$9,800,000
5295 - 5315 Sideline 16 Rd
Pickering, ON L1Y 1A1
5295 - 5315 Sideline 16 Rd, Pickering — Listed at $9,800,000. 8 bedroom, 3 bathroom Investment. MLS® E13823118.
Possession · seller's timeline
90+ days
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.
Property Details
Business Details
Property Insights
Listing Courtesy of: CENTURY 21 WENDA ALLEN REALTY
MLS® #E13823118


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HouseIndex Take: 5295 - 5315 Sideline 16 Road
This investment is located in the Rural Pickering neighbourhood of Pickering.
The home offers 8 bedrooms, 3 bathrooms.
Additional details: lot dimensions of 1308.4 × 2659.53 feet.
Listed at $9,800,000 CAD with annual property taxes of $9,822.38 (2026).
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About Pickering Real Estate
This Investment is located in the Rural Pickering community in Pickering. Pickering bridges Toronto's east end and Durham Region, offering relatively affordable homes with direct GO Train connectivity. The Pickering Town Centre area is undergoing major intensification, while established neighbourhoods like Rougemount and Liverpool offer mature streetscapes. Rouge National Urban Park is a unique asset for nature enthusiasts.

















































