14409 Winston Churchill Boulevard

Welcome to Hilltop Drive. One of Caledon East's most desirable communities. This beautifully updated 4-level side-split offers the ideal blend of modern style, space, and functionality. Featuring four bedrooms and four distinct living levels, this home has been thoughtfully designed to accommodate every stage of family life. At the heart of the home is the stunning renovated kitchen, showcasing an impressive 5' x 9' island, modern cabinetry, stainless appliances, a temperature-controlled wine fridge, abundant storage, and stylish finishes throughout. The adjoining family room is bright and inviting, complete with a walk-out to the patio that seamlessly blends indoor and outdoor living. The upper-level features three spacious bedrooms and a beautifully renovated 4-piece bathroom. On the lower level, you'll find an additional family room with a second walk-out to the yard, a renovated 3-piece bathroom, a fourth bedroom, and a generous laundry room, offering the perfect setup for growing families, multi-generational living, or welcoming overnight guests. The finished fourth lower level provides even more versatile space, with another cozy family room, a beautiful wet bar and seating area, and an abundance of storage space. Summers just got better as you enjoy your own private backyard oasis, surrounded by mature trees, extensive stonework, large garden shed, exceptional privacy, and a beautiful saltwater pool - the perfect setting for entertaining family and friends. Don't miss this incredible opportunity to call this exceptional Caledon East property your forever home!

Need **MASSIVE GARAGE SPACE** (nearly 2500 sq ft) without the price tag of a mansion? This rare find offers exactly that - plenty of room for your workshop, vehicles, or toys, without the burden of an oversized, expensive home (you have the option to expand on this home if you wish). And with Caledon now permitting garden suites, this rare find may offer the exciting potential to convert that garage into a separate residence. Nestled on just under an acre and surrounded by mature, towering trees, this bungalow offers privacy, space, and peaceful country living. For a change of pace, enjoy quiet mornings or evening drinks on the stone front patio, taking in the tranquil rural views. Inside, you'll find a functional layout with town water and natural gas already in place, offering a country setting with city convenience. The 3rd bedroom has been converted into a convenient home office (convert it back if you like), while the kitchen offers potential for expansion into either the living room or the spacious laundry area. Love entertaining? The large, covered porch ensures your BBQs go on, rain or shine. The basement, featuring above-grade windows, invites natural light in and is ready for your open-concept design. Perfect for the weekend warrior, hobbyist, or anyone in need of SERIOUS GARAGE SPACE - this is the needle in the haystack you've been searching for. Don't miss out - come take a look!

On a quiet stretch of The Grange Side Road, this renovated Caledon retreat sits on 1.12 acres, offering privacy, light-filled living, and space to slow down. Located in one of Caledon's most sought-after rural neighbourhoods, this thoughtfully updated 3-bedroom, 2-bath side-split blends modern comfort with the ease of country living. Inside, the home has been completely refreshed with new white oak flooring throughout, a brand new kitchen with new appliances, new washer and dryer, and fully renovated bathrooms, all anchored by a bright, functional layout filled with natural light. The living room is warm and inviting, while the dining room flows seamlessly outdoors to a new patio with pergola-perfect for summer dinners and relaxed evenings. The spacious bedrooms offer comfortable retreats, and the large rec room features a cozy wood burning fireplace, creating an ideal space to unwind. Outside, the extra-deep lot is framed by mature trees and offers endless room to roam, entertain, or garden, all while enjoying the peace and privacy that define this exceptional setting. The home also features updated windows, a recently updated roof, and a 2-car garage. Set among Caledon's most beautiful rural landscapes, close to great schools, skiing, hiking trails, golf, equestrian facilities, and a charming mix of cafes, restaurants, and local shops, this is a lifestyle address that feels both elevated and effortless. A truly special property in one of Caledon's most desirable neighbourhoods. A home that feels as good as it looks.

A Storybook Country Escape in the Heart of Caledon! Tucked among mature trees and rolling hills, this one-of-a-kind country retreat offers the perfect blend of character, privacy, and outdoor living. Set on just over an acre, the property feels worlds away from the hustle of everyday life, yet remains conveniently close to charming villages, trails, ski hills, and local amenities. Inside, warmth and authenticity greet you at every turn. Soaring beamed ceilings, wide plank floors, and a stunning stone fireplace create an atmosphere that is both inviting and unforgettable. The spacious living and dining areas are designed for gathering with family and friends, while large windows frame beautiful views of the surrounding landscape. Upstairs, the primary suite is a peaceful sanctuary with its own sitting area and direct access to the backyard oasis. A third-level loft and additional bedroom provide flexible space for guests, a home office, creative studio, or quiet retreat. Outside is where this property truly shines. Wander along flagstone pathways through established perennial gardens, spend summer afternoons lounging by the pool, and gather around the firepit under a canopy of stars. The detached workshop offers endless possibilities for hobbyists, artists, gardeners, or extra storage. Whether you're searching for a full-time residence or a weekend escape, this remarkable property offers something increasingly difficult to find - a home with soul, surrounded by nature, where every season brings a new reason to fall in love.

PUBLIC OPEN HOUSE SATURDAY SEPTEMBER 5th 1-4PM. Welcome to this beautifully maintained bungalow offering the perfect blend of comfort, convenience, and exceptional outdoor living. Designed for effortless single-level living, this home features 3 bedrooms, 2 bathrooms, and multiple walkouts that create a seamless connection between the interior and the stunning surrounding landscape. Expansive windows fill the home with natural light while showcasing picturesque views of the beautifully landscaped grounds. The delightful kitchen is sure to impress with high-end appliances, granite countertops, and quality finishes. The inviting great room features hardwood flooring, a cozy gas fireplace, and walkouts at both ends, making it ideal for entertaining or simply enjoying the tranquil setting. The spacious primary suite includes a walkout to the deck, custom closet organizers, and built-in shelving. A finished laundry room adds everyday convenience. Step outside to your own private retreat, complete with extensive multi-level decking, lush perennial gardens, a peaceful stream, and mature trees. Unwind in the hot tub, indulge your green thumb, or enjoy hobbies in the detached heated garage with loft. A combination garden shed with dedicated kayak and bike storage provides additional functionality .Notable updates include a commercial-grade steel roof, a new furnace (2025), Garage roof 2026 and an automatic standby generator for added peace of mind. Offering refined interior finishes and spectacular outdoor spaces, this exceptional property is ideal for those looking to downsize without sacrificing quality, privacy, or lifestyle.

Welcome to 1510 Station Road, a beautifully updated home in the heart of Cheltenham, set on a rare 0.344-acre lot (~15,000 sq. ft.) surrounded by gardens, mature landscaping, and outdoor living spaces designed to be enjoyed year-round. Offering updated 4 bedrooms & 2 baths, this home blends historic character with modern comfort. Over $250k has been invested in thoughtful improvements, including a stunning fully renovated Primary Ensuite with walkout access to the gardens, featuring a custom double-sink vanity & freestanding soaker tub. The home also features custom solid wood built-in cabinetry throughout, providing exceptional storage and craftsmanship rarely found. Recent upgrades include a new roof and soffits (2021), updated electrical, plumbing & vapour barrier (2014), and wood siding (2022). The renovated kitchen combines functionality and style with a cathedral ceiling, custom cabinetry, reverse osmosis water filtration, new appliances (fridge, convection oven & microwave - Dec 2025), and a double-drawer dishwasher for added flexibility, savings & convenience when entertaining. Second-floor laundry includes a new stacked washer and dryer (Dec 2025) and a rough-in for a future bathroom. The private retreat gardens feature multiple outdoor spaces including a zen garden, firepit area, gazebo, large back deck, front patio, and an above-ground pool. A former chicken coop offers additional flexibility and potential for conversion into a sauna, studio, or hobby space. The barn and office area is a standout feature, offering extensive storage, two workshops, and a heated office-ideal for entrepreneurs, tradespeople, artists, hobbyists, or anyone working from home. Located within walking distance of parks, trails, river tubing, hiking, cycling, and other outdoor activities, this is a rare opportunity to own a move-in-ready property that offers character, functionality, and a true village lifestyle in one of Caledon's most charming communities.

Escape the hustle without sacrificing convenience in this 3 bed + office, 2 bath family home, ideally situated in one of Caledon's most desirable locations. Offering the perfect combination of privacy, space, and accessibility, this hidden gem is less than an hour from the city, making it an ideal choice for commuters seeking a peaceful place to call home Surrounded by mature trees and lush perennial gardens, the beautifully landscaped property offers exceptional curb appeal and a welcoming outdoor retreat. An extended paved driveway provides ample parking and leads to both the attached double-car garage, complete with a brand-new garage door, and a spacious insulated detached garage with natural gas-perfect for hobbyists, car enthusiasts, or additional storage. A garden shed completes this thoughtfully designed property. Inside, you'll find a bright, functional layout with generously sized rooms designed for comfortable everyday living. The home features three spacious bedrooms plus an additional office/bedroom on the lower level, along with two full bathrooms to accommodate a growing family. The inviting eat-in kitchen offers a nice workspace and opens seamlessly to the formal dining room, where a walkout leads to the deck and overlooks the private backyard. Whether you're hosting summer barbecues, gathering with family, or enjoying your morning coffee, the indoor-outdoor flow makes entertaining effortless. The expansive main-floor living room provides a warm and welcoming place to gather, while the oversized lower-level family and games room offers endless possibilities for recreation, a home theatre, or a children's play area. Upgraded windows upstairs and upgraded insulation provides improved energy efficiency. Low property taxes is an added bonus.This is a property where your family can grow, entertain, and create lasting memories for years to come.

Beautifully renovated between 2022 and 2023, this charming 3-bedroom, 1-bathroom detached bungalow is ideally located in the heart of Caledon Village, just a short stroll from quaint shops, schools, and local amenities. Set along a well-traveled main road, the home occupies a versatile lot surrounded by both residential and commercial properties. Its high-visibility location offers unique potential, ideal for buyers seeking convenience, strong curb appeal, and the possibility of a home-based business (subject to municipal approvals). A modern glass railing and patterned concrete steps lead to a stylish open-concept main floor. The inviting living area features an electric fireplace with a decorative mantel, adding warmth and elegance. The chef-inspired kitchen boasts Dacor stainless steel appliances, quartz countertops, porcelain backsplash, a center island, a coffee nook, a spice rack, and a bright bay window. The adjacent dining area includes a walk-out to a fully fenced backyard with a newly installed privacy fence. The main level includes two well-proportioned bedrooms with large closets and built-in organizers, along with a beautifully updated 3-piece bathroom. The upper-level primary bedroom offers a walk-in closet with custom organizers, built-in shelving, and a cozy sitting area. The partially finished basement adds further potential, with space for a fourth bedroom and a large recreation room. Additional features include a powered detached garage, a generous lot with a 2022-installed hot tub, and driveway parking for up to 8 vehicles.

Welcome 26 Marion St. . Beautiful Renovated and Upgraded Home, Great Open Concept Feel. Engineered Hardwood Flooring Throughout. Lots of Natural Light, Well Landscaped Mature Grounds, Great Kitchen Layout, 3 Exceptional Bedrooms, The Lower Level Has Cozy Recreation Room With Gas Fireplace, Washroom and Laundry Room. Fantastic Storage Space. Relaxing Backyard With 2 Garden Sheds, Mature Garden With Extensive Landscaping. An Excellent Family Home ! See Attached List of Upgrades & Renovations. Heated Garage

Nestled in the highly desirable, family friendly Mono-Mills community of Caledon, this beautifully updated detached raised bungalow is the family home you've been waiting for! Set on an expansive, exceptionally private yard surrounded by mature trees, lush landscaping & a garden shed, this property offers the perfect blend of comfort, space, privacy & modern updates. Step inside & you'll immediately appreciate the warm, inviting atmosphere & thoughtful renovations throughout. This home features 5 bedrooms & 2 beautifully updated bathrooms, making this the perfect property for growing families. The bright, open living room showcases a stunning bay window that fills the space with natural light, while gleaming hardwood floors & pot lights create a polished yet welcoming feel. The recently renovated kitchen is truly the heart of the home, featuring gorgeous granite countertops, a large island/breakfast bar, beautiful cabinetry & stainless- steel appliances. It's the perfect space for preparing family meals, entertaining guests or gathering together at the end of the day. The spacious dining room opens directly to the backyard , making indoor-outdoor entertaining effortless. The main floor offers 3 generously sized bedrooms, while the lower level provides 2 additional bedrooms, a beautifully renovated bathroom & an expansive recreation area that gives your family all the room it needs to relax, play & entertain. The lower level has been extensively renovated, including a brand new heat pump & furnace installed in 2025. Step outside & discover your own private backyard retreat. The large yard provides plenty of room for children to play, family gatherings, gardening and summer entertaining. Nearby parks, playgrounds and a basketball court are just steps away, offering an incredible setting for an active family. This is more than just a house-it's the complete family package with room to grow and all come together in one exceptional perfect property.

Come and experience what Spring is like in Alton with peepers peeping, ducks, geese, red-wing blackbirds, swans, deer, and wildlife! Elegantly perched on the hill, overlooking the lower Mill Pond, is this charming 3-bed, 1.5 bath, stone residence, known as the Algie Family House, with steep gable roofs, in the Victorian Gothic Style. Entrenched in area history, this home was once home to the parents of William Algie, known for constructing the Algie Family home, the neighboring red brick, William Algie House, and the stone mill complex, which operated as, The Beaver Knitting Mill, in 1881, where the Alton Mill currently stands, revitalized today. Comprised of the same local limestone as the Alton Mill, this home exudes warmth and character, sides, & backs to the forest, and sits on a mature .63 acre lot with southerly views. A covered side porch leads to a large Mud rm. Eat-in country Kitchen enjoys views over the b/yard & forest, home to many deer, turkeys, birds and wildlife. Intimate Family rm has forest views & a wood-burning fireplace. Dining open to the Sunroom w/ walkout to the yard. Large formal Living w/ hdwd flooring & large picture window as a focal point. 2nd level has a large walk-in linen. Primary w/ large walk-in closet. Bed #2 could also be used as a Primary w/ hdwd flring, a vaulted ceiling, a walk-in closet with built-in organizers & overlooks the pond. Bed #3 has laminate flring & o/looks the pond and grounds. Enjoy quaint restaurants, craft breweries, farmers markets, coffee shops, walking to neighbourhood parks, the bike pump track, the Alton Public School, the Caledon library, and nearby hiking trails and conservation areas with streams & waterfalls. Alton is a small village in Caledon, home to the Millcroft Inn & Spa, the Alton Mill Arts Centre, Hill Academy, TPC Toronto Golf course at Osprey Valley & more! All major shopping amenities in nearby Orangeville.1-hr to TO.

Nestled in the sought-after Mono Mills community, this spacious 5-level backsplit offers an incredible combination of space, flexibility, and opportunity with 2,852 sq. ft. of finished living space. Featuring 4+1 bedrooms, 2 bathrooms, and two fully equipped kitchens, this home is perfectly suited for multi-generational living, extended families, or buyers looking to offset their mortgage with potential income from the fully finished lower level with its private separate entrance. Designed with functionality in mind, the unique split-level layout provides multiple living spaces for every stage of life. The bright main level offers generous principal rooms, while the lower levels expand into a spacious recreation room, family room, second kitchen, and additional bedroom-creating the ideal setup for in-laws, adult children, or guests. Car enthusiasts, hobbyists, and fitness enthusiasts will appreciate the double car garage plus the bonus finished space, ideal as a private home gym, studio, office, or the opportunity to extend the existing garage into the workshop you've always dreamed of. Step outside to your private backyard, where a covered porch creates the perfect place to enjoy your morning coffee or unwind at the end of the day. With the option to easily screen in the porch, you can create a three-season outdoor living space and enjoy the peaceful setting in comfort while overlooking the backyard. Perfectly positioned in one of Caledon's most desirable communities, this home is a commuter's dream, offering quick access to major routes while maintaining the charm and tranquility of Mono Mills. Whether you're searching for a home that grows with your family, accommodates multiple generations under one roof, or provides exceptional flexibility and income potential, 9 Palace Street delivers a lifestyle that's hard to find.

A CHERISHED HOME, READY FOR ITS NEXT CHAPTER. This solid 3-bedroom bungalow in desirable South Hill has been a cherished home, lovingly looked after for many years, and is now ready for its next owner. This home offers a great foundation and the opportunity to make it your own. Features include a spacious family-sized eat-in kitchen, two bathrooms, including a 3-piece ensuite, a double attached garage, a main floor laundry room and a separate entrance. The original 3rd bedroom has been converted into a living room area and can easily be converted back to a bedroom, offering flexibility for your needs. The home is ready for updating, but there's no need to do it all at once. Move in, enjoy the space, and make improvements as your plans and budget allow. Choose your own finishes and updates while adding value along the way - without paying a premium for someone else's renovation choices. The walk-out basement features an open recreation room with excellent potential for a secondary living space. The private backyard has no neighbours behind. Located on a quiet street close to schools, churches, and parks.A great home, a great location, and a great investment opportunity.

Welcome to 50 Hilltop Court, tucked away on a quiet cul-de-sac in a sought-after Bolton neighborhood and ideally located next to Foundry Park. This well-maintained raised bungalow offers a fantastic combination of privacy, location and comfortable living, with easy access to the Humber River, Edelweiss Park, HVHT trails and downtown Bolton. The main level features hardwood flooring, three bedrooms and a bright, functional layout, while the lower-level family room offers a warm and inviting space complete with a wood-burning fireplace and custom cabinetry. The home has been exceptionally cared for, with a newer furnace, on-demand hot water and a freshly paved driveway. Outside is where this property really stands apart. The private, fully fenced and beautifully treed backyard feels like your own secluded retreat, surrounded by established, low-maintenance perennial gardens, mature greenery, abundant birdlife and even the occasional visiting deer. With parking for six vehicles, an attached garage and one of the most private settings on the court, this is a rare opportunity to enjoy peaceful living while still being just minutes from everything Bolton has to offer, with convenient access to the GTA.

Charming Heritage Gem with Professional 20*24 workshop Located Right In The Heart Of Caledon Village. Home Offers Three Bedrooms . This Home Offers Open Concept Layout With Three Bedrooms, 2 Bathrooms, Large Living Room, Kitchen, Main Floor Office, Insulated 20X24 Workshop. Huge Lot With A Lot Of Potential In A Prime Location. Location Between Orangeville And Brampton. Easy Access To Hwy 410. Current Tenant Pays $2500+Garage Rented out separately $600 Monthly .