Caledon Homes with 51-99 Approx Age

Caledon Homes with 51-99 Approx Age

Welcome to Caledon, Ontario—a picturesque gem nestled in the heart of Canada. Known for its breathtaking landscapes and vibrant community spirit, Caledon offers a perfect blend of rural charm and modern conveniences. With its rolling hills, lush forests, and winding rivers, this enchanting town is a haven for nature lovers and outdoor enthusiasts alike. Whether you're hiking the scenic trails of the Caledon Trailway or enjoying a leisurely afternoon at one of the many local parks, you’ll find that Caledon is a place where nature and community thrive together.

When it comes to real estate, Caledon boasts a diverse selection of homes, particularly those with an approximate age of 51-99 years. These charming residences reflect the rich history and character of the area, often featuring unique architectural details and spacious lots. Many of these homes have been lovingly maintained or beautifully renovated, offering modern amenities while preserving their vintage charm. Living in one of these homes means becoming part of a vibrant community that values tradition and history, all while enjoying the comforts of contemporary living.

Caledon’s strong sense of community is evident in its local events, farmers' markets, and friendly neighborhood gatherings. With excellent schools, recreational facilities, and easy access to major highways, this town is perfect for families, retirees, and everyone in between. If you’re looking for a place that combines the beauty of nature with the warmth of a close-knit community, Caledon is the ideal choice. Explore our listings today and discover your dream home in this enchanting Ontario town!

Newest Caledon Homes with 51-99 Approx Age

$1,199,000
4 Beds ⋅ 2 Baths ⋅ W13758914 MLS
Welcome to Hilltop Drive. One of Caledon East's most desirable communities. This beautifully updated 4-level side-split offers the ideal blend of modern style, space, and functionality. Featuring four bedrooms and four distinct living levels, this home has been thoughtfully designed to accommodate every stage of family life. At the heart of the home is the stunning renovated kitchen, showcasing an impressive 5' x 9' island, modern cabinetry, stainless appliances, a temperature-controlled wine fridge, abundant storage, and stylish finishes throughout. The adjoining family room is bright and inviting, complete with a walk-out to the patio that seamlessly blends indoor and outdoor living. The upper-level features three spacious bedrooms and a beautifully renovated 4-piece bathroom. On the lower level, you'll find an additional family room with a second walk-out to the yard, a renovated 3-piece bathroom, a fourth bedroom, and a generous laundry room, offering the perfect setup for growing families, multi-generational living, or welcoming overnight guests. The finished fourth lower level provides even more versatile space, with another cozy family room, a beautiful wet bar and seating area, and an abundance of storage space. Summers just got better as you enjoy your own private backyard oasis, surrounded by mature trees, extensive stonework, large garden shed, exceptional privacy, and a beautiful saltwater pool - the perfect setting for entertaining family and friends. Don't miss this incredible opportunity to call this exceptional Caledon East property your forever home!

25 Hilltop Drive, Caledon
$2,174,900
4 Beds ⋅ 3 Baths ⋅ W13749034 MLS
Luxury Meets Nature A Private 29.5-Acre Retreat in Terra Cotta. Experience the perfect fusion of countryside tranquility and modern luxury in this stunning 4-bed, 3-bath estate perched atop one of Terra Cottas most desirable elevations. Situated on 29.5 acres of pristine land in the Niagara Escarpment this one-of-a-kind property offers direct access to the Bruce Trail, Credit Valley River, endless opportunities for hiking, fishing, cross-country skiing, and pond skating. Home Features: Chefs Kitchen Dream: Outfitted with a built-in Dacor double oven, Thermador induction cooktop, B/I dishwasher, wine fridge (75 bottles), fridge, upright freezer, and an instant hot water under-sink dispenser system all grounded by heated bamboo and porcelain flooring. Interior Comforts: 1 wood-burning F/P, formal dining room, sun-filled sunroom with W/O to a sunken hot tub, and a spacious games room . 2 Murphy beds. Premium Utility Systems: Reverse osmosis water filtration, water softener, two sump pumps, owned HWT, C/Vac, C/air, Generac backup generator (wired directly to the home), and a 2000-gallon cistern ensuring year-round reliability. More Highlights: 3 outdoor sheds, new aluminum roof, new energy-eff windows, and modern ELF throughout. Outdoor Experience: Enjoy ultimate privacy with a b/yard waterfall and pond, framed by mature maple trees and rolling woodland. Step onto one of the many walk-outs and immerse yourself in a peaceful setting perfect for morning coffees, family gatherings, or quiet evenings under the stars. Located in the heart of Terra Cotta. This estate offers rare access to natural beauty while remaining within a short drive of city conveniences. This is more than a lifestyle investment. Sch your private showing today and experience the serenity, space and elegance only Terra Cotta can offer. Equipped with Starlink satellite internet

14728 Heritage Road, Caledon
$1,114,000
3 Beds ⋅ 2 Baths ⋅ W13740006 MLS
PUBLIC OPEN HOUSE SATURDAY SEPTEMBER 5th 1-4PM. 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), Garage roof 2026 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
$1,359,000
5 Beds ⋅ 2 Baths ⋅ W13699698 MLS
Welcome to this beautifully and extensively renovated bungalow situated in the desirable, family-friendly community of Caledon Village. Thoughtfully updated throughout, renovations include new windows, flooring, doors, appliances, and much more, creating a stylish, move-in-ready home with modern finishes and a functional, carpet-free layout. The bright and spacious living room showcases an impressive custom-built media wall with integrated LED lighting and a cozy fireplace, creating an inviting space for both everyday living and entertaining. The beautifully updated kitchen features quartz countertops and porcelain tile flooring, offering an attractive combination of contemporary design and functionality. A generous family room provides additional living and entertaining space and features its own fireplace, separate front entrance, and walk-out to the backyard, adding excellent versatility to the home's layout. The finished basement significantly expands the available living space and includes two additional bedrooms and a wet bar, making it ideal for extended family, overnight guests, a recreation area, home office, or additional entertainment space.Step outside to an entertainer's dream backyard. The large, fully fenced property features a beautiful inground saltwater pool, providing the perfect setting for summer gatherings, relaxing poolside, and enjoying the outdoors. The welcoming front porch/deck is finished with modern glass railings, further enhancing the home's attractive curb appeal, while the spacious driveway provides ample parking for family and guests.Ideally located close to parks, schools, shopping, recreation, and everyday amenities, with convenient access to Highway 10, this exceptional property combines modern renovations, generous living space, a private backyard retreat, and an excellent Caledon Village location.A wonderful opportunity to own a turnkey home offering comfort, style, versatility, and outstanding indoor and outdoor living space.

6 Maple Grove Road, Caledon
$8,500,000
5 Beds ⋅ 3 Baths ⋅ W13668606 MLS
Investment opportunity on 4.65 acres in a prime Caledon location. Charming bungalow with open concept living space, set on a deep 205 ft frontage along Mayfield Rd-ideal for future potential or long-term holding. Enjoy the privacy of country living with quick access to Hwy 410, amenities, schools, and transit. A rare offering with strong land value in a rapidly growing corridor.

6688 Mayfield Road, Caledon
$4,599,900
4 Beds ⋅ 3 Baths ⋅ W12945704 MLS
Prime Location! 3.44 Acres Of Future Development Land Designated As "New Employment Area" In HighDemand Area. All Flat Usable Land Conveniently Located With 2 Driveways Onto Hwy 10/HurontarioBetween Old School Rd & King. Located In Very Close Proximity To Planned 413Highway, Easy Access ToHwy 410 & All Major Highways. Don't Miss This Investment Opportunity!

13478 Hurontario Street, Caledon
$1,599,900
W13642450 MLS
Rare opportunity to own 11.24 acres for sale in the heart of Caledon! Surrounded by mature trees and enhanced by a large private pond, this peaceful country retreat is ideal for nature lovers, outdoor enthusiasts, or anyone seeking a tranquil escape from city life. Enjoy breathtaking views, abundant wildlife, and complete privacy in a truly picturesque setting.Along, oversized driveway leads to a raised bungalow with a substantial addition, offering a fantastic opportunity to renovate, customize, or create your dream country home. Recently installed 200-amp electrical service panel provides a solid foundation for future completion. Whether you're looking for a private family estate, weekend retreat, or long-term investment, this unique property offers endless possibilities. Conveniently located with easy access to Hwy 9 and nearby communities, the property also benefits from the proposed Gore Road widening, which may further enhance future accessibility and long-term value. This stunning Managed Forest property offers substantial property tax savings while providing the perfect balance of privacy, natural beauty, and future potential. A truly one-of-a-kind opportunity to own a premium Caledon acreage offering privacy, scenic beauty, tax advantages, and unlimited potential.

18954 The Gore Road, Caledon
$1,799,999
4 Beds ⋅ 2 Baths ⋅ W13633916 MLS
A truly exceptional and rarely offered estate, this remarkable property spans approximately 10 acres and features parking for over 10 vehicles. Nestled in the heart of Caledon, it offers an unparalleled blend of privacy, natural beauty, and convenience. Just steps from Albion Hills Conservation Area and the Trans Canada Trail, outdoor recreation is at your doorstep, while schools, shopping, dining, and major highways are all within easy reach. Whether you're seeking a private retreat, a family estate, or a unique investment opportunity, this extraordinary property presents endless possibilities. A rare offering that must be experienced to be fully appreciated.

16668 Humber station Road, Caledon
$1,345,000
7 Beds ⋅ 3 Baths ⋅ W13621738 MLS
Welcome to this beautifully renovated 4 + 3 bedroom residence on an impressive 0.40-acre lot, offering a rare blend of modern design, functional living space, and picturesque surroundings. Thoughtfully updated throughout, this turnkey property presents an excellent opportunity for families, investors, or multi-generational living. Step inside to a bright, inviting interior featuring hardwood flooring throughout, contemporary light fixtures, and an abundance of pot lights that create a warm, elegant atmosphere. The home showcases custom window coverings, a redesigned kitchen with stylish cabinetry, and tastefully updated bathrooms, all completed with quality finishes and attention to detail. Outside, new exterior lighting and a freshly paved asphalt driveway enhance both curb appeal and convenience. The spacious family room is a focal point, highlighted by a cozy fireplace and a walkout to a private deck where you can relax while enjoying tranquil views of the expansive yard. The open-concept main living area is ideal for entertaining and everyday living, anchored by an entertainer's kitchen with a large central island that seamlessly connects to the dining and living spaces. Practical features further enhance functionality, including two main-floor bedrooms, a mudroom, and a separate laundry room designed for busy households. The recently completed fully finished basement with 3 additional bedrooms, providing flexibility for extended family, guests, or potential rental income. Adding to the home's versatility is an exterior staircase to the second level, creating the possibility for an in-law suite, private workspace, or multi-use living arrangement. With generous indoor and outdoor space, modern upgrades, and income potential, this property is a rare opportunity to own a move-in-ready home with room to grow. 24hrs notice required for viewings as property is tenanted

16045 Hurontario Street, Caledon
$2,900,000
6 Beds ⋅ 4 Baths ⋅ W13616516 MLS
**Excellent opportunity** to acquire 10.45 acres in a prime location of Caledon offering endless possibilities, located close to King St and The Gore Rd. This spacious raised bungalow features 2146 sq. ft. of well-designed living space with 4 generous bedrooms and 3 bathrooms.The bright main level offers an open-concept layout with a country-style kitchen overlooking the family room, expansive living and dining areas, and spacious bedrooms. The fully finished walk-out basement includes its own kitchen, washroom, 2 additional bedrooms, and a large recreation area, making it ideal for extended family, multi-generational living, or potential income opportunities. Also, 2000 Sq Ft Barn with 2 large drive in doors. Surrounded by picturesque countryside while remaining conveniently close to major roads and everyday amenities, this exceptional property combines privacy, space, and outstanding future potential. Whether you're looking for a family estate or investment opportunity, this unique Caledon property is one you won't want to miss.

7190 King Street, Caledon
$1,099,000
4 Beds ⋅ 2 Baths ⋅ W13611036 MLS
On a quiet stretch of The Grange Side Road, this renovated Caledon retreat sits on 1.12 acres, offering privacy, light-filled living, and space to slow down. Located in one of Caledon's most sought-after rural neighbourhoods, this thoughtfully updated 3-bedroom, 2-bath side-split blends modern comfort with the ease of country living. Inside, the home has been completely refreshed with new white oak flooring throughout, a brand new kitchen with new appliances, new washer and dryer, and fully renovated bathrooms, all anchored by a bright, functional layout filled with natural light. The living room is warm and inviting, while the dining room flows seamlessly outdoors to a new patio with pergola-perfect for summer dinners and relaxed evenings. The spacious bedrooms offer comfortable retreats, and the large rec room features a cozy wood burning fireplace, creating an ideal space to unwind. Outside, the extra-deep lot is framed by mature trees and offers endless room to roam, entertain, or garden, all while enjoying the peace and privacy that define this exceptional setting. The home also features updated windows, a recently updated roof, and a 2-car garage. Set among Caledon's most beautiful rural landscapes, close to great schools, skiing, hiking trails, golf, equestrian facilities, and a charming mix of cafes, restaurants, and local shops, this is a lifestyle address that feels both elevated and effortless. A truly special property in one of Caledon's most desirable neighbourhoods. A home that feels as good as it looks.

922 The Grange Side Road, Caledon
$1,499,000
4 Beds ⋅ 3 Baths ⋅ W13606962 MLS
Set on a half-acre lot (100 x 219 ft) along Mississauga Rd between Mayfield and Old School, this two-storey detached home offers 4,250+ sq ft of total living space, 3,000 of it above grade. The main and upper levels were rebuilt in 2011 (plumbing, electrical and HVAC included) and upgraded steadily since. The heart of the home is a large executive kitchen: premium granite counters, wall-to-wallDon't miss this one.custom cabinetry, ceramic tile backsplash, and a breakfast bar. Stainless appliances include a double fridge (2025), two built-in ovens, built-in microwave, 36" gas cooktop and range hood carpet-free interior pairs hardwood in the living areas and bedrooms with ceramic tile in the foyer, kitchen, baths and basement. Pot lights, a natural oak staircase, upgraded baths with premium vanities, and a large multi-functional basement complete the layout. Outside, a driveway that holds 10+ vehicles, an in-ground saltwater pool, a stamped concrete patio, and a detached garage/workshop with hydro and insulation. Mechanicals are a genuine strength: the home is fully spray-foam insulated and runs on a geothermal furnace and A/C that keeps costs low for its size, plus an owned hot water tank, 200-amp service, drilled well with UV and sediment purification, water softener, and updated pump, pressure tank and sump systems. Space, land and unbeatable quality of life on Caledon's southern edge, minutes from Brampton. Don't miss this one.

12806 Mississauga Road, Caledon
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