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Explore Caledon Homes for Sale

Caledon is the perfect blend of countryside charm and modern living. Known for its breathtaking natural beauty, this town is home to the famous Bruce Trail and the scenic Cheltenham Badlands, attracting nature lovers and adventure enthusiasts. Neighborhoods like Bolton, Southfields Village, and Palgrave offer a mix of contemporary Single-family homes and charming Bungalows surrounded by lush greenery. Explore modern Condos, stylish Townhomes, or undeveloped Land for future development. For business ventures, consider Commercial properties or indulge in luxury with Homes with a pool. Stay updated with Just-listed properties for the latest listings.

Caledon also boasts a thriving local food scene, with farmers' markets and restaurants serving farm-to-table cuisine. For families, the town provides excellent schools, recreational programs, and community centers. Caledon’s tranquil atmosphere, combined with its accessibility to Toronto via major highways, makes it a sought-after destination for those looking to escape city life without compromising on modern conveniences.

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Newest Caledon Homes for Sale

This is the kind of piece of land builders chase and collectors dream about. If legacy is what you're building... it starts right here. Introducing one of Palgrave's most exceptional opportunities-a rare 10-acre backyard south-facing lot perched high above the countryside, offering unobstructed views stretching all the way to the Toronto skyline and CN Tower. This remarkable parcel is cleared, gently sloping, and naturally designed for a walkout basement, allowing you to build a home that captures both sunlight and panoramic vistas from every level. Perfect for those envisioning a custom luxury estate, this property provides complete privacy while still being minutes from Caledon's finest schools, trails, golf courses, and equestrian facilities. Building Lots of this caliber-elevated, open, and with skyline views-are nearly impossible to find. Whether your dream is a modern architectural showpiece, a timeless stone manor, or a grand palatial residence, this land offers the perfect canvas. A once-in-a-generation property... for a once-in-a-lifetime home. * Pictures of Homes are Renderings, for marketing purposes only*

10375 Old Church Road, Caledon

5 Beds ⋅ 3 Baths ⋅ W13231492 MLS

Rare Opportunity in Caledon's Growing Urban Core! Discover the perfect blend of space, versatility, and future potential at 7770 Healey Road. Set on a sprawling 0.69-acre lot (150 x 200 ft) within Caledon's designated "New Community/Urban Area" (2025 Official Plan), this expansive 4 +1 bedroom, 3 bathroom raised bungalow offers 4,200 sq.ft.of finished living space. Perfectly positioned, you are just minutes from the convenient amenities of Bolton and located immediately north of the Planned Highway 413 Transportation Corridor. Key Features Include: 1) Dual-Living Versatility: With two full kitchens, two fireplaces, multiple bedrooms, and private entrances, this home is tailor-made for multi-generational living or as a possible income property. 2) Sun-Drenched Interiors: Spanning two levels, the home features oversized above-grade windows that bathe almost every room in natural light. 3) Thoughtful 2026 Upgrades: Freshly painted and boasting a newly renovated primary ensuite and a brand-new roof (2026), the home is move-in ready. Notable features include strip hardwood and ceramic flooring throughout, bright white kitchens, one with granite countertop, and an incredible basement level complete with a wet bar-perfect for hosting indoor gatherings. The heating system was also modernized to propane gas in 2019. 4) Outdoor Living: Start your mornings with coffee, watching the sunrise on the oversized covered front porch, or host memorable family gatherings in the expansive, picturesque backyard-an ideal canvas for outdoor events. 5) Unmatched Infrastructure: With an oversized double-car garage and parking for 10+ vehicles, this property is a dream for car enthusiasts, large families, or those who frequently host guests. 7770 Healey Road is more than just a beautiful and spacious home; it can also be a strategic investment in a rapidly burgeoning community. Schedule your private viewing today.

7770 Healey Road, Caledon

5 Beds ⋅ 4 Baths ⋅ W13230434 MLS

Beautifully Designed Executive Home In The Highly Sought-After Community Of Rural CaledonOffering Approx. 2,900 Sq. Ft. Of Functional Living Space W/ Parking For Up To 6 Vehicles.This Spacious Home Features 5 Bdrms, 4 Full Baths, A Main Floor Office, And A Convenient MainFloor 4-Pc Bath. Ideal For Multi-Generational Living Or Potential Main Floor In-Law Setup.Bright Open-Concept Layout W/ Hardwood Flrs Throughout, 9-Ft Ceilings On Main & 2nd Flr,Separate Family Rm, Gas Fireplace, And Modern Kitchen Overlooking Living & Dining Areas.Spacious Primary Retreat W/ Luxurious 5-Pc Ensuite Including Soaker Tub & Glass Shower. AllAdditional Bdrms Feature Semi-Ensuite Access To Full Baths. Convenient 2nd Flr Laundry &Interior Access From Double Car Garage Through Mudroom. Oak Staircase, Quartz Vanities InBaths & Huge Basement. Located Minutes To Brampton, Trails, Golf Courses, Parks, Hwy 10,Schools, Amenities & Approx. 30 Mins To Pearson Airport. Expansive Backyard Offering Plenty OfOutdoor Space For Family Enjoyment & Entertaining.

30 Spinland Street, Caledon

6 Beds ⋅ 5 Baths ⋅ W13228544 MLS

Belain Farm is a remarkable 96-acre country estate where equestrian living, natural beauty, and timeless heritage converge. Framed by a picturesque maple-lined driveway, private forests, scenic trails, open meadows, and sweeping pastoral views, this exceptional property offers an unparalleled country lifestyle in the heart of Caledon. At the heart of the estate sits a beautifully restored century brick residence, thoughtfully updated while preserving its historic character. Original pine floors, custom millwork, wood-burning fireplaces, and carefully curated finishes create warm and inviting living spaces. A separate studio building offers flexible space for a home office, fitness studio, artist's retreat, or guest accommodation. Designed for horse enthusiasts, the property features a 10-stall barn with a self-contained apartment, four paddocks with run-ins, a sand riding ring, expansive fields, and private trails throughout the property. Just 6 minutes from golf at Osprey Valley, home to the Canadian Open. Close to Woodbine, Angelstone, and Palgrave Equestrian Park, the property is ideally positioned for riders, trainers, and equestrian enthusiasts. Under 45 mins to Pearson International Airport. Beyond its equestrian appeal, Belain Farm offers unique income potential. Its authentic heritage architecture, mature forests, picturesque pond, and storybook setting have made it a sought-after backdrop for television series, feature films, commercials, and media productions. Nature lovers will appreciate the tranquil pond beneath a graceful willow tree, abundant wildlife, mature forests, and the peaceful beauty found throughout the landscape. Protected through the Ontario Farmland Trust, this extraordinary property represents an opportunity to own and steward a meaningful piece of Ontario's agricultural heritage. Located minutes from Belfountain, local shops, cafés, restaurants, and everyday conveniences.

18101 Shaws Creek Road, Caledon

4 Beds ⋅ 3 Baths ⋅ W13224500 MLS

Welcome to this beautifully renovated bungalow in the heart of Caledon Village, offering the perfect blend of modern comfort and country charm. Situated on over half acre of meticulously landscaped property, this exceptional home features 3+1 spacious bedrooms and 3 bathrooms designed for both everyday living and tranquility. Step inside to discover a bright open-concept layout with stylish finishes and seamless flow throughout the main living areas. The renovated kitchen overlooks the dining and living spaces creating an inviting atmosphere for family gatherings and hosting guests. The fully finished basement provides additional living space with ample space for a gym, games room, and full entertainment. The space can easily be transformed into an excellent in-law suite offering flexibility for extended family, guests, or future income opportunities. Outside, enjoy your own private backyard retreat complete with mature landscaping, an in-ground pool, and plenty of green space to relax and unwind. Car enthusiats, hobbyists, and growing families will appreciate the impressive 3-car garage with ample outdoor parking. Located in the deisrable community of Caledon Village, this move-in ready home offers the tranquility of country living while remaining conveniently close to schools, parks, and major commuter routes. A rare opportunity to own a turn-key bungalow on a premium lot - don't miss it!

5 Massari Street, Caledon

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

5 Beds ⋅ 3 Baths ⋅ W13221100 MLS

Welcome to 45 Sunkist Valley Road, a truly special family home nestled in one of Bolton's most sought-after yet quietly tucked-away neighbourhoods. Offering 4+1 bedrooms and a thoughtfully designed layout, this home provides the perfect balance of comfort, functionality, and space for a growing family. From the moment you arrive, you'll feel the warmth and sense of community that makes this hidden pocket of Bolton so desirable. Inside, spacious principal rooms invite family gatherings, while the additional bedroom offers flexibility for guests, a home office, or multigenerational living. Ample parking for 6 cars with no sidewalk for your growing drivers. Step outside and discover the backyard you've always dreamed of. The stunning deck overlooks the sparkling pool and creates the ultimate setting for entertaining family and friends. Whether you're hosting summer barbecues, celebrating life's milestones, or simply unwinding after a long day, this outdoor oasis is designed to bring people together and create lasting memories. A professionally maintained lawn with an in-ground sprinkler system keeps the property looking its best all season long. Thoughtful updates and features throughout the home provide peace of mind and added value, including upgraded attic insulation completed in February 2024 for enhanced energy efficiency, a monitored alarm system, and a reverse osmosis water filtration system. The basement offers even more potential with a rough-in for a future bathroom, allowing you to customize the space to suit your family's evolving needs. Located on a quiet street in a family-friendly neighbourhood known for its welcoming atmosphere and pride of ownership, this is more than just a house-it's a place where children can grow, families can thrive, and memories can be made for years to come.Rarely does an opportunity arise to own a home that offers this combination of location, lifestyle, and future potential. Welcome home to 45 Sunkist Valley Road.

45 Sunkist Valley Road, Caledon

4 Beds ⋅ 4 Baths ⋅ W13218000 MLS

Welcome to your private sanctuary in one of Palgrave's most sought-after estate neighborhoods - where each home is set on a sprawling lot and surrounded by the beauty of nature. This impressive residence sits proudly on 2.3 acres, offering the perfect blend of prestige, privacy, and peaceful living. With its stunning stone and stucco elevation, the home commands attention from the moment you arrive. A timeless facade and manicured grounds create undeniable curb appeal, setting the tone for what awaits inside. Step through the grand entrance to discover a beautifully designed floorplan that balances sophistication and comfort. Every room has been thoughtfully crafted to capture natural light and take full advantage of the tranquil surroundings. Whether hosting elegant gatherings or enjoying quiet family moments, this home delivers the perfect backdrop for both. Enjoy the serene setting, mature trees, and the sense of space only a true estate property can offer - all while being just minutes from Caledon's best schools, trails, and amenities

79 Amos Drive, Caledon

1 Baths ⋅ W13215770 MLS

In Bolton, great exposure, clean, bright, unit with office in front with large windows. 2 man doors 1in front 1 in the rear. 1 overhead door 12 feet high 11 feet wide. Rarely available small units in Bolton. Act fast.

345 Healey Road Unit 3, Caledon

5 Beds ⋅ 4 Baths ⋅ W13214024 MLS

Welcome to a home that truly elevates everyday living. Set on a beautifully private almost half-acre lot in one of Caledon East's most desirable enclaves, this fully renovated residence with over $120,000.00 spent and over 3500 SF of total living space offers a rare combination of luxury, space, and complete move-in readiness. Designed with both families and entertainers in mind, the home delivers a seamless blend of refined finishes and warm, inviting spaces. At its centre is a stunning 450 sq ft chef's kitchen-an extraordinary space that anchors the home and naturally brings people together. Thoughtfully designed and filled with light, it's equally suited for large gatherings or quiet mornings, making it one of the home's most memorable features. The main living areas are spacious and elegant, offering flexibility for both everyday life and hosting. Upstairs, generously sized bedrooms provide comfort and privacy, primary bedroom complete with 4pc ensuite including stand alone tub and shower, while the fully finished basement expands the living space-ideal for a home office, gym, media room, or guest retreat. Step outside and experience your own private oasis escape. The expansive backyard is beautifully landscaped and centred around an in-ground salt water pool and hot tub, creating a resort-like setting for summer and seasonal living. With an in-ground sprinkler system and ample space to relax or entertain, this outdoor environment is as functional as it is inviting. Complete with a double car garage and abundant parking for at least 8 cars, this home offers the tranquility of country-style living while remaining conveniently close to schools, amenities, and commuter routes. For buyers seeking a turnkey property with space to grow, entertain, and unwind-this is a rare and compelling opportunity. Homes offering this level of finish, on lots of this size, seldom come to market. Experience it before it's gone!

5 Valleygreen Crescent S, Caledon

2.23 Acres Corner Lot at Hwy 9 & The Gore Road with Potential to Apply for Commercial Zoning! Situated between Palgrave & Mono Mills this Residential property sits amongst some prestigious golf clubs. 30 minutes to the Toronto Airport. Close to amenities: hike the nearby Bruce Trail which connects to The Caledon Rail Trail, ski at The Caledon Ski Club, Caledon east is nearby with shopping and new community centre, the public school is minutes away & the property is in the boundaries of Mayfield Secondary School for the arts. All of this combined makes this the perfect spot for someone to build their dream country retreat or for a premium investment opportunity! Opportunity to capitalize on a premium corner lot!

The Gore Road, Caledon

3 Beds ⋅ 2 Baths ⋅ W13213154 MLS

Welcome To 33 Hesp!! This Lovely 1175 Sqft Detach 4 Level Backsplit Offers 3+1 Bdrm, 1.5 Baths And Located In A Sought After Charming Bolton Neighbourhood. Freshly Painted. All New Berber Broadloom. This Lovely Home Offers A Family Size Eat-In Kitchen O'rlooking The Family Rm. Spacious Combined Lrm/Drm W/Gleaming Hardwood Flrs, Pot Lights & Crown Mldg. Upper Level W/3 Generous Size Bdrms All W/New Berber. Partially Updated 4Pc Main Bath. Lower Level W/Entertainers Size Family Rm W/Wood F/P & New Berber. Great Size 4th Bdrm/Den W/New Berber. Bright Updated 2Pc Bath. Separate Side Entrance. Ground Level W/Door Entrance Into The Unfinished Laundry/Furnace Rm. Cantina W/Included Shelves & Workbench. Great Size Lot W/No Sidewalk Offering Add'nl Parking. Fenced Rear Yard W/Patio Area. Polished Up Garage Area W/Newer Concrete Slab. Conveniently Close To All Amenities. Roof Approx 2019, Furnace Approx 2016

33 Hesp Drive, Caledon

5 Beds ⋅ 4 Baths ⋅ W13212734 MLS

Located on a prestigious country cul-de-sac, minutes to Orangeville amenities, this quality, custom-built brick bungalow has a partly finished basement with a separate entry. Constructed in 2004 with a thoughtfully designed, functional floorplan, this immaculate home offers approx. 4000 sq.ft. of finished living space, has pro-landscaped interlocking stone front and side walkways, extensive wrap-around rear decking (approximately 1000 sq. ft), perennial gardens, fruit trees & grapevines, a fenced backyard, an approx. 12 ft. x 19 ft. garden shed with electric heat & hydro, an irrigation system in the front & backyard, a hardwired automatic generator (2012) and is set on a mature .86-acre private lot. Hardwood flooring, crown moulding, California shutters, 9-foot ceilings and pot lighting are some of the qualities found thru/o this home. Oak Kitchen w/ walk-in pantry, granite c-tops, c-island, b-bar and walk/o to deck. Great Room w/ coffered ceiling, gas fireplace. Formal Dining and Office have French doors & could be used as bedrooms. Primary has walk-in closet w/ organizers, 5-piece ensuite w/ jacuzzi tub, glass shower & double sinks. Beds #2 & #3 share Jack & Jill 5-piece bath. Loft has h/w, four skylights, & also could be a wonderful den/music/kids space or bedroom. Partially finished basement has sep entry & Cold Rm. Large Rec has a Kitchenette, pot lighting, ceramic flooring. Bed has semi-ensuite to a 3-piece bathroom. Large unfinished man cave currently used as a workshop with many 110/220 outlets, pony panel and has a nearby rough-in. Furnace & A/C (2021), Roof reshingled & skylights (2019). Eco Flo septic, Irrigation system, municipal water & natural gas. Near luxury resorts, golf, skiing & breweries. Centrally located, this home has easy commuter access to the GTA and cottage country via Highways 10, 9, and Airport Rd. Mins to all Orangeville amenities, shopping, farmers' markets, the hospital, 45 mins to Pearson Airport and a 1 hr drive to Toronto.

8 Castlewood Court, Caledon

6 Beds ⋅ 7 Baths ⋅ W13210558 MLS

Exquisite Custom-Built Luxury Estate Situated On A Private 2-Acre Lot In Prestigious Palgrave, Offering Breathtaking Views And Unmatched Privacy. Built In 2021, This Remarkable Residence Features 6,332 Sq Ft Above Grade Plus A Fully Finished 2,311 Sq Ft Walk-Up Basement And An Additional 250 Sq Ft Sunroom, Totaling Approximately 8,893 Sq Ft Of Refined Living Space. Showcasing A Striking Modern Stone And Stucco Exterior With A Rare 4-Car Garage, The Home Is Designed With Exceptional Attention To Detail, Blending Elegance With Everyday Functionality. The Main Level Features A Spacious Foyer, Living And Dining Areas, And A Private Office Highlighted By Soaring 20-Ft Ceilings. 11-Ft Ceilings On The Main Floor, 10-Ft Ceilings On The Second Level, And 9-Ft Ceilings In The Basement. The Second Floor Features 5 Spacious Bedrooms, Each With Its Own Full Washroom And Walk-In Closets. Approximately $400K In Recent Upgrades Elevate The Property, Including Professional Landscaping, Upgraded Stonework, Full Perimeter Fencing, An Extended Wrap-Around Driveway, Elegant Gated Entry, And A Water Softener System. The Grand Double-Height Foyer Leads To Elegant Living And Dining Spaces With Designer Lighting, A Sunroom, And A Sophisticated Family Room With Custom Stone Feature Wall And Linear Fireplace. The Chef-Inspired Kitchen Boasts An Oversized Island, Quartz Countertops, Custom Backsplash, And Premium Built-In Appliances. The Fully Finished Walk-Up Basement Offers A Large Recreation Area, Full Kitchen, Bedroom, And Bathroom With A Separate Entrance, Ideal For Extended Family Living. Hardwood Throughout Including Basement. Full Tarion Warranty Including Basement. A True Statement Of Luxury, Craftsmanship, And Estate Living In One Of Caledon's Most Sought-After Communities.

20 Stinson Street, Caledon

Exceptional 50-acre parcel of land with potential for your dream custom home build, minutes to town. This idyllic country setting offers westerly views over the escarpment, rolling hills, open areas, a seasonal pond, and a fenced-in veggie garden. Enjoy walking, cross-country skiing, or ATV on the trails through the majestic mature forest, home to a wide variety of trees and animals, deer, wild turkeys, and songbirds. A unique attribute is the approx. 40 ft. x 80 ft. older barn, in good condition, with 200-amp electrical service, and offers ample storage space and/or potential to serve as a workshop. There is a drilled well. Located on a quiet country road near the Bruce Trail & just 5 minutes to Caledon East amenities, shopping, Rec center, library, farm markets & stores, Public and Catholic schools and is a 1 hr drive to Toronto. Come and experience what Spring sounds like in the hills of Caledon with peepers peeping, birds singing, and more! This property has been lovingly maintained and enjoyed for many years and is sure to pull at your heartstrings. Showings required to view. ***Do not walk on the property without an appointment.

17218 Innis Lake Road, Caledon

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