🏊 Inground & Heated Pools in Caledon

Homes with Pools for Sale in Caledon

Properties featuring inground, above-ground, or indoor swimming pools. 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, 3 Bath Home at 27 Cedar Drive Caledon ON listed at $2,225,000 (MLS# W13822806)
Added 1 day ago
$2,225,000
5bd
3ba
Residential Freehold

27 Cedar Drive, Caledon

Sep 24, 2026
DOM: 2

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

MLS#: W13822806
For Sale
Residential Freehold for sale - 3 Bed, 4 Bath Home at 9 Moraine Place Caledon ON listed at $1,999,000 (MLS# W13823288)
Added 1 day ago
$1,999,000
3bd
4ba
Residential Freehold

9 Moraine Place, Caledon

Sep 24, 2026
DOM: 2

Refined country living in one of Palgrave's most sought-after executive enclaves. Privately position...

MLS#: W13823288
For Sale
Residential Freehold for sale - 3 Bed, 3 Bath Home at 18 Alderbrook Place Caledon ON listed at $899,000 (MLS# W13818584)
Added 2 days ago
$899,000
3bd
3ba
Residential Freehold

18 Alderbrook Place, Caledon

Sep 23, 2026
DOM: 3

Fully renovated end-unit townhome offering the space, privacy and presence of a semi-detached, set o...

MLS#: W13818584
For Sale
Residential Freehold for sale - 7 Bed, 6 Bath Home at 7 Walton Drive Caledon ON listed at $2,999,995 (MLS# W13819302)
Added 2 days ago
$2,999,995
7bd
6ba
Residential Freehold

7 Walton Drive, Caledon

Sep 23, 2026
DOM: 3

Welcome to 7 Walton Drive in Palgrave Estates on Over 2 Acres, This House has 7 Bedrooms, 6 Bathroom...

MLS#: W13819302
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 2 days ago
$1,500,000
4bd
3ba
Residential Freehold

19 Mcconachie Crescent, Caledon

Sep 23, 2026
DOM: 3

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 - 6 Bed, 3 Bath Home at 32 Coolspring Crescent Caledon ON listed at $1,189,000 (MLS# W13812482)
Added 3 days ago
$1,189,000
6bd
3ba
Residential Freehold

32 Coolspring Crescent, Caledon

Sep 22, 2026
DOM: 4

Beautifully Updated South Hill Family Home Offering Over 3,800 sq. ft. of Living Space on a Spectacu...

MLS#: W13812482
For Sale
Residential Freehold for sale - 4 Bed, 2 Bath Home at 319 Dingle Court Caledon ON listed at $1,199,900 (MLS# W13813422)
Added 3 days ago
$1,199,900
4bd
2ba
Residential Freehold

319 Dingle Court, Caledon

Sep 22, 2026
DOM: 4

Rarely available and masterfully situated family residence resting on one of the most magnificent & ...

MLS#: W13813422
For Sale
Residential Condo & Other for sale - 2 Bed, 2 Bath Home at 60 Ann Street Caledon ON listed at $779,000 (MLS# W13814156)
Added 3 days ago
$779,000
2bd
2ba
Residential Condo & Other

60 Ann Street, Unit 313, Caledon

Sep 22, 2026
DOM: 4

Welcome to 313 at Boltons Coveted River's Edge, where privacy, space and a beautiful natural setting...

MLS#: W13814156
For Sale
Residential Freehold for sale - 5 Bed, 4 Bath Home at 34 Boyces Creek Court Caledon ON listed at $1,369,999 (MLS# W13814360)
Added 3 days ago
$1,369,999
5bd
4ba
Residential Freehold

34 Boyces Creek Court, Caledon

Sep 22, 2026
DOM: 4

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

MLS#: W13814360
For Sale
Residential Freehold for sale - 5 Bed, 3 Bath Home at 1666 Spruce Drive Caledon ON listed at $1,298,000 (MLS# W13817188)
Added 3 days ago
$1,298,000
5bd
3ba
Residential Freehold

1666 Spruce Drive, Caledon

Sep 22, 2026
DOM: 4

An entertainer's paradise in the Village of Caledon, this 5-bed, 2.5-bath offers a vast yard to play...

MLS#: W13817188
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 4 days ago
$1,089,000
4bd
3ba
Residential Freehold

5 Borland Crescent, Caledon

Sep 21, 2026
DOM: 5

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

MLS#: W13808498
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 7 days ago
$1,629,000
4bd
5ba
Residential Freehold

28 Billy Court, Caledon

Sep 18, 2026
DOM: 8

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

MLS#: W13802070
For Sale
Residential Freehold for sale - 5 Bed, 4 Bath Home at 44 George Crescent Caledon ON listed at $1,695,000 (MLS# W13802896)
Added 7 days ago
$1,695,000
5bd
4ba
Residential Freehold

44 George Crescent, Caledon

Sep 18, 2026
DOM: 8

Welcome to 44 George Crescent - an exceptional country estate in the prestigious executive community...

MLS#: W13802896
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 6 Mccandless Court Caledon ON listed at $1,500,000 (MLS# W13803644)
Added 7 days ago
$1,500,000
4bd
4ba
Residential Freehold

6 Mccandless Court, Caledon

Sep 18, 2026
DOM: 8

Welcome to one of Caledon East's most impressive family homes, offering nearly 4,000 sq. ft. of fini...

MLS#: W13803644
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 7 days ago
$1,479,000
5bd
5ba
Residential Freehold

51 Learmont Avenue, Caledon

Sep 18, 2026
DOM: 8

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

MLS#: W13803770
For Sale
Residential Freehold for sale - 3 Bed, 4 Bath Home at 50 North Riverdale Drive Caledon ON listed at $1,599,000 (MLS# W13805026)
Added 7 days ago
$1,599,000
3bd
4ba
Residential Freehold

50 North Riverdale Drive, Caledon

Sep 18, 2026
DOM: 8

Welcome to your private retreat in the charming and peaceful hamlet of Inglewood. Nestled on a spect...

MLS#: W13805026
For Sale
Residential Freehold for sale - 3 Bed, 3 Bath Home at 251 Bell Air Drive Caledon ON listed at $1,149,000 (MLS# W13785642)
Added 10 days ago
$1,149,000
3bd
3ba
Residential Freehold

251 Bell Air Drive, Caledon

Sep 15, 2026
DOM: 11

Highly sought after neighborhood in Bolton's south hill! Quiet mature area walking distance to all ...

MLS#: W13785642
For Sale
Residential Freehold for sale - 5 Bed, 4 Bath Home at 26 Shady Glen Crescent Caledon ON listed at $1,026,000 (MLS# W13782610)
$1,026,000
5bd
4ba
Residential Freehold

26 Shady Glen Crescent, Caledon

Sep 14, 2026
DOM: 12

Welcome to this meticulously maintained home nestled on a quiet, family-friendly cresent in Bolton's...

MLS#: W13782610
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 92 Headwater Road Caledon ON listed at $1,299,000 (MLS# W13782704)
Added 11 days ago
$1,299,000
4bd
4ba
Residential Freehold

92 Headwater Road, Caledon

Sep 14, 2026
DOM: 12

Welcome to this stunning, fully renovated two-storey family home in the heart of Bolton, where moder...

MLS#: W13782704
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 18 Filton Road Caledon ON listed at $1,799,900 (MLS# W13783274)
Added 11 days ago
$1,799,900
4bd
4ba
Residential Freehold

18 Filton Road, Caledon

Sep 14, 2026
DOM: 12

Welcome to 18 Filton Road, a custom-built executive home in the heart of Caledon East. This 4-bedroo...

MLS#: W13783274
For Sale
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 13 days ago
$2,468,000
5bd
6ba
Residential Freehold

2814 Forks Of The Credit Road, Caledon

Sep 12, 2026
DOM: 14

Welcome to a one-of-a-kind longevity estate where nature, privacy & wellness-focused design converge...

MLS#: W13776868
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)
$2,795,000
4bd
3ba
Residential Freehold

15 Caledon Mountain Drive, Caledon

Sep 10, 2026
DOM: 16

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 Condo & Other for sale - 2 Bed, 2 Bath Home at 60 Ann Street Caledon ON listed at $799,000 (MLS# W13769224)
$799,000
2bd
2ba
Residential Condo & Other

60 Ann Street, Unit 503, Caledon

Sep 10, 2026
DOM: 16

Luxury Condo in highly sought after "Rivers Edge" in downtown Bolton, walking distance to all amenit...

MLS#: W13769224
For Sale
Residential Freehold for sale - 4 Bed, 2 Bath Home at 25 Hilltop Drive Caledon ON listed at $1,179,000 (MLS# W13758914)
Price Change
$1,179,000
4bd
2ba
Residential Freehold

25 Hilltop Drive, Caledon

Sep 9, 2026
DOM: 17

***PUBLIC OPEN HOUSE - SATURDAY OCTOBER 3rd, 2:00-4:00pm*** Welcome to Hilltop Drive. One of Caledo...

MLS#: W13758914
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)
$2,299,999
4bd
5ba
Residential Freehold

13 Doctor Reynar Road, Caledon

Sep 9, 2026
DOM: 17

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

MLS#: W13762806
For Sale
Residential Freehold for sale - 4 Bed, 3 Bath Home at 19 Birch Avenue Caledon ON listed at $1,329,900 (MLS# W13763252)
$1,329,900
4bd
3ba
Residential Freehold

19 Birch Avenue, Caledon

Sep 9, 2026
DOM: 17

Welcome to this masterfully designed property in the heart of Palgrave, where timeless character mee...

MLS#: W13763252
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)
$2,498,000
5bd
3ba
Residential Freehold

4845 Escarpment Side Road, Caledon

Sep 9, 2026
DOM: 17

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, 4 Bath Home at 43 Strawberry Hill Court Caledon ON listed at $1,399,900 (MLS# W13755670)
$1,399,900
4bd
4ba
Residential Freehold

43 Strawberry Hill Court, Caledon

Sep 8, 2026
DOM: 18

Rarely does a property of this calibre become available, where traditional elegance and contemporary...

MLS#: W13755670
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: 22

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

MLS#: W13747140
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)
$5,250,000
5bd
7ba
Residential Freehold

7 Maple Meadow Court, Caledon

Sep 3, 2026
DOM: 23

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

MLS#: W13744042
For Sale
Residential Freehold for sale - 3 Bed, 5 Bath Home at 35 Brawton Drive Caledon ON listed at $1,999,000 (MLS# W13736076)
$1,999,000
3bd
5ba
Residential Freehold

35 Brawton Drive, Caledon

Sep 2, 2026
DOM: 24

Welcome to 35 Brawton Drive, an impressive family residence situated in the highly desirable communi...

MLS#: W13736076
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 23 Deer Valley Drive Caledon ON listed at $1,259,000 (MLS# W13732340)
$1,259,000
4bd
4ba
Residential Freehold

23 Deer Valley Drive, Caledon

Sep 1, 2026
DOM: 25

Welcome to 23 Deer Valley Drive, a beautifully maintained all brick family home set on a premium 142...

MLS#: W13732340
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: 29

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

MLS#: W13722256
For Sale
Residential Freehold for sale - 4 Bed, 3 Bath Home at 18 Mccabe Crescent Caledon ON listed at $1,399,000 (MLS# W13719478)
$1,399,000
4bd
3ba
Residential Freehold

18 Mccabe Crescent, Caledon

Aug 27, 2026
DOM: 30

Stunning Family Home in Desirable Bolton North - Welcome to this exceptional detached home in the hi...

MLS#: W13719478
For Sale
Residential Freehold for sale - 4 Bed, 3 Bath Home at 67 Sherin Court Caledon ON listed at $969,900 (MLS# W13713240)
$969,900
4bd
3ba
Residential Freehold

67 Sherin Court, Caledon

Aug 26, 2026
DOM: 31

Tucked away on a quiet court in Bolton's highly desirable North Hill community, this beautifully ren...

MLS#: W13713240
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: 31

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

MLS#: W13715192
For Sale
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