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$9,800,000
Ontario,Pickering
For Sale Active
5295 - 5315 SIDELINE 16 ROAD, Pickering, Ontario L1Y1A1
  • 8
  • 3
  • 50 Acre
Basic Details
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. (id:62650)

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Basic Details
  • Property Type: Commercial Sale
  • Listing Type: For Sale
  • Listing ID: E13823118
  • Price: $9,800,000
  • Bedrooms: 8
  • Bathrooms: 3
  • Square Footage: 50 Acre
  • Status: Active
  • Office Name: CENTURY 21 WENDA ALLEN REALTY
  • Property Sub Type: Business
  • Office Key: 50583
Features & Appliances
Features
  • Heating System: Forced air
  • Cooling System: Fully air conditioned
  • Parking: Other
  • Sewer: Septic System
Address Map
  • Location: CA, Ontario, Pickering, L1Y1A1
  • Street: Sideline 16
  • Street Suffix: Road
  • Longitude: W80° 52' 37.7''
  • Latitude: N43° 58' 46.7''
Additional Information
  • Water Source:
  • Lot Features:
  • Lot Size Dimensions: 2264509
Financial
  • Tax Annual Amount: 9822.38
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Listing updated: 2026-09-29 22:31:44
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Listing Information
  • List Agent Key: 1409717
  • List Office Key: 50583
  • Modification Timestamp: 2026-09-24T15:10:17Z
  • Originating System Name: Toronto Regional Real Estate Board
  • Status Change Timestamp: 2026-09-24T15:02:32Z
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Listing updated: 2026-09-29 22:31:44
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