Caledon Real Estate Search

Caledon 6+ Bedroom Properties for Sale

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Newest Caledon 6+ Bedrooms Properties for Sale

$2,899,000
6 Beds 6 Baths W13771530 MLS
Timeless elegance meets impeccable craftsmanship in this stunning Cheltenham estate. A rare find, this beautifully built 5+1 bed, 6 bath home in the sought-after Cheltenham community offers thoughtful design & exquisite details throughout. Chefs kitchen blending beauty & practicality, featuring a 48" Wolf gas range, Sub Zero fridge/freezer, Bosch dishwasher, built-in microwave, & custom quarter-sawn oak cabinetry. 5" solid white oak floors create an inviting atmosphere. The natural beauty of tumbled limestone, natural stone & marble in the kitchens, baths, & basement enhances the spaces timeless elegance, combining sophistication w/ comfort. The primary suite is a true sanctuary w/ heated floors, a spa-like steam shower, a romantic soaker tub, a spacious walk-in closet & focal fireplace. Every detail has been thoughtfully considered, from coffered ceilings in the dining room to vaulted ceilings in the family room & sunroom, adding architectural charm & grandeur. The main floor also includes a dedicated office, perfect for WFH or quiet study. Upstairs, 3 beds each w/ walk-in closets. Two share a Jack-&-Jill bath, while the 3rd has its own private ensuite creating private retreats for family & guests. Every detail, from custom millwork & extensive closet systems to solid wood doors, reflects timeless quality. Step outside to a beautifully landscaped yard, complete w/ irrigation system & a grand outdoor stone fireplace. The property boasts nearly an acre of lush grounds, with a 3-car garage plus an additional backyard workshop garage w/ a loft ideal for toys, landscape equipment & hobbies. For added versatility, theres a bright, welcoming 1-bed, 1-bath loft apartment w/ its own entrance, walk-in closet & separate laundry perfect for in-laws or rental income. The finished basement offers even more comfort w/ guest bed & bath, media & game zones, a bar, crafts room, gym, & a ton of storage, creating a warm, inviting and functional space for gatherings & daily life.

84 Kennedy Road, Caledon

$1,599,000
7 Beds 6 Baths W13768250 MLS
Showstopper! Welcome To This Fully Upgraded Corner Home In A Prime Caledon Location, Offering3,224 Sq. Ft. Of Above-Grade Living Space Plus Two Finished Basement Apartments. With Over$350K Invested In Upgrades, This Home Features A Striking Stone And Brick Exterior, Approximately $90K In Professional Landscaping, And Full Interlocking Across The Front, Around The House, And Throughout The Entire Backyard. The Large Rear Deck And Front Porch Feature Glass Railings, While Exterior Pot Lights Add Beautiful Curb Appeal. The Bright, Spacious Interior Offers 9-Ft Ceilings On The Main Floor, Smooth Ceilings, Pot Lights & California Shutters Throughout, Large Windows, And An Abundance Of Natural Light. No Carpet Anywhere, With Hardwood Flooring And Wood Staircases Throughout, Including Both Staircases. The Upgraded Two-Tone Kitchen Features Upgraded Countertops, Upgraded Backsplash, And An Upgraded Custom Range Hood. Additional Main-Floor Highlights Include A Formal Dining Room And Gas Fireplace. The Primary Bedroom Offers Two Walk-In Closets And A 5-Piece Ensuite, While Every Additional Bedroom Upstairs Features Ensuite Access. Approximately $100K Was Invested In The Finished Basement, Complete With A $15K Separate Side Entrance From The Builder. The Basement Includes One 1-Bedroom Apartment And One 2-Bedroom Apartment, Each With A Separate Kitchen, Full Bathroom, And Laundry. A Double-Car Garage And 6 Car Driveway Provide Parking For 8 Vehicles. A Beautifully Finished, Move-In-Ready Home Offering Luxury, Space, And Versatility Inside And Out. **Legal Basement Apartment**

1 Breckonwood Street, Caledon

$3,450,000
6 Beds 5 Baths W13767138 MLS
The Beech House stands well back on 2.55 wooded acres, screened from the road. A modern house of more than 4,000 square feet, rebuilt from the studs out to the tree line - over a million dollars of renovation since 2020. A planted courtyard leads to an entry walled in glass. Inside, an open staircase climbs beneath an atrium that pours daylight into the centre of the house. The kitchen anchors the main floor with a long centre island, wall ovens and a sunlit breakfast area. The living room lies beyond, opening to a screened-in covered porch with a pizza oven. A few steps down, the sunken family room. Set on its own, a formal dining room with bar. Three bedrooms occupy the main level, one with a private ensuite - a full life on one floor, should it suit. Above, the primary suite: banks of closets, a spa ensuite with double vanities, freestanding soaking tub and separate shower, and a private balcony in the treetops. A fifth bedroom completes the level. Engineered hardwood and tile throughout; two baths heated underfoot. The grounds are the revelation. A stone terrace runs along the back of the house, with a pergola for long dinners at one end and a hot tub, cold plunge and barrel sauna tucked into the trees. Stepping stones cross the lawn to a circular fire pit terrace. Past the gardens, at the far edge of the lawn, a pond with a fountain sits against the woods. Above the detached garage, a self-contained guest suite with its own entrance: bedroom, bath, living room, dining area and kitchen which is turn-key and furnished. For those tempted to take the look along with the house, select furnishings can be available for purchase. The essentials are handled - furnace 2025, house A/C 2021, guest suite A/C 2026, Culligan UV, softener and reverse osmosis, insulated crawl space, EV charger compatible outlet, Lorex cameras, driveway 2024, culvert 2026. Minutes from Orangeville and the Caledon trails, and quiet the moment you turn in off the road.

3285 Beech Grove Side Road, Caledon

$3,950,000
6 Beds 5 Baths W13761544 MLS
Among the finest homes in Caledon. Set high on a hill across nearly 14 acres, surrounded by mature forest, where wild English gardens meet the clean, sharp lines of a gorgeous modern farmhouse. Private, and entirely its own. Completed in 2022 and built to hold the light and the landscape in equal measure. At the centre of the home, an open-concept kitchen, living and dining space anchored by a statement fireplace and wrapped in floor-to-ceiling corner windows that pull the forest inside from sunrise to last light. The kitchen balances marble, warm wood tones and custom detailing with luxe Fisher & Paykel appliances. A beautiful pantry and custom wine room sit just beyond. Views from nearly every room. The ideal family home. A handsome home office with custom built-in bookcase and rolling ladder, perfect for working from home. Off the kitchen, a mudroom and laundry connect to the two-car garage, with a dedicated dog wash. Upstairs, the primary reads as its own wing. Walk-out balcony, generous walk-in closet, five-piece spa-like ensuite. Designed with the ever-growing family in mind, the floor plan offers 4+2 bedrooms and 5 bathrooms, every bedroom with its own ensuite, and a main floor play room with the flexibility to become a co-primary suite. Below, a full basement with oversized window wells that bring daylight right through the lower level. Newly landscaped with professionally designed gardens and plantings, irrigated throughout. A fully fenced backyard made for dogs, kids and long summer nights. A handcrafted Sip Sauna, built to traditional Finnish standards, sits alongside a wood-burning hot tub overlooking the lush lawn. The ideal weekend escape, without leaving home. A modern farmhouse with the soul of a country house, and the craftsmanship to match.

3045 Highpoint Side Road, Caledon

$1,399,000
6 Beds 4 Baths W13755100 MLS
Welcome to this beautifully upgraded family home, perfectly positioned on a premium corner lot in one of Bolton's most desirable neighbourhoods. Offering an impressive combination of space, style and functionality, this move-in-ready residence features 4 spacious bedrooms above grade plus 2 additional bedrooms in the newly finished basement, providing exceptional flexibility for growing or multi-generational families. The home showcases 4 beautifully renovated bathrooms with elegant marble finishes, hardwood flooring throughout the principal living areas and most bedrooms, and a bright, thoughtfully designed layout filled with natural light. The formal living room is highlighted by a sophisticated coffered ceiling and large picture window, while the separate dining room creates an inviting setting for entertaining. At the heart of the home is the stunning custom-built kitchen, featuring sleek modern cabinetry, porcelain surfaces, an oversized centre island and premium appliances, including an impressive professional-style 8-burner double-oven range. The adjoining family room offers a warm and comfortable gathering space with hardwood flooring, a gas fireplace and large windows. Downstairs, the newly finished basement significantly expands the living space with 2 bedrooms, a modern 3-piece Italian marble bathroom with an oversized shower and versatile space ideal for extended family, guests, recreation or a home office. Additional conveniences include main-floor laundry, direct access to the double-car garage and central vacuum. Outside, enjoy the added privacy and presence of the corner lot along with a spacious backyard and deck, perfect for relaxing or entertaining. Ideally situated close to schools, parks, recreation, shopping, restaurants and everyday amenities, with convenient access to major commuter routes. A beautifully updated Bolton home offering exceptional space, quality and versatility for today's family.

63 Humbershed Crescent, Caledon

$2,049,000
6 Beds 5 Baths W13753596 MLS
Welcome to this private country retreat offering peaceful 2.6 acres of rural living, flexible space, income potential, and convenient access to nearby towns. Set on a quiet road with beautiful valley views and sought-after southwest exposure, this home is filled with natural light throughout the day. Ideally located just minutes to Tottenham, Schomberg, Bolton, Nobleton, Highway 9, the Caledon Rail Trail, scenic walking trails, Vince's Market, and the LCBO. The home features a dedicated main-floor office overlooking the front yard and a spacious lower-level gym with a full bathroom, large window, and walkout to the backyard. The lower level offers excellent flexibility for a guest suite, additional bedroom, recreation room, studio, or workspace. Outdoor living includes a large custom deck (2022), swim spa (2022), brand-new rollaway swim spa cover (2026), infrared sauna, sprinkler system, and shed on a concrete foundation (2022), all designed for relaxing and entertaining with sunset views. A fully self-contained heated floor nanny/in-law suite provides exceptional versatility and is currently generating approximately $2,400/month in rental income. The suite includes its own laundry, updated appliances, and an accessible walk-in shower, ideal for multi-generational living or mortgage support. Additional features include an oversized 4-car tandem garage with an extended bay and direct deck access, plus a large, professionally paved driveway with ample parking. Extensive updates include 19 replacement windows (2019 & 2025), upgraded well water system with new pressure tank and whole-home filtration, reverse osmosis systems in both units, new washers and dryers in both homes, updated appliances, additional spray-foam insulation, roof (2015), driveway (2018), and more. A well-maintained property offering space, flexibility, income potential, and a peaceful country lifestyle just minutes from everyday conveniences.

4 Tranquility Court, Caledon

$1,178,800
6 Beds 5 Baths W13744780 MLS
A TRUE SHOWSTOPPER A SEPARATE LEGAL 2-BEDROOM BASEMENT APARTMENT WITH ITS SEPARATE LAUNDRY! Welcome to this beautifully upgraded home where modern design meets everyday functionality. Featuring 9-ft ceilings on both the main and upper levels, thoughtfully selected finishes, this home offers versatile living space throughout. The upgraded kitchen is designed to impress, featuring an extended island, crown-moulded cabinetry, upgraded pantry storage, quartz backsplash, gas stove, stainless-steel hood, Samsung Smart refrigerator and Maytag dishwasher. Upgraded tile in the foyer and kitchen adds a polished finishing touch. Throughout the home, enjoy upgraded hardwood flooring in all bedrooms, upgraded baseboards, contemporary chandeliers, zebra blinds, decorative wall paneling in the powder room, upgraded mirrors and smart deadbolt entry. Comfort and convenience continue with central A/C, smart thermostat, whole-home humidifier, Culligan water softener, EV charger and hardwired security cameras at the front entry, driveway and backyard. The legal 2-bedroom basement apartment adds valuable flexibility and features its own kitchen, laundry, full bathroom with tiled standing shower and floating vanity, spacious living/dining area, large windows, dedicated pantry and generous closet space. One bedroom includes a Murphy bed for added functionality. Outside, the property offers 4 total parking spaces including the garage, an interlock-paved driveway, fully fenced backyard, garden bed, Keter storage shed and gas BBQ line. The absence of a sidewalk provides additional driveway space, while the gravel side entry offers convenient access and easy maintenance. With stylish upgrades, functional spaces and a legal separate basement apartment, this home offers a well-rounded layout suited to a variety of living needs. Easy access to highways, Schools, Parks, Future Costco, Walking distance to Major Plazas, Dentist , Walk in Clinic and other Amenities. A MUST-SEE HOME!!

20 Calabria Drive, Caledon

$1,050,000
6 Beds 4 Baths W13744300 MLS
Welcome to 7 Salt Creek Terrace-an exceptional East-facing detached home that perfectly blends sophisticated design, modern comfort, and outstanding income potential. Offering 3+1 spacious bedrooms, 4 beautifully appointed bathrooms, and a fully finished 1-bedroom plus den basement apartment with a separate entrance, this remarkable property is ideal for growing families, multi-generational living, or savvy investors. From the moment you enter through the grand double-door entrance, you'll be impressed by the elegant finishes throughout. Featuring 9-foot ceilings on both the main and second levels, smooth ceilings, upgraded 8-foot interior doors, designer pot lights, and a stunning hardwood staircase, every detail has been thoughtfully selected to create a bright, refined living space. The heart of the home is the spectacular chef-inspired kitchen, showcasing rich cabinetry, granite countertops, a spacious centre island, stainless steel appliances, and an open-concept layout that flows seamlessly into the living and dining areas-perfect for everyday living and effortless entertaining. Retreat to the luxurious primary suite featuring a generous walk-in closet and a spa-inspired 4-piece ensuite complete with a separate glass shower. Convenient upper-level laundry, spacious secondary bedrooms, and beautifully designed bathrooms provide comfort and functionality for the entire family.The professionally finished basement apartment with its own private entrance offers incredible flexibility-ideal for rental income, in-laws, or extended family. Complete with ample parking, excellent curb appeal, and a desirable location close to top-rated schools, parks, shopping, restaurants, transit, and major commuter routes, this exceptional home truly has it all.A rare opportunity to own a turnkey home that combines timeless elegance, premium upgrades, and exceptional value in one of Caledon's most sought-after communities.

7 Salt Creek Terrace, Caledon

$1,999,900
8 Beds 6 Baths W13742038 MLS
Welcome To 50 Stratford Drive, Caledon. A Luxury Residence Where Timeless Elegance Meets Modern Sophistication. Offering Approx. 3,713 Sq. Ft. Of Exceptional Living Space Plus A Fully Finished 3-Bedroom Basement, This One-Of-A-Kind Home Features Premium Upgrades Throughout. The Striking Stone & Brick Exterior, High-End Exterior Finishes, Elegant Double-Door Entry, And Distinctive Architectural Appeal Create Unmatched Curb Appeal In The Community. Inside, Soaring11-Ft Ceilings On The Main Floor And 10-Ft Ceilings On The Second Level & Basement Enhance The Grand Scale Of The Home. Rich Hardwood Flooring, Designer Light Fixtures, Smooth Ceilings, Crown Moulding, 7-Inch Baseboards, Coffered Ceilings, And Expansive Windows Showcase Exceptional Attention To Detail. The Gourmet Kitchen Is A True Showpiece, Featuring Upgraded Marble Countertops, Oversized Centre Island, Marble Backsplash, Extensive Cabinetry, And A Spacious Breakfast Area With Walk-Out To The Deck. The Open-Concept Layout Includes A Beautiful Family Room With Fireplace, Perfect For Entertaining And Everyday Living. The Luxurious Primary Retreat Features A Coffered Ceiling, His-And-Her Walk-In Closets, And A Spa-Inspired 5-PieceEnsuite. Additional Bedrooms Offer Generous Space, Walk-In Closets, And Semi-Ensuite Access. The Fully Finished Basement Offers 3 Bedrooms, A Full Kitchen, 2 Full Bathrooms, 10-Ft Ceilings, And A Separate Walk-Up Entrance, Providing Exceptional Flexibility For Extended Family Or Guests. Enjoy Your Private Backyard Oasis, Perfect For Relaxing And Entertaining. Additional Highlights Include Main-Floor Laundry, Garage Access, Separate Side Entrance, 200-AmpElectrical Service, Premium Lighting, And High-End Finishes Throughout. A Rare Opportunity To Own A Truly Exceptional Caledon Residence Combining Luxury, Space, Functionality, And Unmatched Curb Appeal.

50 Stratford Drive, Caledon

$2,299,000
6 Beds 6 Baths W13715192 MLS
This Custom-Built Caledon Estate Sitting On 3.74 Acres Of Manicured Grounds, Offering Unmatched Privacy, Breathtaking Presence, And A Lifestyle Reserved For The Exceptional. Completely Transformed With A Newly Redone Exterior Façade, Fresh Concrete Work, And Extensive Renovations Throughout, This Residence Delivers Modern Luxury Minutes From The City. Inside, A Grand Foyer Opens To A Soaring Family Room Open To Above, Elegant Living And Dining Rooms, A Private Main-Floor Office, And An Eat-In Kitchen Designed For Both Everyday Living And Upscale Entertaining With Outdoor Patio Access. A Spacious Mudroom And 3-Car Garage Complete The Main Level. Upstairs, The Primary Suite Is A True Retreat With A 5-Piece Spa Ensuite Featuring Double Sinks, Glass Shower, Freestanding Tub, Separate Water Closet, And Two Walk-In Closets. A Second Primary Enjoys Its Own 5-Piece Ensuite, While Bedrooms Three And Four Share A Stylish Jack And Jill Bath. A Fifth Bedroom Includes A Full Private Bath, And The Convenience Of An Upper-Level Laundry Room Elevates Daily Living. Hardwood Flooring Throughout Adds Warmth And Sophistication. The Lower Level Is An Entertainer's Dream With A Large Recreation And Bar Lounge, A Full Bedroom With Closet, A Luxurious Bath With Sauna, Ample Storage, And A Dedicated Indoor Basketball Court - A Rare And Extraordinary Feature. Step Outside To Your Personal Resort With An Inground Pool, Expansive Grounds, And Endless Space To Relax, Host, And Enjoy. A One-Of-A-Kind Offering Combining Land, Luxury, And Lifestyle. This Caledon Estate Defines Elevated Living. List Of Upgrades Attached.

6 Country Lane Drive, Caledon

$1,995,000
6 Beds 3 Baths W13700560 MLS
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.

6785 Highway 9 Road, Caledon

$4,299,000
7 Beds 8 Baths W13681670 MLS
**Welcome to an extraordinary custom-built luxury estate offering nearly 10,000 sq. ft. of refined living space in one of Caledon's most desirable estate communities** Enjoy the perfect blend of peaceful country living and urban convenience, just minutes from Brampton, Highway 410, and the future 413 corridor**This exceptional residence showcases timeless elegance, superior craftsmanship, and thoughtful design throughout**A striking 9-ft custom main entrance door, elegant 8-ft interior doors Soaring 11 ft ceilings on the main floor and 10 ft ceilings on the second floor and basement create a grand sense of space**The home offers 7 spacious bedrooms and 8 luxurious bathrooms, including a main floor bedroom with a private ensuite and walk-in closet, ideal for multigenerational living**The chef-inspired kitchen features premium Sub-Zero and Wolf appliances, custom cabinetry, an oversized waterfall island, and a full Size spice kitchen With Built In KitchenAid Appliances**Luxury continues with a Control4 smart home automation system, built-in speakers throughout, private theatre, dedicated gym, formal living and dining rooms,Central vacuum system with convenient in-wall retractable hose,"Spectacular 21-ft open-to-above foyer and family room, upgraded trim work with impressive 9.5-inch baseboards throughout, and upgraded triple-glazed windows throughout for enhanced comfort and energy efficiency." and a spacious 4 car garage**Energy efficiency and quality construction shine through with spray foam insulation across all exterior walls on all levels, an insulated basement floor for added comfort, dual high-efficiency furnaces, dual4-ton AC units, a Waterloo biofilter septic system, skylight, and a newer metal roof with a lifetime warranty**Professionally landscaped grounds and expansive interlock outdoor living spaces complete this truly one-of-a-kind estate where luxury, privacy, superior construction, and an outstanding location come together in perfect harmony.

14374 Kennedy Road, Caledon

$1,345,000
7 Beds 3 Baths W13621738 MLS
Welcome to this beautifully renovated 4 + 3 bedroom residence on an impressive 0.40-acre lot, offering a rare blend of modern design, functional living space, and picturesque surroundings. Thoughtfully updated throughout, this turnkey property presents an excellent opportunity for families, investors, or multi-generational living. Step inside to a bright, inviting interior featuring hardwood flooring throughout, contemporary light fixtures, and an abundance of pot lights that create a warm, elegant atmosphere. The home showcases custom window coverings, a redesigned kitchen with stylish cabinetry, and tastefully updated bathrooms, all completed with quality finishes and attention to detail. Outside, new exterior lighting and a freshly paved asphalt driveway enhance both curb appeal and convenience. The spacious family room is a focal point, highlighted by a cozy fireplace and a walkout to a private deck where you can relax while enjoying tranquil views of the expansive yard. The open-concept main living area is ideal for entertaining and everyday living, anchored by an entertainer's kitchen with a large central island that seamlessly connects to the dining and living spaces. Practical features further enhance functionality, including two main-floor bedrooms, a mudroom, and a separate laundry room designed for busy households. The recently completed fully finished basement with 3 additional bedrooms, providing flexibility for extended family, guests, or potential rental income. Adding to the home's versatility is an exterior staircase to the second level, creating the possibility for an in-law suite, private workspace, or multi-use living arrangement. With generous indoor and outdoor space, modern upgrades, and income potential, this property is a rare opportunity to own a move-in-ready home with room to grow. 24hrs notice required for viewings as property is tenanted

16045 Hurontario Street, Caledon

$3,999,999
6 Beds 7 Baths W13621500 MLS
Welcome to an extraordinary private estate set on over 38 acres in the rolling countryside of Caledon. This rare offering combines luxury living, natural beauty, and future potential with approximately 1,800 ft of frontage and possible estate residential development potential (buyer to verify). The residence offers over 5,300 sq ft of total living space with breathtaking views of the surrounding landscape, including a serene pond and approximately 12 acres of forest. Expansive windows flood the home with natural light while framing stunning northwest-facing vistas.Featuring 4+2 bedrooms and multiple living areas, the home is ideal for family living and entertaining. Enjoy two wood-burning fireplaces, a walk-out lower level, and seamless indoor-outdoor flow to a large deck overlooking the peaceful setting. The property also includes a detached 6-car, 900 sq ft shop, offering ample space for vehicles, hobbies, or storage.Private trails wind throughout the property, creating a true retreat-like experience with endless outdoor recreation opportunities. Located in one of Caledon's most sought-after rural enclaves, just a short drive to Orangeville, Erin, and major commuter routes, this property delivers the perfect balance of privacy and convenience.Important Disclaimer: Proposed severance/subdivision concepts are preliminary only and subject to approvals from all governing authorities. Seller and Listing Brokerage make no representations or warranties regarding approvals, rezoning, development potential, servicing, or future use. All information, measurements, dimensions, acreage, and development concepts are approximate and subject to change without notice. Buyers must conduct their own independent due diligence regarding zoning, permitted uses, development potential, environmental matters, servicing, taxes, permits, and planning requirements through their own professional advisors. Property being sold "as is, where is."

4175 Beech Grove, Caledon

$10,900,000
7 Beds 5 Baths W13589386 MLS
WOODLANDS is an extraordinary 7-bedroom, 5-bathroom estate offering two distinct residences set on approximately 63 private acres of mature forest, scenic trails, and meticulously landscaped gardens. Perfectly positioned at the prestigious corner of Escarpment Sideroad and St. Andrews Road, surrounded by grand country estates and directly across from Paintbrush Golf Club, while just minutes to Devil's Pulpit Golf Association. The main residence is highlighted by a breathtaking 14-foot floor-to-ceiling great room and an elegant open-concept marble and onyx kitchen. A dramatic two-sided floor-to-ceiling fireplace beautifully separates the principal living and dining rooms, while expansive wraparound terraces provide seamless indoor-outdoor living from every principal space. Two luxurious primary suites each feature walk-in closets and spa-inspired 5-piece ensuites. The walk-out lower level is designed for exceptional entertaining, complete with a spacious family room, wine cellar, recreation area, mirrored fitness studio, two above-grade bedrooms, and a custom 10-person wet bar. The contemporary Pool House offers two additional bedrooms, dramatic floor-to-ceiling windows, a spacious 3-piece wet room, and stunning views over the infinity-edge pool and hot tub. Outdoor entertaining is equally impressive with an expansive dining terrace, championship tennis court, beautifully manicured gardens, woodland walking trails, and a tranquil fire pit setting surrounded by towering pines. Offering approximately 6,000 sq. ft. of total living space, WOODLANDS presents a truly exceptional private estate in one of Caledon's most coveted locations.

4780 Escarpment Side Road, Caledon

$1,399,900
6 Beds 4 Baths W13570778 MLS
Pride of ownership shines throughout this updated, custom-built Grand Brook home offering ~2,400 sq.ft. above grade. Situated on a premium, landscaped oversized pie-shaped lot with an impressive 100-ft frontage, this property features a extra wide driveway with 7 car parking space. Over $100k has been invested in a spectacular private backyard oasis with professional landscaping; a swimming pool ;a custom cabana complete with a TV & wet bar; a large retractable awning-perfect for outdoor entertaining/family gatherings. The interior is recently renovated with quality and tasteful upgrades. The chef's kitchen features quartz countertops, solid hardwood cabinetry, a designer pantry, porcelain flooring, and a spacious eat-in area overlooking the pool through new patio doors. The adjoining family room overlooks the kitchen and offers a cozy fireplace, hardwood flooring, automated power blinds, and an inviting atmosphere. The impressive 17-ft grand foyer welcomes guests with a grand, wainscoted wall staircase, stunning light fixture, extensive pot lighting, and an oversized front hall guest closet. The combined living/dining room features a beautiful new double door entry and gleaming new hardwood floors. The main floor features an upgraded 2-piece powder room and a laundry room with a window, closet, and convenient access to a heated oversized double garage. California shutters throughout add elegance and privacy. The second floor offers 4 generously sized bedrooms with large closets and parquet flooring. The spacious primary bedroom features a walk-in closet and a luxurious, fully updated ensuite complete with a soaker tub and heated floors. The finished basement provides exceptional versatility and can serve as an in-law suite, featuring a full kitchen, full bathroom, 2 additional rooms, and a cantina. This meticulously maintained home combines exceptional craftsmanship, quality upgrades, and outstanding indoor/outdoor living in a highly sought-after neighbourhood.

22 Ashbury Crescent, Caledon

$1,275,000
6 Beds 3 Baths W13569692 MLS
Beautifully Updated South Hill Family Home Offering Over 3,800 sq. ft. of Living Space on a Spectacular Pie-Shaped Lot. With Approximately 2,543 sq. ft. Above Grade plus a 1,272 sq. ft. Lower Level Waiting for Your Finishing Touches with 2 Bedrooms Completed. This Home Combines Generous Living Space with Exceptional Outdoor Potential. Set on an Impressive Lot Measuring 18.07' x 179.57' x 30.16' x 211.60' x 74.16', the Expansive Backyard is a Rare Find, Offering Outstanding Privacy and Endless Possibilities, Including Plenty of Room for a Pool, Play Area, or Future Outdoor Retreat or all Three. Designed for Both Everyday Family Living and Entertaining, the Backyard Features a Beautiful 12' x 16' Deck with an 11' Retractable Awning, Creating the Perfect Outdoor Gathering Space. Inside, the Updated Kitchen Serves as the Heart of the Home, Featuring Granite Countertops, Stainless Steel Appliances, and a Spacious Breakfast Area Located Beside the Dining Room with Built in Custom Buffet.The Thoughtfully Designed Floor Plan Offers Four Generously Sized Bedrooms, Including a Spacious Primary Suite with a New Walk in Closet. Additional Highlights include a Welcoming Front Foyer, Patterned Concrete Front Walkway and Porch, and a Convenient Lower-Level Laundry Room. Major Updates Include Updated Kitchen, Front Door (2022), All Windows (2021), Eaves and Eavestroughs (2022), Furnace (2022), Garage Door (2022), Deckboards and Stairs (2026). Move-in Ready and Ideally Located in the Sought-After South Hill Neighbourhood of Bolton, this Exceptional Home Offers the Perfect Combination of Space, Quality Updates, and an Incredible Backyard for Today's Growing Family.

32 Coolspring Crescent, Caledon

$3,299,999
7 Beds 6 Baths W13569080 MLS
Introducing a residence of unrivaled grandeur, where architectural brilliance meets timeless sophistication. Set behind a picturesque winding driveway on 10+ pristine acres of professionally landscaped grounds, this extraordinary custom estate offers over 7500 sqft of exquisitely curated living space, masterfully designed for those who appreciate uncompromising luxury. Every room is a showcase of exceptional craftsmanship, from soaring vaulted ceilings and intricate hand-carved architectural details to bespoke finishes that define elegance at every turn. The spectacular formal dining room comfortably hosts 20+ guests beneath a magnificent hand-carved ceiling, while the chef-inspired gourmet kitchen features illuminated back-lit stone countertops, premium appliances, and a stunning fireplace that creates the perfect gathering space. Designed to impress, the home offers Gated Driveway ,5 luxurious bedrooms, an executive office,2 gourmet kitchens, multiple private parking', and a breathtaking hand-carved oak staircase that serves as the architectural centerpiece of the residence. The spectacular resort-inspired solarium provides the ultimate wellness retreat with a sauna and a hot tub, offering year-round relaxation in complete privacy. An exceptional private in-law suite includes 2 additional bedrooms, a full bathroom, kitchen, and spacious living room, making it ideal for extended family, guests, or multi-generational living. Every window captures breathtaking views of rolling lawns, mature trees, and meticulously landscaped gardens, creating a peaceful sanctuary unlike any other. The expansive grounds provide endless possibilities for entertaining, recreation, or simply enjoying the serenity and exclusivity of country estate living. This remarkable multigenerational property seamlessly blends elite craftsmanship, timeless elegance, and resort-style luxury, creating a residence that is as functional as it is a legacy estate. 3 kitchens.

1 Flaherty Lane, Caledon

$6,399,000
6 Beds 10 Baths W13565682 MLS
Welcome to 9 Flaherty Lane, a breathtaking custom estate nestled on over 10.6 acres in one of Caledon's prestigious enclaves and backing onto 50 acres of conservation land. Spanning over 13,500 square feet above grade and over 20,000 square feet total, this residence offers homeowners unmatched luxury, privacy, and scale. Inside, 5 prodigious bedrooms reside, each with its own ensuites, including a mesmerizing Owners' suite with his and her ensuites and a private guest bedroom in the lower level. Soaring ceiling heights are found across all 3 levels and range from 10 ft to 21ft, with 3 open to the above living areas. Both warm and inviting, this home attracts an abundance of natural light via the bespoke solarium and sunroom. As you make your way through this lovely home, signature features are found, including a 2-level mahogany library with an enchanting spiral staircase, a home theatre, a retro 50's inspired diner, a 5-car garage, multiple fireplaces, 9 geothermal heating and cooling systems, and a gourmet kitchen with a 60" Wolf gas cooktop and oven. Winning "North America's Best Pool" award in 1997, the indoor pool is truly a space where loved ones can gather and enjoy all year round. The serene outdoors offers just as much as the inside, with a spring fed 1 acre pond, a gazebo, a large designer patio with custom railing overlooking the water, and ample green space to host large social gatherings. This home is an absolute must see and offers a rare high-capacity well pumping 120 liters of water per minute, as well as an oversized septic tank and a new roof completed in 2024. With 16 interior and exterior cameras operated through Telus, security here is top-tier! Built to the highest standards using custom-made materials, this estate offers a rare blend of elegance and resort-style living. Whether hosting on a grand scale or seeking a private retreat, 9 Flaherty Lane delivers an extraordinary lifestyle!

9 Flaherty Lane, Caledon

$4,999,999
6 Beds 6 Baths W13504950 MLS
Welcome to 3722 The Grange Side Road, an exceptional 84-acre country estate offering a rare blend of privacy, natural beauty, and outstanding versatility. A long, tree-lined driveway winds through picturesque farmland, leading to an impressive natural stone bungalow perfectly positioned to capture sweeping rural views. The property comprises approximately 84 acres, including about 55 workable acres of gently rolling land, complemented by a tranquil pond near the entrance. This setting is ideal for agriculture, a home-based business, or multigenerational living. The main residence showcases quality craftsmanship with spacious, well-appointed interiors and a flexible layout offering three potential living areas, making it well suited for extended family arrangements or adaptable use. A standout feature is the detached stone-fronted, steel-clad workshop/garage, complete with three oversized 12-foot bay doors, a full four-piece bathroom, and an expansive 2,200 sq ft upper-level loft featuring three additional bedrooms and two bathrooms. An additional steel garage with four oversized doors and a secondary workshop/shed further enhance the property's functionality. Whether you are an entrepreneur seeking space for a business, a hobbyist requiring ample storage, or a family looking for room to grow, this estate offers unmatched flexibility. The land presents endless opportunities for farming, recreation, or future expansion. Set in a peaceful rural location while remaining within a convenient drive to nearby towns and amenities, this is a truly signature property that seamlessly combines natural beauty with practical, adaptable living.

3722 The Grange Side Road, Caledon

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