5295 - 5315 Sideline 16 Road, Pickering
1 / 50
For Sale
$9,800,000
8 bd · 6 ba · 3,000–3,500 sq ft

5295 - 5315 Sideline 16 Road, Pickering L1Y 1A1

MLS®# E13819414

Est. mortgage
$37,178/mo
Property taxes $9,822.38/yr

About This Home

Property Type
House, Rural Resid, 1 1/2 Storey
Parking
Detached 3 garage, 6 parking
MLS #
E13819414
Size
3000-3500 sqft
Basement
Partial Basement,Unfinished
Listed on
2026-09-23
Lot size
1308 x 2659.53
Tax
$9,822.38 /yr
Days on Market
51
Approximate Age
100+
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 located on a dead-end road for ultimate privacy and only 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 Details

Full Property Details

Interior

Bedrooms
8
Total Bedrooms
8
Washrooms
6
Square Footage
3000-3500 sqft
Basement
Partial Basement,Unfinished
Heating Source
Electric
Heating Fuel
Forced Air
Air Conditioning
Wall Unit
Family Room
Yes
Kitchens
3
Total Kitchens
3
Fireplace Features
Yes

Exterior

Depth
2659.53
Front
1308.4
Acreage
50-99.99
Driveway
Private
Lot Size
1308 x 2659.53 ft
Pool
None
Waterfront
None
Parking Spaces
6
Total Parking Spaces
9.00
Parking Description
Detached
Garage Spaces
3

Building Description

Style
1 1/2 Storey
Home Type
House
Subtype
Rural Resid
Year Built
100+
Property Orientation
East
Exterior Finish
Vinyl Siding
Sewers
Septic
Water Supply
Well
Possession Date
3/31/2027

Community

Community
Rural Pickering

Taxes & Fees

Taxes
$9,822.38 /yr
Tax Year
2026
Occupancy
Owner

Other

Virtual Tour Link
Adrian Gennuso
Adrian Gennuso
Keller Williams Energy Real Estate
51 days on site
Listing Broker
CENTURY 21 WENDA ALLEN REALTY
Courtesy
CENTURY 21 WENDA ALLEN REALTY
Listed Date
9/23/2026

Courtesy of PropTx MLS® / CENTURY 21 WENDA ALLEN REALTY

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