Caledon Homes With Pools

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House for sale: 18250 DUFFY'S LANE, Caledon

50 photos

$5,499,000

18250 Duffy's Lane, Caledon (Rural Caledon), Ontario L7E 3C4

4 beds
4 baths
22 days

Duffy's Lane & Finnerty Sideroad Extraordinary Caledon estate where privacy, a tranquil setting, natural beauty, and endless opportunity come together on approximately 86 spectacular acres. Tucked away among the rolling hills, this remarkable property offers an exceptional blend of open pasture,

House for sale: 20511 MAIN STREET, Caledon

50 photos

$1,990,000

20511 Main Street, Caledon (Rural Caledon), Ontario L7K 1R5

6 beds
5 baths
53 days

Cross Streets: MAIN ST/HIGHPOINT RD. ** Directions: HIGH POINT/MAIN ST. NORTH OF ALTON. Beautifully crafted custom-built bungalow nestled on a spectacular 1.4-acre estate lot, thoughtfully designed with an open-concept layout and a setting that feels as though it was sculpted into the surrounding

Listed by: Kiruja Sivarajah ,Harvey Kalles Real Estate Ltd. (416) 441-2888
House for sale: 5 MASSARI STREET, Caledon

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$1,685,000

5 Massari Street, Caledon (Caledon Village), Ontario L7K 0B6

4 beds
3 baths
60 days

Kennedy Rd., and Charleston Sdrd. Welcome to this beautifully renovated bungalow in the heart of Caledon Village, offering the perfect blend of modern comfort and country charm. Situated on over half acre of meticulously landscaped property, this exceptional home features 3+1 spacious bedrooms

House for sale: 16735 MISSISSAUGA ROAD, Caledon

44 photos

$1,750,000

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

3 beds
2 baths
98 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: 4314 BEECH GROVE SIDE ROAD, Caledon

35 photos

$1,849,900

4314 Beech Grove Side Road, Caledon (Caledon Village), Ontario L7K 0M4

5 beds
3 baths
3 days

Heartlake Rd/Beech Grove Set on a spectacular and private 1-acre lot surrounded by rolling hills and mature greenery, this exceptional country property offers the perfect blend of luxury, comfort, and versatility. Featuring 4+1 bedrooms and 3 bathrooms, this beautifully finished home showcases

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
51 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: 9 FLAHERTY LANE, Caledon

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$6,399,000

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

6 beds
10 baths
31 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: 12806 MISSISSAUGA ROAD, Caledon

41 photos

$1,499,000

12806 Mississauga Road, Caledon (Rural Caledon), Ontario L7C 1W2

4 beds
3 baths
20 days

Mayfield/Mississauga Road Set on a half-acre lot (100 x 219 ft) along Mississauga Rd between Mayfield and Old School, this two-storey detached home offers 4,250+ sq ft of total living space, 3,000 of it above grade. The main and upper levels were rebuilt in 2011 (plumbing, electrical and HVAC

House for sale: 7848 CASTLEDERG SIDE ROAD, Caledon

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$1,499,000

7848 Castlederg Side Road, Caledon (Rural Caledon), Ontario L7E 0R8

4 beds
2 baths
39 days

The Gore Rd & Castlederg A 1600 Sqft Commercial Workshop Plus Office. Zoned A1-452 For Motor Vehicle Repair Facility. Approved Workshop Features An Office Waiting Area, Hydraulic Car Lift, 2 Oversized Bay Doors & Heated And Insulated. Perfect For Car, Truck Or Motorcycle Repair Shop. Well Maintained

House for sale: 12 KEVINWOOD DRIVE, Caledon

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$1,339,900

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

5 beds
3 baths
54 days

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

Listed by: Robert David Ranieri ,Royal Lepage Certified Realty (905) 601-0587
House for sale: 446 THE GRANGE SIDE ROAD, Caledon

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$4,750,000

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

4 beds
5 baths
9 days

Shaws Creek Rd / The Grange Side Rd Located in one of the most desirable pockets 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 character and contemporary design.

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
325 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: 2 TERRY STREET, Caledon

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$899,000

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

3 beds
2 baths
137 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: 15277 DIXIE ROAD, Caledon

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$1,749,000

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

5 beds
4 baths
128 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: 19 JEAN STREET, Caledon

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$1,639,000

19 Jean Street, Caledon (Caledon East), Ontario L7C 1P7

4 beds
3 baths
36 days

Airport/Cranston Rare Caledon East Estate Lot | Nearly 1 Acre | Endless Possibilities Opportunities like this are becoming increasingly rare. Nestled on a spectacular pie shaped lot approaching one acre in one of Caledon East's most established and sought after neighbourhoods, this executive

John Cobley,Property.ca Inc.
Listed by: John Cobley ,Property.ca Inc. (416) 583-1660
House for sale: 19211 MOUNTAINVIEW ROAD, Caledon

42 photos

$1,349,900

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

4 beds
5 baths
39 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: 13289 INNIS LAKE ROAD, Caledon

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$8,000,000

13289 Innis Lake Road, Caledon (Rural Caledon), Ontario L7C 2Z6

5 beds
5 baths
58 days

Cross Streets: Healey Rd and Innis Lake Rd. ** Directions: Innis Lake Rd Between Healey Rd and King St. Exceptional 10-acre country estate offering privacy, versatility, and outstanding lifestyle amenities. This spacious 2-storey brick home features a renovated kitchen (2022) with large island,

House for sale: 53 MARILYN STREET, Caledon

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$1,199,990

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

4 beds
3 baths
45 days

Airport Rd & Old Church Welcome to 53 Marilyn Street, an exceptional opportunity to own a beautifully maintained detached home on a premium corner lot in one of Caledon East's most coveted family neighbourhoods. Surrounded by mature trees and prestigious homes, this property offers the perfect

Nik Handa,Real Broker Ontario Ltd.
Listed by: Nik Handa ,Real Broker Ontario Ltd. (647) 404-4083
House for sale: 5 VALLEYGREEN CRESCENT S, Caledon

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$1,567,000

5 Valleygreen Crescent S, Caledon (Caledon East), Ontario L7C 1J3

5 beds
4 baths
78 days

AIRPORT & MOUNTCREST Welcome to a home that truly elevates everyday living. Set on a beautifully private almost half-acre lot in one of Caledon East's most desirable enclaves, this fully renovated residence with over $120,000.00 spent and over 3500 SF of total living space offers a rare combination

House for sale: 25 HILLTOP DRIVE, Caledon

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$1,199,000

25 Hilltop Drive, Caledon (Caledon East), Ontario L7C 1H6

4 beds
2 baths
57 days

Airport Rd/Hilltop Drive Welcome to Hilltop Drive. One of Caledon East's most desirable communities. This beautifully updated 4-level side-split offers the ideal blend of modern style, space, and functionality. Featuring four bedrooms and four distinct living levels, this home has been thoughtfully

Anna Fitzcharles,One Percent Realty Ltd.
Listed by: Anna Fitzcharles ,One Percent Realty Ltd. (416) 858-5657
House for sale: 13 MCKEE DRIVE, Caledon

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$1,399,995

13 Mckee Drive, Caledon (Caledon East), Ontario L7C 1G8

4 beds
4 baths
53 days

Cross Streets: Airport Road and Walker. ** Directions: Airport Rd to Walker; East on Walker; Left onMcKee. OPEN HOUSE - SUNDAY JULY 26TH 2PM TO 4PM * The perfect home for summer, this executive residence is ideally located in the heart of Caledon East. Offering four spacious bedrooms and three

Peter Ramon Droog,Royal Lepage Meadowtowne Realty
Listed by: Peter Ramon Droog ,Royal Lepage Meadowtowne Realty (647) 282-5010
House for sale: 6 MAPLE GROVE ROAD, Caledon

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$1,389,000

6 Maple Grove Road, Caledon (Caledon Village), Ontario L7K 0Z3

5 beds
2 baths
51 days

East on Charleston & Hwy 10 Welcome to this charming fully renovated bungalow located in the desirable and family-friendly community of Caledon Village. This carpet-free home features a bright and spacious living room with a custom built-in media wall and LED lighting, along with cozy fireplaces

Listed by: Rohit Dogra ,Re/max Real Estate Centre Inc. (905) 456-1177
House for sale: 2 CEDAR DRIVE, Caledon

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$1,999,999

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

5 beds
3 baths
43 days

Cross Streets: Hwy 10 & Forks of the Credit Road. ** Directions: Hwy 10 to Forks of the credit road. Beneath the sweeping branches of a magnificent willow tree, where a spring-fed pond glistens with lily pads and a charming bridge leads to its own secluded island, life begins to slow down.

House for sale: 2097 GRANGE SIDE ROAD, Caledon

39 photos

$7,600,000

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

9 beds
9 baths
30 days

Between Creditview Rd. & Mclaren Rd. 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: 7 MCKEE DRIVE, Caledon

48 photos

$1,465,000

7 Mckee Drive, Caledon (Caledon East), Ontario L7C 1G8

3 beds
4 baths
26 days

Cross Streets: Airport Road and Old Church Road. ** Directions: Follow your GPS. Set on an impressive 83.78 x 177.49 ft estate lot in one of Caledon East's most coveted enclaves, this beautifully renovated executive residence offers timeless elegance, exceptional craftsmanship and resort inspired

Stephanie Simone,Sotheby's International Realty Canada
Listed by: Stephanie Simone ,Sotheby's International Realty Canada (416) 827-3071
House for sale: 8 VISTA VIEW COURT, Caledon

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$1,249,900

8 Vista View Court, Caledon (Rural Caledon), Ontario L7C 1E1

4 beds
4 baths
24 days

Cross Streets: HWY 10 & Valleywood. ** Directions: 410-NValleywood Rd,R-RoyalValley, R-Garden Wood, R-Vista View. This bungalow offers over 3,300 sq. ft. of finished living space with a separate entrance, making it ideal for multi-generational living or income potential. Located on a quiet

Listed by: Carol Lynn Carter ,Keller Williams Portfolio Realty (416) 579-2803
House for sale: 25 MCCANDLESS COURT, Caledon

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$1,399,000

25 Mccandless Court, Caledon (Caledon East), Ontario L7C 3R6

4 beds
4 baths
10 days

Cross Streets: innis lake/old church. ** Directions: off paisley green. Welcome To 25 McCandless Court, A Stunning 4-Bedroom, 4-Bathroom Home In One Of Caledon East's Most Sought-After Neighbourhoods. Thoughtfully Designed For Both Functionality And Elegance, This Spacious Property Offers 9-Foot

Stuart Sinclair,Re/max Experts
Listed by: Stuart Sinclair ,Re/max Experts (905) 499-8800
House for sale: 4780 ESCARPMENT SIDE ROAD, Caledon

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$10,900,000

4780 Escarpment Side Road, Caledon (Rural Caledon), Ontario L7C 2S1

7 beds
5 baths
25 days

Escarpment & St. Andrews Road WOODLANDS is an extraordinary 7-bedroom, 5-bathroom estate offering two distinct residences set on approximately 63 private acres of mature forest, scenic trails, and meticulously landscaped gardens. Perfectly positioned at the prestigious corner of Escarpment

House for sale: 16718 CALEDON KING TOWNLINE N, Caledon

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$2,998,000

16718 Caledon King Townline N, Caledon (Palgrave), Ontario L7E 3R5

5 beds
2 baths
60 days

HWY 9 / Caledon King Townline N Welcome To 16718 Caledon King Townline N An Exceptional Opportunity To Own A Private Country Estate On Nearly 25 Acres In Prestigious Palgrave. Tucked Behind A Gated Entrance And Surrounded By Mature Trees, This Remarkable Property Offers The Perfect Blend Of

Denise Gottardo,Re/max Millennium Real Estate
Listed by: Denise Gottardo ,Re/max Millennium Real Estate (905) 265-2200
House for sale: 23 DEER VALLEY DRIVE, Caledon

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$1,299,000

23 Deer Valley Drive, Caledon (Bolton West), Ontario L7E 2E3

4 beds
4 baths
51 days

Cross Streets: Deer Valley & King Street W. ** Directions: King Street W to Deer Valley Drive. Welcome to 23 Deer Valley Drive, a beautifully maintained all brick family home set on a premium 142 foot deep lot in one of Bolton's most established family neighbourhoods. Lovingly cared for by

Janine Speirs,Re/max Real Estate Centre Inc.
Listed by: Janine Speirs ,Re/max Real Estate Centre Inc. (647) 964-3307
House for sale: 32 CALEDON STREET, Caledon

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$959,999

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

5 beds
3 baths
51 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: 62 GIBSON LAKE DRIVE, Caledon

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$1,999,999

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

4 beds
5 baths
53 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: 110 PALMER CIRCLE, Caledon

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$1,600,000

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

4 beds
4 baths
73 days

Cross Streets: North of Old Church B/W Hwy 50 & Mt Hope. ** Directions: OLD CHURCH TO WALTON DR X PALMER CIRCLE. 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

House for sale: 33 GIBSON LAKE DRIVE, Caledon

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$2,149,000

33 Gibson Lake Drive, Caledon (Palgrave), Ontario L7E 4B3

3 beds
4 baths
70 days

Cross Streets: Hwy 50/ Gibson Lake Dr. ** Directions: Hwy 50 and Gibson Lake. Nestled in the rolling hills of Caledon, this stunning Palgrave residence offers the perfect balance of rural tranquility and upscale living. Renowned for its scenic beauty, spacious properties, and welcoming community,

Listed by: Joseph Anthony Muscatello ,Prospect Realty Inc. (905) 850-8220
House for sale: 6 COUNTRY LANE DRIVE, Caledon

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$2,399,000

6 Country Lane Drive, Caledon (Palgrave), Ontario L7E 0B4

6 beds
6 baths
38 days

Old Church/Mt Hope/Cedar Meadows Ln This Custom-Built Caledon Estate Sitting On 3.74 Acres Of Manicured Grounds, Offering Unmatched Privacy, Breathtaking Presence, And A Lifestyle Reserved For The Exceptional. Completely Transformed With A Newly Redone Exterior Façade, Fresh Concrete Work,

House for sale: 9 MORAINE PLACE, Caledon

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$2,199,000

9 Moraine Place, Caledon (Palgrave), Ontario L7E 0E5

3 beds
4 baths
36 days

Highway 50 - Finnerty Sideroad - Moraine Place Exceptional custom bungalow nestled on nearly 2 acres in one of Caledon's most prestigious executive enclaves. Set back from the road with a long private driveway, this remarkable property offers the perfect blend of luxury, privacy & convenience,

House for sale: 17 SHANGRILA TERRACE, Caledon

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$1,249,900

17 Shangrila Terrace, Caledon (Bolton West), Ontario L7E 2N2

5 beds
4 baths
29 days

Cross Streets: Queen St N and Cross Country Blvd. ** Directions: Queen St N to Cross Country Blvd turn left. Turn right at Shangrila Terrace. This two-storey, 4-bedroom, 4-bathroom home with a finished walkout basement is a real crowd-pleaser. Situated in the Humber Meadows executive subdivision

Sandy Hopkinson,Century 21 Heritage Group Ltd.
Listed by: Sandy Hopkinson ,Century 21 Heritage Group Ltd. (905) 866-9443
House for sale: 1510 STATION ROAD, Caledon

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$999,900

1510 Station Road, Caledon (Cheltenham), Ontario L7C 3M2

4 beds
2 baths
18 days

Creditview/Station Road Welcome to 1510 Station Road, a beautifully updated home in the heart of Cheltenham, set on a rare 0.344-acre lot (~15,000 sq. ft.) surrounded by gardens, mature landscaping, and outdoor living spaces designed to be enjoyed year-round. Offering updated 4 bedrooms & 2

Listed by: Jyoti Pannu ,Re/max Millennium Real Estate (905) 265-2200
House for sale: 4 WOLF CRESCENT, Caledon

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$1,999,900

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

4 beds
3 baths
54 days

Cross Streets: Old Church Rd. & Mount Hope Rd. ** Directions: Corner of Wolf Cres & 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 every

House for sale: 8 COATES HILL COURT, Caledon

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$2,969,000

8 Coates Hill Court, Caledon (Palgrave), Ontario L7E 0N4

5 beds
5 baths
67 days

Mount Pleasant/Old Church Gorgeous Property! Welcome to 8 Coates Hill Crt in Palgrave Estates. This house has 5 bedrooms, 5 bath over 5700 sq.ft of living space. The home boasts meticulously maintained grounds featuring low-maintenance perennial gardens and expansive hardscaping. The award-winning

Listed by: Kiritpal Grewal ,Homelife Maple Leaf Realty Ltd. (416) 388-2993
House for sale: 258 AMOS DRIVE, Caledon

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$3,588,000

258 Amos Drive, Caledon (Palgrave), Ontario L7E 4L7

4 beds
5 baths
57 days

HWY 9 & Mount Pleasant Welcome To 258 Amos Drive-Luxury Estate On a Conservation-Backed Lot. Welcome To This Stunning 4-Bedroom , 5-Bathroom estate nestled on a Premium 183 X 758 Ft Lot with breathtaking , unobstructed views . Perfect for relaxation or entertaining, The backyard is private

Listed by: Natalia Belykh ,Tfn Realty Inc. (416) 789-0288
House for sale: 57 KENNEDY Road, Caledon

49 photos

$2,500,000

57 Kennedy Road, Caledon, Ontario L7C 2M7

4 beds
7 baths
47 days

Creditview to Kennedy Road Experience the perfect balance of luxury, nature, and convenience. This property will appeal to the discerning buyer seeking something truly special. Inside 6,500 square feet of thoughtfully blends open-concept living with cozy private retreats. Nestled on a unique,

Karen Hewson,Keller Williams Edge Realty
Listed by: Karen Hewson ,Keller Williams Edge Realty (905) 464-2744
House for sale: 57 KENNEDY ROAD, Caledon

41 photos

$2,500,000

57 Kennedy Road, Caledon (Cheltenham), Ontario L7C 2M7

4 beds
6 baths
46 days

Cross Streets: Creditview & King. ** Directions: Creditview Road to Kennedy Road. Experience the perfect balance of luxury, nature, and convenience. This property will appeal to the discerning buyer seeking something truly special. Inside 6,500 square feet of thoughtfully blends open-concept

Karen Hewson,Keller Williams Edge Realty
Listed by: Karen Hewson ,Keller Williams Edge Realty (905) 335-8808
House for sale: 22 ASHBURY CRESCENT, Caledon

50 photos

$1,399,900

22 Ashbury Crescent, Caledon (Bolton East), Ontario L7E 1X6

6 beds
4 baths
30 days

Cross Streets: Queensgate & Pembrook. ** Directions: hwy 50 to Albion Vaughan Rd. Pride of ownership shines throughout this updated, custom-built Grand Brook home offering ~2,400 sq.ft. above grade. Situated on a premium, landscaped oversized pie-shaped lot with an impressive 100-ft frontage,

Angela Morra,Web Max Realty Inc.
Listed by: Angela Morra ,Web Max Realty Inc. (416) 790-4136
House for sale: 92 HEADWATER ROAD, Caledon

45 photos

$1,299,000

92 Headwater Road, Caledon (Bolton West), Ontario L7E 2Z3

4 beds
4 baths
30 days

King/Coleraine Welcome to this stunning, fully renovated two-storey family home in the heart of Bolton, where modern luxury meets exceptional functionality. Completely transformed from top to bottom, this impressive four-bedroom residence showcases quality craftsmanship and premium finishes

Listed by: Anna Maria Bellissimo ,Re/max Premier Inc. (416) 987-8000
House for sale: 13 DOCTOR REYNAR ROAD, Caledon

50 photos

$2,599,999

13 Doctor Reynar Road, Caledon (Palgrave), Ontario L7E 4H3

4 beds
5 baths
11 days

Highway 50/Highway 9 A masterfully designed turnkey estate in prestigious Palgrave, this exceptional residence embodies timeless elegance and uncompromising luxury while offering the perfect balance of peaceful estate living just a short drive from the city. Showcasing thousands invested in

Listed by: Connie Bove ,Your Home Sold Guaranteed Realty Specialists Inc (416) 908-5408
House for sale: 80 SILVERVALLEY DRIVE, Caledon

49 photos

$1,689,000

80 Silvervalley Drive, Caledon (Bolton North), Ontario L7E 2Z1

4 beds
4 baths
9 days

Cross Streets: King St E and Evans Ridge. ** Directions: Evans Ridge is between Hwy 50 and Albion Vaughan Road. 80 Silvervalley Drive is a beautifully updated 2666 sqft 2-storey home offering 4 bedrooms, 4 bathrooms on a premium 46.93' x 142.75' lot. With a finished walkout basement, double

House for sale: 249 LEAVENS COURT, Caledon

50 photos

$899,000

249 Leavens Court, Caledon (Bolton East), Ontario L7E 2A8

3 beds
3 baths
5 days

Cross Streets: Hwy 50/Ellwood Dr E. ** Directions: Hwy 50 to Ellewood to Leavens. Located in the desirable South Hill community of Bolton, welcome to 249 Leavens Court. This beautifully updated home features 3 bedrooms, 3 bathrooms, and a finished basement complete with a Cozy rec with rough

Listed by: Rob Schneider ,Century 21 B.j. Roth Realty Ltd. (705) 436-2121
House for sale: 15252 CHINGUACOUSY ROAD, Caledon

48 photos

$1,599,900

15252 Chinguacousy Road, Caledon (Rural Caledon), Ontario L7C 1Z7

4 beds
4 baths
65 days

Cross Streets: North Of Boston Mills. ** Directions: E. Welcome To 15252 Chinguacousy Rd, Caledon-An Exceptional Estate Home Extensively Rebuilt In 2008, Including The Finished Basement, Heated Saltwater Pool, And Stunning Professional Landscaping. Situated On A Private, Beautifully Treed 1.01-Acre

House for sale: 15634 MOUNTAINVIEW Road, Caledon

49 photos

$3,499,999

15634 Mountainview Road, Caledon, Ontario L7C 2V2

5 beds
5 baths
77 days

Mountainview Rd./ Old Base Line Welcome to this one-of-a-kind raised bungalow estate, situated on a breathtaking 4.5-acre manicured lot & offering approx.7,000 sqft of luxurious living space. Designed for both grand entertaining & comfortable family living, this exceptional home showcases high-end

Listed by: Maria Vargas ,Royal Lepage Signature Realty (416) 729-2100

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.