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Investment for sale at 5295 - 5315 Sideline 16 Road, Pickering - 8 bedroom, 3 bathroom - Photo 1 of 50
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Active

$9,800,000

5295 - 5315 Sideline 16 Rd

Pickering, ON L1Y 1A1

5295 - 5315 Sideline 16 Rd, Pickering — Listed at $9,800,000. 8 bedroom, 3 bathroom Investment. MLS® E13823118.

Possession · seller's timeline

90+ days

8Beds
3Baths
Investment
$9,822.38Taxes/yr · 2026

Description

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

Property TypeInvestment
CommunityRural Pickering
Approximate Age100+
Kitchens3
Washrooms3
Lot Size2,264,509 sq ft (51.99 acres)
Lot Dimensions1308.4 × 2659.53 ft
Lot Size Area2,264,509 sqft (GeoWarehouse)
Dir/Cross StConcession 9/Brock Road
Garage TypeOther
Heating TypeElectric Forced Air
Heating SourceElectric
A/CYes
WaterDug Well
SewersSeptic
Taxes (2026)$9,822.38
HSTIn Addition To
Listed Date9/24/2026
Days on Market12 days

Business Details

Property Sub-TypeInvestment
Property UseAccommodation
Occupant TypeOwner
Showing RequirementsList Salesperson
Possession Type90+ days
Listing Expires5/31/2027

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Listing Courtesy of: CENTURY 21 WENDA ALLEN REALTY

MLS® #E13823118

TRREBMLS®

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 REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.

© 2026 Toronto Regional Real Estate Board. All rights reserved.

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HouseIndex Take: 5295 - 5315 Sideline 16 Road

This investment is located in the Rural Pickering neighbourhood of Pickering.

The home offers 8 bedrooms, 3 bathrooms.

Additional details: lot dimensions of 1308.4 × 2659.53 feet.

Listed at $9,800,000 CAD with annual property taxes of $9,822.38 (2026).

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About Pickering Real Estate

This Investment is located in the Rural Pickering community in Pickering. Pickering bridges Toronto's east end and Durham Region, offering relatively affordable homes with direct GO Train connectivity. The Pickering Town Centre area is undergoing major intensification, while established neighbourhoods like Rougemount and Liverpool offer mature streetscapes. Rouge National Urban Park is a unique asset for nature enthusiasts.

Rouge National Urban ParkPickering GO — 35 min to UnionPickering Town Centre intensificationWaterfront & Frenchman's Bay marina
~40 min commute to downtown TorontoWalkability: Moderate near Town Centre — suburban elsewhere
View full Pickering neighbourhood guide →