5295 - 5315 Sideline 16 Road

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.

Details

Type

Rural Residential

Style

1 1/2 Storey

Age

100+ years

Size

3000-3500 sq ft

Lot

1308.4 × 2659.53 ft

Basement

Partial Basement, Unfinished

Garage

Detached

Kitchens

3

Property tax

$9,822 (2026)

Neighbourhood

Rural Pickering

Municipality

Pickering

Interior

Bedrooms

8 above ground

Bathrooms

3 × 4-piece (ground), 2 × 4-piece (second), 1 × 3-piece (ground)

Rooms

21 above ground

Family room or den

Yes

Fireplace

Wood Stove

Features

Brick & Beam, Water Heater Owned

Heating, cooling and services

Heating

Forced Air, Electric

Air conditioning

Wall Unit(s)

Water and sewer

Septic

Building and exterior

Style

1 1/2 Storey

Exterior

Vinyl Siding

Roof

Shingles

Foundation

Stone

Age

100+

Faces

East

Outdoor

Barn, Workshop

Parking

Garage spaces

3

Total parking

9

Driveway and parking

Private

Lot

Size

1308.4 × 2659.53 ft (irregular)

Acreage

50-99.99

More

Possession

90+ days

Nearby

Lake/Pond, Wooded/Treed, River/Stream

Cross street

Concession 9/Brock Road