$9,800,000
( $4.48Per Sq Foot )
 $52,609 est/mo Sourced by Back At You

5295 - 5315 Sideline 16 Road,Pickering, ON L1Y 1A1

Pickering, ON L1Y 1A1

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Description

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.

Details

MLS #E13823118
Listing TypeFor Sale
Sub-TypeResale
StatusNew
Year0
Days On Site33
Listing Provided ByCENTURY 21 WENDA ALLEN REALTY | E13823118 016200

Features

Bed(s)8
Bath(s)3
SQ Feet2,188,890
Acreage50.25

Interior

CoolingYes
Heat SourceElectric

Utilities

UtilitiesAvailable
SewerSeptic

Taxes

Tax Annual Amount9822.38
Tax TypeAnnual
Tax Legal DescriptionPT NW 1/4 LT 15 & AND PT LT 16 CON 9, PT 1, 40R16208 CITY OF PICKERING
Tax Year2026

Area Information

ProvinceON
CountyDurham
CityPickering
Postal CodeL1Y 1A1
AreaRural Pickering
Listing VS Median (in L1Y 1A1)
Price:
$9,800,000
low | high
Med:
$9,800,000
50% of Average
sqft:
2,188,890
low | high
Med:
2,188,890
50% of Average
$ / sqft:
$4
low | high
Med:
$4
50% of Average
On site:
33
low | high
Med:
33
100% of Average
Sourced by Back At You

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Learn More About This Property

ProvinceON
CountyDurham
CityPickering
Postal CodeL1Y 1A1
AreaRural Pickering
Listing VS Median (in L1Y 1A1)
Price:
$9,800,000
low | high
Med:
$9,800,000
50% of Average
sqft:
2,188,890
low | high
Med:
2,188,890
50% of Average
$ / sqft:
$4
low | high
Med:
$4
50% of Average
On site:
33
low | high
Med:
33
100% of Average
Sourced by Back At You
Listing Updated: September 30, 2026 at 1:04:50 AM PDT