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

$699,999
3 Beds ⋅ 2 Baths ⋅ W13551760 MLS
Charming 3-Bedroom Home in the Heart of Historic Cheltenham Nestled in the picturesque village of Cheltenham, this inviting 3-bedroom, 2bath, 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
$1,199,000
3 Beds ⋅ 2 Baths ⋅ W13514108 MLS
Welcome to this beautifully maintained bungalow offering the perfect blend of comfort, convenience, and exceptional outdoor living. Designed for effortless single-level living, this home features 3 bedrooms, 2 bathrooms, and multiple walkouts that create a seamless connection between the interior and the stunning surrounding landscape. Expansive windows fill the home with natural light while showcasing picturesque views of the beautifully landscaped grounds. The delightful kitchen is sure to impress with high-end appliances, granite countertops, and quality finishes. The inviting great room features hardwood flooring, a cozy gas fireplace, and walkouts at both ends, making it ideal for entertaining or simply enjoying the tranquil setting. The spacious primary suite includes a walkout to the deck, custom closet organizers, and built-in shelving. A finished laundry room adds everyday convenience. Step outside to your own private retreat, complete with extensive multi-level decking, lush perennial gardens, a peaceful stream, and mature trees. Unwind in the hot tub, indulge your green thumb, or enjoy hobbies in the detached heated garage with loft. A combination garden shed with dedicated kayak and bike storage provides additional functionality .Notable updates include a commercial-grade steel roof, a new furnace (2025), and an automatic standby generator for added peace of mind. Offering refined interior finishes and spectacular outdoor spaces, this exceptional property is ideal for those looking to downsize without sacrificing quality, privacy, or lifestyle.

114 Kennedy 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
$1,285,000
4 Beds ⋅ 2 Baths ⋅ W13220846 MLS
Welcome to 26 Kennedy Road - where peaceful country living meets everyday comfort, just minutes from the city. Nestled on approximately 2/3 of an acre in the storybook village of Cheltenham, this beautifully updated 4-bedroom bungalow offers space to breathe, room to grow, and the kind of privacy that feels like a retreat. Inside, sun-drenched rooms glow with natural light, creating a warm and uplifting atmosphere throughout. Hardwood floors, fresh paint (2026), and new carpeting provide a crisp, move-in ready feel, while thoughtful upgrades blend seamlessly with the home's inviting character. The heart of the home is the spacious kitchen, complete with granite countertops, stainless steel appliances, and a bright breakfast area overlooking the backyard and pool - a place where mornings begin slowly and conversations linger long after dinner. The sunken family room, anchored by a new Napoleon gas fireplace (2025), offers garden views and a cozy setting for movie nights, quiet evenings, and holiday gatherings. All four bedrooms are tucked privately at the rear of the home, offering peaceful, light-filled spaces ideal for growing families, guests, or a dedicated home office. Step outside and summer truly comes alive. The fully refurbished 16' x 32' in-ground pool invites endless laughter and sun-soaked afternoons. Tiered decking and interlocking stone create the perfect setting for entertaining, while the charming backyard gazebo provides a shaded escape - a place to unwind, share stories, and build lasting memories with family and friends. With major upgrades including a Trane furnace (2020), Midea ducted heat pump (2025), Generac16kW generator, steel roof, and refurbished septic (2020), Brand New front load Washer (LG),you can enjoy peace of mind along with the lifestyle. This is more than a home, it's a place to slow down, connect, and truly live.

26 Kennedy Road, Caledon
$749,900
1 Beds ⋅ 1 Baths ⋅ W13204878 MLS
Welcome to your own 'Paradise in Caledon' a charming home set on over 1.25 acre with the CreditRiver running through this serene property. Featuring a modern interior with carpet-free hardwood floors, stainless steel appliances, a spacious bedroom and bathroom, plus a workshop shed on the property. Truly one of a kind with endless potential. Ideally located just down the road from the Caledon Trailway and minutes to major highways. This property benefits from the Conservation Land Tax Incentive Program, resulting in a reduction in property taxes.

2424 Olde Base Line 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
$2,998,000
6 Beds ⋅ 6 Baths ⋅ W12394471 MLS
Timeless elegance meets impeccable craftsmanship in this stunning Cheltenham estate. A rare find, this beautifully built 5+1 bed, 6 bath home in the sought-after Cheltenham community offers thoughtful design & exquisite details throughout. Chefs kitchen blending beauty & practicality, featuring a 48" Wolf gas range, Sub Zero fridge/freezer, Bosch dishwasher, built-in microwave, & custom quarter-sawn oak cabinetry. 5" solid white oak floors create an inviting atmosphere. The natural beauty of tumbled limestone, natural stone & marble in the kitchens, baths, & basement enhances the spaces timeless elegance, combining sophistication w/ comfort. The primary suite is a true sanctuary w/ heated floors, a spa-like steam shower, a romantic soaker tub, a spacious walk-in closet & focal fireplace. Every detail has been thoughtfully considered, from coffered ceilings in the dining room to vaulted ceilings in the family room & sunroom, adding architectural charm & grandeur. The main floor also includes a dedicated office, perfect for WFH or quiet study. Upstairs, 3 beds each w/ walk-in closets. Two share a Jack-&-Jill bath, while the 3rd has its own private ensuite creating private retreats for family & guests. Every detail, from custom millwork & extensive closet systems to solid wood doors, reflects timeless quality. Step outside to a beautifully landscaped yard, complete w/ irrigation system & a grand outdoor stone fireplace. The property boasts nearly an acre of lush grounds, with a 3-car garage plus an additional backyard workshop garage w/ a loft ideal for toys, landscape equipment & hobbies. For added versatility, theres a bright, welcoming 1-bed, 1-bath loft apartment w/ its own entrance, walk-in closet & separate laundry perfect for in-laws or rental income. The finished basement offers even more comfort w/ guest bed & bath, media & game zones, a bar, crafts room, gym, & a ton of storage, creating a warm, inviting and functional space for gatherings & daily life.

84 Kennedy Road, Caledon
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