Caledon Homes with 31-50 Approx Age

Caledon Homes with 31-50 Approx Age

Welcome to Caledon, Ontario—a picturesque gem nestled in the heart of Canada. Known for its stunning landscapes and vibrant community spirit, Caledon is a haven for those seeking a tranquil lifestyle without sacrificing modern conveniences. With its rolling hills, lush forests, and charming rural vistas, this town offers an idyllic backdrop for families, retirees, and everyone in between.

Caledon boasts a rich history, reflected in its diverse architecture and welcoming neighborhoods. Among its housing stock, you'll find a delightful selection of homes aged between 31 to 50 years. These properties often feature unique designs and character that newer constructions may lack, providing a warm, established feel. Many of these homes come with spacious lots, mature trees, and beautifully landscaped gardens, perfect for outdoor enthusiasts and those who love to entertain.

Residents enjoy a plethora of amenities, from local shops and restaurants to parks and recreational facilities. The town is renowned for its outdoor activities, including hiking, biking, and horseback riding in the nearby conservation areas. Families will appreciate the top-rated schools and community programs that foster a strong sense of belonging.

With its convenient access to major highways, Caledon is just a short drive from the bustling cities of Toronto and Brampton, making it an ideal location for commuters. Whether you’re drawn to the area's natural beauty or the charm of its historic homes, Caledon offers a unique blend of serenity and accessibility—truly a wonderful place to call home. Explore the possibilities today and discover your dream home in Caledon!

Newest Caledon Homes with 31-50 Approx Age

14294 Winston Churchill Boulevard, Caledon
$1,988,000
4 Beds ⋅ 3 Baths ⋅ W14114964 MLS
Backing onto protected conservation land with no rear neighbours, this 2.43-acre Terra Cotta estate sits steps from the Caledon Trailway and Terra Cotta Conservation Area. Mature forest frames the property, while open lawn and established perennial beds create spaces to play, entertain and unwind. Garden paths wind past the perennials and beneath a charming arbour to quiet seating areas, with fresh blooms from spring through fall and blazing autumn colour in the forest beyond. The fully fenced pool and patio area make your backyard a private resort. The heated saltwater pool is soft and gentle on skin and eyes, with no harsh chlorine smell, and the waterfall adds a soothing soundtrack to long summer afternoons. Heating extends the swim season from late spring into fall. The large patio offers room for dining, lounging and barbecues, all with the forest as your backdrop. Inside are 3,716 sq ft above grade plus a finished lower level, over 4,700 sq ft in all. The two-storey living room has a vaulted ceiling and a two-way wood-burning fireplace shared with the breakfast room. The kitchen features Miele appliances, including an oversized fridge, built-in oven, cooktop and flush-mount hood, and opens to a sunken family room that walks out to the yard. The main floor also has a formal dining room behind French doors, laundry with a walkout, and a 3-pc bath with heated floor and glass shower, steps from the pool. Upstairs, an open loft works as an office or reading nook, and four bedrooms include a primary suite with his-and-hers walk-in closets. The finished basement adds a large rec room plus a bonus room for a gym, guest room or office. Insulated double garage with epoxy floor. Morning coffee under the arbour, an evening swim beneath the trees: this is country living, minutes from town. Offers welcome Sunday, November 8 at 6 PM. Ontario's Conservation Land Tax incentive program reduces taxable property amount by 1.39 acres from the total area of 2.42 acres.

14294 Winston Churchill Boulevard, Caledon
73 Hutton Crescent, Caledon
$1,099,900
5 Beds ⋅ 4 Baths ⋅ W14095220 MLS
Show with confidence! Beautiful Fantastic 4 Bedroom with 4 bathrooms Home in the sought-after neighborhood in Valleywood. Large Basement completely renovated in 2021, Finished with an awesome bar, Exercise Rm and new bath. Large Eat in Kitchen with walk out to a huge deck and summer retreat in the gazebo. Massive primary bedroom with spa like ensuite and walk in closet. Basement 1268 Sq Ft. Great Family Friendly Neighbourhood.

73 Hutton Crescent, Caledon
190 Longwood Drive, Caledon
$1,079,000
3 Beds ⋅ 4 Baths ⋅ W14030960 MLS
Welcome to 190 Longwood Drive, a beautifully maintained detached home nestled in Bolton's desirable North Hill community. Situated on an impressive 50 x 140 ft lot with no rear neighbours, this spacious 2-storey residence offers the perfect combination of quality craftsmanship, functionality, and outdoor living. Featuring 3 generously sized bedrooms, 4 bathrooms, and parking for 5+ vehicles, this home is designed to accommodate every stage of family life. Step inside to discover timeless finishes, including solid oak hardwood flooring and staircase, a beautifully crafted solid maple kitchen with granite countertops, and an inviting eat-in kitchen and dining area ideal for everyday living and entertaining. A thoughtfully designed main floor offers interior garage access, a convenient side entrance, and a laundry/mudroom area with access to the backyard deck. Upstairs, three spacious bedrooms provide ample room to unwind, complemented by generous closet space throughout. The finished basement adds valuable living space with a versatile open-concept layout, additional bathroom, and dedicated storage. Step outside to your private backyard retreat, surrounded by mature trees with plenty of room to entertain, garden, or create your dream outdoor oasis. With its expansive lot, peaceful setting, and convenient access to Bolton's schools, parks, shopping, and everyday amenities, 190 Longwood Drive is an exceptional opportunity to enjoy the space and lifestyle you've been looking for!

190 Longwood Drive, Caledon
56 Fountainbridge Drive, Caledon
$1,249,000
6 Beds ⋅ 4 Baths ⋅ W13874110 MLS
Welcome to 56 Fountainbridge Drive, a detached 2-storey brick home on Bolton's South Hill with no houses behind for extra privacy. This home offers about 3209 sq ft Livable area (2264Sqft above grade & 945 Legal Basement Apartment) and 4 good-size bedrooms. The main floor has a combined living and dining room with hardwood floors, a family room with a gas fireplace and walkout to the yard, and a kitchen with a breakfast area that walks out to the deck. The large primary bedroom has a 4-piece ensuite and a walk-in closet. The basement is a legal 2-bedroom apartment, great for extended family or rental income to help with the mortgage. The big items are already done, with a new roof in 2025 (papers available), a new furnace in 2024, and a new dishwasher and stove in 2026. Attached double garage and a double driveway with parking for 4 cars. Central air and gas heating on a 44.29 x 122.60 ft lot. Walk to schools, church, shops, supermarket and parks. Quiet and friendly family neighborhood with easy access to Highway 50 and a short drive to Highway 427. A great home for a growing family or a buyer looking for income.

56 Fountainbridge Drive, Caledon
17991 St. Andrew's Road, Caledon
$1,499,000
5 Beds ⋅ 4 Baths ⋅ W13871276 MLS
Welcome to this 4+1 bedroom, 4-level side-split situated on a private One Acre lot, offering the perfect blend of country living, modern comfort, and convenience. Ideally located, with an easy drive to Bolton and Brampton as well as Orangeville , this spacious home has been extensively renovated and upgraded throughout.The heart of the home is the stunning custom kitchen, featuring granite counter/ Lighting, large centre island, gas stove, and quality finishes. Additional interior upgrades include durable high-end engineered vinyl flooring, pot lights, upgraded vinyl-clad windows, a 200-amp electrical service, and a furnace upgraded in 2024, along with an updated central air-conditioning system. Exterior improvements include a 2017 roof, replaced soffits and siding, upgraded garage doors, exterior pot lighting, poured-concrete thruout areas, security cameras, and an electric vehicle charger. The property is also equipped with Starlink internet, an upgraded water softener, pump and pressure tank, and a septic system that was pumped in 2025. Adding tremendous versatility is a separate basement one-bedroom apartment with its own private side entrance-ideal for extended family, guests, or additional living space, as well as a large storage area. Enjoy peaceful country views and plenty of outdoor space, complete with a detached shed featuring heat and hydro, plus a chicken coop for hobbyists and those looking to embrace the country lifestyle. A rare opportunity to enjoy privacy, space, and country living while remaining within convenient reach of local amenities and major communities.Located in a desirable rural setting while remaining close to everyday amenities, this property also offers convenient access to world-class golf, including TPC Toronto at Osprey Valley, home of the RBC Canadian Open, as well as Paintbrush Golf Club and Devil's Pulpit Golf Association. A rare opportunity to enjoy spacious country living with exceptional privacy and future potential.

17991 St. Andrew's Road, Caledon
4310 BOSTON MILLS Road, Caledon
$1,299,000
4 Beds ⋅ 3 Baths ⋅ W13867480 MLS
Spacious 3+1 Bedroom Home with Detached Shop on Scenic 1.2 Acres. Welcome to one of Caledon's most sought after locations. Nestled on a beautifully landscaped 1.2 acre property, this lovingly maintained side-split family home offers the perfect blend of comfort, space and functionality. Featuring 3+1 spacious bedrooms, 2.5 bathrooms and an oversized garage, this home is designed for both everyday living and entertaining. The bright, expansive kitchen offers convenient garage access and opens through glass sliding doors to a large deck overlooking a well-manicured backyard-an ideal setting for family BBQ's, outdoor gatherings, or simply relaxing in your own private oasis. Enjoy evenings around the ready-to-use fire pit, creating lasting memories with family and friends. Adding exceptional value is the impressive 20' x 30' detached shop with hydro, offering endless possibilities such as a workshop, storage space, hobby area, or home-based business. The upper-level features three generously sized bedrooms, including a spacious primary retreat, along with two well-appointed bathrooms. The finished lower level boasts a large family room with glass sliding doors providing a walkout to the backyard, a fourth bedroom, laundry room and a bar area that's perfect for entertaining guests. The finished basement offers abundant storage, a cold cellar and a versatile room currently used as a home office. Pride of ownership is evident throughout this exceptional property. Opportunities like this are rare-don't miss your chance to make this remarkable home your own. Book your private showing today.

4310 BOSTON MILLS Road, Caledon
8 Kevinwood Drive, Caledon
$1,264,999
4 Beds ⋅ 3 Baths ⋅ W13851786 MLS
Some homes make you fall in love with the life you could live there. Slow mornings overlooking open countryside. Summer dinners that linger long after sunset. Evenings when staying home feels like the best plan of all. Thoughtfully renovated throughout, this home pairs country living with the comfort of simply moving in and enjoying. An inviting, open-concept layout brings everyone together, offering space for family traditions, celebrations with friends, and quiet moments in between. Upstairs, three bedrooms and two full bathrooms offer comfortable space to unwind, while the lower level adds a fourth bedroom, a spacious rec room, and another full bathroom-perfect for guests, extended family, or cozy movie nights. With flexibility for growing families and multi-generational living, there's room for your next chapter to unfold. Outside, everyday life feels a little more special. Gather beneath the covered dining area, prepare something delicious at the custom built-in BBQ, or retreat to the 19' x 15' enclosed three-season deck. From the first coffee of the morning to a glass of wine as the sky turns golden, this beautiful extension of the home invites you to slow down and savour the view. Mature apple and pear trees bring seasonal blossoms and the simple pleasure of picking fresh fruit in your own backyard. A custom-built, fully insulated 16' x 16' shed with hydro adds space to make your own. Imagine a peaceful home office, fitness studio, creative retreat, games room, or workshop, with room for the passions that make life feel fuller. Just minutes from schools, parks, local amenities, and major commuter routes, you can enjoy countryside calm while keeping everyday conveniences close. Come for the views. Fall for the feeling. Stay for the life you can already picture here...pictures have been virtually edited to show potential

8 Kevinwood Drive, Caledon
81 De Rose Avenue, Caledon
$1,149,000
3 Beds ⋅ 4 Baths ⋅ W13845580 MLS
Welcome to 81 De Rose Avenue, Bolton! Located in a desirable residential community, this inviting home offers the perfect blend of comfortable living, neighbourhood charm and convenient access to everything Bolton and Caledon have to offer. Step inside to discover a warm and welcoming interior with thoughtfully designed living spaces ideal for everyday family life and entertaining. The home offers well-proportioned rooms, comfortable bedrooms and versatile living areas that provide plenty of flexibility for today's lifestyle. The kitchen provides a practical gathering space for preparing meals and spending time with family and friends, while the adjoining living and dining areas create a comfortable flow throughout the home. Natural light adds to the bright and inviting atmosphere. Outside, enjoy valuable outdoor space for relaxing, entertaining and making the most of the seasons. Set on De Rose Avenue, the property is situated in an established neighbourhood with a welcoming community atmosphere. Enjoy the many amenities Bolton has to offer, including shopping, restaurants, schools, parks, recreation and community services. The surrounding Caledon area is also known for its scenic landscapes, trails and abundant green space, offering a wonderful balance between community living and access to nature. Whether you're looking for a place to call home or an opportunity in an established Bolton neighbourhood, 81 De Rose Avenue offers an excellent opportunity to enjoy the lifestyle and convenience of this sought-after Caledon community.

81 De Rose Avenue, Caledon
19982 Kennedy Road, Caledon
$1,299,000
3 Beds ⋅ 3 Baths ⋅ W13822200 MLS
Imagine coming home to space, and privacy of 1.03 acres - welcome to 19982 Kennedy Rd - surrounded by mature trees, this beautifully maintained 3-bedroom residence offers, 3 bathrooms, a 2-car garage, ample parking, a finished basement, creating approx 3000 sq ft of living space. Step inside to timeless Indian slate flooring and a warm, inviting interior. The chef-inspired kitchen is truly the heart of the home, featuring a Viking propane cooktop with professional hood vent, built-in oven and microwave, granite countertops, custom cabinetry, pot drawers and a generous centre island perfect for gathering. The spacious living room offers space for entertaining, while the family room with wood-burning fireplace creates a cozy retreat. A bright spacious 3-season sunroom extends the living space and opens onto a deck overlooking the private grounds - an ideal spot for morning coffee, summer dining or evening relaxation. Hardwood stairs lead to the upper level where you'll find three well-appointed bedrooms, including a spacious primary retreat with a 4-piece ensuite. The recently renovated finished basement adds exceptional flexibility with a large recreation room, potential 4th bedroom or office, durable vinyl flooring, abundant storage and a bonus workshop. Outside, the pool-sized backyard is framed by mature trees, western exposure and features; propane BBQ hookup, a fire pit, an over-sized shed, offering plenty of room to entertain, play or simply enjoy the peace and privacy of your surroundings. Recent 2026 improvements include a new propane furnace with 10 year transferable warranty, and a new propane hot water tank, and online propane monitoring. Located near renowned golf courses, Island Lake Conservation Area, Forks of the Credit, shopping, dining, schools and healthcare, minutes to Orangeville, easy commute to Brampton and the GTA. Well Pump 2024 (no water bill), Propane Furnace 2026, Propane Hot water tank 2026, Manual Generator Connection.

19982 Kennedy Road, Caledon
193 Royal Valley Drive, Caledon
$1,169,000
4 Beds ⋅ 3 Baths ⋅ W13811730 MLS
Gorgeous Family Home In An Amazing Location! This beautifully maintained four-bedroom home is just a 2-minute walk to Lina Marino Park-featuring basketball courts, soccer fields, and an exceptional playground. The Main Floor Has A Specious Eat In Kitchen With Pull-Up Seating To Granite Kitchen Island And Walk-Out To Back Deck-perfect for family meals and entertaining. The inviting living room includes a cozy gas fireplace, while the formal dining room provides the ideal space for hosting guests. At the front of the home, a large sunlit room offers versatility as a bright home office, a formal living area, or a welcoming receiving room-the choice is yours! Upstairs, you'll find four spacious bedrooms, including a luxurious primary suite with a gas fireplace, walk-in closet, and a four-piece ensuite. A generous flex space on this level can be used as a second office, playroom, homework area, or family lounge. The unfinished basement features high ceilings, a rough-in for a bathroom, and endless potential to customize to your needs. Don't miss the opportunity to own this incredible home in a sought-after community! Roof, Soffits & Eaves (2022), Upstairs Bath (2022), Furnace & Ac (2021), Windows (2019),Double-Car Heated Garage, Freshly painted.

193 Royal Valley Drive, Caledon
74 Downey Drive, Caledon
$749,000
3 Beds ⋅ 1 Baths ⋅ W13799788 MLS
Welcome to 74 Downey Drive, an excellent opportunity to own an affordable detached home in a convenient and family-friendly Bolton neighbourhood. This three-bedroom home offers a functional layout with plenty of potential to update, personalize and make your own. The kitchen features stainless steel appliances, granite countertops and ample cabinet space, while the bright living area overlooks a private backyard surrounded by mature trees, creating a peaceful setting for everyday living. The finished walkout basement provides valuable additional living space and direct access to the backyard, making it ideal for a family room, home office, play area, fitness space or entertainment room. With no homes directly behind, the backyard offers added privacy and plenty of room to relax, entertain guests, garden or enjoy time outdoors with family and friends.**Recent improvements provide added peace of mind, including a new furnace (2023), an owned hot water tank (2023) and a roof replaced in 2020.** These important updates offer buyers the benefit of several major home components already having been addressed. Ideally located within walking distance of schools, parks, shops, restaurants and everyday amenities, this home combines the convenience of an established neighbourhood with the opportunity to create a space that reflects your own personal style. Whether you are a first-time buyer, a growing family or simply looking for a detached home in Bolton, 74 Downey Drive offers comfort, flexibility and plenty of future potential.

74 Downey Drive, Caledon
18599 Horseshoe Hill Road, Caledon
$1,298,000
5 Beds ⋅ 3 Baths ⋅ W13794850 MLS
Located on a paved country road, this 3+2 bedroom, 3-bathroom raised bungalow set on a private, treed 2.89-acre lot features a pond, stream, bush, trails, fenced backyard, circular driveway, and a detached approx. 24 ft. x 30 ft. outbuilding with excellent workshop potential. An ideal property for nature lovers, hobbyists, and extended family living! The main level features an oak kitchen with stainless steel appliances, bright living spaces, and a south-facing deck overlooking the private backyard. The Living room offers hardwood flooring and a propane gas fireplace. Fabulous for extended family or in-law living, the finished basement with above-ground windows includes a spacious rec room with a gas woodstove, laundry area, hobby/workshop, 3-piece bath, bedrooms #4 & #5, and a cold room. The home has a steel roof, vinyl siding, and vinyl casement/awning windows, along with a ground-source heat pump and a fenced backyard. The attached, insulated approx. 23 x 23-foot garage is propane-heated w/ 11 ft. ceiling, a 16 x 10 ft. insulated roll-up steel door, and includes a vertical platform lift (elevator) for enhanced accessibility. An 8 ft. x 12 ft. greenhouse has water, hydro and propane heater. A fabulous opportunity combining privacy, functionality, and natural beauty in a tranquil setting close to major commuter highways 10, 9, and Airport Road. Minutes to all shopping amenities and hospital in nearby Orangeville, 20 mins to Brampton, 1hr to Toronto and 45 minutes to Pearson Airport.

18599 Horseshoe Hill Road, Caledon
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