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5295 - 5315 Sideline 16 Road
Rural Pickering Pickering L1Y 1A1

$9,800,000
Residential Freehold beds: 8 baths: 6.0

Main Photo: 5295 - 5315 Sideline 16 Road in Pickering: Rural Pickering House for sale : MLS®# E13819414
Photo 1: 5295 - 5315 Sideline 16 Road in Pickering: Rural Pickering House for sale : MLS®# E13819414
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Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
E13819414
Bedrooms:
8
Bathrooms:
6
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.
Property Type:
Residential Freehold
Property Sub Type:
Rural Residential
Home Style:
1 1/2 Storey
Approx. Age:
100+
Total Approx Floor Area:
3000-3500
Lot Size:
50-99.99
Lot Depth:
2659'6"
Lot Frontage:
1308'5"
Lot Shape:
Irregular
Direction Faces:
East
Bedrooms:
8
Bathrooms:
6.0
Water supply:
Well
Kitchens:
3
Bedrooms Above Grade:
8
Kitchens Above Grade:
3
Rooms Above Grade:
21
Heating type:
Forced Air
Heating Fuel:
Electric
Fireplaces:
1
Foundation:
Stone
Roof:
Shingles
Basement:
Partial Basement, Unfinished
Fireplace Features:
Wood Stove
Fireplace/Stove:
Yes
Garage:
Detached
Garage Spaces:
3.0
Other Structures:
Barn, Workshop
Parking Features:
Private
Parking Spaces:
6
Total Parking Spaces:
9.0
Family Room:
Yes
Pool:
None
HST Applicable To Sale Price:
In Addition To
Taxes:
$9,822.38 / 2026
Assessment:
$- / -
Durham
Pickering
Rural Pickering
Lake/Pond, Wooded/Treed, River/Stream
Brick & Beam, Water Heater Owned
HWT, Iron Blaster, Water Filter System at 5305 Sideline 16 --- HWT at 5315 Sideline 16
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.
Kubota farm tractor and all attachments, 3 riding lawn mowers and attachments, recreational vehicles and attachments.
Vinyl Siding
None
Utilities Cable:
No
Utilities Telephone:
Available
Utilities Gas:
No
Utilities Hydro:
Yes
Utilities Water:
No
Water Supply Types:
Dug Well
Sewers:
No
Special Designation:
Unknown
Sewers:
Septic
Air Conditioning:
Wall Unit(s)
Central Vacuum:
No
Seller Property Info Statement:
No
Laundry Level:
Main Level
Date Listed:
Sep 23, 2026
Original Price:
Previous Price:
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    5295 Sideline 16 & 3 Car Garage
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    5305 Sideline 16 & Double Garage
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    5315 Sidelin16 & Double Garage
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Listed by CENTURY 21 WENDA ALLEN REALTY
Data was last updated September 25, 2026 at 02:13 PM (UTC)
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