🏊 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 - 4 Bed, 4 Bath Home at 6 Mccandless Court Caledon ON listed at $1,425,000 (MLS# W14101702)
Added 2 days ago
$1,425,000Est. $4,743/mo
4bd
4ba
Residential Freehold

6 Mccandless Court, Caledon

Oct 21, 2026
DOM: 3

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

MLS#: W14101702
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 25 Mccandless Court Caledon ON listed at $1,319,999 (MLS# W14103128)
Added 2 days ago
$1,319,999Est. $4,394/mo
4bd
4ba
Residential Freehold

25 Mccandless Court, Caledon

Oct 21, 2026
DOM: 3

Welcome To 25 McCandless Court, A Stunning 3000+ sq ft plus finished basement 4-Bedroom, 4-Bathroom ...

MLS#: W14103128
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 100 Walker Road Caledon ON listed at $1,034,000 (MLS# W14092190)
Added 4 days ago
$1,034,000Est. $3,442/mo
4bd
4ba
Residential Freehold

100 Walker Road, Caledon

Oct 19, 2026
DOM: 5

Welcome to this stunning semi-detached home in the highly desirable community of West Caledon, set o...

MLS#: W14092190
For Sale
Residential Freehold for sale - 4 Bed, 2 Bath Home at 20909 Shaws Creek Road Caledon ON listed at $1,069,000 (MLS# W14091658)
Added 5 days ago
$1,069,000Est. $3,558/mo
4bd
2ba
Residential Freehold

20909 Shaws Creek Road, Caledon

Oct 18, 2026
DOM: 6

A Storybook Country Escape in the Heart of Caledon! Tucked among mature trees and rolling hills, thi...

MLS#: W14091658
For Sale
Residential Freehold for sale - 3 Bed, 3 Bath Home at 19617 Mountainview Road Caledon ON listed at $2,800,000 (MLS# W14094660)
Added 5 days ago
$2,800,000Est. $9,320/mo
3bd
3ba
Residential Freehold

19617 Mountainview Road, Caledon

Oct 18, 2026
DOM: 6

50 Acres of Caledon Countryside Paradise! Rare opportunity to own approximately 50 acres of beautifu...

MLS#: W14094660
For Sale
Residential Freehold for sale - 4 Bed, 3 Bath Home at 7 Compton Court Caledon ON listed at $1,268,000 (MLS# W14089740)
Added 7 days ago
$1,268,000Est. $4,221/mo
4bd
3ba
Residential Freehold

7 Compton Court, Caledon

Oct 16, 2026
DOM: 8

Welcome to 7 Compton Court, a beautifully renovated home situated on a quiet, family-friendly court ...

MLS#: W14089740
For Sale
Residential Condo & Other for sale - 2 Bed, 2 Bath Home at 60 Ann Street Caledon ON listed at $799,000 (MLS# W14032996)
Added 9 days ago
$799,000Est. $2,660/mo
2bd
2ba
Residential Condo & Other

60 Ann Street, Unit 503, Caledon

Oct 14, 2026
DOM: 10

Enjoy an exceptional lifestyle at Rivers Edge, a highly sought-after Luxury Condos in downtown Bolto...

MLS#: W14032996
For Sale
Residential Freehold for sale - 4 Bed, 5 Bath Home at 7735 Old Church Road Caledon ON listed at $4,350,000 (MLS# W14011644)
Added 10 days ago
$4,350,000Est. $14,480/mo
4bd
5ba
Residential Freehold

7735 Old Church Road, Caledon

Oct 13, 2026
DOM: 11

Exceptional distinguished Caledon estate, custom-built luxury bungalow over 7700+ sq.ft. of living s...

MLS#: W14011644
For Sale
Residential Freehold for sale - 5 Bed, 4 Bath Home at 3 Natureview Court Caledon ON listed at $1,649,000 (MLS# W14029196)
Added 10 days ago
$1,649,000Est. $5,489/mo
5bd
4ba
Residential Freehold

3 Natureview Court, Caledon

Oct 13, 2026
DOM: 11

Situated In Boltons Most Sought After North Hill. Gorgeous 4+1 Bedroom, 4 Bathroom Home Nestled on a...

MLS#: W14029196
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 15252 Chinguacousy Road Caledon ON listed at $1,599,900 (MLS# W14031462)
Added 10 days ago
$1,599,900Est. $5,325/mo
4bd
4ba
Residential Freehold

15252 Chinguacousy Road, Caledon

Oct 13, 2026
DOM: 11

Wow! Resort-Style Living On 1 Acre Treed Lot, Unbelievably Close To The City. Heated Saltwater Pool,...

MLS#: W14031462
For Sale
Residential Freehold for sale - 4 Bed, 2 Bath Home at 8 Waterbury Street Caledon ON listed at $979,000 (MLS# W13874914)
$979,000Est. $3,259/mo
4bd
2ba
Residential Freehold

8 Waterbury Street, Caledon

Oct 8, 2026
DOM: 16

5 Reasons Why You Will Love This Detached 2-Storey Home: 1) The upper floor features a 4-piece bathr...

MLS#: W13874914
For Sale
Residential Freehold for sale - 3 Bed, 4 Bath Home at 81 Matson Drive Caledon ON listed at $2,299,000 (MLS# W13875376)
$2,299,000Est. $7,653/mo
3bd
4ba
Residential Freehold

81 Matson Drive, Caledon

Oct 8, 2026
DOM: 16

Tucked away in the prestigious Palgrave community of Caledon, this exceptional private residence off...

MLS#: W13875376
For Sale
Residential Freehold for sale - 5 Bed, 2 Bath Home at 16718 Caledon King Townline Caledon ON listed at $2,999,995 (MLS# W13861262)
$2,999,995Est. $9,986/mo
5bd
2ba
Residential Freehold

16718 Caledon King Townline, Caledon

Oct 5, 2026
DOM: 19

A Rare Gated Country Estate Set On Just Under 25 Acres, Where Privacy, Natural Beauty And Exceptiona...

MLS#: W13861262
For Sale
Residential Freehold for sale - 5 Bed, 3 Bath Home at 32 Caledon Street Caledon ON listed at $929,999 (MLS# W13862038)
$929,999Est. $3,096/mo
5bd
3ba
Residential Freehold

32 Caledon Street, Caledon

Oct 5, 2026
DOM: 19

Beautiful 3+2 Bedroom Bungalow with a WALKOUT BASEMENT!! Welcome to this stunning fully renovated bu...

MLS#: W13862038
For Sale
Residential Freehold for sale - 5 Bed, 4 Bath Home at 172 Bell Air Drive Caledon ON listed at $1,899,000 (MLS# W13864098)
$1,899,000Est. $6,321/mo
5bd
4ba
Residential Freehold

172 Bell Air Drive, Caledon

Oct 5, 2026
DOM: 19

Welcome to 172 Bell Air Drive, a one of a kind fully renovated, turnkey home offering resort-style l...

MLS#: W13864098
For Sale
Residential Freehold for sale - 5 Bed, 4 Bath Home at 34 Boyces Creek Court Caledon ON listed at $1,379,999 (MLS# W13864934)
$1,379,999Est. $4,594/mo
5bd
4ba
Residential Freehold

34 Boyces Creek Court, Caledon

Oct 5, 2026
DOM: 19

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

MLS#: W13864934
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 38 Marilyn Street Caledon ON listed at $1,569,900 (MLS# W13856054)
$1,569,900Est. $5,226/mo
4bd
4ba
Residential Freehold

38 Marilyn Street, Caledon

Oct 2, 2026
DOM: 22

Over an acre in the village of Caledon East. Set on a 100 x 495 ft lot (1.14 acres) with mature tree...

MLS#: W13856054
For Sale
Residential Freehold for sale - 5 Bed, 5 Bath Home at 38 Gentle Fox Drive Caledon ON listed at $2,188,000 (MLS# W13841560)
$2,188,000Est. $7,283/mo
5bd
5ba
Residential Freehold

38 Gentle Fox Drive, Caledon

Sep 29, 2026
DOM: 25

Welcome to 38 Gentle Fox Drive, a luxurious Caledon residence offering over 4,000 sq. ft. of beautif...

MLS#: W13841560
For Sale
Residential Freehold for sale - 3 Bed, 3 Bath Home at 16112 The Gore Road Caledon ON listed at $1,788,000 (MLS# W13835832)
$1,788,000Est. $5,952/mo
3bd
3ba
Residential Freehold

16112 The Gore Road, Caledon

Sep 28, 2026
DOM: 26

Welcome to this exquisite custom-built Raised Bungalow offering approximately 2,545 sq. ft. on the m...

MLS#: W13835832
For Sale
Residential Freehold for sale - 5 Bed, 4 Bath Home at 18584 The Gore Road Caledon ON listed at $2,400,000 (MLS# W13827282)
$2,400,000Est. $7,989/mo
5bd
4ba
Residential Freehold

18584 The Gore Road, Caledon

Sep 25, 2026
DOM: 29

One Of Caledon's Most Scenic, Stunning Properties. Set Privately, Bordered By Mature Trees & Forest ...

MLS#: W13827282
For Sale
Residential Freehold for sale - 5 Bed, 5 Bath Home at 95 Pembrook Street Caledon ON listed at $1,649,999 (MLS# W13830262)
$1,649,999Est. $5,492/mo
5bd
5ba
Residential Freehold

95 Pembrook Street, Caledon

Sep 25, 2026
DOM: 29

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 - 5 Bed, 3 Bath Home at 27 Cedar Drive Caledon ON listed at $2,225,000 (MLS# W13822806)
$2,225,000Est. $7,406/mo
5bd
3ba
Residential Freehold

27 Cedar Drive, Caledon

Sep 24, 2026
DOM: 30

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)
$1,999,000Est. $6,654/mo
3bd
4ba
Residential Freehold

9 Moraine Place, Caledon

Sep 24, 2026
DOM: 30

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)
$899,000Est. $2,992/mo
3bd
3ba
Residential Freehold

18 Alderbrook Place, Caledon

Sep 23, 2026
DOM: 31

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 - 8 Bed, 6 Bath Home at 7 Walton Drive Caledon ON listed at $2,999,995 (MLS# W13819302)
$2,999,995Est. $9,986/mo
8bd
6ba
Residential Freehold

7 Walton Drive, Caledon

Sep 23, 2026
DOM: 31

Welcome to 7 Walton Drive in Palgrave Estates on Over 2 Acres, This House has 8 Bedrooms, 6 Bathroom...

MLS#: W13819302
For Sale
Residential Freehold for sale - 4 Bed, 3 Bath Home at 19 Mcconachie Crescent Caledon ON listed at $1,450,000 (MLS# W13821904)
Price Change
$1,450,000Est. $4,827/mo
4bd
3ba
Residential Freehold

19 Mcconachie Crescent, Caledon

Sep 23, 2026
DOM: 31

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)
$1,189,000Est. $3,958/mo
6bd
3ba
Residential Freehold

32 Coolspring Crescent, Caledon

Sep 22, 2026
DOM: 32

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 - 5 Bed, 3 Bath Home at 1666 Spruce Drive Caledon ON listed at $1,298,000 (MLS# W13817188)
$1,298,000Est. $4,321/mo
5bd
3ba
Residential Freehold

1666 Spruce Drive, Caledon

Sep 22, 2026
DOM: 32

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)
$1,089,000Est. $3,625/mo
4bd
3ba
Residential Freehold

5 Borland Crescent, Caledon

Sep 21, 2026
DOM: 33

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 44 George Crescent Caledon ON listed at $1,695,000 (MLS# W13802896)
$1,695,000Est. $5,642/mo
5bd
4ba
Residential Freehold

44 George Crescent, Caledon

Sep 18, 2026
DOM: 36

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

MLS#: W13802896
For Sale
Residential Freehold for sale - 5 Bed, 5 Bath Home at 51 Learmont Avenue Caledon ON listed at $1,479,000 (MLS# W13803770)
$1,479,000Est. $4,923/mo
5bd
5ba
Residential Freehold

51 Learmont Avenue, Caledon

Sep 18, 2026
DOM: 36

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 $1,539,000 (MLS# W13805026)
Price Change
$1,539,000Est. $5,123/mo
3bd
4ba
Residential Freehold

50 North Riverdale Drive, Caledon

Sep 18, 2026
DOM: 36

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 - 4 Bed, 4 Bath Home at 18 Filton Road Caledon ON listed at $1,799,900 (MLS# W13783274)
$1,799,900Est. $5,991/mo
4bd
4ba
Residential Freehold

18 Filton Road, Caledon

Sep 14, 2026
DOM: 40

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)
$2,468,000Est. $8,215/mo
5bd
6ba
Residential Freehold

2814 Forks Of The Credit Road, Caledon

Sep 12, 2026
DOM: 42

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)
$2,795,000Est. $9,304/mo
4bd
3ba
Residential Freehold

15 Caledon Mountain Drive, Caledon

Sep 10, 2026
DOM: 44

No need for AI embellishment here! This one-of-a-kind, 3.3 acre country retreat located just outside...

MLS#: W13768664
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
$1,179,000Est. $3,924/mo
4bd
2ba
Residential Freehold

25 Hilltop Drive, Caledon

Sep 9, 2026
DOM: 45

Welcome to Hilltop Drive. One of Caledon East's most desirable communities. This beautifully updated...

MLS#: W13758914
For Sale
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