🔑 In-Law Suites in Caledon

Homes with Separate Entrance in Caledon

Multi-generational living and potential rental income basements. 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, 5 Bath Home at 95 Pembrook Street Caledon ON listed at $1,649,999 (MLS# W13830262)
Added 1 day ago
$1,649,999
5bd
5ba
Residential Freehold

95 Pembrook Street, Caledon

Sep 25, 2026
DOM: 2

Welcome to this brand new 3581 sqft, luxury home located in one of Bolton's most desirable, family-f...

MLS#: W13830262
For Sale
Residential Freehold for sale - 3 Bed, 2 Bath Home at 17 Heather Street Caledon ON listed at $599,999 (MLS# W13830506)
Added 1 day ago
$599,999
3bd
2ba
Residential Freehold

17 Heather Street, Caledon

Sep 25, 2026
DOM: 2

Here's Your opportunity to own a 3-bedroom bungalow on an impressive 100' x 150' corner lot in a qui...

MLS#: W13830506
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 9 Sheardown Trail Caledon ON listed at $1,080,000 (MLS# W13832130)
Added 1 day ago
$1,080,000
4bd
4ba
Residential Freehold

9 Sheardown Trail, Caledon

Sep 25, 2026
DOM: 2

Welcome to 9 Sheardown Trail, an elegant and beautifully updated detached residence nestled in one o...

MLS#: W13832130
For Sale
Residential Freehold for sale - 5 Bed, 3 Bath Home at 27 Cedar Drive Caledon ON listed at $2,225,000 (MLS# W13822806)
Added 2 days ago
$2,225,000
5bd
3ba
Residential Freehold

27 Cedar Drive, Caledon

Sep 24, 2026
DOM: 3

Magnificent Georgian Estate in Prestigious Caledon! Welcome to an extraordinary 5-bedroom, 3-bathroo...

MLS#: W13822806
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 64 Mcpherson Road Caledon ON listed at $969,000 (MLS# W13824276)
Added 2 days ago
$969,000
4bd
4ba
Residential Freehold

64 Mcpherson Road, Caledon

Sep 24, 2026
DOM: 3

FIRST TIME HOME BUYER DREAM!!! Ready to Move-In!! Located in Heart of Caledon surrounded with Shoppi...

MLS#: W13824276
For Sale
Residential Freehold for sale - 5 Bed, 4 Bath Home at 15191 Airport Road Caledon ON listed at $2,599,000 (MLS# W13827252)
Added 2 days ago
$2,599,000
5bd
4ba
Residential Freehold

15191 Airport Road, Caledon

Sep 24, 2026
DOM: 3

Welcome to this incredible meticulously kept and built residence (2005) situated on a sprawling, pri...

MLS#: W13827252
For Sale
Residential Freehold for sale - 4 Bed, 3 Bath Home at 19 Mcconachie Crescent Caledon ON listed at $1,500,000 (MLS# W13821904)
Added 3 days ago
$1,500,000
4bd
3ba
Residential Freehold

19 Mcconachie Crescent, Caledon

Sep 23, 2026
DOM: 4

Beautifully maintained raised bungalow set on a private 1.5-acre country lot, offering the perfect b...

MLS#: W13821904
For Sale
Residential Freehold for sale - 4 Bed, 3 Bath Home at 102 Grapevine Road Caledon ON listed at $839,990 (MLS# W13813420)
Added 4 days ago
$839,990
4bd
3ba
Residential Freehold

102 Grapevine Road, Caledon

Sep 22, 2026
DOM: 5

This Well Maintained Home Is Located near a Quiet Cul De Sac In A Desirable Neighbourhood. Its exten...

MLS#: W13813420
For Sale
Residential Freehold for sale - 5 Bed, 2 Bath Home at 55 John Street Caledon ON listed at $959,000 (MLS# W13813714)
Added 4 days ago
$959,000
5bd
2ba
Residential Freehold

55 John Street, Caledon

Sep 22, 2026
DOM: 5

Welcome to 55 John St! Totally renovated bungalow finished from top to bottom on a 66x160 ft mature...

MLS#: W13813714
For Sale
Residential Freehold for sale - 5 Bed, 5 Bath Home at 7 Proctor Avenue Caledon ON listed at $2,595,000 (MLS# W13814062)
Added 4 days ago
$2,595,000
5bd
5ba
Residential Freehold

7 Proctor Avenue, Caledon

Sep 22, 2026
DOM: 5

Set amidst the natural beauty & privacy of prestigious Millcreek Estates, this exceptional 2-storey ...

MLS#: W13814062
For Sale
Residential Freehold for sale - 5 Bed, 4 Bath Home at 34 Boyces Creek Court Caledon ON listed at $1,449,999 (MLS# W13814360)
Price Change
$1,449,999
5bd
4ba
Residential Freehold

34 Boyces Creek Court, Caledon

Sep 22, 2026
DOM: 5

Welcome home to this beautifully designed 2-storey residence, offering the perfect blend of comforta...

MLS#: W13814360
For Sale
Residential Freehold for sale - 4 Bed, 3 Bath Home at 48 De Rose Avenue Caledon ON listed at $1,199,000 (MLS# W13814756)
Added 4 days ago
$1,199,000
4bd
3ba
Residential Freehold

48 De Rose Avenue, Caledon

Sep 22, 2026
DOM: 5

Welcome To 48 De Rose Ave, Ideally Situated In The Heart Of Bolton And Backing Onto A Premium Ravine...

MLS#: W13814756
For Sale
Residential Freehold for sale - 4 Bed, 3 Bath Home at 5 Borland Crescent Caledon ON listed at $1,089,000 (MLS# W13808498)
Added 5 days ago
$1,089,000
4bd
3ba
Residential Freehold

5 Borland Crescent, Caledon

Sep 21, 2026
DOM: 6

Welcome to 5 Borland Crescent, where thoughtful updates, modern finishes, & comfortable living come ...

MLS#: W13808498
For Sale
Residential Freehold for sale - 5 Bed, 4 Bath Home at 10 RIVERWOOD Terrace Caledon ON listed at $1,699,998 (MLS# W13814672)
Added 5 days ago
$1,699,998
5bd
4ba
Residential Freehold

10 RIVERWOOD Terrace, Caledon

Sep 21, 2026
DOM: 6

PLEASE TAKE NOTE!!! ONE OF A KIND CUSTOM INTERIOR BUNGALOW LOFT!!! THIS IS NOT A SUBDIVISION BASIC G...

MLS#: W13814672
For Sale
Residential Freehold for sale - 4 Bed, 5 Bath Home at 28 Billy Court Caledon ON listed at $1,629,000 (MLS# W13802070)
Added 8 days ago
$1,629,000
4bd
5ba
Residential Freehold

28 Billy Court, Caledon

Sep 18, 2026
DOM: 9

Welcome to 28 Billy Court, an exceptional luxury residence in Caledon East, where refined elegance m...

MLS#: W13802070
For Sale
Residential Freehold for sale - 7 Bed, 7 Bath Home at 54 Ash Hill Avenue Caledon ON listed at $1,299,800 (MLS# W13802332)
Added 8 days ago
$1,299,800
7bd
7ba
Residential Freehold

54 Ash Hill Avenue, Caledon

Sep 18, 2026
DOM: 9

ON 5OFT LOT " Gorgeous Home In The Pathways Community Of Caledon East!This Upgraded Home Features A ...

MLS#: W13802332
For Sale
Residential Freehold for sale - 5 Bed, 5 Bath Home at 51 Learmont Avenue Caledon ON listed at $1,479,000 (MLS# W13803770)
Added 8 days ago
$1,479,000
5bd
5ba
Residential Freehold

51 Learmont Avenue, Caledon

Sep 18, 2026
DOM: 9

Location! Location! Location! Welcome to this stunning, fully upgraded 4-bedroom detached home in th...

MLS#: W13803770
For Sale
Residential Freehold for sale - 5 Bed, 8 Bath Home at 16735 Shaws Creek Road Caledon ON listed at $4,699,000 (MLS# W13804054)
Added 8 days ago
$4,699,000
5bd
8ba
Residential Freehold

16735 Shaws Creek Road, Caledon

Sep 18, 2026
DOM: 9

This executive-quality estate offers five-star quality and a year-round Muskoka environment without ...

MLS#: W13804054
For Sale
Residential Freehold for sale - 8 Bed, 9 Bath Home at 91 Troiless Street Caledon ON listed at $6,200,000 (MLS# W13790244)
Added 10 days ago
$6,200,000
8bd
9ba
Residential Freehold

91 Troiless Street, Caledon

Sep 16, 2026
DOM: 11

Welcome To This Gorgeous One-Of-A-Kind Luxury Custom Built Detached Estate Home Situated On 1 Privat...

MLS#: W13790244
For Sale
Residential Freehold for sale - 6 Bed, 5 Bath Home at 43 Valleyscape Trail Caledon ON listed at $1,495,000 (MLS# W13790540)
$1,495,000
6bd
5ba
Residential Freehold

43 Valleyscape Trail, Caledon

Sep 16, 2026
DOM: 11

Immaculate Home 4+2 Bed, 5 Bath, Spotless Beautiful Home in Prestigious Southfields in Caledon, Brig...

MLS#: W13790540
For Sale
Residential Freehold for sale - 5 Bed, 5 Bath Home at 52 Westchester Boulevard Caledon ON listed at $1,299,000 (MLS# W13790790)
Added 10 days ago
$1,299,000
5bd
5ba
Residential Freehold

52 Westchester Boulevard, Caledon

Sep 16, 2026
DOM: 11

Welcome to 52 Westchester Blvd. A spacious and well-maintained home located in Bolton's desirable No...

MLS#: W13790790
For Sale
Residential Freehold for sale - 8 Bed, 9 Bath Home at 35 Arthur Griffin Crescent Caledon ON listed at $1,999,999 (MLS# W13794746)
Added 10 days ago
$1,999,999
8bd
9ba
Residential Freehold

35 Arthur Griffin Crescent, Caledon

Sep 16, 2026
DOM: 11

Show Stopper !! Perfect Multi-Generational Home P.L.U.S. Income Property $2,500 / month. P.L.U.S. In...

MLS#: W13794746
For Sale
Residential Freehold for sale - 5 Bed, 3 Bath Home at 18599 Horseshoe Hill Road Caledon ON listed at $1,298,000 (MLS# W13794850)
Added 10 days ago
$1,298,000
5bd
3ba
Residential Freehold

18599 Horseshoe Hill Road, Caledon

Sep 16, 2026
DOM: 11

Located on a paved country road, this 3+2 bedroom, 3-bathroom raised bungalow set on a private, tree...

MLS#: W13794850
For Sale
Residential Freehold for sale - 7 Bed, 7 Bath Home at 30 Albert Spencer Avenue Caledon ON listed at $1,379,000 (MLS# W13785848)
Added 11 days ago
$1,379,000
7bd
7ba
Residential Freehold

30 Albert Spencer Avenue, Caledon

Sep 15, 2026
DOM: 12

Welcome to this spacious and beautifully designed home offering over 3,500 sq. ft. of above-grade li...

MLS#: W13785848
For Sale
Residential Freehold for sale - 5 Bed, 3 Bath Home at 12821 Heritage Road Caledon ON listed at $1,295,000 (MLS# W13786244)
Added 11 days ago
$1,295,000
5bd
3ba
Residential Freehold

12821 Heritage Road, Caledon

Sep 15, 2026
DOM: 12

Great Country Living only Minutes F/ Brampton, Georgetown & Glen Williams. Newly Renovated Detached ...

MLS#: W13786244
For Sale
Residential Freehold for sale - 6 Bed, 5 Bath Home at 6425 Old Church Road Caledon ON listed at $1,999,900 (MLS# W13780834)
Added 12 days ago
$1,999,900
6bd
5ba
Residential Freehold

6425 Old Church Road, Caledon

Sep 14, 2026
DOM: 13

Exceptional newer custom-built residence offering 4,088 sq. ft. above grade, thoughtfully designed w...

MLS#: W13780834
For Sale
Residential Freehold for sale - 5 Bed, 3 Bath Home at 17 Autumn Drive Caledon ON listed at $1,959,000 (MLS# W13781438)
Added 12 days ago
$1,959,000
5bd
3ba
Residential Freehold

17 Autumn Drive, Caledon

Sep 14, 2026
DOM: 13

Stripped back, rebuilt & completely transformed into a custom modern farmhouse bungalow on approx 1 ...

MLS#: W13781438
For Sale
Residential Freehold for sale - 6 Bed, 6 Bath Home at 84 Kennedy Road Caledon ON listed at $2,899,000 (MLS# W13771530)
$2,899,000
6bd
6ba
Residential Freehold

84 Kennedy Road, Caledon

Sep 11, 2026
DOM: 16

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

MLS#: W13771530
For Sale
Residential Freehold for sale - 7 Bed, 6 Bath Home at 1 Breckonwood Street Caledon ON listed at $1,599,000 (MLS# W13768250)
$1,599,000
7bd
6ba
Residential Freehold

1 Breckonwood Street, Caledon

Sep 10, 2026
DOM: 17

Showstopper! Welcome To This Fully Upgraded Corner Home In A Prime Caledon Location, Offering3,224 S...

MLS#: W13768250
For Sale
Residential Freehold for sale - 4 Bed, 3 Bath Home at 34 Kirkwood Crescent Caledon ON listed at $954,000 (MLS# W13768978)
$954,000
4bd
3ba
Residential Freehold

34 Kirkwood Crescent, Caledon

Sep 10, 2026
DOM: 17

Welcome to this bright, spacious, and exceptionally functional 3-bedroom bungalow inthe highly sough...

MLS#: W13768978
For Sale
Residential Freehold for sale - 6 Bed, 4 Bath Home at 15 Speckled Alder Street Caledon ON listed at $1,299,900 (MLS# W13759952)
$1,299,900
6bd
4ba
Residential Freehold

15 Speckled Alder Street, Caledon

Sep 9, 2026
DOM: 18

2697 Sq Ft As Per Mpac!! Come & Check Out This Fully Detached Luxurious Home Built On 36 Ft Wide Lot...

MLS#: W13759952
For Sale
Residential Freehold for sale - 7 Bed, 6 Bath Home at 58 Petch Avenue Caledon ON listed at $1,479,000 (MLS# W13752624)
$1,479,000
7bd
6ba
Residential Freehold

58 Petch Avenue, Caledon

Sep 8, 2026
DOM: 19

Absolute gorgeous 5 Bedroom with finished legal basement with separate entrance .Near Mayfield/McLau...

MLS#: W13752624
For Sale
Residential Freehold for sale - 6 Bed, 5 Bath Home at 4 Tranquility Court Caledon ON listed at $2,049,000 (MLS# W13753596)
$2,049,000
6bd
5ba
Residential Freehold

4 Tranquility Court, Caledon

Sep 8, 2026
DOM: 19

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, 4 Bath Home at 1 Cedar Drive Caledon ON listed at $1,899,999 (MLS# W13757944)
$1,899,999
4bd
4ba
Residential Freehold

1 Cedar Drive, Caledon

Sep 8, 2026
DOM: 19

Welcome to 1 Cedar Drive, an exceptional estate set on nearly 3 acres of mature forest with a pictur...

MLS#: W13757944
For Sale
Residential Freehold for sale - 6 Bed, 4 Bath Home at 7 Salt Creek Terrace Caledon ON listed at $1,050,000 (MLS# W13744300)
$1,050,000
6bd
4ba
Residential Freehold

7 Salt Creek Terrace, Caledon

Sep 4, 2026
DOM: 23

Welcome to 7 Salt Creek Terrace-an exceptional East-facing detached home that perfectly blends sophi...

MLS#: W13744300
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)
$2,144,000
5bd
4ba
Residential Freehold

11 Prince Andrew Drive, Caledon

Sep 4, 2026
DOM: 23

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

MLS#: W13747140
For Sale
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