5295 - 5315 Sideline 16 Road
Pickering, ON
- 8 bed
- 6 bath
- approx. 3000-3500 sqft
- Rural Residential
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 located on a dead-end road for ultimate privacy and only 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.
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Listing Details
- Taxes (2026)
- $9,822
- Listed
- September 23, 2026
Price History
Listing history
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Property
- Style
- 1 1/2 Storey
- Age
- 100+
- Construction
- Vinyl Siding
- Roof
- Shingles
- Foundation
- Stone
- Interior
- Brick & Beam, Water Heater Owned
- Lot Size
- 1308.4 x 2659.53 Feet
Parking
- Garage
- Detached
- Covered Spaces
- 3
- Total Parking
- 9
Utilities
- Water
- Dug Well
- Sewer
- Septic
- Heat Source
- Electric
Location & Legal
- Cross Street
- Concession 9/Brock Road
- Parcel Number
- 263920017
- Possession
- 90+ days
- Occupancy
- Owner
Included
- 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.
- Exclusions
- Kubota farm tractor and all attachments, 3 riding lawn mowers and attachments, recreational vehicles and attachments.
- Rental Items
- HWT, Iron Blaster, Water Filter System at 5305 Sideline 16 --- HWT at 5315 Sideline 16
Schools
Elementary
- Claremont Public School1.7 km
Public · Durham DSB · 320 students
Grade 3 reading: 88% met the provincial standard · Grade 6 math: 45% met the provincial standard
Straight-line distance. Nearby schools are not necessarily the assigned schools — confirm catchment with the school board. Scores are EQAO provincial test results for 2024-2025.
Community
Postal area L1Y
- Population
- 1,976
- Private dwellings
- 730
- Median age
- 47.6
- Average household size
- 2.8
- Median household income
- $133,000
Source: Statistics Canada, 2021 Census of Population, catalogue 98-401-X2021013. Adapted from Statistics Canada. This does not constitute an endorsement by Statistics Canada of this product.
Local market
Residential Freehold in Pickering · last 12 months
- Median sold price
- $854,000
- Homes sold
- 1,205
- Median days on market
- 19
- Sale-to-list price
- 99.4%
Based on 1,205 recorded sales of residential freehold properties in Pickering over the last 12 months.
Listed by
CENTURY 21 WENDA ALLEN REALTY
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Location
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Mortgage Calculator
$1,960,000
Estimated Monthly Payment
$48,144
Land transfer tax
Ontario land transfer tax only. An estimate — not legal or financial advice. Municipal land transfer tax applies in Toronto and is not included.
Investment Analysis
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Mortgage: $48,144/mo (20% down, 5.5%)
Taxes: $819/mo · Insurance: $2,450/mo
Estimates only. Consult a financial advisor.
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