14409 Winston Churchill Boulevard

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.

Amazing Opportunity! 5 Acre treed lot just South of Hwy 9. Full Basement with Rental potential if finished. Workshop: Approx 38ft X 50ft plus several sheds.

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!

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. Come and experience nature in abundance with peepers peeping, ducks, geese, red-winged blackbirds, swans, deer, and wildlife! 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.

It is Beautiful Property to build Custom Home on 2.95 acre property offering 508.28 ft frontage and 270.27 ft depth. Ideal for builders or renovators, with municipal water available and plenty of space for redevelopment. Located minutes Drive to Caledon Town Hall, community center, schools, trails, golf courses, and equestrian facilities. All the appliances, pool equipment and all HVAC system Sold AS IS/WHERE IS.

Space, privacy and timeless charm come together at 58 Wright Crescent, a beautifully situated detached backsplit in one of Bolton's established residential neighbourhoods. Set on an impressive 50ftx150ft. lot with no rear neighbours and surrounded by mature trees, this inviting 3+1 bedroom, 2-bathroom home offers over 2,500sf of finished living space, providing the comfort and flexibility today's families are searching for. Step inside to a welcoming foyer featuring soaring 12-foot ceilings and a skylight that fills the entrance with natural light. The spacious living and dining area boasts 9-foot ceilings, creating an airy, open atmosphere perfect for entertaining and family gatherings. The functional kitchen features a breakfast area, pantry and walkout to the porch, offering convenience for everyday living. Generously sized bedrooms feature large windows and ample closet space, complemented by an updated second-floor bathroom. A separate family room with a cozy fireplace and walkout to the patio provides an inviting retreat for relaxing or entertaining. Outside, the expansive backyard offers exceptional privacy, mature greenery and endless possibilities for outdoor enjoyment, whether hosting summer BBQs, gardening or creating lasting family memories. An attached single-car garage and generous driveway provide parking for four vehicles. Ideally situated in Bolton's welcoming community, close to parks, schools, shopping, restaurants and everyday amenities. Whether you're a growing family looking for room to spread out or a buyer seeking a spacious home on a remarkable lot, 58 Wright Crescent offers an exceptional opportunity to enjoy comfortable living in a peaceful, established setting.

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.

Charming 3-Bedroom Bungalow with a Separate Basement Apartment! Welcome to this fantastic opportunity for homeowners, investors, or multi-generational families! This beautifully maintained 3-bedroom bungalow offers comfortable main-floor living with a fully finished basement featuring its own separate apartment, complete with a private entrance and excellent potential for additional income or extended family living. The main floor offers a functional layout with spacious principal rooms, 3 bedrooms, and plenty of natural light. Downstairs, the separate apartment provides added flexibility and privacy, making this home an ideal option for those looking for income potential without sacrificing space. Great family-friendly home with plenty of possibilities. Live in, rent out, or enjoy the best of both!This is one opportunity you won't want to miss.

Tucked away on a quiet, family-friendly court just steps from downtown Bolton and its walking trails, 115 Meadowvale Court is the kind of place where you can finally design the home you've been picturing. The lot is approximately 60 x 118 feet, with a private, peaceful backyard ready for gardens, summer evenings, a play space, or whatever you can dream up. A double car garage and private double driveway provide ample parking for four vehicles. This 4-bedroom backsplit offers just over 1,800 sq ft of living space with great bones and a layout that works beautifully for a growing or extended family. The main level features a spacious living and dining room with large bay-style windows and hardwood floors, plus a galley-style kitchen with a window over the sink, just waiting to be reimagined into the main floor of your dreams. A few steps down, a huge family room with an authentic stone gas fireplace walks out to the backyard. You'll also find a laundry room, a 2-piece bath, and a side entrance with easy access to the basement and to a bedroom (or home office), ideal for guests, in-laws, or working from home. Upstairs are three bedrooms and a fresh 3-piece bath. The unfinished basement adds approximately 600 sq ft of open space with large windows, a true canvas for a rec room, gym, or whatever suits your family. Very clean and well cared for, this original home is ready for your cosmetic updates and personal style. Whether you're a family looking to customize your dream home or a contractor ready to put your touch on it, this is a wonderful opportunity in a lovely, established Bolton neighbourhood. Come see the potential!

Discover a Different Pace of Living at 8 Holmes Drive in Caledon! Nestled in the charming Mono Mills community, this detached 1-storey home offers 4 bedrooms, 2 bathrooms, and an inviting opportunity to embrace the beauty of country-inspired living without sacrificing access to everyday conveniences. Offering a refreshing alternative to busy suburban neighbourhoods, this property combines the appeal of detached homeownership with the character and tranquility of Caledon's scenic surroundings. The versatile four-bedroom layout provides flexibility for a variety of lifestyles, whether you need additional living space, a dedicated home office, guest accommodations, or room to pursue your hobbies. Enjoy the best of both worlds with convenient access to Orangeville's shopping, restaurants, services, and amenities, while being surrounded by the natural beauty and outdoor recreation opportunities that make Caledon such a desirable destination. Spend your weekends exploring nearby Island Lake Conservation Area, hiking the scenic trails of Mono Cliffs Provincial Park, or enjoying skiing, golf, and recreation at Hockley Valley Resort. With its distinctive 1-storey design, four-bedroom configuration, and appealing Mono Mills location, 8 Holmes Drive offers an opportunity to enjoy more space, a change of scenery, and a lifestyle that feels a world away from the everyday hustle. More Room. A Different Rhythm. Your Next Chapter Starts Here! SEE ADDITIONAL REMARKS TO DATA FORM

5 Reasons Why You Will Love This Detached 2-Storey Home: 1) The upper floor features a 4-piece bathroom, hardwood flooring and three bedrooms, each offering a window for natural light and a closet. 2) The main floor offers a spacious living room and modern kitchen with smooth ceilings and pot lights throughout. The kitchen is complete with stainless steel appliances and flows seamlessly into the breakfast area, which provides a walkout to the backyard. 3) The backyard offers a true oasis with an in-ground saltwater heated pool, creating the perfect setting for summer enjoyment and entertaining. 4) Enjoy the privacy of a quiet cul-de-sac, along with a double-car garage and a spacious driveway accommodating up to four vehicles. 5) Location Is Close To Shopping, Schools, Parks & Highways!

Welcome to 1 Herriot St., a wonderful opportunity to own a home in the charming community of Palgrave, Caledon. Situated on a quiet, family-friendly street surrounded by the natural beauty Caledon is known for, this property offers a great blend of comfort, privacy and convenience.Enjoy the best of small-town living while remaining within easy reach of major highways, local amenities, schools, parks, trails and everything the surrounding Caledon community has to offer. The area offers a quiet setting, a spacious lot, and plenty of room to enjoy indoor and outdoor living. and a peaceful setting without giving up convenient access to the GTA.Inside, the home offers a welcoming layout with comfortable living spaces and plenty of potential to make the property your own. The outdoor space provides an excellent setting for entertaining, relaxing or enjoying time with family.A fantastic opportunity in a sought-after Caledon location - don't miss your chance to make 1 Herriot St. your new home!

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.

Stunning Bungalow on half Acre in Prime Caledon Location! Private Lot On Paved Road, 10 Mins To Brampton, Georgetown And Cheltenham! All The Work's Been Done Here With Hardwood Floors, Renovated Kitchen & Bath, Bay Windows on main floor, Roof, Furnace & A/C, Baseboards & Trim!. Finished Basement W/Sep. Ent. And 2nd Kitchen, 2nd Laundry, Rec Room, Games Room, Beautiful 3 Pc Bath, Big Cantina! 16'X15' Workshop And A Garden Shed! Bonus Storage Room At Back Of Garage.

Welcome to the Beautiful, Quaint and Quiet Caledon Village. This 1761 SqFt Bungalow sits on a nearly 1 acre (.918) southern exposure lot on a quiet crescent at the natural edge of Caledon Village. Country Living and Village Convenience Combined. 32 Autumn Drive is Spotlessly Clean and Meticulously Maintained. It is has a Practical Layout with Spacious Rooms and Good Separation of Living Areas with Hardwood Under Broadloam. Large Dining and Living Rooms and a Separate Family Room with Gas Fireplace and Walk Out to the Rear Deck. Three Generous Sized Bedrooms and 2 Bathrooms along with a Large Foyer Entrance complete the Main Floor. The Lower Level is Partially Finished with Full Rooms assigned with Electrical, Studs and Plumbing completed. There is a Workshop Area in the Basement and Another Work Shed Space off the Rear of the Large Double Garage. Much More than a Diamond in the Rough, it is a Fully Formed Diamond that just needs a New Setting to Shine to Its Full Potential. Making it a Modern Masterpiece requires only cosmetic changes. Country Living is within reach with this priced to sell home straddling the best of Quiet Country Living and nearby Village Convenience not to mention the commuting distance to the GTA and the all access amenities of nearby Orangeville. Thinking of Country Living with Convenience, 32 Autumn Drive in Caledon Village brings You Home to This Reality. Make Your Move to the Village Today.

Welcome To 175 Allan Dr, A Beautifully Renovated 3-Level Backsplit In One OfBolton's Most Desirable, Family-Friendly Neighborhoods. Turn-Key And Sun-DrenchedThroughout, This Exceptional Home Features 1700+ Sqft Of Living Space, Bright Open-Concept Living, A Chef's Style Kitchen With Premium Finishes, 3 Generous Bedrooms,And 2 Stunning, Fully Renovated Spa-Like Washrooms Designed For Pure Relaxation.The Finished Lower Level Offers Outstanding Versatile Space Ideal For A Cozy FamilyRoom, Home Gym, Work-From-Home Office, Or Media Den. Step Outside Into YourPrivate Oasis: An Expansive, Pool-Sized Lot Offering Endless Potential For A BackyardPool, Custom Patio, Garden, And Outdoor Entertaining. Highlighted By Modern ExteriorCurb Appeal, Expansive Windows, Smooth Ceilings, Upgraded Lighting, And AmpleDriveway Parking With Plenty Of Room For Multiple Vehicles.Located Minutes Away From Top-Rated Schools, Picturesque Parks, Local RecreationCenters, Shopping Plazas, Charming Downtown Bolton, And Major GTA CommuterRoutes. This Turn-Key Gem Delivers The Ultimate Combination Of Luxury, Space, AndUnbeatable Location!

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.

OPEN HOUSE SUNDAY NOVEMBER 8, 1-3PM Now offered well below original purchase price with additional negotiable bonus incentive!!! 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.

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 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.