14294 Winston Churchill Boulevard

Tucked away in one of Caledon's most picturesque countryside settings, this enchanting custom built home spans approx4500sqft situated on 7 acres. A fully insulated 1200sqft garage/workshop with loft space provides exceptional flexibility for car enthusiasts, hobbyists, or additional storage. With Orangeville, Erin and Caledon Village a short drive away this property combines rural tranquility with exceptional amenities. The home blends character, architectural significance, and natural beauty into an offering unlike anything else on the market. From the moment you arrive, the home's storybook presence captivates, with a stunning wraparound porch, soaring cedar-clad ceilings, expansive skylights, wood- burning fireplace and an open-concept design. Rich in history, the home showcases beautifully restored beams and posts reclaimed from an 1854 barn in King Township, creating the charm and grandeur of a classic barn interior while offering all the comforts of modern living.Thoughtfully designed layout is ideal for both entertaining and family living. The serene primary retreat offers a magical experience, allowing you to gaze at the stars from the comfort of your bed. Additional bedrooms feature vaulted ceilings, while the versatile third-floor loft is perfect as a guest suite, home office, studio, or children's retreat. Outside, the remarkable grounds offer the perfect balance of open green space and private woodland trails. Ideally situated near TPC Toronto at Osprey Valley, the Caledon Ski Club, premier equestrian facilities, extensive cycling and hiking trails, and local favourites such as GoodLot Farmstead Brewing Co. The new 413 highway will significantly increase the accessibility to the City and beyond. Excellent schools in Belfountain and Alton further enhance its appeal. A rare opportunity to own a truly distinctive estate where history, nature, and modern comfort come together in perfect harmony.

Discover a lifestyle that feels worlds away, yet keeps everything close at hand in beautiful Terra Cotta. Set on a private 1-acre lot just minutes from Georgetown and the GO Station, and a short commute to Brampton and the GTA. This inviting 3+1 bedroom bungalow offers the perfect blend of country charm, convenience and versatility. A long driveway leads to the attached 2-car garage and continues to an impressive detached 3-car shop with heat and hydro-a dream setup for car enthusiasts, hobbyists, collectors or anyone needing serious workspace. Inside, a transformative addition created the heart of the home: a spectacular cathedral-ceiling great room filled with natural light, cuddle your loved ones by the warm gas fireplace, and oversized windows bring the beauty of the outdoors into everyday living. The remodeled kitchen features ceramic flooring, granite counters and a gas stove while the beautifully updated full bathrooms add a touch of everyday luxury with heated floors. Convenient main-floor laundry provides exceptional closet and storage space. The finished basement adds even more room to enjoy, with a spacious rec room and games room designed to keep kids young and old entertained. Step outside and the lifestyle really begins. The Caledon Trail is just a minute away, with golf, skiing, conservation lands, tubing down the Credit river and the charming shops of Terra Cotta all close by. High-speed internet and natural gas are a major advantage removing the uncertainty of rural utility costs .Imagine mornings of sun bouncing through soft dew, birds hopping through the apple trees, afternoons surrounded by flowers as you tend the garden, evenings of resting to the sounds of nature...This is more than a home-it's a pace of life that rewards the soul.

Discover an extraordinary and spectacular 20 acres of land sitting on approximately 400ft frontage on the prestigious Gore Road of East Caledon. Property contains beautiful surroundings: nature, mature trees, and a huge natural pond - very scenic and a much desired lot. Property features 4 + 1 bedrooms, finished basement with a walk-out to the back yard - perfect for entertaining all year round and offering endless opportunities for outdoor activities and relaxation. This property has endless possibilities for future development - even the possibility for two houses! Don't miss out on this rare offering in a sought after area of East Caledon.

2-Storey House On 8-10 Acre Farm, Less Than 1 Hour Escape From Toronto. Estate Homes In The Vicinity. An Oasis Of Tranquility And Peace. Use It As A Farm, Your Home Or Even As A Contractor's Yard. The Existing House Has 3 Bedrooms, And 3 Bathrooms. It Features A Large Inter looking Patio, Some New Windows, A New Bathroom, New Shed (All In 2018). The Property Features A Large Barn (In As Is Condition) With Water Service And Electricity.

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!

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 of everyday life. Set on over 10 acres in the sought-after Forks of the Credit area, this custom bungalow offers privacy, nature, and timeless design in one unforgettable setting. Inside, dramatic vaulted wood ceilings and oversized windows frame peaceful forest views while bringing warmth and character to the entire home. The great room is the showpiece, anchored by a stunning floor-to-ceiling stone fireplace and filled with natural light that shifts beautifully throughout the day. Every room feels connected to the landscape outside. The kitchen and living spaces flow effortlessly toward an expansive deck overlooking the trees, creating the perfect place for morning coffee, evening wine, or quiet weekends surrounded by nature. Here, the soundtrack is wind through the leaves and the occasional crackle from the fireplace. With over 3,100 sq ft above grade, the home offers 3 bedrooms, 3 bathrooms, and a spacious main-floor primary suite designed for comfort and easy everyday living. The unfinished lower level provides endless potential for future living space, a workshop, studio, or customized retreat tailored to your lifestyle. A new Generac generator adds valuable peace of mind, ensuring comfort and reliability year-round. Outside, the beautifully landscaped grounds blend seamlessly into the surrounding countryside, offering a true estate feel just minutes from Belfountain, the Caledon Ski Club, the Caledon Mountain Trout Club, golfing, hiking trails, and the Forks of the Credit. This is the kind of home people leave the city for. Quiet luxury, breathtaking surroundings, and room to finally breathe.

Set on an impressive 2.5-acre corner lot, 4 Wolf Crescent offers an incredible opportunity in one of Caledon's most sought-after areas. With expansive, usable land and uninterrupted views in every direction, this is a place where nature takes centre stage - designed for active, everyday living. Featuring a saltwater inground pool and a tranquil pond, the outdoor space is built for all seasons - summer days by the pool, room for kids to run and play, and winter skating right in your own backyard. With space to host, gather, and move, this property delivers a lifestyle that's hard to find. Inside, the 4-bedroom home has been well loved and is ready for its next chapter. The sunroom, with exposed brick, features a large dining area ideal for family meals, celebrations, and everyday living, all overlooking the property. A separate living space with a stone fireplace offers a comfortable place to unwind. With room to grow and the opportunity to make it your own, the home offers strong potential to evolve with your needs. Thoughtful updates include a new A/C (2025), repaved driveway (2021), 40-year shingles (2016), and a new sump pump. A gas-powered generator provides added reliability, ensuring power when it matters most. A rare opportunity to put down roots and create something truly special in an unforgettable setting.

Client RemarksYour golf clubs, ski boots and paddle board called. They'd like to move to Caledon.Work, live and play. All in one pretty spectacular place. There are homes with backyards. And then there are homes with their own spring-fed pond, nearly 3 acres of forest, and a lifestyle that could give your favourite weekend getaway a run for its money. Welcome to 1 Cedar Drive. Tucked into the rolling hills of Caledon, where the golf is good, the ski hills are close, and coming home feels suspiciously like going on vacation. Beautifully renovated with just the right amount of sophistication, this four-bedroom country home knows how to make an entrance. Think gorgeous hardwood floors, a chef-worthy kitchen dressed in quartz and stainless steel, oversized windows framing the surrounding greenery, and a cathedral-ceiling family room with a fireplace that practically begs for a slow Sunday. There's a dedicated main-floor office, a generous mudroom for all the gear that comes with country life, and a primary suite with a five-piece ensuite, walk-in closet, and views worth waking up for. A property that works just as hard as you do. The commercially finished walkout lower level offers an entirely different kind of opportunity. With multiple rooms, two separate entrances, and a layout designed with versatility in mind, there's potential to accommodate multiple businesses, create additional income streams, or simply bring your work a little closer to home. From professional offices and wellness services to creative studios and beyond, it's a space with serious potential. Of course, when you do feel like venturing out, the Caledon Ski Club, Belfountain, Credit River, Hiking trails, and exceptional golf courses are practically in your backyard. Natural gas, Bell Fibe internet, and parking for 10+ vehicles take care of the practical stuff.

Welcome to this beautifully maintained 4+1-bedroom home nestled on a picturesque 1-acre mature lot in the heart of Caledon. Offering the perfect blend of comfort, functionality, and privacy, this property is ideal for families, multi-generational living, or those seeking extra space.The bright and inviting interior features four spacious bedrooms and two well-appointed 3-piece bathrooms. The lower level offers exceptional flexibility with a separate entrance, an additional bedroom with an 11'8 x 7'11 walk-in closet, a full 4-piece bathroom, large Rec Room and other storage areas-perfect for extended family, guests, or potential in-law accommodations.Step outside to enjoy the tranquility of the expansive, tree-lined property, providing plenty of room for outdoor entertaining, gardening, or simply relaxing in a peaceful country setting. Ample parking accommodates multiple vehicles with ease, making it convenient for family and visitors alike.Located in a sought-after South Caledon setting, this exceptional property offers the charm of country living while remaining within easy reach of amenities, schools, parks, and commuter routes. A rare opportunity to own a spacious home on a beautiful one-acre lot with endless possibilities.For investors, this property offers future development potential being designated Employment within Caledon's Official Plan. Newly installed Municipal Water connection available at the lot line for a Buyer to connect at the Buyer's expense should they choose to convert to Municipal water. Buyer to verify all information for their own needs and purposes.

A truly exceptional and rarely offered estate, this remarkable property spans approximately 10 acres and features parking for over 10 vehicles. Nestled in the heart of Caledon, it offers an unparalleled blend of privacy, natural beauty, and convenience. Just steps from Albion Hills Conservation Area and the Trans Canada Trail, outdoor recreation is at your doorstep, while schools, shopping, dining, and major highways are all within easy reach. Whether you're seeking a private retreat, a family estate, or a unique investment opportunity, this extraordinary property presents endless possibilities. A rare offering that must be experienced to be fully appreciated.

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.

Welcome to this exquisite custom-built Raised Bungalow offering approximately 2,545 sq. ft. on the main level, plus an additional 2,465 sq. ft. of finished walkout lower level living space in the heart of rural Caledon. Surrounded by mature trees, backing the Caledon Trailway Path, scenic landscapes, this exceptional home offers the perfect blend of peaceful country living & modern family functionality. Mature gardens & an exposed concrete walkway create a warm welcome to the impressive front entrance. Step into the grand foyer featuring a soaring ceiling, skylight & double closets. The bright, open-concept main level showcases high-end finishes throughout, including elegant baseboards & trim. Designed for everyday living & effortless entertaining, the beautiful chef's kitchen features granite countertops, breakfast bar, coffee bar, abundant cabinetry & a spacious breakfast area, all open to the grand living room with fireplace & walkout to the inviting 4-season sunroom. The formal dining room with French doors, currently used as a home office, is a versatile space ideal for entertaining, working from home or adapting to your family's needs. The spacious primary suite features a walk-in closet & spa-inspired 6-pc ensuite with separate shower, while 2 additional generously sized bedrooms are complemented by a 5-pc main bath. Finished walkout lower level offers exceptional flexibility for extended or multi-generational living, featuring a massive recreation room with backyard walkout, a second family-sized kitchen with dining area, 4-pc bath with sauna, direct garage access, spacious laundry room, storage & utility room & abundant storage. Additional highlights include pot lights throughout, an expansive deck, above-ground pool, beautifully landscaped backyard & picturesque green space beyond. This one-of-a-kind property showcases exceptional craftsmanship, timeless design & the natural beauty that makes Caledon one of the GTA's most sought-after communities.

Welcome to this beautifully renovated bungalow in the heart of Caledon Village, offering the perfect blend of modern comfort and country charm. Situated on over half acre of meticulously landscaped property, this exceptional home features 3+1 spacious bedrooms and 3 bathrooms designed for both everyday living and tranquility. Step inside to discover a bright open-concept layout with stylish finishes and seamless flow throughout the main living areas. The renovated kitchen overlooks the dining and living spaces creating an inviting atmosphere for family gatherings and hosting guests. The fully finished basement provides additional living space with ample space for a gym, games room, and full entertainment. The space can easily be transformed into an excellent in-law suite offering flexibility for extended family, guests, or future income opportunities. Outside, enjoy your own private backyard retreat complete with mature landscaping, an in-ground pool, and plenty of green space to relax and unwind. Car enthusiats, hobbyists, and growing families will appreciate the impressive 3-car garage with ample outdoor parking. Located in the deisrable community of Caledon Village, this move-in ready home offers the tranquility of country living while remaining conveniently close to schools, parks, and major commuter routes. A rare opportunity to own a turn-key bungalow on a premium lot - don't miss it!

Discover the impressive Palgrave Elevation B by Rosehaven Homes: a beautifully designed, 3,042 sq. ft. detached residence where generous proportions and thoughtful details make every day feel extraordinary. The welcoming entrance leads to an elegant formal dining room, a private main-floor library ideal for working from home, and a spacious great room with fireplace. The bright kitchen features a centre island and an inviting breakfast area, perfectly arranged for entertaining and everyday family life. Upstairs, four well-proportioned bedrooms offer comfort and privacy, including a luxurious primary retreat with walk-in closets and ensuite, plus convenient second-floor laundry as illustrated on the builder's plan. Enjoy 10-foot ceilings on the main floor, 9-foot ceilings upstairs, impressive 8-foot main-floor doorways, a double garage, and approximately $40,500 in finished upgrades in addition to other selected structural upgrades. Set on a 41-foot detached lot in Caledon's Mayfield Collection, this finished inventory home presents a remarkable opportunity for buyers seeking space, sophistication and new-home appeal. Offered as finished inventory with no further customization.

Welcome to your own private Caledon retreat, where nature, tranquility, and exceptional craftsmanship come together. A long, winding driveway leads you through a breathtaking canopy of towering whispering pines and mature hardwood forest, creating a truly unforgettable approach to this custom-built bungalow. Thoughtfully designed for comfortable living, the spacious bungalow features a fully finished walkout basement, abundant storage, and versatile living spaces ideal for family, entertaining, or multi-generational living. A Private Sanctuary in the Hills of Caledon. Welcome to an extraordinary 26-acre estate where nature, privacy, and timeless craftsmanship create a lifestyle that's second to none. Arrive home via a long, winding driveway through a majestic forest of towering whispering pines and mature hardwoods, setting the stage for this exceptional custom-built bungalow nestled in one of Caledon's most picturesque settings. Designed to embrace its spectacular surroundings, this energy-efficient home offers spacious, thoughtfully designed living with a fully finished walkout basement and an abundance of storage. Large windows invite the outdoors in, filling the home with natural light and showcasing peaceful views in every season .Step outside to an expansive multi-level deck, perfect for entertaining, family gatherings, or simply relaxing while immersed in the sights and sounds of nature. Explore your own private walking trails winding throughout the property, offering a true Muskoka-inspired retreat just minutes from the city. Despite its peaceful seclusion, you're only moments from Caledon's renowned restaurants, charming cafés, boutique shopping, golfing. Whether you're looking for a forever home, a peaceful escape, or a place where family and friends naturally gather, this remarkable property delivers. More than just a home, it's a destination you'll be proud to call your own, don't let this one pass you by.

Discover the exceptional Stationlands Elevation B by Rosehaven Homes, a stunning 2,749 sq. ft. detached residence in Caledon's sought-after Mayfield Collection. Thoughtfully designed for family living and entertaining, the main level offers a welcoming foyer, generous living and dining rooms, a spacious family room and an inviting kitchen with centre island and breakfast area. Upstairs, four well-proportioned bedrooms include a beautiful primary retreat with walk-in closet and private ensuite, while a convenient second-floor laundry makes daily life easier. The additional bedrooms enjoy an ensuite and a semi-ensuite arrangement shown on the builder plan. Highlights include a double garage, 9-foot second-floor ceilings, upgraded 8-foot main-floor doorways, a separate side door and an upgraded shower in Ensuite 2. Situated on a regular 11.60 m x 27.50 m lot, this is an outstanding opportunity to secure a brand-new Rosehaven home with a limited-time builder incentive. Trim-stage inventory: exterior/interior colours may still be selectable subject to builder approval; no electrical, HVAC or plumbing changes. All specifications and dimensions to be verified with builder.

Set on a picturesque and private 1.02-acre lot with no rear neighbours, this spacious property offers the perfect blend of tranquility, functionality, and convenience. Surrounded by open countryside and clear views, it provides an ideal setting for families, retirees, or anyone seeking a peaceful lifestyle. The well-designed home features spacious rooms thruout & 3 generously sized bedrooms, 2.5 bathrooms, a separate living room, formal dining room, and an inviting family room with a cozy fireplace. The thoughtful layout offers comfortable everyday living and excellent space for entertaining. Step outside to a large deck overlooking the private backyard, perfect for relaxing, hosting gatherings, or enjoying the serene surroundings. Accessibility has been carefully considered, with wheelchair-accessible interior doorways throughout the home. The unfinished basement offers outstanding potential, featuring impressive 9-foot ceilings and a cold cellar, creating endless possibilities for additional living space, a recreation area, workshop, or in-law suite. A furnace updated within the last five years provides added peace of mind and efficiency.Located in a desirable rural setting while remaining close to everyday amenities, this property also offers convenient access to world-class golf, including TPC Toronto at Osprey Valley, home of the RBC Canadian Open, as well as Paintbrush Golf Club and Devil's Pulpit Golf Association. A rare opportunity to enjoy spacious country living with exceptional privacy and future potential.

Nestled on a stunning 3-acre property backing onto peaceful forest, this 2-storey, 4-bedroom home offers privacy, space, and comfort, all just minutes from schools, shopping, and highway access. Its a rare opportunity to enjoy the serenity of country living with modern convenience at your doorstep. At the heart of the home is a custom kitchen designed for gatherings and family life. With seating for up to 30 people, banquet-style benches with hidden storage, and a massive quartz island with undermount sink, its the perfect space for entertaining or enjoying casual meals together. A built-in double wall oven, microwave, gas cooktop, lazy Susan corner cabinet, deep drawers, and abundant storage keep everything organized and within reach. Built-in speakers provide soft, inviting ambiance, while pot lights and oversized windows fill the room with tons of light. Walk out to the massive interlock patio with hot tub for seamless indoor-outdoor living. The MF also features a bright LR with a gas fireplace, custom built-ins, and a walkout to the deck, plus a study/family room with custom cabinetry and shelving, ideal for work, reading, or cozy family moments. Upstairs, the primary suite is a true sanctuary, offering a spa-like 4pc ensuite, a fully customized built-in closet system, pot lighting, and built-in speakers. Three additional bedrooms provide space and comfort for family and guests. The walkout basement is an entertainers dream, featuring a full wet bar, bar seating, bar fridge, built-in cabinetry, speakers, a 3pc bathroom, and a cozy sitting area. Step outside and enjoy the sprawling backyard perfect for summer evenings, kids at play, or quiet moments surrounded by nature. With built-in speakers throughout the home, Thousands spent in thoughtful upgrades at every turn, and an estate-like setting that blends elegance, privacy, and comfort, this property is more than a house its a lifestyle designed for lasting memories, family gatherings, and entertaining friends.

Experience Luxury Estate Living in the prestigious Osprey Mills community, nestled in the picturesque countryside of Alton! Offering an exceptional blend of sophisticated design, spacious interiors and peaceful country surroundings, this stunning executive home is situated on an impressive 160' x 225' estate lot, providing remarkable privacy and room to enjoy the outdoors. Boasting approximately 3,500 sq. ft. of beautifully appointed above-grade living space, this residence features 4 generous bedrooms and 4 bathrooms, including 3 ensuites, making it ideal for growing families and those who love to entertain. Soaring 10' ceilings on the main level and 9' ceilings upstairs create an airy, grand atmosphere, complemented by elegant engineered hardwood flooring, quartz countertops and oversized 24" x 24" tile. At the heart of the home, a stunning white kitchen with centre island flows seamlessly into the inviting family room, creating the perfect setting for everyday living and memorable gatherings. The expansive grounds offer endless possibilities for outdoor entertaining, gardens, recreation or simply enjoying the tranquility of estate living. Beyond your doorstep, discover the charm of Alton, renowned for its scenic countryside, historic village atmosphere, Alton Mill Arts Centre, nearby Millcroft Inn & Spa, golf courses and beautiful trails. Enjoy the serenity of country living with convenient access to Orangeville, Caledon and the GTA. A rare opportunity to embrace an elevated lifestyle in one of the area's distinctive estate communities. With additional homes available in Osprey Mills, there's even an opportunity to bring family or friends close by. Discover the space, elegance and lifestyle you've been dreaming of. Welcome home!

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.

Stripped back, rebuilt & completely transformed into a custom modern farmhouse bungalow on approx 1 acre in Caledon Village. Offering 4+1 bedrooms, 3 full bathrooms, over 4,100 sq. ft. of beautifully finished living space, including a finish bungalow bsmt w/ king-size 1-bedroom in-law bsmt apartment, this is anything but an ordinary bungalow. The striking exterior w/ Hardi cement-fibre board siding, bold black aluminum detailing, windows, oversized front door & white-oak-style garage doors. Inside, a dramatic foyer introduces custom wall mouldings, large-format tile, solid-core shaker doors. 7' interior drs, 7" poplar baseboards, detailing add architectural presence t-out. Spectacular sun-filled XL kitchen, dining, living space designed for both everyday family life and large-scale entertaining. 6 skylights, white oak hardwood flrs oversized 4-panel sliding glass dr flood the space w/ light. Dream custom kitchen, anchored by an extraordinary 8' x 15' quartz waterfall island accommodates serious cooking, effortless entertaining, features 2 sinks, 2 dishwashers, 2 pantries, wall-to-wall custom cabinetry, tiled backsplash, reverse-osmosis drinking water,LG appliances. Custom laundry/mudroom. 4 bdrm layout-The guest bathroom carries the custom aesthetic hexagon flr, oak vanity, Carrera-tiled shower, black fixtures. Mstr bdrm is private escape, custom wall mouldings, spa-inspired ensuite glass shower, black tile flooring, Theodore white oak vanity. White oak staircase 2,000+ sqft Bsmt, King-size 1-bedroom in-law aprtmnt lrg rec area, kids play space, glass-enclosed home gym. 3-piece bath, 2nd custom kitchen w/ island o/l the living area. XL 40' x 20' deck features substantial Douglas fir gazebo beams, cedar plank decking, glass railings. ***Lot Irregularities: 122.87 ft x 36.22 ft x 195.51 ft x 160.13 ft x 247.21 ft

Welcome to 7 Rolling Meadow - an exceptional private custom estate nestled on 3.6 acres, featuring an expansive 316 ft frontage approximately 4,600 sq ft of living space, set within one of East Caledon's most desirable communities on a quiet dead-end street. Surrounded by mature trees & scenic natural beauty, this impressive property offers the perfect blend of luxury living, privacy, and everyday comfort. Set well back from the road, a large circular driveway and 3-car garage provide direct access to the mudroom & laundry. This beautifully maintained residence offers oversized principal rooms, timeless finishes, custom carpentry, a seamless indoor-outdoor living designed for both entertaining and family life.The heart of the home features a stunning designer kitchen complete with granite countertops, custom cabinetry, a centre island, breakfast bar, & high-end stainless steel appliances. The sun-filled breakfast area walks out to a sprawling deck overlooking the breathtaking property and its endless natural scenery - creating the perfect setting for morning coffee or evening gatherings. The bright open-concept great room boasts soaring ceilings, rich hickory hardwood flooring, elegant pot lights, electric fireplace, & large windows that bring the outdoors in. The spacious primary retreat offers a private escape: a walk-in closet, a 5-piece spa-like ensuite, and direct walkout access to the deck.This property is loaded with thoughtful upgrades including abundant storage, California shutters throughout, & Santos Mahogany hardwood flooring in the bedrooms. The finished lower level is ideal for multi-generational living or entertaining, featuring additional bedrooms, a private office, an exercise room, and a spacious recreation area boasting an electric fireplace custom finishes throughout. Substantial outbuildings - a 24 x 20 steel-built structure an 18 x 11 cedar-built - both serviced by electrical, complete this remarkable offering.

Discover the perfect blend of charm, space, and modern living at this beautiful country property in the heart of Caledon. Situated on 4 Acres this home offers a cottage-like feel just minutes from city conveniences.Step inside to a warm and inviting layout featuring a sun-filled kitchen with breakfast area, a spacious family room, and a serene sunroom overlooking the property. The upper level offers three bedrooms, two with private walk-out decks, plus a den and spa-inspired washrooms including his & hers walk-in closets.The finished lower level includes three additional bedrooms and a full washroom, ideal for extended family or guests. A brand-new 900 sq. ft. addition with a roughed-in basement apartment gives you the opportunity to create your own personal touch.Outdoors, enjoy a barn, garden shed, and endless room for hobbies, recreation, and entertaining. With three natural gas fireplaces and a cozy wood-burning option, this property truly balances comfort and country. Detached 4.10 x 3.14m, oversized garage (790 sf). Automatic Back Up Generator for whole home. If you're looking for a family retreat or a unique investment opportunity, 20054 Horseshoe Hill Road offers the lifestyle you've been waiting for.

Welcome to 18 Filton Road, a custom-built executive home in the heart of Caledon East. This 4-bedroom residence showcases 7.5-inch engineered white oak hardwood floors, upgraded trim, and designer colours throughout. A dramatic 17'10" open-to-above ceiling soars over the foyer and living room, anchored by a wood-burning fireplace with a granite facade. The custom kitchen features Fox Woodwork cabinetry with pantry rollouts, a farmhouse apron sink, custom panel refrigerator, quartz counters, backsplash, and a Frigidaire 5-burner gas range, opening to a breakfast area with a walkout to an interlocking stone patio retreat. The main-floor office boasts a bay window, crown moulding, and custom built-ins, while the laundry room offers designer cabinetry and storage. The main-floor primary retreat impresses with its own wood-burning fireplace, a bay window with walkout to the back patio, a walk-through closet by Organized Interiors, and a spa-inspired 5-piece ensuite with a jacuzzi tub and separate glass shower. Two more bedrooms and a beautifully finished 4-piece bath complete the upper level. The finished basement adds a fourth bedroom, a spacious rec room with wired 5.1 surround sound, a home gym with a rough-in for a future kitchen, a 3-piece bath, and a Sauna Ray infrared sauna. Outside, enjoy your private backyard oasis: a heated saltwater pool (14'x28') with automatic cover and granite coping, a cedar post-and-beam covered patio with motorized Somfy screens and infrared heaters, and a custom cabana with change room and wireless pool controls. The landscaped grounds back onto protected conservation land, with full property irrigation, armour stone accents, and mature gardens. The oversized double garage offers epoxy flooring, slat-wall storage, a mezzanine, and raised ceilings. Additional highlights include a new 2022 York furnace with HRV, a 7-camera security system, Nest thermostat, and central vacuum. A rare opportunity to own a true turn-key luxury retreat.