5295 – 5315 Sideline 16 Road, Pickering, ON L1Y 1A1
  • $9,800,000

Overview

  • Rural Residential, Style 1 1/2 Storey
  • Type
  • 8
  • Bedrooms

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.

  • Address: Sideline 16
  • City: Pickering
  • State/county: Durham
  • Zip/Postal Code: L1Y 1A1
  • Area: Rural Pickering

Details

Updated on September 29, 2026 at 5:27 pm
  • Price $9,800,000
  • Bedrooms 8
  • Type Rural Residential, Style 1 1/2 Storey
  • Property Status Residential Freehold

Additional details

  • Square Footage 3000-3500
  • Approximate Age 100+
  • Bedrooms 8
  • Kitchens 3
  • Total Kitchens 3
  • Family Room 1
  • Heating Source Electric
  • Heating Fuel Forced Air
  • Air Conditioning Wall Unit(s)
  • Front 1308.4
  • Depth 2659.53
  • Driveway Private
  • Parking Description Detached
  • Parking Spaces 6
  • Total Parking Spaces 9
  • Pool None
  • Exterior Finish Vinyl Siding
  • Property Orientation East
  • Sewers Septic
  • Waterfront None
  • Cross Street Concession 9/Brock Road
  • Taxes 9822.38
  • Tax Year 2026
  • Occupancy Owner
  • Courtesy of CENTURY 21 WENDA ALLEN REALTY

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