Kennedy Rd

4 Bedroom House has been listed for sale at 57 Kennedy Rd in Cheltenham for $2,679,000. Chat with a local expert, book a tour.

Cheltenham

57 Kennedy Rd

57 Kennedy Rd, For Sale in Cheltenham - eXp Commercial Brokerage

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Discover a property that redefines luxury living for the discerning buyer seeking something truly special. This exceptional estate invites you to experience 6, 500 square feet of thoughtfully designed spaces, blending open concept living with cozy private retreats. Nestled on a unique, secluded lot, the approach takes you down a stately tree-lined drive. Step inside and bask in the natural light in your stunning 2-story great room, where two sets of French doors open to your backyard oasis. The gourmet, professionally designed, kitchen is a chef's paradise, offering space for multiple cooks and seamless entertaining. Formal dinners await in the elegant dining room, just steps from the grand foyer and kitchen. Upstairs, the 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, perfect for multi-generational living or guest accommodations. Need more flexibility? Two main-floor offices provide ideal work-from-home setups or creative spaces. Downstairs the expansive recreation room is finished to the same high standard as the rest of the home. You'll also find a second kitchen, exercise room, media room, 2-piece bath, and ample storage on this level. The outdoor living space is 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. Beyond the home nature lovers will enjoy the nearby Caldon Trailway, and Pearson is under a 1/2 hour away providing countryside living without compromise. This is more than a home - it's your next chapter waiting to be written.

Rare Gem in Caledon’s Countryside - Where Elegance Meets Nature. Discover a property that redefines luxury living for the discerning buyer seeking something truly special. This exceptional estate invites you to experience 6, 500 square feet of thoughtfully designed spaces, blending open-concept living with cozy private retreats. Nestled on a unique, secluded lot, this is not just another estate - it’s an exclusive haven waiting to be yours. This all-brick home is an entertainer’s dream and a sanctuary for relaxation. A truly rural experience only minutes from the city. Come experience the perfect balance of luxury, nature, and convenience. This is more than a home - it’s your next chapter waiting to be written.

This secluded home on a little known road is approached by a gracious private lane through its unique 2-acre lot. A beautifully laid out and well-maintained house with more than 6500 square feet of living space including a 2-story great room adjacent to the large open entertainer's kitchen. Two dedicated offices perfect for working from home are also found on the main floor of this home. A generous dining/family room offers a separate space adjacent to the kitchen. A total of 4 bedrooms, 3 with ensuite upstairs, and one with a full bath on the main floor perfect for guests or extended family. A 2-piece bath and large laundry are also on the main floor. The second-floor primary suite is over 700 square feet and must be seen to be believed. Includes a two-person shower, jacuzzi tub, double vanity and an enormous walk-in closet with its own window. Both the other bedrooms not only have jacuzzi baths of their own as well as walk-in closets. The lower level is finished to the same high standard with a huge family room with full kitchen, a dedicated exercise room, 2-piece bath and a separate entrance. The three-car garage completes the house. Outside enjoy your heated in-ground 32 x 16 pool, cabana with 2-piece bath, expansive deck and patio areas, and still have room for pickup sports in a completely private yard. Take the adjacent Caledon Trailway to walk into charming Cheltenham, a rural hamlet located in south-west Caledon. Only 30 minutes to Toronto Pearson International Airport, it is hard to believe you can experience an idyllic lifestyle with such easy access to all the needs of modern life. Caledon has much to offer, including private schools such as King's College and The Hill Academy, amazing golf with the TPC Toronto at Osprey Valley, home to the 2025 RBC Canadian Open, the renown Devil's Pulpit and amazing geographic features like the Badlands. This home must be seen to be fully appreciated!Entertaining kitchen. Two dedicated offices

This exquisite 6, 500 sq. Ft. Estate is the pinnacle of luxury, seamlessly blending elegance, privacy, and sophistication in one of the most coveted locations. A rare offering, every detail has been meticulously curated to create an unparalleled living experience. Nestled on a secluded, tree-lined lot, this exclusive retreat offers ultimate tranquility while remaining effortlessly connected to the best of city conveniences. From the moment you step into the grand foyer, you are greeted with soaring ceilings and sun-drenched interiors. The great room, with its dramatic proportions, features two sets of French doors that open to an outdoor oasis, inviting natural light and breathtaking views of the private backyard. The exterior living space is nothing short of spectacular, boasting an in-ground pool, a stylish cabana with a 2-piece bath, and expansive patios and deck areas designed for elegant entertaining or quiet relaxation. At the heart of the home, the gourmet kitchen is a culinary dream connecting seamlessly to the dining and living spaces. The formal dining room, provides an exquisite setting for unforgettable gatherings. The upper level is a true retreat, where the primary suite serves as a private sanctuary, complete with a spa-like five-piece ensuite and a grand walk-in closet. Two additional bedrooms, each with their own ensuite baths and walk-in closets, offer exceptional comfort for family and guests. A main-floor bedroom with an adjacent three-piece bath provides flexibility for multi-generational living, guest accommodations, or an alternative primary suite option. Designed with both elegance and practicality in mind, this home also offers two main-floor offices. And the fully finished basement features an expansive rec room, kitchen, bath and more. Beyond the estate, nature lovers will appreciate the scenic Caledon Trailway and the convenient location, just 30 minutes to Pearson Airport. This is more than a home—it is a legacy property.

57 Kennedy Rd, Cheltenham, ON

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