Cheltenham Homes with 16-30 Approx Age

Welcome to Cheltenham, a charming neighborhood nestled within the picturesque town of Caledon, Ontario. Known for its serene landscapes and tight-knit community, Cheltenham offers a unique blend of rural charm and modern conveniences, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle away from the hustle and bustle of urban life.

The homes in Cheltenham, particularly those built between 16 to 30 years ago, boast a delightful mix of architectural styles that reflect the character of the area. These residences often feature spacious layouts, modern amenities, and beautifully landscaped yards, perfect for enjoying the stunning natural beauty that surrounds the neighborhood. With many properties set against the backdrop of lush greenery and scenic views, you’ll find yourself immersed in a tranquil environment that encourages outdoor living and relaxation.

Cheltenham is not just about beautiful homes; it’s also about community. Residents enjoy easy access to local parks, walking trails, and recreational facilities, fostering an active lifestyle for all ages. The nearby Credit River offers opportunities for fishing, kayaking, and leisurely strolls along the water, while the friendly local shops and dining options provide a warm, welcoming atmosphere.

With excellent schools and a strong sense of community spirit, Cheltenham is a place where families can thrive and create lasting memories. If you're looking for a home in a neighborhood that beautifully balances nature, community, and comfort, Cheltenham is the perfect choice. Come discover the charm of this hidden gem in Caledon, Ontario!

Newest Cheltenham Homes with 16-30 Approx Age

$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

$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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