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 (1 Days)
$6,948,038 (USD)
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 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 Sep 24 2026 at 9:42 PM EDT
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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