For Sale MLS® E13819414

5295 - 5315 Sideline 16 Road

Rural Pickering · Pickering · ON · L1Y 1A1

On market 15 days

8 Beds
6 Baths
3,000–3,500 Sqft
9 Parking
Detached Type
100+ Age

About this property

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.

Key facts

Type Rural Residential · 1 1/2 Storey
Size 3,000–3,500 sqft
Lot 1308.4 ft frontage
Age 100+
Taxes $9,822/yr
Basement Partial Basement, Unfinished
Total parking 9
Neighbourhood Rural Pickering
Property details
Property type Rural Residential
Style 1 1/2 Storey
Age 100+
Rooms & baths
Bedrooms above / below 8
Building & utilities
Basement Partial Basement, Unfinished
Parking
Total 9
Lot
Width / Depth 1308.4 ft
Financial
Taxes $9,822/yr

Mortgage calculator

$45,786/moMonthly payment
$7,840,000Mortgage amount
$5,895,858Total interest
$15,695,858Total cost

Location

Street view Street view of the block Look around

Imagery ©Google

Market Overview

Pickering

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MLS® E13819414 Brokerage CENTURY 21 WENDA ALLEN REALTY Listed Sep 23, 2026 Updated Sep 23, 2026

Listing data provided by the Toronto Regional Real Estate Board (TRREB).

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The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing data is deemed reliable but is not guaranteed accurate by TRREB. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA.

Last updated: October 8, 2026.

$9,800,000 8 bd · 6 ba
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