5295 - 5315 Sideline 16 Road, Pickering, ON L1Y 1A1
Rural Pickering · L1Y 1A1
$9,800,000
$4 / sq ft1 months on market
- Bedrooms
- 8
- Bathrooms
- 3
- Total area
- 2,188,890 sf
- Lot
- 1308.4 × 2659.53 ft
- Age
- 100+ years
What's special
- Yes
About this property
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
- Property type
- investment
- Bedrooms
- 8
- Bathrooms
- 3
- Interior size
- 2,188,890 sq ft
- Year built
- 100+
- Lot size
- 1308.4 × 2659.53 ft
- Zoning
- ORM-EP
- Possession
- 90+ days
Interior
- Heating
- Electric Forced Air · Electric
- Cooling
- Yes
Exterior & services
- Garage
- Other
- Water
- Dug Well
- Sewer
- Septic
Costs
- List price
- $9,800,000
- Property taxes
- $9,822 / year (2026)
- Price per sq ft
- $4
- Rental items
- HWT, Iron Blaster, Water Filter System at 5305 Sideline 16 --- HWT at 5315 Sideline 16
Listing
- MLS® number
- E13823118
- Status
- For sale
- Listed
- September 24, 2026
- Days on market
- 42
- Last updated
- September 24, 2026
- Listing brokerage
- CENTURY 21 WENDA ALLEN REALTY
Price & sale history
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Before you make an offer
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Mortgage estimate
- Principal & interest
- $43,348.71
- Property tax (est.)
- $818.53
- Estimated monthly
- $44,167
Estimate only. Excludes CMHC insurance premiums, which apply below 20% down, and does not constitute a mortgage approval or an offer of credit.
Land transfer tax
Payable on closing, on top of the purchase price.
- Ontario
- $231,475
- Total due on closing
- $231,475
An estimate on the asking price of $9,800,000. Rates current as of September 2026; confirm the final figure with your real estate lawyer.
Listing courtesy of CENTURY 21 WENDA ALLEN REALTY. Listing data is provided in part by the Toronto Regional Real Estate Board (TRREB) and is deemed reliable but is not guaranteed accurate. Information is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties. Data is updated every 15 minutes.
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