5295 - 5315 Sideline 16 Road
Pickering (Rural Pickering), ON L1Y 1A1
- 8Bedrooms
- 6Bathrooms
- 3Garage
- 3000–3500Sq Ft
- $9,822Tax
- 1,308×2,660 ftLot Size
Free EstimateSee Free Estimate Report
Sale & Price History for 5295 - 5315 Sideline 16 Road, Pickering, Rural Pickering
| Start Date | End Date | Price | Event | MLS# |
|---|---|---|---|---|
| No listing history available | ||||
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About 5295 - 5315 Sideline 16 Road, Pickering, Rural Pickering
Summarized Description
- Unique estate on over 50 acres of land
- Features a private bass fishing pond
- Includes groomed walking trails for recreation
- Three homes with a total of 8 bedrooms
- Impressive 100 ft. bridge with gazebo
- Custom-built gazebo for serene enjoyment
- Located near Uxbridge, Stouffville, and Pickering
- Meticulously maintained for over 34 years
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.
Key Facts & Features
Property Costs
- Annual Property Tax Amount
- $9,822
- Land Transfer Tax Fee
- $231,475
Rental Items
- Rental Equipment
- HWT, Iron Blaster, Water Filter System at 5305 Sideline 16 --- HWT at 5315 Sideline 16
- Basement Type
- Partial Basement, Unfinished
Interior Features
- Laundry Level
- Main Level
- Interior Extras
- Brick & Beam, Water Heater Owned
- Fireplace/Stove
- Yes
- Fireplace Features
- Wood Stove
- Elevator
- No
Exterior Features
- Pool
- None
- Property Features
- Lake/Pond, Wooded/Treed, River/Stream
- Other Structures
- Barn, Workshop
Building
- Building Type
- Rural Residential
- Building Style
- 1 1/2 Storey
- Approx Age
- 100+
Construction
- Exterior Finish
- Vinyl Siding
- Roof
- Shingles
- Foundation Details
- Stone
- Special Designation
- Unknown
Lot
- Lot Front
- 1308.40 ft
- Lot Depth
- 2659.53 ft
- Lot Size
- 2264509
- Lot Shape
- Irregular
Inclusions
- 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
- Exclusions
- Kubota farm tractor and all attachments, 3 riding lawn mowers and attachments, recreational vehicles and attachments.
Parking & Garages
- Garage Type
- Detached
- Garage Spaces
- 3
- Parking Spaces
- 6
- Total Garage And Parking Spaces
- 9
Heating & Cooling
- Heat Source
- Electric
- Heat Type
- Forced Air
- Air Conditioning
- Wall Unit(s)
- Water
- Well
- Sewers
- Septic
- Natural Gas
- No
- Hydro
- Yes
- Cable
- No
- Telephone
- Available
- Bedrooms
- 8
- Washrooms
- 6
- Kitchens
- 3
- Family / bonus room
- Yes
Washrooms
- 4-piece, Ground
- 4-piece, Second
- 3-piece, Ground
- Municipality
- Pickering
- Neighbourhood
- Rural Pickering
- Main cross streets
- Concession 9/Brock Road
- Directions
- Brock Rd. North of 407, Turn Right On Concession 9, First Left Is Sideline 16. Follow To End Of Road
- Waterfront
- None
- MLS® number
- E13819414
- Data source
- Toronto Regional Real Estate Board
- Listed on
- 2026-09-23
- Updated on
- 2026-09-23
- Days on market
- 22 days
- Possession date
- 2027-03-31
- Possession type
- 90+ days
- Co-op commission
- 2.5%
- Seller
- Listed by
- CENTURY 21 WENDA ALLEN REALTY
Home Market Value
Current home valuation for 5295 - 5315 Sideline 16 Road, Pickering, Rural Pickering, Pickering, ON. Listed for $9,800,000
HOMEH Estimate
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Estimated Sales Range
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HOMEH Estimate for 5295 - 5315 Sideline 16 Road, Pickering, Rural Pickering
Calculated with a real agent's CMA method — 45+ years of experience, codified. Not an AI guess.
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Mortgage Payment Calculator
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$1,960,000
| Scenario 1 | Scenario 2 | Scenario 3 | Scenario 4 | |
|---|---|---|---|---|
−Down payment | % $ | % $ | % $ | % $ |
+CMHC insurance | $0 | $0 | $0 | $0 |
=Total mortgage | $7,840,000 | $7,350,000 | $6,860,000 | $6,370,000 |
Amortization | ||||
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| Payment frequency | ||||
=Mortgage payment | $38,279monthly | $35,886monthly | $33,494monthly | $31,102monthly |
Land Transfer Tax
$231,475
$231,475
Around this home
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