14294 Winston Churchill Boulevard

FOR SALE
$2,389,000
14294 Winston Churchill Boulevard, Caledon
14294 Winston Churchill Boulevard
14294 Winston Churchill Boulevard
14294 Winston Churchill Boulevard
14294 Winston Churchill Boulevard
14294 Winston Churchill Boulevard
14294 Winston Churchill Boulevard
14294 Winston Churchill Boulevard
14294 Winston Churchill Boulevard
14294 Winston Churchill Boulevard
14294 Winston Churchill Boulevard
14294 Winston Churchill Boulevard
Browsing Limit Reached
Please Register for Unlimited Access
4
BEDROOMS
3
BATHROOMS
1
KITCHENS
10 + 2
ROOMS
W12591338
MLSID
Contact Us
Property Description
In the storybook hamlet of Terra Cotta, Caledon, just steps from the Cataract Trailway and Terra Cotta Conservation Area, this exceptional property offers elegance and a deep connection to nature. Nearly 2.5 acres back onto protected conservation land with no rear neighbours - only forest, fresh air, and birdsong. The lot blends cleared lawn and woodland, with sunny spaces for entertaining and shaded spots for quiet reflection. Your fenced backyard oasis is anchored by a heated saltwater pool with a waterfall, an expansive patio for barbecues and lounging, and the ultimate privacy of your own forest. Inside, vaulted ceilings and large windows flood the main living areas with natural light. The formal dining room sits off the foyer behind French doors, while the grand two-storey living room features a two-way wood-burning fireplace shared with the breakfast room. The chefs kitchen boasts top-of-the-line Miele appliances, including an oversized fridge, built-in oven, sleek cooktop, and flush-mount range hood. A spacious sunken family room off the breakfast and kitchen opens to the backyard. The main floor also offers a laundry room with a walkout and a spa-inspired 3-pc bath with heated floors and a glass shower, perfect after a swim. Upstairs, the open loft hallway provides space for an office, hangout space, or reading nook. Four bedrooms include a sprawling primary suite with his-and-hers walk-in closets. The finished basement offers a huge rec/games room plus a bonus room - ideal as a gym, extra bedroom, or office. An insulated double-car garage with epoxy flooring completes this property. From sunrise coffee on the patio to starlit swims beneath the trees, this Terra Cotta retreat is more than a home - its a lifestyle.
Property Features
Fenced Yard, Greenbelt/Conservation, Lake/Pond, Wooded/Treed, Auto Garage Door Remote, Central Vacuum, Propane Tank, Storage, Sump Pump, Water Heater Owned, Water Softener, Water Treatment, Private Double, Security System, Monitored, Propane, Wood
Property Details
Address
14294 Winston Churchill Boulevard
Community
Postal Code
L7C 3E8
Property Type
Detached, Detached
Zoning
A1*
Lot Size
232' x 416'
Acreage
2.4 Feet
Taxes
$6,607 (2024
Basement
Finished, Full
Exterior
Backs On Green Belt, Landscaped, Patio, Privacy
Heat Type
Forced Air
Heat Source
Propane
Water
Well
Pool
Inground, Salt
Parking Spaces
6
Garage Type
Attached
Listing contracted with Coldwell Banker Elevate Realty
Similar Listings
19555 Shaws Creek Road, Caledon
4
BEDS
3
BATHS
$2,099,900
FOR SALE
A Rare Landmark Estate In The Heart Of Caledon. Set on 8 breathtaking private acres surrounded by rolling hills, forest, trails, and creekside scenery, this extraordinary residence offers a lifestyle rarely found within reach of Toronto.Thoughtfully created from a purpose-built 1856 oak barn sourced from King Township, this architectural masterpiece blends authentic heritage craftsmanship with refined modern living. Approximately 3,500 sq ft featuring 4 bedrooms and 3 bathrooms, the home showcases restored handcrafted beams and posts, soaring cedar-clad ceilings, rich timber framing, and a stunning two-sided stone wood-burning fireplace.A remarkable architectural feature from Toronto's iconic Granite Club adds to the home's one-of-a-kind character and timeless design.Designed for exceptional family living and entertaining, the property offers winding private trails, open natural spaces, wraparound porch views, and a handcrafted rustic treehouse - creating an unforgettable retreat-style setting for all seasons.A true four-season lifestyle property ideally located: 9 mins to Caledon Ski Club 10 mins to TPC Toronto at Osprey Valley, host of the RBC Canadian Open Minutes to hiking, cycling, rivers, golf, skiing, and equestrian amenities Near top-rated schools in Belfountain and Alton 2 mins to GoodLot Farmstead BreweryAdditional features include geothermal heating system, artesian well, circular driveway, A/C, and a fully insulated 1,200 sq ft detached garage/workshop with loft space.An extraordinary opportunity to own a private country estate offering luxury, nature, history, and lifestyle in one remarkable property.Includes: Stainless steel fridge, dishwasher, cooktop, built-in oven, washer & dryer, all ELFs and window coverings.
5 Cedar Drive, Caledon
3+1
BEDS
3
BATHS
$1,950,000
FOR SALE
Welcome to Cedar Drive!!!! One of Caledon's most prestigious Estate Style developments. This 3.03 acre stunning property offers you close proximity to Toronto and only 30 minutes to Pearson. Surrounded by many walking/cycling trail systems & some of Canada's best golf courses including many unique dining experiences such as Rays Bakery, Caledon Hills and Good Lot Craft Breweries. Set well back from the road, you will enjoy the complete privacy you desire from towering 30 ft trees while affording lots of sunlight. Perfect for creating your own oasis. Cozy up to the wood burning fireplace in the living/dining rooms and enjoy the views from the large picture windows. This amazing home with 3+1 BR's and 3 Baths, will not disappoint from the hard wood flooring, to the walk out lower level to the quartz counter tops, stainless steel appliances, wrap around porch and a large front perennial garden. Just minutes on Hwy 10 to Brampton or Orangeville. Just a chip & a put to the Devils Pulpit and Osprey Valley Golf, a cast away from the Caledon Trout Club, a hop skip and a jump to the Caledon Trail Way & Bruce Trail and a snow shoe to the Caledon Ski Club. You will feel you are in Europe every time you drive along the Forks of the Credit Rd. This is a must see. Bathrooms have been freshly updated.
19728 Kennedy Road, Caledon
3+1
BEDS
4
BATHS
$2,289,000
FOR SALE
This elegant bungalow has everything today's buyer could wish for-beautifully finished and move-in ready. Behind striking double iron gates, the full stone exterior and exquisite landscaping create an impressive first impression. Inside, coffered ceilings, rich crown moldings, and custom details flow throughout a layout designed for both family living and refined entertaining.The inviting family room with fireplace opens to a dream kitchen featuring a large central island, premium cabinetry, and built-in appliances-perfect for hosting or everyday comfort. A formal dining room offers the ideal space for celebrations and elegant dinners.The spacious primary bedroom is a private retreat with a grand 7-piece ensuite showcasing double vanities, a soaker tub, and glass shower, plus separate his-and-hers walk-in closets. Main-floor laundry adds everyday convenience.The completely finished basement provides exceptional living space, ready to entertain large gatherings with an impressive wet bar and open recreation area. Enjoy movie nights in the home theatre or stay active in the dedicated gym space-all within your own home.Set on a beautifully landscaped property, this home blends classic design with modern luxury at every turn. With no detail overlooked and nothing left to add, this residence defines effortless elegance and offers a truly turn-key lifestyle.
27 Cedar Drive, Caledon
5
BEDS
3
BATHS
$2,250,000
FOR SALE
Magnificent Georgian Estate in Prestigious Caledon! Welcome to an extraordinary 5-bedroom, 3-bathroom Georgian fieldstone estate on 2.6 private acres, where timeless elegance meets modern sophistication. Every detail has been meticulously curated, from the heated floors to the vaulted ceilings and custom Pella windows, creating an atmosphere of unparalleled luxury. The gourmet kitchen is a chefs dream, featuring Sub-Zero, Miele, and Monogram appliances, a grand walnut island with granite countertops, and a butlers pantry with a wine fridge and reverse osmosis filtration. The breakfast area is warm and inviting, anchored by a charming stone fireplace with a wood-burning insert, perfect for cozy mornings. The library is a masterpiece, with a soaring wood-beamed ceiling, floor-to-ceiling windows, and remote-controlled Hunter Douglas blinds, offering a breathtaking space to work or unwind. The living and dining rooms exude sophistication with crown molding and rich pine plank floors, creating the perfect backdrop for elegant entertaining. The primary suite is pure indulgence, boasting walnut hardwood floors, a custom walk-in closet, and a lavish 6-piece ensuite with heated marble floors, a claw-foot tub, and exquisite walnut cabinetry. A private in-law suite offers additional space with a sitting area, heated floors, and a spa-inspired 3-piece bath. Step outside into a world of tranquility. Entertain on the expansive composite deck, sip champagne in the moss-covered gazebo, or soak in the Hydropool hot tub (2021) under the stars. Flagstone pathways wind through manicured perennial gardens, while the outdoor propane fireplace and gas BBQ create the perfect setting for alfresco dining. Modern upgrades include a new roof (2022), natural gas generator (2021), and garage door (2021). Surrounded by world-class golf courses, ski clubs, and conservation areas, this estate offers a lifestyle of unparalleled refinement. This is truly a rare opportunity to own a legacy home.
22 Southridge Trail, Caledon
3
BEDS
3
BATHS
$2,199,999
FOR SALE
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.
20051 Willoughby Road, Caledon
3
BEDS
3
BATHS
$2,199,900
FOR SALE
Beautiful custom-built Bungalow-Raised on a stunning 6+ acre treed rolling lot in sought-after Caledon. Featuring a small stream along the southwest portion of the property, this home offers privacy, natural beauty, and refined country living just minutes from amenities and 400-series highways .Inside showcases hardwood floors, crown moulding, cathedral and vaulted ceilings, elegant trim work, and a bright open layout. Enjoy an oversized heated 3-car garage with direct interior access, a chef-inspired kitchen with brand-new high-end appliances, spacious living room with gas fireplace, separate dining area, and walkout to a deck overlooking the property. The main level offers 3 generous bedrooms, including a primary suite with Ensuite bath, walk-in closet, and brand-new custom closet & organizers. The bright walkout lower level features high ceilings, large windows, drywall, rough-in bath, ample storage, and double-door access to the backyard, ready for your finishing touches. Perfect for luxury buyers, outdoor enthusiasts, and nature lovers seeking privacy, space, and refined country living in one of Caledon's most desirable locations.Highlights:6+ acre treed rolling lot with stream Custom-built Bungalow-Raised Heated oversized 3-car garage400 AMP electrical service with 200 AMP panels for house and garage. Brand-new high-end kitchen appliances. Bright walkout lower level with rough-in bath Close to parks, trails, Caledon Lake, fairgrounds, golf courses, amenities, and highways.
4 Wolf Crescent, Caledon
4
BEDS
3
BATHS
$2,139,900
FOR SALE
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.
7 Rolling Meadow Drive, Caledon
3+2
BEDS
3
BATHS
$1,975,000
FOR SALE
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. Click the 3D Virtual Tour!
143 Green Lake Road, Caledon
3+1
BEDS
4
BATHS
$1,849,000
FOR SALE
Experience over 300 feet of pristine waterfront just 45 minutes from Downtown Toronto-where refined living meets the tranquility of a year-round executive retreat. Ideally located minutes from TPC Toronto at Osprey Valley, home of the Canadian Open, as well as The Pulpit Golf Club & Caledon Ski Club, this exceptional property offers an unmatched four-season lifestyle. Set within the private & exclusive Green Lake community, centered around a 60-foot-deep spring-fed lake stocked with trout & bass, this is a setting designed for those who value serenity, recreation & connection. Enjoy quiet morning paddles, sun-soaked afternoons by the water & unforgettable evenings with moonlit swims & lakeside dining. Positioned on a breathtaking 2.36-acre lot, the modern post-&-beam log home blends timeless character with thoughtful design. A detached heated & insulated garage/shop, charming guest log bunkie with full foundation & 3-piece bath, plus the added security of a backup generator, provide comfort, flexibility & peace of mind. Winding flagstone walkways lead through beautifully curated gardens to an incredible outdoor living experience complete with an outdoor kitchen, sand beach area, private dock & gazebo-all framed by stunning lake views. This package has all the elements to be a lasting family legacy for generations! If you've ever found yourself saying, "I wish I had known about this before," this is your opportunity to own something truly special-where memories are made, traditions are built, and a once-in-a-lifetime offering becomes your reality.
24 Cedar Drive, Caledon
3+2
BEDS
3
BATHS
$1,799,000
FOR SALE
MUST SEE!!!! Escape the hustle, a hidden sanctuary awaits. Private retreat in one of the BEST areas of Caledon. Beautiful 2.98 acres located just off the scenic Forks of The Credit. Custom 3 bedroom raised bungalow with 3 car garage. Over 2100 sqr ft on the main floor and over 4000 sqr ft of finished living space!! Kitchen has granite counters, stainless steel appliances and walk-out to a multilevel deck. Amazing 14 ft vaulted ceilings, walnut hardwood floors and stone wall feature in the open concept living and dining rooms. Perfect for entertaining!! Primary Bedroom has a 5 pc ensuite, 2 walk-in closets and heated floors. It also has a private balcony overlooking the pond. 2 more spacious bedrooms and a 4 pc bath on the main floor. The lower level features High ceilings, 2nd kitchen, 3 pc bathroom, above grade windows and multiple entrances making it perfect for multi-generational living. Could easily turn the basement into a rental unit for additional income!! 4th and 5th bedrooms both have fireplaces and sliding doors to the patio. This home also has a steel roof with heat trace overhang, a new septic (2025) $50,000 approx and generac system. Available Bell Fibe for home office. Gorgeous outside space to entertain or just take in the surroundings. Move in and enjoy the privacy, peace and tranquility of this amazing property! Sitting on one of the most beautiful 3 acres of an exclusive sought after area of Caledon. Great value!!! Priced $150k plus below any other home on the street!!!!!
6785 Highway 9 Road, Caledon
3+3
BEDS
3
BATHS
$2,250,000
FOR SALE
Nestled on a private and beautifully 10.01 acre parcel in Caledon, this exceptional ranch-style stucco and brick bungalow offers the perfect blend of peaceful country living and functional versatility. Boasting nearly 400 feet of frontage along Highway 9, the property provides outstanding exposure while maintaining a serene, resort-like setting winding driveway highlighted by a stunning, professionally landscaped backyard oasis.The home has been thoughtfully updated throughout, featuring refreshed main floor flooring that enhances the warmth and flow of the living spaces. Large windows are strategically placed across the home, allowing natural light to pour in and creating bright, inviting interiors while showcasing picturesque views of the surrounding property. The main level offers 3 spacious bedrooms and a beautifully updated, high-end open-concept gourmet kitchen, complete with premium appliances, modern finishes, and ample workspace-perfectly designed for both everyday living and entertaining. Adjacent to the main living area is a charming 3-season sunroom, offering a tranquil space to relax while enjoying eye-catching views of the landscaped grounds and mature trees throughout the seasons.The fully finished, sun-filled walkout basement provides exceptional additional living space, featuring 3 further bedrooms and a large, versatile layout ideal for extended family, guests, or multi-generational living arrangements. Adding tremendous value and functionality to the property are 2 impressive workshops-one measuring approximately 35 x 48 and the other 35 x 50-offering extensive space for hobbyists, contractors, tradespeople, or those seeking a home-based business opportunity. These outbuildings significantly enhance the property's usability and appeal.This is a rare opportunity to own a beautifully maintained and updated bungalow on a picturesque 10-acre property with substantial frontage, privacy, and unmatched versatility in a highly desirable Caledon location.
6 Golfway Court, Caledon
4+1
BEDS
4
BATHS
$2,199,888
FOR SALE
Nestled on a Quiet Cul-De-Sac, 6 Golfway Crt is Located In Prestigious Caledon Woods Estates and Situated On One Of TheBest Lots Backing Onto Caledon Woods Golf Course, This Custom-Built, 4+1 Bedroom, 3,773 sqft + Finished W/O BasementTwo Storey Residence Is Perfect For Entertaining. The Dramatic Interior Features High Majestic Ceilings, a Fabulous Staircase,and Gleaming Hardwood And Ceramic Flooring Throughout. The Extraordinary High-End Gourmet Kitchen Boasts MapleCabinetry, An Island With Granite Counters, And A Thermador Gas Range. The Breakfast Area Opens To A Two-Tiered DeckEquipped with a Gas Fire Pit, Overlooking the 18th Hole. The Finished Walk-Out Lower Level Features a 2nd Kitchen, aBedroom w/ 4pc Ensuite and is Accessible By Two Staircases. A Large Family Room, Main Floor Home Office, Two GasFireplaces, Primary Bedroom w/ Private Balcony, (2) Walk-In Closets & 6pc Ensuite Complete The Interior. The PropertyFeatures a Three-Car Garage w/ Gas Heater, a New Driveway w/ Space For 8+ Cars, And A Beautifully Landscaped Front AndBack w/ Irrigation System. Two Sheds Provide Additional Storage. Recent Upgrades Include New Furnace ('25), Garage Doors('25), New Driveway ('24), Driveway Sealing ('25), W/H Humidifier ('23), & CAC (2022). Large Property Surrounded by MatureTrees,The Home Ensures Both Privacy And Stunning Scenery. This Spectacular Home Truly Offers Quality Craftsmanship AndBreathtaking Views. Located Just Minutes from Various Amenities, Scenic trails, Multiple Golf Courses, Schools & Parks, This isa Rare Opportunity to Own an Exceptional Home in One of Caledon's Most Private & Desirable Areas.
82 Marilyn Street, Caledon
4
BEDS
4
BATHS
$2,199,000
FOR SALE
Welcome to 82 Marilyn St. Situated on a highly sought after lot backing on to Caledon East Green space with a meandering creek. This 2 storey, four bedroom home with in-law suite has been meticulously updated. Upon entering the home, you will see the owner has added an entirely new stair case with accent lighting. 6" White Oak Hardwood has been Used. 6" Engineered white oak hardwood planks throughout the main and Second Floor. The main floor has been updated to an open concept kitchen and Family Room Design with Island seating. This new Chef's kitchen provides a Miele centric cooking experience. The 36" Gas cooktop and hood along with a Miele double wall oven. The Bosche SS Refrigerator, integrated Dishwasher, built in Microwave and KitchenAid Wine Cooler round out this beautiful kitchen. The family room has a beautiful Open Gas Oak Log Set complete with walnut Mantle. The main floor has a convenient Oversized Laundry area just off the garage. On the second floor, the Primary bedroom and 5 pc ensuite which also contains a very large highly functional Walk-in Closet. In the basement, 5" Engineered White Oak Hardwood forms the base for the new owners special In-Law Suite with added 3pc bathroom. There is also a large recreation room with Fireplace. The New Windows, Doors, Riobel Faucets, Roof and HVAC will provide the new owners with years of comfort.
98 William Crisp Drive, Caledon
4
BEDS
4
BATHS
$2,099,900
FOR SALE
Luxury Executive Detached Estate Home In Prestigious Osprey Mills, 3252 Sqft Of Above Ground on 98' x 215' Estate Lot. Featuring 10 Ft Main Floor Ceilings,9' Basement & 2nd Floor. Engineered Hardwood Flooring Throughout, Extended Height Kitchen Uppers + Stacked Uppers, Quartz Countertops Throughout, Stainless Steel Kitchen Appliances. See Schedule For Standard Features And Finishes. Taxes Not Assessed. OPEN HOUSE EVERY SATURDAY AND SUNDAY 12-5! Rent To Own Program available.
20054 Horseshoe Hill Road, Caledon
3+2
BEDS
4
BATHS
$1,999,900
FOR SALE
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.
16735 Mississauga Road, Caledon
3
BEDS
2
BATHS
$1,999,000
FOR SALE
Welcome to the historic hamlet of Belfountain. A unique Hamlet just north of the Village of Terra Cotta and offers residents and visitors the memorable experience of experiencing quaint shops & food services just a 15 minute walk from this 10 acre gem. The house is move in ready & overlooks a stunning pond, inground cement pool with a walkout basement. The rolling nature of the land will not disappoint and is perfect for your hobby farm offering paddocks, barn and trails. The home has been extremely well maintained and the perennial gardens have been cared for by the original owner. The home sits well back from the road on elevated land offering an amazing westerly view of the Caledon Hills. A hop skip & a jump to the Bruce Trail, Caledon Trail and the Cataract/Elora Trail systems, A snow shoe from the Caledon Ski Club, just a cast away from the Caledon Trout Club and a chip & a put from the award winning golf such as Osprey Valley, Devils Pulpit and Caledon Golf & Country Club. This Charming Bungalow Features A 2 Car Attached Garage, 3 Bedrooms with the primary bedroom featuring a walk out to the large balcony overlooking the pond & pool. The basement boasts a walkout to the back paddocks & hobby farm. The property offers a barn with water, power and room for the storage of hay. There are 4 independent paddocks for the horses or other hobby farm pets. It's all available for the taking and can be yours.
9 Maple Grove Road, Caledon
4
BEDS
4
BATHS
$1,999,000
FOR SALE
This gorgeous bungalow is looking for a family to call it home! Custom built open concept with 4 bed, 3.5 bath and 3145 sq ft of exquisitely finished space. Nearly 6300 sq ft in total! A stunning cathedral ceiling spans the kitchen and centres upon the cozy stone-clad gas fireplace adorned with a farmhouse chandelier in the living room. The interior finishes are elevated with recessed lighting and wide plank hardwood floors throughout. The show-stopping white and hardwood kitchen with gleaming quartz counters & continuous backsplash is sure to impress, with a built-in lower seating area, cabinetry on both sides of the island, walk-in pantry, pot filler for added convenience and statement glass cabinets. The laundry room has it all - cuteness and practicality with an oversized stainless steel sink, tons of cabinetry and natural light, open shelving, clothes hanging bar, quartz countertops, and even a stop-n-drop for coats and shoes. The Primary suite is a dream, offering privacy through separation from the other bedrooms, a walk-in closet outfit with built-in cabinetry and countertop, and a 5pc ensuite with heated floors, free-standing tub, private water closet, double vanity and glass shower. So much more to see! Generous 100 x 150 ft lot on quiet street in sought after Caledon Village. Tarion New Home Warranty. Awesome commuter location - 15 mins to Brampton or Orangeville! To be completed May 2026: Final grading, grass seeding, rear deck railing (black alum. pickets) and steps, interlock path to front door and steps, driveway to be widened to 3 car.
6 Overlook Ridge, Caledon
3+2
BEDS
3
BATHS
$1,950,000
FOR SALE
Elevate Your Lifestyle with this Stunning Custom Built Bungalow with Finished Walk-Out Basement in Rolling Meadows Estates, Situated on a Picturesque Estate Lot. Magnificent Backyard Oasis, Heated Pool, Cabana, and Hot Tub, Landscaped with Flag Stone, Interlock and Stone Steps. Custom Gourmet Kitchen with Granite Counters, Stainless Steel Appliances, Walkout to Sunroom W/Gas Fireplace connected to Large Deck Overlooking Pool, Perfect For Outdoor Gatherings. 9 Foot Ceilings, Hardwood Floors, Cornice Mouldings, Beautifully Finished Top-to-Bottom. Walkout Lower Level with Large Rec/TV Room & Additional 2 Bedrooms, Full Bathroom and 2nd Kitchen. 3 Car Garage with huge driveway. Superb Finishes and Great Layout.
20088 Main Street, Caledon
3
BEDS
2
BATHS
$1,899,000
FOR SALE
Nestled in the charming Village of Alton, this stunning modern bungaloft farmhouse offers the perfect blend of country tranquility and contemporary living on a picturesque 4.6-acre property. Thoughtfully designed with an open concept layout, the main level features a spectacular great room that seamlessly flows into the beautifully renovated kitchen complete with an oversized island, high-end appliances & exceptional space for entertaining. A spacious dining room adds warmth and elegance, while the main floor also offers two bedrooms, a stylish 5-piece bath & a private office ideal for working from home. The upper loft level provides a cozy family room retreat along with a third bedroom and 3-piece bath, creating the perfect separate space for guests or family. The unspoiled basement offers endless potential to customize to your lifestyle needs. Outside, the oversized barn with 100 amp service is a dream for hobbyists, car enthusiasts or anyone seeking the perfect workshop or storage space. Surrounded by the beauty of Caledon countryside, this exceptional property backs onto the renowned Millcroft Inn & Spa and is just minutes to TPC Toronto at Osprey Valley, while remaining close to the shops, restaurants & conveniences of city. An incredible opportunity for those looking to escape the city without sacrificing convenience. Note this home has municipal water, hydro, gas and internet. A rare opportunity in the country
18805 Willoghby Road, Caledon
4+1
BEDS
4
BATHS
$1,840,000
FOR SALE
ABSOLUTELY Gorgeous ! ! ! ! Excellent Location! Beautiful 4 +1 Bedroom , 4 Bathroom Home With A 3 Car Garage And Workshop Sits On A Gorgeously Landscaped 1 - Acre Lot. Once You Enter Everything Is Just Gorgeous! Living & Family Rooms are Enough To Gather Visitors & Family, Kitchen Is Magnificent W/ Center Isle & An Eat-In. An Entertainers Dream Backyard With An In-Ground Pool , Hot Tub , Cabana , Multiple Decks & Sitting Areas. Located Only Minutes To Caledon Village & Only 10 Minutes To Orangeville. Close To Tpc Osprey Valley Golf Course .
12378 Mississauga Road, Caledon
4+2
BEDS
4
BATHS
$2,299,999
FOR SALE
Experience country-style living with city convenience in this beautifully renovated bungalow situated on a rare 1-acre lot with clear views along prestigious Mississauga Road. This exceptional property features numerous upgrades throughout, including elegant pot lights, modern finishes, and a spacious upgraded gourmet kitchen with a large breakfast bar perfect for entertaining and family living. The home offers 4+2 generously sized bedrooms and 4 upgraded washrooms, providing ample space and comfort. A separate entrance to the finished basement adds excellent flexibility, featuring a large recreation room and two additional bedrooms-ideal for extended family or potential rental income. Step outside to a beautifully manicured backyard offering a peaceful setting and endless possibilities for outdoor enjoyment or future expansion. include double car garage and an oversized driveway with parking for 10+ vehicles. Conveniently located just minutes from Brampton, this property offers the perfect blend of privacy, space, and accessibility to nearby amenities, making it a rare opportunity to own a stunning upgraded bungalow in a highly sought-after location.
13080 Centreville Creek Road, Caledon
4+2
BEDS
4
BATHS
$2,299,000
FOR SALE
Welcome to this beautiful home in Caledon, offering approximately 2,700 sqft of thoughtfullydesigned living space. Nestled on a fully fenced lot near the city, this residence features astriking blend of brick and stone construction. Inside, you'll find a spacious layout withfour bedrooms, with an additional two bedrooms in the finished basement. The basement includesa separate entrance, perfect for extended family or guests. The main floor is enhanced withnew kitchen upgrades, elegant porcelain tiles, and a vaulted ceiling in the living room, wherea cozy wood-burning fireplace awaits. The home also includes a unique loft space behind thegarage for extra storage. This stunning home also boasts an impressive 21 parking spaces!Whether you're hosting gatherings, have multiple vehicles, or need ample space for RVs andguests, this property has you covered. The expansive driveway and dedicated parking areaprovide unmatched convenience and flexibility for your lifestyle. Enjoy the peace of mind thatcomes with having plenty of room for everyone and everything. This home truly offers the bestin comfort and practicality don't miss out on this one-of-a-kind opportunity!
33 Gibson Lake Drive, Caledon
3
BEDS
4
BATHS
$2,149,000
FOR SALE
Nestled in the rolling hills of Caledon, this stunning Palgrave residence offers the perfect balance of rural tranquility and upscale living. Renowned for its scenic beauty, spacious properties, and welcoming community, Palgrave remains one of the most desirable areas near the Oak Ridges Moraine-ideal for families, retirees, and nature lovers alike. Situated on just over 2 acres of private land, this move in ready dream home has been extensively renovated in 2025, showcasing: A brand-new custom kitchen with quartz countertops and top-of-the-line appliances. Upgraded flooring throughout. A newly designed powder room, office, and laundry room. A luxurious primary suite featuring a spacious walk-in closet with custom organizers throughout for easy access and a spa-inspired ensuite with heated floors and a large walk-in shower. An additional fully renovated upper bathroom, also with heated floors for year-round comfort. Step outside to your own private oasis, complete with a large inground pool. Set against serene views of nature. An oversized double garage plus parking for up to 8 vehicles ensures plenty of space for family and guests.This home is the perfect blend of comfort, elegance, and lifestyle ready for you to move in and enjoy.
13924 Kennedy Road, Caledon
4+2
BEDS
2
BATHS
$1,999,999
FOR SALE
An Exceptional Opportunity - Severance Approved After 7 Years of Hard Work. Severance has finally been approved, unlocking a rare and valuable opportunity. Ideal for two brothers, friends, or investors looking to build custom dream homes side by side in a highly desirable area. Surrounded by luxury custom-built homes, this property offers the perfect setting for upscale development while still enjoying the charm of its current residence. Situated on approximately 1.2 acres, the property features a well-maintained bungalow with: Open-concept main floor, Gourmet kitchen with ample cabinetry, four spacious bedrooms, Finished basement with a large bedroom and full washroom. Additional highlights include a double car garage and a separate rear workshop, providing extra functionality and storage. Conveniently located just minutes from Highway 410 and Brampton, offering easy access to major routes, amenities, and city conveniences. MUNICIPAL WATER AND GAS ON THE PROPERTY LINE.
DIALOG CONTENT
Would you like to receive Similar Listing Alerts as soon as they are uploaded to MLS®?
How would you rate our website?
Would you like to rate us on Google?
Yes
231182361