5295 - 5315 Sideline 16 Road

ActivePickering · Rural Pickering16 days on marketMLS® E13819414

$9,800,000

$3,267 / sq ft

Bedrooms8

Bathrooms6

Interior3,000 sq ft

Lot Size2,264,509 sq ft

TypeSingle Family Home

ListingFor Sale

Days on Market16

About this property

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.

Features & finishes

View

Fireplace

Air Conditioning

Basement

Property details

MLS® Number	E13819414
Status	Active
Listing Type	For Sale
Property Type	Single Family Home
Interior Size	3,000 sq ft
Lot Size	2,264,509 sq ft
Beds / Baths	8 bed · 6 bath
Property Taxes (2026)	$9,822
Neighbourhood	Rural Pickering
City	Pickering
Postal Code	L1Y 1A1
Province	ON
Listed Date	September 23, 2026
Days on Market	16
Price per Sq Ft	$3,267
Brokerage	CENTURY 21 WENDA ALLEN REALTY