Advantage Group Real Estate
5295 - 5315 Sideline 16 Road • Pickering, ON photo 1
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$9,800,000
5295 - 5315 Sideline 16 Road • Pickering, ONNew
Courtesy of CENTURY 21 WENDA ALLEN REALTY
8
Bedrooms
6
Bathrooms
3000-3500
Square feet
9
Parking

About this home

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 located on a dead-end road for ultimate privacy and only 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

Property type
Rural Residential
Style
1 1/2 Storey
Approx. age (yrs)
100+
Total rooms
21
Lot size
1308.4 × 2659.53 ft
Property taxes
$9,822.38 (2026)
Days on market
39
Status
Active
MLS®

Property history

Recently sold nearby

Listing data last updated: Oct 31, 2026, 10:50 a.m. EDT via TRREB IDX.

First listed: Sep 23, 2026, 12:23 p.m. EDT.