✨ Luxury ($2M+) in Pickering

Luxury Homes for Sale in Pickering

High-end custom builds, acreage properties, and executive homes. Browse real-time MLS® listings, updated every 15 minutes with complete photo galleries and price histories.

Active Listings36Properties available
🔥 Price Drops🏡 Bungalows🏘️ Townhouses🏰 Detached Homes🏢 Condos💰 Under $800k🏷️ Under $750k🎯 Under $1M✨ Luxury ($2M+)🔑 In-Law Suites🔨 Fixer-Uppers🏊 Inground & Heated Pools🌊 Waterfront & Views🏢 Multi-Family & Duplex🏗️ New Construction
Residential Freehold for sale - 4 Bed, 4 Bath Home at 520 Gillmoss Road Pickering ON listed at $2,600,000 (MLS# E14102766)
Added 2 days ago
$2,600,000Est. $8,654/mo
4bd
4ba
Residential Freehold

520 Gillmoss Road, Pickering

Oct 21, 2026
DOM: 3

Developers/Builders Prime Residential Development Opportunity Rosebank Neighbourhood Pickering.(see ...

MLS#: E14102766
For Sale
Commercial for sale - 0 Bed, 0 Bath Home at 3830 Lake Ridge Road Pickering ON listed at $10,900,000 (MLS# E14095512)
Added 4 days ago
$10,900,000Est. $36,282/mo
0bd
0ba
Commercial

3830 Lake Ridge Road, Pickering

Oct 19, 2026
DOM: 5

39.16-acre landholding with dual frontage on Highway 7 and Lake Ridge Road, directly opposite the ap...

MLS#: E14095512
For Sale
Residential Freehold for sale - 5 Bed, 5 Bath Home at 1434 Rougemount Drive Pickering ON listed at $2,050,000 (MLS# E14085760)
Added 7 days ago
$2,050,000Est. $6,824/mo
5bd
5ba
Residential Freehold

1434 Rougemount Drive, Pickering

Oct 16, 2026
DOM: 8

Welcome To One Of Pickering's Most Coveted Streets. This Exceptional Home On A "VERY PRIVATE & PREMI...

MLS#: E14085760
For Sale
Residential Freehold for sale - 5 Bed, 6 Bath Home at 1985 Guild Road Pickering ON listed at $2,499,900 (MLS# E14081566)
Added 8 days ago
$2,499,900Est. $8,321/mo
5bd
6ba
Residential Freehold

1985 Guild Road, Pickering

Oct 15, 2026
DOM: 9

Welcome home to 1985 Guild Rd, Custom-Built 4Br/5Ba Private Estate With Pristine Outdoor Living Spac...

MLS#: E14081566
For Sale
Residential Freehold for sale - 6 Bed, 4 Bath Home at 4780 Westney Road Pickering ON listed at $2,295,000 (MLS# E14032862)
Added 9 days ago
$2,295,000Est. $7,639/mo
6bd
4ba
Residential Freehold

4780 Westney Road, Pickering

Oct 14, 2026
DOM: 10

Welcome to 4780 Westney Rd N, a rare opportunity to own a completely turnkey, meticulously maintaine...

MLS#: E14032862
For Sale
Residential Freehold for sale - 6 Bed, 10 Bath Home at 253 Martins Street Pickering ON listed at $7,259,000 (MLS# E13875464)
$7,259,000Est. $24,163/mo
6bd
10ba
Residential Freehold

253 Martins Street, Pickering

Oct 8, 2026
DOM: 16

Introducing The Martins Estate. A statement residence where scale, craftsmanship and sophisticated d...

MLS#: E13875464
For Sale
Residential Freehold for sale - 7 Bed, 5 Bath Home at 492 Rougemount Drive Pickering ON listed at $3,199,900 (MLS# E13875868)
$3,199,900Est. $10,651/mo
7bd
5ba
Residential Freehold

492 Rougemount Drive, Pickering

Oct 8, 2026
DOM: 16

Discover custom luxury in Pickering's Rosebank neighbourhood. Set on an expansive ravine lot near th...

MLS#: E13875868
For Sale
Residential Freehold for sale - 6 Bed, 6 Bath Home at 413 Sheppard Avenue Pickering ON listed at $2,299,000 (MLS# E13859658)
$2,299,000Est. $7,653/mo
6bd
6ba
Residential Freehold

413 Sheppard Avenue, Pickering

Oct 2, 2026
DOM: 22

Detached home in Pickering's Woodlands community, offering 4,920 sq. ft. above grade, 4+2bedrooms an...

MLS#: E13859658
For Sale
Residential Freehold for sale - 4 Bed, 3 Bath Home at 1275 Wharf Street Pickering ON listed at $2,600,000 (MLS# E13849130)
$2,600,000Est. $8,654/mo
4bd
3ba
Residential Freehold

1275 Wharf Street, Pickering

Oct 1, 2026
DOM: 23

An impressive 90 feet of private shoreline on Frenchman's Bay! This amazing property offers true dir...

MLS#: E13849130
For Sale
Residential Freehold for sale - 7 Bed, 5 Bath Home at 732 West Shore Boulevard Pickering ON listed at $2,799,000 (MLS# E13851934)
$2,799,000Est. $9,317/mo
7bd
5ba
Residential Freehold

732 West Shore Boulevard, Pickering

Sep 30, 2026
DOM: 24

Experience refined waterfront community living in this extraordinary custom luxury residence,ideally...

MLS#: E13851934
For Sale
Commercial for sale - 0 Bed, 0 Bath Home at 3700 Salem Road Pickering ON listed at $2,250,000 (MLS# E13838304)
$2,250,000Est. $7,489/mo
0bd
0ba
Commercial

3700 Salem Road, Pickering

Sep 28, 2026
DOM: 26

A unique commercial opportunity situated on approximately 1.94 acres of land. This bungalow style pr...

MLS#: E13838304
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 1436 Highbush Trail Pickering ON listed at $2,250,000 (MLS# E13831620)
$2,250,000Est. $7,489/mo
4bd
4ba
Residential Freehold

1436 Highbush Trail, Pickering

Sep 26, 2026
DOM: 28

Welcome to this custom built, Victorian farmhouse-style home on a double premium lot backing onto tr...

MLS#: E13831620
For Sale
Commercial for sale - 0 Bed, 0 Bath Home at 1939 Altona Road Pickering ON listed at $7,900,000 (MLS# E13813014)
Price Change
$7,900,000Est. $26,296/mo
0bd
0ba
Commercial

1939 Altona Road, Pickering

Sep 22, 2026
DOM: 32

INFILL Townhome Development Site in Pickering. 57 Units. 11 Traditional Street Towns Backing Onto Al...

MLS#: E13813014
For Sale
Residential Freehold for sale - 3 Bed, 2 Bath Home at 1939 Altona Road Pickering ON listed at $7,900,000 (MLS# E13813044)
Price Change
$7,900,000Est. $26,296/mo
3bd
2ba
Residential Freehold

1939 Altona Road, Pickering

Sep 22, 2026
DOM: 32

INFILL Townhome Development Site in Pickering. 57 Units. 11 Traditional Towns Backing Onto Altona Fo...

MLS#: E13813044
For Sale
Residential Freehold for sale - 7 Bed, 9 Bath Home at 3325 Hollywood Court Pickering ON listed at $4,995,000 (MLS# E13814006)
$4,995,000Est. $16,627/mo
7bd
9ba
Residential Freehold

3325 Hollywood Court, Pickering

Sep 22, 2026
DOM: 32

Set in a quiet enclave of prestigious homes, this exceptional 11,500 sq. ft. estate (including built...

MLS#: E13814006
For Sale
Residential Freehold for sale - 4 Bed, 5 Bath Home at 700 Hillcrest Road Pickering ON listed at $2,298,000 (MLS# E13814076)
$2,298,000Est. $7,649/mo
4bd
5ba
Residential Freehold

700 Hillcrest Road, Pickering

Sep 22, 2026
DOM: 32

A spectacular newly built custom home in the prestigious West Shore community, proudly recognized as...

MLS#: E13814076
For Sale
Commercial for sale - 0 Bed, 0 Bath Home at 3680 Highway 7 Highway Pickering ON listed at $4,900,000 (MLS# E13810978)
$4,900,000Est. $16,310/mo
0bd
0ba
Commercial

3680 Highway 7 Highway, Pickering

Sep 21, 2026
DOM: 33

RARE 9.84 ACRE LAND OPPORTUNITY ON HIGHWAY 7 IN PICKERING! An exceptional opportunity to secure a su...

MLS#: E13810978
For Sale
Residential Freehold for sale - 0 Bed, 0 Bath Home at 2950 9th Concession Road Pickering ON listed at $4,900,000 (MLS# E13821298)
$4,900,000Est. $16,310/mo
0bd
0ba
Residential Freehold

2950 9th Concession Road, Pickering

Sep 21, 2026
DOM: 33

A rare chance to secure more than 122 acres of picturesque land in the sought-after Balsam Village a...

MLS#: E13821298
For Sale
Residential Freehold for sale - 8 Bed, 6 Bath Home at 1879 Appleview Road Pickering ON listed at $2,499,000 (MLS# E13791792)
$2,499,000Est. $8,318/mo
8bd
6ba
Residential Freehold

1879 Appleview Road, Pickering

Sep 15, 2026
DOM: 39

Luxury living meets exceptional versatility in Pickering's highly sought-after Dunbarton community. ...

MLS#: E13791792
For Sale
Residential Freehold for sale - 4 Bed, 5 Bath Home at 1837 New Street Pickering ON listed at $2,798,800 (MLS# E13774984)
$2,798,800Est. $9,316/mo
4bd
5ba
Residential Freehold

1837 New Street, Pickering

Sep 11, 2026
DOM: 43

Brand New Elegant Custom Home Situated On A Rare Premium 71-Ft Wide Lot In Sought-After Amberlea! Th...

MLS#: E13774984
For Sale
Residential Freehold for sale - 8 Bed, 7 Bath Home at 5050 William Street Pickering ON listed at $2,599,900 (MLS# E13741468)
$2,599,900Est. $8,654/mo
8bd
7ba
Residential Freehold

5050 William Street, Pickering

Sep 3, 2026
DOM: 51

Welcome to an extraordinary Claremont estate that blends luxury, privacy, and natural beauty.-This h...

MLS#: E13741468
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 1488 Rosebank Road Pickering ON listed at $2,180,000 (MLS# E13707836)
$2,180,000Est. $7,256/mo
4bd
4ba
Residential Freehold

1488 Rosebank Road, Pickering

Aug 24, 2026
DOM: 61

Welcome to a "Home & Garden" on a T-Shape of 1/2 ACRE Lot (21033.50 sq. ft). This is an elegant gem ...

MLS#: E13707836
For Sale
Residential Freehold for sale - 5 Bed, 7 Bath Home at 5321 Old Brock Road Pickering ON listed at $3,360,000 (MLS# E13702426)
Price Change
$3,360,000Est. $11,184/mo
5bd
7ba
Residential Freehold

5321 Old Brock Road, Pickering

Aug 21, 2026
DOM: 64

NEARLY NEW CUSTOM-BUILT GATED ESTATE offering over 8,700 sq. ft. of finished living space on expansi...

MLS#: E13702426
For Sale
Residential Freehold for sale - 5 Bed, 8 Bath Home at 2342 Heska Road Pickering ON listed at $2,999,088 (MLS# E13692556)
$2,999,088Est. $9,983/mo
5bd
8ba
Residential Freehold

2342 Heska Road, Pickering

Aug 19, 2026
DOM: 66

Private Backyard Oasis & Country-Style Living Minutes From the City! Welcome to 2342 Heska Road! Sit...

MLS#: E13692556
For Sale
Residential Freehold for sale - 5 Bed, 4 Bath Home at 1472 Highbush Trail Pickering ON listed at $2,769,000 (MLS# E13684770)
Price Change
$2,769,000Est. $9,217/mo
5bd
4ba
Residential Freehold

1472 Highbush Trail, Pickering

Aug 17, 2026
DOM: 68

(PRIVATE ELEVATOR SERVICING ALL FLOORS ) A Rare Expression Of Luxury, Space & Sophisticated Family L...

MLS#: E13684770
For Sale
Residential Freehold for sale - 1 Bed, 1 Bath Home at 3315 Hwy 7 Highway Pickering ON listed at $2,800,000 (MLS# E13673826)
$2,800,000Est. $9,320/mo
1bd
1ba
Residential Freehold

3315 Hwy 7 Highway, Pickering

Aug 13, 2026
DOM: 72

PRIME 6.58-ACRE STRATEGIC LAND HOLDING IN PICKERING! Exceptional opportunity positioned directly in ...

MLS#: E13673826
For Sale
Residential Freehold for sale - 6 Bed, 7 Bath Home at 3405 Sideline 4 Road Pickering ON listed at $3,999,000 (MLS# E13538946)
$3,999,000Est. $13,311/mo
6bd
7ba
Residential Freehold

3405 Sideline 4 Road, Pickering

Jul 8, 2026
DOM: 108

Crafted by award-winning Fourteen Estates, this extraordinary custom bungalow offers over 7,000 sq. ...

MLS#: E13538946
For Sale
Residential Freehold for sale - 7 Bed, 5 Bath Home at 3395 Pickering Uxbridge Townline Pickering ON listed at $5,495,000 (MLS# E13533054)
Price Change
$5,495,000Est. $18,291/mo
7bd
5ba
Residential Freehold

3395 Pickering Uxbridge Townline, Pickering

Jul 7, 2026
DOM: 109

There are properties that impress. And there are properties that change the way you live. Set across...

MLS#: E13533054
For Sale
Residential Freehold for sale - 5 Bed, 5 Bath Home at 752 Hillview Crescent Pickering ON listed at $2,395,000 (MLS# E13497058)
Price Change
$2,395,000Est. $7,972/mo
5bd
5ba
Residential Freehold

752 Hillview Crescent, Pickering

Jun 27, 2026
DOM: 119

Welcome to this elegant, custom-built family home, where no expense was spared in achieving the fine...

MLS#: E13497058
For Sale
Residential Freehold for sale - 5 Bed, 5 Bath Home at 968 Essa Crescent Pickering ON listed at $2,500,000 (MLS# E13492252)
$2,500,000Est. $8,322/mo
5bd
5ba
Residential Freehold

968 Essa Crescent, Pickering

Jun 26, 2026
DOM: 120

A rare opportunity to own one of Pickering's most spectacular waterfront residences. This custom-bui...

MLS#: E13492252
For Sale
Residential Freehold for sale - 4 Bed, 1 Bath Home at 2300 Rosebank Road Pickering ON listed at $4,299,900 (MLS# E13488844)
$4,299,900Est. $14,313/mo
4bd
1ba
Residential Freehold

2300 Rosebank Road, Pickering

Jun 25, 2026
DOM: 121

Where else can you find a parcel of land this large, this close to the city? A SPECTACULAR 14.34 acr...

MLS#: E13488844
For Sale
Residential Freehold for sale - 5 Bed, 6 Bath Home at 1921 Bonita Avenue Pickering ON listed at $3,300,000 (MLS# E13220994)
$3,300,000Est. $10,984/mo
5bd
6ba
Residential Freehold

1921 Bonita Avenue, Pickering

Jun 1, 2026
DOM: 145

Exquisite Custom-Built Home in Prestigious Pickering Neighbourhood. Soaring 10' Ceilings on the Main...

MLS#: E13220994
For Sale
Residential Freehold for sale - 7 Bed, 7 Bath Home at 1427 Rosebank Road Pickering ON listed at $2,649,000 (MLS# E13170706)
$2,649,000Est. $8,818/mo
7bd
7ba
Residential Freehold

1427 Rosebank Road, Pickering

May 25, 2026
DOM: 152

Absolutely Stunning 4 years Brand new Custom built Luxury Detached home, Approx 4200 Sq Ft Grand Liv...

MLS#: E13170706
For Sale
Commercial for sale - 0 Bed, 0 Bath Home at 755 OKLAHOMA Drive Pickering ON listed at $5,500,000 (MLS# E13152226)
$5,500,000Est. $18,307/mo
0bd
0ba
Commercial

755 OKLAHOMA Drive, Pickering

May 20, 2026
DOM: 157

PICKERING DEVELOPMENT SITE | DRAFT PLAN APPROVED Rare 1.146-acre redevelopment opportunity with draf...

MLS#: E13152226
For Sale
Commercial for sale - 0 Bed, 0 Bath Home at 820 Kingston Road Pickering ON listed at $12,090,000 (MLS# E13038834)
$12,090,000Est. $40,243/mo
0bd
0ba
Commercial

820 Kingston Road, Pickering

Apr 22, 2026
DOM: 185

18,657 sf fully leased retail plaza with potential future drive-thru and 16 approved townhomes. The ...

MLS#: E13038834
For Sale
Commercial for sale - 0 Bed, 0 Bath Home at 1192 & 1200 Kingston Rd. Road Pickering ON listed at $2,798,800 (MLS# E13021442)
$2,798,800Est. $9,316/mo
0bd
0ba
Commercial

1192 & 1200 Kingston Rd. Road, Pickering

Apr 17, 2026
DOM: 190

Rare land assembly opportunity in a rapidly evolving corridor of Pickering. 1192 & 1200 Kingston Rd ...

MLS#: E13021442
For Sale
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