Caledon Real Estate Search

Caledon Properties between $2,000,000 and $3,000,000 for Sale

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Newest Caledon Properties between $2,000,000 and $3,000,000 for Sale

$2,550,000
5 Beds 3 Baths W13597554 MLS® #
Custom bungalow offering over 5,000 sq ft of finished living space in Bolton. Situated on just over 1/2 an acre. Surrounded by open fields along the rear and north side, this property delivers a rare combination of privacy, and space. The home features a large covered front porch and massive interlocked driveway providing ample private parking, complemented by a double car garage with interior access. Spacious main level highlighted by large windows that flood the home with natural light. The functional layout includes 3 generously sized bedrooms, 2 bathrooms (including a 5-piece ensuite), a private office, and a large living room with a fireplace and walk-out to the backyard patio. The main kitchen features an island, breakfast bar, and separate dining area. An additional front family room and formal dining/entertainment space provide flexibility forgatherings and everyday comfort.The fully finished basement offers a separate entrance, ideal for an in-law suite or potential rental income. Basement includes a 2nd full kitchen & dining area, 2 additional bedrooms, aspacious living room with a cozy wood-burning fireplace, and a large entertainment area complete with a wet bar, coffee/drink station, and pool table setup. A dedicated laundry area,storage, and workshop space complete the lower level.The backyard features a large patio area perfect for entertaining, along with expansive greenspace ideal for families, outdoor activities, or simply enjoying the peaceful surroundings. A rare opportunity to own a sprawling bungalow on a premium lot with multi-generational living potential in a highly sought-after location. (id:5764)

12792 Humber Station Road, Caledon

Listing courtesy of RE/MAX EXPERTS.

$2,550,000
5 Beds 3 Baths W13597554 MLS® #
Custom bungalow offering over 5,000 sq ft of finished living space in Bolton. Situated on just over 1/2 an acre. Surrounded by open fields along the rear and north side, this property delivers a rare combination of privacy, and space. The home features a large covered front porch and massive interlocked driveway providing ample private parking, complemented by a double car garage with interior access. Spacious main level highlighted by large windows that flood the home with natural light. The functional layout includes 3 generously sized bedrooms, 2 bathrooms (including a 5-piece ensuite), a private office, and a large living room with a fireplace and walk-out to the backyard patio. The main kitchen features an island, breakfast bar, and separate dining area. An additional front family room and formal dining/entertainment space provide flexibility forgatherings and everyday comfort.The fully finished basement offers a separate entrance, ideal for an in-law suite or potential rental income. Basement includes a 2nd full kitchen & dining area, 2 additional bedrooms, aspacious living room with a cozy wood-burning fireplace, and a large entertainment area complete with a wet bar, coffee/drink station, and pool table setup. A dedicated laundry area,storage, and workshop space complete the lower level.The backyard features a large patio area perfect for entertaining, along with expansive greenspace ideal for families, outdoor activities, or simply enjoying the peaceful surroundings. A rare opportunity to own a sprawling bungalow on a premium lot with multi-generational living potential in a highly sought-after location.

12792 Humber Station Road, Caledon

Listing courtesy of RE/MAX EXPERTS.

$2,795,000
4 Beds 3 Baths W13577360 MLS® #
50 acres - Exceptional country farm and retreat in the Heart of Caledon. Set along picturesque Shaws Creek Road, this beautifully renovated country property blends timeless red brick farmhouse charm, including the wrap-around porch, with a thoughtfully designed equestrian facility, creating the ultimate live-work lifestyle. The inviting 1.5-storey home has been extensively updated while preserving its character, featuring hardwood flooring, bright, welcoming living spaces, and three spacious bedrooms designed for comfortable family living. Adding incredible versatility is the oversized three-car detached garage with a self-contained one-bedroom suite above, complete with a full kitchen and living room-ideal for extended family, guests or staff accommodations. Designed with horse enthusiasts and professionals in mind, the impressive equestrian facilities include a well-equipped main barn with 14 stalls, office, tack room, and feed room, complemented by a second barn offering an additional three stalls and dedicated tack area. The property features nine fenced paddocks and three professionally designed round pens, each serviced with frost-free water, while the centre round pen is equipped with automatic watering for added convenience and efficiency. This 50-acre parcel offers an outstanding combination of pasture, riding space, trails to enjoy, and open land, providing endless opportunities for boarding, training, breeding, or simply enjoying the peaceful country lifestyle. Located in one of Caledon's most sought-after rural settings, just a short drive to Orangeville, Erin, Georgetown, Brampton, and the GTA, this is a rare opportunity to own a turnkey equestrian property where exceptional facilities meet comfortable country living. A truly special offering for riders, trainers, hobby farmers, or anyone seeking the space, privacy, and beauty that only Caledon can provide. (id:5764)

20855 Shaws Creek Road, Caledon

Listing courtesy of COLDWELL BANKER RONAN REALTY.

$2,795,000
4 Beds 3 Baths W13577360 MLS® #
50 acres - Exceptional country farm and retreat in the Heart of Caledon. Set along picturesque Shaws Creek Road, this beautifully renovated country property blends timeless red brick farmhouse charm, including the wrap-around porch, with a thoughtfully designed equestrian facility, creating the ultimate live-work lifestyle. The inviting 1.5-storey home has been extensively updated while preserving its character, featuring hardwood flooring, bright, welcoming living spaces, and three spacious bedrooms designed for comfortable family living. Adding incredible versatility is the oversized three-car detached garage with a self-contained one-bedroom suite above, complete with a full kitchen and living room-ideal for extended family, guests or staff accommodations. Designed with horse enthusiasts and professionals in mind, the impressive equestrian facilities include a well-equipped main barn with 14 stalls, office, tack room, and feed room, complemented by a second barn offering an additional three stalls and dedicated tack area. The property features nine fenced paddocks and three professionally designed round pens, each serviced with frost-free water, while the centre round pen is equipped with automatic watering for added convenience and efficiency. This 50-acre parcel offers an outstanding combination of pasture, riding space, trails to enjoy, and open land, providing endless opportunities for boarding, training, breeding, or simply enjoying the peaceful country lifestyle. Located in one of Caledon's most sought-after rural settings, just a short drive to Orangeville, Erin, Georgetown, Brampton, and the GTA, this is a rare opportunity to own a turnkey equestrian property where exceptional facilities meet comfortable country living. A truly special offering for riders, trainers, hobby farmers, or anyone seeking the space, privacy, and beauty that only Caledon can provide.

20855 Shaws Creek Road, Caledon

Listing courtesy of COLDWELL BANKER RONAN REALTY.

$2,099,900
3 Beds 3 Baths W13573802 MLS® #
Beautiful custom-built Bungalow-Raised on a stunning 6+ acre treed rolling lot in sought-after Caledon. Featuring a small stream along the southwest portion of the property, this home offers privacy, natural beauty, and refined country living just minutes from amenities and 400-series highways .Inside showcases hardwood floors, crown moulding, cathedral and vaulted ceilings, elegant trim work, and a bright open layout. Enjoy an oversized heated 3-car garage with direct interior access, a chef-inspired kitchen with brand-new high-end appliances, spacious living room with gas fireplace, separate dining area, and walkout to a deck overlooking the property. The main level offers 3 generous bedrooms, including a primary suite with Ensuite bath, walk-in closet, and brand-new custom closet & organizers. The bright walkout lower level features high ceilings, large windows, drywall, rough-in bath, ample storage, and double-door access to the backyard, ready for your finishing touches. Perfect for luxury buyers, outdoor enthusiasts, and nature lovers seeking privacy, space, and refined country living in one of Caledon's most desirable locations.Highlights:6+ acre treed rolling lot with stream Custom-built Bungalow-Raised Heated oversized 3-car garage400 AMP electrical service with 200 AMP panels for house and garage. Brand-new high-end kitchen appliances. Bright walkout lower level with rough-in bath Close to parks, trails, Caledon Lake, fairgrounds, golf courses, amenities, and highways. (id:5764)

20051 Willoughby Road, Caledon

Listing courtesy of HOMELIFE SILVERCITY REALTY INC..

$2,099,900
3 Beds 3 Baths W13573802 MLS® #
Beautiful custom-built Bungalow-Raised on a stunning 6+ acre treed rolling lot in sought-after Caledon. Featuring a small stream along the southwest portion of the property, this home offers privacy, natural beauty, and refined country living just minutes from amenities and 400-series highways .Inside showcases hardwood floors, crown moulding, cathedral and vaulted ceilings, elegant trim work, and a bright open layout. Enjoy an oversized heated 3-car garage with direct interior access, a chef-inspired kitchen with brand-new high-end appliances, spacious living room with gas fireplace, separate dining area, and walkout to a deck overlooking the property. The main level offers 3 generous bedrooms, including a primary suite with Ensuite bath, walk-in closet, and brand-new custom closet & organizers. The bright walkout lower level features high ceilings, large windows, drywall, rough-in bath, ample storage, and double-door access to the backyard, ready for your finishing touches. Perfect for luxury buyers, outdoor enthusiasts, and nature lovers seeking privacy, space, and refined country living in one of Caledon's most desirable locations.Highlights:6+ acre treed rolling lot with stream Custom-built Bungalow-Raised Heated oversized 3-car garage400 AMP electrical service with 200 AMP panels for house and garage. Brand-new high-end kitchen appliances. Bright walkout lower level with rough-in bath Close to parks, trails, Caledon Lake, fairgrounds, golf courses, amenities, and highways.

20051 Willoughby Road, Caledon

Listing courtesy of HOMELIFE SILVERCITY REALTY INC..

$2,349,000
5 Beds 6 Baths W13569356 MLS® #
Welcome to this exceptional custom-built stone and brick residence nestled on a private 2.25-acre estate lot surrounded by breath taking countryside views. This impressive 2-storey home offers 4,444 sq. ft. above grade of finished living space, featuring soaring ceilings on both the main and second floors, an unfinished walk-out basement, and a beautifully landscaped fenced property with a natural stream running through. Enjoy peaceful sunsets and panoramic views from the expansive deck overlooking the terraced backyard. The grand foyer with cathedral ceilings opens to a spacious great room featuring a fireplace, pot lighting, and oversized windows allowing an abundance of natural light. The custom-designed kitchen showcases granite countertops, a large centre island, crown moulding, and a stylish matching backsplash, creating the perfect space for entertaining. Elegant hardwood flooring extends throughout both the main and second levels, complemented by superior craftsmanship and quality finishes throughout. The luxurious primary suite offers a spa-inspired 5-piece ensuite, providing a private retreat at the end of the day. Designed with comfort and versatility in mind, this home is ideal for large or multi-generational families seeking space, privacy, and modern living surrounded by nature. A rare opportunity to enjoy country tranquility with the convenience of a beautifully appointed custom home. (id:5764)

18118 Heart Lake Road South, Caledon

Listing courtesy of RE/MAX COMMUNITY REALTY INC..

$2,349,000
5 Beds 6 Baths W13569356 MLS® #
Welcome to this exceptional custom-built stone and brick residence nestled on a private 2.25-acre estate lot surrounded by breath taking countryside views. This impressive 2-storey home offers 4,444 sq. ft. above grade of finished living space, featuring soaring ceilings on both the main and second floors, an unfinished walk-out basement, and a beautifully landscaped fenced property with a natural stream running through. Enjoy peaceful sunsets and panoramic views from the expansive deck overlooking the terraced backyard. The grand foyer with cathedral ceilings opens to a spacious great room featuring a fireplace, pot lighting, and oversized windows allowing an abundance of natural light. The custom-designed kitchen showcases granite countertops, a large centre island, crown moulding, and a stylish matching backsplash, creating the perfect space for entertaining. Elegant hardwood flooring extends throughout both the main and second levels, complemented by superior craftsmanship and quality finishes throughout. The luxurious primary suite offers a spa-inspired 5-piece ensuite, providing a private retreat at the end of the day. Designed with comfort and versatility in mind, this home is ideal for large or multi-generational families seeking space, privacy, and modern living surrounded by nature. A rare opportunity to enjoy country tranquility with the convenience of a beautifully appointed custom home.

18118 Heart Lake Road S, Caledon

Listing courtesy of RE/MAX COMMUNITY REALTY INC..

$2,899,999
4 Beds 3 Baths W12665728 MLS® #
Discover the perfect blend of luxury and convenience with this stunning property that featuresTWO separate homes within the property. This property is ideal for a family that care to havetheir immediate family nearby. This dream home is nestled in the serene surroundings of Caledon, and is located in the beautiful Terra-Cotta Caledon. This property is perfect forthose seeking tranquillity with the convenience of city life just a short drive away from the city. These picturesque views from this immaculate four-bedroom home have a peaceful and private40 acre lot, with towering and mature trees in a gorgeous wildflower Garden. Relax and unwindwhile listening to the sound of nature, whether on the main deck or the second deck that hasaccess from the kitchen with a beautiful, breathtaking view. The second floor is overlooking thestunning tall trees filled with nature and a beautiful panoramic view thatyou just won't want to leave. The living rooms of her beautiful ash masonry from all anglesof the house, not to mention the fireplace in the master room. The Eden kitchen features a skylight and floor-to-ceiling windows from both sides overlooking the backyard and wildlifeenjoying the second home that is featured on this property and is renovated from top to bottom. The second one includes a meeting with a board room a bathroom a full bathroom, and a kitchenand not to mention the beautiful surrounding nature around the second house as well. Wildlifeabounds with birds, turkeys, and deer come for a visit and you will not want to leave the home.This property is managed to conservation area skiing, luxury God, is on a spa resort 45 minutes to Pearson airport. This property comes with gated entry. Both homes have separate meters. Hur ryand make this your dream home. (id:5764)

15139 Rockside Road, Caledon

Listing courtesy of RE/MAX REALTY SPECIALISTS INC..

$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

Listing courtesy of COLDWELL BANKER RONAN REALTY.

$2,399,000
6 Beds 6 Baths W13537978 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

Listing courtesy of RE/MAX REAL ESTATE CENTRE INC..

$2,699,000
5 Beds 5 Baths W13527704 MLS® #
Welcome to this exceptional 2-storey estate residence offering approximately 4,000 sq. ft. of beautifully appointed living space across the main and second levels, perfectly positioned on a breathtaking 2.74-acre lot in prestigious Millcreek Estates, an exclusive Caledon enclave renowned for its privacy and natural beauty. This magnificent 4+1 bedroom home showcases timeless elegance and exceptional craftsmanship, featuring rich hardwood flooring, crown moulding, oversized baseboards, designer lighting, pot lights, and soaring 10-ft ceilings throughout. A grand foyer introduces elegant principal rooms, including a formal dining room ideal for entertaining. The spectacular living room boasts floor-to-ceiling windows, a fireplace, and a walk-out to the expansive upper deck overlooking tranquil, tree-lined greenspace. The chef-inspired kitchen features premium built-in appliances, a gas cooktop, oversized centre island with breakfast bar, and a bright breakfast area with walk-out access. The adjoining family room with fireplace offers a warm, inviting space with serene backyard views. The main-floor primary suite is a luxurious retreat with walk-out access, a spa-inspired 5-piece ensuite, and his-and-hers walk-in closets. A mudroom with custom built-ins and separate entrance, direct garage access, a spacious laundry room and 2-piece guest washroom complete the main level. Upstairs, three generously sized bedrooms each feature private ensuites; two include walk-in closets, while the third offers a double closet. The finished walkout lower level provides an additional 2,868.49 sq. ft. with a recreation room, games area, family room with fireplace, cold room(s), abundant storage, and exceptional multi-generational living potential. A 4-car garage, professionally landscaped grounds, and an extraordinary setting complete this remarkable estate, offering an exceptional lifestyle of luxury, privacy, and natural beauty. (id:5764)

7 Proctor Avenue, Caledon

Listing courtesy of ROYAL LEPAGE RCR REALTY.

$2,699,000
5 Beds 5 Baths W13527704 MLS® #
Welcome to this exceptional 2-storey estate residence offering approximately 4,000 sq. ft. of beautifully appointed living space across the main and second levels, perfectly positioned on a breathtaking 2.74-acre lot in prestigious Millcreek Estates, an exclusive Caledon enclave renowned for its privacy and natural beauty. This magnificent 4+1 bedroom home showcases timeless elegance and exceptional craftsmanship, featuring rich hardwood flooring, crown moulding, oversized baseboards, designer lighting, pot lights, and soaring 10-ft ceilings throughout. A grand foyer introduces elegant principal rooms, including a formal dining room ideal for entertaining. The spectacular living room boasts floor-to-ceiling windows, a fireplace, and a walk-out to the expansive upper deck overlooking tranquil, tree-lined greenspace. The chef-inspired kitchen features premium built-in appliances, a gas cooktop, oversized centre island with breakfast bar, and a bright breakfast area with walk-out access. The adjoining family room with fireplace offers a warm, inviting space with serene backyard views. The main-floor primary suite is a luxurious retreat with walk-out access, a spa-inspired 5-piece ensuite, and his-and-hers walk-in closets. A mudroom with custom built-ins and separate entrance, direct garage access, a spacious laundry room and 2-piece guest washroom complete the main level. Upstairs, three generously sized bedrooms each feature private ensuites; two include walk-in closets, while the third offers a double closet. The finished walkout lower level provides an additional 2,868.49 sq. ft. with a recreation room, games area, family room with fireplace, cold room(s), abundant storage, and exceptional multi-generational living potential. A 4-car garage, professionally landscaped grounds, and an extraordinary setting complete this remarkable estate, offering an exceptional lifestyle of luxury, privacy, and natural beauty.

7 Proctor Avenue, Caledon

Listing courtesy of ROYAL LEPAGE RCR REALTY.

$2,199,000
6 Beds 5 Baths W13518834 MLS® #
**In Law Suite at $2400/Month** 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

Listing courtesy of RE/MAX REALTY SPECIALISTS INC..

$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

Listing courtesy of KELLER WILLIAMS EDGE REALTY.

$2,500,000
4 Beds 7 Baths 40844026 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. (id:5764)

57 KENNEDY Road, Caledon

Listing courtesy of Keller Williams Edge Realty.

$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

Listing courtesy of RE/MAX EXPERTS.

$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. (id:5764)

2814 Forks Of The Credit Road, Caledon

Listing courtesy of SAM MCDADI REAL ESTATE INC..

$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

Listing courtesy of SAM MCDADI REAL ESTATE INC..

$2,899,999
5 Beds 6 Baths W13453766 MLS® #
Rarely does a property come to market that truly offers it all. Welcome to 11 Damascus Drive, a beautifully renovated estate home set on a private 2.55-acre lot in one of Caledon East's most sought-after cul-de-sacs.Boasting over 3,800 sq. ft. of finished living space, including a legal in-law suite, this exceptional property has been extensively updated from top to bottom and is completely move-in ready. The heart of the home is a stunning chef-inspired kitchen featuring quartz countertops, a waterfall island, premium built-in appliances including a JennAir refrigerator, and a fully equipped spice kitchen. Hardwood flooring, designer finishes, updated windows and doors, modern lighting, and beautifully renovated bathrooms elevate every space.Designed with both family living and entertaining in mind, the home offers spacious principal rooms, a welcoming family room with a striking fireplace feature wall, and a luxurious primary retreat complete with a spa-inspired ensuite and walk-through dressing area. The finished lower level provides additional living space for family, guests, or recreation.A standout feature is the legal in-law suite with its own entrance, kitchen, bedroom area, and full bathroom, offering incredible flexibility for multigenerational living or future income potential.Step outside and discover your own private backyard oasis. Surrounded by mature trees, enjoy summer days by the large in-ground pool, recently updated with a new liner, pump, heater, and filtration system, along with an expansive deck perfect for relaxing or entertaining. A triple-car garage and circular driveway complete this impressive estate setting.Offering the perfect balance of privacy and convenience, this remarkable property is just minutes from schools, shopping, and everyday amenities. Luxury, space, and versatility-11 Damascus Drive truly has it all.

11 Damacus Drive, Caledon

Listing courtesy of FLOWER CITY SIGNATURE REALTY INC..

$2,299,000
4 Beds 4 Baths W13448324 MLS® #
Stop searching for your dream home-this is the one! Situated on a premium 1+ acre lot, this stunning custom-built bungalow showcases exceptional craftsmanship and luxury upgrades throughout. A grand foyer with over 12-foot ceilings and double-door entry welcomes you into elegant living and dining spaces featuring coffered ceilings and recessed lighting. The impressive family room boasts soaring 14-foot ceilings with cove lighting, while the chef-inspired kitchen is equipped with premium appliances, a gas range, oversized panel-ready fridge and dishwasher, servery, full pantry, oversized island, and abundant cabinetry. Large windows with custom blinds flood the home with natural light. The luxurious primary suite offers a custom walk-in closet and spa-like ensuite with a designer tub, towel warmer, and glass shower, while a second primary bedroom includes its own private ensuite. The thoughtfully designed mudroom features custom cabinetry, shoe storage, and a built-in bench. The walk-out basement provides an incredible opportunity to add approximately 3000 sq. ft. of additional living space and is already partially completed with drywall, electrical, plumbing, and heated floor rough-ins. Planned for 9-foot ceilings, a full kitchen, living area, two bedrooms, theatre room, gym, sauna, and two bathrooms, this remarkable home is built far above standard code requirements and offers the perfect blend of luxury, comfort, and future potential. (id:5764)

19769 Willoughby Road, Caledon

Listing courtesy of RE/MAX GOLD REALTY INC..

$2,495,000
7 Beds 5 Baths W13448626 MLS® #
Stunning Builders Custom Designed Unique Grand Estate on a Scenic lot Boasting over 8000 sq ft of finished spaced ! 5189 sq ft (3789sqft main floor,1400sqft upper loft) + 3000Sqft of finished livable space. Built with steel beams and Concrete Floors Beneath Cherry Hardwood & Stone Tiles gives you noise free comfort and strength. Gorgeous views from every corner! Plenty of space and privacy ! Built for Entertaining and for family ! open concept family and kitchen, (this kitchen has a Massive walk in pantry With rough in for a 2nd kitchen and has a walkout to the deck) separate living & dining, powder room, 2 beds and another 3 pce bath plus the master all on the main floor. The Mater Suite is STUNNING it has an Ensuite bath fit for a royalty with gorgeous views, plus a sitting area and walkout to the massive deck! Walk in closet has a MAKE UP CENTRE & LAUNDRY. A 2nd story Loft that's over 1400 sq ft and has 2nd great room/family room with impressive views & 2 beds and a bath ! Fin W/O Bsmt with multiple walkouts and a 2nd laundry thats almost 3000m sq ft, Then, there's a Tennis Court, a circular drive, views of the pond next door, Wooded 5.08 Acres, 2 furnaces 3 car garage, way too much to list ! This home is an amazing combination of custom design & Luxury. sellers are downsizing and are willing to assist in updated the home to your taste prior to closing !! this home has the potential for multi generational living, or for a 2nd basement apartment (id:5764)

19 Tanglewood Drive, Caledon

Listing courtesy of HOMELIFE/MIRACLE REALTY LTD.

$2,495,000
7 Beds 5 Baths W13448626 MLS® #
Stunning Builders Custom Designed Unique Grand Estate on a Scenic lot Boasting over 8000 sq ft of finished spaced ! 5189 sq ft (3789sqft main floor,1400sqft upper loft) + 3000Sqft of finished livable space. Built with steel beams and Concrete Floors Beneath Cherry Hardwood & Stone Tiles gives you noise free comfort and strength. Gorgeous views from every corner! Plenty of space and privacy ! Built for Entertaining and for family ! open concept family and kitchen, (this kitchen has a Massive walk in pantry With rough in for a 2nd kitchen and has a walkout to the deck) separate living & dining, powder room, 2 beds and another 3 pce bath plus the master all on the main floor. The Mater Suite is STUNNING it has an Ensuite bath fit for a royalty with gorgeous views, plus a sitting area and walkout to the massive deck! Walk in closet has a MAKE UP CENTRE & LAUNDRY. A 2nd story Loft that's over 1400 sq ft and has 2nd great room/family room with impressive views & 2 beds and a bath ! Fin W/O Bsmt with multiple walkouts and a 2nd laundry thats almost 3000m sq ft, Then, there's a Tennis Court, a circular drive, views of the pond next door, Wooded 5.08 Acres, 2 furnaces 3 car garage, way too much to list ! This home is an amazing combination of custom design & Luxury. sellers are downsizing and are willing to assist in updated the home to your taste prior to closing !! this home has the potential for multi generational living, or for a 2nd basement apartment

19 Tanglewood Drive, Caledon

Listing courtesy of HOMELIFE/MIRACLE REALTY LTD.

$2,299,000
4 Beds 4 Baths W13448324 MLS® #
Stop searching for your dream home-this is the one! Situated on a premium 1+ acre lot, this stunning custom-built bungalow showcases exceptional craftsmanship and luxury upgrades throughout. A grand foyer with over 12-foot ceilings and double-door entry welcomes you into elegant living and dining spaces featuring coffered ceilings and recessed lighting. The impressive family room boasts soaring 14-foot ceilings with cove lighting, while the chef-inspired kitchen is equipped with premium appliances, a gas range, oversized panel-ready fridge and dishwasher, servery, full pantry, oversized island, and abundant cabinetry. Large windows with custom blinds flood the home with natural light. The luxurious primary suite offers a custom walk-in closet and spa-like ensuite with a designer tub, towel warmer, and glass shower, while a second primary bedroom includes its own private ensuite. The thoughtfully designed mudroom features custom cabinetry, shoe storage, and a built-in bench. The walk-out basement provides an incredible opportunity to add approximately 3000 sq. ft. of additional living space and is already partially completed with drywall, electrical, plumbing, and heated floor rough-ins. Planned for 9-foot ceilings, a full kitchen, living area, two bedrooms, theatre room, gym, sauna, and two bathrooms, this remarkable home is built far above standard code requirements and offers the perfect blend of luxury, comfort, and future potential.

19769 Willoughby Road, Caledon

Listing courtesy of RE/MAX GOLD REALTY INC..

$2,488,000
4 Beds 5 Baths W13445982 MLS® #
This newly custom-built home at 86 Willow Street in Bolton showcases exceptional quality and stunning design that set a new standard for luxury living in Bolton East. Every element reflects meticulous craftsmanship, thoughtful planning, and premium finishes. Soaring ceilings, expansive windows, and a seamless open-concept layout create a bright, grand, and inviting atmosphere throughout. The gourmet kitchen is a true masterpiece, featuring exquisite book-matched countertops and backsplash with dramatic veining. This stunning stonework is perfectly echoed in the matching fireplace mantle, creating a cohesive and luxurious focal point. Custom-built-in millwork and high-end lighting add refined elegance and warmth to every room. A rare Cambridge elevator offers effortless access between all levels. The dining room features a sophisticated custom temperature-controlled wine cellar, perfect for the discerning collector. The primary retreat is an unparalleled private sanctuary, highlighted by a double-sided fireplace with a dramatic custom feature wall, a convenient wet bar with beverage fridges, a massive walk-in closet with organizers, and a stunning 6-piece ensuite with heated flooring and roughed in steam shower, that offers true spa-like indulgence. The lower level remains unfinished, providing a blank canvas for your personal vision and future customization. This is custom construction at its finest - where exceptional quality meets stunning design in perfect harmony. Located in a sought-after Bolton neighbourhood, 86 Willow Street is a rare opportunity to own a truly exceptional home.

86 Willow Street, Caledon

Listing courtesy of RE/MAX EXPERTS.

$2,199,900
6 Beds 5 Baths W13429926 MLS® #
Exceptional newer custom-built residence offering 4,088 sq. ft. above grade, thoughtfully designed w/ premium finishes, timeless elegance & endless potential. From the moment you step inside the breathtaking 20-ft grand foyer, you'll appreciate the quality craftsmanship showcased t/o.Featuring 7.5-in engineered hardwood flooring t/o, smooth ceilings, 10-ft main floor ceilings, 9-ft upper ceilings & extensive custom millwork incl. 7.5-in baseboards & 4.5-in door & window casings, every detail has been carefully curated. Architectural coffered ceilings elevate the Liv Rm, office, hallways & primary bdrm, while elegant wainscotting detailing enhances the Fam Rm & formal Din Rm. The stunning custom kitchen is the heart of the home, complete w/ quartz countertops, premium cabinetry & an O/C layout ideal for entertaining.The spacious Liv Rm is anchored by a cozy gas fireplace, while the formal Din Rm/home office showcases refined custom detailing. Upstairs, you'll find 5 generously sized bdrms, an upper-level laundry rm & luxurious baths featuring quartz countertops, porcelain tile finishes, glass shower enclosures & heated floors in 2 baths.The impressive open-riser staircase w/ modern glass railings adds a sophisticated architectural touch. The unfinished 1685sqft lower level offers incredible future potential w/ a fully roughed-in kitchen & bath, heated floors & a functional 2-bdrm layout, making it ideal for multi-generational living, an in-law suite or future income potential.Outside, enjoy a beautifully finished interlock driveway & backyard patio, a 4-car tandem garage & parking for an add'l 5 vehicles. Enjoy easy access to Caledon East Village, local shops, restaurants, grocery stores, parks, community centres, golf courses, top-rated schools, scenic conservation areas, walking & cycling trails & major routes incl. Hwy 410, Hwy 10 & Hwy 50 for an easy commute t/o the GTA. A rare opportunity to own a newer custom home where luxury & future potential come together.

6425 Old Church Road, Caledon

Listing courtesy of RE/MAX WEST REALTY INC..

$2,998,000
5 Beds 2 Baths W13428300 MLS® #
Welcome To 16718 Caledon King Townline N An Exceptional Opportunity To Own A Private Country Estate On Nearly 25 Acres In Prestigious Palgrave. Tucked Behind A Gated Entrance And Surrounded By Mature Trees, This Remarkable Property Offers The Perfect Blend Of Luxury, Privacy, And Endless Potential. The Spacious 5-Bedroom Home Features Generous Principal Rooms,Soaring High Ceilings, Large Windows With Scenic Views, And A Warm, Functional Layout Ideal For Family Living Or Entertaining. Whether You're Looking To Create Your Dream Retreat Or Enjoy Peaceful Country Living, This Home Provides The Perfect Canvas. Ideal For Equestrian Enthusiasts Or Hobby Farmers, The Property Features A Well-Equipped 6-Stall Barn, Multiple Paddocks, Open Pastures, And Two Scenic Ponds That Enhance The Natural Beauty Of The Landscape. A Detached 1,200 Sq Ft Workshop And Oversized Garage Offer IncredibleFlexibility For Storage, Business Use, Equipment, Or Passion Projects. Step Outside And Enjoy Resort-Style Living With A Private Inground Pool, Expansive Green Space, And Complete Serenity All Just Minutes From Town Amenities. Conveniently Located Only 10 Minutes To Bolton, Schomberg, And Tottenham, With Easy Access To Major Routes. A Rare Offering Combining Lifestyle, Nature, Privacy, And The Opportunity To Own A Truly Special Property In One Of Caledon's Most Desirable Areas.

16718 Caledon King Townline N, Caledon

Listing courtesy of RE/MAX MILLENNIUM REAL ESTATE.

$2,000,000
5 Beds 4 Baths W13419746 MLS® #
Set on just over 1 acre in highly desirable South Caledon, this beautifully renovated bungalow is surrounded by picturesque farms, estate homes, and tranquil countryside views. Offering a perfect blend of charm, modern décor, and quality upgrades throughout, this spacious residence features 5 bedrooms, including 3 on the main floor, and an impressive open-concept layout ideal for everyday living and entertaining. The heart of the home is the entertainer's dream chef's kitchen, showcasing marble countertops, high-end appliances, ample cabinetry and storage, and a seamless connection to the main living areas. Elegant, heated flooring, Custom woodwork & Wainscotting details, distinctive porcelain tile, skylights, and a stunning double-sided stone fireplace add warmth, character, and sophistication throughout the home. The luxurious primary bedroom retreat features a beautifully appointed ensuite complete with laundry area, wet bar, steam shower, separate toilet cubicle, and upscale finishes. Additional main-floor highlights include an inviting den, a bright sun-filled living room with heated floors, and a modern geothermal heating system for year-round comfort and efficiency. The finished lower level offers excellent flexibility with 2 additional bedrooms, a full bathroom, recreation room, kitchen, and separate laundry area. With a walk-up to the garage, this space is ideally suited for extended family, in-law living, or multi-generational use. Outdoors, enjoy a large multi-level deck overlooking the scenic surroundings, a fenced and gated private inground swimming pool with upgraded liner, and a relaxing hot tub. The property also features ample driveway parking and a beautiful, covered porch, creating wonderful curb appeal and a welcoming entrance. Recent upgrades include a new well pump and new pressure tank, both completed in 2025.A rare opportunity to enjoy country living, modern comfort, and exceptional privacy in one of South Caledon's most desirable settings.

3585 Boston Mills Road, Caledon

Listing courtesy of RE/MAX SPECIALISTS TAVSELLS INC..

$2,999,000
5 Beds 6 Baths W13242242 MLS® #
Custom-Built Estate Home offering 8,586 sq. ft. of luxury living space as per MPAC, set on 24+ acres of complete privacy in the prestigiousVillage of Terra Cotta. Built with no expense spared, this one-of-a-kind residence showcases imported stone, Brazilian hardwood floors, marblefinishes, heated flooring, German-engineered windows, custom millwork, and a lifetime metal roof (2024). The main level features 3 bedroomswith ensuite privileges including a primary retreat with walk-through closet, spa-inspired ensuite, and Juliette balcony. A gourmet kitchenoverlooks the family room and flows seamlessly into a sun-filled sunroom walkout, perfect for year-round enjoyment. The fully finished walkoutbasement boasts soaring 10 ft ceilings, heated floors throughout, a second kitchen, wine cellar, recreation room, 2 additional bedrooms, and a 3-car underground garage, in addition to a 4-car ground-level garage (7-car total). Designed for entertaining and multi-generational living, thisestate offers 3+2 bedrooms, 2 kitchens, and expansive space across 3 levels. Outdoors, enjoy professionally landscaped grounds withmanicured gardens, lush forests, extensive stonework, 2 private ponds connected by a bridge, hot tub, outdoor pizza oven, and multipleentertaining areas, creating the ultimate private retreat. A rare opportunity for the discerning buyer to own a magnificent estate property thatcombines luxury, serenity, and unmatched craftsmanship.

14180 Heritage Road, Caledon

Listing courtesy of RE/MAX SPECIALISTS TEAM SUKHVINDER.

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