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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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5295 - 5315 Sideline 16 Road

Rural Pickering / Pickering, ON L1Y 1A1

ActiveFor Sale
8 Beds
3 Baths
50 Sq Ft
2,264,509 Lot Sq Ft
Commercial
Virtual Tour Available

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.

Property Details

StatusActive
Property TypeCommercial
Listing TypeFor Sale
Interior Size50 sq ft
Lot Size2,264,509 sq ft
Bedrooms8
Bathrooms3
Taxes (2026)$9,822
Postal CodeL1Y 1A1
Last UpdatedOct 28, 2026 · 1:21 p.m.

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Features & Amenities

  • Air Conditioning

Buying or selling in Pickering?

Filipe & Isabel Ferreira and the Team Filipe (RE/MAX Ultimate Realty Inc., Brokerage) represent buyers and sellers here. Local guides and live listings below.

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TRREB MLS® Attribution

MLS® E13823118

Listed by CENTURY 21 WENDA ALLEN REALTY

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. The trademarks REALTOR®, REALTORS® and the REALTOR® logo are controlled by CREA and identify real estate professionals who are members of CREA. Listing data provided by the Toronto Regional Real Estate Board (TRREB). The information contained herein is from sources believed to be reliable but is not guaranteed. Information deemed reliable but not guaranteed accurate by TRREB or Team Filipe / RE/MAX.

$9,800,000

asking price

MLS®E13823118
TypeCommercial
CityPickering
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Team Filipe · RE/MAX · (647) 210-6070

Mortgage Estimate

Est. Monthly Payment

$47,855

/month · $7,840,000 mortgage

Down Payment20% — $1,960,000
Interest Rate5.5%

Amortization

Total Interest

$6,516,408

Total Cost

$14,356,408

Estimate only. Based on Canadian semi-annual compounding, 25-yr amortization at 5.5%.

Full Mortgage Calculator →

Listed By

CENTURY 21 WENDA ALLEN REALTY