5295 - 5315 Sideline 16 Rd, Pickering, Ontario, L1Y 1A1





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.
Home Details
List Date
2026-09-23
Style
1 1/2 Storey
Type
Rural Resid
Status
Active
Year Built
100+
Features
Bedrooms
8
Bathrooms
6
Heating
Forced Air
Cooling
-
Parking
9 Spaces
Appliances & Equipment
Inclusions
All Elf's and ceiling fans, all window blinds and draperies, 3 Fridges, 3 stoves, 3 dishwashers, 3 range hoods, 1 B/I Microwave, 3 Washers and 3 Dryers. Appliances are stainless steel with the exception of 3 washers and 3 dryers. All appliances are included in as is condition but are presently working perfect. Row boat in pond, oscillator for pond, above ground pool and equipment at 5305 Sideline 16, and all permanent fixtures now on the property.
Exterior
Construction
Vinyl Siding
Water & Sewer
Municipal
Lot Size
1308.4 x 2659.53 Feet
Garage
Detached
Taxes
$10K (2026)
Listing Brokerage
Brokerage Name
CENTURY 21 WENDA ALLEN REALTY

Samuel Muttiah
Transition Realtor | Canada to Southern California
KW Beverly Hills
Share This Listing
Let's Talk About Your Next Move
Whether you are purchasing your home in Southern California, selling property in Canada, or planning a full cross-border transition, Samuel is here to guide you every step of the way.
Cross-Border Relocation Expertise
Every submission is reviewed personally by Samuel Muttiah. He will connect with you directly to evaluate your specific goals, legal logistics, and timeline.
