Step outside to a true backyard escape featuring a heated saltwater pool, charming pool house with bathroom, mature trees, and expansive entertaining areas. With a finished walk-up basement, detached two-car garage, Generac generator, and exceptional privacy-yet minutes to conservation lands, trails, schools and commuter routes-this is a rare opportunity to secure a refined estate in one of Caledon's most coveted communities. Perfect for families or multigenerational living. Book your private showing today. All offers welcome. Inclusions: Jenn-Air Professional Gas Range, S/S Fridge, B/I Dishwasher, Wine Fridge, Stacka
34 pictures
Townhouse
$ 879,000
viewed
Caledon, Ontario
May 30, 2026
With no visible neighbours from the private sunroom addition, this true bungalow with its pleasing, functional layoiut boasts unique flooring throughout created from reconditioned rock elm. The main living space is 1540 square feet, the sunroom addition 240 square feet and the finished lower level is 600 square feet, giving over 2300 square feet of finished space. (Because it's empty, some photos have been virtually staged)
Ideally situated between Caledon Village and Orangeville, the property provides convenient access to a wide range of amenities while still offering a rural
30 pictures
Updated
House
$ 1,725,000
viewed
Caledon, Ontario
GardenGymSwimming poolCellar
2 days + 15 hours ago
Welcome to this beautifully renovated bungalow in the heart of Caledon Village, offering the perfect blend of modern comfort and country charm.
50 pictures
House
$ 1,199,900
$ 1,249,900
4%
viewed
Caledon, Ontario
GardenParkingCellar
6 days + 15 hours ago
Stately 4-bedroom, 2.5-bathroom home sitting on a large lot in Caledon Village! Enjoy abundant driveway parking plus a triple-car garage.
40 pictures
House
$ 949,000
viewed
Caledon, Ontario
Garden
2 weeks + 15 hours ago
The Modern Kitchen Is Equipped With Premium Appliances, Sleek Cabinetry, And A Large Island Perfect For Entertaining. Upstairs, You'll Find Spacious Bedrooms, Including A Luxurious Primary Suite With A Walk-In Closet And Spa-Like Ensuite. Enjoy Relaxing Or Hosting Gatherings In The Comfort Of Your Own Backyard. Located In A Quiet, Family-Friendly Neighborhood Close To Parks, Schools, Shopping, And Amenities, This Home Offers The Perfect Blend Of Comfort And Convenience
41 pictures
Townhouse
$ 849,000
viewed
Caledon, Ontario
GardenDeck
2 weeks + 4 days ago
This beautifully maintained 2-bedroom bungalow showcases true pride of ownership and offers bright, airy living spaces with modern finishes throughout. Stunning landscaped grounds and raised garden beds create impressive curb appeal and lead into a welcoming foyer featuring a skylight, double closet, and elegant French doors opening into the main living area. The open-concept main level is filled with natural light from large windows and features a spacious living and dining room highlighted by a charming bay window. The well-appointed kitchen offers ample space for everyday living and entertaining, with a walk-out to the private back deck overlooking a tranquil green
50 pictures
House
$ 1,680,000
viewed
Caledon, Ontario
2 weeks + 5 days ago
Ft. of beautifully designed living space and the perfect blend of elegance, comfort, and resort-inspired living. From the moment you enter, you are greeted by soaring 9-foot ceilings, hardwood flooring throughout the second floor, designer lighting, & refined modern finishes throughout. The stunning gourmet kitchen is beautifully appointed with granite countertops, stylish backsplash, upgraded stainless steel appliances including a gas stove, and picturesque ravine views. Acustom butler's pantry with wet bar and sink adds both elegance and functionality, creating the perfect space for entertaining. The spa-inspired primary ensuite creates a true luxury retreat featuring heated floors, freestanding soak
50 pictures
House
$ 1,525,000
viewed
Caledon, Ontario
Fireplace
2 weeks + 6 days ago
and sophisticated design by Brookfield Residential, this exceptional 4,550 square foot above-grade residence stands as a benchmark of premium living in Caledon
51 pictures
House
$ 4,500,000
viewed
Caledon, Ontario
GardenFireplaceSwimming pool
3 weeks + 1 day ago
Just outside Belfountain, on nearly 15 acres of Caledon countryside, it is steeped in character and completely its own.
47 pictures
House
$ 1,199,900
viewed
Caledon, Ontario
GardenCellar
Jun 02, 2026
Freshly painted and meticulously cared for, pride of ownership is evident throughout. The professionally finished basement includes a second kitchen with excellent in-law suite capability and endless potential for extended family living or additional space. Situated on a desirable pool-sized lot with ample room to create your dream backyard oasis. Conveniently located close to top-rated schools, parks, shopping, restaurants, and all major amenities. An exceptional opportunity to own a wonderful family home in one of Bolton's most desirable neigh
31 pictures
House
$ 1,599,900
viewed
Caledon, Ontario
FireplaceCellar
Jun 01, 2026
Welcome to 578 Dougall Avenue in the highly sought-after Southfields Village community of Caledon.
5 pictures
Land
$ 849,900
viewed
Caledon, Ontario
May 30, 2026
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
49 pictures
House
$ 2,199,900
viewed
Caledon, Ontario
Swimming poolEquipped kitchen
May 30, 2026
Situated on 29.5 acres of pristine land in the Niagara Escarpment this one-of-a-kind property offers direct access to the Bruce Trail, Credit Valley River, endless opportunities for hiking, fishing, cross-country skiing, and pond skating. Home Features: Chefs Kitchen Dream: Outfitted with a built-in Dacor double oven, Thermador induction cooktop, B/I dishwasher, wine fridge (75 bottles), fridge, upright freezer, and an instant hot water under-sink dispenser system all grounded by heated bamboo and porcelain flooring. Interior Comforts: 1 wood-burning F/P, formal dining room, sun-filled sunroom with W/O to a sunken hot tub, and a spacious games room. 2 Murphy beds. Premium Utility Systems: Reverse osmosis water filtration, water softener, two sump pumps,
41 pictures
House
$ 1,299,000
viewed
Caledon, Ontario
TerraceFireplaceDeck
May 29, 2026
The main level features tile flooring throughout, a formal living and dining room with crown moulding, and a spacious family-style eat-in kitchen with walk-out to the deck, perfect for entertaining or relaxing. The primary bedroom boasts a 5-piece ensuite, accompanied by two additional bedrooms, all on the same level for convenience. The finished lower level offers incredible living space with a separate entrance, making it perfect for an in-law suite or rental potential. It includes a large recreation room with fireplace, a full second kitchen, an additional bedroom with fireplace, and a 4-piece bathroom. The den provides extra flexibil
32 pictures
Land
$ 2,250,000
viewed
Caledon, Ontario
Garden
May 29, 2026
Located on a quiet country road near the Bruce Trail & just 5 minutes to Caledon East amenities, shopping, Rec center, library, farm markets & stores, Come and experience what Spring sounds like in the hills of Caledon with peepers peeping, birds singing, and more!
View photo
House
$ 1,488,000
viewed
Caledon, Ontario
4 Bedrooms
4 Bathrooms
GardenParking
May 27, 2026
Inside, expansive principal rooms provide the ideal backdrop for both everyday living and memorable gatherings.Car enthusiasts & busy families alike will appreciate the extended garage, offering an impressive 24ft depth, perfect for larger vehicles, storage, or workshop setup.Outside discover a backyard retreat! The outdoor kitchen is designed for effortless entertaining. A powered shed adds functionality, & underground irrigation supports a flourishing vegetable garden. luxury with sustainable living! A standout opportunity for families seeking space, and an exceptional sett
50 pictures
Updated
House
$ 1,309,000
$ 1,349,000
3%
viewed
Caledon, Ontario
FireplaceDeckParking
2 days + 15 hours ago
Nestled on a serene, tree-lined 1.03 acre in Caledon, this stunning 3-bedroom, 3-bathroom, residence offers of beautiful living space 2,104 sq.
48 pictures
House
$ 1,899,000
viewed
Caledon, Ontario
Office roomCellar
1 week + 6 days ago
A spacious dining room adds warmth and elegance, while the main floor also offers two bedrooms, a stylish 5-piece bath & a private office ideal for working from home. The upper loft level provides a cozy family room retreat along with a third bedroom and 3-piece bath, creating the perfect separate space for guests or family. The unspoiled basement offers endless potential to customize to your lifestyle needs. Outside, the oversized barn with 100 amp service is a dream for hobbyists, car enthusiasts or anyone seeking the perfect workshop or storage s
32 pictures
House
$ 849,900
viewed
Caledon, Ontario
PatioOffice roomSwimming poolDeckParking
2 weeks + 15 hours ago
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
23 pictures
House
$ 849,900
$ 869,900
2%
viewed
Caledon, Ontario
PatioGarden
2 weeks + 2 days ago
The main level features hardwood flooring, 9-ft ceilings, and an abundance of natural light, creating a warm and inviting atmosphere throughout. The contemporary kitchen is designed with quartz countertops, a centre island, stainless steel appliances, and a stylish backsplash, seamlessly overlooking the living and dining areas. The walk out to the backyard patio is the perfect space for summer BBQs, outdoor dining, or relaxing evenings with family and friends. Upstairs, the spacious primary retreat features a luxurious 5-piece ensuite, walk-in closet, and an additional double closet offering exceptional storage space. The second bedroom includes its own walk-in closet, while the third bedroom is highlighted by an oversized window framed by a vault
46 pictures
House
$ 919,000
viewed
Caledon, Ontario
PatioOffice room
May 31, 2026
Equally suited to a professional office, income-generating rental, or in-law suite. Run your business from home, welcome extended family with real privacy, or generate meaningful rental income. The choice is yours, and the possibilities are genuinely uncommon. Set on a sun-soaked corner lot, the home offers more space, more light, and more possibility than almost anything else on the market, living larger than many detached properties in the area. Upstairs, three generous bedrooms provide a peaceful retreat for the whole family, including a serene primary suite complete with its own ensuite and deep soaker tub. Your own quiet escape at the end of the day. Step outside to enjoy three inviting patios, i
50 pictures
House
$ 2,199,999
viewed
Caledon, Ontario
FireplaceDeck
May 23, 2026
Tucked into the rolling hills of Caledon and surrounded by mature trees, 22 Southridge Trail feels less like a home and more like an escape from the pace
34 pictures
House
$ 1,299,000
viewed
Caledon, Ontario
GardenFireplaceSwimming poolDeckParking
May 23, 2026
Enjoy resort-style outdoor living with a saltwater pool, waterfall, slide, spa/jacuzzi, gazebo seating area, mature trees and wrought iron gate access on both sides. The spacious primary suite features a luxuriously updated ensuite, while two additional bedrooms, a full bath, main floor laundry and direct garage access complete the main level. The bright above-grade walkout lower level includes a second kitchen, large living and dining areas, private bedroom with ensuite, French doors, separate entrance and dedicated laundry ide
49 pictures
House
$ 3,499,999
viewed
Caledon, Ontario
FireplaceDeckEquipped kitchen
May 23, 2026
Designed for both grand entertaining & comfortable family living, this exceptional home showcases high-end finishes, incredible amenities, & resort-style outdoor features. Main level offers approx. 3,480 sqft with 10 ft ceilings & hardwood floors. A grand foyer welcomes you into the spacious Great Room featuring a gas fireplace & skylight. Formal Dining Room impresses with chandelier lighting, pot lights, mood lighting, and a coffered ceiling. Separate Living Room also features elegant coffered ceilings. The gourmet chefs kitchen is truly spectacular, with ceramic flooring, granite countertops & oversized islands, Sub-Zero built-in fridge/freezer, commercial-grade double oven stove, Bosch dishwasher, 3 sinks, wet bar, & walkout to a massive maintenance-free deck installed in 2024. This level also features 4 spacious bedrooms, i
49 pictures
House
$ 3,499,999
viewed
Caledon, Ontario
FireplaceDeckEquipped kitchen
May 23, 2026
Designed for both grand entertaining & comfortable family living, this exceptional home showcases high-end finishes, incredible amenities, & resort-style outdoor features. Main level offers approx. 3,480 sqft with 10 ft ceilings & hardwood floors. A grand foyer welcomes you into the spacious Great Room featuring a gas fireplace & skylight. Formal Dining Room impresses with chandelier lighting, pot lights, mood lighting, and a coffered ceiling. Separate Living Room also features elegant coffered ceilings. The gourmet chefs kitchen is truly spectacular, with ceramic flooring, granite countertops & oversized islands, Sub-Zero built-in fridge/freezer, commercial-grade double oven stove, Bosch dishwasher, 3 sinks, wet bar, & walkout to a massive maintenance-free deck installed in 2024. This level also features 4 spacious bedrooms, i
47 pictures
House
$ 1,099,000
viewed
Caledon, Ontario
GardenDeck
May 23, 2026
This property boast over 70+ trees and expertly landscape perennial gardens creating the perfect amount of privacy and sense of whimsey on this ravine like lot. As you walk into this one of a kind home you are greeted with warmth and attention to details. From the crown mouldings to the high-end kitchen with walk in pantry, no detail was overlooked. Truly an unforgettable feature of this home is stepping out to your large deck, perfect for entertaining overlooking your own piece of paradise. From the main floor just take a few steps to the upper level to a bright and generous primary bedroom, featuring soaring ceilings, spacious walk in closet, and a 5 piece ensuite bathroom. Making your way down to the lower level brings you so much potential with
33 pictures
House
$ 1,269,000
viewed
Caledon, Ontario
GardenFireplaceDeck
May 22, 2026
Enjoy separate living, family, and dining rooms, perfect for both everyday living and entertaining. The cozy family room features a gas fireplace, while the upgraded modern kitchen offers stainless steel appliances, marble countertops, and a functional eat-in layout. The breakfast area provides direct access to a huge covered deck, ideal for BBQs and outdoor gatherings overlooking the beautifully landscaped, stone-finished backyard that feels like your own private summer retreat. The finished lower level includes 2 spacious bedrooms, a 3-piece bathroom, and a convenient kitchenette, making
45 pictures
House
$ 929,000
viewed
Caledon, Ontario
PatioGardenDeck
May 21, 2026
Step inside to discover a warm and welcoming interior featuring updated flooring throughout, complemented by newer windows that enhance natural light. Recent improvements including upgraded insulation, vinyl siding, soffits, fascia, and eavestroughs provide peace of mind and long-term durability. The spacious layout offers comfortable living for families, along with the added convenience of central vacuum. Outdoor living is where this property truly shines. Enjoy your private backyard retreat complete with a rear deck and relaxing hot tub-perfect for unwinding or entertaining. A lower patio area expands your outdoor space, while the expansive double driveway accommodates up to
12 pictures
House
$ 2,403,500
viewed
Caledon, Ontario
Garden
May 21, 2026
174 x 197 Ft Lot, this Stunning Residence Offers over 4,300 Sq Ft of Refined Living Space with i Rare And Functional 5 Bedroom, 5 Bathroom Layout ideal for Multi-Generational Living and Upscale Entertaining. Featuring Impressive Open-To-Above Ceilings, Soaring 10 Ft Ceilings On Main Floor, Hardwood Flooring, Oversized Porcelain Tiles, Coffered Ceilings, Pot Lights & Designer Finishes throughout. Private Main Floor Office with French Doors creates the Perfect Work-From-Home Space while the Separate Formal Living Room with Wet Bar adds Elegance and Flexibility for Entertaining. Chef-Inspired Kitchen features Extended Cabinetry, Quartz Countertops, Walk-In Pantry, Oversized Island & Spacious Breakfast Area overlooking the Backyard. Dramatic Great Room with approx. 20 Ft Ceilings that creates a Grand yet Inviting Atmosphere for Family Gather
