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5295 - 5315 Sideline 16 Rd, Pickering, Ontario, L1Y 1A1

$9.80M
Beds 8Baths 6Sqft 3000-3500Parking 9
5295 - 5315 Sideline 16 Rd Photo 1

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.

Home Details

List Date

2026-09-23

Style

1 1/2 Storey

Type

Rural Resid

Status

Active

Year Built

100+

Features

Bedrooms

8

Bathrooms

6

Heating

Forced Air

Cooling

-

Parking

9 Spaces

Appliances & Equipment

Inclusions

All Elf's and ceiling fans, all window blinds and draperies, 3 Fridges, 3 stoves, 3 dishwashers, 3 range hoods, 1 B/I Microwave, 3 Washers and 3 Dryers. Appliances are stainless steel with the exception of 3 washers and 3 dryers. All appliances are included in as is condition but are presently working perfect. Row boat in pond, oscillator for pond, above ground pool and equipment at 5305 Sideline 16, and all permanent fixtures now on the property.

Exterior

Construction

Vinyl Siding

Water & Sewer

Municipal

Lot Size

1308.4 x 2659.53 Feet

Garage

Detached

Taxes

$10K (2026)

Listing Brokerage

Brokerage Name

CENTURY 21 WENDA ALLEN REALTY

RealtHer Group

RealtHer Group

Real Estate Brokers

RE/MAX Metropolis

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