Caledon Homes with 100+ Approx Age

Caledon Homes with 100+ Approx Age

Welcome to Caledon, a picturesque gem nestled in the heart of Ontario, Canada. Known for its stunning landscapes and rich history, Caledon offers a perfect blend of rural charm and urban convenience. With its rolling hills, lush forests, and vibrant wildlife, this city is a sanctuary for nature lovers and outdoor enthusiasts alike. Residents enjoy an array of recreational activities, including hiking, cycling, and horseback riding, all set against the backdrop of breathtaking natural beauty.

One of the most captivating aspects of Caledon is its diverse architectural heritage. The city proudly features homes that are over 100 years old, showcasing a variety of styles that reflect the area's historical significance. These charming residences exude character and warmth, often boasting unique features such as intricate woodwork, vintage fixtures, and expansive gardens. Owning a piece of history in Caledon not only provides a cozy living space but also offers a connection to the rich narrative of the community.

As you explore the real estate market in Caledon, you'll find that these historic homes are not just a testament to the past but also an opportunity for modern living. Many have been lovingly restored and updated, combining classic elegance with contemporary comforts. Whether you're drawn to the allure of a century-old farmhouse or a quaint Victorian cottage, Caledon’s homes offer a delightful journey through time while providing all the amenities for today’s lifestyle.

Discover the charm of Caledon, where history meets modernity, and find your perfect home in this enchanting city!

Newest Caledon Homes with 100+ Approx Age

$1,999,900
4 Beds ⋅ 3 Baths ⋅ W13428472 MLS
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.

14700 Creditview Road, Caledon
$749,000
3 Beds ⋅ 1 Baths ⋅ W13620750 MLS
Prime mixed-use investment opportunity in the heart of historic downtown Bolton! This charming century home is zoned Institutional (IZ), offering exceptional flexibility for investors, business owners, or owner-occupiers. The main level features a commercial space ideal for a variety of uses, while the upper level offers a bright 2-bedroom, 1-bathroom residential apartment. Excellent opportunity for dual rental income or live-and-work potential. Situated on a high-visibility lot with ample parking in a growing, vibrant community. Updated roof (2025). A rare opportunity with endless potential!

69 King Street W, Caledon
$999,900
4 Beds ⋅ 2 Baths ⋅ W13612054 MLS
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, and outdoor living spaces designed to be enjoyed year-round. Offering updated 4 bedrooms & 2 baths, this home blends historic character with modern comfort. Over $250k has been invested in thoughtful improvements, including a stunning fully renovated Primary Ensuite with walkout access to the gardens, featuring a custom double-sink vanity & freestanding soaker tub. The home also features custom solid wood built-in cabinetry throughout, providing exceptional storage and craftsmanship rarely found. Recent upgrades include a new roof and soffits (2021), updated electrical, plumbing & vapour barrier (2014), and wood siding (2022). The renovated kitchen combines functionality and style with a cathedral ceiling, custom cabinetry, reverse osmosis water filtration, new appliances (fridge, convection oven & microwave - Dec 2025), and a double-drawer dishwasher for added flexibility, savings & convenience when entertaining. Second-floor laundry includes a new stacked washer and dryer (Dec 2025) and a rough-in for a future bathroom. The private retreat gardens feature multiple outdoor spaces including a zen garden, firepit area, gazebo, large back deck, front patio, and an above-ground pool. A former chicken coop offers additional flexibility and potential for conversion into a sauna, studio, or hobby space. The barn and office area is a standout feature, offering extensive storage, two workshops, and a heated office-ideal for entrepreneurs, tradespeople, artists, hobbyists, or anyone working from home. Located within walking distance of parks, trails, river tubing, hiking, cycling, and other outdoor activities, this is a rare opportunity to own a move-in-ready property that offers character, functionality, and a true village lifestyle in one of Caledon's most charming communities.

1510 Station Road, Caledon
$999,000
3 Beds ⋅ 2 Baths ⋅ W13608084 MLS
Welcome to 15 Emma Street in Caledon East. This beautiful century home, built in 1879 in the Victorian Gothic style of the late 19th century, exudes a timeless charm and sense of warmth and welcome, steeped in history. Situated in the oldest section of Caledon East, it still offers the restful quietness of its early inhabitants, along with the amenities of a modern village, access to the Caledon Trailway at its doorstep and Main Street shopping a block away. The location is perfect for retired people, busy career couples or young families, who want to come home to a peaceful environment. As you walk toward the entrance, one of the main features of the house is the two-story bay window and perhaps the cedar tree, which is as old as the house. You enter through a glassed-in sun porch to the spacious L/R and D/R, with high ceilings and crown molding. Flowing from the D/R is a bonus room featuring a bay window and direct access to the porch, which could easily be an office, den or Primary Bedroom. All of these rooms have oak flooring. A door from the L/R leads to the large, country-style kitchen with maple cupboards, original maple floor, pine wainscoting, serving hatch to the dining room and original trap door to the basement. Open to the kitchen is the F/R - skylit and airy with double French doors to a private, wraparound deck with a covered sitting area. The main level has a laundry room with heated floors and a powder room off the kitchen with a door which leads to the composite deck and meticulous gardens. A maple banister welcomes you to the upper level and three bedrooms (one has a shower and vanity ensuite), plus the main bathroom featuring a whirlpool bathtub and a separate shower. Privacy fences and landscaped gardens surround a brick path to the garage, which features a large work bench, built-in cupboards and a storage loft. A generator that powers up the house is sure to please when you need it the most. This is a true gem of a country home!

15 Emma Street, Caledon
$1,139,000
3 Beds ⋅ 2 Baths ⋅ W13551826 MLS
Nestled in the heart of scenic Palgrave, overlooking the historic village pond, this enchanting board and batten century home, complete with a brick garage, is where timeless character meets thoughtful modern living. This is the kind of home that captures your heart the moment you arrive. Beautifully updated with fresh paint throughout, every space feels bright, welcoming, and ready for its next chapter. The custom kitchen and cozy breakfast nook create the perfect place to gather. Refinished hardwood floors add warmth to the inviting living room, where oversized windows flood the home with natural light and are beautifully complemented by Hunter Douglas window coverings. Upstairs, you'll find two spacious bedrooms, each featuring walk-in closets, along with a beautifully appointed four-piece bathroom. The fully finished walkout lower level offers exceptional versatility with a generous recreation room, dedicated office space, an additional bedroom, a three-piece bathroom, laundry room, and cantina. Outdoor living is equally inviting, step through the breezeway onto the deck and unwind as the sun sets over the water, entertain with ease, or launch your canoe for a peaceful paddle across the pond. Every season brings a new backdrop to enjoy from your own backyard. Just steps from Palgrave Rotary Park and the expansive 306-hectare Forest and Wildlife Area, you'll enjoy endless opportunities for walking, hiking, cycling, and exploring nature, all while being only minutes from the vibrant town of Bolton and convenient Highway 9 access.This is more than a beautiful home, it's a lifestyle rooted in community, nature, and the enduring charm of one of Caledon's most treasured villages.

17265 50 Highway, Caledon
$6,800,000
6 Beds ⋅ 4 Baths ⋅ W13531474 MLS
Bursting with charm and storied in history. This 1864 gem and 5 out buildings are with period features and old world character. The Alexander Smith farmhouse is a good representation of the vernacular style known as "Ontario Gothic". This style is the L-Shaped floor plan, polychromatic brick patterning, buff brick quoins and voussoirs. The residence also has coursed polychromatic end chimneys, a projecting bay window, lancet & paired gable windows. A porch with decorative bargeboards wraps around the NE corner of the house. Attached to the NW corner of the house is the summer kitchen & brick carriage house with the original farm bell on the roof. Located across the farm lane, are the 5 out buildings. The buildings consist of the chicken house, implement shed, and three timber frame barns set in a U-Shape, all with medium pitched gable roofs & board and batten cladding. The farm complex is surrounded by a mix of open fields, natural growth cedar & areas of reforestation. A cedar rail fence lines the property. Make this property your hobby farm or transform it into an income property by way of hosting events like weddings or corporate gatherings. How about turning it into a wellness retreat or a bed & breakfast. Even add additional outbuildings and increase your income capabilities. The opportunities at this farm complex are endless.

14650 Heart Lake Road, Caledon
$1,489,000
4 Beds ⋅ 2 Baths ⋅ W13509642 MLS
Visit the REALTOR website for further information about this Listing. Charming Century Home on 13.24 Acres - A Hobby Farmer's Dream. Escape to the countryside and discover this charming century home nestled amongst mature trees on a picturesque 13.24-acre property. Offering the perfect blend of rural tranquility and practical acreage, approximately 60% of the land is workable while the remaining 40% features beautiful wooded areas and a peaceful pond, creating a private natural retreat. Set on a generous 250'x 2,160' lot, this property is ideal for hobby farmers, outdoor enthusiasts, or anyone seeking space to grow and explore. Outbuildings include a 24'x 16' workshop for projects and storage, as well as a 12' x 30' chicken coop ready for your feathered friends. Inside, the home offers 3+1 bedrooms and a functional layout designed for family living. The spacious kitchen and dining area provide plenty of room for gathering and entertaining, while the convenient main-floor laundry adds everyday practicality. Relax in the inviting family room featuring a cozy propane fireplace, or unwind in the living room warmed by a charming wood-burning stove. Located just a 5-minute drive from the local elementary school, this property offers the best of country living with amenities close at hand. Whether you're dreaming of hobby farming, raising animals, gardening, or simply enjoying the beauty of nature, this unique property offers endless possibilities. Don't miss your opportunity to own this exceptional rural retreat.

14877 The Gore Road, Caledon
$11,900,000
3 Beds ⋅ 1 Baths ⋅ W13443814 MLS
Welcome to your own private sanctuary nestled behind a treed ravine, opening up into farm fields currently being farmed. This 98.6 acre parcel is designated white belt along with some greenbelt acreage.This property is adjacent to the current Bolton West Urban expansion area with potential future development possibilities.Come build your dream home - or make a land investment with great potential!!Buildings are being sold on "as is" basis.No access to barn interior due to livestock present.No access to house on first showing.

13708 The Gore Road, Caledon
$935,000
3 Beds ⋅ 2 Baths ⋅ W13416220 MLS
From the moment you arrive, you'll be captivated by the warmth, character and timeless appeal of this charming Century home, tucked away on a quiet street at the edge of one of Bolton's most cherished and established neighborhoods. Surrounded by mature trees and rich local history, this 3 bedroom, 2 bathroom home offers a peaceful retreat while remaining close to all the conveniences of town. The welcoming kitchen features granite countertops and opens to a bright dining room highlighted by a large picture window. The cozy living room is the heart of the home, complete with a beautiful bay window and gas fireplace with a stunning pine mantle, perfect for curling up on a cold evening. A quaint and intimate family room provides the ideal space for movie nights or quiet afternoons, while the mudroom offers everyday practicality and easy access to the backyard. Outside, discover your own private sanctuary. Backing onto mature trees without neighbors behind, the peaceful backyard offers a tranquil setting for morning coffee, summer barbeques, and evenings spent listening to the sounds of nature. The partially finished lower level adds versatility with a den/exercise room, office, 2 pc bathroom and laundry area, complete with a workshop. Full of character, warmth and small-town charm, this lovingly maintained home offers a rare opportunity to enjoy the beauty of a bygone era in a small little pocket away from the busyness of central Bolton. A truly special place to call home. Come and see for yourself and fall in love with this hidden hideaway.

108 Hemlock Street, Caledon
$4,500,000
5 Beds ⋅ 3 Baths ⋅ W13224014 MLS
A Victorian reimagined, complete with a secret English garden. Just outside Belfountain, on nearly 15 acres of Caledon countryside, it is steeped in character and completely its own. The main house holds four bedrooms and three bathrooms, anchored by a bright central kitchen with the family room close at hand, cozy with its own fireplace. A breakfast nook looks out over perennial gardens and the pool beyond, with a screened Muskoka room just around the corner. The living room, with a dramatic architectural staircase as its focal point, overlooks the gardens and pond. A home you fall deeper into with every room. Waking up to gardens and pond, the main floor primary wing is a true sanctuary. A spa-like five piece ensuite, marble throughout, with soaker tub and steam shower. Upstairs, three additional bedrooms and a lovely five piece bath. Outside, the property opens into something rare. A 40 foot rectangular pool at the heart of the grounds, with a pool house and al fresco dining zone built for summer entertaining. A spring-fed pond with fountain and trails winding throughout. Heritage barn ruins that carry their own romance. (A family wedding was once held there, and the potential remains.) Once featured on the Caledon Garden Tour, the gardens include a spectacular Rhododendron forest. The outbuildings are exceptional. A detached two-car garage for the everyday and a heated three-bay garage for hobbies, toys, and your car collection, with one bay currently fitted as a sculpture studio. The garden cottage, a gym today complete with bathroom plus kitchen and laundry hookups, converts easily into a private one-bedroom suite for in-laws, older kids, or guests wanting their own world. A garden tea house overlooking the spring-fed pond, perfect for yoga or meditation. Minutes from Belfountain, close to great schools, skiing, hiking trails, golf, equestrian, local shops and restaurants. This is a home that holds everything.

16927 Winston Churchill Boulevard, Caledon
$849,900
2 Beds ⋅ 2 Baths ⋅ W13170098 MLS
Nestled in the heart of historic Alton, this charming home blends timeless character w/thoughtful modern updates, steps from the Alton Mill, Millcroft Inn & Spa, Osprey Valley, trails & dining. Set on a private & landscaped lot w/parking spaces for 4, the property features a spacious deck for BBQs & outdoor entertaining, patio w/hot tub, large shed, perfect for outdoor living, relaxing & gardening. Inside, the main level showcases original trim work, rustic hardwood floors, modern upgrades blending the home's historic charm w/elegant & custom updates. Two bright sunrooms offer relaxing spaces filled w/natural light. At the heart of the home lies a beautifully updated kitchen featuring ample cabinetry, quality finishes, & a built-in desk area for added functionality, ideal for both everyday living & entertaining. The walkout provides seamless access to the deck, making dining & hosting effortless. The dining room w/pot lights flows into a dedicated office w/built-in shelving, creating a functional & inviting layout. Cozy living rm w/custom built-in cabinetry adds warmth, style, a perfect retreat at the end of the day. The main level primary bdrm boasts pot lights, custom built-ins for closet space, & a stunning modern 3-pc ensuite w/lg walk-in shower, heated floors, skylight & granite vanity. Main level laundry & 4-pc bath serve the upper level, where a lg private bdrm includes custom closet cabinetry. Whether used as a guest room, primary suite alternative, or a creative studio. This upper-level space is both versatile & inviting. Throughout the home, numerous structural & "big ticket" updates provide peace of mind, ensuring that the property is as sound as it is beautiful. These improvements, combined with the home's preserved architectural charm, create a unique blend of old-world character & modern reliability. Welcome to a rare opportunity to enjoy cozy, historic village living in one of Caledon's most sought-after communities. Historical significance in photos.

1429 Queen Street, Caledon
$1,399,900
4 Beds ⋅ 3 Baths ⋅ W13110416 MLS
Discover a rare blend of historic character and modern luxury with this enchanting home, tucked away on a serene street in the heart of Bolton and backing onto the Humber River. Originally built circa 1886, this residence has been thoughtfully updated to meet the demands of contemporary living while preserving its timeless soul. The interior boasts a modern kitchen complete with a large centre island hosting a gas range, granite counters & an open dining area-perfect for hosting family and friends. The main floor living room surrounds a beautiful gas fireplace with classic hardwood floors and piano nook. The rear family room offers a quiet space for family game night, media options and a walkout to the rear patio overlooking the River. There is also the convenience of a main floor laundry room. Upstairs you will love the Primary bedroom that serves as your private sanctuary offering a 3 piece ensuite bath with heated tile floor, walk-in closet and walk-out to a balcony with great view of the River. Three more spacious bedrooms complete the 2nd floor with an updated main bathroom boasting beautiful tile and glass details. The basement level offers a large exercise or games room and separate utility/storage room for off season items and access to additional crawlspace storage. This beautiful home is set on an expansive, park-like lot - a nature lover's dream, featuring lush gardens, outdoor shower and towering mature trees that provide ultimate privacy. Whether you are sipping morning coffee overlooking the water or enjoying the peaceful seclusion of your oversized yard, this property offers a unique opportunity to own a piece of history in a premium riverside setting. Lots of parking including the carport, driveway surface parking and additional gravel lane/pad on west side of house. Easy walk to shops, cafes and restaurants and a short commute to Pearson Airport or major connecting highways.

145 Albert Street, Caledon
Start Your Search