5295 - 5315 Sideline 16 Road, Pickering
1 / 50
For Sale
$9,800,000
0 bd · 3 ba

5295 - 5315 Sideline 16 Road, Pickering L1Y 1A1

MLS®# E13823118

Est. mortgage
$37,178/mo
Property taxes $9,822.38/yr

About This Home

Property Type
Commercial, Investment
Parking
Other
MLS #
E13823118
Listed on
2026-09-24
Lot size
1308 x 2659.53
Tax
$9,822.38 /yr
Days on Market
50
Approximate Age
100+
Welcome to Happy Valley Estate featuring 3 beautiful homes on 50+ acres that is breathtaking with its unmatchable rolling hills scenery and privacy. This "one-of-a-kind" property is an unparalleled estate that has been meticulously maintained and enjoyed for over 34 years. This impressive estate offers 3+acre bass fishing pond, 2+ km of groomed walking trails, 3 over-sized garages, large nautical themed party room, huge 2-story barn, unlimited wildlife plus a 100 ft. bridge crossing the pond with gazebo where you can sit and ponder the majestic beauty of it all. It is a retreat of timeless elegance once owned by the famous "Kortright" family of the Kortright Conservation Centre. This amazing property is 10 minutes north of Hwy. 407 and is centrally located between Uxbridge, Stouffville and Pickering. The 3 homes have a total of 8 bedrooms, 3 kitchens and 6 bathrooms. #5295 -1st home is approx. 3,000sq.ft. century style timeless masterpiece located upon the hill overlooking the pond. This home boasts vaulted ceilings, original homestead beams, massive stone fireplace, 3-car garage, walkout to cozy porch, 3 bdrms. huge 2-story 62' barn. #5305 - 2nd home is a beautiful spacious bungalow approx. 2000sq.ft. situated at the water's edge. This home boasts rare hand-cut fieldstone fireplace, floor-to-ceiling windows to maximize the water and nature view from inside or from the huge wrap around deck. There are 2 Bdrms., 4-season sunroom w/walkout and a 2-car detached garage w/huge party room above it. #5315 - 3rd home is approx. 1850sq.ft. 1-1/2 story nestled back in the towering mature trees featuring stunning custom-built 23' x 23' gazebo for enjoying the serenity and privacy. This home boasts cathedral ceilings, shiplap accent-wall, cozy woodburning stove, quartz counter tops, 3 bdrms, attached 2-car garage & single car garage w/tandem style carport.

Property Details

Full Property Details

General

Business Type
-
Total Area
50.25 Acres
Sprinklers
-
Drive-In Level Shipping Doors
-
Double Man Shipping Doors
-
Grade Level Shipping Doors
-
Truck Level Shipping Doors
-

Interior

Washrooms
3
Heating Source
Electric
Heating Fuel
Elec Forced Air
Air Conditioning
Yes

Exterior

Depth
2659.53
Front
1308.4
Lot Size
1308 x 2659.53 ft
Parking Spaces
-
Total Parking Spaces
-
Parking Description
Other
Garage Spaces
-
Zoning
ORM-EP

Building Description

Home Type
Commercial
Subtype
Investment
Year Built
100+
Sewers
Septic
Water Supply
Well
Possession Date
3/31/2027

Community

Community
Rural Pickering

Taxes & Fees

Taxes
$9,822.38 /yr
Tax Year
2026
Occupancy
Owner

Other

Virtual Tour Link
Adrian Gennuso
Adrian Gennuso
Keller Williams Energy Real Estate
50 days on site
Listing Broker
CENTURY 21 WENDA ALLEN REALTY
Courtesy
CENTURY 21 WENDA ALLEN REALTY
Listed Date
9/24/2026

Courtesy of PropTx MLS® / CENTURY 21 WENDA ALLEN REALTY

Similar homes for sale in Pickering

Explore Pickering

Copyright 2026 All rights reserved. Toronto Regional Real Estate Board (TRREB) assumes no responsibility for the accuracy of any information shown. The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale or lease of real estate and may not be used for any commercial purpose or any other purpose.
Powered by AgentLocator