5295 - 5315 Sideline 16 Road Pickering, Ontario L1Y 1A1
$9,800,000
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. (id:50333)
Property Details
| MLS® Number | E13819414 |
| Property Type | Single Family |
| Community Name | Rural Pickering |
| Equipment Type | Water Heater |
| Features | Wooded Area, Irregular Lot Size, Country Residential |
| Parking Space Total | 9 |
| Rental Equipment Type | Water Heater |
| Structure | Barn, Workshop |
Building
| Bathroom Total | 6 |
| Bedrooms Above Ground | 8 |
| Bedrooms Total | 8 |
| Age | 100+ Years |
| Appliances | Water Heater, All, Blinds, Dishwasher, Dryer, Microwave, Hood Fan, Stove, Washer, Refrigerator |
| Basement Development | Unfinished |
| Basement Type | Partial (unfinished) |
| Cooling Type | Wall Unit |
| Exterior Finish | Vinyl Siding |
| Fireplace Present | Yes |
| Fireplace Total | 1 |
| Fireplace Type | Woodstove |
| Foundation Type | Stone |
| Heating Fuel | Electric |
| Heating Type | Forced Air |
| Stories Total | 2 |
| Size Interior | 3,000 - 3,500 Sqft |
| Type | House |
| Utility Water | Dug Well |
Parking
| Detached Garage | |
| Garage |
Land
| Acreage | Yes |
| Sewer | Septic System |
| Size Depth | 2659 Ft ,6 In |
| Size Frontage | 1308 Ft ,4 In |
| Size Irregular | 1308.4 X 2659.5 Ft |
| Size Total Text | 1308.4 X 2659.5 Ft|50 - 100 Acres |
| Surface Water | Lake/pond |
Utilities
| Electricity | Installed |
https://www.realtor.ca/real-estate/30317650/5295-5315-sideline-16-road-pickering-rural-pickering
Contact Us
Contact us for more information
John P O'leary
Broker
3455 Garrard Road Unit 7
Whitby, Ontario L1R 2N2
(905) 649-3900
(905) 579-1309
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October 31 2026 03:30:00
Toronto Regional Real Estate Board
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