Caledon Homes With Pools

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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
99 days

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 rolling hills. This exceptional property showcases meticulous landscaping, breathtaking

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

30 photos

$1,685,000

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

4 beds
3 baths
106 days

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 and 3 bathrooms designed for both

House for sale: 16735 MISSISSAUGA ROAD, Caledon

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$1,599,000

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

3 beds
2 baths
144 days

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 services just a 15 minute walk from this 10 acre gem. The house is move in ready & overlooks

House for sale: 15668 SHAWS CREEK ROAD, Caledon

48 photos

$3,200,000

15668 Shaws Creek Road, Caledon (Rural Caledon), Ontario L7C 1V6

4 beds
3 baths
20 days

Set on 43+ acres with mature trees, open lawns, perennial and vegetable gardens, flagstone patios, and a large stream-fed pond, this exceptional country estate offers timeless character in a highly desirable setting. The circa-1900 stone residence, with a Napier Simpson addition, offers approximately

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
77 days

Welcome to 9 Flaherty Lane, a breathtaking custom estate nestled on over 10.6 acres in one of Caledon's prestigious enclaves and backing onto 50 acres of conservation land. Spanning over 13,500 square feet above grade and over 20,000 square feet total, this residence offers homeowners unmatched

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
66 days

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 included) and upgraded

House for sale: 2814 FORKS OF THE CREDIT ROAD, Caledon

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$2,468,000

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

5 beds
6 baths
18 days

Welcome to a one-of-a-kind longevity estate where nature, privacy & wellness-focused design converge on 2.71 picturesque acres. Ideally located near the Pulpit Club, Caledon Mountain Trout Club, Caledon Ski Club, Brampton Flying Club & Bruce Trail, this extraordinary property offers a private

Sam Allan Mcdadi,Sam Mcdadi Real Estate Inc.
Listed by: Sam Allan Mcdadi ,Sam Mcdadi Real Estate Inc. (905) 502-1500
House for sale: 19 MCCONACHIE CRESCENT, Caledon

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$1,500,000

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

4 beds
3 baths
7 days

Beautifully maintained raised bungalow set on a private 1.5-acre country lot, offering the perfect blend of tranquility and convenience. This spacious home features 3+1 bedrooms, 3 full bathrooms, and a functional layout ideal for families, multi-generational living, or those seeking extra

Listed by: Shawn Chhabra ,Real Estate Advisors Inc. (416) 691-3000
House for sale: 14812 CENTREVILLE CREEK ROAD, Caledon

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$1,599,000

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

5 beds
4 baths
30 days

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 surroundings just minutes from

Dev Patel,Re/max Excellence Real Estate
Listed by: Dev Patel ,Re/max Excellence Real Estate (416) 716-1098
House for sale: 18 FILTON ROAD, Caledon

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$1,799,900

18 Filton Road, Caledon (Caledon East), Ontario L7C 1R5

4 beds
4 baths
16 days

Welcome to 18 Filton Road, a custom-built executive home in the heart of Caledon East. This 4-bedroom residence showcases 7.5-inch engineered white oak hardwood floors, upgraded trim, and designer colours throughout. A dramatic 17'10" open-to-above ceiling soars over the foyer and living room,

Listed by: Ross Vignale ,Re/max Realty Services Inc. (905) 702-4326
House for sale: 28 BILLY COURT, Caledon

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$1,629,000

28 Billy Court, Caledon (Caledon East), Ontario L7C 3X3

4 beds
5 baths
12 days

Welcome to 28 Billy Court, an exceptional luxury residence in Caledon East, where refined elegance meets resort-style living. Set on a 202-ft-deep lot in a family-friendly neighbourhood, this impressive home showcases high-end finishes, an impressive layout and a spectacular backyard retreat.

Bill Parnaby,Royal Lepage Rcr Realty
Listed by: Bill Parnaby ,Royal Lepage Rcr Realty (289) 514-2489
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
100 days

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 the bright, updated kitchen and hardwood floors in the cozy

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
55 days

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. Located in close proximity to

House for sale: 4845 ESCARPMENT SIDE ROAD, Caledon

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$2,498,000

4845 Escarpment Side Road, Caledon (Rural Caledon), Ontario L7C 0A7

5 beds
3 baths
20 days

Private 24.9 acres across from the Paintbrush Golf Course, positioned high on Caledon's Escarpment, this custom, architect-designed 4+1 bed, 2.5 bath has beautiful curb appeal on a park-like, idyllic setting and features country views from every window, sun all day in the south-facing backyard

Kaitlan Klein,Century 21 Millennium Inc.
Listed by: Kaitlan Klein ,Century 21 Millennium Inc. (905) 586-5258
House for sale: 1666 SPRUCE DRIVE, Caledon

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$1,298,000

1666 Spruce Drive, Caledon (Caledon Village), Ontario L7K 1B2

5 beds
3 baths
7 days

An entertainer's paradise in the Village of Caledon, this 5-bed, 2.5-bath offers a vast yard to play in and has a private circular drive with ample parking. Private, mature corner lot w/ towering trees, gorgeous perennial gardens, raised vegetable garden beds, multiple decks, patios and sitting

Kaitlan Klein,Century 21 Millennium Inc.
Listed by: Kaitlan Klein ,Century 21 Millennium Inc. (905) 586-5258
House for sale: 15 CALEDON MOUNTAIN DRIVE, Caledon

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$2,795,000

15 Caledon Mountain Drive, Caledon (Rural Caledon), Ontario L7K 0G1

4 beds
3 baths
20 days

No need for AI embellishment here! This one-of-a-kind, 3.3 acre country retreat located just outside the quaint hamlet of Belfountain is pretty perfect all on its own. Professionally designed and renovated from top to bottom in 2020, this beautifully reimagined home offers a mix of modern design

House for sale: 19211 MOUNTAINVIEW ROAD, Caledon

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$1,349,900

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

4 beds
5 baths
85 days

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 spacious 2-storey home offers comfort, character, and a truly unique resort-style lifestyle.With over 3000 sq. ft. of living

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
104 days

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, farmhouse sink, pot fillers, stainless steel appliances, and abundant cabinetry. Enjoy oversized principal

House for sale: 53 MARILYN STREET, Caledon

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$1,099,900

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

4 beds
3 baths
91 days

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 blend of privacy, space,

Nik Handa,Real Broker Ontario Ltd.
Listed by: Nik Handa ,Real Broker Ontario Ltd. (647) 404-4083
House for sale: 7 MAPLE MEADOW COURT, Caledon

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$5,250,000

7 Maple Meadow Court, Caledon (Rural Caledon), Ontario L7K 0G2

5 beds
7 baths
26 days

A rare offering in Caledon Mountain Estates on 2.8 acres, this newly built contemporary estate pairs exceptional scale and sophisticated design with a level of privacy that is increasingly difficult to find-all within convenient reach of the GTA. Set against a peaceful natural landscape, the

Shawna Mcfadyen,Housesigma Inc.
Listed by: Shawna Mcfadyen ,Housesigma Inc. (647) 360-2330
House for sale: 44 GEORGE CRESCENT, Caledon

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$1,695,000

44 George Crescent, Caledon (Caledon East), Ontario L7C 1G2

5 beds
4 baths
12 days

Welcome to 44 George Crescent - an exceptional country estate in the prestigious executive community of Caledon East. Set on a spectacular 2-acre property surrounded by mature trees and established landscaping, this beautifully maintained all-brick, two-storey home offers over 5,000 sq. ft.

Listed by: Sigrid Doherty ,Re/max Realty Specialists Inc. (905) 584-2727
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
98 days

The perfect home for summer, this executive residence is ideally located in the heart of Caledon East. Offering four spacious bedrooms and three bathrooms, the home welcomes you with a large foyer and an impressive double staircase, reflecting the care and thoughtful updates it has received

Peter Ramon Droog,Royal Lepage Meadowtowne Realty
Listed by: Peter Ramon Droog ,Royal Lepage Meadowtowne Realty (647) 282-5010
House for sale: 2097 GRANGE SIDE ROAD, Caledon

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$7,600,000

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

9 beds
9 baths
76 days

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 designed to offer the perfect

Listed by: Paul Richardson ,Royal Lepage Meadowtowne Realty (905) 877-8262
House for sale: 25 MCCANDLESS COURT, Caledon

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$1,349,900

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

4 beds
4 baths
56 days

Welcome To 25 McCandless Court, A Stunning 3000+ sq ft plus finished basement 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 Ceilings, Hardwood Floors, And

Stuart Sinclair,Re/max Experts
Listed by: Stuart Sinclair ,Re/max Experts (905) 499-8800
House for sale: 25 HILLTOP DRIVE, Caledon

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$1,179,000

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

4 beds
2 baths
21 days

***PUBLIC OPEN HOUSE - SATURDAY OCTOBER 3rd, 2:00-4:00pm*** 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

Anna Fitzcharles,One Percent Realty Ltd.
Listed by: Anna Fitzcharles ,One Percent Realty Ltd. (416) 858-5657
House for sale: 5 VALLEYGREEN CRESCENT S, Caledon

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$1,489,000

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

5 beds
4 baths
11 days

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 of luxury, space,

House for sale: 16112 THE GORE ROAD, Caledon

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$1,788,000

16112 The Gore Road, Caledon (Rural Caledon), Ontario L7C 3E6

3 beds
3 baths
2 days

Welcome to this exquisite custom-built Raised Bungalow offering approximately 2,545 sq. ft. on the main level, plus an additional 2,465 sq. ft. of finished walkout lower level living space in the heart of rural Caledon. Surrounded by mature trees, backing the Caledon Trailway Path, scenic landscapes,

Bill Parnaby,Royal Lepage Rcr Realty
Listed by: Bill Parnaby ,Royal Lepage Rcr Realty (289) 514-2489
House for sale: 18250 DUFFY'S LANE, Caledon

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$5,499,000

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

4 beds
4 baths
68 days

Extraordinary Palgrave 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, productive hay fields, mature

House for sale: 4780 ESCARPMENT SIDE ROAD, Caledon

44 photos

$10,900,000

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

7 beds
5 baths
71 days

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 Sideroad and St. Andrews Road,

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
106 days

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 Luxury, Privacy, And Endless Potential.

Denise Gottardo,Re/max Millennium Real Estate
Listed by: Denise Gottardo ,Re/max Millennium Real Estate (905) 265-2200
House for sale: 34 BOYCES CREEK COURT, Caledon

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$1,449,999

34 Boyces Creek Court, Caledon (Caledon East), Ontario L7C 3S2

5 beds
4 baths
8 days

Welcome home to this beautifully designed 2-storey residence, offering the perfect blend of comfortable family living and outdoor entertaining. Inside, you'll find 4 generously sized bedrooms and 4 full bathrooms spread across two thoughtfully laid-out levels, ideal for growing families or

House for sale: 19 BIRCH AVENUE, Caledon

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$1,329,900

19 Birch Avenue, Caledon (Palgrave), Ontario L7E 0K1

4 beds
3 baths
21 days

Welcome to this masterfully designed property in the heart of Palgrave, where timeless character meets uncompromising modern luxury. Enjoy absolute maintenance free comfort from the fresh stucco exterior & steel roof to the heated, patterned-concrete driveway, walkways & patios & a lush front

Greg Ringer,Royal Lepage Rcr Realty
Listed by: Greg Ringer ,Royal Lepage Rcr Realty (905) 857-0651
House for sale: 9 MORAINE PLACE, Caledon

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$1,999,000

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

3 beds
4 baths
6 days

Refined country living in one of Palgrave's most sought-after executive enclaves. Privately positioned on nearly 2 acres, this impressive custom bungalow delivers space, privacy, and resort-inspired outdoor living. Beautifully landscaped grounds surround a stunning saltwater in-ground pool,

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
97 days

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 bedrooms and a 4 pc

Listed by: Manveer Singh Dhindsa ,Re/max Realty Services Inc. (905) 456-1000
House for sale: 67 SHERIN COURT, Caledon

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$954,900

67 Sherin Court, Caledon (Bolton North), Ontario L7E 3T6

4 beds
3 baths
35 days

Tucked away on a quiet court in Bolton's highly desirable North Hill community, this beautifully renovated 4 bedrooms home sits on an impressive oversized lot, offering the perfect balance of privacy, style, and functionality. Thoughtfully redesigned with warm wood finishes and rustic-inspired

Chris Kelos,Re/max Hallmark Realty Ltd.
Listed by: Chris Kelos ,Re/max Hallmark Realty Ltd. (416) 465-7850
House for sale: 23 DEER VALLEY DRIVE, Caledon

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$1,259,000

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

4 beds
4 baths
29 days

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 its original owners, this home has been the backdrop for years of family memories and is ready

Janine Speirs,Re/max Real Estate Centre Inc.
Listed by: Janine Speirs ,Re/max Real Estate Centre Inc. (647) 964-3307
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
99 days

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 Open concept Separate Living, Dinning & Family Room. Chefs Dream incredible Custom Gourmet Kitchen w/large

Jagat Patel,Homelife/miracle Realty Ltd
Listed by: Jagat Patel ,Homelife/miracle Realty Ltd (647) 669-0331
House for sale: 6 COUNTRY LANE DRIVE, Caledon

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$2,299,000

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

6 beds
6 baths
35 days

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, And Extensive Renovations Throughout,

House for sale: 18 MCCABE CRESCENT, Caledon

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$1,399,000

18 Mccabe Crescent, Caledon (Bolton North), Ontario L7E 5W9

4 beds
3 baths
34 days

Stunning Family Home in Desirable Bolton North - Welcome to this exceptional detached home in the highly sought-after community of Bolton North. Lovingly cared for by its original owner, this residence showcases true pride of ownership and has been meticulously maintained inside and out. Nestled

Listed by: Rosemarie James ,Royal Lepage Rcr Realty (705) 435-3000
House for sale: 4 INGLEVIEW DRIVE, Caledon

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$2,250,000

4 Ingleview Drive, Caledon (Inglewood), Ontario L7C 1P3

4 beds
4 baths
33 days

Luxurious Caledon escape awaits in this executive home. Refined country living meets exceptional convenience. Set on2beautifully groomed acres with private pond, this expansive, lovingly maintained bungalow offers an extraordinary lifestyle so close to the city. From the moment you arrive,

Nancy Prete,Exp Realty
Listed by: Nancy Prete ,Exp Realty (647) 909-8076
House for sale: 43 STRAWBERRY HILL COURT, Caledon

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$1,399,900

43 Strawberry Hill Court, Caledon (Bolton East), Ontario L7E 2M4

4 beds
4 baths
22 days

Rarely does a property of this calibre become available, where traditional elegance and contemporary design come together so beautifully. Filled with natural light and timeless charm, this impeccably maintained detached brick home is nestled on a quiet cul-de-sac in the highly sought-after

Listed by: Ray Jaro ,Century 21 People's Choice Realty Inc. (905) 760-8300
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
103 days

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 oasis featuring : Salt

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
93 days

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, secluded 1.88-acre lot,

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

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$2,500,000

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

4 beds
6 baths
92 days

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, secluded 1.88-acre lot,

Karen Hewson,Keller Williams Edge Realty
Listed by: Karen Hewson ,Keller Williams Edge Realty (905) 335-8808
House for sale: 17 SHANGRILA TERRACE, Caledon

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$1,199,000

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

5 beds
4 baths
75 days

This two-storey, 4-bedroom, 4-bathroom home with a finished walkout basement is a real crowd-pleaser. Family friendly area. Treed view. Boasting 2,356 sq. ft. plus the finished basement provides over 3000 sq. ft of living space. The main floor is bright and airy with hardwood flooring throughout.

Sandy Hopkinson,Century 21 Heritage Group Ltd.
Listed by: Sandy Hopkinson ,Century 21 Heritage Group Ltd. (905) 866-9443
House for sale: 249 LEAVENS COURT, Caledon

48 photos

$899,000

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

3 beds
3 baths
51 days

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 room with rough ins for future kitchen/laundry room.The open-concept main floor offers a fully

Listed by: Rob Schneider ,Century 21 B.j. Roth Realty Ltd. (705) 436-2121
House for sale: 4 WOLF CRESCENT, Caledon

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$1,939,900

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

4 beds
3 baths
43 days

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 direction, this is a place where nature takes centre stage - designed for active, everyday living.

House for sale: 13 DOCTOR REYNAR ROAD, Caledon

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$2,299,999

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

4 beds
5 baths
21 days

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 premium interior finishes

Listed by: Connie Bove ,Your Home Sold Guaranteed Realty Specialists Inc (416) 908-5408
House for sale: 26 SHADY GLEN CRESCENT, Caledon

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$1,026,000

26 Shady Glen Crescent, Caledon (Bolton East), Ontario L7E 2K4

5 beds
4 baths
16 days

Welcome to this meticulously maintained home nestled on a quiet, family-friendly cresent in Bolton's desirable South Hill! Offering over 2,000 sq. ft. of living space above grade + finished basement, this spacious home provides the perfect combination of comfort & functionality. Step into an

Francesca Valente,Re/max West Realty Inc.
Listed by: Francesca Valente ,Re/max West Realty Inc. (416) 436-4829
House for sale: 92 HEADWATER ROAD, Caledon

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$1,299,000

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

4 beds
4 baths
16 days

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 throughout. Step

Listed by: Anna Maria Bellissimo ,Re/max Premier Inc. (416) 987-8000

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.