Rural Caledon Homes for Sale

Rural Caledon Homes for Sale

Welcome to Rural Caledon, Ontario, a picturesque and tranquil haven that perfectly blends the charm of country living with the convenience of city access. Nestled in the heart of the Peel Region, Caledon is renowned for its stunning landscapes, rolling hills, and lush greenery, making it an idyllic retreat for those seeking a serene lifestyle away from the hustle and bustle of urban life.

Rural Caledon boasts a rich tapestry of nature, with an abundance of parks, trails, and conservation areas. Residents can indulge in outdoor activities such as hiking, cycling, and horseback riding, all while soaking in the breathtaking views of the surrounding countryside. The area is also home to a vibrant community, featuring local farmers' markets, charming boutiques, and delightful eateries that celebrate the region's agricultural heritage.

For those considering a move to this enchanting area, there is an array of homes for sale that cater to diverse lifestyles and preferences. From sprawling estates with breathtaking views to cozy cottages surrounded by nature, Rural Caledon offers a variety of properties that embody the essence of country living. Many homes are situated on generous lots, providing ample space for gardens, outdoor entertaining, and family gatherings.

Whether you are looking for a peaceful retreat or a place to grow your family, Rural Caledon is a community that promises a fulfilling lifestyle. Embrace the tranquility and charm of this beautiful region, and discover the perfect home that awaits you in Rural Caledon, Ontario. Your dream home is just a visit away!

Newest Rural Caledon Homes for Sale

$954,000
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
$2,795,000
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
$2,499,000
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
$979,990
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
$1,599,000
7 Beds ⋅ 6 Baths ⋅ W13768250 MLS
Showstopper! Welcome To This Fully Upgraded Corner Home In A Prime Caledon Location, Offering3,224 Sq. Ft. Of Above-Grade Living Space Plus Two Finished Basement Apartments. With Over$350K Invested In Upgrades, This Home Features A Striking Stone And Brick Exterior, Approximately $90K In Professional Landscaping, And Full Interlocking Across The Front, Around The House, And Throughout The Entire Backyard. The Large Rear Deck And Front Porch Feature Glass Railings, While Exterior Pot Lights Add Beautiful Curb Appeal. The Bright, Spacious Interior Offers 9-Ft Ceilings On The Main Floor, Smooth Ceilings, Pot Lights & California Shutters Throughout, Large Windows, And An Abundance Of Natural Light. No Carpet Anywhere, With Hardwood Flooring And Wood Staircases Throughout, Including Both Staircases. The Upgraded Two-Tone Kitchen Features Upgraded Countertops, Upgraded Backsplash, And An Upgraded Custom Range Hood. Additional Main-Floor Highlights Include A Formal Dining Room And Gas Fireplace. The Primary Bedroom Offers Two Walk-In Closets And A 5-Piece Ensuite, While Every Additional Bedroom Upstairs Features Ensuite Access. Approximately $100K Was Invested In The Finished Basement, Complete With A $15K Separate Side Entrance From The Builder. The Basement Includes One 1-Bedroom Apartment And One 2-Bedroom Apartment, Each With A Separate Kitchen, Full Bathroom, And Laundry. A Double-Car Garage And 6 Car Driveway Provide Parking For 8 Vehicles. A Beautifully Finished, Move-In-Ready Home Offering Luxury, Space, And Versatility Inside And Out. **Legal Basement Apartment**

1 Breckonwood Street, Caledon
$3,450,000
6 Beds ⋅ 5 Baths ⋅ W13767138 MLS
The Beech House stands well back on 2.55 wooded acres, screened from the road. A modern house of more than 4,000 square feet, rebuilt from the studs out to the tree line - over a million dollars of renovation since 2020. A planted courtyard leads to an entry walled in glass. Inside, an open staircase climbs beneath an atrium that pours daylight into the centre of the house. The kitchen anchors the main floor with a long centre island, wall ovens and a sunlit breakfast area. The living room lies beyond, opening to a screened-in covered porch with a pizza oven. A few steps down, the sunken family room. Set on its own, a formal dining room with bar. Three bedrooms occupy the main level, one with a private ensuite - a full life on one floor, should it suit. Above, the primary suite: banks of closets, a spa ensuite with double vanities, freestanding soaking tub and separate shower, and a private balcony in the treetops. A fifth bedroom completes the level. Engineered hardwood and tile throughout; two baths heated underfoot. The grounds are the revelation. A stone terrace runs along the back of the house, with a pergola for long dinners at one end and a hot tub, cold plunge and barrel sauna tucked into the trees. Stepping stones cross the lawn to a circular fire pit terrace. Past the gardens, at the far edge of the lawn, a pond with a fountain sits against the woods. Above the detached garage, a self-contained guest suite with its own entrance: bedroom, bath, living room, dining area and kitchen which is turn-key and furnished. For those tempted to take the look along with the house, select furnishings can be available for purchase. The essentials are handled - furnace 2025, house A/C 2021, guest suite A/C 2026, Culligan UV, softener and reverse osmosis, insulated crawl space, EV charger compatible outlet, Lorex cameras, driveway 2024, culvert 2026. Minutes from Orangeville and the Caledon trails, and quiet the moment you turn in off the road.

3285 Beech Grove Side Road, Caledon
$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
$1,499,000
4 Beds ⋅ 3 Baths ⋅ W13766052 MLS
Welcome To Your Forever Home with 3650 Sq.ft total living space. Discover The Perfect Blend Of Country Charm, Modern Luxury And Tranquility In This Beautifully Renovated 3+1 Bedroom Ranch-Style Bungalow, Set On Approximately 1.85 Acres With A Private Pond And Directly Backing Onto The Caledon Trailway. Surrounded By Nature And Offering Exceptional Privacy, This Rare Property Is Truly One Of A Kind.Step Inside To A Bright, Spacious And Thoughtfully Updated Interior Featuring Stylish Finishes, Pot Lights And Large Windows Throughout, Allowing An Abundance Of Natural Light To Fill The Entire Home. The Gorgeous Kitchen Is Designed For Both Everyday Living And Entertaining, Featuring Quartz Countertops, A Centre Island, Stainless Steel Appliances, Pot Lights And A Convenient Combined Breakfast Area. The Separate Living Room Is Bright And Inviting, While Spacious Bedrooms With Custom Closets Offer Comfortable And Functional Retreats For The Entire Family.The Finished Basement Provides Valuable Additional Living Space And Features Laminate Flooring, Skylight And Pot Lights, Making It Perfect For A Family Room, Recreation Area, Home Office, Gym Or Entertainment Space.Extensively Updated With Numerous Recent Improvements, Including Iron Filter And Heat Exchanger (2026), Well Water Pump (2025), Sump Pump (2024), Water Softener (2020), Septic Bed (2021), Paved Driveway (2021), Interlocking At The Front Of The Home, Patio (2021), Gutters, Soffits & Fascia (2021), All Doors & Windows (2021) And Garage Doors (2021).Enjoy Outdoor Living At Its Finest With Expansive Grounds, A Private Pond, A Beautiful Backyard Gazebo And Direct Access To The Caledon Trailway. A Truly Exceptional Property Offering Space, Privacy, Modern Updates And An Unparalleled Natural Setting. Move In, Unwind And Enjoy The Peaceful Country Lifestyle You've Been Waiting For!

16072 The Gore Road, Caledon
$2,498,000
5 Beds ⋅ 3 Baths ⋅ W13764100 MLS
Private 24.9 acres across from the Paintbrush Golf Course, positioned high on Caledon's Escarpment, this custom, architect-designed 4+1 bed, 2.5 bath has beautiful curb appeal on a park-like, idyllic setting and features country views from every window, sun all day in the south-facing backyard & in-ground pool, rolling hiking trails w/ nature in abundance (turkey, deer, songbirds), and Toronto city skyline views beyond the mature trees. The main level features oak-pegged flooring & crown moulding. Living w/ French doors & wood-burning fireplace framed w/ a pine hearth & surround. Bright & spacious two-toned Kitchen is warm & inviting, w/ granite c-tops, travertine b/splash, center island w/ b-bar is open to the Family w/ a propane gas fireplace, south-facing views, and a sliding-door walk-out to the pro-landscaped pool & patio area. The Primary features an elegant 5-piece ensuite w/ pocket door, skylights, in-floor heating, a glass shower, bidet, soaker tub & long country views. If you look closely, you may even spot the CN Tower through the trees in the distance! Bedrooms 2, 3 and 4 have closets, enjoy beautiful views & share a 4-piece bathroom w/ skylights. Bedroom 5 is in the partially fin bsmt. A Breezeway/Mud rm offers additional access to the home & backyard. It leads to an unfin/uninsulated rm w/ garage access, with potential for workshop, gym, storage or bonus rm! Daikin Heat pump (2020). Enjoy local quaint restaurants, arts centers, craft breweries, farmer's markets, coffee shops, nearby conservation areas, the Caledon Trailway, the Bruce Trail (across the street!), and the Caledon Ski Club. For golf enthusiasts, this property is steps to the Paintbrush, 10 mins to the Pulpit Club, and is 20 minutes to the TPC Toronto at Osprey Valley. There is paved road access to major arteries for ease in commuting to the city or to the north. Enjoy being a 5-min drive to Caledon East, 20 mins to Orangeville & a 1-hour drive to TO. A wonderful central location!

4845 Escarpment Side Road, Caledon
$1,799,000
4 Beds ⋅ 4 Baths ⋅ W13761862 MLS
Live the waterfront lifestyle year-round-just 30 minutes from the GTA! Set on 2.36 private acres with over 300 ft of shoreline on exclusive Green Lake, this exceptional full-time residence delivers the feel of Muskoka without the long drive. Green Lake is a private, spring-fed lake with crystal-clear water, depths of approx. 60 ft and trout and bass-perfect for swimming, boating, fishing and four-season enjoyment. The impressive post-and-beam log home blends timeless character with everyday comfort, creating a warm and inviting retreat designed for full-time living. A heated and insulated detached garage/workshop, charming guest log bunkie with full foundation and 3-pc bath, plus a backup generator add flexibility and peace of mind. Outside, professionally landscaped grounds and flagstone walkways lead to a spectacular lakeside setting complete with private sandy beach, gazebo, dock and outdoor kitchen-ideal for summer entertaining, quiet mornings by the water and unforgettable evenings under the stars. Just minutes from TPC Toronto at Osprey Valley, The Pulpit Club, Caledon Ski Club and miles of scenic trails, this property offers the rare combination of privacy, recreation and convenient access to the city. More than a weekend escape, 143 Green Lake Rd is a true year-round home where every season brings something to enjoy and generations can gather for years to come.

143 Green Lake Road W, Caledon
$3,950,000
6 Beds ⋅ 5 Baths ⋅ W13761544 MLS
Among the finest homes in Caledon. Set high on a hill across nearly 14 acres, surrounded by mature forest, where wild English gardens meet the clean, sharp lines of a gorgeous modern farmhouse. Private, and entirely its own. Completed in 2022 and built to hold the light and the landscape in equal measure. At the centre of the home, an open-concept kitchen, living and dining space anchored by a statement fireplace and wrapped in floor-to-ceiling corner windows that pull the forest inside from sunrise to last light. The kitchen balances marble, warm wood tones and custom detailing with luxe Fisher & Paykel appliances. A beautiful pantry and custom wine room sit just beyond. Views from nearly every room. The ideal family home. A handsome home office with custom built-in bookcase and rolling ladder, perfect for working from home. Off the kitchen, a mudroom and laundry connect to the two-car garage, with a dedicated dog wash. Upstairs, the primary reads as its own wing. Walk-out balcony, generous walk-in closet, five-piece spa-like ensuite. Designed with the ever-growing family in mind, the floor plan offers 4+2 bedrooms and 5 bathrooms, every bedroom with its own ensuite, and a main floor play room with the flexibility to become a co-primary suite. Below, a full basement with oversized window wells that bring daylight right through the lower level. Newly landscaped with professionally designed gardens and plantings, irrigated throughout. A fully fenced backyard made for dogs, kids and long summer nights. A handcrafted Sip Sauna, built to traditional Finnish standards, sits alongside a wood-burning hot tub overlooking the lush lawn. The ideal weekend escape, without leaving home. A modern farmhouse with the soul of a country house, and the craftsmanship to match.

3045 Highpoint Side Road, Caledon
$2,144,000
5 Beds ⋅ 4 Baths ⋅ W13747140 MLS
Timeless Character, Exceptional Space & 2 Acres of Privacy. Discover the possibilities in this stately, all-brick residence, thoughtfully designed and built by its original owners. Offering over 5,000 sq. ft. of living space, this substantial home features a spacious, exceptionally well-planned layout with a natural flow that provides an ideal foundation for a seamless modern update. The main level features a welcoming family room with a striking marble fireplace and walkout to the deck, overlooking the expansive backyard. Upstairs, four generously sized bedrooms include a primary retreat with its own marble fireplace and a large ensuite, currently roughed-in and ready for completion to suit your vision. The lower level adds even more versatility, with a walkout to the breathtaking, park-like two-acre property, offering an incredible sense of privacy, serenity, and connection to nature. A fifth bedroom and bathroom on this level provide excellent space for guests, extended family, additional living accommodations. A lovely, updated lower-level kitchen provides the perfect foundation for a potential in-law suite or additional living space. While this home requires renovation and modernization, the underlying quality, generous proportions, thoughtful floor plan, and extraordinary setting present a rare opportunity to create something truly special. And then there's the location. Just minutes from Caledon East, you'll enjoy easy access to local amenities, schools, parks, the recreation centre, arena, swimming pool, shops, and more - all while coming home to your own private two-acre retreat. A remarkable opportunity to transform a solid, spacious family home into your dream estate in one of Caledon East's most desirable settings.

11 Prince Andrew Drive, Caledon
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