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Detached properties in Caledon
Headwater Road
Sold
Sold in Oct 2026
Detached
Buyers negotiated 5.92% off asking
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Headwater Road
Listed:
$
1,249,000
Sold:
$
1,175,000
92
Headwater Road, Caledon , Bolton West
4 Beds
4 Baths
2 Garage
Royal Valley Drive
Sold
Sold in Oct 2026
Detached
Buyers negotiated 4.16% off asking
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Royal Valley Drive
Listed:
$
1,299,000
Sold:
$
1,245,000
124
Royal Valley Drive, Caledon , Rural Caledon
4 + 1 Beds
5 Baths
Glasgow Road
Sold
Sold in Oct 2026
Att/Row/Twnhouse
Buyers negotiated 1.53% off asking
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Glasgow Road
Listed:
$
979,990
Sold:
$
965,000
19-103 - 630
Glasgow Road, Caledon , Bolton West
4 Beds
3 Baths
Glasgow Road
Sold
Sold in Oct 2026
Att/Row/Twnhouse
Buyers negotiated 1.04% off asking
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Glasgow Road
Listed:
$
959,990
Sold:
$
949,990
19-100 - 624
Glasgow Road, Caledon , Bolton West
3 Beds
3 Baths
Haines Drive
Sold
Sold in Oct 2026
Detached
Buyers negotiated 14.72% off asking
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Haines Drive
Listed:
$
2,274,900
Sold:
$
1,940,000
128
Haines Drive, Caledon , Bolton East
4 + 2 Beds
5 Baths
Schaefer Place
Sold
Sold in Oct 2026
Detached
Buyers negotiated 9.53% off asking
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Schaefer Place
Listed:
$
829,000
Sold:
$
750,000
8
Schaefer Place, Caledon , Bolton North
2 + 1 Beds
2 Baths
Castlewood Court
Sold
Sold in Oct 2026
Detached
Buyers negotiated 1.65% off asking
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Castlewood Court
Listed:
$
1,398,000
Sold:
$
1,375,000
8
Castlewood Court, Caledon , Rural Caledon
4 + 1 Beds
4 Baths
Fallis Crescent
Sold
Sold in Oct 2026
Att/Row/Twnhouse
Buyers negotiated 3.11% off asking
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Fallis Crescent
Listed:
$
799,900
Sold:
$
775,000
27
Fallis Crescent, Caledon , Caledon East
4 Beds
3 Baths
Ellwood Drive W
Sold
Sold in Oct 2026
Detached
Sold at full asking price
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Ellwood Drive W
Listed:
$
899,000
Sold:
$
891,000
158
Ellwood Drive W, Caledon , Bolton West
3 + 2 Beds
2 Baths
Albert Spencer Avenue
Sold
Sold in Oct 2026
Detached
Buyers negotiated 7.90% off asking
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Albert Spencer Avenue
Listed:
$
1,379,000
Sold:
$
1,270,000
30
Albert Spencer Avenue, Caledon , Caledon East
4 + 3 Beds
7 Baths
Chapel Street
Sold
Sold in Oct 2026
Detached
Buyers negotiated 8.18% off asking
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Chapel Street
Listed:
$
599,000
Sold:
$
550,000
7
Chapel Street, Caledon , Bolton North
2 Beds
1 Baths
Sheardown Trail
Sold
Sold in Oct 2026
Detached
Buyers negotiated 3.70% off asking
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Sheardown Trail
Listed:
$
1,080,000
Sold:
$
1,040,000
9
Sheardown Trail, Caledon , Bolton East
3 + 1 Beds
4 Baths
Ironhorse Crescent
Sold
Sold in Oct 2026
Semi Detached
Buyers negotiated 2.86% off asking
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Ironhorse Crescent
Listed:
$
875,000
Sold:
$
850,000
65
Ironhorse Crescent, Caledon , Bolton West
3 Beds
4 Baths
Tanglewood Drive
Sold
Sold in Oct 2026
Detached
Buyers negotiated 1.63% off asking
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Tanglewood Drive
Listed:
$
1,499,500
Sold:
$
1,475,000
16
Tanglewood Drive, Caledon , Rural Caledon
5 + 1 Beds
7 Baths
Crestridge Drive
Sold
Sold in Oct 2026
Detached
Buyers negotiated 4.15% off asking
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Crestridge Drive
Listed:
$
939,000
Sold:
$
900,000
28
Crestridge Drive, Caledon , Bolton North
3 Beds
3 Baths
Ash Hill Avenue
Sold
Sold in Oct 2026
Detached
Sold 11.56% over asking
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Ash Hill Avenue
Listed:
$
1,299,800
Sold:
$
1,450,000
54
Ash Hill Avenue, Caledon , Caledon East
4 + 3 Beds
7 Baths
Escarpment Side Road
Sold
Sold in Oct 2026
Rural Resid
Buyers negotiated 9.29% off asking
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Escarpment Side Road
Listed:
$
2,498,000
Sold:
$
2,266,000
4845
Escarpment Side Road, Caledon , Rural Caledon
4 + 1 Beds
3 Baths
Breckonwood Street
Sold
Sold in Oct 2026
Detached
Buyers negotiated 6.82% off asking
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Breckonwood Street
Listed:
$
1,599,000
Sold:
$
1,490,000
1
Breckonwood Street, Caledon , Rural Caledon
4 + 3 Beds
6 Baths
Phyllis Drive
Sold
Sold in Oct 2026
Att/Row/Twnhouse
Buyers negotiated 1.23% off asking
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Phyllis Drive
Listed:
$
799,800
Sold:
$
790,000
47
Phyllis Drive, Caledon , Rural Caledon
3 Beds
3 Baths
Kearny Avenue
Sold
Sold in Oct 2026
Semi Detached
Buyers negotiated 2.66% off asking
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Kearny Avenue
Listed:
$
899,900
Sold:
$
876,000
27
Kearny Avenue, Caledon , Rural Caledon
3 Beds
3 Baths
Flemington Drive
Sold
Sold in Oct 2026
Att/Row/Twnhouse
Buyers negotiated 2.18% off asking
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Flemington Drive
Listed:
$
734,000
Sold:
$
718,000
20
Flemington Drive, Caledon , Rural Caledon
3 Beds
2 Baths
Cross Country Boulevard
Sold
Sold in Oct 2026
Detached
Buyers negotiated 9.46% off asking
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Cross Country Boulevard
Listed:
$
1,099,000
Sold:
$
995,000
46
Cross Country Boulevard, Caledon , Bolton North
3 Beds
3 Baths
Wishing Well Crescent N
Sold
Sold in Oct 2026
Detached
Buyers negotiated 4.26% off asking
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Wishing Well Crescent N
Listed:
$
1,269,000
Sold:
$
1,215,000
48
Wishing Well Crescent N, Caledon , Rural Caledon
5 + 1 Beds
5 Baths
Maple Cider Street
Sold
Sold in Oct 2026
Semi Detached
Buyers negotiated 4.43% off asking
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Maple Cider Street
Listed:
$
899,900
Sold:
$
860,000
64
Maple Cider Street, Caledon , Rural Caledon
3 Beds
4 Baths
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