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

7190 King Street, Caledon
$2,600,000
6 Beds ⋅ 4 Baths ⋅ W14114094 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
19817 Main Street, Caledon
$850,000
4 Beds ⋅ 3 Baths ⋅ W14112750 MLS
Imagine Waking Up To The Gentle Sounds Of The Credit River, Enjoying Your Morning Coffee Surrounded By Nature, & Coming Home Each Day To Your Own Peaceful Riverside Escape. Welcome To 19817 Main Street, A Charming Detached 1.5-Storey Home Nestled In One Of Caledon's Most Desirable Villages, Where Country Cottage Charm Meets The Comfort And Convenience Of Village Living. Offering 4 Bedrooms, 2.5 Bathrooms, A Walk-Out Lower Level, And A 1.5-Car Garage, This One-Of-A-Kind Property Invites You To Slow Down, Unwind, And Embrace A Lifestyle Surrounded By Natural Beauty. Warm And Welcoming Living Spaces Are Filled With Natural Light And Picturesque Views Of The Credit River, Which Gracefully Winds Along The South And East Sides Of The Property. Step Outside And Discover Your Own Private Backyard Oasis. A Spacious Raised Deck Provides The Perfect Setting For Summer Gatherings, Outdoor Dining, Or Simply Relaxing While Taking In The River Views. Wander Through Lush Perennial Gardens, Retreat To The Charming Gazebo, Or Find Your Favourite Spot By The Water To Enjoy The Peaceful Sounds Of Nature. Whether Entertaining Family And Friends Or Savouring Quiet Moments, Every Season Offers Something Special. Discover Everything That Makes Alton Such A Wonderful Place To Call Home. Enjoy Championship Golf At Osprey Valley, Explore Scenic Hiking And Cycling Trails, Visit Local Cafés, Restaurants, Art Galleries, Parks, And The Historic Alton Mill, Or Indulge In A Relaxing Afternoon At The Millcroft Inn & Spa - All Within Walking Distance! Offering The Tranquility Of Cottage-Country Living Without Sacrificing Everyday Conveniences Or Commuter Accessibility, This Rare Riverside Property Is More Than Just A Home - It's An Opportunity To Embrace A Lifestyle Where Nature, Community, And Comfort Come Together Beautifully. Your Riverside Escape Awaits At 19817 Main Street. Come For The Views, Stay For The Lifestyle, And Fall In Love With The Possibilities! Immediate Occupancy!

19817 Main Street, Caledon
114 Kennedy Road, Caledon
$899,995
3 Beds ⋅ 2 Baths ⋅ W14105554 MLS
Now offered well below original purchase price with additional negotiable bonus incentive!!! 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
172 Bell Air Drive, Caledon
$1,899,000
5 Beds ⋅ 4 Baths ⋅ W13864098 MLS
Welcome to 172 Bell Air Drive, a one of a kind fully renovated, turnkey home offering resort-style living in the heart of Bolton a home designed to enjoy. Set on a 12,000 sq. ft. lot backing onto heritage trails,enclosed by maintenance-free vinyl fencing, this distinctive property combines custom finishes, generous outdoor space and everyday functionality. Enjoy summers by the inground pool, unwind in the separate self cleaning hot tub all year round and entertain on the expansive 1,500sq. ft. maintenance-free vinyl deck. A dedicated BBQ area, convenient outdoor shower and firepit tucked into a corner of the property complete the setting for relaxed afternoons and enjoy a quiet evening under the stars. A versatile four season flex studio provides additional space for acards room, home office, hobbies or personal retreat. Renovated from top to bottom, the carpet-free interior features hardwood flooring on the main and second levels, high-end stainless steel appliances and thought fully incorporated custom kitchen with skylights, Second-floor laundry adds everyday convenience. The basement offers a separate entrance, 2 bedrooms,a kitchen and its own laundry-an ideal layout for extended family or multigenerational living. Epoxy-finished garage flooring with custom storage cabinets, extra freezers and additional sink with seperate entrance leading out to an extra-wide driveway accommodating up to 8 cars,with no sidewalk, add further practicality. Literally minutes from schools, grocery stores, restaurants and everyday amenities is priceless while still bringing the getaway to you.

172 Bell Air Drive, Caledon
18954 The Gore Road, Caledon
$1,499,900
W13866974 MLS
Motivated Sellers! Rare opportunity to own 11.24 acres in the heart of Caledon featuring a large private natural pond, mature trees, scenic views, and abundant wildlife. A long private driveway leads to a raised bungalow with a substantial addition, offering excellent potential to renovate or create your dream country home. Ideal for a private estate, family retreat, or investment opportunity. Conveniently located near Hwy 9 and amenities. Enrolled in MFTIP, offering potential property tax savings. Proposed Gore Road widening may enhance future accessibility and long-term value. Private, peaceful, and full of potential - an exceptional Caledon acreage opportunity!

18954 The Gore Road, Caledon
525 King Street E, Caledon
$1,489,000
4 Beds ⋅ 3 Baths ⋅ W13844570 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 and entertaining. Enjoy a stunning cedar deck with frameless glass railings, pre-wired and ready for 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
7191 Castlederg Side Road, Caledon
$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
20094 Main Street, Caledon
$875,000
3 Beds ⋅ 2 Baths ⋅ W13796790 MLS
Nestled on one of Alton's most picturesque and sought-after streets, this charming home offers the perfect blend of village charm, natural beauty, and modern convenience. Surrounded by Caledon's rolling hills and set on a private backyard oasis, you'll enjoy peaceful living just steps from scenic hiking trails, meandering streams, and breathtaking countryside. Experience the best of Alton's vibrant community with the renowned Millcroft Inn, Alton Mill Arts Centre, Ray's 3rdGeneration Bakery, and the Toronto Osprey Valley golf courses all just a short stroll away. Whether you're enjoying a morning coffee, exploring local galleries, or teeing off on championship fairways, this exceptional location offers an unmatched lifestyle. Inside, the home features a recently updated kitchen designed for both everyday living and entertaining. The finished lower level includes a separate entrance, second kitchen, and a cozy living area-ideal for extended family, guests, or potential in-law accommodations. Year-round comfort is ensured with four ductless heating and cooling systems, complemented by two natural gas radiator heating units and a gas fireplace for efficient and reliable warmth. Conveniently located near major commuter routes, this exceptional property offers the tranquility of country village living without sacrificing accessibility.A rare opportunity to own a beautifully maintained home in one of Caledon's most beloved communities.

20094 Main Street, Caledon
1910 Olde Base Line 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
25 Hilltop Drive, Caledon
$1,179,000
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
14728 Heritage 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
6 Maple Grove Road, Caledon
$1,229,000
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
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