Caledon Homes with 100+ Approx Age

Caledon Homes with 100+ Approx Age

Welcome to Caledon, a picturesque town nestled in the heart of Ontario, Canada. Known for its stunning landscapes and rich history, Caledon is a hidden gem that offers a perfect blend of rural charm and modern amenities. With its rolling hills, lush forests, and serene conservation areas, this vibrant community is an ideal haven for nature enthusiasts and families alike.

Caledon boasts a diverse array of homes, including many with a fascinating history. For those intrigued by the character and craftsmanship of older properties, the town offers a selection of homes that are over 100 years old. These charming residences often feature unique architectural details, such as intricate woodwork, vintage fixtures, and expansive gardens, all while providing the modern comforts of today. Living in one of these historic homes is like stepping back in time, allowing residents to experience the rich heritage of Caledon firsthand.

The town is also known for its strong sense of community, with numerous local events, farmers' markets, and festivals that foster connections among residents. Whether you're exploring the scenic trails of the Caledon Trailway or enjoying a leisurely afternoon at one of the many parks, there’s always something to do in this welcoming town.

With its beautiful landscapes, historical charm, and a strong community spirit, Caledon is an exceptional place to call home. Whether you're searching for a century-old property with character or a modern family home, Caledon has something to offer everyone. Come discover the magic of Caledon—where history meets harmony!

Newest Caledon Homes with 100+ Approx Age

$3,200,000
4 Beds ⋅ 3 Baths ⋅ W13766840 MLS
Set on 43+ acres with mature trees, open lawns, perennial and vegetable gardens, flagstone patios, and a large stream-fed pond, this exceptional country estate offers timeless character in a highly desirable setting. The circa-1900 stone residence, with a Napier Simpson addition, offers approximately 4,000 sqft of living space with 4 bedrooms, 2 bathrooms, generous principal rooms, tasteful finishes, and preserved historic details throughout. Additional features include an inground pool, a 2.5 car 2 storey coach house with a 1 bedroom studio suite, bank barn and detached garage/storage building. A rare offering with privacy, history, and true estate property appeal. This wonderful property is just minutes from all things' country and conveniently under an hour to the airport and city.

15668 Shaws Creek Road, Caledon
$899,900
3 Beds ⋅ 2 Baths ⋅ W13765474 MLS
Welcome to 1537 Queen St E, a charming mid-1860s home in the heart of Alton on a 10,495 square-foot (0.241 acre) lot. This 3-bedroom + den, 2-bath home offers an open-concept main floor with an updated kitchen, living and dining areas, main-floor primary bedroom and laundry. Hardwood flooring, a rear deck and fully fenced, treed lot add to the home's character and function. The detached 2-car garage is heated, powered and equipped with an EV charger, creating flexible space for a home gym, office, workshop, studio or hobby space in addition to vehicle parking. For golf lovers, this home is just minutes from Tournament Players Club, TPC Toronto at Osprey Valley, Canada's only TPC Network property, host of the RBC Canadian Open in 2025 and 2026, returning in 2027. Outdoor recreation is close to home. Shaw's Creek winds through Alton within walking distance, while nearby Upper Credit Conservation Area offers trails, forests, wetlands and meadows. Caledon Ski Club is ~10-minute drive, offering skiing, snowboarding and other four-season recreation. A c.1860 Late Neoclassical home recognized on Caledon's Heritage Register, preserving a piece of Alton's history while remaining non-designated, with NO HERITAGE PERMIT CURRENTLY REQUIRED for renovations or alterations. Close to Alton Public School, Alton Mill Arts Centre, Millcroft Inn & Spa, local shops and cafés, with Orangeville just minutes away. A character-filled home with a large private lot, flexible bonus space and access to some of Caledon's best golf, trails, skiing and village amenities.

1537 Queen Street E, Caledon
$779,900
2 Beds ⋅ 2 Baths ⋅ W13754344 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
$9,800,000
W13700330 MLS
This exceptional 10-acre development parcel presents a rare opportunity in the heart of Caledon East. Primely located on Airport Road, the property has Draft Plan Approval for 32 townhomes and a 10,000 sq. ft. commercial plaza, while incorporating an impressive approximately 5,000 sq. ft. heritage residence. Situated in a prime downtown location within one of Caledon's rapidly growing communities, the property offers an excellent combination of residential and commercial development potential. Caledon East is known for its charming village atmosphere and country character while providing convenient access to major urban centres. The site is ready to move forward, offering developers and investors an outstanding opportunity in a highly desirable location, less than a 10-minute drive north of Brampton. Please see the attached Site Plan Development concept / Draft Approval Conditions / Notice of Adoption Document for additional details.

16114 Airport Road, Caledon
$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
$899,000
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
Start Your Search