$9,800,000
105.20 BTC
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5295 - 5315 Sideline 16 Road, Pickering
$9,800,000
PRICE
8
BEDROOMS
6
BATHROOMS
E13819414
MLSID

5295 - 5315 Sideline 16 Road, Pickering

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.
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Summary

Address
5295 - 5315 Sideline 16 Road
MLSID
E13819414
Property Type
Rural Residential
Property Category
Bedrooms
8
Bathrooms
6
Kitchens
3
Taxes (Annual)
$9,822.38
Tax Year
2026
Published
September 23, 2026
Days on Market
0 Days
Possession Type
90+ Days
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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.

Exclusions

Kubota farm tractor and all attachments, 3 riding lawn mowers and attachments, recreational vehicles and attachments.

Details

Property Features
Lake/Pond, Wooded/Treed, River/Stream
Bathroom 1
4-Piece Ground Level
Bathroom 2
4-Piece Second Level
Bathroom 3
3-Piece Ground Level
Basement
Partial Basement, Unfinished
Interior Features
Brick & Beam, Water Heater Owned
Parking Spaces
6
Parking Total
9
Parking Features
Private
Architectural Style
1 1/2 Storey
Roof
Shingles
Construction Materials
Vinyl Siding
Lot Size
2,264,509 SquareFeet
Lot Width
1,308 Feet
Lot Depth
2,660 Feet
Water
Well
Heat Source
Electric
Heat Type
Forced Air
New Construction
No
Occupant Type
Owner
Private Entrance
No
Sauna
No
Seasonal Property
No
Hot Tub / Spa
No
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