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    5295 - 5315 Sideline 16 Road

    Pickering, ON • L1Y 1A1
    Rural Residential
    Active
    View on Map
    List Price$9,800,000
    5295 - 5315 Sideline 16 Road
    Pickering, ON • L1Y 1A1
    View on Map
    Rural Residential
    Active
    List Price$9,800,000
    8Beds
    6Baths
    3000-3500 SqFtLiving Area
    9Parking

    Property History

    Market activity for 5295 - 5315 Sideline 16 Road

    0 Records

    No listing history available

    This is the first time this property is listed

    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.

    Listing Snapshot
    Property Type
    Rural Residential
    Size
    3000-3500 SqFt
    Building Age
    100+ years
    Lot Size
    1308.4 x 2659.53 Feet
    Parking
    9 Spaces
    Basement
    Partial Basement, Unfinished
    Property Tax
    $9,822 / 2026
    Added to PropertyMesh
    2026-09-23
    Days on Site
    24 Days
    Status Change
    23 Days Ago
    Listing #
    E13819414
    Listing Brokerage
    CENTURY 21 WENDA ALLEN REALTY
    Data Source
    PROPTX
    Updated on
    2026-09-23
    Property Specifications

    Property Overview

    Property TypeRural Residential
    Style1 1/2 Storey

    Interior Details

    Bedrooms8
    Bathrooms6
    Bathrooms Detail (Ground)3
    Bathrooms Detail (Second)2
    Bathrooms Detail (Ground)1
    Basement TypePartial Basement, Unfinished
    Kitchens3
    Family RoomYes

    Utilities & Systems

    WaterDug Well
    CoolingWall Unit(s)
    Heating FuelElectric
    ElectricityYes
    CableNo

    Building & Construction

    Building Age100+
    ConstructionVinyl Siding

    Parking & Access

    Parking PlacesPrivate
    Total Parking Space9

    Lot & Location

    SewerSeptic
    Frontage1308.4 Feet
    Depth2659.53 Feet
    Lot Size2,264,509 SquareFeet
    Cross StreetConcession 9/Brock Road
    Room Details

    Living Room

    18 x 14 Feet

    Level: Main

    Hardwood Floor, Pot Lights, Combined w/Dining

    Kitchen

    12 x 10 Feet

    Level: Main

    Centre Island, B/I Appliances, Quartz Counter

    Primary Bedroom

    15 x 13 Feet

    Level: Upper

    5 Pc Ensuite, Walk-In Closet(s), Coffered Ceiling(s)

    Bedroom 2

    12 x 11 Feet

    Level: Upper

    3 Pc Bath, Pot Lights, Walk-In Closet(s)

    Bedroom 3

    11 x 10 Feet

    Level: Upper

    Pot Lights, Hardwood Floor

    Land Transfer Tax

    Provincial Tax (Ontario)

    $231,475

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