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

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.

• Inside Ontario's Greenbelt plan area — Oak Ridges Moraine Conservation Plan

  Greenbelt policy limits new development — confirm permitted uses before planning a build or severance.

  Source: Ontario GeoHub — Greenbelt Designation · as of Sep 2026

• Inside the Oak Ridges Moraine plan area — Natural Core Area

  Moraine conservation policy constrains development — confirm this parcel's land-use designation.

  Source: Ontario GeoHub — Oak Ridges Moraine Land Use Designation · as of Sep 2026

• 104 m from a rail corridor

  Visit at train times to judge noise and vibration for yourself.

  Source: Ontario Railway Network (ORWN) · as of Sep 2026

Also checked, nothing flagged at this location: flood hazard mapping, conservation-regulated areas, provincially significant wetlands, the Niagara Escarpment plan, areas of natural and scientific interest, hydro transmission corridors.

Screened against public government mapping at this home’s location — simplified boundaries, not a survey, an appraisal or a legal determination. Confirm anything that matters with the authority named.