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Rural Caledon, Caledon, ON Luxury Homes

Showing results 1 - 30 of 72

With Square Yards Canada, you can find your dream luxury homes for sale in Rural Caledon. Explore your options from condo apartments, condo townhouses, detached houses, semi detached homes posted by agencies/owners who provide spacious and luxurious amenities in luxury houses for sale in Rural Caledon


Last Updated: October 04, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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50 Photos
Last Updated : 1 Day 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
32 Photos
Last Updated : 1 Day ago
7190 King Street, Peel, ON , MLS #W13616516 , Image - 1

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7190 King Street Rural Caledon, Caledon, Peel, ON MLS® W13616516

Residential Freehold (Detached)

$2900000.0
  • 4 +2 Beds
  • 4 Baths
  • 2000-2500 sq-ft
**Excellent opportunity** to acquire 10.45 acres in a prime location of Caledon offering endless possibilities, located close to King St and The Gore
Open House : Sun Oct 04, 01:00 PM to 05:00 PM
50 Photos
Last Updated : 2 Days ago
7 Proctor Avenue, Peel, ON , MLS #W13814062 , Image - 1

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7 Proctor Avenue Rural Caledon, Caledon, Peel, ON MLS® W13814062

Residential Freehold (Detached)

$2595000.0
  • 4 +1 Beds
  • 6 Baths
  • 3500-5000 sq-ft
Set amidst the natural beauty & privacy of prestigious Millcreek Estates, this exceptional 2-storey estate offers an extraordinary 2.74-Acre setting i
1 Photos
Last Updated : 3 Days ago
38 Gentle Fox Drive, Peel, ON
38 Gentle Fox Drive Rural Caledon, Caledon, Peel, ON MLS® W13841560

Residential Freehold (Detached)

$2188000.0
  • 5 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Welcome to 38 Gentle Fox Drive, a luxurious Caledon residence offering over 4,000 sq. ft. of space designed for both everyday comfort and memorable en
Open House : Sun Oct 04, 01:00 PM to 03:00 PM
49 Photos
Last Updated : 3 Days ago
4845 Escarpment Side Road, Peel, ON , MLS #W13764100 , Image - 1

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4845 Escarpment Side Road Rural Caledon, Caledon, Peel, ON MLS® W13764100

Residential Freehold (Rural Residential)

$2498000.0
  • 4 +1 Beds
  • 3 Baths
  • 2500-3000 sq-ft
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
39 Photos
Last Updated : 3 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 : 3 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
2 Photos
Last Updated : 4 Days ago
0 Beech Grove Side Road, Peel, ON , MLS #W13832910 , Image - 1
0 Beech Grove Side Road Rural Caledon, Caledon, Peel, ON MLS® W13832910

Residential Freehold (Vacant Land)

$2799000.0
**Not For Everyone-And That Is Precisely The Point.** For Those With The Vision And Means To Create Something Truly Exceptional, This Remarkable 103-A
21 Photos
Last Updated : 5 Days ago
7191 Castlederg Side Road, Peel, ON , MLS #W13836708 , Image - 1

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7191 Castlederg Side Road Rural Caledon, Caledon, Peel, ON MLS® W13836708

Residential Freehold (Detached)

$3488000.0
  • 4 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Welcome to an exceptional 10 acre property offering the perfect blend of residential comfort and versatile workspace. This spacious 4 bedroom bungalow
50 Photos
Last Updated : 5 Days ago
17711 Humber Station Road, Peel, ON , MLS #W13808446 , Image - 1

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17711 Humber Station Road Rural Caledon, Caledon, Peel, ON MLS® W13808446

Residential Freehold (Detached)

$3399999.0
  • 6 Beds
  • 4 Baths
  • 3500-5000 sq-ft
THIS SPECTACULAR NEWLY CUSTOM BUILT FAMILY ESTATE HOME OFFERS 4800 SQ FT OF LUXURIOUS ABOVE GRADE LIVING SPACE. DESIGNED FOR BOTH GRAND-SCALE ENTERTAI
Open House : Sun Oct 04, 12:00 PM to 03:00 PM
44 Photos
Last Updated : 6 Days ago
27 Cedar Drive, Peel, ON , MLS #W13822806 , Image - 1

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27 Cedar Drive Rural Caledon, Caledon, Peel, ON MLS® W13822806

Residential Freehold (Detached)

$2225000.0
  • 5 Beds
  • 3 Baths
  • 3000-3500 sq-ft
Magnificent Georgian Estate in Prestigious Caledon! Welcome to an extraordinary 5-bedroom, 3-bathroom Georgian fieldstone estate on 2.6 private acres,
Open House : Sun Oct 04, 01:00 PM to 03:00 PM
45 Photos
Last Updated : 6 Days ago
23 Granite Stones Drive, Peel, ON , MLS #W13670564 , Image - 1

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23 Granite Stones Drive Rural Caledon, Caledon, Peel, ON MLS® W13670564

Residential Freehold (Detached)

$2150000.0
price drop iconPrice drop by 4.4%
  • 4 Beds
  • 6 Baths
  • 3000-3500 sq-ft
A rare offering on Granite Stones. Set on 2.5 acres, this updated log home is beautifully positioned within its natural surroundings, well back from t
18 Photos
Last Updated : 8 Days ago
18584 The Gore Road, Peel, ON , MLS #W13827282 , Image - 1

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18584 The Gore Road Rural Caledon, Caledon, Peel, ON MLS® W13827282

Residential Freehold (Detached)

$2400000.0
  • 5 Beds
  • 4 Baths
  • 3000-3500 sq-ft
One Of Caledon's Most Scenic, Stunning Properties. Set Privately, Bordered By Mature Trees & Forest Yet Open To The 28 Acres Of Rolling Hills & Trails
46 Photos
Last Updated : 9 Days ago
11 Prince Andrew Drive, Peel, ON , MLS #W13747140 , Image - 1

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11 Prince Andrew Drive Rural Caledon, Caledon, Peel, ON MLS® W13747140

Residential Freehold (Detached)

$2144000.0
  • 4 +1 Beds
  • 4 Baths
  • 3500-5000 sq-ft
Timeless Character, Exceptional Space & 2 Acres of Privacy. Discover the possibilities in this stately, all-brick residence, thoughtfully designed and
33 Photos
Last Updated : 9 Days ago
15191 Airport Road, Peel, ON , MLS #W13827252 , Image - 1

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15191 Airport Road Rural Caledon, Caledon, Peel, ON MLS® W13827252

Residential Freehold (Detached)

$2599000.0
  • 3 +2 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome to this incredible meticulously kept and built residence (2005) situated on a sprawling, private 1-acre lot! Offering unmatched versatility, t
50 Photos
Last Updated : 9 Days ago
13289 Innis Lake Road, Peel, ON , MLS #W13462682 , Image - 1

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13289 Innis Lake Road Rural Caledon, Caledon, Peel, ON MLS® W13462682

Residential Freehold (Detached)

$8000000.0
  • 4 +1 Beds
  • 5 Baths
  • 2500-3000 sq-ft
Exceptional 10-acre country estate offering privacy, versatility, and outstanding lifestyle amenities. This spacious 2-storey brick home features a re
49 Photos
Last Updated : 9 Days ago
15 Caledon Mountain Drive, Peel, ON , MLS #W13768664 , Image - 1

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15 Caledon Mountain Drive Rural Caledon, Caledon, Peel, ON MLS® W13768664

Residential Freehold (Detached)

$2795000.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
No need for AI embellishment here! This one-of-a-kind, 3.3 acre country retreat located just outside the quaint hamlet of Belfountain is pretty perfec
43 Photos
Last Updated : 9 Days ago
16089 Shaws Creek Road, Peel, ON , MLS #W13827304 , Image - 1

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16089 Shaws Creek Road Rural Caledon, Caledon, Peel, ON MLS® W13827304

Residential Freehold (Detached)

$3495000.0
  • 3 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Stunning Restored Victorian Farmhouse on 57 Private Acres with Barn & TrailsOriginally built in 1860 by the McEachern family, this Grand Victorian far
43 Photos
Last Updated : 10 Days ago
18785 The Gore Road, Peel, ON , MLS #W13565596 , Image - 1

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18785 The Gore Road Rural Caledon, Caledon, Peel, ON MLS® W13565596

Residential Freehold (Detached)

$4750000.0
  • 5 +1 Beds
  • 7 Baths
  • 5000 + sq-ft
Now Offered at $4,750,000. A rare opportunity in Caledon's prestigious luxury estate market, this exceptional custom residence has been strategically
38 Photos
Last Updated : 10 Days ago
20855 Shaws Creek Road, Peel, ON , MLS #W13577360 , Image - 1

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20855 Shaws Creek Road Rural Caledon, Caledon, Peel, ON MLS® W13577360

Residential Freehold (Detached)

$2395000.0
price drop iconPrice drop by 14.3%
  • 3 +1 Beds
  • 3 Baths
  • 2500-3000 sq-ft
50 acres - Exceptional country farm and retreat in the Heart of Caledon. Set along picturesque Shaws Creek Road, this beautifully renovated country pr
50 Photos
Last Updated : 11 Days ago
1749 Station Road, Peel, ON , MLS #W13114550 , Image - 1

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1749 Station Road Rural Caledon, Caledon, Peel, ON MLS® W13114550

Residential Freehold (Detached)

$2499000.0
price drop iconPrice drop by 10.4%
  • 4 +2 Beds
  • 5 Baths
  • 3000-3500 sq-ft
Beautiful Bungalow with amazing views! A rare find, this custom built home in the sought-after Cheltenham community offers 3200sq ft upstairs and ano
28 Photos
Last Updated : 12 Days ago
21170 Shaws Creek Road, Peel, ON , MLS #W13687636 , Image - 1

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21170 Shaws Creek Road Rural Caledon, Caledon, Peel, ON MLS® W13687636

Residential Freehold (Rural Residential)

$2389000.0
price drop iconPrice drop by 7.7%
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Acres of Fertile Land & Country Living in Caledon. Escape to your own slice of rural paradise, just south of Orangeville. This 92-acre property offers
47 Photos
Last Updated : 13 Days ago
7 Maple Meadow Court, Peel, ON , MLS #W13744042 , Image - 1

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7 Maple Meadow Court Rural Caledon, Caledon, Peel, ON MLS® W13744042

Residential Freehold (Detached)

$5250000.0
  • 4 +1 Beds
  • 7 Baths
  • 5000 + sq-ft
A rare offering in Caledon Mountain Estates on 2.8 acres, this newly built contemporary estate pairs exceptional scale and sophisticated design with a
25 Photos
Last Updated : 13 Days ago
17300 St. Andrews Road, Peel, ON , MLS #W13235950 , Image - 1

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17300 St. Andrews Road Rural Caledon, Caledon, Peel, ON MLS® W13235950

Residential Freehold (Rural Residential)

$5750000.0
  • 2 +3 Beds
  • 6 Baths
  • 5000 + sq-ft
Golf Fairways, 17300 St. Andrews Road, Caledon. Paintbrush Golf Course - Perched on a hill, south of the Escarpment Side Road is a stunning 25-acre co
22 Photos
Last Updated : 15 Days ago
14130 Creditview Road, Peel, ON , MLS #W13601720 , Image - 1

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14130 Creditview Road Rural Caledon, Caledon, Peel, ON MLS® W13601720

Residential Freehold (Vacant Land)

$4800000.0
Situated at the intersection of King Road and Creditview Road, and neighbouring the highly sought-after and picturesque village of Cheltenham Village,
50 Photos
Last Updated : 17 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 : 17 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 : 22 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 : 23 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 : 23 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
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