✨ Luxury ($2M+) in Caledon

Luxury Homes for Sale in Caledon

High-end custom builds, acreage properties, and executive homes. Browse real-time MLS® listings, updated every 15 minutes with complete photo galleries and price histories.

Active Listings36Properties available
🔥 Price Drops🏡 Bungalows🏘️ Townhouses🏰 Detached Homes🏢 Condos💰 Under $800k🏷️ Under $750k🎯 Under $1M✨ Luxury ($2M+)🔑 In-Law Suites🔨 Fixer-Uppers🏊 Inground & Heated Pools🌊 Waterfront & Views🏢 Multi-Family & Duplex🏗️ New Construction
Residential Freehold for sale - 5 Bed, 6 Bath Home at 2814 Forks Of The Credit Road Caledon ON listed at $2,468,000 (MLS# W13776868)
Added 4 days ago
$2,468,000
5bd
6ba
Residential Freehold

2814 Forks Of The Credit Road, Caledon

Sep 12, 2026
DOM: 5

Discover a truly unique and breathtaking country estate where nature, privacy, and exceptional desig...

MLS#: W13776868
For Sale
Residential Freehold for sale - 6 Bed, 6 Bath Home at 84 Kennedy Road Caledon ON listed at $2,899,000 (MLS# W13771530)
Added 5 days ago
$2,899,000
6bd
6ba
Residential Freehold

84 Kennedy Road, Caledon

Sep 11, 2026
DOM: 6

Timeless elegance meets impeccable craftsmanship in this stunning Cheltenham estate. A rare find, th...

MLS#: W13771530
For Sale
Residential Freehold for sale - 5 Bed, 5 Bath Home at 14902 Mount Pleasant Road Caledon ON listed at $2,800,000 (MLS# W13771366)
Added 5 days ago
$2,800,000
5bd
5ba
Residential Freehold

14902 Mount Pleasant Road, Caledon

Sep 11, 2026
DOM: 6

Set on approximately 15.8 picturesque acres in scenic Caledon, this exceptional multi-residential co...

MLS#: W13771366
For Sale
Residential Freehold for sale - 4 Bed, 3 Bath Home at 15 Caledon Mountain Drive Caledon ON listed at $2,795,000 (MLS# W13768664)
Added 6 days ago
$2,795,000
4bd
3ba
Residential Freehold

15 Caledon Mountain Drive, Caledon

Sep 10, 2026
DOM: 7

Welcome to 15 Caledon Mountain Drive, a one-of-a-kind, turn-key, country retreat set on 3.3 private ...

MLS#: W13768664
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 13905 Kennedy Road Caledon ON listed at $2,499,000 (MLS# W13768554)
Added 6 days ago
$2,499,000
4bd
4ba
Residential Freehold

13905 Kennedy Road, Caledon

Sep 10, 2026
DOM: 7

Escape to a home that truly understands the meaning of "space." Situated on an expansive lot, this c...

MLS#: W13768554
For Sale
Residential Freehold for sale - 5 Bed, 3 Bath Home at 4845 Escarpment Side Road Caledon ON listed at $2,498,000 (MLS# W13764100)
Added 7 days ago
$2,498,000
5bd
3ba
Residential Freehold

4845 Escarpment Side Road, Caledon

Sep 9, 2026
DOM: 8

Private 24.9 acres across from the Paintbrush Golf Course, positioned high on Caledon's Escarpment, ...

MLS#: W13764100
For Sale
Residential Freehold for sale - 4 Bed, 5 Bath Home at 13 Doctor Reynar Road Caledon ON listed at $2,299,999 (MLS# W13762806)
Added 7 days ago
$2,299,999
4bd
5ba
Residential Freehold

13 Doctor Reynar Road, Caledon

Sep 9, 2026
DOM: 8

A masterfully designed turnkey estate in prestigious Palgrave, this exceptional residence embodies t...

MLS#: W13762806
For Sale
Residential Freehold for sale - 5 Bed, 5 Bath Home at 18387 The Gore Road Caledon ON listed at $5,995,000 (MLS# W13756116)
Added 8 days ago
$5,995,000
5bd
5ba
Residential Freehold

18387 The Gore Road, Caledon

Sep 8, 2026
DOM: 9

Discover That Form A Private Paradise, This Stunning Property Boasts Over 10,000 Square Feet Of Gorg...

MLS#: W13756116
For Sale
Residential Freehold for sale - 6 Bed, 5 Bath Home at 4 Tranquility Court Caledon ON listed at $2,049,000 (MLS# W13753596)
Added 8 days ago
$2,049,000
6bd
5ba
Residential Freehold

4 Tranquility Court, Caledon

Sep 8, 2026
DOM: 9

Welcome to this private country retreat offering peaceful 2.6 acres of rural living, flexible space,...

MLS#: W13753596
For Sale
Residential Freehold for sale - 4 Bed, 3 Bath Home at 14728 Heritage Road Caledon ON listed at $2,174,900 (MLS# W13749034)
Added 11 days ago
$2,174,900
4bd
3ba
Residential Freehold

14728 Heritage Road, Caledon

Sep 5, 2026
DOM: 12

Luxury Meets Nature A Private 29.5-Acre Retreat in Terra Cotta. Experience the perfect fusion of cou...

MLS#: W13749034
For Sale
Residential Freehold for sale - 5 Bed, 4 Bath Home at 11 Prince Andrew Drive Caledon ON listed at $2,144,000 (MLS# W13747140)
Added 12 days ago
$2,144,000
5bd
4ba
Residential Freehold

11 Prince Andrew Drive, Caledon

Sep 4, 2026
DOM: 13

Timeless Character, Exceptional Space & 2 Acres of Privacy. Discover the possibilities in this state...

MLS#: W13747140
For Sale
Commercial for sale - 0 Bed, 3 Bath Home at 780 Hardwick Road Caledon ON listed at $5,999,700 (MLS# W13747802)
Added 12 days ago
$5,999,700
0bd
3ba
Commercial

780 Hardwick Road, Caledon

Sep 4, 2026
DOM: 13

Amazing opportunity to own this freestanding industrial building situated on an impressive 100-foot...

MLS#: W13747802
For Sale
Commercial for sale - 0 Bed, 3 Bath Home at 780 Hardwick Road Caledon ON listed at $2,000,000 (MLS# W13747798)
Added 12 days ago
$2,000,000
0bd
3ba
Commercial

780 Hardwick Road, Caledon

Sep 4, 2026
DOM: 13

Excellent opportunity to own a profitable and very well established business operating under the sam...

MLS#: W13747798
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 2236 Boston Mills Road Caledon ON listed at $2,800,000 (MLS# W13746004)
Added 12 days ago
$2,800,000
4bd
4ba
Residential Freehold

2236 Boston Mills Road, Caledon

Sep 4, 2026
DOM: 13

Set on ~12.7 acres with a highly desired location, this beautifully maintained country property offe...

MLS#: W13746004
For Sale
Residential Freehold for sale - 5 Bed, 7 Bath Home at 7 Maple Meadow Court Caledon ON listed at $5,250,000 (MLS# W13744042)
Added 13 days ago
$5,250,000
5bd
7ba
Residential Freehold

7 Maple Meadow Court, Caledon

Sep 3, 2026
DOM: 14

A rare offering in Caledon Mountain Estates on 2.8 acres, this newly built contemporary estate pairs...

MLS#: W13744042
For Sale
Commercial for sale - 0 Bed, 0 Bath Home at 14 Wheeler Drive Caledon ON listed at $3,999,900 (MLS# W13743854)
Added 13 days ago
$3,999,900
0bd
0ba
Commercial

14 Wheeler Drive, Caledon

Sep 3, 2026
DOM: 14

are investment opportunity to acquire approximately 43,863 sq. ft. (1.007 acres) of fenced industria...

MLS#: W13743854
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 4 Ingleview Drive Caledon ON listed at $2,250,000 (MLS# W13722256)
$2,250,000
4bd
4ba
Residential Freehold

4 Ingleview Drive, Caledon

Aug 28, 2026
DOM: 20

Luxurious Caledon escape awaits in this executive home. Refined country living meets exceptional con...

MLS#: W13722256
For Sale
Commercial for sale - 0 Bed, 0 Bath Home at 0 Mayfield Road Caledon ON listed at $4,200,000 (MLS# W13718952)
$4,200,000
0bd
0ba
Commercial

0 Mayfield Road, Caledon

Aug 27, 2026
DOM: 21

Prime 2.673 Acre parcel located on the Northwest corner of Innis Lake Rd. and Mayfield Rd., located ...

MLS#: W13718952
For Sale
Residential Freehold for sale - 9 Bed, 6 Bath Home at 18137 Cataract Road Caledon ON listed at $2,999,900 (MLS# W13718408)
$2,999,900
9bd
6ba
Residential Freehold

18137 Cataract Road, Caledon

Aug 27, 2026
DOM: 21

This is the one you've been waiting for! Enjoy the best of country living without the hassle of reno...

MLS#: W13718408
For Sale
Residential Freehold for sale - 6 Bed, 6 Bath Home at 6 Country Lane Drive Caledon ON listed at $2,299,000 (MLS# W13715192)
$2,299,000
6bd
6ba
Residential Freehold

6 Country Lane Drive, Caledon

Aug 26, 2026
DOM: 22

This Custom-Built Caledon Estate Sitting On 3.74 Acres Of Manicured Grounds, Offering Unmatched Priv...

MLS#: W13715192
For Sale
Residential Freehold for sale - 0 Bed, 0 Bath Home at 16114 Airport Road Caledon ON listed at $9,800,000 (MLS# W13700336)
$9,800,000
0bd
0ba
Residential Freehold

16114 Airport Road, Caledon

Aug 21, 2026
DOM: 27

This exceptional 10-acre development parcel presents a rare opportunity in the heart of Caledon East...

MLS#: W13700336
For Sale
Commercial for sale - 0 Bed, 0 Bath Home at 16114 Airport Road Caledon ON listed at $9,800,000 (MLS# W13700330)
$9,800,000
0bd
0ba
Commercial

16114 Airport Road, Caledon

Aug 21, 2026
DOM: 27

This exceptional 10-acre development parcel presents a rare opportunity in the heart of Caledon East...

MLS#: W13700330
For Sale
Residential Freehold for sale - 5 Bed, 4 Bath Home at 15910 Mississauga Road Caledon ON listed at $2,950,000 (MLS# W13701498)
$2,950,000
5bd
4ba
Residential Freehold

15910 Mississauga Road, Caledon

Aug 20, 2026
DOM: 28

Pond Farm, Caledon. Conveniently located on the west side of Mississauga Road, just south of Caledon...

MLS#: W13701498
For Sale
Residential Freehold for sale - 3 Bed, 2 Bath Home at 21170 Shaws Creek Road Caledon ON listed at $2,389,000 (MLS# W13687636)
Price Change
$2,389,000
3bd
2ba
Residential Freehold

21170 Shaws Creek Road, Caledon

Aug 18, 2026
DOM: 30

Acres of Fertile Land & Country Living in Caledon. Escape to your own slice of rural paradise, just ...

MLS#: W13687636
For Sale
Residential Freehold for sale - 3 Bed, 4 Bath Home at 16 Mccoll Drive Caledon ON listed at $2,380,000 (MLS# W13682252)
$2,380,000
3bd
4ba
Residential Freehold

16 Mccoll Drive, Caledon

Aug 17, 2026
DOM: 31

Set on a Gorgeous 2.5-acre property, this fully gated, 3 bedroom estate home offers privacy & sereni...

MLS#: W13682252
For Sale
Commercial for sale - 0 Bed, 0 Bath Home at 0 Airport Road Caledon ON listed at $9,999,000 (MLS# W13683328)
$9,999,000
0bd
0ba
Commercial

0 Airport Road, Caledon

Aug 17, 2026
DOM: 31

Prime 3.47-acre commercial development parcel strategically positioned on high-traffic Airport Road,...

MLS#: W13683328
For Sale
Residential Freehold for sale - 7 Bed, 8 Bath Home at 14374 Kennedy Road Caledon ON listed at $4,299,000 (MLS# W13681670)
$4,299,000
7bd
8ba
Residential Freehold

14374 Kennedy Road, Caledon

Aug 17, 2026
DOM: 31

**Welcome to an extraordinary custom-built luxury estate offering nearly 10,000 sq. ft. of refined l...

MLS#: W13681670
For Sale
Residential Freehold for sale - 4 Bed, 6 Bath Home at 23 Granite Stones Drive Caledon ON listed at $2,250,000 (MLS# W13670564)
$2,250,000
4bd
6ba
Residential Freehold

23 Granite Stones Drive, Caledon

Aug 13, 2026
DOM: 35

A rare offering on Granite Stones. Set on 2.5 acres, this updated log home is beautifully positioned...

MLS#: W13670564
For Sale
Residential Freehold for sale - 5 Bed, 5 Bath Home at 55 William Crisp Drive Caledon ON listed at $2,232,500 (MLS# W13668988)
$2,232,500
5bd
5ba
Residential Freehold

55 William Crisp Drive, Caledon

Aug 12, 2026
DOM: 36

Welcome to this Exceptional Custom-Built Estate Located in one of Caledon's Most Prestigious Luxury ...

MLS#: W13668988
For Sale
Residential Freehold for sale - 5 Bed, 3 Bath Home at 13186 Airport Road Caledon ON listed at $2,499,922 (MLS# W13668634)
$2,499,922
5bd
3ba
Residential Freehold

13186 Airport Road, Caledon

Aug 12, 2026
DOM: 36

fully upgraded (renovated), no one lived after Renovate, on Airport Rd on big lot, good size 4 bedro...

MLS#: W13668634
For Sale
Residential Freehold for sale - 5 Bed, 3 Bath Home at 6688 Mayfield Road Caledon ON listed at $8,500,000 (MLS# W13668606)
$8,500,000
5bd
3ba
Residential Freehold

6688 Mayfield Road, Caledon

Aug 11, 2026
DOM: 37

Investment opportunity on 4.65 acres in a prime Caledon location. Charming bungalow with open concep...

MLS#: W13668606
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 82 William Crisp Drive Caledon ON listed at $2,225,000 (MLS# W13659944)
Price Change
$2,225,000
4bd
4ba
Residential Freehold

82 William Crisp Drive, Caledon

Aug 10, 2026
DOM: 38

Featuring one of Osprey Mills' most desirable bungalow design, this exceptional ranch-style residenc...

MLS#: W13659944
For Sale
Commercial for sale - 0 Bed, 0 Bath Home at 29 Queen Street Caledon ON listed at $8,777,000 (MLS# W13669020)
$8,777,000
0bd
0ba
Commercial

29 Queen Street, Caledon

Aug 8, 2026
DOM: 40

RARE GEM ALERT! This exceptional property comprises three addresses 29, 31, and 33 Queen Street Nort...

MLS#: W13669020
For Sale
Residential Freehold for sale - 5 Bed, 3 Bath Home at 19246 Centreville Creek Road Caledon ON listed at $5,999,900 (MLS# W13653982)
$5,999,900
5bd
3ba
Residential Freehold

19246 Centreville Creek Road, Caledon

Aug 8, 2026
DOM: 40

//Spectacular **50 Acres** Country Estate Farmland Property With Stunning Views In Prestigious Rura...

MLS#: W13653982
For Sale
Commercial for sale - 0 Bed, 0 Bath Home at 19834 Airport Road Caledon ON listed at $2,625,000 (MLS# W13651074)
$2,625,000
0bd
0ba
Commercial

19834 Airport Road, Caledon

Aug 7, 2026
DOM: 41

Amazing Investment/End User opportunity in Caledon on Airport Rd South of Hwy 9. Rare Opportunity To...

MLS#: W13651074
For Sale
Residential Freehold for sale - 3 Bed, 3 Bath Home at 20 Buckstown Trail Caledon ON listed at $2,399,999 (MLS# W13650024)
Price Change
$2,399,999
3bd
3ba
Residential Freehold

20 Buckstown Trail, Caledon

Aug 7, 2026
DOM: 41

First time offered! Nestled in one of Palgrave's most sought-after enclaves, this exceptional 3-bedr...

MLS#: W13650024
For Sale
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