5295 - 5315 Sideline 16 Road Pickering, ON L1Y 1A1
Listing Courtesy of: PropTX / Listed By: John O'Leary, Century 21 Wenda Allen Ltd. Brokerage

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

Active (47 Days)
$9,800,000 (CAD)
8
BED
6
BATH
3000-3500
SQFT

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 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.

MLS®:
E13819414
Taxes
$9,822(2026)
Lot Size
51.99 acres
Type
Single-Family Home
Style
1 1/2 Storey
County
Regional Municipality of Durham
Community
Rural Pickering

Listed By

John O'Leary, Century 21 Wenda Allen Ltd. Brokerage
Source
PropTX
Last checked Nov 9 2026 at 4:50 PM EST
Bathroom Details
Interior Features
  • Water Heater Owned
  • Brick & Beam
Property Features
  • Fireplace: Wood Stove
  • Foundation: Stone
Heating and Cooling
  • Forced Air
  • Wall Unit(s)
Basement Information
  • Unfinished
  • Partial Basement
Pool Information
  • None
Exterior Features
  • Vinyl Siding
  • Roof: Shingles
Utility Information
  • Utilities: Well
  • Sewer: Septic
  • Fuel: Electric
  • Energy: Energy Certificate: No
Garage
  • Detached
Parking
  • Private
Stories
  • 2
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