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5295 - 5315 SIDELINE 16 ROAD, Pickering — listed at $9,800,000. Earn buyer cashback at closing. No catches, just more money in your pocket.
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. (id:60164)
What's the parking situation?+
This property includes 9 spaces — Detached Garage, Garage.
What makes this a luxury property?+
At $9,800,000, standout features include 6 bathrooms, 1 fireplace. In this price range, expect higher-end finishes — verify during a showing.
Is 5295 - 5315 SIDELINE 16 ROAD a good fit for a growing family?+
With 8 bedrooms and 6 bathrooms, there's room for kids plus a guest room or home office. The 1.5-storey layout keeps living and sleeping areas separated.
How many fireplaces are there, and what type?+
This home has 1 fireplace. Confirm the fuel type (wood, gas, or electric) and have it inspected — especially wood-burning, which needs a WETT certification for insurance.
What are the ongoing costs beyond the mortgage?+
Budget for annual property taxes of $9,822.38, heating is forced air, electric. Always verify the latest figures with your agent before making an offer — these change yearly.
Does it have a basement, and is it finished?+
Yes — Unfinished, Partial. A finished basement adds meaningful living space beyond the listed square footage.
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