Cheltenham Real Estate

Cheltenham Real Estate

Welcome to Cheltenham, a picturesque community nestled in the heart of Caledon, Ontario. Known for its stunning natural landscapes and rich history, Cheltenham offers a serene escape from the hustle and bustle of city life while still providing easy access to urban amenities.

This charming neighborhood is characterized by its lush greenery, rolling hills, and scenic trails, making it a haven for outdoor enthusiasts. Residents can enjoy leisurely walks along the Credit River or explore the numerous hiking and biking trails that wind through the area. The breathtaking views of the surrounding countryside, especially during the fall when the foliage transforms into a vibrant tapestry of colors, are simply unforgettable.

Cheltenham is also steeped in history, with its quaint village center featuring beautifully preserved heritage buildings that tell the story of the community's past. Local shops and cafes offer a warm, inviting atmosphere where neighbors gather and friendships flourish. The community is known for its friendly residents, fostering a sense of belonging that is hard to find elsewhere.

Families will appreciate the excellent schools and recreational facilities available in the area, ensuring a well-rounded upbringing for children. The neighborhood's close-knit feel is complemented by various community events throughout the year, from farmers' markets to seasonal festivals, bringing everyone together to celebrate the local culture.

Whether you're seeking a peaceful retreat or a vibrant community life, Cheltenham in Caledon is the perfect place to call home. Discover the charm and tranquility of this hidden gem, where every day feels like a breath of fresh air.

Newest Listings in Cheltenham

$635,000
3 Beds ⋅ 2 Baths ⋅ W13694818 MLS
Charming 3-Bedroom Home in the Heart of Historic Cheltenham Nestled in the picturesque village of Cheltenham, this inviting 3-bedroom, 2-bath, two-storey home blends small-town charm with the beauty of Caledon's natural surroundings. Set in an old historic mill village along the scenic Credit River, the property offers tranquil views, rolling hilly terrain, and a warm community atmosphere. Enjoy easy access to the Caledon Railway Trail and the renowned Bruce Trail-perfect for hiking, cycling, and year-round outdoor adventures. Explore nearby landmarks like the Cheltenham Badlands and Forks of the Credit, or stroll to the Cheltenham General Store, just a short walkaway for your morning coffee or local goods. Whether you're seeking a serene retreat or a family-friendly home surrounded by nature and history, this property captures the essence of countryside living-only minutes from urban conveniences.

1442 Mill Street, Caledon
$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
$2,500,000
4 Beds ⋅ 6 Baths ⋅ W13505786 MLS
Experience the perfect balance of luxury, nature, and convenience. This property will appeal to the discerning buyer seeking something truly special. Inside 6,500 square feet of thoughtfully blends open-concept living with cozy private retreats. Nestled on a unique, secluded 1.88-acre lot, this is not just another estate - it's an exclusive haven waiting to be yours. Bask in natural light in the stunning 2-story great room flowing seamlessly into the well appointed kitchen that offers space for multiple cooks and seamless entertaining. The 2nd story primary suite is a private retreat, complete with a luxurious five-piece ensuite and a massive walk-in closet. Two additional bedrooms on this floor each feature their own ensuite baths and walk-in closets, ensuring comfort and privacy for family or guests. A fourth bedroom, conveniently located on the main floor, offers its own adjacent 3-piece bath. Need more flexibility? Two main-floor offices provide ideal work-from-home setups or creative spaces. The fully finished walk-up basement is a world of possibilities. With a second kitchen, exercise room, media room, 2-piece bath, and ample storage, it's ready to be transformed into the ultimate entertainment space or in-law suite. Outside is your private paradise, where the lush yard and pool are surrounded by mature trees, offering complete tranquility. A sweeping drive and 3-car garage in the front. An outdoor living space tailored for unforgettable gatherings, featuring an inground pool, a cabana with a 2-piece bath, expansive patios, and deck areas for dining, lounging, and family fun in the back. Beyond the property, the Caledon Trailway, Credit River and the quaint village of Cheltenham are nearby, or explore local gems like Terra Cotta and Belfountain. With Pearson Airport only 30 minutes and downtown Toronto an hour's drive, this property offers countryside living without compromise.

57 Kennedy Road, Caledon
$1,978,500
6 Beds ⋅ 3 Baths ⋅ W13452590 MLS
Potential For 3 Separate Building Lots. One Of Cheltenham's Most Private Estates, 2 Acres, With An Amazing 200 Feet Frontage, Has The Enjoyment Of Over 10 Acres, Backing Onto Protected Nec. Land, And Siding Onto A Stunning Ravine With Gorgeous Babbling Brook, Complete "MAGIC". Original House, Completely Renovated, Family Room Has Multi Walkouts. Mud Room Has Heated Floors, 3pc Bath, Main Floor Laundry Room. Walk-Out To Covered Deck, Hottub (As Is). 3rd & 4th Level Has 3 Bedroom In Law Suite, (Ground Floor) Heated Floors, Laundry, Walkout To Covered Private Deck.

104 Kennedy Road, Caledon
$1,450,000
5 Beds ⋅ 3 Baths ⋅ W13140028 MLS
Welcome To Fully Updated, All-Brick BUNGALOW Nestled On An Acre Of Beautifully Landscaped Land Backing Onto Scenic Farmland. This Bright & Expansive Home Features Well-Designed Living Space, Perfect For Large Families The Main Level: An Elegant Living/Dining Area Perfect For Family Gatherings That Leads To A White Bright Kitchen With An Walk Out To The Outdoor Deck. The Main Level : Boasts Three Large Bedrooms, A Luxurious 4-Piece Bath With Shower, And Private Balcony Off The Primary Suite. The Walkout Level: Features A Cozy Family Room With Wood Burning Fireplace, An Additional Bedroom, A Modern 3 Pc Bath & A Walkout To the Backyard Plus A Private Side Entrance. The Lower Level Basement- Is An Entertainment Haven With A room A 3 Piece Bath, Additional Rec Area, Plus A Separate Entrance Leading To Next rental unit with Two Bedroom , extended kitchen with 3 Piece full washroom . A Spacious Car Garage, 5 Bedroom and 3 Bathroom .

14811 Creditview Road, Caledon
$4,399,000
3 Beds ⋅ 2 Baths ⋅ W12791312 MLS
Prime 10-Acre Parcel In An Expanding Caledon Location Featuring Clear, Level, And Highly Usable Land. Situated At The Corner Of Chinguacousy Road And Old School Road, Just Minutes From Brampton, This Property Offers Excellent Visibility And Access To Major Routes. The Proposed Highway 413 Corridor Is Planned South Of The Property, Further Strengthening The Area's Long-Term Growth Outlook. Surrounded By Ongoing Development And Infrastructure Improvements, This Is A Strong Opportunity For Agricultural Use, Custom Estate Living, Or Strategic Long-Term Investment. An Existing Approx. 1,800 Sq Ft Bungalow Is Currently Tenanted And Is Being Sold In "As Is, Where Is" Condition. Buyer And Buyer's Agent To Conduct Their Own Due Diligence

13171 Chinguacousy Road, Caledon
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