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 above-ground 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 (but you can always add onto this one yourself). 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. 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!

Discover your ideal retreat in this remarkable property set on over an acre of beautifully landscaped grounds, featuring a tranquil pond perfect for irrigating your lawn and garden. This charming 3-bedroom, 1-bath residence offers a separate entrance from the basement to the garage, ensuring convenience and privacy.Enjoy the peace and quiet of rural living while being conveniently located near the upcoming 413 highway, making commuting a breeze. With plenty of parking and endless potential to make this space truly your own, you won't want to miss out on this gem!Book your private showing today and explore all the possibilities this unique property has to offer! Don't let this opportunity slip away!

Welcome to this exceptional Caledon property offering great privacy, surrounded by nature, on a spacious lot in the prestigious hamlet of Palgrave. The home is a spacious raised bungalow, thoughtfully expanded with authorized additions, offering approximately 2,679 sq. ft. of comfortable family living space. Set on a beautiful half-acre lot, this home combines a peaceful natural setting yet just 15 minutes to everyday amenities and 35 minutes to Pearson Airport, offering the best of both worlds within the GTA. Outdoor enthusiasts will appreciate nearby Palgrave Conservation Area, Albion Hills Conservation Park, scenic golf courses, and the Trans Canada Trail. The private lot provides ample space for family enjoyment-whether playing outdoors, hosting BBQs on the deck, relaxing in the hot tub, or unwinding under the shade of a red maple tree. The main level features three bedrooms and a beautifully renovated bathroom, along with a combined living and dining area filled with natural light. The updated custom kitchen with Cabico solid maple cabinets flows seamlessly into the rear addition, which includes a sitting area and walkout to the back deck, perfect for everyday living. The fully finished lower level is mostly above grade, allowing for abundant natural light and functioning as a true extension of the home rather than a traditional basement. It features a welcoming main entrance, a large great room ideal for family gatherings, a fourth bedroom, a fully renovated bathroom, and a spacious family room with a stunning real stone gas fireplace. A convenient side entrance provides direct access to the backyard and garage. Additional features include two garden sheds, a Leaf Fitter eavestrough system, new front, garage, and side doors, dusk-to-dawn exterior lighting, mature landscaping, and multiple red maple trees. Lovingly maintained by its proud owners for over 40 years, this property truly has it all. A rare Palgrave opportunity -come and experience it for yourself

Welcome to your very own country retreat, where space, comfort, and a slower pace of life come together. Set on a private one-acre lot and surrounded by mature trees, this bright and inviting 3-bedroom bungalow is the kind of place families grow into and never want to leave. The heart of the home is a thoughtfully designed custom kitchen featuring leathered granite countertops, stainless steel appliances, pot drawers, corner drawers, and a breakfast bar -perfect for everything from busy school mornings to weekend baking. Just off the kitchen, a versatile den offers the ideal spot for morning coffee, a cozy breakfast nook, or a homework and hangout space for the kids. The dining room is ready for family gatherings and holiday traditions, while the spacious living room is filled with natural light by day and offers a cozy place to unwind in the evening. Take note of the stunning maple hardwood floors! The opposite end of the home, you'll find three bedrooms, with vaulted ceilings adding charm and character throughout, and a large 4-piece bathroom. A carpet-free main floor makes everyday living easy. The lower level expands your living space with a welcoming family room for movie nights, a 3-piece bathroom, an additional space ideal for a playroom, home gym, or home office, and a dedicated laundry area. Outside, the lifestyle truly shines. A brand new deck (2025) offers the perfect place to relax and dine, overlooking a peaceful backyard complete with gardens, a fire pit, and plenty of room to run around. It's the perfect place to build the vegetable garden you've always imagined. The powered and insulated 8x12 garden shed adds incredible versatility for hobbies, storage, or workspace. Don't forget, you have plenty of parking space here, in addition to the large two-car garage. Ideally located in Caledon, you're just minutes from the charm of Alton's main street, home to quaint cafés, local restaurants, golf, and art, while still close to all amenities in Orangeville.

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), 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.

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.

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, above ground pool and outdoor living spaces designed to be enjoyed year-round. Upgrades: -Offers 4 updated bedrooms and 2 bathrooms-Over $250,000 invested in thoughtful improvements -Fully renovated Primary Suite with walkout access to the gardens -Fridge, convection oven, & microwave (Dec 2025), Stacked washer and dryer in second-floor laundry (Dec 2025), Wood siding in 2022, New roof and soffits in 2021, Electrical, plumbing, and vapour barrier in 2014. Updated flooring throughout. Reverse osmosis water filtration system. Renovated kitchen with cathedral ceiling and custom cabinetry & double-drawer dishwasher for added flexibility, savings, and convenience -Rough-in for a future bathroom on the second floor -Private retreat gardens with a zen garden, fire pit area, gazebo, large back deck, front patio, and above-ground pool. -Barn and office area with extensive storage, 2 workshops, and a heated office, ideal for entrepreneurs, tradespeople, artists, hobbyists, or anyone working from home. Also includes a former chicken coop with potential for a sauna, studio, or hobby space. -Outdoor lifestyle location within walking distance of parks, trails, river tubing, patio, and an above-ground pool. A former chicken coop offers additional flexibility and potential for conversion into a sauna, studio, or hobby space. Enjoy peaceful Caledon living just minutes from Brampton, Georgetown, Orangeville, Bolton, and Mississauga. This is a rare opportunity to own a move-in-ready property that offers character, functionality, and a true village lifestyle.

Welcome to 150 Connaught Crescent - a beautifully updated detached home on a premium 50 ft lot in sought-after Bolton West, situated on a quiet, family-friendly street just minutes to historic downtown, parks, and schools. This home has undergone extensive renovations, including a full reconfiguration of the main floor, now offering a bright, open-concept layout ideal for modern living, featuring smooth ceilings, pot lights, upgraded flooring, and a redesigned living and dining space filled with natural light. The updated kitchen seamlessly connects to the main living area, while recently renovated bathrooms add a fresh, move-in-ready feel throughout. Upstairs offers a spacious primary bedroom along with three additional well-sized bedrooms and a 4-piece bath, and the partially finished basement provides additional living space, storage, and flexibility. Enjoy a private driveway with garage, mature trees, and a fenced backyard with large deck - perfect for outdoor entertaining. A turnkey opportunity in one of Bolton's most desirable communities.

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.

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.

Charming detached bungalow situated on a generous lot in sought-after Rural Caledon. This 4+2 bedroom, 3 bathroom home offers peaceful country living with excellent future potential. Features include a finished basement with separate entrance, ideal for extended family, in-law suite potential, or additional living space. Bright and functional layout with spacious principal rooms, ample parking, and scenic surrounding views. Conveniently located minutes to Brampton amenities, schools, parks, and major commuter routes while enjoying the privacy and tranquility of a rural setting. Excellent opportunity for end-users, investors, or buyers seeking long-term growth potential in an evolving area.

Welcome to 15 Emma Street in Caledon East. This beautiful century home, built in 1879 in the Victorian Gothic style of the late 19th century, exudes a timeless charm and sense of warmth and welcome, steeped in history. Situated in the oldest section of Caledon East, it still offers the restful quietness of its early inhabitants, along with the amenities of a modern village, access to the Caledon Trailway at its doorstep and Main Street shopping a block away. The location is perfect for retired people, busy career couples or young families, who want to come home to a peaceful environment. As you walk toward the entrance, one of the main features of the house is the two-story bay window and perhaps the cedar tree, which is as old as the house. You enter through a glassed-in sun porch to the spacious L/R and D/R, with high ceilings and crown molding. Flowing from the D/R is a bonus room featuring a bay window and direct access to the porch, which could easily be an office, den or Primary Bedroom. All of these rooms have oak flooring. A door from the L/R leads to the large, country-style kitchen with maple cupboards, original maple floor, pine wainscoting, serving hatch to the dining room and original trap door to the basement. Open to the kitchen is the F/R - skylit and airy with double French doors to a private, wraparound deck with a covered sitting area. The main level has a laundry room with heated floors and a powder room off the kitchen with a door which leads to the composite deck and meticulous gardens. A maple banister welcomes you to the upper level and three bedrooms (one has a shower and vanity ensuite), plus the main bathroom featuring a whirlpool bathtub and a separate shower. Privacy fences and landscaped gardens surround a brick path to the garage, which features a large work bench, built-in cupboards and a storage loft. A generator that powers up the house is sure to please when you need it the most. This is a true gem of a country home!

Exceptional investment or builder opportunity in a high-demand Caledon pocket! This premium ~2-acre parcel (100' x 850' depth) is perfect for end-users, investors, or custom estate builders. The main level features a well-kept 3-bedroom bungalow with separate living/dining rooms and an upgraded kitchen with a coffered ceiling. A fully finished basement with a separate entrance, 3 additional bedrooms, a full bath, and dedicated laundry offers excellent multi-generational or rental potential. The exterior boasts extensive concrete work and a deep, private backyard with mature trees. Enjoy rural privacy with convenient access to Brampton and major highways. Strong upside potential!

Welcome to this beautifully crafted custom-built home nestled in the heart of the charming village of Inglewood. Boasting timeless curb appeal, this elegant two-storey residence offers a perfect blend of comfort, style, and tranquility. Step inside to a grand foyer highlighted by a stunning spiral staircase, setting the tone for the sophisticated interior. The main floor features a large living room, ideal for quiet relaxation, as well as an open-concept dining area complete with an extended server-perfect for entertaining. The well-appointed kitchen showcases a large breakfast bar, abundant cabinetry, quartz countertops, and built-in appliances, making it both functional and stylish. Upstairs, the spacious primary bedroom is a true retreat, featuring a beautiful bay window and a walk-in closet. The luxurious 5-piece bathroom is thoughtfully designed with a separate soaker tub and an oversized standalone shower, offering a spa-like experience at home. The finished basement provides additional living space with a generous recreation room and a large cold cellar, catering to all your storage and lifestyle needs. Outdoors, enjoy a large backyard with a newer deck, ready for your personal touches. Exceptionally private, the property backs onto serene green space - an extension of the Caledon Trail System -offering peaceful views and direct access to nature. Located in a quiet and quaint community, this home is within walking distance to local favourites including coffee shops, a bike shop, spa, and ice cream shop. Just minutes from multiple golf courses and scenic walking trails, this property presents a wonderful lifestyle opportunity for those seeking both relaxation and convenience!!! Some photos are virtually staged.

From the moment you arrive, you'll be captivated by the warmth, character and timeless appeal of this charming Century home, tucked away on a quiet street at the edge of one of Bolton's most cherished and established neighborhoods. Surrounded by mature trees and rich local history, this 3 bedroom, 2 bathroom home offers a peaceful retreat while remaining close to all the conveniences of town. The welcoming kitchen features granite countertops and opens to a bright dining room highlighted by a large picture window. The cozy living room is the heart of the home, complete with a beautiful bay window and gas fireplace with a stunning pine mantle, perfect for curling up on a cold evening. A quaint and intimate family room provides the ideal space for movie nights or quiet afternoons, while the mudroom offers everyday practicality and easy access to the backyard. Outside, discover your own private sanctuary. Backing onto mature trees without neighbors behind, the peaceful backyard offers a tranquil setting for morning coffee, summer barbeques, and evenings spent listening to the sounds of nature. The partially finished lower level adds versatility with a den/exercise room, office, 2 pc bathroom and laundry area, complete with a workshop. Full of character, warmth and small-town charm, this lovingly maintained home offers a rare opportunity to enjoy the beauty of a bygone era in a small little pocket away from the busyness of central Bolton. A truly special place to call home. Come and see for yourself and fall in love with this hidden hideaway.

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 .

Welcome to this beautifully maintained raised bungalow, ideally situated on a generous 95 ft x 121.5 ft lot recently severed in the highly desirable village of Inglewood. Home offers approximately 1,400 sq. ft. on the main level, plus an additional 600 sq. ft. of finished living space in the lower level, this home provides an excellent balance of comfort, functionality, and lifestyle. The main floor features three spacious bedrooms and two full bathrooms, along with a bright open-concept living area filled with natural light and character. Thoughtfully updated finishes, detailed woodwork, and a warm, modern design create an inviting space ideal for both everyday living and entertaining.The fully finished basement includes a large recreation room, a versatile hobby room/workshop conveniently located beside the garage, a dedicated laundry area, and ample storage. An additional unfinished section offers great potential for future customization.Additional highlights include a spacious garage with automatic door opener and direct basement access, a modern kitchen with stainless steel appliances, updated lighting and trim, and freshly painted interiors throughout.The exterior showcases charming stone steps, professional landscaping, and a private rear deck perfect for outdoor enjoyment.Nestled in a picturesque village setting, this property offers the perfect blend of country charm and urban convenience. Ideally located just minutes to Highway 410, approximately 10 minutes to Brampton and 15 minutes to Orangeville, and close to schools, conservation areas, and the scenic Forks of the Credit. Enjoy nearby trails, golf at Osprey Valley Golf Club, and skiing at Caledon Ski Club.Some photographs have been virtually enhanced.