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  • 84 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13771530

    84 Kennedy Road Cheltenham Caledon L7C 2A7
    Main Photo: 84 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13771530
    $2,899,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W13771530
    Bedrooms:
    6
    Bathrooms:
    6
    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. More details
    Listed by ROYAL LEPAGE RCR REALTY
  • 1442 Mill Street in Caledon: Cheltenham House for sale : MLS®# W13694818

    1442 Mill Street Cheltenham Caledon L7C 1S1
    Main Photo: 1442 Mill Street in Caledon: Cheltenham House for sale : MLS®# W13694818
    $635,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W13694818
    Bedrooms:
    3
    Bathrooms:
    2
    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. More details
    Listed by ROYAL LEPAGE MEADOWTOWNE REALTY
  • 14427 Creditview Road in Caledon: Cheltenham House for lease : MLS®# W13596664

    14427 Creditview Road Cheltenham Caledon L7C 1N3
    Main Photo: 14427 Creditview Road in Caledon: Cheltenham House for lease : MLS®# W13596664
    $5,499
    Residential Freehold
    Status:
    For Lease
    MLS® Num:
    W13596664
    Bedrooms:
    4
    Bathrooms:
    3
    Welcome to Cheltenham - One of Caledon's historic villages offering quaint shops and residential community on the Credit River. This property boasts approximately 600 feet of water front on the Credit. The property has been meticulously landscaped and offers walk in potential to the river. Enjoy the hot tub while listening to the water falls of the man made garden/pond feature all the while viewing the Credit River. The house has been well maintained and fully furnished with all amenities. Just move right in!! The house offers to open concept areas in the kitchen and living room which is open to the dining room and family room. Call this your Great Room. BBQ off the back deck and enjoy the large back yard. The perfect place for the family to play. This is a perfect oasis away from the city. A place to go to work or unwind just 30 minutes to the airport. Call this your country home and enjoy all that the countryside has to offer including walking trails, skiing, golf around the corner or swim in the river. More details
    Listed by SUTTON-HEADWATERS REALTY INC.
  • 57 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13505786

    57 Kennedy Road Cheltenham Caledon L7C 2M7
    Main Photo: 57 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13505786
    $2,500,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W13505786
    Bedrooms:
    4
    Bathrooms:
    6
    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. More details
    Listed by KELLER WILLIAMS EDGE REALTY
  • 104 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13452590

    104 Kennedy Road Cheltenham Caledon L7C 2A7
    Main Photo: 104 Kennedy Road in Caledon: Cheltenham House for sale : MLS®# W13452590
    $1,978,500
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W13452590
    Bedrooms:
    6
    Bathrooms:
    3
    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. More details
    Listed by RE/MAX REAL ESTATE CENTRE INC.
  • 13171 Chinguacousy Road in Caledon: Cheltenham House for sale : MLS®# W12791312

    13171 Chinguacousy Road Cheltenham Caledon L7C 3H3
    Main Photo: 13171 Chinguacousy Road in Caledon: Cheltenham House for sale : MLS®# W12791312
    $4,399,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W12791312
    Bedrooms:
    3
    Bathrooms:
    2
    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 More details
    Listed by iCloud Realty Ltd.
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Data was last updated September 30, 2026 at 07:15 PM (UTC)
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.