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

$1,499,000
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
$1,049,000
3 Beds ⋅ 2 Baths ⋅ W13585418 MLS
PREMIUM CORNER LOT! Welcome to 85 Wright Crescent in Bolton's highly sought-after North Hill! Lovingly maintained by the same owners for over 30 years, this move-in-ready home offers 3 bedrooms, 2 bathrooms, and an exceptional list of upgrades. Features include a stunning custom kitchen with heated floors, beautifully renovated custom bathrooms with heated floors, vaulted ceilings in the family room, custom closet organizers in every bedroom, and timeless neutral décor throughout. Situated on an oversized, fully fenced premium corner lot that widens at the rear of the yard, this property offers exceptional outdoor space for relaxing, entertaining, and family enjoyment. Spend summer evenings on the patio and cozy winter nights by the wood-burning fireplace. Ideally located within walking distance of well-regarded elementary and secondary schools, parks, recreation centre and everyday amenities, this home combines comfort, convenience, and an unbeatable family-friendly location. Outstanding curb appeal and meticulous pride of ownership make this a home you won't want to miss!

85 Wright Crescent, Caledon
$999,900
5 Beds ⋅ 2 Baths ⋅ W13582522 MLS
Nestled in the sought-after Mono Mills community, this spacious 5-level backsplit offers an incredible combination of space, flexibility, and opportunity with 2,852 sq. ft. of finished living space. Featuring 4+1 bedrooms, 2 bathrooms, and two fully equipped kitchens, this home is perfectly suited for multi-generational living, extended families, or buyers looking to offset their mortgage with potential income from the fully finished lower level with its private separate entrance. Designed with functionality in mind, the unique split-level layout provides multiple living spaces for every stage of life. The bright main level offers generous principal rooms, while the lower levels expand into a spacious recreation room, family room, second kitchen, and additional bedroom-creating the ideal setup for in-laws, adult children, or guests. Car enthusiasts, hobbyists, and fitness enthusiasts will appreciate the double car garage plus the bonus finished space, ideal as a private home gym, studio, office, or the opportunity to extend the existing garage into the workshop you've always dreamed of. Step outside to your private backyard, where a covered porch creates the perfect place to enjoy your morning coffee or unwind at the end of the day. With the option to easily screen in the porch, you can create a three-season outdoor living space and enjoy the peaceful setting in comfort while overlooking the backyard. Perfectly positioned in one of Caledon's most desirable communities, this home is a commuter's dream, offering quick access to major routes while maintaining the charm and tranquility of Mono Mills. Whether you're searching for a home that grows with your family, accommodates multiple generations under one roof, or provides exceptional flexibility and income potential, 9 Palace Street delivers a lifestyle that's hard to find.

9 Palace Street, Caledon
$700,000
3 Beds ⋅ 1 Baths ⋅ W13571222 MLS
$700,000. ALTON VILLAGE, DOUBLE + LOT, 3 BEDROOM DETACHED HOME, AFFORDABLE TAXES! Fabulous opportunity to own an Alton detached starter or retirement, offering 3 bedroom, 1 bath perched on a lovely, mature double lot measuring 13.1.8 Front Feet x 145 Deep, located on the hilltop at King and Agnes. 2 blocks from ball park, public library, and desired Alton Public School. This home has a generous country sized kitchen 19.7 'x 11.84' waiting for your growing family. bright living room with 2 picture windows, 3 bedrooms, 1 4 pc bath, and main floor laundry room. The roof is approximately 8 years old, water heater 1 year - owned

7 King Street W, Caledon
$1,799,000
4 Beds ⋅ 4 Baths ⋅ W13563894 MLS
Welcome to 44 Gibson Lake Drive, a rare opportunity to own in one of Palgrave's most prestigious estate communities. Nestled on an exceptionally private, maturely treed lot and surrounded by beautiful custom homes, this spacious 2,200 sq. ft. residence offers the perfect blend of luxury, functionality, and convenience. Unlike many country properties, this home is serviced by municipal water and natural gas, providing comfort, reliability, and lower operating costs. The well-maintained home features 3+1 bedrooms and a bright, fully self-contained above-grade walkout in-law suite with a separate entrance, making it ideal for multigenerational living, extended family, guests, or potential income opportunities. Car enthusiasts, tradespeople, and hobbyists will appreciate the heated attached double garage with epoxy floors, as well as the additional heated detached 1.5-car garage offering valuable extra storage and workspace. The expansive 15,000 sq. ft. paved driveway provides ample parking for vehicles, trailers, and recreational equipment. Extensively landscaped grounds create a private outdoor retreat, while the large deck with elegant glass railings overlooks peaceful forest views. Additional features include two furnaces, central vacuum system, natural gas heating, municipal water service, multiple outbuildings, and recently updated gutters, fascia, and soffits. Ideally located just minutes to Bolton's shopping, restaurants, recreation facilities, schools, parks, and trails, with convenient access to major commuter routes and the GTA. Offering privacy, versatility, and exceptional value in one of Caledon's most sought-after communities, this is estate living at its finest.

44 Gibson Lake Drive, Caledon
$1,575,000
5 Beds ⋅ 5 Baths ⋅ W13559252 MLS
Welcome To This Exquisite Home Situated On A Private One-Acre Lot Surrounded By Multi-MillionDollar Estates. Fully Redesigned And Renovated From Top To Bottom, This Turnkey PropertyOffersd spacious Bedrooms And 5 Elegant Washrooms. Extensive 2022 Upgrades Include New Windows,Roof, A/C, And Septic System - Providing True Peace Of Mind. The Gourmet Kitchen FeaturesTop-Of-The-Line Appliances, Granite Countertops, And Ample Storage, Perfect For Family LivingAnd Entertaining. Large Windows Throughout Fill The Home With Abundant Natural Light. Enjoy APrivate Outdoor Oasis Ideal For Relaxation Or Hosting Guests. Premium Lot With Future PotentialTo Rebuild A Custom Estate. Conveniently Located Just Minutes To Grocery Stores, Schools,Plazas, And Major Highways. A Rare Offering That Combines Lifestyle, Location, And ExceptionalInvestment Potential -Delivering Outstanding Value For Families And Savvy Investors Alike.

12753 Centreville Creek Road E, Caledon
$1,550,000
4 Beds ⋅ 3 Baths ⋅ W13526478 MLS
Nestled on an approximately half-acre lot in the heart of Bolton, this turnkey bungalow offers exceptional privacy with a setting that's completely hidden from the road. Surrounded by mature trees and breathtaking views, you'll feel miles away while enjoying the convenience of being right in town.Thoughtfully updated throughout, the home features newer aluminum tilt-and-turn windows and sliding patio door, most with built-in screens, flooding the home with natural light. Two of the three bedrooms showcase dramatic floor-to-ceiling windows that perfectly frame the picturesque surroundings. Additional upgrades include updated electrical, beautifully renovated bathrooms, and a brand-new roof, providing complete peace of mind.The fully finished basement expands the living space with a luxurious spa-inspired bathroom featuring heated floors. An oversized laundry room with two washing machines adds everyday convenience, while abundant storage throughout the home ensures everything has its place.Outside, the professionally landscaped grounds are designed for both relaxation andentertaining. Enjoy a stunning cedar deck with frameless glass railings, pre-wired and readyfor a hot tub, along with landscape lighting, built-in outdoor speakers, and a beautiful stone patio finished with elegant frameless glass railings. A heated front walkway provides added comfort and convenience during the winter months.Car enthusiasts, hobbyists, and growing families will appreciate the ample parking, generousstorage, and a spacious detached workshop/garage that's perfect for projects, recreational equipment, or additional vehicle storage.This rare, move-in-ready property combines luxury upgrades, incredible privacy, outstanding outdoor living, and the convenience of an in-town location-offering a lifestyle that's truly hard to find.

525 King Street E, Caledon
$1,799,000
2 Baths ⋅ W13524910 MLS
Charming Century Home For Sale For Commercial Use. Busy Downtown Street with Retail, Food, and Services. Downtown Caledon East Village Community Commercial Zoning Allows For A Variety Of Permitted Uses. Large Lot, Add on or Build New. 1800 Square Feet Of Space Over 2 Floors. Ample Parking Space. Large Rear Yard.

15964 Airport Road N, Caledon
$1,115,000
3 Beds ⋅ 3 Baths ⋅ W13522608 MLS
This beautifully renovated (2025/26) open-concept modern contemporary home showcases quality craftsmanship and impressive upgrades throughout, offering a move-in-ready opportunity with stylish finishes and exceptional functionality. From the moment you arrive, the inviting curb appeal, thoughtful landscaping, and welcoming entrance set the tone. The entrance features a new front door, porcelain tile flooring, and an updated handrail with broadloom (2025). Additional upgrades include enhanced lighting, a garage door (2018), and a separate entrance from the garage to the basement. The heart of the home is a stunning fully renovated kitchen with new cabinetry, stainless steel appliances, a striking 96" x 48" quartz waterfall island, touch-activated faucets, backsplash, dual pantries with mini fridge, soft-close cabinetry, and LED lighting. The main floor boasts elegant new hardwood flooring and baseboards, along with a spacious primary bedroom with a 4-piece ensuite and two additional generously sized bedrooms. The finished basement adds living space with a 2-piece bathroom, dedicated laundry room, large crawl space for storage, and three new windows for natural light. Outside, enjoy an exposed aggregate concrete driveway (2018), armour stone wall (2017), and stone steps enhancing curb appeal. A walkout leads to a 12'x24' deck, perfect for relaxing or entertaining. The yard includes a powered shed (2018) and a 10kW solar panel system (2016) providing passive income. Conveniently located near amenities, schools, parks, and transit, this home offers comfort, style, and everyday accessibility.

154 Ridge Road, Caledon
$849,900
3 Beds ⋅ 2 Baths ⋅ W13515358 MLS
Welcome to this beautifully maintained raised bungalow, ideally situated on a generous 95 ft x 121.5 ft lot recently severed in the highly desirable village of Inglewood. Home offers approximately 1,400 sq. ft. on the main level, plus an additional 600 sq. ft. of finished living space in the lower level, this home provides an excellent balance of comfort, functionality, and lifestyle. The main floor features three spacious bedrooms and two full bathrooms, along with a bright open-concept living area filled with natural light and character. Thoughtfully updated finishes, detailed woodwork, and a warm, modern design create an inviting space ideal for both everyday living and entertaining.The fully finished basement includes a large recreation room, a versatile hobby room/workshop conveniently located beside the garage, a dedicated laundry area, and ample storage. An additional unfinished section offers great potential for future customization.Additional highlights include a spacious garage with automatic door opener and direct basement access, a modern kitchen with stainless steel appliances, updated lighting and trim, and freshly painted interiors throughout.The exterior showcases charming stone steps, professional landscaping, and a private rear deck perfect for outdoor enjoyment.Nestled in a picturesque village setting, this property offers the perfect blend of country charm and urban convenience. Ideally located just minutes to Highway 410, approximately 10 minutes to Brampton and 15 minutes to Orangeville, and close to schools, conservation areas, and the scenic Forks of the Credit. Enjoy nearby trails, golf at Osprey Valley Golf Club, and skiing at Caledon Ski Club.Some photographs have been virtually enhanced.

10 Victoria Street, Caledon
$1,199,000
3 Beds ⋅ 2 Baths ⋅ W13514108 MLS
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), 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
$1,199,000
4 Beds ⋅ 2 Baths ⋅ W13468334 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 above-ground 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
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