Store, Credit River, Caledon Trailway, and the famous Cheltenham Badlands, while just minutes to The Pulpit Golf Club, Caledon Ski Club, local cafés, breweries, and conservation areas. Commuters will appreciate convenient access to major highways and being approximately 30 minutes from Toronto Pearson International Airport. A rare opportunity to own a landmark property in one of Caledon's most beloved communities, where small-town charm, natural beauty, and modern Living come together.

14700 Creditview Road, Caledon

$999,900

4 Beds ⋅ 2 Baths ⋅ W13612054 MLS

Welcome to 1510 Station Road, a beautifully updated home in the heart of Cheltenham, set on a rare 0.344-acre lot (~15,000 sq. ft.) surrounded by gardens, mature landscaping, and outdoor living spaces designed to be enjoyed year-round. Offering updated 4 bedrooms & 2 baths, this home blends historic character with modern comfort. Over $250k has been invested in thoughtful improvements, including a stunning fully renovated Primary Ensuite with walkout access to the gardens, featuring a custom double-sink vanity & freestanding soaker tub. The home also features custom solid wood built-in cabinetry throughout, providing exceptional storage and craftsmanship rarely found. Recent upgrades include a new roof and soffits (2021), updated electrical, plumbing & vapour barrier (2014), and wood siding (2022). The renovated kitchen combines functionality and style with a cathedral ceiling, custom cabinetry, reverse osmosis water filtration, new appliances (fridge, convection oven & microwave - Dec 2025), and a double-drawer dishwasher for added flexibility, savings & convenience when entertaining. Second-floor laundry includes a new stacked washer and dryer (Dec 2025) and a rough-in for a future bathroom. The private retreat gardens feature multiple outdoor spaces including a zen garden, firepit area, gazebo, large back deck, front patio, and an above-ground pool. A former chicken coop offers additional flexibility and potential for conversion into a sauna, studio, or hobby space. The barn and office area is a standout feature, offering extensive storage, two workshops, and a heated office-ideal for entrepreneurs, tradespeople, artists, hobbyists, or anyone working from home. Located within walking distance of parks, trails, river tubing, hiking, cycling, and other outdoor activities, this is a rare opportunity to own a move-in-ready property that offers character, functionality, and a true village lifestyle in one of Caledon's most charming communities.

1510 Station Road, Caledon

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