5295 - 5315 Sideline 16 Road, Pickering, ON L1Y 1A1
Rural Pickering, Pickering · Near Concession 9/Brock Road · View map
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.
The home
- Type
- 1 1/2 storey
- Style
- 1 1/2 Storey
- Square footage
- 3000-3500 sq ft
- Bedrooms
- 8
- Bathrooms
- 6
- Kitchens
- 3
- Rooms
- 21
- Basement
- Partial Basement, Unfinished
- Lot size
- 1308.4 x 2659.5 ft
- Faces
- East
- Approximate age
- 100+ years
Ownership & fees
- Ownership
- Freehold
- Monthly condo fee
- None
- Exterior
- Vinyl Siding
Heating & cooling
- Heating fuel
- Electric
- Heating type
- Forced Air
- Air conditioning
- Wall Unit(s)
- Fireplace
- Yes
Garage & parking
- Garage
- Detached
- Garage spaces
- 3
- Driveway spaces
- 6
- Total parking
- 9
- Parking features
- Private
Taxes & other
- Property taxes
- $9,822/yr
- Tax year
- 2026
- Occupancy
- Owner
- Possession
- 90+ days
- Cross street
- Concession 9/Brock Road
- Neighbourhood
- Rural Pickering
More
- Price per sq ft
- ~$3,015 (at 3,250 sq ft)
- Listed
- Sep 23, 2026 · 20 days ago
- MLS® number
- E13819414
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The home and its surroundings
- Brick & Beam
- Water Heater Owned
- Lake/Pond
- Wooded/Treed
- River/Stream
- Mortgage
- Property tax
- Maintenance fee
Cash needed to close
Estimates only, using Canadian semi-annual compounding, Ontario land transfer tax. Mortgage default insurance is added when you put down less than 20%. Your lender and lawyer will confirm exact numbers.
5295 - 5315 Sideline 16 Road, Pickering, ON L1Y 1A1
Rural Pickering, Pickering · Near Concession 9/Brock Road
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Listing history for 5295 - 5315 Sideline 16 Road
See what this home and others at the same address were listed for, what they sold for, and how long it took.
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Frequently asked questions about 5295 - 5315 Sideline 16 Road
Answers come straight from this home’s MLS® listing.
How much is 5295 - 5315 Sideline 16 Road listed for, and what would it cost each month?
5295 - 5315 Sideline 16 Road is listed for $9,800,000. With 20% down ($1,960,000), the mortgage payment would be roughly $39,530 a month at 4.5% over 30 years. Add property tax and the estimate comes to about $40,349 a month, all in. That figure is an illustration, not a quote.
Is 5295 - 5315 Sideline 16 Road freehold or a condo, and is there a monthly fee?
5295 - 5315 Sideline 16 Road is a 1 1/2 storey in Rural Pickering, Pickering. Ownership is freehold: you own the home and the lot. There is no monthly condo fee, so the roof, windows, driveway, snow and lawn are yours to look after.
How many bedrooms and bathrooms does 5295 - 5315 Sideline 16 Road have?
5295 - 5315 Sideline 16 Road has 8 bedrooms and 6 bathrooms.
Does 5295 - 5315 Sideline 16 Road have a garage and parking?
Yes. The listing shows the garage as detached, with room for 3 cars. The driveway adds 6 spaces. In total the listing counts 9 parking spaces.
Does 5295 - 5315 Sideline 16 Road have a finished basement?
The listing describes the basement as partial basement, unfinished.
What style of home is 5295 - 5315 Sideline 16 Road?
5295 - 5315 Sideline 16 Road is a 1 1/2 storey. A 1½-storey home has a full main floor and a partial second floor under the roofline, often with dormer windows.
How big is 5295 - 5315 Sideline 16 Road, and what is the lot size?
The listing puts the home between 3,000 and 3,500 sq ft. The board reports a range rather than an exact figure, and it usually leaves out the basement. The lot is listed as 1308.4 x 2659.5 ft.
How is 5295 - 5315 Sideline 16 Road heated and cooled?
Heating is forced air (electric). Cooling is wall unit(s).
What are the property taxes for 5295 - 5315 Sideline 16 Road?
Property taxes are $9,822 a year (2026), or about $819 a month.
Where is 5295 - 5315 Sideline 16 Road?
5295 - 5315 Sideline 16 Road is in the Rural Pickering community of Pickering. The nearest main intersection is Concession 9/Brock Road. The postal code is L1Y 1A1.
How long has 5295 - 5315 Sideline 16 Road been on the market?
5295 - 5315 Sideline 16 Road was listed on September 23, 2026. It has been on the market for 20 days. It is an active listing (MLS® E13819414). Listings here update from the board through the day and come down once a home sells.
What have homes at 5295 - 5315 Sideline 16 Road sold for?
Recent sales, leases and expired listings for this home and others at the same address are in the Sold history tab, with the price and date of each. It is free for members.
How do I book a showing at 5295 - 5315 Sideline 16 Road?
Pick a day and time with Book a Tour on this page. Tours are free, with no obligation, in person or by video. You can also call or text 647-619-2256.
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Courtesy of: CENTURY 21 WENDA ALLEN REALTY
PropTx MLS® assumes no responsibility for the accuracy of any information shown. The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale or lease of real estate and may not be used for any commercial purpose or any other purpose.
*Estimated monthly cost assumes 20% down, a 4.5% rate and a 30-year amortization, plus property tax. For illustration only.