Cheltenham Real Estate for Sale

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.

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, above ground pool and outdoor living spaces designed to be enjoyed year-round. Upgrades: -Offers 4 updated bedrooms and 2 bathrooms-Over $250,000 invested in thoughtful improvements -Fully renovated Primary Suite with walkout access to the gardens -Fridge, convection oven, & microwave (Dec 2025), Stacked washer and dryer in second-floor laundry (Dec 2025), Wood siding in 2022, New roof and soffits in 2021, Electrical, plumbing, and vapour barrier in 2014. Updated flooring throughout. Reverse osmosis water filtration system. Renovated kitchen with cathedral ceiling and custom cabinetry & double-drawer dishwasher for added flexibility, savings, and convenience -Rough-in for a future bathroom on the second floor -Private retreat gardens with a zen garden, fire pit area, gazebo, large back deck, front patio, and above-ground pool. -Barn and office area with extensive storage, 2 workshops, and a heated office, ideal for entrepreneurs, tradespeople, artists, hobbyists, or anyone working from home. Also includes a former chicken coop with potential for a sauna, studio, or hobby space. -Outdoor lifestyle location within walking distance of parks, trails, river tubing, patio, and an above-ground pool. A former chicken coop offers additional flexibility and potential for conversion into a sauna, studio, or hobby space. Enjoy peaceful Caledon living just minutes from Brampton, Georgetown, Orangeville, Bolton, and Mississauga. This is a rare opportunity to own a move-in-ready property that offers character, functionality, and a true village lifestyle.

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.

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.

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.

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 .