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Caledon, ON Luxury Homes - P2

Showing results 31 - 60 of 114
Last Updated: September 27, 2026
  • New Listings
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50 Photos
Last Updated : 9 Days ago
16735 Shaws Creek Road, Peel, ON , MLS #W13804054 , Image - 1
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16735 Shaws Creek Road Rural Caledon, Caledon, Peel, ON MLS® W13804054

Residential Freehold (Detached)

$4699000.0
  • 3 +2 Beds
  • 8 Baths
  • 3500-5000 sq-ft
This executive-quality estate offers five-star quality and a year-round Muskoka environment without the travel, situated in the finest areas of Caledo
50 Photos
Last Updated : 9 Days ago
20 Stinson Street, Peel, ON , MLS #W13210558 , Image - 1

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20 Stinson Street Palgrave, Caledon, Peel, ON MLS® W13210558

Residential Freehold (Detached)

$3799000.0
  • 5 +1 Beds
  • 7 Baths
  • 5000 + sq-ft
Exquisite Custom-Built Luxury Estate Situated On A Private 2-Acre Lot In Prestigious Palgrave, Offering Breathtaking Views And Unmatched Privacy. Buil
48 Photos
Last Updated : 11 Days ago
20 Buckstown Trail, Peel, ON , MLS #W13650024 , Image - 1

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20 Buckstown Trail Palgrave, Caledon, Peel, ON MLS® W13650024

Residential Freehold (Detached)

$2199999.0
price drop iconPrice drop by 12.0%
  • 3 Beds
  • 3 Baths
  • 2000-2500 sq-ft
First time offered! Nestled in one of Palgrave's most sought-after enclaves, this exceptional 3-bedroom plus den custom-built bungalow sits on a premi
50 Photos
Last Updated : 11 Days ago
15520 Horseshoe Hill Road, Peel, ON , MLS #W13558786 , Image - 1

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15520 Horseshoe Hill Road Rural Caledon, Caledon, Peel, ON MLS® W13558786

Residential Freehold (Detached)

$5399000.0
price drop iconPrice drop by 6.9%
  • 4 +1 Beds
  • 6 Baths
  • 3500-5000 sq-ft
Welcome to your private retreat, an extraordinary estate where sophisticated design, impeccable craftsmanship and exceptional functionality come toget
50 Photos
Last Updated : 11 Days ago
2814 Forks Of The Credit Road, Peel, ON , MLS #W13776868 , Image - 1

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2814 Forks Of The Credit Road Rural Caledon, Caledon, Peel, ON MLS® W13776868

Residential Freehold (Detached)

$2468000.0
  • 4 +1 Beds
  • 6 Baths
  • 2000-2500 sq-ft
Welcome to a one-of-a-kind longevity estate where nature, privacy & wellness-focused design converge on 2.71 picturesque acres. Ideally located near t
46 Photos
Last Updated : 16 Days ago
14902 Mount Pleasant Road, Peel, ON , MLS #W13771366 , Image - 1

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14902 Mount Pleasant Road Rural Caledon, Caledon, Peel, ON MLS® W13771366

Residential Freehold (Detached)

$2800000.0
  • 3 +2 Beds
  • 5 Baths
  • 5000 + sq-ft
Set on approximately 15.8 picturesque acres in scenic Caledon, this exceptional multi-residential country estate offers an outstanding combination of
50 Photos
Last Updated : 16 Days ago
84 Kennedy Road, Peel, ON , MLS #W13771530 , Image - 1

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84 Kennedy Road Cheltenham, Caledon, Peel, ON MLS® W13771530

Residential Freehold (Detached)

$2899000.0
  • 5 +1 Beds
  • 6 Baths
  • 5000 + sq-ft
Timeless elegance meets impeccable craftsmanship in this stunning Cheltenham estate. A rare find, this beautifully built 5+1 bed, 6 bath home in the s
50 Photos
Last Updated : 17 Days ago
3285 Beech Grove Side Road, Peel, ON , MLS #W13767138 , Image - 1

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3285 Beech Grove Side Road Rural Caledon, Caledon, Peel, ON MLS® W13767138

Residential Freehold (Detached)

$3450000.0
  • 5 +1 Beds
  • 5 Baths
  • 3500-5000 sq-ft
The Beech House stands well back on 2.55 wooded acres, screened from the road. A modern house of more than 4,000 square feet, rebuilt from the studs o
39 Photos
Last Updated : 17 Days ago
13905 Kennedy Road, Peel, ON , MLS #W13768554 , Image - 1

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13905 Kennedy Road Rural Caledon, Caledon, Peel, ON MLS® W13768554

Residential Freehold (Detached)

$2499000.0
  • 4 Beds
  • 4 Baths
  • 3500-5000 sq-ft
Escape to a home that truly understands the meaning of space. Situated on an expansive lot, this custom-built masterpiece offers over 3,500 square fee
50 Photos
Last Updated : 17 Days ago
18250 Duffy's Lane, Peel, ON , MLS #W13601824 , Image - 1

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18250 Duffy's Lane Palgrave, Caledon, Peel, ON MLS® W13601824

Residential Freehold (Detached)

$5499000.0
  • 3 +1 Beds
  • 4 Baths
  • 5000 + sq-ft
Extraordinary Palgrave estate where privacy, a tranquil setting, natural beauty, and endless opportunity come together on approximately 86 spectacular
50 Photos
Last Updated : 17 Days ago
16927 Winston Churchill Boulevard, Peel, ON , MLS #W13224014 , Image - 1

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16927 Winston Churchill Boulevard Rural Caledon, Caledon, Peel, ON MLS® W13224014

Residential Freehold (Detached)

$4200000.0
price drop iconPrice drop by 6.7%
  • 4 +1 Beds
  • 3 Baths
  • 2500-3000 sq-ft
A Victorian reimagined, complete with a secret English garden. Just outside Belfountain, on nearly 15 acres of Caledon countryside, it is steeped in c
50 Photos
Last Updated : 17 Days ago
3045 Highpoint Side Road, Peel, ON , MLS #W13761544 , Image - 1

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3045 Highpoint Side Road Rural Caledon, Caledon, Peel, ON MLS® W13761544

Residential Freehold (Detached)

$3950000.0
  • 4 +2 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Among the finest homes in Caledon. Set high on a hill across nearly 14 acres, surrounded by mature forest, where wild English gardens meet the clean,
48 Photos
Last Updated : 17 Days ago
15668 Shaws Creek Road, Peel, ON , MLS #W13766840 , Image - 1

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15668 Shaws Creek Road Rural Caledon, Caledon, Peel, ON MLS® W13766840

Residential Freehold (Detached)

$3200000.0
  • 4 Beds
  • 3 Baths
  • 3500-5000 sq-ft
Set on 43+ acres with mature trees, open lawns, perennial and vegetable gardens, flagstone patios, and a large stream-fed pond, this exceptional count
44 Photos
Last Updated : 18 Days ago
16 Mccoll Drive, Peel, ON , MLS #W13682252 , Image - 1

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16 Mccoll Drive Rural Caledon, Caledon, Peel, ON MLS® W13682252

Residential Freehold (Detached)

$2380000.0
  • 3 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Set on a Gorgeous 2.5-acre property, this fully gated, 3 bedroom estate home offers privacy & serenity - impeccably landscaped, nicely treed & cared f
50 Photos
Last Updated : 18 Days ago
13 Doctor Reynar Road, Peel, ON , MLS #W13762806 , Image - 1

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13 Doctor Reynar Road Palgrave, Caledon, Peel, ON MLS® W13762806

Residential Freehold (Detached)

$2299999.0
  • 3 +1 Beds
  • 5 Baths
  • 2500-3000 sq-ft
A masterfully designed turnkey estate in prestigious Palgrave, this exceptional residence embodies timeless elegance and uncompromising luxury while o
39 Photos
Last Updated : 18 Days ago
2097 Grange Side Road, Peel, ON , MLS #W13573998 , Image - 1

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2097 Grange Side Road Rural Caledon, Caledon, Peel, ON MLS® W13573998

Residential Freehold (Detached)

$7600000.0
  • 8 +1 Beds
  • 9 Baths
  • 5000 + sq-ft
One of Caledon's Most Spectacular Estates with Breathtaking Views of the Caledon Landscape and Toronto Skyline, this estate is the epitome of luxury l
50 Photos
Last Updated : 19 Days ago
1 Edgewild Drive, Peel, ON , MLS #W13563592 , Image - 1

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1 Edgewild Drive Palgrave, Caledon, Peel, ON MLS® W13563592

Residential Freehold (Detached)

$3149000.0
  • 3 +2 Beds
  • 5 Baths
  • 3500-5000 sq-ft
An extraordinary custom built residence situated on one of Caledon's most prestigious and sought-after streets. This home showcases superior craftsman
50 Photos
Last Updated : 19 Days ago
18387 The Gore Road, Peel, ON , MLS #W13756116 , Image - 1

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18387 The Gore Road Rural Caledon, Caledon, Peel, ON MLS® W13756116

Residential Freehold (Detached)

$5995000.0
  • 3 +2 Beds
  • 5 Baths
  • 5000 + sq-ft
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
36 Photos
Last Updated : 19 Days ago
8339 Finnerty Side Road, Peel, ON , MLS #W13754322 , Image - 1

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8339 Finnerty Side Road Rural Caledon, Caledon, Peel, ON MLS® W13754322

Residential Freehold (Detached)

$2099999.0
  • 3 +2 Beds
  • 5 Baths
  • 2500-3000 sq-ft
Set amidst 25 acres of serene, wooded landscape backing onto conservation land, this exceptional raised bungalow offers over 5,800 sq. ft. of refined
50 Photos
Last Updated : 22 Days ago
14728 Heritage Road, Peel, ON , MLS #W13749034 , Image - 1

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14728 Heritage Road Rural Caledon, Caledon, Peel, ON MLS® W13749034

Residential Freehold (Detached)

$2174900.0
  • 4 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Luxury Meets Nature A Private 29.5-Acre Retreat in Terra Cotta. Experience the perfect fusion of countryside tranquility and modern luxury in this stu
36 Photos
Last Updated : 23 Days ago
2236 Boston Mills Road, Peel, ON , MLS #W13746004 , Image - 1

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2236 Boston Mills Road Rural Caledon, Caledon, Peel, ON MLS® W13746004

Residential Freehold (Detached)

$2800000.0
  • 4 Beds
  • 4 Baths
  • 3500-5000 sq-ft
Set on ~12.7 acres with a highly desired location, this beautifully maintained country property offers a rare blend of privacy, vista views, natural b
49 Photos
Last Updated : 24 Days ago
2049 Highpoint Side Road, Peel, ON , MLS #W13122204 , Image - 1

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2049 Highpoint Side Road Rural Caledon, Caledon, Peel, ON MLS® W13122204

Residential Freehold (Detached)

$3788888.0
  • 3 +1 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Welcome to this extraordinary custom-built bungalow nestled on 25 clear acres, offering over 5,500 sq. ft. of luxurious living space plus a remarkable
32 Photos
Last Updated : 25 Days ago
17218 Innis Lake Road, Peel, ON , MLS #W13206596 , Image - 1

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17218 Innis Lake Road Caledon East, Caledon, Peel, ON MLS® W13206596

Residential Freehold (Vacant Land)

$2250000.0
Exceptional 50-acre parcel of land with potential for your dream custom home build, minutes to town. This idyllic country setting offers westerly view
48 Photos
Last Updated : 27 Days ago
7 Dolan Drive, Peel, ON , MLS #W13570924 , Image - 1

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7 Dolan Drive Palgrave, Caledon, Peel, ON MLS® W13570924

Residential Freehold (Detached)

$2375000.0
  • 5 Beds
  • 7 Baths
  • 3500-5000 sq-ft
Welcome to 7 Dolan Drive, an exceptional executive estate in the heart of picturesque Palgrave. Offering nearly 5,000 sq. ft. of luxurious living spac
39 Photos
Last Updated : 28 Days ago
18137 Cataract Road, Peel, ON , MLS #W13718408 , Image - 1

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18137 Cataract Road Rural Caledon, Caledon, Peel, ON MLS® W13718408

Residential Freehold (Duplex)

$2999900.0
  • 7 +2 Beds
  • 6 Baths
  • 3500-5000 sq-ft
This is the one you've been waiting for! Enjoy the best of country living without the hassle of renovations. Completely transformed from the studs out
47 Photos
Last Updated : 28 Days ago
12792 Humber Station Road, Peel, ON , MLS #W13597554 , Image - 1

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12792 Humber Station Road Rural Caledon, Caledon, Peel, ON MLS® W13597554

Residential Freehold (Detached)

$2450000.0
price drop iconPrice drop by 3.9%
  • 3 +2 Beds
  • 3 Baths
  • 2500-3000 sq-ft
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 r
50 Photos
Last Updated : 30 Days ago
86 Willow Street, Peel, ON , MLS #W13445982 , Image - 1

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86 Willow Street Bolton East, Caledon, Peel, ON MLS® W13445982

Residential Freehold (Detached)

$2488000.0
  • 4 Beds
  • 5 Baths
  • 3500-5000 sq-ft
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
32 Photos
Last Updated : 30 Days ago
15910 Mississauga Road, Peel, ON , MLS #W13701498 , Image - 1

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15910 Mississauga Road Rural Caledon, Caledon, Peel, ON MLS® W13701498

Residential Freehold (Detached)

$2950000.0
  • 3 +2 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Pond Farm, Caledon. Conveniently located on the west side of Mississauga Road, just south of Caledon's, The Grange Sideroad is this 57-acre original c
40 Photos
Last Updated : 31 Days ago
255 Amos Drive, Peel, ON , MLS #W13629928 , Image - 1

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255 Amos Drive Palgrave, Caledon, Peel, ON MLS® W13629928

Residential Freehold (Detached)

$2499900.0
  • 4 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Set in the prestigious neighborhood of Palgrave, this exceptional 4,000 sq ft residence is a masterclass in luxury living and refined design. Surround
42 Photos
Last Updated : 32 Days ago
19728 Kennedy Road, Peel, ON , MLS #W13003888 , Image - 1

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19728 Kennedy Road Rural Caledon, Caledon, Peel, ON MLS® W13003888

Residential Freehold (Detached)

$2200000.0
price drop iconPrice drop by 3.9%
  • 3 +1 Beds
  • 4 Baths
  • 2500-3000 sq-ft
This elegant bungalow has everything today's buyer could wish for-beautifully finished and move-in ready. Behind striking double iron gates, the full
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