Caledon Homes With Pools

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House for sale: 1749 STATION ROAD, Caledon

50 photos

$2,790,000

1749 Station Road, Caledon (Rural Caledon), Ontario L7C 3L2

6 beds
5 baths
5 days

Cross Streets: King & Chinguacousy. ** Directions: North of King St between Chinguacousy & Creditview. Beautiful Bungalow with amazing views! A rare find, this custom built home in the sought-after Cheltenham community offers 3300sq ft upstairs and another 2600 sq ft downstairs, has soaring

Listed by: Kathy Tuitt ,Tailor Made Real Estate Inc. (416) 876-7355
House for sale: 12 GLENN COURT, Caledon

50 photos

$1,749,000

12 Glenn Court, Caledon (Rural Caledon), Ontario L7K 0P2

6 beds
3 baths
18 days

Airport Road/Collihans Side Road Welcome to the country escape everyone talks about but rarely finds. Tucked away on a private, quiet court in rural Caledon, this beautifully renovated home sits on 2.72 acres of pure tranquility, offering the perfect blend of modern comfort and peaceful country

Alex Cygal,Re/max Realty Services Inc.
Listed by: Alex Cygal ,Re/max Realty Services Inc. (416) 471-7475
House for sale: 11 MEADOW DRIVE, Caledon

50 photos

$1,499,999

11 Meadow Drive, Caledon (Caledon Village), Ontario L7K 1A2

4 beds
3 baths
12 days

Highway 10 and Charleston Sideroad Step into 11 Meadow, a breathtaking and very rare bungalow that feels like your own private resort. From the moment you enter the sunlit foyer, with its clean railings and natural light pouring in, the home sets a warm and welcoming tone. The space opens up

Mohan Khangura,Smartway Realty
Listed by: Mohan Khangura ,Smartway Realty (416) 417-9999
House for sale: 14294 WINSTON CHURCHILL BOULEVARD, Caledon

45 photos

$2,389,000

14294 Winston Churchill Boulevard, Caledon (Rural Caledon), Ontario L7C 3E8

4 beds
3 baths
55 days

Winston Churchill Boulevard / King Street In the storybook hamlet of Terra Cotta, Caledon, just steps from the Cataract Trailway and Terra Cotta Conservation Area, this exceptional property offers elegance and a deep connection to nature. Nearly 2.5 acres back onto protected conservation land

Lisa Hartsink,Coldwell Banker Elevate Realty
Listed by: Lisa Hartsink ,Coldwell Banker Elevate Realty (905) 873-9944
House for sale: 877 THE GRANGE SIDE ROAD, Caledon

49 photos

$1,830,000

877 The Grange Side Road, Caledon (Rural Caledon), Ontario L7C 0E4

6 beds
5 baths
28 days

Cross Streets: Mississauga Road and The Grange Side Road. ** Directions: West Of Mississauga Road. Experience the very best in one of the Caledon's most desirable neighbourhoods. Set on a beautifully treed 1 acre lot with stunning views, this custom detached brick home features 6 bedrooms and

Listed by: Varinder Kaur Singh (416) 740-5100
House for sale: 39 PINEBROOK CIRCLE, Caledon

50 photos

$1,499,900

39 Pinebrook Circle, Caledon (Rural Caledon), Ontario L7C 1C4

6 beds
5 baths
85 days

410 & Hurontario St. Discover an exceptional executive residence in one of Valleywood's most coveted neighbourhoods. This meticulously maintained 4+2 bedroom, 5-bath home offers over 3,000 sq. ft. above grade and a finished, walk-out basement apartment, ideal for extended family, rental income,

House for sale: 18754 HEART LAKE ROAD, Caledon

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$12,950,000

18754 Heart Lake Road, Caledon (Rural Caledon), Ontario L7K 1Z7

5 beds
6 baths
204 days

Cross Streets: Charleston Sideroad/Heart Lake Rd. ** Directions: Heart Lake S Of Beech Grove. A jaw-dropping architectural statement in the heart of Caledon! This one-of-a-kind residence blends world-class design, natural beauty & uncompromising craftsmanship across 10,300 square feet of living

House for sale: 43 OLIVERS LANE, Caledon

50 photos

$1,499,999

43 Olivers Lane, Caledon (Caledon East), Ontario L7C 1G5

4 beds
3 baths
31 days

Cross Streets: Olivers Lane & Walkers Rd. ** Directions: use gps. Step Into Style And Comfort With This Beautifully Renovated Detached Bungalow In Highly Sought-After Caledon East.. This Impressive Home Showcases Quality Upgrades Throughout, Featuring A Modern Kitchen With Quartz Countertops,

House for sale: 18805 WILLOGHBY ROAD, Caledon

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$1,840,000

18805 Willoghby Road, Caledon (Rural Caledon), Ontario L7K 1V7

5 beds
4 baths
234 days

Willoughby Rd/ Charelston Sdr ABSOLUTELY Gorgeous ! ! ! ! Excellent Location! Beautiful 4 +1 Bedroom , 4 Bathroom Home With A 3 Car Garage And Workshop Sits On A Gorgeously Landscaped 1 - Acre Lot. Once You Enter Everything Is Just Gorgeous! Living & Family Rooms are Enough To Gather Visitors

Listed by: Aman Angroya ,Homelife Silvercity Realty Inc. (905) 913-8500
House for sale: 88 WALKER ROAD W, Caledon

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$1,198,000

88 Walker Road W, Caledon (Caledon East), Ontario L7C 0G8

5 beds
3 baths
50 days

Cross Streets: Walker Rd & Airport Rd. ** Directions: From airport road head west on Walker Rd W. House is just past bridge on south side. Escape to a private 1 acre paradise in the heart of Caledon East. It isn't just a home; it's a lifestyle, offering a magical rural retreat with the convenience

Eran Williamson,Royal Lepage Rcr Realty
Listed by: Eran Williamson ,Royal Lepage Rcr Realty (416) 824-7685
House for sale: 12 KEVINWOOD DRIVE, Caledon

46 photos

$1,389,900

12 Kevinwood Drive, Caledon (Caledon Village), Ontario L7K 0Z1

5 beds
3 baths
8 days

Cross Streets: Hurontario St/Charleston Sdrd. ** Directions: google map. Welcome home to this Cozy 3 bedroom family gem . The upper level offers 3 spacious bedrooms, a 4-pc bath with heated floor. Primary BR with double closets. The main floor flows beautifully with ceramic tile from the entrance

Listed by: Robert David Ranieri ,Royal Lepage Certified Realty (905) 601-0587
House for sale: 16735 MISSISSAUGA ROAD, Caledon

44 photos

$1,999,000

16735 Mississauga Road, Caledon (Rural Caledon), Ontario L7K 1M8

3 beds
2 baths
7 days

Cross Streets: Mississauga Rd/The Grange Side Rd. ** Directions: The Grange & Mississauga Rd. Welcome to the historic hamlet of Belfountain. A unique Hamlet just north of the Village of Terra Cotta and offers residents and visitors the memorable experience of experiencing quaint shops & food

House for sale: 30 CEDAR DRIVE, Caledon

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$3,499,777

30 Cedar Drive, Caledon (Rural Caledon), Ontario L7K 1H6

4 beds
5 baths
65 days

Cross Streets: Forks of the Credit & Hwy 10. ** Directions: Hwy 10 & Forks of the Credit Rd. Welcome to Cedar Drive one of Caledon's most sought after estate style residential developments. Frank Lloyd Wright inspired, this Executive Style Bungaloft Is Perfect For The Outdoor Enthusiast who

House for sale: 9 FLAHERTY LANE, Caledon

49 photos

$6,399,000

9 Flaherty Lane, Caledon (Rural Caledon), Ontario L7K 2P2

6 beds
10 baths
14 days

Cross Streets: Dufferin Rd 109 & Porterfield Rd. ** Directions: Drive north on Porterfield Rd and take a left on Flaherty Lane to arrive at the property. Welcome to 9 Flaherty Lane, a breathtaking custom estate nestled on over 10.6 acres in one of Caledon's prestigious enclaves and backing

Sam Allan Mcdadi,Sam Mcdadi Real Estate Inc.
Listed by: Sam Allan Mcdadi ,Sam Mcdadi Real Estate Inc. (905) 502-1500
House for sale: 19996 HEART LAKE ROAD, Caledon

50 photos

$1,179,000

19996 Heart Lake Road, Caledon (Rural Caledon), Ontario L7K 2A1

3 beds
3 baths
9 days

Cross Streets: Highway 9. ** Directions: Intersection of Ontario Hwy 9 & 10. Travel East on Hwy 9, Turn South onto Heart Lake Road to 19996 Heart Lake Road. I would like to welcome you to 19996 Heart Lake Road in Caledon, where peaceful country living meets modern comfort on a beautifully private

Joe Goudreault,Royal Lepage Rcr Realty
Listed by: Joe Goudreault ,Royal Lepage Rcr Realty (519) 941-5151
House for sale: 19 MCCONACHIE CRESCENT, Caledon

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$1,619,000

19 Mcconachie Crescent, Caledon (Rural Caledon), Ontario L7K 0B9

4 beds
3 baths
19 days

Kennedy rd /Mcconachie Cres "Escape to your dream home in the countryside! This beautifully maintained raised bungalow sits on a sprawling 1.5-acre lot, offering peace and tranquility just a short drive from city conveniences. It provides the perfect blend of comfort, luxury, and functionality.-

Waqas Ahmad Syed,Homelife Paradise Realty Inc.
Listed by: Waqas Ahmad Syed ,Homelife Paradise Realty Inc. (905) 502-5800
House for sale: 34 ISABELLA STREET, Caledon

50 photos

$2,094,900

34 Isabella Street, Caledon (Rural Caledon), Ontario L7C 1N7

6 beds
5 baths
36 days

Winston Churchill / King St / Isabella Experience luxury living in this stunning custom-built bungalow designed for comfort and style having more than 4000sqft living space. Offering the perfect blend of functionality and sophistication. Step into the chef-inspired kitchen, featuring premium

Paal Wirring,Re/max Realty Services Inc.
Listed by: Paal Wirring ,Re/max Realty Services Inc. (905) 456-1000
House for sale: 26 ARCADIA ROAD, Caledon

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$1,449,000

26 Arcadia Road, Caledon (Rural Caledon), Ontario L7C 3V7

4 beds
5 baths
19 days

Cross Streets: Kennedy & Learmont. ** Directions: W12355121. This exceptional residence is offered fully furnished, presenting a rare opportunity to acquire a truly turnkey luxury home. Each piece has been thoughtfully curated to complement the design, creating a refined living experience.

Listed by: June Dias ,Royal Lepage Certified Realty (416) 741-4443
House for sale: 2814 FORKS OF THE CREDIT ROAD, Caledon

50 photos

$2,999,000

2814 Forks Of The Credit Road, Caledon (Rural Caledon), Ontario L7K 2H5

5 beds
6 baths
30 days

Cross Streets: Hurontario St & Forks of the Credit Rd. ** Directions: If heading northbound on Hurontario St, turn left onto Forks of the Credit Rd. If heading southbound on Hurontario St, turn right onto Forks of the Credit Rd. The property will be on your right side. Discover a truly unique

Sam Allan Mcdadi,Sam Mcdadi Real Estate Inc.
Listed by: Sam Allan Mcdadi ,Sam Mcdadi Real Estate Inc. (905) 502-1500
House for sale: 446 THE GRANGE SIDE ROAD, Caledon

49 photos

$5,850,000

446 The Grange Side Road, Caledon (Rural Caledon), Ontario L7K 1G4

4 beds
5 baths
1 day

Shaws Creek Rd / The Grange Side Rd Located in the heart of Caledon, 446 The Grange Side Road is situated on over 11 acres of wooded grounds and manicured open vistas. This exquisite, private country estate is the perfect blend of country flavour and contemporary design. Located in close proximity

House for sale: 15277 DIXIE ROAD, Caledon

50 photos

$1,749,000

15277 Dixie Road, Caledon (Rural Caledon), Ontario L7C 2N1

5 beds
4 baths
37 days

Dixie Rd / Olde Baseline Rd Beautifully Renovated Home on 1.5 Acres in Caledon. A Rare Opportunity to own a Stunning, Fully Renovated property on a nearly 1.5 Acres lot in Caledon, Just North of King Street on Dixie Road. This Home Features a Main-floor Bedroom and Full Washroom, With over

Karamjit Singh Dhaliwal,Index Realty Brokerage Inc.
Listed by: Karamjit Singh Dhaliwal ,Index Realty Brokerage Inc. (647) 917-9852
House for sale: 17397 HUMBER STATION ROAD, Caledon

49 photos

$2,389,900

17397 Humber Station Road, Caledon (Rural Caledon), Ontario L7E 3A6

4 beds
4 baths
204 days

HUMBER STATION/PATTERSON SDRD Welcome to 17397 Humber Station Road, A Private Retreat Surrounded by Nature Experience the rare opportunity to own a fully updated bungalow set on a breathtaking 24 acre estate, where privacy, serenity, and natural beauty come together in perfect harmony. Thoughtfully

House for sale: 15163 CENTREVILLE CREEK ROAD, Caledon

48 photos

$2,099,000

15163 Centreville Creek Road, Caledon (Rural Caledon), Ontario L7C 3C3

4 beds
5 baths
3 days

Cross Streets: Centreville Creek & Castlederg Sdrd. ** Directions: King St to Centreville Creek Rd, go North, just North of Castlederg. Welcome to your private Caledon estate, peacefully set on 34 picturesque acres offering the perfect blend of luxury, country living, functionality, and natural

House for sale: 19211 MOUNTAINVIEW ROAD, Caledon

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$1,400,000

19211 Mountainview Road, Caledon (Rural Caledon), Ontario L7K 2G6

4 beds
5 baths
5 days

Cross Streets: Beech Grove Sdrd/Mountainview Rd. ** Directions: Hwy 9 east, south on Mountainview Rd to below Beech Grove Sdrd. Enjoy pool days in every season - all from the comfort of home! Set on a beautiful 1-acre lot along a paved country road and surrounded by towering mature trees, this

Bradley Mayer-harman,Century 21 Millennium Inc.
Listed by: Bradley Mayer-harman ,Century 21 Millennium Inc. (647) 494-5387
House for sale: 38 MARILYN STREET, Caledon

50 photos

$1,749,999

38 Marilyn Street, Caledon (Caledon East), Ontario L7C 1H5

4 beds
4 baths
36 days

Old Church and Marilyn St. Rare Caledon East Private One Acre Retreat with Sun-Filled Great Room, Resort Pool & Easy GTA Access. Welcome to a home that feels like a private retreat-where light, space, and nature come together in perfect harmony. Set on over an acre and surrounded by mature

Listed by: Ross Vignale ,Re/max Realty Services Inc. (905) 702-4326
House for sale: 2097 GRANGE SIDE ROAD, Caledon

39 photos

$8,933,000

2097 Grange Side Road, Caledon (Rural Caledon), Ontario L7C 0E7

9 beds
9 baths
10 days

between creditview & mclaren One of Caledon's Most Spectacular Estates with Breathtaking Views of the Caledon Landscape and Toronto Skyline, this estate is the epitome of luxury living and grand entertaining. Featuring 9 bedrooms and 9 bathrooms, this magnificent home has been meticulously

Listed by: Paul Richardson ,Royal Lepage Meadowtowne Realty (905) 877-8262
House for sale: 15466 THE GORE ROAD, Caledon

40 photos

$16,800,000

15466 The Gore Road, Caledon (Rural Caledon), Ontario L7C 3E5

7 beds
9 baths
11 days

Cross Streets: Airport Rd/Old Church Rd. ** Directions: South of Old Church Rd. 15466 & 15430 Gore Road Stonebridge Estate. An Extraordinary, Fully Renovated Estate By Award-Winning Chatsworth Fine Homes With Interiors By Jane Lockhart Designs. Set In East Caledon, This Private 52.5-Acre Retreat

House for sale: 13450 HERITAGE ROAD, Caledon

50 photos

$1,499,995

13450 Heritage Road, Caledon (Rural Caledon), Ontario L7C 1T4

4 beds
3 baths
1 day

Cross Streets: Old School Rd/ Heritage. ** Directions: Google Maps. Idyllic Country Bungalow with all the Bells & Whistles. House is much larger-than-it-looks, thanks to a nice large addition. Bright open concept living area on main level. Hardwood, laminate, ceramic floors through the main

Michael Baron,Re/max Real Estate Centre Inc.
Listed by: Michael Baron ,Re/max Real Estate Centre Inc. (905) 877-5211
House for sale: 18387 THE GORE ROAD, Caledon

32 photos

$5,995,000

18387 The Gore Road, Caledon (Rural Caledon), Ontario L7E 0X8

5 beds
5 baths
1 day

Finnerty/The Gore/Hwy 9 Discover That Form A Private Paradise, This Stunning Property Boasts Over 10,000 Square Feet Of Gorgeous Living Space On Almost 25 Acres Of Prime Land. Lovingly Cared For And Kept in Perfect Shape, This One-Of-A-Kind Home Mixes Classic Charm With Timeless Beauty. Step

House for sale: 32 DOTCHSON AVENUE, Caledon

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$1,349,000

32 Dotchson Avenue, Caledon (Rural Caledon), Ontario L7C 4G6

4 beds
4 baths
9 days

Kennedy/Dotchson Set on an exceptional 212-ft deep pie-shaped, *Separate entrance by builder* pool-sized lot in the sought-after Southfields community, this stunning approximately 3-year-old executive home offers the perfect blend of luxury, space, and craftsmanship. A grand double-door entry

Onkar Cheema,Re/max Gold Realty Inc.
Listed by: Onkar Cheema ,Re/max Gold Realty Inc. (647) 981-7981
House for sale: 14812 CENTREVILLE CREEK ROAD, Caledon

22 photos

$1,649,000

14812 Centreville Creek Road, Caledon (Rural Caledon), Ontario L7C 3B1

5 beds
4 baths
11 days

King St & Centreville Creek Rd Discover the ideal harmony of tranquil country living and urban convenience in this meticulously maintained property in prestigious Caledon. This exceptional 3+2 bedroom, 4-bathroom home sits on a private 1-acre lot, offering luxury amenities and stunning natural

Mandeep Singh Dhesi,Re/max Excellence Real Estate
Listed by: Mandeep Singh Dhesi ,Re/max Excellence Real Estate (905) 507-4436
House for sale: 19982 KENNEDY ROAD, Caledon

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$1,375,000

19982 Kennedy Road, Caledon (Rural Caledon), Ontario L7K 1Y3

3 beds
3 baths
72 days

Cross Streets: Beech Grove/ Kennedy. ** Directions: from Hwy 24 turn north on Kennedy Rd, from Hwy 9 turn south on Kennedy RD. Nestled on a serene, tree-lined 1.03 acre in Caledon, this stunning 3-bedroom, 3-bathroom, residence offers of beautiful living space 2,104 sq. ft above grade + 900

Nancy Ackerman,Icloud Realty Ltd.
Listed by: Nancy Ackerman ,Icloud Realty Ltd. (519) 278-6813
House for sale: 24 ROYAL VALLEY DRIVE, Caledon

44 photos

$1,189,900

24 Royal Valley Drive, Caledon (Rural Caledon), Ontario L7C 1B2

5 beds
4 baths
17 days

Royal Valley/Valleywood Blvd. Welcome to this beautifully maintained, all-brick detached home in Caledon's sought-after Valleywood community - an ideal step-up into detached living or the perfect first family home. Set on an exceptional 142-ft deep lot, this property offers rare privacy with

Alex Cygal,Re/max Realty Services Inc.
Listed by: Alex Cygal ,Re/max Realty Services Inc. (416) 471-7475
House for sale: 2 TERRY STREET, Caledon

3 photos

$899,000

2 Terry Street, Caledon (Rural Caledon), Ontario L7K 0B1

3 beds
2 baths
46 days

Highway 10 & Terry St. Charming bungalow with a fully equipped workshop and exceptional exposure, ideal for commuters and home-based businesses. Conveniently located with quick access to a main road, close to GO Transit, and near Hwy 10 for maximum visibility. Situated on approximately half

Hardip Ghag,Re/max Real Estate Centre Inc.
Listed by: Hardip Ghag ,Re/max Real Estate Centre Inc. (416) 274-4115
House for sale: 57 KIRKWOOD CRESCENT, Caledon

45 photos

$1,399,900

57 Kirkwood Crescent, Caledon (Rural Caledon), Ontario L7C 1B8

6 beds
4 baths
52 days

Cross Streets: VALLEYWOOD BLVD AND HURONTARIO. ** Directions: Head north on Valleywood Blvd, turn right on Royal Valley Dr, then turn right on Kirkwood Cres. Welcome to this rare and beautifully maintained spacious bungalow in the sought-after community of Valleywood, surrounded by scenic trails,

Listed by: Alex Divac ,Right At Home Realty, Brokerage (905) 637-1700
House for sale: 65 PAISLEY GREEN AVENUE, Caledon

44 photos

$1,398,000

65 Paisley Green Avenue, Caledon (Caledon East), Ontario L7C 3S1

5 beds
4 baths
25 days

Cross Streets: Old Church & Innis Lake Rd. ** Directions: Old Church Road/ Innis Lake Rd. One of the happiest places to live! This is where lifestyle and location come together perfectly. Welcome to this stunning 5-bedroom home in the heart of Caledon East where comfort meets community. From

House for sale: 75 MARILYN STREET, Caledon

38 photos

$1,429,000

75 Marilyn Street, Caledon (Caledon East), Ontario L7C 1H7

5 beds
4 baths
40 days

Old Church Rd/Marilyn Street Welcome to 75 Marilyn Street, nestled in the heart of the close-knit & highly sought-after community of Caledon East-a place where neighbours become friends & families put down lasting roots. This beautifully updated 5-bedroom, 4-bathroom, carpet free home offers

Listed by: Sean Dylan Anderson ,The Richie Group Inc. (519) 942-0234
House for sale: 32 CALEDON STREET, Caledon

33 photos

$999,999

32 Caledon Street, Caledon (Alton), Ontario L7K 0E2

5 beds
3 baths
59 days

MAIN ST/QUEEN ST W Beautiful 3+2 Bedroom Bungalow with a WALK OUT BASEMENT!! Welcome to this stunning fully renovated bungalow nestled in the heart of Alton. This home features 3 spacious bedrooms on the main floor plus 2 full washrooms and a beautifully finished basement with 2 additional

Listed by: Manveer Singh Dhindsa ,Re/max Realty Services Inc. (905) 456-1000
House for sale: 50 ESPOSITO DRIVE, Caledon

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$1,359,900

50 Esposito Drive, Caledon (Bolton East), Ontario L7E 1T5

4 beds
4 baths
10 days

Queensgate/Albion-Vaughan Rd Rarely offered on one of Bolton's most sought-after streets, this exceptional 2-storey detached home sits in a quiet, family-friendly South Hill pocket. Showcasing impressive curb appeal, this 4-bedroom, 4-bathroom home offers a perfect blend of comfort, space,

Listed by: Dino Nunno (416) 690-2121
House for sale: 16568 MOUNT HOPE ROAD, Caledon

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$1,299,999

16568 Mount Hope Road, Caledon (Palgrave), Ontario L7E 5R8

5 beds
5 baths
21 days

Cross Streets: KING ROAD/TOWNLINE S CALEDON KING. ** Directions: TOWNLINE S CALEDON KING TO COLUMBIA WAY TO MOUNT HOPE ROAD. FULLY SERVICED RURAL RESIDENTIAL ESTATE PROPERTY****2.83 ACRES****3886 SQFT 2-STOREY HOUSE***INGROUND POOL***TRIPLE GARAGE****POND *****JUST WAITING FOR SOMEONE TO OFFER

Listed by: Andrea Vyner ,Right At Home Realty (905) 695-7888
House for sale: 110 PALMER CIRCLE, Caledon

43 photos

$1,677,500

110 Palmer Circle, Caledon (Palgrave), Ontario L7E 0A5

4 beds
4 baths
52 days

Cross Streets: North of Old Church B/W Hwy 50 & Mt Hope. ** Directions: palmer circle x walton dr. Set on a stunning estate-sized lot, this 4-bedroom, 4-bath residence offers over 3,500 sq ft of beautifully finished living space designed for both everyday comfort and elevated entertaining.

House for sale: 4 WOLF CRESCENT, Caledon

34 photos

$2,139,900

4 Wolf Crescent, Caledon (Palgrave), Ontario L7E 0A7

4 beds
3 baths
10 days

Cross Streets: Old Church Rd & Mount Hope Rd. ** Directions: Corner of Wolf Crescent & Matson Drive. Set on an impressive 2.5-acre corner lot, 4 Wolf Crescent offers an incredible opportunity in one of Caledon's most sought-after areas. With expansive, usable land and uninterrupted views in

House for sale: 73 WRIGHT CRESCENT, Caledon

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$1,250,000

73 Wright Crescent, Caledon (Bolton North), Ontario L7E 3X6

5 beds
4 baths
7 days

Cross Streets: Humberlea Rd / Kingsview Dr. ** Directions: On HW50 turn King street east and then turn Humberlea rd north. Fabulous Family Sized Home, Huge Finished Basement, True Double Garage. Premium 50 Ft x 140 Ft Lot On Bolton's Coveted North Hill With Cultivated Landscape, Stunning Kidney

Listed by: Nikolay Lyashov ,Icloud Realty Ltd. (416) 364-4776
House for sale: 12 BERRYDOWN DRIVE, Caledon

50 photos

$1,288,000

12 Berrydown Drive, Caledon (Bolton East), Ontario L7E 1L8

5 beds
4 baths
10 days

Cross Streets: Whitbread Ave & Pembrook St. ** Directions: See Google Maps. Welcome to this fully renovated 4+1 bed, 4 bath home with finished basement & inground pool, thoughtfully updated from top to bottom with modern finishes & a functional open concept design. Perfect for multi-generational

Francesca Valente,Re/max West Realty Inc.
Listed by: Francesca Valente ,Re/max West Realty Inc. (416) 436-4829
House for sale: 62 GIBSON LAKE DRIVE, Caledon

50 photos

$2,199,000

62 Gibson Lake Drive, Caledon (Palgrave), Ontario L7E 4B2

4 beds
5 baths
10 days

Cross Streets: Hwy 50 / Gibson Lake Dr. ** Directions: Please Check Google Map for direction. Thank you. LUXURIOUS ESTATE on 3.937 ACRES Lot in prestigious PALGRAVE community. Property features very Spacious 4 Car Garage (2 Attached & 2 Detached- Perfect for Boat storage or Pickup truck), Huge

Jagat Patel,Homelife/miracle Realty Ltd
Listed by: Jagat Patel ,Homelife/miracle Realty Ltd (647) 669-0331
House for sale: 3 BOWES Court, Caledon

50 photos

$1,445,000

3 Bowes Court, Caledon, Ontario L7E 1A5

6 beds
4 baths
5 days

150-Chickadee-DeRose - Bowes Spacious and well-appointed large 2-storey home offering exceptional move-in versatility for large families and multi-generational living. This large 4+bedroom, 4-bath residence features a bright, open layout with many improvements. The fully finished, carpet-free

Andy Tulloch,Century 21 Heritage House Ltd
Listed by: Andy Tulloch ,Century 21 Heritage House Ltd (519) 771-2095
House for sale: 26 WRIGHT CRESCENT, Caledon

39 photos

$1,119,000

26 Wright Crescent, Caledon (Bolton North), Ontario L7E 3X9

3 beds
2 baths
96 days

Cross Streets: Kingsview/ Wright Cres. ** Directions: Hwy 50/ Bolton Heights/ Kingsview to Wright Cres. Brand New Cistom kitchen! This beauty willl not last! Fully renovated home on one of the best streets in the North Hill. This huge cornet lot on a quiet crescent boasts a very spacious, fully

Laura Elizabeth Smith,Lpt Realty
Listed by: Laura Elizabeth Smith ,Lpt Realty (416) 660-1115
House for sale: 26 WRIGHT CRESCENT S, Caledon

45 photos

$1,099,000

26 Wright Crescent S, Caledon (Bolton North), Ontario L7E 3X9

4 beds
2 baths
16 days

Cross Streets: Kingsview/Wright. ** Directions: Hwy 50/Bolton Heights. Brand New Custom kitchen! This beauty will not last! NEW PRICE and MOTIVATED SELLER! Fully renovated home on one of the best streets in the North Hill. This huge cornet lot on a quiet crescent boasts a very spacious, fully

Laura Elizabeth Smith,Lpt Realty
Listed by: Laura Elizabeth Smith ,Lpt Realty (416) 660-1115
House for sale: 187 HICKMAN STREET, Caledon

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$1,268,000

187 Hickman Street, Caledon (Bolton West), Ontario L7E 2P5

4 beds
3 baths
8 days

Highway 50/King Street 187 Hickman Street in Bolton. 1500 sqft of above-grade living space, nestled on a quiet court, in the exclusive "Valley" neighbourhood. Stunning raised bungalow on a premium deep ravine lot, backing onto protected Conservation Land. Breathtaking Humber River Valley views

Listed by: Sophie Alegra Giterman ,Easy List Realty Ltd. (888) 323-1998
House for sale: 100 HUMBER LEA ROAD, Caledon

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$1,019,000

100 Humber Lea Road, Caledon (Bolton North), Ontario L7E 3T7

4 beds
2 baths
80 days

Cross Streets: King & Humber Lea Rd. ** Directions: King and Humber Lea Road. Welcome to Prestigious North Hill, Bolton!Stunning, fully updated 3+1 bdrm bungalow on an impressive 80-ft lot with a resort-style saltwater pool. Bright open-concept layout features new flooring, a designer kitchen

Listed by: Joe Bilotta ,Right At Home Realty (905) 665-2500

Caledon house pool: practical guidance for GTA buyers and investors

For many Greater Toronto Area families, a Caledon house pool blends suburban convenience with rural elbow room. Before you picture summer cannonballs, it pays to understand how zoning, conservation overlays, maintenance costs, and market timing interact in this part of Peel Region. As a licensed Canadian real estate advisor, I see pool ownership deliver real lifestyle value—yet the best outcomes come from careful due diligence. Resources like KeyHomes.ca help you benchmark pool-friendly listings and market data across Ontario and beyond.

Lifestyle appeal and seasonal market timing

Caledon's outdoor pool season typically spans late May to early September, with shoulder-season swimming possible using heaters and solar covers. Families choose pools for at-home recreation, while move-up buyers and multi-generational households value the yard privacy common in Caledon East, Palgrave, and along the Old School Road corridor. It's no surprise that listing headlines sometimes read like “welcome to Paul's Old School Road”—the setting can be as compelling as the pool.

Market-wise, the most active window for homes with pools is spring through midsummer. Sellers often open and showcase the pool by Victoria Day. Winter purchases are feasible, but plan for limited pool inspections when covered or winterized. Protect yourself with a holdback (often $5,000–$15,000) pending a satisfactory spring opening and equipment test.

Caledon zoning, permits, and conservation overlays

In Ontario, municipalities regulate pool enclosures and related permits. The Town of Caledon typically requires a pool enclosure permit, compliant fencing (often at least 1.5–1.8 m), self-closing, self-latching gates, and prescribed setbacks from lot lines and utilities. If your property lies within the Niagara Escarpment Commission area, Oak Ridges Moraine, Greenbelt, or a conservation authority's regulated zone (e.g., Credit Valley or Toronto and Region Conservation), extra approvals or prohibitions can apply—especially near floodplains, woodlots, and watercourses.

Buyer takeaway: requirements vary by location and evolve. Verify current bylaws and conservation mapping at the Town of Caledon and relevant authorities before committing to build, relocate equipment, or add features like cabanas.

Septic, well, and rural services: what to verify

Many Caledon properties outside built-up areas rely on private wells and septic systems. Pools and patios cannot encroach on septic infrastructure; expect minimum clearances from tanks and leaching beds, typically in the 3–5 m range (confirm locally). Heavy equipment for pool construction can damage septic fields if access isn't planned. Test the well's flow rate and water quality (for residences, not pool water) and consider the impact of pool fills on water supply—trucking water is common.

Heating often means natural gas where available; otherwise, propane or electric heat pumps are typical. Propane costs can fluctuate; factor delivery schedules and tank placement into your plan.

Costs: installation, operation, and lifecycle maintenance

In-ground pools vary widely by size, material (vinyl, fiberglass, concrete), and landscaping complexity. Budget ranges can span from the mid–five figures into six figures for premium hardscaping and safety covers. Seasonal operating costs in Southern Ontario commonly include chemicals, cleaning, and energy; opening/closing services can add $400–$800 per cycle. Salt systems reduce weekly handling but don't eliminate maintenance. Expect liners and equipment (heaters, pumps) to require replacement on normal lifecycles; review installation dates and warranties.

Indoor pools are rare in Caledon but do appear on estate properties. They demand building-science attention—vapor barriers, dedicated HVAC and dehumidification, and corrosion-resistant materials. To see how other markets price and present them, compare Toronto homes with indoor pools or even indoor pool options in Edmonton. West-coast climates can differ; browsing BC indoor pool homes offers additional perspective.

Insurance, liability, and safety

Insurers often require compliant fencing, self-latching gates, and may restrict diving boards or slides. Expect higher premiums and higher personal liability coverage (commonly $2 million or more). Non-compliant installations can void coverage. Ask for the seller's current insurance certificates and any claims history related to the pool area.

Financing and appraisal nuances

Lenders usually treat pools as part of the real property; appraisal adjustments depend on local comparables. In shoulder seasons when the pool is closed, appraisers may apply conservative adjustments. If safety deficiencies are noted (e.g., fence not to code), the lender may require repairs before closing or a solicitor-held holdback. For renovations, purchase-plus-improvements programs can sometimes fund a new pool, but disbursement timing and contractor milestones matter; confirm lender policies in writing.

Scenario: a buyer agrees to purchase a Palgrave property in February. The appraiser notes an older heater and an unverified fence. The buyer's lawyer negotiates a $10,000 holdback, released after a May inspection confirms a functioning system and a passed fence inspection. This protects both lender and buyer without delaying closing.

Resale potential and who values a pool

In Caledon, pools tend to boost appeal for family buyers seeking staycation-ready yards, especially when paired with usable lawn, west-facing exposure, and a practical change room. However, some buyers with toddlers avoid pools, and others balk at maintenance. Well-maintained, code-compliant installations with modern safety covers and efficient heaters generally achieve the best resale response. Staging the pool area with clear maintenance records, energy bills, and service contracts helps.

Investors eyeing multi-generational rentals or longer-term tenancies may find a pool enhances retention; short-term rental (STR) investors should proceed carefully. Local and regional bylaws around STRs continue to evolve across Ontario; some municipalities restrict or require licensing. Confirm current Town of Caledon rules and any condominium or community covenants before underwriting income assumptions.

Regional comparisons and price discovery

Benchmarking outside the GTA can clarify value. For instance, per-season operating costs and pricing for Belleville pool homes in Eastern Ontario or Brockville properties with pools often differ from Peel Region. Southwestern Ontario markets such as Brantford houses with pools or Welland pool listings can offer additional comparables. Even further afield, checking pool homes in Sault Ste. Marie or monitoring the Moose Jaw pool home market provides national context on pricing and seasonality.

Closer to home, if you're weighing Caledon against similar suburban settings, it's useful to scan Brampton inground pool listings. The comparison helps isolate how lot size, conservation constraints, and commute patterns influence pool-home premiums.

Neighbourhood notes and micro-locations

Bolton offers established subdivisions with manageable commutes, while Caledon East and Palgrave present larger lots and more frequent well/septic systems. Belfountain and the escarpment-side pockets are scenic but often more regulated due to terrain and conservation overlays. Along the Old School Road axis, larger parcels and estate-style construction are common—very different from compact suburban lots where side-yard equipment placement can be tight.

Noise and privacy matter: pool equipment pads and heaters should be sited to minimize noise carry to neighbours, and fencing/landscaping should respect sightlines. Where a property abuts a ravine or managed forest, consult conservation mapping before expanding decks or patios.

Working files, disclosures, and what to request from sellers

  • Pool enclosure permit, final inspection, and any conservation or NEC approvals (if applicable).
  • Drawings showing pool, equipment, and setbacks; confirm distance to septic tanks and beds.
  • Service logs: opening/closing reports, chemical regime, heater and pump installation dates.
  • Warranty documents and any transferable service contracts.
  • Insurance confirmations and any prior incident reports.

KeyHomes.ca is a reliable place to explore pool-equipped listings and research neighbourhood-level trends; the site also connects readers with licensed professionals for local verification. Whether you're Harsimran Sira, Karyna Gongalskyy, Berenia Torres, or simply comparing options across the GTA, neutral market context helps you separate a photogenic backyard from one that's sound, compliant, and financially sensible.

Common buyer questions, answered

Does a pool increase property taxes? MPAC assessments consider overall market value; a pool can contribute but not always dollar-for-dollar. Ask your appraiser and review recent sales of similar Caledon homes with pools.

What about winter risks? Proper closing (blowing out lines, lowering water, winterizing equipment) and a secure cover are key. Consider a contingency fund for spring start-up issues, particularly on older systems.

Can I add a pool post-purchase? Usually, yes—subject to zoning, conservation approvals, and setbacks. Confirm underground utilities, septic layout, and tree-protection requirements before signing with a contractor. Ask about workmanship warranties; unlike new-home Tarion coverage, third-party pool warranties vary.

Subtle differences that affect value

Sun exposure (south/west-facing yards extend swim time), wind patterns (windbreaks reduce heat loss), and equipment efficiency (variable-speed pumps, heat pumps) all influence enjoyment and cost. Safety features like four-sided isolation fencing and ASTM-rated safety covers resonate with family buyers and insurers alike. Finally, sightlines from the kitchen or family room to the pool improve day-to-day usability and can help at resale.