Caledon Homes With Pools

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House for sale: 446 THE GRANGE SIDE ROAD, Caledon

50 photos

$5,850,000

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

4 beds
5 baths
14 days

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: 20909 SHAWS CREEK ROAD, Caledon

40 photos

$1,125,000

20909 Shaws Creek Road, Caledon (Alton), Ontario L7K 1L7

4 beds
2 baths
13 days

Cross Streets: Highpoint & Shaws Creek. ** Directions: North of Highpoint. A Storybook Country Escape in the Heart of Caledon! Tucked among mature trees and rolling hills, this one-of-a-kind country retreat offers the perfect blend of character, privacy, and outdoor living. Set on just over

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
249 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: 62 GIBSON LAKE DRIVE, Caledon

50 photos

$2,099,000

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

4 beds
5 baths
8 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: 14812 CENTREVILLE CREEK ROAD, Caledon

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$1,649,000

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

5 beds
4 baths
56 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: 12 WATERBURY STREET, Caledon

48 photos

$965,000

12 Waterbury Street, Caledon (Bolton East), Ontario L7E 1X2

3 beds
3 baths
17 days

Landsbridge & Royalton Stunning family residence nestled on Bolton's desirable South Hill, thoughtfully updated inside and out for comfortable everyday living and exceptional entertaining. The beautifully renovated kitchen showcases rich maple cabinetry, a spacious pantry, porcelain tile flooring,

Listed by: Sonan Askndar ,Re/max Noblecorp Real Estate (905) 856-6611
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
279 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: 17397 HUMBER STATION ROAD, Caledon

49 photos

$2,389,900

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

4 beds
4 baths
250 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: 15277 DIXIE ROAD, Caledon

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$1,749,000

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

5 beds
4 baths
83 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: 33 GIBSON LAKE DRIVE, Caledon

29 photos

$2,149,000

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

3 beds
4 baths
24 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: 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
38 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: 19211 MOUNTAINVIEW ROAD, Caledon

41 photos

$1,400,000

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

4 beds
5 baths
21 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: 31 FIELDSTONE LANE AVENUE, Caledon

46 photos

$1,499,000

31 Fieldstone Lane Avenue, Caledon (Rural Caledon), Ontario L7C 1C4

5 beds
6 baths
45 days

Mayfield & Kennedy Premium Ravine lot, one-of-a-kind fully upgraded detached property, offering a perfect blend of elegance and modern luxury. **2nd floor has 4 bedrooms and 4 washrooms**. The professionally finished basement, completed by the builder, includes a separate entrance and offers

Listed by: Aman Swaich ,Re/max Gold Realty Inc. (905) 456-1010
House for sale: 13450 HERITAGE ROAD, Caledon

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$1,434,905

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

4 beds
3 baths
46 days

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: 5 VALLEYGREEN CRESCENT S, Caledon

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$1,675,000

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

5 beds
4 baths
32 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 offers a rare combination of luxury, space, and complete move-in readiness. Designed

House for sale: 16927 WINSTON CHURCHILL BOULEVARD, Caledon

50 photos

$4,500,000

16927 Winston Churchill Boulevard, Caledon (Rural Caledon), Ontario L7K 1H9

5 beds
3 baths
29 days

Grange/Winston Churchill A Victorian reimagined, complete with a secret English garden. Just outside Belfountain, on nearly 15 acres of Caledon countryside, it is steeped in character and completely its own. The main house holds four bedrooms and three bathrooms, anchored by a bright central

Jade Skuce,Royal Lepage Rcr Realty
Listed by: Jade Skuce ,Royal Lepage Rcr Realty (519) 941-5151
House for sale: 5 MASSARI STREET, Caledon

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$1,725,000

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

4 beds
3 baths
14 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: 110 PALMER CIRCLE, Caledon

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$1,600,000

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

4 beds
4 baths
27 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: 4 WOLF CRESCENT, Caledon

32 photos

$1,999,900

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

4 beds
3 baths
9 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: 50 ESPOSITO DRIVE, Caledon

50 photos

$1,289,800

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

4 beds
4 baths
20 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 Rarely offered on one of Bolton's

Listed by: Dino Nunno (416) 690-2121
House for sale: 16718 CALEDON KING TOWNLINE N, Caledon

48 photos

$2,998,000

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

5 beds
2 baths
14 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: 20511 MAIN STREET, Caledon

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$1,990,000

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

6 beds
5 baths
8 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: 26 ARCADIA ROAD, Caledon

46 photos

$1,449,000

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

4 beds
5 baths
13 days

Kennedy & Learmont KEY HIGHLIGHTS Resort-Style Backyard Oasis Heated inground pool Gas BBQ and entertaining area Professional landscaping and lighting Private fenced yard with storage shed for relaxing and entertaining Kitchen Built for Cooking & Gathering Spacious kitchen with abundant cabinetry

Listed by: June Dias ,Royal Lepage Certified Realty (416) 741-4443
House for sale: 258 AMOS DRIVE, Caledon

50 photos

$3,588,000

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

4 beds
5 baths
11 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: 23 DEER VALLEY DRIVE, Caledon

48 photos

$1,299,000

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

4 beds
4 baths
5 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

33 photos

$959,999

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

5 beds
3 baths
5 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: 4 WOODLOT COURT, Caledon

45 photos

$2,829,000

4 Woodlot Court, Caledon (Palgrave), Ontario L7E 0C2

8 beds
7 baths
5 days

Mount Wolfe and Highcrest Your search ends in this very cul de sac! Welcome to 4 Woodlot Court...Multigenerational living at it's finest! This majestic property is nothing short of breathtaking! Situated on a 2 acre lot nestled among gorgeous custom built estate homes! Take in the extensively

Listed by: Frank Riga ,Re/max Experts (905) 499-8800
House for sale: 57 KENNEDY Road, Caledon

49 photos

$2,500,000

57 Kennedy Road, Caledon, Ontario L7C 2M7

4 beds
7 baths
2 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
1 day

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: 6 OVERLOOK RIDGE, Caledon

49 photos

$1,849,000

6 Overlook Ridge, Caledon (Palgrave), Ontario L7E 0C1

5 beds
3 baths
56 days

Mt Pleasant & Old Church Elevate Your Lifestyle with this Stunning Custom Built Bungalow with Finished Walk-Out Basement in Rolling Meadows Estates, Situated on a Picturesque Estate Lot. Magnificent Backyard Oasis, Heated Pool, Cabana, and Hot Tub, Landscaped with Flag Stone, Interlock and

Listed by: Silvestro Papa ,Re/max Experts (905) 499-8800
House for sale: 19772 AIRPORT ROAD, Caledon

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$948,000

19772 Airport Road, Caledon (Rural Caledon), Ontario L7K 0A3

4 beds
3 baths
8 days

Airport Road and Hwy 9 !! DECEPTIVELY SPACIOUS MASTERPIECE !! Family-friendly living meets luxury in this detached home, masterfully rebuilt "to-the-studs" (2025). Perfect for parents, the school bus stops right at your front door, with top-tier schools just minutes away! Quick closing available!

Listed by: Amparo Norm Cardenas Cascante ,Royal Lepage Real Estate Services Ltd. (416) 804-8093
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
92 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: 16735 MISSISSAUGA ROAD, Caledon

44 photos

$1,999,000

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

3 beds
2 baths
52 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: 9 FLAHERTY LANE, Caledon

49 photos

$6,399,000

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

6 beds
10 baths
60 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: 17 AGNES STREET, Caledon

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$1,149,900

17 Agnes Street, Caledon (Alton), Ontario L7K 0C6

4 beds
3 baths
27 days

Cross Streets: King/Agnes St. ** Directions: Charleston To Main St N to King St, left to top of hill on left. What a gorgeous home in the desirable Village of Alton. The Stunning curb appeal is just the beginning of this wonderful package. The spacious open concept ranch bungalow with bright

Listed by: Arlene C Peavoy ,Icloud Realty Ltd. (519) 942-5044
House for sale: 3 BOWES Court, Caledon

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$1,249,000

3 Bowes Court, Caledon, Ontario L7E 1A5

6 beds
4 baths
9 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: 3 BOWES COURT, Caledon

50 photos

$1,249,000

3 Bowes Court, Caledon (Bolton West), Ontario L7E 1A5

6 beds
4 baths
31 days

Cross Streets: Bowes/DeRose. ** Directions: 150-Chickadee-Bowes. Spacious and well-appointed large 2-storey home offering exceptional move-in versatility for large families and multi-generational living. From the moment you walk up to the front door and imagine sitting outside on rainy days

Listed by: Andy Tulloch ,Century 21 Heritage House Ltd (519) 570-4663
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
20 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: 2097 GRANGE SIDE ROAD, Caledon

39 photos

$8,933,000

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

9 beds
9 baths
55 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: 15163 CENTREVILLE CREEK ROAD, Caledon

48 photos

$1,999,999

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

4 beds
5 baths
26 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: 8 VISTA VIEW COURT, Caledon

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$1,299,000

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

4 beds
4 baths
40 days

Cross Streets: HWY 10 & Valleywood. ** Directions: 410, exit N - Valleywood Rd, R-Royal Valley, r-Garden Wood, R-Vista view. Freshly painted and tucked away on a quiet Valleywood cul-de-sac, this beautifully maintained ravine-side bungalow offers over 3,300 sq ft of finished living space with

Listed by: Carol Lynn Carter ,Keller Williams Portfolio Realty (416) 579-2803
House for sale: 15634 MOUNTAINVIEW Road, Caledon

49 photos

$3,499,999

15634 Mountainview Road, Caledon, Ontario L7C 2V2

5 beds
5 baths
31 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
House for sale: 15634 MOUNTAINVIEW ROAD, Caledon

49 photos

$3,499,999

15634 Mountainview Road, Caledon (Caledon East), Ontario L7C 2V2

5 beds
5 baths
20 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

House for sale: 100 WALKER ROAD W, Caledon

50 photos

$1,039,000

100 Walker Road W, Caledon (Caledon East), Ontario L7C 3M4

4 beds
4 baths
7 days

Walker Rd W & Airport Rd Welcome to this stunning semi-detached home located in the highly desirable community of West Caledon. Offering 1,940 square feet of pristine main living space and a total of 2,500 square feet of finished area, this property perfectly blends modern elegance with ultimate

Listed by: Nikolche Ilkanovski ,Royal Lepage Real Estate Services Ltd. (647) 289-6356
House for sale: 38 MARILYN STREET, Caledon

50 photos

$1,699,900

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

4 beds
4 baths
33 days

Old Church and Marilyn St. Stunning 3+1 Bed 4 Bath Home On 1.13 Acres In The Village Caledon East. 4443Sgft Of Living Space, 100Ft Wide Lot W/ Mature Trees & Privacy. A 22X32Ft Addition W/ Wrap Around Windows(2016), 16X24Ft Pool W/ Composite Deck "Entertainers Delight W/ Outdoor Tv" (2017),

Listed by: Ross Vignale ,Re/max Realty Services Inc. (905) 702-4326
House for sale: 18 WALTON DRIVE, Caledon

45 photos

$2,329,511

18 Walton Drive, Caledon (Palgrave), Ontario L7E 0A1

6 beds
6 baths
9 days

Highway 50/ Old Church PRICED TO SELL @ GREAT OPPORTUNITY TO OWN THIS BEAUTIFUL MASTERPIECE HOUSE, Nestled in the highly sought-after Cedar Mills community, this exceptional executive residence offers luxury living at its finest and functionality with the added convenience of a main-floor primary

House for sale: 45 SUNKIST VALLEY ROAD, Caledon

50 photos

$1,099,000

45 Sunkist Valley Road, Caledon (Bolton East), Ontario L7E 1T1

5 beds
3 baths
29 days

King st E/Albion-Vaughan Welcome to 45 Sunkist Valley Road, a truly special family home nestled in one of Bolton's most sought-after yet quietly tucked-away neighbourhoods. Offering 4+1 bedrooms and a thoughtfully designed layout, this home provides the perfect balance of comfort, functionality,

Stuart Sinclair,Re/max Experts
Listed by: Stuart Sinclair ,Re/max Experts (905) 499-8800
House for sale: 14603 AIRPORT ROAD, Caledon

2 photos

$3,499,999

14603 Airport Road, Caledon (Rural Caledon), Ontario L7C 2X8

5 beds
3 baths
27 days

Airport Rd Btw King & Old Base Welcome to this beautifully maintained, custom-built 5-bedroom side-split home, set on a private 0.95-acre lot in a peaceful countryside setting. From the moment you arrive, the property makes a lasting impression with its custom stone fencing, grand entry gates,

Listed by: Yuvraj Singh ,Lpt Realty (705) 650-0095
House for sale: 12 KEVINWOOD DRIVE, Caledon

45 photos

$1,389,900

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

5 beds
3 baths
9 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: 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
21 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

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.