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Pickering, ON Luxury Homes

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With Square Yards Canada, you can find your dream luxury homes for sale in Pickering. Explore your options from condo apartments, condo townhouses, detached houses, semi detached homes posted by agencies/owners who provide spacious and luxurious amenities in luxury houses for sale in Pickering

Last Updated: November 03, 2026

46 Photos

700 Hillcrest Road, Durham, ON , MLS #E13814076 , Image - 1

700 Hillcrest Road West Shore, Pickering, Durham, ON MLS® E13814076

Residential Freehold (Detached)

$2298000.0

4 Beds
5 Baths
3000-3500 sq-ft

A spectacular newly built custom home in the prestigious West Shore community, proudly recognized as the winning home featured on HGTV's Top of the Bl

Open House : Sun Nov 08, 02:00 PM to 04:00 PM

48 Photos

314 Dyson Road, Durham, ON , MLS #E14137490 , Image - 1

314 Dyson Road Rosebank, Pickering, Durham, ON MLS® E14137490

Residential Freehold (Detached)

$3400000.0

7 Beds
5 Baths
5000 + sq-ft

Your classic Toronto dream home reimagined in Pickering. A one-of-a-kind, lovingly crafted reproduction of an Annex/Rosedale home on a ravine lot, wit

48 Photos

4395 Westney Road N, Durham, ON , MLS #E14099108 , Image - 1

4395 Westney Road N Rural Pickering, Pickering, Durham, ON MLS® E14099108

Residential Freehold (Detached)

$2399000.0

4 +1 Beds
4 Baths
3000-3500 sq-ft

Welcome to this A One-of-a-Kind Private Country Estate. This extraordinary modern farmhouse is nestled on 7.91 acres, surrounded by nature and featuri

50 Photos

5295 - 5315 Sideline 16 Road, Durham, ON , MLS #E13819414 , Image - 1

5295 - 5315 Sideline 16 Road Rural Pickering, Pickering, Durham, ON MLS® E13819414

Residential Freehold (Rural Residential)

$9800000.0

8 Beds
6 Baths
3000-3500 sq-ft

Welcome to Happy Valley Estate featuring 3 beautiful homes on 50+ acres that is breathtaking with its unmatchable rolling hills scenery and privacy. T

Pre-Construction

1515 Pickering Parkway

1497-1525 Pickering Parkway, Pickering

From $399,990 - $706,990

Project Info

1 Building
571 Units
Condos

Property Mix

Studio(36)
1 Bed(451)
2 Bed(80)
3 Bed(2)

Developer:Sevoy Developments

50 Photos

3405 Sideline 4 Road, Durham, ON , MLS #E14127438 , Image - 1

3405 Sideline 4 Road Rural Pickering, Pickering, Durham, ON MLS® E14127438

Residential Freehold (Detached)

$3999000.0

3 +3 Beds
7 Baths
3500-5000 sq-ft

Crafted by award-winning Fourteen Estates, this extraordinary custom bungalow offers over 7,000 sq. ft. of impeccably finished living space on a profe

31 Photos

520 Gillmoss Road, Durham, ON , MLS #E14102766 , Image - 1

520 Gillmoss Road Rosebank, Pickering, Durham, ON MLS® E14102766

Residential Freehold (Detached)

$2600000.0

4 Beds
4 Baths
2500-3000 sq-ft

Developers/Builders Prime Residential Development Opportunity Rosebank Neighbourhood Pickering.(see Attachment) Land Area Over One-Acre Lot Frontage 2

39 Photos

5321 Old Brock Road, Durham, ON , MLS #E13702426 , Image - 1

5321 Old Brock Road Rural Pickering, Pickering, Durham, ON MLS® E13702426

Residential Freehold (Detached)

$3360000.0

4 +1 Beds
7 Baths
5000 + sq-ft

NEARLY NEW CUSTOM-BUILT GATED ESTATE offering over 8,700 sq. ft. of finished living space on expansive, fully fenced grounds approximately 147 x 332 f

41 Photos

1275 Wharf Street, Durham, ON , MLS #E13849130 , Image - 1

1275 Wharf Street Bay Ridges, Pickering, Durham, ON MLS® E13849130

Residential Freehold (Detached)

$2600000.0

4 Beds
3 Baths
2500-3000 sq-ft

An impressive 90 feet of private shoreline on Frenchman's Bay! This amazing property offers true direct and sheltered waterfront access a rarity anywh

Under Construction

The Grand at Universal City

1474 Bayly Street, Pickering

From $589,900-$766,900

Project Info

2 Buildings
758 Units
Condos

Property Mix

Studio(1)
1 Bed(485)
2 Bed(262)
3 Bed(45)

Developer:Chestnut Hill Developments

10 Photos

732 West Shore Boulevard, Durham, ON , MLS #E13851934 , Image - 1

732 West Shore Boulevard West Shore, Pickering, Durham, ON MLS® E13851934

Residential Freehold (Detached)

$2799000.0

5 +2 Beds
5 Baths
5000 + sq-ft

Experience refined waterfront community living in this extraordinary custom luxury residence,ideally situated in one of Pickering's most coveted lakes

45 Photos

1434 Rougemount Drive, Durham, ON , MLS #E14085760 , Image - 1

1434 Rougemount Drive Rougemount, Pickering, Durham, ON MLS® E14085760

Residential Freehold (Detached)

$2050000.0

4 +1 Beds
5 Baths
3500-5000 sq-ft

Welcome To One Of Pickering's Most Coveted Streets. This Exceptional Home On A VERY PRIVATE & PREMIUM 69 Ft. x 309 Ft. Lot Was Completely Rebuilt In 2

50 Photos

1985 Guild Road, Durham, ON , MLS #E14081566 , Image - 1

1985 Guild Road Village East, Pickering, Durham, ON MLS® E14081566

Residential Freehold (Detached)

$2499900.0

4 +1 Beds
6 Baths
3500-5000 sq-ft

Welcome home to 1985 Guild Rd, Custom-Built 4Br/5Ba Private Estate With Pristine Outdoor Living Space. A Three Car parking Garage On A Generous Lot!!!

37 Photos

492 Rougemount Drive, Durham, ON , MLS #E13875868 , Image - 1

492 Rougemount Drive Rosebank, Pickering, Durham, ON MLS® E13875868

Residential Freehold (Detached)

$3199900.0

7 Beds
5 Baths
5000 + sq-ft

Discover custom luxury in Pickering's Rosebank neighbourhood. Set on an expansive ravine lot near the beach, 492 Rougemount Drive offers elegant inter

50 Photos

4780 Westney Road, Durham, ON , MLS #E14032862 , Image - 1

4780 Westney Road Rural Pickering, Pickering, Durham, ON MLS® E14032862

Residential Freehold (Farm)

$2295000.0

5 +1 Beds
4 Baths
3000-3500 sq-ft

Welcome to 4780 Westney Rd N, a rare opportunity to own a completely turnkey, meticulously maintained executive home offering peaceful country living

50 Photos

1788 Loyst Avenue, Durham, ON , MLS #E13785938 , Image - 1

1788 Loyst Avenue Rural Pickering, Pickering, Durham, ON MLS® E13785938

Residential Freehold (Detached)

$2250000.0

4 Beds
4 Baths
3000-3500 sq-ft

There is a sense of ease to 1788 Loyst Ave that goes beyond its scale. Newly built by Geranium in Clarehaven Estates and backing onto conservation, th

30 Photos

1879 Appleview Road, Durham, ON , MLS #E13791792 , Image - 1

1879 Appleview Road Dunbarton, Pickering, Durham, ON MLS® E13791792

Residential Freehold (Detached)

$2499000.0

5 +3 Beds
6 Baths
3000-3500 sq-ft

Luxury living meets exceptional versatility in Pickering's highly sought-after Dunbarton community. This custom-built executive home offers over 5,000

50 Photos

3325 Hollywood Court, Durham, ON , MLS #E13814006 , Image - 1

3325 Hollywood Court Rural Pickering, Pickering, Durham, ON MLS® E13814006

Residential Freehold (Detached)

$4995000.0

5 +2 Beds
9 Baths
5000 + sq-ft

Set in a quiet enclave of prestigious homes, this exceptional 11,500 sq. ft. estate (including built in garage) sits on a private1.5-acre lot backing

16 Photos

600 Liverpool Road W, Durham, ON , MLS #E8120124 , Image - 1

600 Liverpool Road W Bay Ridges, Pickering, Durham, ON MLS® E8120124

Residential Freehold (Detached)

$40000000.0

4 Baths
< 700 sq-ft

See Virtual Tour**A Must See** Lake Ontario (34 Acres) Frenchmans Bay (134 Acres) Zoned R4 Residential. This Is A Once In A Lifetime Opportunity To Bu

28 Photos

253 Martins Street, Durham, ON , MLS #E13875464 , Image - 1

253 Martins Street Rural Pickering, Pickering, Durham, ON MLS® E13875464

Residential Freehold (Detached)

$7259000.0

5 +1 Beds
10 Baths
5000 + sq-ft

Introducing The Martins Estate. A statement residence where scale, craftsmanship and sophisticated design come together in one of Pickering's most exc

26 Photos

413 Sheppard Avenue, Durham, ON , MLS #E13859658 , Image - 1

413 Sheppard Avenue Woodlands, Pickering, Durham, ON MLS® E13859658

Residential Freehold (Detached)

$2299000.0

4 +2 Beds
6 Baths
3500-5000 sq-ft

Detached home in Pickering's Woodlands community, offering 4,920 sq. ft. above grade, 4+2bedrooms and 6 bathrooms. Built in 2020, with a finished walk

48 Photos

1837 New Street, Durham, ON , MLS #E13774984 , Image - 1

1837 New Street Amberlea, Pickering, Durham, ON MLS® E13774984

Residential Freehold (Detached)

$2798800.0

4 Beds
5 Baths
3500-5000 sq-ft

Brand New Elegant Custom Home Situated On A Rare Premium 71-Ft Wide Lot In Sought-After Amberlea! This Home Showcases Exceptional Craftsmanship and T

49 Photos

3850 Kinsale Road, Durham, ON , MLS #E12925496 , Image - 1

3850 Kinsale Road Rural Pickering, Pickering, Durham, ON MLS® E12925496

Residential Freehold (Detached)

$3288888.0

4 +3 Beds
6 Baths
5000 + sq-ft

Welcome To Your New Custom Built Estate Home! This Stunning Property Offers Unparalleled Luxury and Privacy on a Premium Ravine Lot Backing Directly O

38 Photos

1436 Highbush Trail, Durham, ON , MLS #E13831620 , Image - 1

1436 Highbush Trail Woodlands, Pickering, Durham, ON MLS® E13831620

Residential Freehold (Detached)

$2250000.0

4 Beds
4 Baths
3500-5000 sq-ft

Welcome to this custom built, Victorian farmhouse-style home on a double premium lot backing onto tranquil Petticoat Creek in one of Pickering's most

50 Photos

3395 Pickering Uxbridge Townline, Durham, ON , MLS #E13533054 , Image - 1

3395 Pickering Uxbridge Townline Rural Pickering, Pickering, Durham, ON MLS® E13533054

Residential Freehold (Detached)

$5495000.0

Price drop by 6.9%

4 +3 Beds
5 Baths
3500-5000 sq-ft

There are properties that impress. And there are properties that change the way you live. Set across an extraordinary 62 acres, this custom-built esta

19 Photos

2950 9th Concession Road, Durham, ON , MLS #E13821298 , Image - 1

2950 9th Concession Road Rural Pickering, Pickering, Durham, ON MLS® E13821298

Residential Freehold (Vacant Land)

$4900000.0

A rare chance to secure more than 122 acres of picturesque land in the sought-after Balsam Village area. Set along a year-round municipal road, this e

7 Photos

1939 Altona Road, Durham, ON , MLS #E13813044 , Image - 1

1939 Altona Road Highbush, Pickering, Durham, ON MLS® E13813044

Residential Freehold (Detached)

$7900000.0

Price drop by 18.6%

3 Beds
2 Baths
1100-1500 sq-ft

INFILL Townhome Development Site in Pickering. 57 Units. 11 Traditional Towns Backing Onto Altona Forest. 46 Large Stacked Towns, ( 3 bed 3 bath, w

50 Photos

1472 Highbush Trail, Durham, ON , MLS #E13684770 , Image - 1

1472 Highbush Trail Woodlands, Pickering, Durham, ON MLS® E13684770

Residential Freehold (Detached)

$2769000.0

Price drop by 2.8%

4 +1 Beds
4 Baths
3500-5000 sq-ft

(PRIVATE ELEVATOR SERVICING ALL FLOORS ) A Rare Expression Of Luxury, Space & Sophisticated Family Living, This Magnificent Custom-Built Residence Off

40 Photos

2300 Rosebank Road, Durham, ON , MLS #E13488844 , Image - 1

2300 Rosebank Road Rural Pickering, Pickering, Durham, ON MLS® E13488844

Residential Freehold (Detached)

$4299900.0

4 Beds
1 Baths
1500-2000 sq-ft

Where else can you find a parcel of land this large, this close to the city? A SPECTACULAR 14.34 acres of prime real estate. A rare, magnificent gem!

49 Photos

5050 William Street, Durham, ON , MLS #E13741468 , Image - 1

5050 William Street Rural Pickering, Pickering, Durham, ON MLS® E13741468

Residential Freehold (Detached)

$2599900.0

6 +2 Beds
7 Baths
5000 + sq-ft

Welcome to an extraordinary Claremont estate that blends luxury, privacy, and natural beauty.-This home must be experienced to be fully appreciated. S

49 Photos

2342 Heska Road, Durham, ON , MLS #E13692556 , Image - 1

2342 Heska Road Rural Pickering, Pickering, Durham, ON MLS® E13692556

Residential Freehold (Detached)

$2999088.0

4 +1 Beds
8 Baths
5000 + sq-ft

Private Backyard Oasis & Country-Style Living Minutes From the City! Welcome to 2342 Heska Road! Situated on an impressive 100 ft x 167 ft lot in desi

11 Photos

3315 Hwy 7 Highway, Durham, ON , MLS #E13673826 , Image - 1

3315 Hwy 7 Highway Rural Pickering, Pickering, Durham, ON MLS® E13673826

Residential Freehold (Detached)

$2800000.0

1 Beds
1 Baths
1100-1500 sq-ft

PRIME 6.58-ACRE STRATEGIC LAND HOLDING IN PICKERING! Exceptional opportunity positioned directly in the path of rapid urban expansion. This massive la

Shortlisted Properties

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Pickering, ON Luxury Homes

1515 Pickering Parkway

The Grand at Universal City

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