Caledon Real Estate Search

Explore Caledon Properties 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 Properties for Sale

3 Beds ⋅ 3 Baths ⋅ W13772864 MLS

Welcome to this 2-storey freehold townhouse in the highly sought-after Bolton East community. Featuring a renovated main level with bright open-concept kitchen, 2-piece bathroom, direct access to garage, walkout to a large deck (with gas hook-up), landscaped and fully fenced backyard that is perfect for entertaining, kids, pets or a quiet evening to sit back after a long day. The updated staircase takes you to the upper level offering 3 spacious bedrooms filled with natural light and generous closet space, large hall closet for extra storage and 2 full bathrooms. The finished basement can have many different uses - a recreation room, office, home gym, or additional living space - the possibilities are endless. Additional costly updates completed include new windows (2025), new front door, back sliding door and interior fire rated garage door (all 2025), driveway extension (2020), backyard irrigation system (2024), backyard deck (2022), attic insulation (2025), furnace and air conditioner (both 2022). Parking for up to three vehicles with a private driveway and garage adds everyday convenience. Located near top-rated schools, parks, trails, bike paths, a vibrant community center, library, and dog parks, this home perfectly blends comfort, modern updates, and lifestyle appeal. An excellent opportunity for families or first-time buyers looking for move-in-ready living! A MUST SEE!!

21 Waterbury Street, Caledon

3 Beds ⋅ 2 Baths ⋅ W13772824 MLS

Welcome to Valleywood! This lovely community in Caledon is conveniently located just off the 410 highway and Hurontario Street. Tucked away from the hustle and bustle this attached row home (no maintenance fees) is just perfect for a first time buyer or downsizer! This home features hardwood flooring throughout the main floor and a walk out to the back patio. The kitchen has been recently renovated (2026) and is ready for you to move in and enjoy time with the family around the beautiful island! The upper level features two spacious bedrooms plus a double door entry primary bedroom that spans the back of the home. Offering you a semi ensuite bathroom and a wall to wall closet.The basement is finished as a great hang out spot with tons of storage, a roughed in bathroom and a huge laundry room. Come visit us and see what living in Valleywood is all about! Great neighbours, quiet living and country just down the road.

20 Flemington Drive, Caledon

4 Beds ⋅ 4 Baths ⋅ W13772718 MLS

Beautifully updated and move-in ready family home in Caledon's quiet, safe and highly desirable community of Valleywood. Offering approximately 2,200 sq ft above grade plus a finished basement, this bright and meticulously maintained home is perfect for first-time buyers or growing families. Freshly painted throughout, the functional layout features a combined living and dining room, an upgraded kitchen with stainless steel appliances, and a sunny breakfast area with walk-out to the patio and private backyard. Enjoy exceptional privacy with no neighbours behind, backing onto a large park with mature trees creating a peaceful natural setting. The shed has power and makes a great workshop.A standout feature of the home is the spacious separate family room located between the main and second floor, complete with soaring cathedral ceilings and a cozy gas fireplace, the perfect place for relaxing or family movie nights.Upstairs offers three generously-sized bedrooms including a spacious primary retreat with a large walk-in closet and renovated 4-piece ensuite. A second bedroom also features a walk-in closet, while the third bedroom enjoys access to a 4-piece semi-ensuite.The finished basement with separate entrance through garage side door, adds incredible living space with brand new laminate flooring, a large rec room with built-in bookcases, wet bar,second laundry room, plenty of room for entertaining, games or a home gym, plus an additional bedroom and a 3-piece bathroom.Ideally located within walking distance to parks, trails and the library, and just minutes to shopping, everyday conveniences and Highway 410 for easy commuting. Situated in the sought-after Mayfield Secondary School district, this is the perfect place to start or grow your family!

150 Royal Valley Drive, Caledon

4 Beds ⋅ 3 Baths ⋅ W13772302 MLS

Welcome To 4 Archbury Circle, A Beautifully Upgraded, Move-In-Ready Home In Desirable South Bolton Offering Exceptional Indoor & Outdoor Living. The Inviting Main Floor Features Hardwood Flooring, Crown Moulding, Pot Lights, A Large Bay Window, Custom Staircase Wall Moulding & A Striking Fireplace Feature Wall. The Bright Kitchen Features Quartz Countertops, A Large Centre Island, Shaker-Style Cabinetry, Arabesque Backsplash, Stainless Steel Appliances, Under-Cabinet Lighting & A Walkout From The Dining Area To The Backyard. Upstairs, New Hardwood Flooring (2025) Leads To A Spacious Primary Retreat With Juliet Balcony, Walk-In Closet PLUS Wall-To-Wall Custom Built-In Wardrobe Cabinetry. The Stunning Primary Ensuite Was Completely Renovated In 2025 With Premium Riobel Matte-Black Fixtures, Custom 60" Double Vanity With Onyx Wood Finish, Stone Countertop, Dual LED Backlit Mirrors, Oversized Frameless Glass Shower With Riobel Rainfall System, Recessed Niche, Linear Drain, OVE Fully Electric Smart Bidet, Designer Tile & Floor-To-Ceiling Wood-Slat Feature Wall. The Freshly Painted Finished Basement Offers A Spacious Rec Room, Additional Bedroom, Walk-In Closet, Pot Lights, Laundry Room & Ample Storage. Enjoy A Private, Fully Fenced Backyard With Interlock Patio, Landscaped Gardens & Large Raised Wood Deck With Separate Dining & Lounge Areas. Furnace & A/C Approx. 4 Years Old. Excellent Opportunity For First-Time Buyers, Families Or Downsizers, Close To Schools, Parks, Shopping, Amenities & Major Highways!

4 Archbury Circle, Caledon

4 Beds ⋅ 4 Baths ⋅ W13771608 MLS

Beautiful, recently restyled, one of the BIGGEST houses on the street - 2304 sq.ft.- perfectly nestled in a very desirable location offers 4 spacious good-sized bedrooms and the rare convenience of 3 FULL bathrooms on the upper level plus a powder room on a main. A very practical layout features a modern kitchen, living and dining rooms, a cozy family room with a fireplace, and a walkout to a deck overlooking a scenic RAVINE and POND. Enjoy exceptional privacy with no rear neighbours and beautiful views of birds, geese, ducks, and nature year-round. The finished walkout basement provides valuable additional to living space, perfect for a recreation room, home office, or a growing family. Complete with a two-car garage, and a recently renovated driveway for two cars. Conveniently located near schools, parks, shopping. A wonderful opportunity to enjoy space, privacy, and nature in a sought-after community.

43 Crestridge Drive, Caledon

6 Beds ⋅ 6 Baths ⋅ W13771530 MLS

Timeless elegance meets impeccable craftsmanship in this stunning Cheltenham estate. A rare find, this beautifully built 5+1 bed, 6 bath home in the sought-after Cheltenham community offers thoughtful design & exquisite details throughout. Chefs kitchen blending beauty & practicality, featuring a 48" Wolf gas range, Sub Zero fridge/freezer, Bosch dishwasher, built-in microwave, & custom quarter-sawn oak cabinetry. 5" solid white oak floors create an inviting atmosphere. The natural beauty of tumbled limestone, natural stone & marble in the kitchens, baths, & basement enhances the spaces timeless elegance, combining sophistication w/ comfort. The primary suite is a true sanctuary w/ heated floors, a spa-like steam shower, a romantic soaker tub, a spacious walk-in closet & focal fireplace. Every detail has been thoughtfully considered, from coffered ceilings in the dining room to vaulted ceilings in the family room & sunroom, adding architectural charm & grandeur. The main floor also includes a dedicated office, perfect for WFH or quiet study. Upstairs, 3 beds each w/ walk-in closets. Two share a Jack-&-Jill bath, while the 3rd has its own private ensuite creating private retreats for family & guests. Every detail, from custom millwork & extensive closet systems to solid wood doors, reflects timeless quality. Step outside to a beautifully landscaped yard, complete w/ irrigation system & a grand outdoor stone fireplace. The property boasts nearly an acre of lush grounds, with a 3-car garage plus an additional backyard workshop garage w/ a loft ideal for toys, landscape equipment & hobbies. For added versatility, theres a bright, welcoming 1-bed, 1-bath loft apartment w/ its own entrance, walk-in closet & separate laundry perfect for in-laws or rental income. The finished basement offers even more comfort w/ guest bed & bath, media & game zones, a bar, crafts room, gym, & a ton of storage, creating a warm, inviting and functional space for gatherings & daily life.

84 Kennedy Road, Caledon

3 Beds ⋅ 2 Baths ⋅ W13771438 MLS

Wow, This Is An Absolute Must-See Showstopper, Priced To Sell Immediately! This Stunning 3-Bedrooms, 2-Washrooms Home Sits On A Premium Corner Lot In Caledon, Offering Unbeatable Value And Convenience! Step Inside And Be Greeted By An Elegant Foyer, Creating A Grand First Impression With Huge Living Room! The 9' High Ceilings On The Main And Second Floor Enhance The Sense Of Space And Airiness. The Open-Concept Great Room Is Perfect For Relaxing And Entertaining, While The Gleaming Hardwood Floors On The Main And Second Level Add A Touch Of Elegance And Luxury. The Designer Chefs Kitchen Is A True Standout, Quartz Counter Tops, High-End Stainless Steel Appliances, And Stylish Finishes, Making It Both Functional And Stunning! The Master Bedroom Is A Private Retreat, Offering Walk-In Closets! All Three Bedrooms Are Generously Sized, Offering Ample Space And Comfort For The Whole Family. Premium Laminate Floors Through Out Third Floor! Enjoy The Beautifully Landscaped Sideyard! Central Air Conditioning Ensures Comfort Throughout The Year. With Premium Finishes, Thoughtful Design, And A Prime Lot Location, This Home Offers The Best Of Luxury And Practicality! ! Home With A Small POTL Fees Of $81! Steps To School, Park, And Amenities. Stylish Living Space With Plenty Of Room To Grow! Dont Miss Out On This Incredible Opportunity Schedule Your Viewing Today Before Its Gone!

2 Cosbury Lane, Caledon

5 Beds ⋅ 5 Baths ⋅ W13771366 MLS

Set on approximately 15.8 acres this exceptional opportunity to acquire a distinctive, income-producing multi-residential estate in the heart of scenic Caledon. Seamlessly combining rural charm with strong investment potential, this remarkable property features 3 self-contained residential units, a detached barn, and picturesque countryside views-all located within an hour of Toronto. Ideally suited for multi-generational living, savvy investors, or those seeking a private lifestyle retreat or hobby farm, the property offers outstanding versatility and long-term value. The 4-stall barn presents endless possibilities for equestrian use, workshop space, storage, or an agri-focused lifestyle. Each residence is thoughtfully designed with its own private entrance, generous parking, and modern updates throughout, providing both comfort and independence for occupants. Enjoy the convenience of nearby amenities including hiking trails, equestrian facilities, golf courses, and local markets, along with easy access to Highways 400, 427, and 407. The grounds showcase a gated entry, a tree-lined driveway, mature landscaping, perennial gardens, and multiple outdoor living spaces including a pergola, gazebo, and expansive decks-perfect for relaxing or entertaining. Additional features include two wells, two septic systems, a 10kW auto-start backup generator, and fiber-optic internet service via Vianet to both dwellings. Recent upgrades include new roofs and windows on both homes, updated furnace and air conditioning systems, attic insulation in the main residence, and a mini-split heat pump in the guest house. A rare offering in one of Caledon's most desirable rural enclaves-move in, invest, or create your ideal country lifestyle.

14902 Mount Pleasant Road, Caledon

4 Beds ⋅ 4 Baths ⋅ W13770806 MLS

Welcome to this charming semi-detached home in a desirable Bolton neighbourhood, offering the perfect blend of functionality, comfort, and opportunity. Thoughtfully laid out, the home features a bright and inviting main floor with a functional kitchen, comfortable living spaces, and plenty of natural light throughout. Upstairs, you'll find three well-sized bedrooms offering flexibility for a growing family, guests, or a home office. The finished basement provides valuable additional living space, perfect for a recreation room, home gym, office, or entertainment area. Step outside to enjoy the backyard, an ideal setting for summer entertaining, family gatherings, or simply relaxing outdoors. With a practical layout, generous natural light, and plenty of potential to personalize and make it your own, this home is an excellent opportunity to get into one of Bolton's desirable communities. Note: some photos have been virtually staged

88 Humbershed Crescent, Caledon

8 Beds ⋅ 6 Baths ⋅ W13769634 MLS

Immaculate 3700 sq ft detached home featuring 5+3 bedrooms and 6 bathrooms, complete with a legal second dwelling unit. This stone-and-brick beauty sits on a deep lot backing onto a ravine, offering privacy and scenic views. The main level showcases upgraded porcelain tile, 9 ft ceilings, a living/dining area, and a spacious family room with a gas fireplace. The chef's kitchen includes a breakfast bar, seamless quartz countertops and backsplash, an eat-in area with walkout to the deck, and wide-plank oak-stained hardwood carried throughout with matching staircase and iron pickets. The primary bedroom offers his-and-her walk-in closets and a spa-like ensuite with double sinks, soaker tub, and separate shower; the second bedroom also features a walk-in closet. Pot lights throughout the living/dining, great room, kitchen, and exterior. A ground-floor in-law suite includes an open-concept kitchen with quartz counters, 1 bedroom, 1 bathroom, laundry, and walkout to the backyard. The legal basement apartment offers 3 bedrooms, 1 bathroom, a full kitchen with stainless steel appliances, 6 above-grade windows, and separate laundry. Additional features include electric car charger wiring and a BBQ gas line installed by the builder.

574 Queen Mary Drive, Caledon

4 Beds ⋅ 3 Baths ⋅ W13769436 MLS

Large sunny corner townhouse built by Townwood Homes. 1796 Sq.Ft Features 4 Bedrooms. 3 Washrooms, Beautiful Eat In Kitchen, Granite Kitchen Countertops, Open Concept Layout! 9Ft Ceilings On Main Level & Hardwood Flrs Throughout. Master Bedroom Has 5 Piece Luxury Spa Ensuite W/T Frameless Glass Shower. Beautiful Yard With Custom Deck, Gazebo And Built It Bbq

68 True Blue Crescent, Caledon

4 Beds ⋅ 3 Baths ⋅ W13768978 MLS

Welcome to this bright, spacious, and exceptionally functional 3-bedroom bungalow inthe highly sought-after community of Valleywood, Caledon. From the moment you stepinside, you will love the abundance of natural light and the seamless flow of the home.The main level features beautiful hardwood floors stretching across the spacious livingroom, large formal dining room, and all three bedrooms. At the heart of the home is afantastic, family-sized kitchen boasting abundant counter and cabinet space, which walksout directly to a private deck and yard-making it absolutely perfect for entertaining andsummer BBQs. The primary bedroom serves as a peaceful retreat, complete with its ownprivate 4-piece ensuite. For added convenience, the 2-car garage offers direct, seamlessaccess right into the home.Downstairs, the fully finished basement completely doubles your living space and feelsincredibly bright thanks to large windows that let in tons of natural light. This massive,open-concept area is fantastic for many different options, whether you need an in-lawsuite, multi-generational living, or the ultimate recreation hub. It comes fully equippedwith a second kitchen featuring a gas stove, a cozy gas fireplace in the large great room,an additional washroom, and a dedicated office space that could easily serve as a 4thbedroom.Perfectly situated for effortless commuting, this property offers unbeatable access toHighway 10 and Highway 410, alongside easy public transit connections. It is alsoideally positioned between major healthcare facilities, offering quick and convenientproximity to both Brampton Civic Hospital and Headwaters Health Care Centre inOrangeville. This versatile Valleywood gem truly has it all!

34 Kirkwood Crescent, Caledon

4 Beds ⋅ 3 Baths ⋅ W13768664 MLS

Welcome to 15 Caledon Mountain Drive, a one-of-a-kind, turn-key, country retreat set on 3.3 private acres in the charming village of Belfountain. Tucked away in the sought after Caledon Mountain Estates. This beautifully reimagined home offers over 4000 Sq Ft of finished living space which was completely gutted and extensively renovated by Caledon Build In 2020. Blending modern design with the tranquillity of its natural surroundings. The thoughtfully designed interior features Canadian-made engineered hardwood flooring, a custom kitchen with Fox Custom Woodworks and new high-end integrated appliances, and bright, spacious principal rooms designed for everyday living and entertaining. Major 2020 improvements include a new metal roof, Marvin windows (lifetime warranty), exterior brick and Maibec siding, all new insulation, kitchen, flooring, bathrooms, extensive landscaping and more. Outdoors, enjoy your own private backyard oasis surrounded by mature trees and expansive green space, complete with an in-ground pool by Solda Pools (2019). Tucked away at the back of the property, with it's own private driveway, is a separate freestanding studio featuring an expansive main level, loft-style upper space, balcony, and 2-piece washroom - ideal for a creative studio, home office, gym, or additional recreational space. A 2 car garage and a newly paved oversized driveway provide ample parking. Nestled in the heart of Belfountain, only minutes to local cafes and butcher shops, the town of Erin, Caledon Ski Club, Pulpit Club Golf courses, TPC at Osprey Valley and so much more! This exceptional property offers tranquility, privacy and country living while remaining close to the village, conservation areas, trails, parks, local shops and dining, dnd convenient commuter routes connecting to Caledon and the GTA. Under 40 minutes to Pearson Airport.

15 Caledon Mountain Drive, Caledon

4 Beds ⋅ 4 Baths ⋅ W13768554 MLS

Escape to a home that truly understands the meaning of "space." Situated on an expansive lot, this custom-built masterpiece offers over 3,500 square feet of thoughtfully designed living area. This isn't just a house; it's a lifestyle upgrade for families who want room to breathe without sacrificing modern convenience. The heart of the home features a stunning open-concept floor plan that manages to feel incredibly cozy despite its grand scale. Flooded with natural light through large, picturesque windows, the main level is designed for effortless connection. This home includes a rare, dedicated Arts and Crafts room-perfect for a home studio, classroom, or hobby space plus a 3-car garage with enough parking for the whole extended family. Whether you're hosting a holiday dinner or enjoying a quiet evening by the fire, the "dreamy country" aesthetic provides a warm, timeless backdrop.

13905 Kennedy Road, Caledon

4 Beds ⋅ 3 Baths ⋅ W13768340 MLS

LISTED MLS Pricing is PURCHASE PRICE NET OF HST REBATE ** If Qualified and applicable. Inventory Home Quick Move In Ready 30-60 Days. 4 Bedroom, 2.5 Bathroom, Hardwood Throughout, Smooth Ceilings, Potlights, Stone Counters, ** No Sidewalk and backing onto field of future school.

12 Damara Road Unit Lot 80, Caledon

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