The Jennifer Jones Team, LPT Realty, Brokerage
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Pickering, ON

5295 - 5315 Sideline 16 Road

$9,800,000

Data last updated Oct 30, 2026, 2:50 a.m. ET. By using this site you agree to our Terms of Use.

rural residential at 5295 - 5315 Sideline 16 Road, Pickering, ON
5295 - 5315 Sideline 16 Road, Pickering, ON, photo 25295 - 5315 Sideline 16 Road, Pickering, ON, photo 3

Property facts

Price
$9,800,000
Type
rural residential
Bedrooms
8
Bathrooms
6
MLS®
E13819414
Status
active
Brokerage
CENTURY 21 WENDA ALLEN REALTY

About this home

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.

Location

Search the full MLS®

More details

Property tax
$9,822 (2026)
Days on market
38
Style
1 1/2 Storey
Year built
100+
Lot
1308.4 × 2659.53 Feet
Parking
9 spaces · 3 garage · Detached
Basement
Partial Basement, Unfinished
Heating
Forced Air
Air conditioning
Wall Unit(s)
Neighbourhood
Rural Pickering
Major intersection
Concession 9/Brock Road

Details from PropTx (TRREB MLS®) via Repliers. Information deemed reliable but not guaranteed.

Home value