✨ 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, 5 Bath Home at 1837 New Street Pickering ON listed at $2,798,800 (MLS# E13774984)
Added 5 days ago
$2,798,800
4bd
5ba
Residential Freehold

1837 New Street, Pickering

Sep 11, 2026
DOM: 6

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

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)
Added 13 days ago
$2,599,900
8bd
7ba
Residential Freehold

5050 William Street, Pickering

Sep 3, 2026
DOM: 14

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

MLS#: E13741468
For Sale
Residential Freehold for sale - 7 Bed, 7 Bath Home at 1309 Commerce Street Pickering ON listed at $2,045,000 (MLS# E13736838)
Added 14 days ago
$2,045,000
7bd
7ba
Residential Freehold

1309 Commerce Street, Pickering

Sep 2, 2026
DOM: 15

Don't Miss This Rare Opportunity To Own A Stunning 1-Year-New Custom-Built Luxury Home In One Of Pic...

MLS#: E13736838
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 1488 Rosebank Road Pickering ON listed at $2,180,000 (MLS# E13707836)
$2,180,000
4bd
4ba
Residential Freehold

1488 Rosebank Road, Pickering

Aug 24, 2026
DOM: 24

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
$3,360,000
5bd
7ba
Residential Freehold

5321 Old Brock Road, Pickering

Aug 21, 2026
DOM: 27

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)
$2,999,088
5bd
8ba
Residential Freehold

2342 Heska Road, Pickering

Aug 19, 2026
DOM: 29

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 809 Fairview Avenue Pickering ON listed at $2,098,000 (MLS# E13691804)
$2,098,000
5bd
4ba
Residential Freehold

809 Fairview Avenue, Pickering

Aug 19, 2026
DOM: 29

Absolutely Knock-Out Gorgeous Custom Built Masterpiece Home Featuring Highest Quality Designs And St...

MLS#: E13691804
For Sale
Residential Freehold for sale - 5 Bed, 4 Bath Home at 1472 Highbush Trail Pickering ON listed at $2,849,000 (MLS# E13684770)
$2,849,000
5bd
4ba
Residential Freehold

1472 Highbush Trail, Pickering

Aug 17, 2026
DOM: 31

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

MLS#: E13684770
For Sale
Residential Freehold for sale - 4 Bed, 5 Bath Home at 700 Hillcrest Road Pickering ON listed at $2,399,000 (MLS# E13682038)
$2,399,000
4bd
5ba
Residential Freehold

700 Hillcrest Road, Pickering

Aug 16, 2026
DOM: 32

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

MLS#: E13682038
For Sale
Residential Freehold for sale - 4 Bed, 5 Bath Home at 830 Fairview Avenue Pickering ON listed at $2,175,000 (MLS# E13672572)
Price Change
$2,175,000
4bd
5ba
Residential Freehold

830 Fairview Avenue, Pickering

Aug 13, 2026
DOM: 35

Beautiful 3+1 bedroom, 5-bathroom, Rubinoff Design Group custom-built water view home on Frenchman's...

MLS#: E13672572
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)
$2,800,000
1bd
1ba
Residential Freehold

3315 Hwy 7 Highway, Pickering

Aug 13, 2026
DOM: 35

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

MLS#: E13673826
For Sale
Residential Freehold for sale - 6 Bed, 6 Bath Home at 506 Rougemount Drive Pickering ON listed at $2,599,900 (MLS# E13658730)
$2,599,900
6bd
6ba
Residential Freehold

506 Rougemount Drive, Pickering

Aug 10, 2026
DOM: 38

Welcome home to 506 Rougemount Drive, set on one of Pickering's most coveted streets and backing dir...

MLS#: E13658730
For Sale
Residential Freehold for sale - 5 Bed, 6 Bath Home at 711 Hillview Crescent Pickering ON listed at $2,300,000 (MLS# E13647744)
$2,300,000
5bd
6ba
Residential Freehold

711 Hillview Crescent, Pickering

Aug 6, 2026
DOM: 42

Brand New, Never-Been-Lived In, Gorgeous Custom-Built 3-Storey Dream Home W/ The Highest Quality Des...

MLS#: E13647744
For Sale
Residential Freehold for sale - 7 Bed, 5 Bath Home at 732 W Shore Boulevard Pickering ON listed at $2,900,000 (MLS# E13585324)
$2,900,000
7bd
5ba
Residential Freehold

732 W Shore Boulevard, Pickering

Jul 20, 2026
DOM: 59

Experience refined waterfront community living in this extraordinary over 6000 sq ft of living space...

MLS#: E13585324
For Sale
Residential Freehold for sale - 6 Bed, 7 Bath Home at 432 Sheppard Avenue Pickering ON listed at $2,689,900 (MLS# E13580966)
$2,689,900
6bd
7ba
Residential Freehold

432 Sheppard Avenue, Pickering

Jul 18, 2026
DOM: 61

A landmark custom residence by Zippy Custom Homes, where timeless elegance, exceptional craftsmanshi...

MLS#: E13580966
For Sale
Residential Freehold for sale - 5 Bed, 4 Bath Home at 4395 Westney Road Pickering ON listed at $2,681,000 (MLS# E13560738)
Price Change
$2,681,000
5bd
4ba
Residential Freehold

4395 Westney Road, Pickering

Jul 14, 2026
DOM: 65

Welcome to this A One-of-a-Kind Private Country Estate. This extraordinary modern farmhouse is nestl...

MLS#: E13560738
For Sale
Residential Freehold for sale - 5 Bed, 4 Bath Home at 369 Toynevale Road Pickering ON listed at $2,250,000 (MLS# E13544326)
$2,250,000
5bd
4ba
Residential Freehold

369 Toynevale Road, Pickering

Jul 8, 2026
DOM: 71

Home custom-made in 2015, Urban retreat/mins to Toronto in coveted area/walk to lake & conservation ...

MLS#: E13544326
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)
$3,999,000
6bd
7ba
Residential Freehold

3405 Sideline 4 Road, Pickering

Jul 8, 2026
DOM: 71

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 $5,900,000 (MLS# E13533054)
$5,900,000
7bd
5ba
Residential Freehold

3395 Pickering Uxbridge Townline, Pickering

Jul 7, 2026
DOM: 72

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 - 7 Bed, 6 Bath Home at 901 Wingarden Crescent Pickering ON listed at $2,379,000 (MLS# E13531810)
$2,379,000
7bd
6ba
Residential Freehold

901 Wingarden Crescent, Pickering

Jul 7, 2026
DOM: 72

From the moment you step inside, you'll be impressed by the exceptional craftsmanship, luxurious fin...

MLS#: E13531810
For Sale
Residential Freehold for sale - 4 Bed, 3 Bath Home at 1275 Wharf Street Pickering ON listed at $2,600,000 (MLS# E13500404)
$2,600,000
4bd
3ba
Residential Freehold

1275 Wharf Street, Pickering

Jun 29, 2026
DOM: 80

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

MLS#: E13500404
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
$2,395,000
5bd
5ba
Residential Freehold

752 Hillview Crescent, Pickering

Jun 27, 2026
DOM: 82

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)
$2,500,000
5bd
5ba
Residential Freehold

968 Essa Crescent, Pickering

Jun 26, 2026
DOM: 83

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)
$4,299,900
4bd
1ba
Residential Freehold

2300 Rosebank Road, Pickering

Jun 25, 2026
DOM: 84

Where else can you find a parcel of land this large, this close to the city? A SPECTACULAR almost 15...

MLS#: E13488844
For Sale
Residential Freehold for sale - 5 Bed, 5 Bath Home at 1434 Rougemount Drive Pickering ON listed at $2,250,000 (MLS# E13488010)
$2,250,000
5bd
5ba
Residential Freehold

1434 Rougemount Drive, Pickering

Jun 25, 2026
DOM: 84

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

MLS#: E13488010
For Sale
Residential Freehold for sale - 5 Bed, 5 Bath Home at 3335 Hollywood Court Pickering ON listed at $2,800,000 (MLS# E13485752)
$2,800,000
5bd
5ba
Residential Freehold

3335 Hollywood Court, Pickering

Jun 24, 2026
DOM: 85

Set within the prestigious Barclay Fieldstone Estates enclave, 3335 Hollywood Crt is a rare custom b...

MLS#: E13485752
For Sale
Residential Freehold for sale - 8 Bed, 6 Bath Home at 1879 Appleview Road Pickering ON listed at $2,499,000 (MLS# E13449914)
$2,499,000
8bd
6ba
Residential Freehold

1879 Appleview Road, Pickering

Jun 15, 2026
DOM: 94

Rare opportunity to own a custom-built executive home in Pickering's highly sought-after Dunbarton c...

MLS#: E13449914
For Sale
Residential Freehold for sale - 8 Bed, 5 Bath Home at 5023 Franklin Street Pickering ON listed at $2,640,000 (MLS# E13418042)
$2,640,000
8bd
5ba
Residential Freehold

5023 Franklin Street, Pickering

Jun 8, 2026
DOM: 101

Welcome To 5023 Franklin St, An Extraordinary Custom-Built Bungaloft Estate Nestled In The Prestigio...

MLS#: E13418042
For Sale
Residential Freehold for sale - 6 Bed, 4 Bath Home at 4780 Westney Road Pickering ON listed at $2,395,000 (MLS# E13230918)
$2,395,000
6bd
4ba
Residential Freehold

4780 Westney Road, Pickering

Jun 2, 2026
DOM: 107

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

MLS#: E13230918
For Sale
Residential Freehold for sale - 5 Bed, 6 Bath Home at 1921 Bonita Avenue Pickering ON listed at $3,300,000 (MLS# E13220994)
$3,300,000
5bd
6ba
Residential Freehold

1921 Bonita Avenue, Pickering

Jun 1, 2026
DOM: 108

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

MLS#: E13220994
For Sale
Residential Freehold for sale - 7 Bed, 9 Bath Home at 3325 Hollywood Court Pickering ON listed at $4,995,000 (MLS# E13215550)
$4,995,000
7bd
9ba
Residential Freehold

3325 Hollywood Court, Pickering

May 29, 2026
DOM: 111

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

MLS#: E13215550
For Sale
Residential Freehold for sale - 4 Bed, 4 Bath Home at 1436 Highbush Trail Pickering ON listed at $2,250,000 (MLS# E13214954)
$2,250,000
4bd
4ba
Residential Freehold

1436 Highbush Trail, Pickering

May 29, 2026
DOM: 111

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

MLS#: E13214954
For Sale
Residential Freehold for sale - 7 Bed, 7 Bath Home at 1427 Rosebank Road Pickering ON listed at $2,649,000 (MLS# E13170706)
$2,649,000
7bd
7ba
Residential Freehold

1427 Rosebank Road, Pickering

May 25, 2026
DOM: 115

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

MLS#: E13170706
For Sale
Residential Freehold for sale - 7 Bed, 6 Bath Home at 1411 Old Forest Road Pickering ON listed at $3,000,000 (MLS# E13169162)
Price Change
$3,000,000
7bd
6ba
Residential Freehold

1411 Old Forest Road, Pickering

May 25, 2026
DOM: 115

Welcome to The Bridge House - Where Family Stays Connected. A thoughtfully designed generational est...

MLS#: E13169162
For Sale
Commercial for sale - 0 Bed, 0 Bath Home at 755 OKLAHOMA Drive Pickering ON listed at $5,500,000 (MLS# E13152226)
$5,500,000
0bd
0ba
Commercial

755 OKLAHOMA Drive, Pickering

May 20, 2026
DOM: 120

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

MLS#: E13152226
For Sale
Residential Freehold for sale - 6 Bed, 6 Bath Home at 413 Sheppard Avenue Pickering ON listed at $2,499,000 (MLS# E13149064)
$2,499,000
6bd
6ba
Residential Freehold

413 Sheppard Avenue, Pickering

May 19, 2026
DOM: 121

Welcome To 413 Sheppard Ave Located In Prestigious Woodlands. This Exceptional 4+2 Bedroom, 6 Bathro...

MLS#: E13149064
For Sale
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