Collections · Caledon

Homes with a pool in Caledon

64 for sale in Caledon right now, updated from the TRREB feed through the day. In-ground and above-ground pools, across the GTA and Durham.

64For sale now

$950,000Median sold · Sep 2026

65Homes sold · Sep 2026

27Days on market · Sep 2026

96.5%Sold vs asking · Sep 2026

Caledon market reportTrends & data →

A pool is the clearest example of a feature that is worth a great deal to the buyer who wants one and slightly negative to the buyer who does not. That split is why pool homes sit differently in the market than their comparables suggest, and why they are worth searching for directly.

See every one across the GTA → · All homes for sale in Caledon →

Popular neighbourhoods:Rural Caledon Palgrave Caledon East Bolton East Caledon Village Bolton West Alton Inglewood Bolton North Cheltenham All Caledon neighbourhoods ↓

Ways to browse:Walk-out basements 95 Bungalows 93 Homes with an in-law suite 84 Luxury homes ($2M+) 75 Just reduced 72 Homes with a pool 64 Detached under $1M 54 New this week 39

Homes with a pool for sale

64 in Caledon · newest 24 shown

81 Matson Drive, Caledon, ON L7E 0A3

81 Matson DriveCaledon, ON L7E 0A3

Caledon · Palgrave

3 bed4 bath23 parking

MLS® W13875376RE/MAX EXPERTS

1666 Spruce Drive, Caledon, ON L7K 1B2

1666 Spruce DriveCaledon, ON L7K 1B2

Caledon · Caledon Village

5 bed3 bath8 parking

MLS® W13817188CENTURY 21 MILLENNIUM INC.

2097 Grange Side Road, Caledon, ON L7C 0E7

2097 Grange Side RoadCaledon, ON L7C 0E7

Caledon · Rural Caledon

8 + 1 bed9 bath54 parking

MLS® W13573998ROYAL LEPAGE MEADOWTOWNE REALTY

14812 Centreville Creek Road, Caledon, ON L7C 3B1

14812 Centreville Creek RoadCaledon, ON L7C 3B1

Caledon · Rural Caledon

3 + 2 bed4 bath12 parking

MLS® W13726484RE/MAX EXCELLENCE REAL ESTATE

16735 Mississauga Road, Caledon, ON L7K 1M8

16735 Mississauga RoadCaledon, ON L7K 1M8

Caledon · Rural Caledon

3 bed2 bath8 parking

MLS® W12945004SUTTON-HEADWATERS REALTY INC.

14294 Winston Churchill Boulevard, Caledon, ON L7C 3E8

14294 Winston Churchill BoulevardCaledon, ON L7C 3E8

Caledon · Rural Caledon

4 bed3 bath8 parking

MLS® W14114964RE/MAX HALLMARK REALTY LTD.

6 Maple Grove Road, Caledon, ON L7K 0Z3

6 Maple Grove RoadCaledon, ON L7K 0Z3

Caledon · Caledon Village

3 + 2 bed2 bath8 parking

MLS® W13699698RE/MAX SPECIALISTS TAVSELLS INC.

23 Deer Valley Drive, Caledon, ON L7E 2E3

23 Deer Valley DriveCaledon, ON L7E 2E3

Caledon · Bolton West

4 bed4 bath6 parking

Renavu EstimateHigh

9% above our estimate

Estimated value: $1,099,000

MLS® W14121402RE/MAX REAL ESTATE CENTRE INC.

19 Mcconachie Crescent, Caledon, ON L7K 0B9

19 Mcconachie CrescentCaledon, ON L7K 0B9

Caledon · Rural Caledon

3 + 1 bed3 bath12 parking

Renavu EstimateHigh

15% above our estimate

Estimated value: $1,221,000

MLS® W13821904REAL ESTATE ADVISORS INC.

53 Marilyn Street, Caledon, ON L7C 1H5

53 Marilyn StreetCaledon, ON L7C 1H5

Caledon · Caledon East

3 + 1 bed3 bath6 parking

MLS® W14119216REAL BROKER ONTARIO LTD.

15 Caledon Mountain Drive, Caledon, ON L7K 0G1

15 Caledon Mountain DriveCaledon, ON L7K 0G1

Caledon · Rural Caledon

4 bed3 bath12 parking

MLS® W13768664REVEL REALTY INC.

7 Maple Meadow Court, Caledon, ON L7K 0G2

7 Maple Meadow CourtCaledon, ON L7K 0G2

Caledon · Rural Caledon

4 + 1 bed7 bath13 parking

MLS® W13744042HOUSESIGMA INC.

34 Boyces Creek Court, Caledon, ON L7C 3S2

34 Boyces Creek CourtCaledon, ON L7C 3S2

Caledon · Caledon East

4 + 1 bed4 bath6 parking

Renavu EstimateLow

12% above our estimate

Estimated value: $1,234,000

MLS® W13864934SUTTON GROUP REALTY SYSTEMS INC.

38 Gentle Fox Drive, Caledon, ON L7C 3S5

38 Gentle Fox DriveCaledon, ON L7C 3S5

Caledon · Rural Caledon

5 bed5 bath4 parking

MLS® W13841560RE/MAX PREMIER THE OP TEAM

4 Woodlot Court, Caledon, ON L7E 0C2

4 Woodlot CourtCaledon, ON L7E 0C2

Caledon · Palgrave

8 bed7 bath20 parking

MLS® W14115532RE/MAX EXPERTS

50 North Riverdale Drive, Caledon, ON L7C 3K3

50 North Riverdale DriveCaledon, ON L7C 3K3

Caledon · Inglewood

3 bed4 bath6 parking

MLS® W13805026RE/MAX REALTY SERVICES INC.

40 Walton Drive, Caledon, ON L7E 0A1

40 Walton DriveCaledon, ON L7E 0A1

Caledon · Palgrave

4 bed7 bath20 parking

MLS® W14112872TAILOR MADE REAL ESTATE INC.

20909 Shaws Creek Road, Caledon, ON L7K 1L7

20909 Shaws Creek RoadCaledon, ON L7K 1L7

Caledon · Alton

4 bed2 bath12 parking

MLS® W14091658CENTURY 21 MILLENNIUM INC.

15252 Chinguacousy Road, Caledon, ON L7C 1Z7

15252 Chinguacousy RoadCaledon, ON L7C 1Z7

Caledon · Rural Caledon

3 + 1 bed4 bath14 parking

MLS® W14031462RE/MAX GOLD REALTY INC.

7 Compton Court, Caledon, ON L7E 1L4

7 Compton CourtCaledon, ON L7E 1L4

Caledon · Bolton East

3 + 1 bed3 bath8 parking

MLS® W14089740ANALYST REALTY INC.

25 Mccandless Court, Caledon, ON L7C 3R6

25 Mccandless CourtCaledon, ON L7C 3R6

Caledon · Caledon East

4 bed4 bath4 parking

MLS® W14103128RE/MAX EXPERTS

6 Mccandless Court, Caledon, ON L7C 3R7

6 Mccandless CourtCaledon, ON L7C 3R7

Caledon · Caledon East

4 bed4 bath6 parking

Renavu EstimateHigh

8% above our estimate

Estimated value: $1,320,000

MLS® W14101702RE/MAX REALTY SPECIALISTS INC.

7735 Old Church Road, Caledon, ON L7E 0P5

7735 Old Church RoadCaledon, ON L7E 0P5

Caledon · Rural Caledon

3 + 1 bed5 bath16 parking

MLS® W14011644ROYAL LEPAGE RCR REALTY

62 Gibson Lake Drive, Caledon, ON L7E 4B2

62 Gibson Lake DriveCaledon, ON L7E 4B2

Caledon · Palgrave

3 + 1 bed5 bath15 parking

MLS® W12968958HOMELIFE/MIRACLE REALTY LTD

See all 64 in the full search →

Explore more of Caledon

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Nearby cities

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Mississauga183 for sale

Brampton86 for sale

Caledon neighbourhoods

Homes for sale in Caledon's busiest neighbourhoods.

Rural Caledon26 for sale

Palgrave13 for sale

Caledon East8 for sale

Bolton East4 for sale

Caledon Village4 for sale

Bolton West2 for sale

All neighbourhoods (11) →

Alton2 for sale

Inglewood2 for sale

Bolton North1 for sale

Cheltenham1 for sale

Mono Mills1 for sale

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