Caledon Homes With Pools

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House for sale: 14294 WINSTON CHURCHILL BOULEVARD, Caledon

49 photos

$2,389,000

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

4 beds
3 baths
76 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: 17397 HUMBER STATION ROAD, Caledon

49 photos

$2,389,900

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

4 beds
4 baths
114 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: 15466 THE GORE ROAD, Caledon

40 photos

$17,800,000

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

7 beds
9 baths
11 days

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

House for sale: 14812 CENTREVILLE CREEK ROAD, Caledon

48 photos

$2,078,000

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

5 beds
4 baths
40 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: 11 HILLTOP DRIVE, Caledon

46 photos

$989,000

11 Hilltop Drive, Caledon (Caledon East), Ontario L7C 1K7

3 beds
2 baths
2 days

Airport Rd/Hilltop Dr Dreaming of Summer? Have a look at this beauty with backyard oasis complete with inground pool and hot tub! Nestled within one of Caledon East's most sought after family friendly area where tree-lined streets, generous lots, and a calm, welcoming atmosphere define everyday

Cheryl Robb,Royal Lepage Rcr Realty
Listed by: Cheryl Robb ,Royal Lepage Rcr Realty (416) 805-1316
House for sale: 27 BRIARWOOD DRIVE, Caledon

30 photos

$1,600,000

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

5 beds
4 baths
61 days

Cross Streets: St Andrews/ Hwy 9 /Beechgroove. ** Directions: St Andrews/ Hwy 9. 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 home is perfectly

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
144 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: 28 LARRY STREET, Caledon

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$1,295,000

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

4 beds
3 baths
13 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

Listed by: Matthew Petrovich ,Keller Williams Experience Realty (705) 720-2200
House for sale: 88 WALKER ROAD W, Caledon

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$1,198,000

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

5 beds
3 baths
43 days

Cross Streets: Walker Rd & Airport Rd. ** Directions: Heading North on Airport Rd. Turn Left onto Walker Rd W. 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

Eran Williamson,Royal Lepage Rcr Realty
Listed by: Eran Williamson ,Royal Lepage Rcr Realty (416) 824-7685
House for sale: 17088 HORSESHOE HILL ROAD, Caledon

50 photos

$2,499,900

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

5 beds
5 baths
8 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: 16672 CENTREVILLE CREEK ROAD, Caledon

48 photos

$3,390,000

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

5 beds
3 baths
69 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: 9 FLAHERTY LANE, Caledon

49 photos

$6,399,000

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

6 beds
10 baths
37 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: 4 BLUE HORIZON COURT, Caledon

26 photos

$1,699,999

4 Blue Horizon Court, Caledon (Caledon Village), Ontario L7K 0V1

5 beds
4 baths
23 days

Cross Streets: Hwy 10 & Hwy 24 (Charleston Sideroad). ** Directions: -. Enjoy countryside lifestyle living closer to CITY !!! feels like Cottage living !!! Immaculate And Fully Renovated 4 Level Split Detached Home. 4+1 Bedrooms/ 4 Washrooms. Finished Basement with Bedroom/ Kitchen. Delightful

Bill Mahey,Re/max Realty Services Inc.
Listed by: Bill Mahey ,Re/max Realty Services Inc. (416) 831-7673
House for sale: 39 PINEBROOK CIRCLE, Caledon

50 photos

$1,649,900

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

6 beds
5 baths
28 days

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

House for sale: 47 LARRY STREET, Caledon

45 photos

$1,247,000

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

3 beds
2 baths
39 days

Airport / Larry This spectacular property is located in one of the most sought-after neighborhood 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: 40 HILLTOP DRIVE, Caledon

50 photos

$1,399,900

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 beautifully updated 4-bedroom, 3-bathroom home set on nearly half an acre backing onto serene green space and trails.The renovated main floor showcases rich hardwood flooring, updated stairs, crown moulding,

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
114 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: 2097 GRANGE SIDE ROAD, Caledon

39 photos

$9,985,000

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

9 beds
9 baths
95 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: 43 OLIVERS LANE, Caledon

50 photos

$1,599,999

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

4 beds
3 baths
9 days

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

House for sale: 7 WALKER ROAD E, Caledon

50 photos

$1,450,000

7 Walker Road E, Caledon (Caledon East), Ontario L7C 1G8

4 beds
3 baths
27 days

Cross Streets: Airport Rd / Walker Rd. ** Directions: Airport Rd to Walker Rd E. All Brick Home on a Premium Lot of 69 ft x 154 ft. Located In Caledon East. 4 Bedroom, 3 Washrooms, 8 Parking Spots, 4 Level Side Split Is Fully Upgraded Home, Hardwood Floors, Porcelain Tiles in Foyer and Kitchen,

Daljit Gulati,Re/max Paramount Realty
Listed by: Daljit Gulati ,Re/max Paramount Realty (416) 803-0600
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
94 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: 4 BRETHBY STREET, Caledon

46 photos

$1,319,000

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

5 beds
5 baths
15 days

Kennedy & Learmont 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. Beautiful subdivision of homes on the border of Brampton & Caledon.

Listed by: Tina E. O'brien ,Sutton Group Quantum Realty Inc. (905) 822-5000
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
116 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: 32 COTTONFIELD CIRCLE, Caledon

49 photos

$1,649,900

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

5 beds
5 baths
81 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: 32 CALEDON STREET, Caledon

33 photos

$1,099,999

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

5 beds
3 baths
87 days

Cross Streets: MAIN ST?QUEEN ST W. ** Directions: 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

Listed by: Manveer Singh Dhindsa ,Re/max Realty Services Inc. (905) 456-1000
House for sale: 110 PALMER CIRCLE, Caledon

46 photos

$1,677,500

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

4 beds
4 baths
24 days

Cross Streets: North of Old Church B/W Hwy 50 & Mt Hope. ** Directions: palmer circle x walton dr. Discover Caledon living at its finest. 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

House for sale: 70 SILVERVALLEY DRIVE, Caledon

49 photos

$1,499,990

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

5 beds
4 baths
20 days

Cross Streets: Evans Ridge / King St. N. ** Directions: N on Hwy 50, E on King, Left on Evans Ridge, L Silvervalley. Rare Opportunity To Own A Beautiful Spacious Home With A Great Layout In A Sought After Bolton Neighbourhood. Enjoy Privacy, Nature And Gorgeous Views All Year Round From Your

Listed by: Rosanna Schembri ,Kingsway Real Estate (905) 277-2000
House for sale: 43 MCCANDLESS Court, Caledon East

44 photos

$1,499,900

43 Mccandless Court, Caledon East, Ontario L7C 3R6

4 beds
4 baths
27 days

Paisley Green & McCandless Crt Set on a quiet court in Caledon East, this refined family home is positioned on a premium corner lot surrounded by parks, trails, and the Caledon East Community Complex, offering a pool, gym, walking track, and ice rink. The corner setting allows for additional

House for sale: 26 WRIGHT CRESCENT, Caledon

34 photos

$1,119,000

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

3 beds
2 baths
6 days

Cross Streets: Kingsview/ Wright Cres. ** Directions: Hwy 50/ Bolton Heights/ Kingsview to Wright Cres. Immaculate, fully renovated home on one of the best streets in the North Hill. This huge cornet lot on a quiet crescent boasts a very spacious, fully fenced, entertainers dream backyard with

Laura Elizabeth Smith,Lpt Realty
Listed by: Laura Elizabeth Smith ,Lpt Realty (416) 660-1115
House for sale: 258 AMOS DRIVE, Caledon

50 photos

$3,858,000

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

4 beds
5 baths
94 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: 33 GIBSON LAKE DRIVE, Caledon

45 photos

$2,225,000

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

3 beds
4 baths
135 days

Cross Streets: Gibson Lake Drive and Lakeview Place. ** Directions: Hwy 50 and Gibson Lake Drive. 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,

House for sale: 67 SHERIN COURT, Caledon

50 photos

$1,190,000

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

4 beds
3 baths
65 days

King / Humberlea Best-Kept Secret! A secluded paradise in Bolton's prestigious North Hill Court. This unique property features a beautifully renovated home highlighted by a warm wood-rustic vibe throughout. The open-concept main floor includes an entertainer's dream kitchen island, stylish

Listed by: Sandeep Singh ,Re/max Millennium Real Estate (647) 300-3600
House for sale: 62 GIBSON LAKE DRIVE, Caledon

50 photos

$1

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

4 beds
5 baths
85 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: 172 BELL AIR DRIVE, Caledon

29 photos

$2,299,000

172 Bell Air Drive, Caledon (Bolton East), Ontario L7E 2A2

5 beds
4 baths
15 days

Bell Air/ Ellwood/ Hwy 50 Exceptional Detached Home on a 12,000 Sq Ft Lot in the Heart of Bolton. Welcome to this stunning 2-storey fully detached home situated on a rare flat lot backing onto a serene ravine. Completely rebuilt interior and custom-renovated just 4 years ago, this home offers

Listed by: Anna Mistal ,Intercity Realty Inc. (416) 798-7070
House for sale: 100 HUMBER LEA ROAD, Caledon

19 photos

$1,069,900

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

4 beds
2 baths
116 days

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

Listed by: Joe Bilotta ,Right At Home Realty (905) 665-2500
House for sale: 50 WILLOW STREET, Caledon

43 photos

$1,599,000

50 Willow Street, Caledon (Bolton East), Ontario L7E 1C4

4 beds
5 baths
69 days

Highway 50 & Willow st Stunning, Light-Filled Home in the heart of Bolton. Welcome to the perfect blend of modern living and small-town charm. This beautifully updated home offers spacious, open-concept living on an exceptional lot. Enjoy the convenience of being minutes away from everything

Listed by: Diljot Chahal ,Re/max Gold Realty Inc. (905) 673-8500
House for sale: 1762 QUEEN STREET, Caledon

50 photos

$1,349,000

1762 Queen Street, Caledon (Alton), Ontario L7K 2N6

4 beds
2 baths
142 days

Queen Street/Main Street Tucked away in the scenic hamlet of Alton, Ontario, just steps from the area's best hiking trails, world-class golf, local artisan shops & fine dining, this charming modern rustic log home is a rare opportunity to own a slice of serenity w/o compromising on convenience.

House for sale: 14 CALEDON CRESCENT, Brampton

50 photos

$849,999

14 Caledon Crescent, Brampton (Brampton East), Ontario L6W 1C5

4 beds
2 baths
14 days

Kennedy Rd & Steeles Ave E Great Deal For Sale. Detached Home With Large Driveway Located In Peel Village. Offers Anytime. Pre-Listing Inspection Report Available Upon Request. This Well Maintained Home Is Situated On A Quiet Crescent. Irregular Lot At 47.81 Feet By 100.08 Feet With Rear 59.67

Nick Cuong Chuong,Lpt Realty
Listed by: Nick Cuong Chuong ,Lpt Realty (647) 299-4062
House for sale: 5211 TENTH LINE, Erin

50 photos

$7,250,000

5211 Tenth Line, Erin (Rural Erin), Ontario N0B 1T0

5 beds
6 baths
140 days

Tenth Line / Side Rd 5 A soulful modern residence designed to sync with the rhythm of the sun, offering incredible vistas from all spaces & making an effortless connection between indoors & out. Nestled on approx. 98 acres in the bucolic countryside of Erin, bordering Caledon, a long heritage

Jade Skuce,Royal Lepage Rcr Realty
Listed by: Jade Skuce ,Royal Lepage Rcr Realty (519) 941-5151
House for sale: 2139 ADJALA-TECUMSETH TOWNLINE, New Tecumseth

20 photos

$825,000

2139 Adjala-tecumseth Townline, New Tecumseth (Rural New Tecumseth), Ontario L0G 1W0

5 beds
2 baths
14 days

Cross Streets: 5th Line/Adjala-Tecumseth Townline. ** Directions: 5th Line/Adjala -Tecumseth Townline. THE OUTDOOR FREEDOM YOU CRAVE WITH INDOOR SPACE THAT LETS YOU DREAM BIG! It's the kind of property that catches you off guard in the best way because it offers peaceful country living with

House for sale: 119 SUNDRIDGE STREET, Brampton

26 photos

$898,888

119 Sundridge Street, Brampton (Snelgrove), Ontario L7A 1J8

3 beds
2 baths
80 days

Cross Streets: Hurontario / Mayfield. ** Directions: HWY 10 to Mayfield. Now is the time to get into your new home!!! This is a spectacular 1+2 bedroom on a HUGE oversized pie shape lot with an in-ground, saltwater swimming pool! This raised bungalow has it all, and with the opportunity to

Stephanie Kortekaas,Royal Lepage Rcr Realty
Listed by: Stephanie Kortekaas ,Royal Lepage Rcr Realty (416) 220-6397
House for sale: 159 DELARMBRO DRIVE, Erin

43 photos

$1,899,000

159 Delarmbro Drive, Erin (Erin), Ontario N0B 1T0

4 beds
3 baths
104 days

Cross Streets: Wellington 52 & 8th Line. ** Directions: Google Maps. Welcome to 159 Delarmbro Drive - a beautifully upgraded executive estate home set in one of Erin's most coveted family friendly communities. Peaceful, private, and surrounded by mature trees, this residence blends timeless

Tina Sadler,Re/max Real Estate Centre Inc.
Listed by: Tina Sadler ,Re/max Real Estate Centre Inc. (647) 984-8079

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.