14294 Winston Churchill Boulevard

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.

Discover a rare historic estate in the charming village of Cheltenham. Set on 1.4 private acres with approximately 200 feet of frontage this 1862 residence blends timeless character with thoughtful modern updates. Enjoy walking proximity to the General Store, Credit River, Caledon Trailway, and the Badlands, with Pulpit Golf Club, Caledon Ski Club, cafés, and breweries only minutes away. Pearson Airport is a quick 30-minute drive. A stately tree-lined drive leads to over 3,700 square feet of bright, inviting living space. Tall windows, high ceilings, and generous principal rooms create an open, airy feel throughout. The flexible layout includes four bedrooms, three bathrooms, a family room, dining room/library, office/living room, and a versatile loft ideal for studio, fitness, or creative use. Utilize this fantastic property as a family home, weekend retreat from the city or unlock the potential of the property by exploring the possibility of lot severance. Modern geothermal heating and cooling - along with radiant heat on all tiled floors - provide efficient, eco-friendly comfort year-round. Outdoors, enjoy multiple patios, a sunlit solarium, a landscaped pond, and mature trees offering complete privacy. The wide frontage also offers A one-of-a-kind heritage offering in one of Caledon's most beloved villages, where historic charm meets modern living.

JUST ONE WORD !! WOW !! Nestled on 48 acres of picturesque countryside, this property is a sanctuary of endless possibilities. The original barn, boasting two levels of extra space, invites creativity for a home-based business or personalized workshop. Step inside the charming house, where character abounds with old wood beams, offering a romantic country lifestyle. Enjoy the tranquil pond and explore trails enveloped by trees, perfect for snowmobile rides or peaceful jogs. The home is designed for year-round comfort, featuring a hot water tub, a family room ideal for entertaining with a pool table, and recent upgrades including a heat pump, furnace, and AC. With over 50 dark walnut trees gracing the property, this is truly a must-have retreat. HAT PUMP 2023 AC 2023 Welcome to your oasis, where every season brings its own magic. Don't miss out on this captivating opportunity.

Understated luxury, embraced by nature. Welcome to 19231 Shaws Creek Road, a refined residence where understated luxury meets the calm of protected greenspace. Thoughtfully designed and beautifully maintained, this exceptional 3 bedroom and 3 bathroom custom built by Goodland Homes Cape Cod home offers a rare blend of privacy, elegance, and everyday convenience. Set against a tranquil natural backdrop, the home backs directly onto lush green space, creating a sense of seclusion while still being just minutes from shops, schools, dining, golfing, and major commuter routes. Inside, the layout is both functional and inviting - ideal for daily living and effortless entertaining. Recently renovated, immaculately maintained. High-quality finishes, focus on natural materials, timeless design elements, and an abundance of natural light reflect a quiet sophistication throughout. Whether you're enjoying peaceful mornings overlooking nature or hosting friends and family in warm, well-appointed living spaces, this home delivers a lifestyle defined by comfort, balance, and refinement. A rare opportunity to enjoy luxury without excess, nature without compromise, and convenience without sacrifice-19231 Shaws Creek Road is truly a place to call home. Luxury certified.

Welcome to 12777 Mississauga Rd in Caledon. This raised bungalow sits on 1.03 acres with 3 bedrooms and 2 full bathrooms. Additional living space in the lower level featuring a cozy wood fireplace. Extra long driveway that shields the house from the street allows for ample parking space and privacy. The beautiful treed lot with farmer's fields behind the property creates an environment punctuated by nature and tranquility. Large separate workshop in the back yard is perfect for all types of projects. Very close to Brampton and Georgetown. Easy access to Hwy 410, 401, 407 and Go Station. This home is nestled in the countryside, yet conveniently located minutes from bustling urban centers, offering the best of both worlds. Backyard BBQs on the deck and family reunions complete with a game if volleyball or three legged races, ending the evening with roasting marshmallows over a fire pit. If this sounds like an ideal summer weekend to you, then this house is for you!

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.

Discover the ideal harmony of tranquil country living and urban convenience at this meticulously maintained property in prestigious Caledon. This exceptional 3+2 bedroom, 4-bathroom home sits on a private 1-acre lot, offering luxury amenities and stunning natural surroundings just minutes from Brampton, Bolton, and Vaughan. This home offers an open-concept main floor with beautiful new hardwood flooring throughout. The gourmet kitchen boasts built-in new appliances, quartz countertops, and a large pantry. The family and dining rooms open onto an extra-large deck that overlooks peaceful natural surroundings, creating the perfect space for relaxing and entertaining. Step outside to enjoy a fully landscaped property set on 1 acre of serene land, complete with an extra-large fire pit, and In-ground Swimming pool in the backyard ideal for family fun and outdoor gatherings. The walk-out lower level features a private two-bedroom, a rec. room and game area offering excellent flexibility for kids or extended family. This house is within top rated school boundary. This is upgraded house- includes New Hardwood flooring(2025), New Kitchen with quartz (2025), New kitchen appliances (2025), Fully renovated 3 washroom (2025), New LED light sand other light fixtures (2025), New closet doors & room doors (2025), freshly painted (2025), roof vent cover replacement(2025), New Gutter with leaf guard and downspouts (2025), Comprehensive duct cleaning (2025).

Welcome to 211 Pine Avenue - a stunning, brand new custom-built bungalow offering over 3,600 sq ft of finished living space on a premium lot with a private pond. This bright, open-concept home features hardwood flooring, pot lights, and oversized windows showcasing tranquil green views. The gourmet kitchen boasts quartz countertops, stainless steel appliances, a bold island, and walkout to a private balcony. The primary suite includes a walk-in closet and spa-like ensuite. Recent upgrades include new front and back interlock (2025), hydro-seeding (2025), and a new septic system installed August 2025. Enjoy a 3-car tandem garage with parking for 11 vehicles. Steps to Palgrave Stationlands Park, Caledon Equestrian Park, and scenic trails - where luxury meets nature in the heart of Palgrave.

One of Kind! Custom built executive 4 bed, 3.5 bath bungalow offering 3145 sq ft of beautifully finished space with open concept main floor! Nearly 6300 sq ft in total! A stunning cathedral ceiling spans the kitchen and living room, and centres upon the cozy stone-clad fireplace. The interior finishes are elevated with recessed lighting and wide plank hardwood floors throughout. The show-stopping white and wood kitchen with gleaming quartz counters is sure to impress. Both the main floor laundry room and Primary walk-in closet feature upgraded floor-to-ceiling cabinetry for ample storage and quartz counters. The Primary bath is a delight that offers a free-standing tub, private water closet, double vanity and glass shower. Enjoy quiet evenings on the quaint front porch or covered rear deck. So much more to see! Generous 100 x 150 ft lot on quiet street in sought after Caledon Village. Full Tarion New Home Warranty. Awesome commuter location - 15 mins to Brampton or Orangeville! Anticipated completion January 2026.

Great Opportunity To Invest In fastest growing Development Area of Bolton(Caledon). Bolton west secondary plan is underway ( See Attachment).New planned highway 413 exit will be on humber station rd just few kilometers south of this property , Fully Renovated (Move-In-Condition) 4+2 Bdrm & 3 Baths Solid Brick Bungalow On 1 Acre (150feet X292.7feet) Lot & Drawing Already Approved To Build Custom Home Main & 2nd Flr 7486 Sqft. + Bsmt 3374 Sqft ( See Attachment). Huge Bungalow With Brand New Modern Kitchen (2022) W/Stainless Appliances, New Quatz Counter Top & Backsplash (2022) Modern New Floor Tiles (2022) Updated All 3 Baths (2022) Mbr W/4Pc Ens. & Closet. Liv/Din W/Pot Lights & Bay Window}} Huge Family Rm W/Fire Place & Pot Lights}} 20 New Exterior Pot Lights (2022) New Garage Doors (2022) W/Openers}} 2 Bdrm Huge Bsmt W/New Kitchen (2022) & Own Laundry .New Laminate (2022) Lots Of Development Coming In The Neighborhood. huge Potential. The Home Is Well Set Back From The Road Offering Peace And Quiet. Very Close To Bolton, Future Go Train Station & Amazon + Canadian Tire Warehouse .

Luxury Executive Detached Estate Home in the prestigious Osprey Mills community, situated on a spacious 3/4 acre lot. Offering 3,252 sq. ft. above grade, this home features 10 ft ceilings on the main floor and 9 ft ceilings on the second floor and basement. Designed with engineered hardwood floors, quartz countertops, and 24x24 tiles on the main level.

Client RemarksLuxury 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.

Welcome To This Fully Renovated, Absolutely Stunning Spacious 5 level with functionality and privacy, On 2 Acres Private flat Lot. 4 Bedrooms & 3 Full and a half Bathrooms. Primary bedrm with 4 pc ensuite along with 3 spcious bedrms. Brand New Hardwood Floors Thru Out The Home. Eat In New Kitchen W/Granite Countertop & Backsplash. W/O Family Rm W Gas Fireplace & Main Floor Laundry. Double Drive For 17 Cars Parking. All New Washrooms With Porcelean Tiles & Glass Enclosed Showers. Seprate detched, 20 By 30 Foot Concrete drive in garage W/Electricty and water. Perfect For toys And Storage. Roof has 50 years shingles . Most windows replaced. Live Ur Dreams Minutes To Hwy 400 And City Amenties.

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 .

Where country serenity meets city convenience, this exceptional 5-acre property sits perched on a hill just steps from Terra Cotta and the Credit River. Nestled in an exclusive enclave of executive homes, it offers privacy, space, and a connection to nature at every turn. Ideal for multigenerational living, the residence includes a fully self-contained, beautifully finished 2-bedroom in-law suite. The home is thoughtfully designed with a stunning family-sized kitchen that opens onto a large deck overlooking the peaceful landscape. The main level features formal living and dining rooms, three generous bedrooms, and a primary retreat complete with walk-in closet and private ensuite. The lower level provides versatility with a spacious recreation room and office. Both kitchens and all four bathrooms have been updated for modern comfort, while geothermal heating and cooling, natural gas, Rogers high-speed internet, town water, and a 3-car garage enhance everyday functionality. Outdoor enthusiasts will love the easy access to skiing, golfing, and hiking in the Caledon Hills right outside your door.

Exceptional Detached Home on a 12,000 Sq Ft Lot in the Heart of Bolton. Welcome to this stunning 2-storey fully detached home situated on a rare flat lot backing onto a serene ravine. Completely rebuilt interior and custom-renovated just 4 years ago, this home offers luxury, space, and functionality minutes from all amenities. Featuring a resort-style backyard with an in-ground pool, jacuzzi, stamped concrete, outdoor kitchen and an expansive 1,500 sq ft maintenance-free vinyl deck with forever vinyl fencing - perfect for entertaining or relaxing in total privacy. Inside, enjoy a thoughtfully designed layout with second-floor laundry, a modern kitchen, and quality custom finishes throughout. The walk-out basement apartment includes 2 bedrooms and a full bath, ideal for extended family or rental income.

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!

Welcome to 7 Golfdale Court in Prestigious Caledon Woods Estate; a truly remarkable bungalow offering 3+2 bedrooms, tucked away on a quiet cul-de-sac and set on nearly 1.5 acres of beautifully landscaped grounds, and **Built in 2007, making it one of the newer homes in the area**. This exceptional home offers a seamless blend of comfort and sophistication. Step into a thoughtfully designed interior featuring sunken formal living and dining spaces, ideal for hosting guests, along with a warm and inviting family room with a cozy ambiance. The gourmet kitchen is a culinary dream, complete with a breakfast area and walkout to a spacious deck overlooking your private backyard oasis. The main floor is highlighted by a bright and spacious primary retreat with a walk-in closet and a 4-piece ensuite, along with two well-appointed bedrooms, a full main bathroom and a versatile office that can easily be converted into a fourth bedroom. A convenient laundry/mudroom provides direct access to the heated 3-car garage. Additional highlights include a sprinkler irrigation system for easy lawn maintenance and beautifully manicured grounds. Downstairs, the finished lower level offers an open concept design, perfect for entertaining or multi-generational living, featuring a large recreation area, two additional bedrooms, a 3-piece bath, and a dedicated storage room. Surrounded by natural beauty and tucked in an exclusive neighborhood, this property offers peace, privacy, and refined living just minutes from all essential amenities.

A rare Caledon 1 Acre property offering a massive 30x40 heated & insulated detached shop/garage, a sprawling bungalow with a fully finished walk-up basement, and close to 4,000sq.ft. of total living space - this property is built for buyers who need space, storage, and serious functionality without sacrificing comfort. Set on a private, sprawling , level 1-acre lot along the desirable Torbram corridor, this 6 bedroom home delivers the perfect mix of country privacy and GTA convenience. The standout detached Heated and insulated workshop is ideal for car enthusiasts, tradespeople, hobbyists, home-based businesses, or anyone who simply wants a true dream garage - fully powered and backed by an 20 kW Briggs & Stratton generator that runs both the house and shop during power outages. The bright, spacious main level features a beautiful light filled living room and formal dining area. The updated kitchen shines with solid hardwood cabinetry, granite countertops, under-cabinet lighting, stainless steel appliances ('22), and a skylight with custom wood detailing that fills the space with natural light. The primary suite includes a walk-in closet and a beautifully updated ensuite with heated flooring. Two additional generous bedrooms and two newly finished bathrooms complete the main floor, offering modern finishes and thoughtful upgrades throughout. The fully finished walk-up basement significantly expands your living space with two additional bedrooms, 1 full bathroom, a recreation room, games room, and ample storage - making it ideal for extended family, guests, or a private work-from-home setup. Outside, enjoy your new deck and screened-in gazebo ('23) and a newly paved driveway and concrete pad ('22). Major updates include: new furnace & A/C ('20), new windows and patio doors ('16), house roof ('16), shop roof ('21). If you've been searching for acreage, space, and a true 30x40 dream garage in Caledon - this is the one.

A rare offering on one of Palgrave's most sought-after estate streets. Set on a picturesque 2.14-acre lot, 12 Matson Drive blends privacy and natural beauty in an exceptional raised bungalow. Surrounded by mature trees and frequently visited by local wildlife, this home offers a peaceful lifestyle just minutes from local amenities. Inside, natural light fills the spacious layout through oversized windows. Two inviting living rooms with a gas fireplace and the other with a wood-burning fireplace provide cozy gathering spaces for all seasons. The primary bedroom features large windows, a walk-in closet, and a private ensuite. The kitchen includes a gas burner, grill and fridge (sold as-is), with additional newer fridges located throughout the home. The lower level offers flexible space, including a room with a sink ideal for extended family or future in-law suite potential (buyer to verify local zoning). Recent upgrades include a new furnace (2025), water softener (2025), owned tankless water heater (2025), dishwasher (2025), new wood deck (2025), and modern glass deck railing (2025), and new Chamberlain garage doors (2025). A generator is housed in the garage. The oversized 3.5-car garage offers ample space for parking, storage, and tools. The gently sloping rear lot provides a serene, forested backdrop and endless potential for outdoor enjoyment. Skavana robot lawn mowers included. Appliances included in as-is condition. A rare opportunity to own a well-maintained, light-filled home in a highly desirable estate setting. Book your private showing today to experience 12 Matson Drive.

An Architectural Masterpiece Nestled On An Expansive 0.84- Acre Lot In The Prestigious Valley of Bolton. This Opulent Estate Embodies Unparalleled Elegance and Exquisite Craftsmanship. Designed For the Discerning Buyer, The Home Boasts 9-Foot Ceilings On the Main Floor, An Awe-Inspiring 30-Foot Foyer That Opens To Three Levels, Dual Scarlett O'Hara Staircases That Gracefully Wind Through The Residence. The Family Room And Primary Suite Feature Breathtaking Cathedral Ceilings, While The Custom Millwork, Wainscotting, And Intricate Crown Moulding Throughout Showcase The Home's Refined Artistry. The Gourmet French Inspired Maple Kitchen Is A Culinary Dream, Complete With Built-In KitchenAid And Miele Appliances, Granite Countertops, An Oversized Custom Hood, And A Two-Level Island With a Warming Drawer. The Walk-Out Basement, An Entertainer's Haven, Features A Stunning 12-Foot Mahogany And Brass Bar, A Gas Fireplace Framed By A Decorative White Stone Accent Wall, And Expansive Picture Windows That Bathe The Space In Natural Light. A Private Loft Offers A Tranquil Escape, While Smart Home Automation, A Multi-Room Audio System, And Newly Installed 4K Intelligent Cameras Ensure Modern Comfort And Security. Luxurious Imported Materials Adorn Every Corner, From The Hand-Carved Limestone Fireplace Mantle To The Marble-Inspired Porcelain Flooring. This Estate Epitomizes Sophisticated Living, Seamlessly Blending Grandeaur With Functionality In A Coveted Location Steps From The Humber River.

Set On A Serene 1.025-Acre Estate With Sweeping Scenic Views, This Custom-Built 2007 Bungalow Showcases Exceptional Craftsmanship And Timeless Luxury. The Main Floor Impresses With 9-Ft Ceilings, Rich Hardwood Flooring, Elegant Pot Lighting, And Refined Finishes That Elevate Every Space. The Gourmet Chef's Kitchen Features Premium Appliances, Custom Cabinetry And A Spacious Eat-In Area Designed For Both Casual Dining And Elevated Entertaining. The Master Suite Offers A Private Sanctuary Complete With A Spa-Inspired Ensuite, Featuring A Jacuzzi Tub, Steam Shower, And Heated Floors. The Lower Level Continues The High-End Feel With 9-Ft Ceilings, A Full Bathroom With Heated Floors, Two Generously Sized Bedrooms, And More Than Half Of The Basement Left Open As A Customizable Canvas For A Theatre, Gym, Or Entertainment Lounge. The Backyard Boasts An Expansive Deck With Glass Railings, Perfect For Summer Enjoyment, Scenic Views, And Unforgettable Sunsets. Nearly $120K In Upgrades Ensure Modern Comfort and Sophistication Throughout. Car Enthusiasts And Hobbyists Will Appreciate The Expansive Heated 4-Car Garage, Boasting Impressive 14-Ft Ceilings And The Flexibility To Double As A Workshop. Offering Elegance, Privacy, And Endless Potential, This Remarkable Residence Is The Perfect Blend Of Luxury Living And Functional Design-An Extraordinary Opportunity For The Discerning Buyer.