Caledon Real Estate | Caledon Homes with a Pool for Sale

Private 24.9 acres across from the Paintbrush Golf Course, positioned high on Caledon's Escarpment, this custom, architect-designed 4+1 bed, 2.5 bath has beautiful curb appeal on a park-like, idyllic setting and features country views from every window, sun all day in the south-facing backyard & in-ground pool, rolling hiking trails w/ nature in abundance (turkey, deer, songbirds), and Toronto city skyline views beyond the mature trees. The main level features oak-pegged flooring & crown moulding. Living w/ French doors & wood-burning fireplace framed w/ a pine hearth & surround. Bright & spacious two-toned Kitchen is warm & inviting, w/ granite c-tops, travertine b/splash, center island w/ b-bar is open to the Family w/ a propane gas fireplace, south-facing views, and a sliding-door walk-out to the pro-landscaped pool & patio area. The Primary features an elegant 5-piece ensuite w/ pocket door, skylights, in-floor heating, a glass shower, bidet, soaker tub & long country views. If you look closely, you may even spot the CN Tower through the trees in the distance! Bedrooms 2, 3 and 4 have closets, enjoy beautiful views & share a 4-piece bathroom w/ skylights. Bedroom 5 is in the partially fin bsmt. A Breezeway/Mud rm offers additional access to the home & backyard. It leads to an unfin/uninsulated rm w/ garage access, with potential for workshop, gym, storage or bonus rm! Daikin Heat pump (2020). Enjoy local quaint restaurants, arts centers, craft breweries, farmer's markets, coffee shops, nearby conservation areas, the Caledon Trailway, the Bruce Trail (across the street!), and the Caledon Ski Club. For golf enthusiasts, this property is steps to the Paintbrush, 10 mins to the Pulpit Club, and is 20 minutes to the TPC Toronto at Osprey Valley. There is paved road access to major arteries for ease in commuting to the city or to the north. Enjoy being a 5-min drive to Caledon East, 20 mins to Orangeville & a 1-hour drive to TO. A wonderful central location!

4845 Escarpment Side Road, Caledon

$1,329,900

4 Beds ⋅ 3 Baths ⋅ W13763252 MLS

Welcome to this masterfully designed property in the heart of Palgrave, where timeless character meets uncompromising modern luxury. Enjoy absolute maintenance free comfort from the fresh stucco exterior & steel roof to the heated, patterned-concrete driveway, walkways & patios & a lush front lawn, putting green, & low-maintenance artificial turf, plus electronic entry gate with parking for 10-12 vehicles. Step through the substantial solid entry door into this beautiful 3+1 bedroom home, a warm, open-concept main floor washed in hardwood flooring. A custom chef's kitchen anchors the space with granite counters, stainless appliances, a gas range & a separate island. The dining area flows to the backyard oasis, while the main-floor family room and custom 3-piece bath open through custom sliding glass fully opening doors lead onto your private outdoor retreat. Upstairs, a charming primary suite with spa-inspired ensuite, two additional bedrooms, and a second 3-piece bath, plus laundry. Each bedroom with independent comfort thanks to a dedicated heat pump. A fully finished basement with private entry walk-up boasts a great room, bedroom and functional mechanical room all offering valuable additional living space. Outside is where this property truly shines: a fully fenced large private yard centred on a saltwater, cement in-ground pool with waterfall feature, artistic concrete, and turf surrounds, a gazebo bar with swings, and awnings for shaded lounging. A heated, insulated double garage/shop with loft storage, reached by an industrial folding staircase, houses the pool's mechanical systems and heating for the patterned concrete, all offers a rare workshop or storage solution. Complete with a whole home Generac Generator and Ubiquity security cameras, a Tesla EV charger & so much more. Just steps to Palgrave's charming main street, the Caledon Trailway, Palgrave pond & the tennis club.This is an extraordinary opportunity with bespoke customization at every turn!

19 Birch Avenue, Caledon

$2,299,999

4 Beds ⋅ 5 Baths ⋅ W13762806 MLS

A masterfully designed turnkey estate in prestigious Palgrave, this exceptional residence embodies timeless elegance and uncompromising luxury while offering the perfect balance of peaceful estate living just a short drive from the city. Showcasing thousands invested in premium interior finishes and professional landscaping, this is a true turnkey property where every detail has been thoughtfully curated. From the chef-inspired kitchen appointed with Wolf and Sub-Zero appliances to the soaring 10-foot ceilings, extra-height basement, exquisite coffered ceilings, and custom wainscoting throughout, every space exudes quality and sophistication. Designed to accommodate refined entertaining and multi generational living, the home features two designer kitchens and two full laundry rooms. Outside, a private resort inspired oasis awaits with a saltwater pool, a spectacular glass-enclosed pavilion with folding doors and windows, an outdoor bar and bathroom, elegant interlock walkways, a flagstone front porch, professionally landscaped grounds with a full irrigation system, and an impressive circular driveway that creates a grand arrival. Complete with a whole-home backup generator and water softener, this exceptional estate is truly move in ready simply collect the keys and begin enjoying the luxury lifestyle you've been waiting for. As an added bonus, enjoy peace of mind with a complimentary 1-Year Home Warranty covering all household appliances.**Terms and conditions apply.

13 Doctor Reynar Road, Caledon

$1,199,000

4 Beds ⋅ 2 Baths ⋅ W13758914 MLS

Welcome to Hilltop Drive. One of Caledon East's most desirable communities. This beautifully updated 4-level side-split offers the ideal blend of modern style, space, and functionality. Featuring four bedrooms and four distinct living levels, this home has been thoughtfully designed to accommodate every stage of family life. At the heart of the home is the stunning renovated kitchen, showcasing an impressive 5' x 9' island, modern cabinetry, stainless appliances, a temperature-controlled wine fridge, abundant storage, and stylish finishes throughout. The adjoining family room is bright and inviting, complete with a walk-out to the patio that seamlessly blends indoor and outdoor living. The upper-level features three spacious bedrooms and a beautifully renovated 4-piece bathroom. On the lower level, you'll find an additional family room with a second walk-out to the yard, a renovated 3-piece bathroom, a fourth bedroom, and a generous laundry room, offering the perfect setup for growing families, multi-generational living, or welcoming overnight guests. The finished fourth lower level provides even more versatile space, with another cozy family room, a beautiful wet bar and seating area, and an abundance of storage space. Summers just got better as you enjoy your own private backyard oasis, surrounded by mature trees, extensive stonework, large garden shed, exceptional privacy, and a beautiful saltwater pool - the perfect setting for entertaining family and friends. Don't miss this incredible opportunity to call this exceptional Caledon East property your forever home!

25 Hilltop Drive, Caledon

$5,995,000

5 Beds ⋅ 5 Baths ⋅ W13756116 MLS

Discover That Form A Private Paradise, This Stunning Property Boasts Over 10,000 Square Feet Of Gorgeous Living Space On Almost 25 Acres Of Prime Land. Lovingly Cared For And Kept in Perfect Shape, This One-Of-A-Kind Home Mixes Classic Charm With Timeless Beauty. Step Inside To Enjoy Top-Notch Woodwork, Warm Solid Walnut And Cherry, And High Ceilings That Make Every Moment Feel Magical. Huge Floor-To-Ceiling Windows Fill The Rooms With Sunshine, Smoothly Leading Out To A Massive Terrace From The Main Bedroom, Living Area, Dining Space, And Prep Kitchen. Treat Yourself To The Pro Chef's Kitchen, Complete With A Classic Pizza Oven Ready To Impress Your Friends And Fire Up Amazing Meals. A Whole Floor Built For Fun And Games, Flowing Right Into A Backyard Oasis Like Your Own Private Resort, Full Of Endless Chill Vibes And Joy. The Smart Design Keeps Everything Flowing Easily, Plus There's A Separate Workshop And Lush Garden. Drive Through The Grand Gates, And Those Tall Trees Welcome You With A Peaceful Hug That You'll Never Forget. This Isn't Just A House It's A Smart Investment And The Ultimate Blend Of Cozy Indoor Luxury And Dreamy Outdoor Living. Grab This Once-in-A-Lifetime Chance To Dive Into Pure Bliss Book Your Private Showing Today And Walk Into A World Of Total Wow!

18387 The Gore Road, Caledon

$1,399,900

4 Beds ⋅ 4 Baths ⋅ W13755670 MLS

Rarely does a property of this calibre become available, where traditional elegance and contemporary design come together so beautifully. Filled with natural light and timeless charm, this impeccably maintained detached brick home is nestled on a quiet cul-de-sac in the highly sought-after Bolton community.Strawberry Hill Court is regarded as one of Bolton's most desirable streets, surrounded by nature, ravines, scenic trails, and an abundance of tranquility. Offering approximately 4,200 sq. ft. of living space, this exceptional family home features four generously sized bedrooms and an inviting, thoughtfully designed layout.The main floor showcases 9-ft ceilings and a bright, open-concept design ideal for both everyday family living and entertaining. Enjoy breathtaking views of the picturesque backyard from the sun deck, complete with mature trees and spectacular sunsets.Step outside to your own private backyard oasis, featuring an inground saltwater pool, outdoor bar, gas fire pit, and beautifully finished patterned concrete. Professional landscaping throughout the exterior enhances the home's exceptional curb appeal and creates a resort-like setting.Conveniently located close to schools, parks, shopping, dining, and entertainment, with the 427 extension approximately 15 minutes away. A rare opportunity to own a beautifully appointed home in one of Bolton's most desirable locations.A truly exceptional family home designed to be enjoyed for years to come. Don't miss this opportunity!

43 Strawberry Hill Court, Caledon

$5,250,000

5 Beds ⋅ 7 Baths ⋅ W13744042 MLS

A rare offering in Caledon Mountain Estates on 2.8 acres, this newly built contemporary estate pairs exceptional scale and sophisticated design with a level of privacy that is increasingly difficult to find-all within convenient reach of the GTA. Set against a peaceful natural landscape, the approximately 9,137 sq. ft. residence is designed to feel both dramatic and deeply livable, with expansive windows, refined finishes and seamless connections to the outdoors.Created equally for everyday family living and effortless entertaining, the home's impressive great room is anchored by a striking 23-ft. microcement fireplace and surrounded by expansive windows overlooking the natural landscape. At the heart of the home are two beautifully appointed kitchens, including a discreet spice kitchen finished to the same exacting standard and featuring its own separate entrance.The private primary wing feels like a retreat unto itself, complete with a walk-in closet with laundry, wet bar and luxurious 5-piece ensuite. A laundry room on each level adds exceptional convenience to the thoughtfully designed floor plan.Wellness and entertainment are equally well considered, with a dedicated gym, indoor sauna and separate lounge/party room complete with fireplace. The gym and sauna lead directly to the outdoors where there is a covered outdoor kitchen and entertaining area, putting green and pool.Outside, the property transforms into a private, resort-inspired escape. Surrounded by a mature natural landscape, the backyard features an oversized swimming pool with a padded tanning ledge, automatic cover, deck jets and Omni smart system. Further enhancing the ownership experience, the home includes two years of builder-backed ownership support, offering added confidence and continuity well beyond closing. An exceptional Caledon estate for those who value substantial living space, striking contemporary architecture and an extraordinary connection to nature.

7 Maple Meadow Court, Caledon

$1,999,000

3 Beds ⋅ 5 Baths ⋅ W13736076 MLS

Welcome to 35 Brawton Drive, an impressive family residence situated in the highly desirable community of Palgrave, Caledon. Offering outstanding curb appeal, this substantial brick home is complemented by a beautifully maintained property, mature surroundings, a large paved driveway, attached double-car garage and an inviting covered front porch. 3 Bedrooms. 5 Washrooms, Large double garage, Step outside and discover your own private backyard oasis, highlighted by a large inground swimming pool with slide, expansive poolside patio, attractive interlocking stonework and beautifully manicured lawns. The thoughtfully designed outdoor space provides an exceptional setting for entertaining family and friends, summer barbecues or simply relaxing poolside in the privacy of your own backyard. The home's impressive exterior, generous proportions and established landscaping create a wonderful combination of traditional character and comfortable family living. Multiple walkouts provide a natural connection between the home and the outdoor entertaining areas, while the spacious yard offers plenty of room beyond the pool for children, pets and recreation. Located in Palgrave, one of Caledon's most sought-after communities, This property offers the peaceful atmosphere and natural beauty the area is known for while remaining conveniently connected to surrounding amenities. A wonderful opportunity to own a spacious palgrave home with excellent curb appeal, a double garage and a spectacular resort-inspired backyard - perfect for families who love to entertain and enjoy outdoor living.

35 Brawton Drive, Caledon

$1,259,000

4 Beds ⋅ 4 Baths ⋅ W13732340 MLS

Welcome to 23 Deer Valley Drive, a beautifully maintained all brick family home set on a premium 142 foot deep lot in one of Bolton's most established family neighbourhoods. Lovingly cared for by its original owners, this home has been the backdrop for years of family memories and is ready to welcome its next chapter. Pride of ownership is evident throughout, thoughtfully updated over the years. The main floor offers a functional layout with a spacious formal living room, separate dining room, and a warm family room with a wood burning fireplace overlooking the backyard. The bright eat in kitchen features a breakfast area with a walkout to the patio. Direct access from the garage into the laundry and mudroom adds everyday convenience. Upstairs you will find four generous bedrooms, including a spacious primary retreat with a large walk in closet, private ensuite, and peaceful views overlooking the backyard and Foundry Park. Two full bathrooms on the upper level provide plenty of space for a growing family. The finished basement offers incredible flexibility with a large recreation room, bar area, additional sitting room with a bio flame fireplace, a bathroom, workshop, cold room, and plenty of storage. The backyard is designed for making memories, complete with a solar heated saltwater in-ground pool, stamped concrete patio, mature landscaping, and open views of the park behind. Whether you are hosting family and friends or enjoying a quiet evening at home, this is a space you will appreciate all summer long. This home has been meticulously maintained and thoughtfully improved over the years. Located close to excellent schools, parks, trails, recreation, shopping, restaurants, and all the amenities that make Bolton such a wonderful place to call home, this is a rare opportunity to own a home that has been truly loved and exceptionally cared for.

23 Deer Valley Drive, Caledon

$1,689,000

5 Beds ⋅ 4 Baths ⋅ W13731986 MLS

Welcome to this spectacular executive retreat in the prestigious Tamarac Estates of Caledon, where luxury, privacy and lifestyle come together on over 2 beautifully landscaped acres. Surrounded by a mature treed perimeter and designed for those who love to entertain on a grand scale, this stately bungalow offers the exact formula to create the perfect getaway: over 5,000 sq. ft. of finished living space, a 3-car garage, with ample parking and a backyard to die for! Inside, the free-flowing open-concept layout is bright, spacious and inviting. The eat-in kitchen features built-in appliances, a gas range and walkout to the raised multi-level deck-perfect for summer gatherings overlooking the hot tub and heated saltwater pool. The kitchen opens seamlessly to the dramatic vaulted living room, where the fireplace and large windows afford abundant natural light create an impressive & welcoming atmosphere. The luxurious primary suite is privately positioned in its own wing of the home and features a spa-inspired 5-piece ensuite, offering a true retreat away from the additional bedrooms and main-floor office. The fully finished walk-up lower level provides outstanding flexibility, with a separate entry from the garage, 2 bedrooms with potential for a third, a 4-piece bathroom and expansive bright living areas. Ideal for extended family, a secondary living arrangement, theatre room, games room or future kitchen-the possibilities are exceptional. With amenities like natural gas, high-speed internet and convenient access to Orangeville shopping and amenities, this remarkable property delivers the space, privacy and lifestyle of country living without sacrificing modern convenience. A true luxury retreat made for living, entertaining and enjoying a slower pace.

14 Briarwood Drive, Caledon

$1,599,000

5 Beds ⋅ 4 Baths ⋅ W13726484 MLS

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 Macville Public School boundary. This is upgraded house- includes New Full house waterproofing (2026), New Clothes Dryer and Washer (2026), Sediment Filter (2026) , New Reverse osmosis (RO) system (2026), new well pressure tank with brass T (2026), 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). Some photos virtually staged

14812 Centreville Creek Road, Caledon

$2,250,000

4 Beds ⋅ 4 Baths ⋅ W13722256 MLS

Luxurious Caledon escape awaits in this executive home. Refined country living meets exceptional convenience. Set on2beautifully groomed acres with private pond, this expansive, lovingly maintained bungalow offers an extraordinary lifestyle so close to the city. From the moment you arrive, the setting is impressive, yet it is what's inside that truly sets this home apart. With over 7,500sf of bright, stunning space, this remarkable residence features 4 king-sized bdrms, 3.5 marble & stone baths, indoor heated pool, sun-filled gym/yoga room, &floor-to-ceiling windows showcasing sweeping views of the lush grounds & 2 stone patios.Designed for both effortless living & unforgettable entertaining.The main floor offers one-level living, private office, double-sided fireplaces,2 formal living spaces one includes an impressive20' cathedral ceiling ideal for billiards, entertaining, or enjoying the grandeur of the space.The expansive kitchen is equally impressive, with granite countertops,raised bar,48"stainless fridge/freezer,double wall ovens,&walk-in pantry,all open to a generous breakfast area&peaceful solarium overlooking the tranquil landscape. Truly fit for a King!Adding to the property's extraordinary story, the Duke of Kent, Queen Elizabeth II's cousin, once called this estate home during a stay in the 1990s,reportedly enjoying breakfast&afternoon tea daily in the home's gorgeous solariums.Approached by an oversized stone driveway with ample parking,the property offers 3-car garage&convenient mudroom separate from the main-floor laundry.Imagine the freedom of having your own private retreat to swim/exercise/entertain/unwind year-round, even skate/hockey in winter without memberships,commuting,or giving up GTA amenities. Inglewood offers the best of both worlds:Peaceful rural setting,yet connected to Orangeville, Brampton & Hwy 410. A truly remarkable property!An unforgettable setting!A home with a story to tell!Come experience it. You have to see it to believe it!

4 Ingleview Drive, Caledon

$1,069,900

3 Beds ⋅ 4 Baths ⋅ W13720404 MLS

Beautiful 3-Bedroom Home In A Brand-New Subdivision! Welcome To This Stunning Property Featuring A Legal Basement With Kitchen, Bedroom & Separate Entrance With Exceptional Finishings. The upgraded kitchen offers an extra-large island, tall upper cabinets with crown molding, Under-Cabinet Lighting, Premium Stainless-Steel Appliances, And A Spacious Pantry. [The Bright, Open-Concept Living And Dining Area Boasts Upgraded Hardwood Floors, 9-Ft Ceilings, And A Functional Layout With No Wasted Space. The Second Floor Includes Three Generously Sized Bedrooms, A Convenient Laundry Room, And Upgraded Carpeting. The Home Also Features Quality Blinds And Fresh Paint Throughout. Relax On The Front Porch And Enjoy Beautiful Summer Sunsets With Family - The Perfect Spot To Unwind At The End Of The Day. Conveniently Located Just Minutes From Fwy 410, Mount Pleasant GO Station, Future Hwy 413, Future [Elementary School, And All Amenities.

29 Lippa Drive, Caledon

$1,399,000

4 Beds ⋅ 3 Baths ⋅ W13719478 MLS

Stunning Family Home in Desirable Bolton North - Welcome to this exceptional detached home in the highly sought-after community of Bolton North. Lovingly cared for by its original owner, this residence showcases true pride of ownership and has been meticulously maintained inside and out. Nestled on a quiet, family-friendly street, you'll enjoy the perfect balance of peaceful living and convenience, with parks, walking trails, schools, and everyday amenities just moments away. Offering four generously sized bedrooms, this home is designed for growing families. Large windows throughout fill the space with natural light, while the spacious primary retreat features a large ensuite bathroom, creating the perfect place to unwind. The main level boasts elegant hardwood flooring and a stunning modern staircase that serves as a beautiful focal point. At the heart of the home is the beautifully renovated kitchen, complete with a spectacular 6-foot island featuring a striking stone waterfall countertop. Perfect for entertaining and everyday living, this space is designed to bring family and friends together. Enjoy extra living space in the finished basement, offering endless possibilities for a recreation room, home office, gym, or family gathering area. Step outside to your beautifully landscaped backyard, where summer memories await. Relax, entertain, and enjoy the impressive 16' x 31' inground pool, offering the ultimate private retreat for family and friends. This is a rare opportunity to own a truly cherished home in one of Bolton's most desirable neighbourhoods-a property that has been exceptionally cared for and is ready for its next chapter.

18 Mccabe Crescent, 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

$969,900

4 Beds ⋅ 3 Baths ⋅ W13713240 MLS

Tucked away on a quiet court in Bolton's highly desirable North Hill community, this beautifully renovated 4 bedrooms home sits on an impressive oversized lot, offering the perfect balance of privacy, style, and functionality. Thoughtfully redesigned with warm wood finishes and rustic-inspired details, the home exudes character and timeless charm. The open-concept main level is designed to impress, featuring a stunning chef's kitchen complete with a large centre island, custom cabinetry, and a spacious dining area. The expansive, professionally landscaped backyard is a true private retreat, uniquely tiered across three levels to maximize both space and privacy. Enjoy summer days by the in-ground pool, relax beneath the covered patio, or entertain family and friends in this peaceful outdoor oasis. The finished lower level offers exceptional versatility, providing the ideal space for a recreation room, games room, home theatre, fitness area, or additional guest accommodations. A double attached garage and an oversized driveway with parking for up to ten vehicles add outstanding convenience for families and guests alike. Offering a rare combination of refined rustic elegance, generous indoor and outdoor living spaces, and an unbeatable setting in one of Bolton's most coveted neighbourhoods, this exceptional property is a place you'll be proud to call home.

67 Sherin Court, Caledon

$1,550,000

5 Beds ⋅ 5 Baths ⋅ W13701870 MLS

Location! Location! Location! Welcome to this stunning, fully upgraded 4-bedroom detached home in the highly sought-after SouthFields Village community of Caledon. Featuring an impressive layout with separate living and dining rooms, a soaring open-to-above family room with fireplace, and a versatile main-floor den/office. Enjoy high ceilings, tasteful upgrades throughout, and an exceptional backyard oasis complete with a pool and waterfall-perfect for entertaining and summer enjoyment. The extended driveway provides ample parking. The Finished basement features a separate entrance, 1 bedroom, kitchen, and washroom, plus an additional room/rec room that can be enjoyed by the owners or potentially used as an additional bedroom. Excellent location with easy access to Hwy 410, and close to schools, community centres, parks, plazas, and numerous amenities. A wonderful opportunity to own a move-in-ready home in one of Caledon's most desirable communities!

51 Learmont Avenue, Caledon

$1,675,000

4 Beds ⋅ 5 Baths ⋅ W13700374 MLS

Welcome home to 28 Billy Court, a spectacular luxury residence in Caledon East, nestled in a family-friendly neighbourhood and showcasing stunning high-end finishes, an impressive layout and a breathtaking 202-ft-deep lot with a resort-inspired backyard. Soaring 11.8-ft ceiling in the grand foyer, 9-ft ceilings throughout the main level, elegant trims and baseboards, expansive windows and abundant natural light. Private home office, formal living and dining rooms ideal for entertaining. Chef's dream kitchen featuring premium Viking appliances, double wall ovens, 6-burner gas range with pot filler, integrated fridge, quartz counters, undermount double sink, oversized breakfast bar with sink, contemporary backsplash and modern window coverings. Open-concept breakfast area with walk-out to the spectacular backyard. Family room overlooks the pool and features a stunning feature-wall gas fireplace. An entertainer's dream outdoor oasis with inground pool, pool lounge, BBQ area and fire pit. Full-size soundproof cabana with separate electrical panel, hot water tank, wet bar, 2-piece washroom and outdoor shower, with potential for garden suite, subject to approvals. Garden shed with pool equipment and front & rear irrigation. Main-level laundry/mudroom with side-yard access and direct entry to the 3-car garage. Luxurious primary retreat with his-and-hers walk-in closets and spa-inspired 5-piece ensuite featuring massive soaker tub and standalone shower. Two additional bedrooms share a 4-piece semi-ensuite with separate vanities. Fourth bedroom offers a private 4-piece ensuite, ideal for nanny, in-law or guest suite. Expansive unfinished lower level offers approximately 1,682 sq. ft. of additional potential living space, with potential for separate entrance, subject to approvals. Ideally located near parks, schools, Caledon Trailway and Caledon East Community Complex, this exceptional home offers the perfect blend of luxury, privacy, recreation and family-friendly living.

28 Billy Court, Caledon

$1,359,000

5 Beds ⋅ 2 Baths ⋅ W13699698 MLS

Welcome to this beautifully and extensively renovated bungalow situated in the desirable, family-friendly community of Caledon Village. Thoughtfully updated throughout, renovations include new windows, flooring, doors, appliances, and much more, creating a stylish, move-in-ready home with modern finishes and a functional, carpet-free layout. The bright and spacious living room showcases an impressive custom-built media wall with integrated LED lighting and a cozy fireplace, creating an inviting space for both everyday living and entertaining. The beautifully updated kitchen features quartz countertops and porcelain tile flooring, offering an attractive combination of contemporary design and functionality. A generous family room provides additional living and entertaining space and features its own fireplace, separate front entrance, and walk-out to the backyard, adding excellent versatility to the home's layout. The finished basement significantly expands the available living space and includes two additional bedrooms and a wet bar, making it ideal for extended family, overnight guests, a recreation area, home office, or additional entertainment space.Step outside to an entertainer's dream backyard. The large, fully fenced property features a beautiful inground saltwater pool, providing the perfect setting for summer gatherings, relaxing poolside, and enjoying the outdoors. The welcoming front porch/deck is finished with modern glass railings, further enhancing the home's attractive curb appeal, while the spacious driveway provides ample parking for family and guests.Ideally located close to parks, schools, shopping, recreation, and everyday amenities, with convenient access to Highway 10, this exceptional property combines modern renovations, generous living space, a private backyard retreat, and an excellent Caledon Village location.A wonderful opportunity to own a turnkey home offering comfort, style, versatility, and outstanding indoor and outdoor living space.

6 Maple Grove Road, Caledon

$1,179,000

4 Beds ⋅ 4 Baths ⋅ W13696312 MLS

This bungalow offers over 3,300 sq. ft. of finished living space with a separate entrance, making it ideal for multi-generational living or income potential. Located on a quiet cul-de-sac in a family-friendly neighbourhood, the private backyard overlooks a parkette and features a saltwater pool with slide, spa/hot tub, gazebo, mature trees, and wrought iron gate access on both sides.The open-concept main floor features spacious living and dining areas, a large kitchen, a family room with a three-sided fireplace, and a walkout to an expansive deck overlooking the backyard.The spacious primary suite includes a beautifully updated ensuite with heated floors and a walk-in closet. Two additional bedrooms, a full bath, main-floor laundry, and direct garage access complete the main level.The bright above-grade walkout lower level offers a second kitchen, generous living and dining areas, a private bedroom with ensuite, French doors, a separate entrance, and a laundry rough-in.A rare opportunity to own a spacious home with flexible living space, exceptional outdoor amenities, and a prime location in one of Valleywood's most desirable neighbourhoods.

8 Vista View Court, Caledon

$1,939,900

4 Beds ⋅ 3 Baths ⋅ W13686572 MLS

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.

4 Wolf Crescent, Caledon

$1,849,900

5 Beds ⋅ 3 Baths ⋅ W13665840 MLS

Set on a spectacular and private 1-acre lot surrounded by rolling hills and mature greenery, this exceptional country property offers the perfect blend of luxury, comfort, and versatility. Featuring 4+1 bedrooms and 3 bathrooms, this beautifully finished home showcases an open-concept design with quality craftsmanship throughout. Bright, expansive living spaces are enhanced by large windows that capture breathtaking countryside views, while a stunning vaulted beam ceiling adds warmth, character, and a true sense of grandeur. The chef-inspired kitchen is designed for both everyday living and entertaining, featuring a centre island with sink, stainless steel appliances, built-in wall ovens, and induction cooktop. The elegant living room boasts bamboo hardwood flooring and a cozy wood-burning fireplace, complemented by a formal dining room and spacious family room. Step outside to a remarkable three-season covered porch overlooking your private backyard oasis, complete with an inground saltwater pool, hot tub, and beautifully landscaped grounds-perfect for relaxing or entertaining family and friends. Adding exceptional value, the fully self-contained in-law suite offers endless possibilities for multi-generational living, extended family, guests, or potential rental income. The main level is completed by two generous bedrooms and a beautifully appointed bathroom. Upstairs, you'll find the luxurious primary suite, an additional bedroom, and a spa-inspired 5-piece bathroom designed as the perfect retreat. Set in a peaceful country setting yet conveniently located within easy reach of nearby amenities, this one-of-a-kind property delivers the privacy, space, and lifestyle you've been searching for. Floor Plans Attached. Please note that some inside pictures have been virtually staged.

4314 Beech Grove Side Road, Caledon

$899,000

3 Beds ⋅ 3 Baths ⋅ W13658350 MLS

Located in the desirable South Hill community of Bolton, welcome to 249 Leavens Court. This beautifully updated home features 3 bedrooms, 3 bathrooms, and a finished basement complete with a Cozy rec with rough ins for future kitchen/laundry room.The open-concept main floor offers a fully updated, generously sized kitchen that flows seamlessly into the expansive family room overlooking the backyard-perfect for both everyday living and entertaining.Situated on an oversized 45' x 124' lot with great patio an above ground pool in a quiet, family-friendly court, this property provides plenty of space for children to play and families to enjoy the outdoors. Conveniently located within walking distance to schools, parks, shopping, and other amenities, plus just a four-minute walk to 24-hour public transit, this home offers an exceptional combination of comfort, space, and convenience.

249 Leavens Court, Caledon

$939,000

3 Beds ⋅ 3 Baths ⋅ W13652306 MLS

Welcome to 28 Crestridge Drive, a beautifully maintained detached home tucked away on a quiet cul-de-sac in one of Bolton's most sought-after neighbourhoods. The landscaped walkway and double car garage set the tone for the pride of ownership found throughout. Step inside to awarm, inviting atmosphere filled with natural light, thanks to generous windows and excellent sun exposure. The open-concept floor plan flows effortlessly, and two natural gas fireplaces,one in the living room, one in the basement, add warmth and character year-round. The updated kitchen features new cabinetry, stainless steel appliances, and a breakfast bar, opening directly to your backyard oasis. The premium ravine lot offers the ultimate privacy with norear neighbours, maintenance-free artificial grass, a jacuzzi, and breathtaking views of nature to enjoy all year long. Three spacious bedrooms include a primary retreat with ample storage and a private ensuite, while the fully finished basement is perfect for a rec room,home office, or family entertainment space, complete with a second gas fireplace. Additional highlights include an EV charging hook-up in the garage, parking for up to 6 vehicles, updated furnace and A/C (2018), garage door (2021), and roof (2016). Minutes from grocery stores,parks, schools, and everyday amenities. A rare opportunity in Bolton!

28 Crestridge Drive, Caledon

$4,750,000

4 Beds ⋅ 5 Baths ⋅ W13646518 MLS

Located in one of the most desirable pockets of Caledon, 446 The Grange Side Road is situated on over 11 acres of wooded grounds and manicured open vistas. This exquisite, private country estate is the perfect blend of country character and contemporary design. Located in close proximity to many clubs and amenities that will appeal to skiers, golfers, cyclists, hikers and equestrians. The house has been thoughtfully designed and features 4 bedrooms and 4.5 bathrooms. An architecturally stunning staircase of steel and glass spans all three floors and allows the natural light to cascade through and into the home while complementing the Norwegian white oak wide plank floors and exposed square log timbers. The interior features over 3,400 square feet of above ground living space with heated floors in the living room, lower level bedroom entrance foyer, and all ensuite baths. There is a state of the art water purification system, 2 gas fireplaces in the living and dining rooms, a Koehler generator, central air conditioning system with two furnaces and humidification systems, extensive Lutron lighting and window blind system, and an electric mosquito shade system enclosing the covered outdoor entertainment area. The outdoor entertaining areas are tranquil and serene, with a covered deck area and three walkouts from main floor principal rooms overlooking the in-ground 16' x 50' heated gunite pool. Views from the pool overlook a spring-fed pond with a waterfall feature, a private meadow attracting flora and fauna, and a private walking trail.

446 The Grange Side Road, Caledon

$1,349,999

3 Beds ⋅ 2 Baths ⋅ W13633632 MLS

One of the nicest homes currently available for sale. This beautifully finished 4-level side split offers comfortable and spacious living from top to bottom. Featuring 3 bedrooms, hardwood flooring, a gorgeous chef's kitchen, an attached double garage plus an additional double garage behind the house, this home is perfect for families or professionals. Situated on a large lot with multiple parking spaces, it also includes an above-ground pool and many upgrades throughout. Located in an ideal Caledon setting with a short drive to major centers, shopping, and amenities. A well-maintained property in a great neighborhood - you won't be disappointed.

40 Victoria Crescent, Caledon

$1,349,900

4 Beds ⋅ 4 Baths ⋅ W13632512 MLS

Welcome To 25 McCandless Court, A Stunning 4-Bedroom, 4-Bathroom Home In One Of Caledon East's Most Sought-After Neighbourhoods. Thoughtfully Designed For Both Functionality And Elegance, This Spacious Property Offers 9-Foot Ceilings, Hardwood Floors, And An Open Concept Main Floor. The Gourmet Kitchen Walks Out To A Fully Fenced, Professionally Landscaped Backyard Oasis Featuring A Heated Inground Pool, Interlock Patio, And Charming Cabana - Perfect For Entertaining Or Relaxing In Total Privacy. Cozy Up By The Fireplace In The Inviting Family Room, Or Work From Home In The Private Main Floor Den. Direct Garage Entry Adds Everyday Convenience. The Primary Suite Is A True Retreat With Two Walk-In Closets And A Spa-Like Ensuite, While Every Additional Bedroom Enjoys Its Own Ensuite Bath. The Finished Basement Expands The Living Space With A Wet Bar, Recreation Area, Second Fireplace, Second Laundry Room, Exercise Room, Cold Cellar, And Rough-In Bath. Extras Include A Water Softener, Reverse Osmosis Water Purifier, Main Floor Laundry, And Ample Storage. Truly Move-In Ready, This Exceptional Home Blends Comfort, Space, And Style In One Of Caledon East's Premier Communities.

25 Mccandless Court, Caledon

$1,357,777

4 Beds ⋅ 4 Baths ⋅ W13617900 MLS

Visit REALTOR website for additional information. This exceptional two-story family home features a stunning backyard pool oasis, a grand circular driveway, in-law suite with its own completely separate entrance. Prime location near a great school. In the heart of Caledon Village, this beautiful 2 storey home sits on a 1.2 acre corner lot, has an attached 2 car garage, large circular driveway for 8 cars, in-law suite with separate entrance through garage, huge yard for kids to play and fenced in patio, pool, cabana and hot tub. This home has 4 bedrooms, 3 1/2 baths, large galley kitchen with quartz countertops, island and SS fridge, gas stove and microwave. Newer baths, hardwood floors throughout, crown moulding, newly painted, professionally finished basement with in-law suite with space for gym or home office. Metal roof with 50 year warranty, brand new furnace and a/c. New insulation, siding & eaves. Walkout to professionally done, two-tone interlock patio with beautiful salt water, gas heated pool, hot tub and fire pit. This is the central gathering spot for family gatherings and relaxation. Whether it's a multi-generational setup, a savvy rental income stream, or your own private retreat, this rare property checks every single box. Close to Caledon Ski Club and Hockley Valley.

12 Meadow Drive, Caledon

$1,629,900

4 Beds ⋅ 4 Baths ⋅ W13617888 MLS

Stunning 3+1 Bed 4 Bath Home On 1.13 Acres In The Village Caledon East. 4443SqFt Of Living Space, 100Ft Wide Lot W/ Mature Trees & Privacy. A 22X32Ft Addition W/ Wrap Around Windows (2016), 16X24Ft Pool W/ Composite Deck "Entertainers Delight W/ Outdoor Tv" (2017), Roof (2019), Furnace (2019), Basement Reno (2019), Bathrooms (2016), Fully Painted (2019), Custom Maple Kitchen (2016), Exotic Brazilian Counter Top (2016), Main Floor Laundry W/ Custom Cabinets (2016), Reverse Osmosis (2026)Water softener (2026,Soffit & Eavestrough (2025, Front Windows (2025), Pool Heater and Filter (2025), One Bedroom In-law Suite w/ Separate Entrance, Kitchen and Large Living Area.

38 Marilyn Street, Caledon

$999,900

4 Beds ⋅ 2 Baths ⋅ W13612054 MLS

Welcome to 1510 Station Road, a beautifully updated home in the heart of Cheltenham, set on a rare 0.344-acre lot (~15,000 sq. ft.) surrounded by gardens, mature landscaping, and outdoor living spaces designed to be enjoyed year-round. Offering updated 4 bedrooms & 2 baths, this home blends historic character with modern comfort. Over $250k has been invested in thoughtful improvements, including a stunning fully renovated Primary Ensuite with walkout access to the gardens, featuring a custom double-sink vanity & freestanding soaker tub. The home also features custom solid wood built-in cabinetry throughout, providing exceptional storage and craftsmanship rarely found. Recent upgrades include a new roof and soffits (2021), updated electrical, plumbing & vapour barrier (2014), and wood siding (2022). The renovated kitchen combines functionality and style with a cathedral ceiling, custom cabinetry, reverse osmosis water filtration, new appliances (fridge, convection oven & microwave - Dec 2025), and a double-drawer dishwasher for added flexibility, savings & convenience when entertaining. Second-floor laundry includes a new stacked washer and dryer (Dec 2025) and a rough-in for a future bathroom. The private retreat gardens feature multiple outdoor spaces including a zen garden, firepit area, gazebo, large back deck, front patio, and an above-ground pool. A former chicken coop offers additional flexibility and potential for conversion into a sauna, studio, or hobby space. The barn and office area is a standout feature, offering extensive storage, two workshops, and a heated office-ideal for entrepreneurs, tradespeople, artists, hobbyists, or anyone working from home. Located within walking distance of parks, trails, river tubing, hiking, cycling, and other outdoor activities, this is a rare opportunity to own a move-in-ready property that offers character, functionality, and a true village lifestyle in one of Caledon's most charming communities.

1510 Station Road, Caledon

$1,499,000

4 Beds ⋅ 3 Baths ⋅ W13606962 MLS

Set on a half-acre lot (100 x 219 ft) along Mississauga Rd between Mayfield and Old School, this two-storey detached home offers 4,250+ sq ft of total living space, 3,000 of it above grade. The main and upper levels were rebuilt in 2011 (plumbing, electrical and HVAC included) and upgraded steadily since. The heart of the home is a large executive kitchen: premium granite counters, wall-to-wallDon't miss this one.custom cabinetry, ceramic tile backsplash, and a breakfast bar. Stainless appliances include a double fridge (2025), two built-in ovens, built-in microwave, 36" gas cooktop and range hood carpet-free interior pairs hardwood in the living areas and bedrooms with ceramic tile in the foyer, kitchen, baths and basement. Pot lights, a natural oak staircase, upgraded baths with premium vanities, and a large multi-functional basement complete the layout. Outside, a driveway that holds 10+ vehicles, an in-ground saltwater pool, a stamped concrete patio, and a detached garage/workshop with hydro and insulation. Mechanicals are a genuine strength: the home is fully spray-foam insulated and runs on a geothermal furnace and A/C that keeps costs low for its size, plus an owned hot water tank, 200-amp service, drilled well with UV and sediment purification, water softener, and updated pump, pressure tank and sump systems. Space, land and unbeatable quality of life on Caledon's southern edge, minutes from Brampton. Don't miss this one.

12806 Mississauga Road, Caledon

$5,499,000

4 Beds ⋅ 4 Baths ⋅ W13601824 MLS

Extraordinary Caledon estate where privacy, a tranquil setting, natural beauty, and endless opportunity come together on approximately 86 spectacular acres. Tucked away among the rolling hills, this remarkable property offers an exceptional blend of open pasture, productive hay fields, mature hardwood forest, scenic trails, and breathtaking countryside views in every direction. The beautiful home is designed to embrace its surroundings, featuring soaring ceilings, expansive windows that flood the interior with natural light and an open-concept layout. The fully finished walkout lower level seamlessly extends your living space outdoors, leading to a resort-inspired backyard complete with a saltwater inground pool, spacious patios, and multiple areas to relax while taking in the peaceful landscape. For those seeking space to work, create, or operate a business from home, the impressive approximately 3,000 sq. ft. heated workshop offers exceptional flexibility with dedicated office space, generous storage, and room for countless uses. The property also features a traditional barn and fenced pasture with convenient livestock watering access, making it well suited for hobby farming, equestrian pursuits, or a variety of agricultural ventures. Whether you're dreaming of a family estate, multi-generational living, a home-based business, hobby farm, or simply investing in one of Caledon's most desirable rural settings, this property offers outstanding potential both today and for the future. Minutes from the amenities of Caledon and within easy commuting distance to Pearson International Airport and the GTA. Enjoy nearby golf courses, equestrian facilities, skiing, cycling, hiking trails, charming restaurants, boutique shopping, and excellent schools-all while coming home to a setting that feels worlds away. A truly rare offering where lifestyle, land, and limitless possibilities meet.

18250 Duffy's Lane, 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

$1,199,000

5 Beds ⋅ 4 Baths ⋅ W13577488 MLS

This two-storey, 4-bedroom, 4-bathroom home with a finished walkout basement is a real crowd-pleaser. Family friendly area. Treed view. Boasting 2,356 sq. ft. plus the finished basement provides over 3000 sq. ft of living space. The main floor is bright and airy with hardwood flooring throughout. Smooth ceilings on the main floor .The family room has a modern two-sided fireplace shared with the spacious dining room, perfect for entertaining. Stylish kitchen with granite counters, stainless steel appliances, a breakfast bar, and a walkout to a deck with breathtaking views. Main floor laundry with access to garage. The primary bedroom fits a king-size bed, includes a lovely sitting area, an updated 5-piece ensuite with a soaker tub, heated floors, glass shower, double sinks, and a walk-in closet. The upper-level is hardwood. The main bath is also updated with double sinks and heated floors. The deck overlooks the Humber Valley Heritage Trail and forest. The finished basement includes media area, office area and a bedroom with an egress window, and a 3-piece bath. Located within St. Michaels Catholic Secondary and St. John Paul II school districts. Above ground heated saltwater pool. Roof 2015, furnace/ac 2013, windows 2019.

17 Shangrila Terrace, 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

$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

$2,199,000

3 Beds ⋅ 4 Baths ⋅ W13549302 MLS

Exceptional custom bungalow nestled on nearly 2 acres in one of Caledon's most prestigious executive enclaves. Set back from the road with a long private driveway, this remarkable property offers the perfect blend of luxury, privacy & convenience, just moments from HWY 50. Step outside & discover your own private resort. The beautifully landscaped grounds are designed for exceptional outdoor living, featuring a stunning saltwater inground pool, expansive patio, and an impressive covered outdoor kitchen that creates the ultimate space for entertaining all summer long. Mature trees & lush landscaping provide outstanding privacy, making this property feel like your own retreat. From the moment you enter, you'll be impressed by the cathedral ceilings that create a bright, open atmosphere throughout the grand foyer & elegant living room. The spacious eat-in kitchen, thoughtfully designed with an abundance of cabinetry & generous prep space for everyday living & effortless entertaining. The adjoining solarium is filled with natural light & offers the perfect setting to enjoy meals, unwind with a book, have your morning coffee or take in the peaceful views of the landscaped backyard. The thoughtfully designed main floor features a primary retreat with a walk-in closet & ensuite, along with spacious secondary bedrooms, a main floor laundry rm, and a functional mudroom with access to the backyard. The partially finished basement offers endless possibilities for additional living space, a rec room, home gym, or in-law potential, allowing you to customize it to suit your family's needs. Completing this incredible offering is an oversized three-car garage & ample parking. Rarely does a property combine executive living, resort-style amenities, and such a coveted Caledon location. Experience the tranquility of country living without sacrificing convenience, all tucked away in an exclusive neighbourhood just mins to major commuting routes, amenities, golf & conservation lands.

9 Moraine Place, Caledon

$1,639,000

4 Beds ⋅ 3 Baths ⋅ W13548102 MLS

Rare Caledon East Estate Lot | Nearly 1 Acre | Endless Possibilities Opportunities like this are becoming increasingly rare. Nestled on a spectacular pie shaped lot approaching one acre in one of Caledon East's most established and sought after neighbourhoods, this executive family residence offers the perfect blend of space, privacy and future potential. Surrounded by mature trees and lush landscaping, the property feels like a private country retreat while remaining just minutes from schools, amenities, and commuter routes. The backyard is designed for unforgettable gatherings, featuring a saltwater in-ground pool with attached hot tub, poolside cabana with hydro, expansive stonework, covered sunporch, and multiple outdoor entertaining areas that create a true resort style experience at home. Offering approx. 2600 sqft above grade, the home features spacious principal rooms and versatile layout that can comfortably accommodate growing families, multi-generational living, home offices and extended family under one roof. Whether you're hosting holidays, creating a family compound, or simple looking for room to breathe, this property delivers a lifestyle that is increasingly difficult to find. Beyond the itself lies the true value; the land. Large residential parcels of this size are exceptionally scarce in Caledon East and offers buyers the opportunity to secure a long term family estate in a neighbourhood where properties are tightly held. There may be future severance, redevelopment or estate planning potential , subject to all municipal approvals. For those seeking more than just a house - a place to build memories, create a legacy, and invest in a unique Piece of Caledon East -this is a truly exceptional offering.

19 Jean Street, Caledon

$1,349,900

4 Beds ⋅ 5 Baths ⋅ W13533608 MLS

Enjoy pool days in every season - all from the comfort of home! Set on a beautiful 1-acre lot along a paved country road and surrounded by towering mature trees, this spacious 2-storey home offers comfort, character, and a truly unique resort-style lifestyle.With over 3000 sq. ft. of living space, 4 bedrooms, and 5 bathrooms, this entertainer's dream is designed for everyday comfort and memorable gatherings. The enclosed pool area is a true showstopper, featuring an indoor inground pool, a cozy sitting area with a wood-burning fireplace, three clear roll-up doors, and patio doors leading to a covered outdoor dining space.The bright, open kitchen features ceiling-height cabinetry, a centre island with breakfast bar, modern pot lighting, and a walk-out from the breakfast area directly to the pool. The main level also offers multiple living spaces, including a formal dining room with fireplace, a living room with a second fireplace, and a spacious family room. Premium Jatoba hardwood flooring adds warmth and quality throughout the living, dining, and sitting areas.Upstairs, you'll find four bedrooms and two bathrooms. Major updates include a top-of-the-line geothermal system installed in 2016, central air conditioning with lifetime warranty, triple-pane thermal windows replaced approximately 9 years ago with lifetime warranty, and a 30-year three-tab shingle roof completed in September 2024. The hot water tank is owned, and the propane tank has been recently serviced. Outside, enjoy a detached 2-car garage, with loft and 3pc bathroom. This property boasts peaceful mature-treed surroundings, and plenty of outdoor space with lighting- all just a short drive to town amenities. A rare opportunity to enjoy privacy, space, and year-round poolside living.

19211 Mountainview Road, Caledon

$3,490,000

5 Beds ⋅ 5 Baths ⋅ W13512124 MLS

Welcome to 16609 Mount Wolfe Rd a Custom-built Luxury Estate Set on 2.92 Private Acres in Caledon, Offering Over 4700 Sq Ft Above Grade (as Per Mpac). From the Moment You Arrive Through the Automated Wrought Iron Gates, You're Greeted by a Serene Water Feature, Setting the Tone for What Lies Ahead. This 2011 Stone Bungalow Features Timeless Craftsmanship, Top-tier Materials, and Space to Live, Work, and Entertain inComfort. The Main Level Boasts 10-ft Ceilings, Radiant Heated Hickory and Marble Floors, and 8-ft Custom-stained Doors Throughout. The Gourmet Kitchen Includes Cherry Cabinetry, Granite Counters, Dual Islands, Sub-zero and Wolf Appliances. Enjoy a Grand Family Room and Formal Dining Area, With Limestone Fireplaces Both Designed for Gatherings and Day-to-day Elegance. The Executive Office/Cigar Room is Fully Appointed With a Fireplace and Professional-grade Ventilation Built For Productivity, Designed for Prestige. Ideal for Work Hard Play Hard. A True Highlight is the Oversized Main-floor Gym, Complete With Its Own Hot Tub, Perfect for Wellness and Recovery. The Luxurious Primary Suite Offers a Limestone Fireplace, Walk-in Closet, Steam Shower, Jacuzzi Tub, and Radiant Flooring. The Fully Finished Walkout Basement Includes a Soundproof Theatre With Reclining Chairs, a 900-bottle Climate-controlled Wine Cellar, and a Separate 2-bedroom Apartment With Private Kitchen, Laundry, and Its Own Entrances. But What Truly Sets This Estate Apart Are the Two Fully Equipped Workshops, Ideal for Contractors, Car Collectors, or Business Owners. Each Shop Offers 2,400sqft, 400 Amps, Separate Metering, and Heating All Accessed via Their Own Private, Fully Paved Driveway and Parking Area, Completely Separate From the Main Home Entrance. Outdoors, Enjoy a Heated Pool, Pool House With Washroom, Hot Tub, Outdoor Kitchen, Bar Area, and Professional Landscaping With Water Features. This Estate is Built for High-performance Living. SEE ATTACHMENTS

16609 Mount Wolfe Road, Caledon

$1,099,900

4 Beds ⋅ 3 Baths ⋅ W13509378 MLS

Welcome to 53 Marilyn Street, an exceptional opportunity to own a beautifully maintained detached home on a premium corner lot in one of Caledon East's most coveted family neighbourhoods. Surrounded by mature trees and prestigious homes, this property offers the perfect blend of privacy, space, and small-town charm. Step into your own backyard retreat featuring a massive entertainment deck, expansive greenspace, mature landscaping, an above-ground pool, storage shed, and a custom treehouse-creating the perfect setting for family fun and summer entertaining. Thoughtfully maintained with valuable updates including a high-efficiency furnace and central air conditioner (2021), hardwired security system with exterior surveillance cameras, and Bell Fibe directly to the home for ultra-fast internet and seamless remote work or streaming. Ideally located just minutes from excellent schools, parks, playgrounds, Caledon East Community Complex, arena, sports fields, scenic walking and cycling trails, conservation areas, restaurants, cafés, shopping and everyday amenities. Enjoy convenient access to Airport Road, Highway 10, Highway 9 and Highway 410, making commuting to Brampton, Vaughan, Pearson Airport and the GTA effortless while enjoying the peaceful lifestyle Caledon East is known for. Opportunities like this in Caledon East are exceptionally rare. A must-see!

53 Marilyn Street, Caledon

$2,500,000

4 Beds ⋅ 6 Baths ⋅ W13505786 MLS

Experience the perfect balance of luxury, nature, and convenience. This property will appeal to the discerning buyer seeking something truly special. Inside 6,500 square feet of thoughtfully blends open-concept living with cozy private retreats. Nestled on a unique, secluded 1.88-acre lot, this is not just another estate - it's an exclusive haven waiting to be yours. Bask in natural light in the stunning 2-story great room flowing seamlessly into the well appointed kitchen that offers space for multiple cooks and seamless entertaining. The 2nd story primary suite is a private retreat, complete with a luxurious five-piece ensuite and a massive walk-in closet. Two additional bedrooms on this floor each feature their own ensuite baths and walk-in closets, ensuring comfort and privacy for family or guests. A fourth bedroom, conveniently located on the main floor, offers its own adjacent 3-piece bath. Need more flexibility? Two main-floor offices provide ideal work-from-home setups or creative spaces. The fully finished walk-up basement is a world of possibilities. With a second kitchen, exercise room, media room, 2-piece bath, and ample storage, it's ready to be transformed into the ultimate entertainment space or in-law suite. Outside is your private paradise, where the lush yard and pool are surrounded by mature trees, offering complete tranquility. A sweeping drive and 3-car garage in the front. An outdoor living space tailored for unforgettable gatherings, featuring an inground pool, a cabana with a 2-piece bath, expansive patios, and deck areas for dining, lounging, and family fun in the back. Beyond the property, the Caledon Trailway, Credit River and the quaint village of Cheltenham are nearby, or explore local gems like Terra Cotta and Belfountain. With Pearson Airport only 30 minutes and downtown Toronto an hour's drive, this property offers countryside living without compromise.

57 Kennedy Road, Caledon

$2,829,000

8 Beds ⋅ 7 Baths ⋅ W13496264 MLS

Your search ends in this very cul de sac! Welcome to 4 Woodlot Court...Multigenerational living at it's finest! This majestic property is nothing short of breathtaking! Situated on a 2 acre lot nestled among gorgeous custom built estate homes! Take in the extensively landscaped yard as you make your way up the long drive to approach a beautifully appointed custom built home featuring over 5,000sf of living space + a finished walk out basement! This property has been lovingly cared for and meticulously maintained inside and out! Pride of ownership is evident the moment you enter this 6 + 2 Bed, 8 bath home boasting soaring 13' vaulted ceilings at the main living space, tastefully upgraded finishes throughout, 3 beds including the Primary bedroom on the main floor + 3 additional beds on the upper level, large windows throughout which offer a sun drenched interior, beautifully finished chic and modern walk out basement featuring 9' ceilings a bar, recreation room, games area, home gym, utility room and plenty of additional storage. Enjoy the versatility of this home whether you occupy it as a bungalow or a 2 storey the possibilities are endless!! Featuring a SELF CONTAINED in law suite that offers a 2 bed, 2 bath floor plan featuring approx. 1,200sf with garage and rear yard access which is PERFECT for aging parents, teenage children or to generate additional rental income!. Host your favourite guests while you soak up the rays of summer in the pool surrounded by gorgeous mature trees in the private oasis of a backyard where you will find a pool house with a kitchenette, washroom, changeroom, outdoor BBQ set up and all that you require to throw the most perfect party! Comfortably store all of your toys, cars, boats or belongings in the massive heated garage which contains 4 doors with the ability to park 5 vehicles! A true rare gem that has so much to offer situated in a highly coveted pocket of beautiful Palgrave..this one must be seen!

4 Woodlot Court, Caledon

$2,999,000

5 Beds ⋅ 6 Baths ⋅ W13490940 MLS

Discover a truly unique and breathtaking country estate where nature, privacy, and exceptional design come together in perfect harmony. Set on a picturesque 2.71 acres and ideally positioned between the Pulpit Club, Caledon Mountain Trout Club, Caledon Ski Club, Brampton Flying Club, and along the Bruce Trail, this magnificent property offers an unmatched lifestyle within close proximity to the city. A resort-like sanctuary awaits, designed for both grand entertaining and quiet, restorative living. An inground saltwater pool, outdoor shower, and cold plunge offer spa-like relaxation, while the wood-fired pizza oven, outdoor bar, and firepit create exceptional gathering spaces. Extensive, thoughtfully constructed walking trails wind throughout the grounds, complemented by aromatic and carefully curated gardens. A charming children's playhouse/bunkie, pool cabana, and 3 decks further enhance this one-of-a-kind outdoor setting. Inside, expansive windows fill the home with natural light and bring the outdoors in. The modern kitchen features marble countertops, stainless steel appliances, and a striking backsplash, flowing into the dining area. The living room is anchored by a stunning brick accent wall and wood-burning fireplace, while a home office with built-in desk and outdoor access provides a serene workspace. The main floor primary suite is a tranquil escape with a luxurious 4-pc ensuite and walk-in shower. Upstairs, 3 spacious bedrooms and 2 well-appointed baths provide comfort for family and guests. The 3rd floor loft serves as a wellness sanctuary with an infrared sauna and custom built-in sauna. Additional highlights include heated marble bathroom floors, new hardwood flooring, and a custom floor-to-ceiling glass wine cellar. Designed for peace of mind, the home features a backup generator, air quality systems, water treatment, and major electrical upgrades. Elegant, modern and immersed in nature - 2814 Forks of the Credit Road leaves nothing to be desired.

2814 Forks Of The Credit Road, Caledon

$959,999

5 Beds ⋅ 3 Baths ⋅ W13489596 MLS

Beautiful 3+2 Bedroom Bungalow with a WALK OUT BASEMENT!! Welcome to this stunning fully renovated bungalow nestled in the heart of Alton. This home features 3 spacious bedrooms on the main floor plus 2 full washrooms and a beautifully finished basement with 2 additional bedrooms and a 4 pc bathroom perfect for extended family or guests. Enjoy your private backyard oasis with an in-ground pool, relaxing hot tub, and plenty of space for entertaining on this expansive lot. A true blend of comfort, style, and outdoor luxury, this home has it all! Close to all major amenities.

32 Caledon Street, Caledon

$1,249,000

3 Beds ⋅ 2 Baths ⋅ W13475252 MLS

This is the opportunity you've been waiting for! Located in a family-friendly neighbourhood surrounded by multi-million-dollar homes, this property offers exceptional potential and outstanding value. Welcome to 44 Pineridge Drive, a charming bungalow nestled in the sought-after Gibson Lake community. Featuring a spacious open-concept layout, this home offers a large kitchen with plenty of storage, a generous dining room with a walkout to the patio, and an inground concretepool-perfect for entertaining family and friends. The finished basement provides additional living space, complete with a cozy fireplace, above-grade windows, and a separate side entrance, offering excellent flexibility for extended family living or future possibilities. Conveniently located close to schools, parks, and golf courses, this home combines comfort, convenience, and incredible potential. Don't miss this fantastic opportunity to own in a highly desirable location!

44 Pineridge Drive, Caledon

$3,588,000

4 Beds ⋅ 5 Baths ⋅ W13466736 MLS

Welcome To 258 Amos Drive-Luxury Estate On a Conservation-Backed Lot. Welcome To This Stunning 4-Bedroom , 5-Bathroom estate nestled on a Premium 183 X 758 Ft Lot with breathtaking , unobstructed views . Perfect for relaxation or entertaining, The backyard is private oasis featuring : Salt Water Pool 18 Feet X 36 Feet ,All-Season Cedar Sauna, All-Season Pool House With Washroom & Steam Shower, professionally landscaped grounds with sprinkler system front and back. Natural stone entrance porch and interlocking pathway .Inside, enjoy over 4800 sq.ft. of refined luxury with 8" Vintage Hardwood Floors Throughout, Pot Lights, and thoughtful, smart design. The gourmet kitchen is a chef's dream, featuring custom cabinetry with soft-close doors, walk-in pantry, Oversized Centre Island , Built-In Thermador appliances And A Breakfast Area With Walkout To A 21' X 24' Deck Overlooking The Backyard .The Family Room Features A Custom Wall TV Unit, Perfect For Cosy Movie Nights Or Entertaining Guests. The Primary Bedroom Serves As A Private Retreat With Sitting Area ,Two Walk-in Closets And A 5-piece Ensuite. All Closets in the Home Feature Professionally Installed Organizers. Additional Bedrooms Offer Ensuite Access And Walk-in Closets.The Home Also Offers 4 Car Garages With 2 Electrical Outlets For EV'S And A Heater In The Main Garage Area, Combining Convenience And Functionality. Whether Enjoying A Sunrise Coffee, Hosting Friends, Or Simply Relaxing In Style, This Property Offers Unparalleled Comfort , Luxury And Lifestyle - Truly-One-Of-A-Kind!

258 Amos Drive, Caledon

$8,000,000

5 Beds ⋅ 5 Baths ⋅ W13462682 MLS

Exceptional 10-acre country estate offering privacy, versatility, and outstanding lifestyle amenities. This spacious 2-storey brick home features a renovated kitchen (2022) with large island, farmhouse sink, pot fillers, stainless steel appliances, and abundant cabinetry. Enjoy oversized principal rooms, a cozy family room with fireplace and walkout to a deck and interlocking patio, plus 4 bedrooms including a primary suite with spa-inspired ensuite. The finished basement with separate entrance includes a second kitchen, rec room, 5-pc bath, laundry, and ample storage. A bright self-contained studio apartment with separate entrance, kitchen, bedroom, bath, and laundry provides ideal space for extended family or rental income. Outside, discover an above ground heated saltwater pool, pond, greenhouse with hydro, detached workshop with hydro, water, 2 bays and room for 5 vehicles, 2 woodsheds, and a heated 4-car attached garage. Updates include septic and furnace (2022), exterior doors (2022), and roof, soffits & eaves (2016).Located outside of the Greenbelt, close to the proposed HWY 413, this exceptional property offers the perfect blend of immediate multi generational enjoyment and long-term potential, positioned within an evolving and transitioning area poised for future growth. PROPERTY (INTERIOR -OR- EXTERIOR) TO BE VIEWED BY APPOINTMENT ONLY - PLEASE DO NOT APPROACH THE LOT UNLESS A REALTOR IS ACCOMPANYING YOU FOR YOUR SCHEDULED APPOINTMENT - THANKS FOR BEING RESPECTFUL TO THE SELLER(S).

13289 Innis Lake Road, Caledon

$1,125,000

4 Beds ⋅ 2 Baths ⋅ W13455320 MLS

A Storybook Country Escape in the Heart of Caledon! Tucked among mature trees and rolling hills, this one-of-a-kind country retreat offers the perfect blend of character, privacy, and outdoor living. Set on just over an acre, the property feels worlds away from the hustle of everyday life, yet remains conveniently close to charming villages, trails, ski hills, and local amenities. Inside, warmth and authenticity greet you at every turn. Soaring beamed ceilings, wide plank floors, and a stunning stone fireplace create an atmosphere that is both inviting and unforgettable. The spacious living and dining areas are designed for gathering with family and friends, while large windows frame beautiful views of the surrounding landscape. Upstairs, the primary suite is a peaceful sanctuary with its own sitting area and direct access to the backyard oasis. A third-level loft and additional bedroom provide flexible space for guests, a home office, creative studio, or quiet retreat. Outside is where this property truly shines. Wander along flagstone pathways through established perennial gardens, spend summer afternoons lounging by the pool, and gather around the firepit under a canopy of stars. The detached workshop offers endless possibilities for hobbyists, artists, gardeners, or extra storage. Whether you're searching for a full-time residence or a weekend escape, this remarkable property offers something increasingly difficult to find - a home with soul, surrounded by nature, where every season brings a new reason to fall in love.

20909 Shaws Creek Road, Caledon

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