5295 - 5315 Sideline 16 Road, Pickering
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. (id:1945)
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Property details for 5295 - 5315 Sideline 16 Road, Pickering
- Type
- Residential
- Bedrooms
- 8
- Bathrooms
- 6
- Lot Size
- 1308.4 x 2659.5 FT
- Stories
- 1.5
- Basement
- Unfinished, Partial
- Parking
- Detached Garage, Garage
- Heating
- Forced air, Electric
- Cooling
- Wall unit
- Exterior
- Vinyl siding
- Annual Taxes
- $9,822
Nearby Listings Stat
Estimated price and comparable properties near 5295 - 5315 Sideline 16 Road
Active Listings
1
Min Price
$9,800,000
Max Price
$9,800,000
Avg Price
$9,800,000
Days on Market
0
days
Sold Listings
0
Min Sold Price
$N/A
Max Sold Price
$N/A
Avg Sold Price
$N/A
Days until Sold
N/A
days
Neighbourhood Census Data
Pickering, Ontario
Population
443
Median Age
44.2
Median Income
$44,416
Dwelling Value
$650,051
Housing Tenure
Owners 79%
Renters 18%
Age Distribution
Dwelling Types
Commute Mode
Education Level
Housing Age
Commute Duration
Avg Household Size: 2.7
Pop. Density: 70.3/km²
Avg Shelter Cost: $1,852/mo
Owners with Mortgage: 65.4%
Owners Spending 30%+: 19.2%
Tenants Spending 30%+: 0%
English only: 93.3%
English and French: 6.7%
Median Household Income: $117,504
Median Employment Income: $38,144
Price History
Listed
September 23, 2026
by CENTURY 21 WENDA ALLEN REALTY
Current Price
$9,800,000
Type
Residential
For Sale
Contact Agent Get in touch about 5295 - 5315 Sideline 16 Road, Pickering
JOHN P O'LEARY
CENTURY 21 WENDA ALLEN REALTY