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Rural Caledon, Caledon, ON Luxury Homes - P2

Showing results 31 - 60 of 72
Last Updated: October 04, 2026
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50 Photos
Last Updated : 24 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 : 24 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 : 24 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 : 24 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 : 26 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 : 26 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
36 Photos
Last Updated : 30 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 : 31 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
39 Photos
Last Updated : 35 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 : 35 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
32 Photos
Last Updated : 37 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
42 Photos
Last Updated : 39 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
37 Photos
Last Updated : 41 Days ago
5809 Beech Grove Side Rd Side Road, Peel, ON , MLS #W13626786 , Image - 1

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5809 Beech Grove Side Rd Side Road Rural Caledon, Caledon, Peel, ON MLS® W13626786

Residential Freehold (Rural Residential)

$9950000.0
  • 5 +4 Beds
  • 7 Baths
  • 5000 + sq-ft
Situated on a prime 46+ acre corner lot with 10,000 sq ft + custom built luxury ranch bungalow. The main house has 9 bedrooms, 7 bathrooms inclusive o
17 Photos
Last Updated : 41 Days ago
34 King Street S, Peel, ON , MLS #W12424876 , Image - 1

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34 King Street S Rural Caledon, Caledon, Peel, ON MLS® W12424876

Residential Freehold (Rural Residential)

$2750000.0
price drop iconPrice drop by 1.8%
  • 3 +1 Beds
  • 2 Baths
  • 2000-2500 sq-ft
Credit River Cottage, Belfountain. 3 bed + den, riverfront cottage with no public access street - very private. An entertainers oasis, wood burning fi
50 Photos
Last Updated : 49 Days ago
19246 Centreville Creek Road, Peel, ON , MLS #W13653982 , Image - 1

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19246 Centreville Creek Road Rural Caledon, Caledon, Peel, ON MLS® W13653982

Residential Freehold (Farm)

$5999900.0
  • 3 +2 Beds
  • 3 Baths
  • 1500-2000 sq-ft
//Spectacular **50 Acres** Country Estate Farmland Property With Stunning Views In Prestigious Rural Caledon !! Rare Opportunity To Own A Truly Pictu
1 Photos
Last Updated : 49 Days ago
13186 Airport Road E, Peel, ON
13186 Airport Road E Rural Caledon, Caledon, Peel, ON MLS® W13668634

Residential Freehold (Detached)

$2499922.0
  • 4 +1 Beds
  • 3 Baths
  • 2000-2500 sq-ft
fully upgraded (renovated), no one lived after Renovate, on Airport Rd on big lot, good size 4 bedrooms, Sep living and family rooms. Finished Basemen
49 Photos
Last Updated : 51 Days ago
446 The Grange Side Road, Peel, ON , MLS #W13646518 , Image - 1

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446 The Grange Side Road Rural Caledon, Caledon, Peel, ON MLS® W13646518

Residential Freehold (Detached)

$4750000.0
  • 3 +1 Beds
  • 5 Baths
  • 3000-3500 sq-ft
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 vi
28 Photos
Last Updated : 52 Days ago
7236 Mayfield Road, Peel, ON , MLS #W13235354 , Image - 1

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7236 Mayfield Road Rural Caledon, Caledon, Peel, ON MLS® W13235354

Residential Freehold (Detached)

$4499000.0
  • 3 +1 Beds
  • 3 Baths
  • 2000-2500 sq-ft
This Parcel is Zoned RMD-705-H49A-H49B and RMD-706-H49A-H49B with 2.365 Acres and is Located Within the Phase 1 Community Area Under the Caledon Offic
49 Photos
Last Updated : 60 Days ago
20341 St Andrews Road, Peel, ON , MLS #W13635326 , Image - 1

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20341 St Andrews Road Rural Caledon, Caledon, Peel, ON MLS® W13635326

Residential Freehold (Rural Residential)

$3200000.0
  • 2 +2 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to 20341 St. Andrews Road, Caledon-a rare country estate where exceptional outdoor living meets endless possibilities. Set on an impressive 77
27 Photos
Last Updated : 65 Days ago
7048 King Street, Peel, ON , MLS #W13621866 , Image - 1

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7048 King Street Rural Caledon, Caledon, Peel, ON MLS® W13621866

Residential Freehold (Detached)

$3199000.0
  • 7 +5 Beds
  • 6 Baths
  • 3500-5000 sq-ft
10+ acre corner property featuring TWO homes, TWO separate driveways, and frontage on TWO roads (King Street/Centreville Creek Road). Theproperty offe
50 Photos
Last Updated : 66 Days ago
4175 Beech Grove, Peel, ON , MLS #W13621500 , Image - 1

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4175 Beech Grove Rural Caledon, Caledon, Peel, ON MLS® W13621500

Residential Freehold (Detached)

$3999999.0
  • 4 +2 Beds
  • 7 Baths
  • 2000-2500 sq-ft
Welcome to an extraordinary private estate set on over 38 acres in the rolling countryside of Caledon. This rare offering combines luxury living, natu
8 Photos
Last Updated : 66 Days ago
8575 Patterson Side Road, Peel, ON , MLS #W13141784 , Image - 1

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8575 Patterson Side Road Rural Caledon, Caledon, Peel, ON MLS® W13141784

Residential Freehold (Rural Residential)

$9000000.0
  • 4 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Investment opportunity! 80 acres of land banking across from urban boundary of Palgrave. Buy and hold land. Strong potential long term for investment
1 Photos
Last Updated : 71 Days ago
12864 Innis Lake Road, Peel, ON
12864 Innis Lake Road Rural Caledon, Caledon, Peel, ON MLS® W13585468

Residential Freehold (Farm)

$13000000.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Nestled within the **Whitebelt**, this exceptional **10-acre** property presents a rare opportunity in one of the region's fastest-growing areas. Idea
42 Photos
Last Updated : 73 Days ago
15316 Mount Wolfe Road, Peel, ON , MLS #W12966534 , Image - 1

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15316 Mount Wolfe Road Rural Caledon, Caledon, Peel, ON MLS® W12966534

Residential Freehold (Detached)

$3690000.0
  • 4 +1 Beds
  • 4 Baths
  • 5000 + sq-ft
Here is your opportunity to acquire 2 houses on 52 acres in Caledon. AAA location near Bolton and Nobleton. Long views over the majestic Caledon Hills
27 Photos
Last Updated : 75 Days ago
4780 Escarpment Side Road, Peel, ON , MLS #W13589386 , Image - 1

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4780 Escarpment Side Road Rural Caledon, Caledon, Peel, ON MLS® W13589386

Residential Freehold (Detached)

$10900000.0
  • 4 +3 Beds
  • 5 Baths
  • 3000-3500 sq-ft
WOODLANDS is an extraordinary 7-bedroom, 5-bathroom estate offering two distinct residences set on approximately 63 private acres of mature forest, sc
1 Photos
Last Updated : 82 Days ago
5775 Olde Base Line Road, Peel, ON
5775 Olde Base Line Road Rural Caledon, Caledon, Peel, ON MLS® W13103560

Residential Freehold (Farm)

$5750000.0
  • 4 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Attention Developers & Investors.......Exceptional opportunity to acquire 44.74 acres in Caledon, Primely located close to Airport Road & Olde Base Li
1 Photos
Last Updated : 82 Days ago
19 Tanglewood Drive, Peel, ON
19 Tanglewood Drive Rural Caledon, Caledon, Peel, ON MLS® W13448626

Residential Freehold (Detached)

$2495000.0
  • 5 +2 Beds
  • 5 Baths
  • 5000 + sq-ft
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,14
49 Photos
Last Updated : 86 Days ago
7728 Mayfield Road, Peel, ON , MLS #W13543150 , Image - 1

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7728 Mayfield Road Rural Caledon, Caledon, Peel, ON MLS® W13543150

Residential Freehold (Detached)

$3999000.0
  • 4 Beds
  • 4 Baths
  • 3500-5000 sq-ft
Experience luxury country living with this stunning custom-built approximately over 3500 sq.ft. home in desirable community of caledon, located on May
50 Photos
Last Updated : 88 Days ago
15366 The Gore Road, Peel, ON , MLS #W13536462 , Image - 1

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15366 The Gore Road Rural Caledon, Caledon, Peel, ON MLS® W13536462

Residential Freehold (Farm)

$7000000.0
  • 3 +1 Beds
  • 2 Baths
  • 2000-2500 sq-ft
Welcome to this exceptional 96-acre farm estate, offering a rare combination of natural beauty, functionality, and long-term potential. Framed by swee
11 Photos
Last Updated : 89 Days ago
5232 Mayfield Road, Peel, ON , MLS #W13527180 , Image - 1

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5232 Mayfield Road Rural Caledon, Caledon, Peel, ON MLS® W13527180

Residential Freehold (Detached)

$12999999.0
  • 4 Beds
  • 2 Baths
  • 2000-2500 sq-ft
Calling All Developers! An exceptional opportunity to acquire approximately 9.92 acres of prime land with 229.56 feet of frontage, identified within
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