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Homes For Sale With Swimming Pool in Caledon, ON

Discover luxury homes and detached properties for sale featuring private in-ground or above-ground swimming pools.

Active MLS® Listings in Caledon

Browse the latest local MLS® property listings, updated real-time.

Residential Freehold for sale - 4 Bed, 5 Bath Home at 11 Summergate Court Caledon ON listed at $1,989,000 (MLS# W14180716)
Added 1 day ago
$1,989,000Est. $6,621/mo
3 + 1 = 4 bd
5ba
2kt
Residential Freehold

11 Summergate Court, Caledon

Nov 14, 2026
DOM: 2

4 bed, 5 bath Detached for sale in Caledon East. View photos, price history, school ratings & sold comps.

MLS#: W14180716
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 3 Bed, 2 Bath Home at 7803 Old Church Road Caledon ON listed at $1,049,000 (MLS# W14180010)
Added 1 day ago
$1,049,000Est. $3,492/mo
3 bd
2ba
1kt
Residential Freehold

7803 Old Church Road, Caledon

Nov 13, 2026
DOM: 3

3 bed, 2 bath Detached for sale in Rural Caledon. View photos, price history, school ratings & sold comps.

MLS#: W14180010
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 5 Bed, 5 Bath Home at 38 Gentle Fox Drive Caledon ON listed at $1,899,000 (MLS# W14163264)
Open House
$1,899,000Est. $6,321/mo
5 bd
5ba
2kt
Residential Freehold

38 Gentle Fox Drive, Caledon

đź“…Open House:Nov 15 1:00 PM
Nov 9, 2026
DOM: 7

5 bed, 5 bath Detached for sale in Rural Caledon. View photos, price history, school ratings & sold comps.

MLS#: W14163264
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 4 Bed, 4 Bath Home at 6 Mccandless Court Caledon ON listed at $1,399,000 (MLS# W14167976)
Added 4 days ago
$1,399,000Est. $4,657/mo
4 bd
4ba
1kt
Residential Freehold

6 Mccandless Court, Caledon

Nov 9, 2026
DOM: 7

4 bed, 4 bath Detached for sale in Caledon East. View photos, price history, school ratings & sold comps.

MLS#: W14167976
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 6 Bed, 5 Bath Home at 28 Walton Drive Caledon ON listed at $3,079,999 (MLS# W14160066)
Added 7 days ago
$3,079,999Est. $10,252/mo
4 + 2 = 6 bd
5ba
2kt
Residential Freehold

28 Walton Drive, Caledon

Nov 7, 2026
DOM: 9

6 bed, 5 bath Detached for sale in Palgrave. View photos, price history, school ratings & sold comps.

MLS#: W14160066
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 5 Bed, 4 Bath Home at 65 Paisley Green Avenue Caledon ON listed at $1,379,000 (MLS# W14156946)
Added 8 days ago
$1,379,000Est. $4,590/mo
4 + 1 = 5 bd
4ba
1kt
Residential Freehold

65 Paisley Green Avenue, Caledon

Nov 6, 2026
DOM: 10

5 bed, 4 bath Detached for sale in Caledon East. View photos, price history, school ratings & sold comps.

MLS#: W14156946
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 5 Bed, 10 Bath Home at 13214 Heritage Road Caledon ON listed at $1,499,000 (MLS# W14157570)
Added 8 days ago
$1,499,000Est. $4,990/mo
3 + 2 = 5 bd
10ba
1kt
Residential Freehold

13214 Heritage Road, Caledon

Nov 6, 2026
DOM: 10

5 bed, 10 bath Detached for sale in Rural Caledon. View photos, price history, school ratings & sold comps.

MLS#: W14157570
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 4 Bed, 5 Bath Home at 5 Coates Hill Court Caledon ON listed at $2,399,000 (MLS# W14159110)
Added 2 days ago
$2,399,000Est. $7,985/mo
4 bd
5ba
1kt
Residential Freehold

5 Coates Hill Court, Caledon

Nov 6, 2026
DOM: 10

4 bed, 5 bath Detached for sale in Palgrave. View photos, price history, school ratings & sold comps.

MLS#: W14159110
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 3 Bed, 2 Bath Home at 175 Allan Drive Caledon ON listed at $949,000 (MLS# W14153766)
Added 1 day ago
$949,000Est. $3,159/mo
3 bd
2ba
1kt
Residential Freehold

175 Allan Drive, Caledon

Nov 5, 2026
DOM: 11

3 bed, 2 bath Detached for sale in Bolton East. View photos, price history, school ratings & sold comps.

MLS#: W14153766
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 3 Bed, 2 Bath Home at 15 Emma Street Caledon ON listed at $819,000 (MLS# W14154610)
Added 9 days ago
$819,000Est. $2,726/mo
3 bd
2ba
1kt
Residential Freehold

15 Emma Street, Caledon

Nov 5, 2026
DOM: 11

3 bed, 2 bath Detached for sale in Caledon East. View photos, price history, school ratings & sold comps.

MLS#: W14154610
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 5 Bed, 3 Bath Home at 12792 Humber Station Road Caledon ON listed at $1,999,000 (MLS# W14155348)
Added 7 days ago
$1,999,000Est. $6,654/mo
3 + 2 = 5 bd
3ba
2kt
Residential Freehold

12792 Humber Station Road, Caledon

Nov 5, 2026
DOM: 11

5 bed, 3 bath Detached for sale in Rural Caledon. View photos, price history, school ratings & sold comps.

MLS#: W14155348
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 4 Bed, 3 Bath Home at 25 Field Crest Road Caledon ON listed at $1,299,000 (MLS# W14141014)
Added 12 days ago
$1,299,000Est. $4,324/mo
2 + 2 = 4 bd
3ba
1kt
Residential Freehold

25 Field Crest Road, Caledon

Nov 2, 2026
DOM: 14

4 bed, 3 bath Detached for sale in Inglewood. View photos, price history, school ratings & sold comps.

MLS#: W14141014
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 6 Bed, 10 Bath Home at 9 Flaherty Lane Caledon ON listed at $6,299,000 (MLS# W14134444)
$6,299,000Est. $20,967/mo
6 bd
10ba
2kt
Residential Freehold

9 Flaherty Lane, Caledon

Oct 30, 2026
DOM: 17

6 bed, 10 bath Detached for sale in Rural Caledon. View photos, price history, school ratings & sold comps.

MLS#: W14134444
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 3 Bed, 3 Bath Home at 18 Alderbrook Place Caledon ON listed at $849,000 (MLS# W14135666)
Added 11 days ago
$849,000Est. $2,826/mo
3 bd
3ba
1kt
Residential Freehold

18 Alderbrook Place, Caledon

Oct 30, 2026
DOM: 17

3 bed, 3 bath Att/Row/Townhouse for sale in Bolton North. View photos, price history, school ratings & sold comps.

MLS#: W14135666
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 4 Bed, 3 Bath Home at 53 Marilyn Street Caledon ON listed at $1,079,000 (MLS# W14119216)
Added 10 days ago
$1,079,000Est. $3,592/mo
3 + 1 = 4 bd
3ba
1kt
Residential Freehold

53 Marilyn Street, Caledon

Oct 27, 2026
DOM: 20

4 bed, 3 bath Detached for sale in Caledon East. View photos, price history, school ratings & sold comps.

MLS#: W14119216
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 4 Bed, 4 Bath Home at 23 Deer Valley Drive Caledon ON listed at $1,199,000 (MLS# W14121402)
$1,199,000Est. $3,991/mo
4 bd
4ba
1kt
Residential Freehold

23 Deer Valley Drive, Caledon

Oct 27, 2026
DOM: 20

4 bed, 4 bath Detached for sale in Bolton West. View photos, price history, school ratings & sold comps.

MLS#: W14121402
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 8 Bed, 7 Bath Home at 4 Woodlot Court Caledon ON listed at $2,729,000 (MLS# W14115532)
$2,729,000Est. $9,084/mo
8 bd
7ba
2kt
Residential Freehold

4 Woodlot Court, Caledon

Oct 25, 2026
DOM: 22

8 bed, 7 bath Detached for sale in Palgrave. View photos, price history, school ratings & sold comps.

MLS#: W14115532
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 4 Bed, 7 Bath Home at 40 Walton Drive Caledon ON listed at $2,899,900 (MLS# W14112872)
$2,899,900Est. $9,653/mo
4 bd
7ba
1kt
Residential Freehold

40 Walton Drive, Caledon

Oct 23, 2026
DOM: 24

4 bed, 7 bath Detached for sale in Palgrave. View photos, price history, school ratings & sold comps.

MLS#: W14112872
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 4 Bed, 4 Bath Home at 25 Mccandless Court Caledon ON listed at $1,299,999 (MLS# W14103128)
Price Change
$1,299,999Est. $4,327/mo
4 bd
4ba
1kt
Residential Freehold

25 Mccandless Court, Caledon

Oct 21, 2026
DOM: 26

4 bed, 4 bath Detached for sale in Caledon East. View photos, price history, school ratings & sold comps.

MLS#: W14103128
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 4 Bed, 4 Bath Home at 100 Walker Road Caledon ON listed at $1,034,000 (MLS# W14092190)
$1,034,000Est. $3,442/mo
3 + 1 = 4 bd
4ba
1kt
Residential Freehold

100 Walker Road, Caledon

Oct 19, 2026
DOM: 28

4 bed, 4 bath Semi-Detached for sale in Caledon East. View photos, price history, school ratings & sold comps.

MLS#: W14092190
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 4 Bed, 2 Bath Home at 20909 Shaws Creek Road Caledon ON listed at $1,069,000 (MLS# W14091658)
$1,069,000Est. $3,558/mo
4 bd
2ba
1kt
Residential Freehold

20909 Shaws Creek Road, Caledon

Oct 18, 2026
DOM: 29

4 bed, 2 bath Detached for sale in Alton. View photos, price history, school ratings & sold comps.

MLS#: W14091658
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 4 Bed, 3 Bath Home at 7 Compton Court Caledon ON listed at $1,199,000 (MLS# W14089740)
Price Change
$1,199,000Est. $3,991/mo
3 + 1 = 4 bd
3ba
1kt
Residential Freehold

7 Compton Court, Caledon

Oct 16, 2026
DOM: 31

4 bed, 3 bath Detached for sale in Bolton East. View photos, price history, school ratings & sold comps.

MLS#: W14089740
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Condo & Other for sale - 2 Bed, 2 Bath Home at 60 Ann Street Caledon ON listed at $799,000 (MLS# W14032996)
$799,000Est. $2,660/mo
2 bd
2ba
1kt
Residential Condo & Other

60 Ann Street, Unit 503, Caledon

Oct 14, 2026
DOM: 33

2 bed, 2 bath Condo Apartment for sale in Bolton West. View photos, price history, school ratings & sold comps.

MLS#: W14032996
For Sale
TRREB MLS® ActiveView Details & Comps →
Residential Freehold for sale - 4 Bed, 5 Bath Home at 7735 Old Church Road Caledon ON listed at $4,350,000 (MLS# W14011644)
$4,350,000Est. $14,480/mo
3 + 1 = 4 bd
5ba
1kt
Residential Freehold

7735 Old Church Road, Caledon

Oct 13, 2026
DOM: 34

4 bed, 5 bath Detached for sale in Rural Caledon. View photos, price history, school ratings & sold comps.

MLS#: W14011644
For Sale
TRREB MLS® ActiveView Details & Comps →
2026 Caledon Local Market Guide

Buying Homes For Sale With Swimming Pool in Caledon, ON (2026 Guide)

Caledon Avg List Price$2,364,544

There are currently 24 active homes for sale with swimming pool on the MLS® in Caledon, ON with a city average list price of $2,364,544. Comparing lot widths, GO Station commute times, and recent street-level sold prices helps you spot the best value before making an offer.

Commuter & GO Transit Access

Convenient access to major GTA highways (401, 407, 403, and QEW) and regional GO Transit stations connecting Caledon commuters to downtown Toronto.

Local Parks & School Catchments

Close to local conservation areas, community recreation centres, trails, and well-rated elementary and secondary school catchments in Caledon.

Lot Widths & Housing Mix

Older established streets in Caledon offer wider 50 to 60+ ft mature lots, while newer master-planned subdivisions feature modern 30 to 36 ft energy-efficient layouts.

Common Questions About Homes For Sale With Swimming Pool in Caledon

How many homes for sale with swimming pool are available in Caledon in 2026?

There are currently 24 active MLS® listings matching homes for sale with swimming pool in Caledon, ON. Inventory updates every 15 minutes directly from TRREB.

What is the average home price in Caledon right now?

The current benchmark list price across Caledon is $2,364,544. Prices for homes for sale with swimming pool vary depending on lot width, school catchment, and recent renovations.

Which neighborhoods in Caledon are best for homes for sale with swimming pool?

Older established streets in Caledon offer wider 50 to 60+ ft mature lots, while newer master-planned subdivisions feature modern 30 to 36 ft energy-efficient layouts. Before submitting an offer, compare recent 30-day TRREB sold prices on the same street to make sure you don't overpay.

Verified with real-time Toronto Regional Real Estate Board (TRREB) MLS® data.
View All CaledonHomes For Sale & Community Report →