Rural Caledon Homes with 51-99 Approx Age

Rural Caledon Homes with 51-99 Approx Age

Welcome to Rural Caledon, Ontario, a picturesque haven that beautifully marries the charm of country living with modern conveniences. Nestled within the rolling hills and lush landscapes of Caledon, this enchanting neighborhood is perfect for those seeking tranquility without sacrificing accessibility. Just a short drive from the bustling urban centers of Toronto and Brampton, Rural Caledon offers a serene escape while keeping you connected to city life.

The homes in this area, particularly those built between 51 to 99 years ago, exude a timeless charm that reflects the rich history of the region. Many of these residences feature classic architectural styles, with sprawling lawns and mature trees that create an inviting atmosphere. Each home tells a story, making it easy to imagine the lives that have unfolded within their walls. Whether you’re drawn to quaint bungalows or larger family estates, you will find a diverse range of properties that cater to various lifestyles.

Rural Caledon is not just about beautiful homes; it’s about a vibrant community. Residents enjoy access to a wealth of outdoor activities, from hiking and biking trails to nearby conservation areas and parks. The area is also known for its friendly neighbors and strong sense of community, making it an ideal place to raise a family or enjoy a peaceful retirement.

With its stunning landscapes, rich history, and welcoming atmosphere, Rural Caledon is truly a hidden gem in Ontario. Discover your dream home in this idyllic neighborhood, where every day feels like a retreat from the ordinary.

Newest Rural Caledon Homes with 51-99 Approx Age

$3,488,000
4 Beds ⋅ 3 Baths ⋅ W13836708 MLS
Welcome to an exceptional 10 acre property offering the perfect blend of residential comfort and versatile workspace. This spacious 4 bedroom bungalow offers approximately 2,800 sq. ft. of living space and is ideally suited for families, multi generational living, or a live/work lifestyle. The main floor features a bright kitchen with soaring cathedral ceilings, open to a welcoming family room complete with cathedral ceilings and fireplace. A generous great room provides additional flexibility and could easily serve as an in law suite, home office, studio, or extended family space. The finished walkout basement offers an expansive recreation room with an additional fireplace, providing plenty of space for entertaining, relaxing, or creating a dedicated family retreat. The property also features an impressive commercial style building of over 5,500 sq. ft., offering outstanding potential for a variety of business, storage, workshop, or hobby uses. The building includes one truck height garage door and two drive-in garage doors, providing excellent functionality and accessibility. Set on a substantial 10 acre parcel With large spring fed pond, this property presents a rare opportunity to combine home, land, and substantial workspace in one location. An ideal setting for those seeking a unique live/work arrangement with room to grow, operate a business, or accommodate a variety of lifestyle needs. LIVE/WORK..

7191 Castlederg Side Road, Caledon
$1,149,000
6 Beds ⋅ 4 Baths ⋅ W13777854 MLS
Prime Location 3 Bedroom Bungalow House, Beautiful Scenic View 1/2 Acre Lot, Walking Distance To Caledon Golf Course, Cheltenham Badlands, Hiking Trails, Cheltenham Veterinary Centre, Walking Distance15Mins From Brampton, Easy Access To Hwy 410. Open Concept Home With Lots Of Natural Bright Light, Fully Upgraded House. New Windows (2020), Stucco/Plaster And Stone On Exterior, Propane Furnace ( 2021 ). Main Level Spacious Liv & Family , Large Eat-In Kitchen, Spacious Master Br. Beautiful Landscaping, Aggregate Concrete And Asphalt Driveway. New Deck In Backyard. 2 Separate Entrances To Large Finished Basement.

1910 Olde Base Line Road, 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
$1,049,000
3 Beds ⋅ 2 Baths ⋅ W13740006 MLS
PUBLIC OPEN HOUSE Sunday September 27, 1-3 PM. 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
$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
$4,399,000
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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