Caledon Homes With Pools

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House for sale: 18577 ST ANDREW'S ROAD, Caledon

37 photos

$1,599,999

18577 St Andrew's Road, Caledon (Caledon East), Ontario L7K 2E3

4 beds
3 baths
160 days

Cross Streets: Charleston Sdrd/St Andrew\"s Rd. ** Directions: Charleston Side Road/St Andrew's Rd E. A Great Opportunity to Own this Stunning Family Home with a Beautiful Serene View, sitting on Just Over One Acre of Land. This Two Storey Home have Four Full Size Bedrooms. Spacious Family

Anna George,Kingsway Real Estate
Listed by: Anna George ,Kingsway Real Estate (905) 510-1509
House for sale: 14453 CENTREVILLE CREEK ROAD, Caledon

50 photos

$3,537,000

14453 Centreville Creek Road, Caledon (Rural Caledon), Ontario L7C 3C1

5 beds
4 baths
58 days

Cross Streets: King/Centreville Creek. ** Directions: King Rd - North of Centreville Creek Rd. An incredible offering mins to Caledon East, Bolton or Brampton! On a paved country road on a 2-acre rural setting, surrounded by mature trees, this entertainer's paradise has the ultimate work-from-home

Kaitlan Klein,Century 21 Millennium Inc.
Listed by: Kaitlan Klein ,Century 21 Millennium Inc. (905) 586-5258
House for sale: 81 PINEBROOK CIRCLE, Caledon

48 photos

$1,449,900

81 Pinebrook Circle, Caledon (Rural Caledon), Ontario L7C 1C3

5 beds
4 baths
42 days

Hwy 10 & Valleywood Blvd Welcome to this stunning two-story 4 bedroom home in the highly desirable Valleywood community. A perfect blend of modern upgrades, elegant finishes and ultimate indoor-outdoor living. Bright and open layout with 9 foot ceilings, crown moulding and luxury vinyl flooring

Listed by: Lori Farquhar ,Royal Lepage Credit Valley Real Estate (416) 230-0550
House for sale: 14237 MOUNT PLEASANT ROAD, Caledon

49 photos

$1,599,900

14237 Mount Pleasant Road, Caledon (Rural Caledon), Ontario L7E 3M9

5 beds
5 baths
16 days

Cross Streets: Mt. Pleasant/Caledon King Line. ** Directions: Caledon King Town Line to Mt. Pleasant. Welcome to 14237 Mount Pleasant! Where you can enjoy Scenic Country Lining within minutes to all amenities of Urban living, with close access to major routes and highways. This raised detached

House for sale: 14294 WINSTON CHURCHILL BOULEVARD, Caledon

50 photos

$2,489,000

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

4 beds
3 baths
49 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: 18754 HEART LAKE ROAD, Caledon

34 photos

$12,950,000

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

5 beds
6 baths
22 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: 7 BRANDIFF COURT, Caledon

44 photos

$1,949,900

7 Brandiff Court, Caledon (Caledon East), Ontario L7C 1P6

5 beds
4 baths
38 days

Cross Streets: Airport/Cranston/Jean/Brandiff. ** Directions: Airport Rd & Old Baseline Rd. A great opportunity to own a beautiful estate home **very rarely offered in this prestigious and extremely scenic Caledon East neighbourhood** Having over 3700 sq ft of custom finished, well maintained,

House for sale: 25 MCCANDLESS COURT, Caledon

50 photos

$1,599,900

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

4 beds
4 baths
98 days

Cross Streets: Old Church Rd/ Innis Lake Rd. ** Directions: Atchison Dr & McCandless Ct. Discover Luxury Living In This Stunning 4-Bedroom, 4-Bathroom Home, Thoughtfully Designed For Both Functionality And Elegance. Main Floor Boasts 9-Foot Ceilings, Hardwood Floors And An Open Concept Layout.

Mary Barone,Royalty Plus Realty Corp.
Listed by: Mary Barone ,Royalty Plus Realty Corp. (416) 414-1658
House for sale: 14165 MCLAUGHLIN ROAD N, Caledon

49 photos

$1,755,000

14165 Mclaughlin Road N, Caledon (Rural Caledon), Ontario L7C 2B3

6 beds
5 baths
3 days

Mclaughlin Rd/King St Welcome To Fully Updated, All-Brick BUNGALOW Nestled On An Acre Of Beautifully Landscaped Land Backing Onto Scenic Farmland. This Bright & Expansive Home Features Approximately 4,500 SqFt Of Well-Designed Living Space, Perfect For Large Families The Main Level: An Elegant

Listed by: Charanjit Angroya ,Re/max Gold Realty Inc. (905) 673-8500
House for sale: 40 HILLTOP DRIVE, Caledon

50 photos

$1,550,000

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

4 beds
3 baths
3 days

Airport Rd & Hilltop Dr Welcome to 40 Hilltop Drive in the heart of Caledon East a stunning 4-bedroom, 3-bathroom home on nearly half an acre, backing onto serene green space and trails. The main floor has been beautifully renovated with new hardwood, updated stairs, crown moulding, pot lights,

House for sale: 88 WALKER ROAD W, Caledon

46 photos

$1,275,000

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 Rd, go West on Walker Rd. 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 of being steps away from everything the

Eran Williamson,Royal Lepage Rcr Realty
Listed by: Eran Williamson ,Royal Lepage Rcr Realty (416) 824-7685
House for sale: 563 RIVER ROAD, Caledon

43 photos

$1,599,000

563 River Road, Caledon (Rural Caledon), Ontario L7K 0E5

4 beds
4 baths
37 days

Cross Streets: Shaws Creek Rd. & Bush St. ** Directions: SHAWS CREEK & BUSH ST. Privacy, Privacy.....Welcome to River Rd. 2.51 acres in the west end of the Historic Hamlet of Belfountain. This home is a must see for all who enjoy endless daylight through massive updated windows. Towering 40ft

House for sale: 32 CEDAR DRIVE, Caledon

50 photos

$2,299,900

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

4 beds
3 baths
44 days

Forks Of The Credit River Rd & Cedar Drive Welcome To 32 Cedar Drive - This 5 Acre Stunning Estate Home Is Tucked Away In One Of Caledons Most Sought After Locations. Perfect Family Home Or Weekend Retreat. Fully Renovated Inside & Out, 4+1 Bedroom Turn-Key Estate Features Magazine Worthy Landscaping

House for sale: 29 CEDAR DRIVE, Caledon

50 photos

$2,590,000

29 Cedar Drive, Caledon (Rural Caledon), Ontario L7K 1H5

3 beds
4 baths
11 days

Hwy 10 & Forks Of The Credit Rd This unique, custom-built home sits on 2.63 acres of offering a perfect mix of tranquility, natural beauty and well landscaped. The property features rolling and level terrain, a peaceful woodlot with wildlife, mature trees, perennial gardens, stone patios, walkways,

Listed by: Sukhjinder Mavi ,Royal Star Realty Inc. (905) 793-1111
House for sale: 18805 WILLOGHBY ROAD, Caledon

41 photos

$1,840,000

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

5 beds
4 baths
52 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

House for sale: 16672 CENTREVILLE CREEK ROAD, Caledon

48 photos

$3,390,000

16672 Centreville Creek Road, Caledon (Rural Caledon), Ontario L7C 3B5

5 beds
3 baths
43 days

OLD CHURCH RD/CENTREVILLE CREEK ROAD A Rare Caledon Estate. Welcome to this beautiful executive bungalow, privately nestled atop 25+ rolling acres in coveted Caledon. The main residence features a bright, open-concept layout with expansive living spaces, a family-style kitchen, and stunning

Listed by: Jolanta Pawlowska ,Homelife/response Realty Inc. (905) 949-0070
House for sale: 19211 MOUNTAINVIEW ROAD, Caledon

49 photos

$1,495,000

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

3 beds
4 baths
29 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! Escape to your own private paradise on this beautiful 1-acre lot, set along a paved country road and

House for sale: 8 VISTA VIEW COURT, Caledon

50 photos

$1,299,000

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

4 beds
4 baths
26 days

Cross Streets: HWY 10 & VALLEYWOOD. ** Directions: From 410 exit N onto Valleywood Rd, R-Royal Valley, R-Garden Wood, R- Vista View. Welcome to this 3+1 Bungalow - over 3,000' of living includes an in-law suite in the coveted Valleywood neighbourhood nestled on a quiet cul-de-sac. Enjoy the

Listed by: Carol Lynn Carter ,Keller Williams Portfolio Realty (416) 579-2803
House for sale: 14812 CENTREVILLE CREEK ROAD, Caledon

48 photos

$2,078,000

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

5 beds
4 baths
14 days

King St & Centreville Creek Rd Discover the ideal harmony of tranquil country living and urban convenience at 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

Dev Patel,Re/max Excellence Real Estate
Listed by: Dev Patel ,Re/max Excellence Real Estate (416) 716-1098
House for sale: 12 KEVINWOOD DRIVE, Caledon

42 photos

$1,389,900

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

5 beds
3 baths
24 days

Hurontario St/Charleston Sdrd Welcome home to this Cozy 3-bedroom family gem . The upper level offers 3 spacious bedrooms, a 4-piece bath with a heated floor. Primary BR with double closets. The main floor flows beautifully with ceramic tile from the entrance through the bright, updated kitchen

Listed by: Robert David Ranieri ,Royal Lepage Certified Realty (905) 601-0587
House for sale: 2097 GRANGE SIDE ROAD, Caledon

39 photos

$9,985,000

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

9 beds
9 baths
3 days

between creditview & mclaren One of Caledon's Most Spectacular Estates with Breathtaking Views of the Caledon Landscape and Toronto Skyline set against panoramic views of the Caledon countryside and Toronto skyline, this estate is the epitome of luxury living and grand entertaining. Featuring

Listed by: Paul Richardson ,Royal Lepage Meadowtowne Realty (905) 877-8262
House for sale: 27 BRIARWOOD DRIVE, Caledon

20 photos

$1,600,000

27 Briarwood Drive, Caledon (Rural Caledon), Ontario L7K 0N1

5 beds
4 baths
64 days

Cross Streets: St Andrews/ Hwy 9 /Beechgroove. ** Directions: St. Andrew Rd & Briarwood Dr. Gorgeous Detached Two-Story Home Situated On 2.52 Acres Of stunningly landscaped Land; This property offers 4 +1 generously sized bedrooms. Each bedroom is bright and features closet organizers. This

House for sale: 15466 THE GORE ROAD, Caledon

40 photos

$18,800,000

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

7 beds
9 baths
82 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: 15252 CHINGUACOUSY ROAD, Caledon

49 photos

$1,799,900

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

4 beds
4 baths
53 days

North Of Boston Mills Welcome To 15252 Chinguacousy Rd, Caledon A Custom-Built Estate Offering 3,700 Sq Ft Of Luxurious Interior Living Space, Perfectly Situated On A Beautifully Treed 1-Acre Lot. This Stunning Home Blends Refined Craftsmanship With Resort-Style Living. Inside, Enjoy Maple

House for sale: 3 RUTLAND HILL COURT, Caledon

42 photos

$3,799,000

3 Rutland Hill Court, Caledon (Rural Caledon), Ontario L7C 0B4

6 beds
6 baths
25 days

Cross Streets: Mountainview & Rutland Hill. ** Directions: Mountainview Rd.- North East on Rutland Hill. Just under an hour from the city, 3 Rutland Hill Crt offers over 15 acres of resort-style living in an exclusive cul-de-sac setting in an immediate area of many multi-million dollar estates,

Hilary Matthews,Harvey Kalles Real Estate Ltd.
Listed by: Hilary Matthews ,Harvey Kalles Real Estate Ltd. (647) 354-9506
House for sale: 9 FLAHERTY LANE, Caledon

49 photos

$6,500,000

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

6 beds
10 baths
11 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: 43 WISHING WELL CRESCENT, Caledon

50 photos

$1,849,000

43 Wishing Well Crescent, Caledon (Rural Caledon), Ontario L7C 3R3

4 beds
6 baths
14 days

Kennedy Road / Dougall Ave Just Listed! 43 Wishing Well Cres, Caledon. A true masterpiece of luxury and design on a premium pie-shaped lot! Step into elegance with this custom home reimagined by Parkyn Design. Featuring hardwood floors throughout, the main floor boasts a stunning layout-living

Rajesh Randev,Century 21 Royaltors Realty Inc.
Listed by: Rajesh Randev ,Century 21 Royaltors Realty Inc. (647) 830-2940
House for sale: 14399 KENNEDY ROAD, Caledon

40 photos

$1,675,000

14399 Kennedy Road, Caledon (Rural Caledon), Ontario L7C 2H4

8 beds
4 baths
43 days

Cross Streets: Kennedy Rd N & King St. ** Directions: Google maps. POWER OF SALE.!! Near all custom made houses. This massive bungalow, nestled on a generous 1.03-acre lot, offers 3 spacious bedrooms on main with the 5 more bedroom in the fully finished lower level. Recently renovated inside

Listed by: Inderjeet Singh ,Re/max Gold Realty Inc. (647) 515-2066
House for sale: 62 GARDENIA WAY, Caledon

23 photos

$949,900

62 Gardenia Way, Caledon (Rural Caledon), Ontario L7C 1A8

4 beds
2 baths
17 days

Valley Wood Blvd & Royal Valley Dr Plant your roots on Gardenia! Where functionality meets sophistication: 62 Gardenia Way is thoughtfully renovated top to bottom with the growing family in mind and built-ins at the front, back and all the in between places. Welcomed by the open concept and

Victoria Soucier,Royal Lepage Signature Realty
Listed by: Victoria Soucier ,Royal Lepage Signature Realty (416) 804-0890
House for sale: 26 ARCADIA ROAD, Caledon

49 photos

$1,625,000

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

4 beds
5 baths
87 days

Kennedy & Learmont Nestled in the heart of Southfields Village, one of Caledon's most sought-after communities, this stunning residence sits proudly on the largest lot on the street and offers over 3,300square feet of luxurious living space. With four generously sized bedrooms, each with its

Listed by: June Dias ,Homelife Woodbine Realty Inc. (416) 741-4443
House for sale: 14201 WINSTON CHURCHILL BOULEVARD, Caledon

49 photos

$1,299,999

14201 Winston Churchill Boulevard, Caledon (Rural Caledon), Ontario L7C 1S6

4 beds
3 baths
39 days

Winston Churchill/ King Welcome to 14201 Winston Churchill Blvd, Nestled in the scenic community of Terra Cotta, Caledon! Experience refined country living in this stunning custom home set on a pictures que lot surrounded by mature trees and rolling landscapes. This beautifully maintained property

Listed by: Kv Singh ,Re/max Gold Realty Inc. (647) 404-0000
House for sale: 47 LARRY STREET, Caledon

45 photos

$1,248,000

47 Larry Street, Caledon (Caledon East), Ontario L7C 1K8

3 beds
2 baths
14 days

Airport / Larry This spectacular side-split is located in one of the most sought-after neighbourhood in Caledon East. Prepare to be amazed by the spaciousness and layout of this beautiful family home. It is totally updated throughout with very attractive finishes. Main level features an updated

Jerry Vancooten,Royal Lepage Credit Valley Real Estate
Listed by: Jerry Vancooten ,Royal Lepage Credit Valley Real Estate (416) 456-0462
House for sale: 17088 HORSESHOE HILL ROAD, Caledon

45 photos

$2,499,900

17088 Horseshoe Hill Road, Caledon (Rural Caledon), Ontario L7C 2N6

5 beds
5 baths
10 days

Horseshoe Hill Rd/ The Grange Sdrd Welcome to 17088 Horseshoe Hill Rd! This stunning functional turn-key bungaloft in the heart of Caledon, with over 500K in upgrades, offers breathtaking escarpment views! This exceptional property sits on 2.6 picturesque acres and features a sparkling inground

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
22 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: 4 BRETHBY STREET, Caledon

46 photos

$1,395,000

4 Brethby Street, Caledon (Rural Caledon), Ontario L7C 3W2

5 beds
5 baths
52 days

Cross Streets: Kennedy & Learmont. ** Directions: Kennedy St N to Learmont to Brethby. Amazing and rare large pool-sized lot is a prime bonus of this beautiful detached home! Some features include 2 primary bedrooms with full ensuite baths, full finished basement with 5th bedroom and 5th bathroom.

Listed by: Michelle Lavictoire ,Sutton Group Quantum Realty Inc. (416) 823-5142
House for sale: 23 LARSON PEAK ROAD, Caledon

50 photos

$1,599,900

23 Larson Peak Road, Caledon (Rural Caledon), Ontario L7C 3P7

6 beds
5 baths
32 days

Larson Peak Rd and Kennedy Road Welcome to 23 Larson Rd a true showstopper combining luxury, comfort, and nature. This stunning 3,070 sq. ft. home (per MPAC) sits on a premium ravine lot backing onto a tranquil pond, offering breathtaking views and privacy.Featuring a professionally finished

House for sale: 13443 WINSTON CHURCHILL BOULEVARD, Caledon

43 photos

$4,200,000

13443 Winston Churchill Boulevard, Caledon (Rural Caledon), Ontario L7C 1S4

3 beds
2 baths
3 days

Winston Churchill & Old School Investment! Family Home! Bungalow on 50 Flat acres just north of the proposed Hwy 413. Currently farmed with great possibilities. The 3 bedroom home has a huge, sunfilled kitchen with morning sunrises and a large primary suite with walk-out. Large family room

Listed by: Paul Richardson ,Royal Lepage Meadowtowne Realty (905) 877-8262
House for sale: 18555 HURONTARIO STREET E, Caledon

40 photos

$1,599,000

18555 Hurontario Street E, Caledon (Caledon Village), Ontario L7K 0X8

5 beds
3 baths
31 days

Hurontario St--Charleston Sdrd This beautifully renovated detached home in Caledon Village offers the perfect blend of comfort, space, and privacy on a large 0.81-acre lot along Hurontario Street. Featuring 4 spacious bedrooms and 3 bathrooms, the home has been upgraded with new pot lights,

Kamal Sandhu,Re/max Gold Realty Inc.
Listed by: Kamal Sandhu ,Re/max Gold Realty Inc. (647) 891-0143
House for sale: 8 ELITE ROAD, Caledon

37 photos

$1,499,000

8 Elite Road, Caledon (Rural Caledon), Ontario L7K 0K9

5 beds
3 baths
31 days

Charleston & Horseshoe Hill Rd Set on 4.08 acres in a sought-after estate community, this family home blends elegance, comfort, and modern upgrades. With 4 bedrooms, main floor laundry, and a cozy family room anchored by a gas fireplace, the layout is designed for everyday living. The custom

Listed by: Nick Oppedisano ,Re/max Premier The Op Team (416) 270-1431
House for sale: 13867 HERITAGE ROAD, Caledon

32 photos

$2,795,000

13867 Heritage Road, Caledon (Rural Caledon), Ontario L7C 3E9

5 beds
4 baths
3 days

King & Heritage Brand New Custom Luxury Home in Sought-After Southwest Caledon! Be the first to live in this exceptional, privately built estate on a stunning ravine lot near Terra Cotta. Offering over 4,000sq ft of premium living space, this home combines luxury, functionality, and privacy

Listed by: Paul Richardson ,Royal Lepage Meadowtowne Realty (905) 877-8262
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
73 days

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 COTTONFIELD CIRCLE, Caledon

49 photos

$1,699,900

32 Cottonfield Circle, Caledon (Rural Caledon), Ontario L7C 3M9

5 beds
5 baths
9 days

Kennedy Rd And Mayfield Welcome to this meticulously maintained detached home with a double-car garage, nestled on a quiet and highly sought-after circle. This residence showcases a blend of luxury and functionality, beginning with an impressive custom double-door entry that leads into a bright

Ron Chatha,Upstate Realty Inc.
Listed by: Ron Chatha ,Upstate Realty Inc. (416) 723-9500
House for sale: 50 ROYAL FERN CRESCENT, Caledon

46 photos

$1,249,999

50 Royal Fern Crescent, Caledon (Rural Caledon), Ontario L7C 4H1

4 beds
4 baths
14 days

Kennedy Rd & Mayfield Rd Welcome to this beautifully designed, 2-year-old, sun-filled home situated on a premium pie-shaped lot offering plenty of space for a future pool or backyard oasis. With great curb appeal, and a double-door entry, this home exudes elegance and functionality from the

Sud Sharma,Re/max Real Estate Centre Inc.
Listed by: Sud Sharma ,Re/max Real Estate Centre Inc. (416) 356-9119
House for sale: 43 FLEMINGTON DRIVE, Caledon

42 photos

$999,999

43 Flemington Drive, Caledon (Rural Caledon), Ontario L7C 1B7

4 beds
2 baths
81 days

Highway 10/Valleywood Bright & Beautiful Raised Bungalow in Caledon's Desirable Valleywood Neighborhood! Perfect for 1st-Time Buyers, Downsizers or Investors. Located on Quiet, Family-Friendly Street W/In Law Suite or Income Potential on Pool-Sized Lot. Main Level Features Open-Concept Din/Liv

Craig Tozer,Re/max West Realty Inc.
Listed by: Craig Tozer ,Re/max West Realty Inc. (416) 745-2300
House for sale: 12 GLENN COURT, Caledon

50 photos

$1,799,000

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

7 beds
3 baths
24 days

Cross Streets: Airport Rd / Coolihans Side Rd. ** Directions: North on Airport Rd, Turn right on Coolihans Side Rd, Left on Glenn Court. This beautifully updated home boasts over 100 updates in the past five years, making it truly one of a kind. Major improvements include relocating the laundry

Walter Wallace,Re/max Hallmark Realty Ltd.
Listed by: Walter Wallace ,Re/max Hallmark Realty Ltd. (416) 566-9276
House for sale: 62 PAISLEY GREEN AVENUE, Caledon

42 photos

$1,349,000

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

4 beds
5 baths
2 days

Old Church/Atchison Dr Welcome to this beautiful family home in the highly sought-after Pathways community of Caledon East! This spacious 4-bedroom property blends elegance, comfort, and everyday functionality-perfect for growing families or anyone seeking a vibrant, welcoming neighbourhood.The

Cheryl Robb,Royal Lepage Rcr Realty
Listed by: Cheryl Robb ,Royal Lepage Rcr Realty (416) 805-1316
House for sale: 32 CALEDON STREET, Caledon

33 photos

$1,200,000

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

5 beds
3 baths
19 days

Cross Streets: MAIN ST?QUEEN ST W. ** Directions: MAIN ST/QUEEN ST W. Beautiful 3+2 Bedroom Bungalow with a WALK OUT BASMENT!! 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

Listed by: Manveer Singh Dhindsa ,Re/max Realty Services Inc. (905) 456-1000
House for sale: 28 LARRY Street, Caledon

24 photos

$1,295,000

28 Larry Street, Caledon, Ontario L7C 1K8

4 beds
3 baths
14 days

Airport Road / Larry Street Welcome to a home where comfort, style, and family living meet in the heart of Caledon East. This beautiful property is surrounded by scenic walking trails, sought after schools, friendly shops, and a brand-new recreation centre everything your family needs just

Matt Petrovich,Keller Williams Experience Realty Brokerage
Listed by: Matt Petrovich ,Keller Williams Experience Realty Brokerage (705) 331-2461
House for sale: 110 PALMER CIRCLE, Caledon

50 photos

$1,699,990

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

4 beds
4 baths
50 days

North of Old Church B/W Hwy 50 & Mt Hope Welcome to 110 Palmer Circle, a beautifully cared-for family home nestled on a quiet, desirable street in one of Caledon's most sought-after communities. From the moment you arrive, you'll notice the pride of ownership with its charming curb appeal,

House for sale: 160 LITTLE COURT, Caledon

47 photos

$1,799,900

160 Little Court, Caledon (Bolton North), Ontario L7E 3T8

4 beds
3 baths
53 days

Humber Lea Rd/Crestwood Rd/Little Court Welcome to 160 Little Court, a rare offering on Boltons most exclusive 7-home private court. This exceptional 4-bedroom family residence sits on nearly half an acre with no neighbours behind, backing onto protected conservation. The true showstopper is

Katharine Loucaidou,Exp Realty
Listed by: Katharine Loucaidou ,Exp Realty (905) 863-7893

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.