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For SaleRural Resid · 1 1/2 StoreyMLS® #E13819414 · TRREB MLS®

5295 - 5315 Sideline 16 Rd, Pickering, Ontario

Rural Pickering, Pickering, Ontario L1Y 1A1

Bedrooms
8
Lot Size
1,308.4 x 2,659.53 ft
Bathrooms
6
Type
Rural Resid
Basement
Partial Basement

$9,800,000

Estimated market value

About 5295 - 5315 Sideline 16 Rd

5295 - 5315 Sideline 16 Rd is an 8-bedroom, 6-bathroom home in Rural Pickering, Pickering, listed for sale at an asking price of $9,800,000 (MLS® E13819414).

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.

Insights

  • Condition Score

    Good
    68out of 100

    6 condition-related facts documented

    Source: Listing age, structured features and disclosed update language; not an inspection.

Condition uses listing-record signals, not an inspection.

Key facts

Tax
$9,822 / 2026
MLS® number
E13819414
Board
TRREB MLS®
Property Type
Rural Resid
Building Age
100+
Days on market
Size
3000-3500 sqft
Lot Size
1,308.4 x 2,659.53 ft
Listed on
Parking
3 Detached, 9 Parking
Listing brokerage: CENTURY 21 WENDA ALLEN REALTYData source: TRREB MLS®Information deemed reliable but not guaranteed. Contained information is subject to errors, omissions, and changes without notice. Information should be independently verified.

Listing history

Buy/sell history for 5295 - 5315 Sideline 16 Rd, Pickering, Ontario

Sale history on this site covers the last 2 years, the window permitted under the TRREB MLS® VOW agreement.

Dates and closing prices are shown to signed-in members.

Date StartDate EndList PricePriceEventListing ID
Date Start——$9,800,000—For SaleE13819414

Members see the full history. Prices are hidden from signed-out visitors.

Estimate

Estimated value requires sign in

Market estimates use sold comparables and are available after you sign in and accept MLS® VOW terms.

The estimate is an automated value built from public and MLS® data. It is not an appraisal; ask Kishan Patel for a full comparative market analysis.

Property details

Property

Property Type
Rural Resid
Style
1 1/2 Storey
Community
Rural Pickering
Municipality
Pickering

Building

Size
3000-3500 sqft
Building Age
100+
Construction
Vinyl Siding

Inside

Bedrooms
8
Bathrooms
6
Bathroom Details
3 × 4pc Ground, 2 × 4pc 2nd, 1 × 3pc Ground
Basement Type
Partial Basement
Kitchens
3

Parking

Driveway
Private
Garage Type
Detached
Garage
3
Additional Parking
6
Total Parking
9

Utilities

Water
Well
Cooling
Wall Unit
Heating Type
Forced Air

Land

Sewer
Septic
Frontage
1,308.4 ft
Depth
2,659.53 ft
Lot Size
1,308.4 x 2,659.53 ft

Additional

Foundation
Stone
Roof
Shingles
Fireplace
Yes
Pool
None
Den
Yes
Family room
Yes
Extras
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.

Rooms

Room details unavailable

The listing source did not provide room-level measurements or features.

Map and tour

Land transfer tax on this home

Ontario land transfer tax
$231,475
Total land transfer tax
$231,475
First-time buyer rebates (Ontario up to $4,000)
−$4,000
Total for first-time buyers
$227,475
See how this is worked out
0.5% on the first $55,000
$275
1.0% from $55,000 to $250,000
$1,950
1.5% from $250,000 to $400,000
$2,250
2.0% from $400,000 to $2,000,000
$32,000
2.5% from $2,000,000 to $9,800,000
$195,000
Ontario total
$231,475

An estimate at the asking price, for a home with one or two single-family residences. Your lawyer confirms the exact amount.

Land and environment

Public records about this location. Not part of the MLS® listing and not provided by the listing brokerage.

14 records · 9 on fileMatched 2026-11-11
250 m500 m1 km2 kmBeyond · area-wideNot in Toronto and Region Conservation Authority’s mapped regulated areaA mapped wetland is within 120 m1 water-supply well recorded within 250 mGroundwater recorded about 7.2 m below ground nearbyInside the Greenbelt (Oak Ridges Moraine Conservation Plan) and the Oak Ridges Moraine plan area (Natural Core Area)Nearest rail line: 110 mA trail or path within 1 kmNo licensed pit or quarry within 2 kmNo recorded oil, gas or salt well within 250 mNo facility within 1 km reports pollutant releases to Environment CanadaNo federal contaminated site within 1 kmElectricity is distributed here by Elexicon Energy Inc.Wired internet 50/10 Mbps or faster is listed at a household 140 m awayAcross the surrounding area: fibre to the home, cable, DSL internet listed
On record No record found in the source searched

Water and conservation4

  • Not in Toronto and Region Conservation Authority’s mapped regulated areaChecked at the listing’s mapped point, not across the whole lot.At the address
  • A mapped wetland is within 120 mDevelopment close to a wetland can need extra review.120 m
  • 1 water-supply well recorded within 250 mIt was drilled for domestic use. From Ontario’s well records; locations can be approximate. The records do not show how this home gets its water. Wells nearby typically go down about 21 m.250 m
  • Groundwater recorded about 7.2 m below ground nearbyThe middle water level in the well records within 500 m (17 records). It changes with the season and from spot to spot.500 m

Toronto and Region Conservation Authority · Province of Ontario open data

Planning and building activity1

  • Inside the Greenbelt (Oak Ridges Moraine Conservation Plan) and the Oak Ridges Moraine plan area (Natural Core Area)These provincial plans set policies on new buildings, new lots and some changes to the land; the municipality can say which apply to this property.At the address

Province of Ontario open data

Around the home2

  • Nearest rail line: 110 m110 m
  • A trail or path within 1 km1 km

Province of Ontario open data · Provincial and municipal trail maps

Environmental records4

  • No licensed pit or quarry within 2 km2 km
  • No recorded oil, gas or salt well within 250 m250 m
  • No facility within 1 km reports pollutant releases to Environment CanadaOnly facilities above the inventory’s reporting thresholds are listed.1 km
  • No federal contaminated site within 1 kmThe federal inventory covers federal land only; it says nothing about provincial or private sites.1 km

Province of Ontario open data · Government of Canada open data

Power and internet3

  • Electricity is distributed here by Elexicon Energy Inc.At the address
  • Wired internet 50/10 Mbps or faster is listed at a household 140 m awayFixed wireless up to 25/5 Mbps. LTE mobile coverage listed. ISED’s National Broadband Data at the nearest household point (140 m from the listing); 50/10 Mbps is its top category and includes faster plans. Confirm with a provider for this address.140 m
  • Across the surrounding area: fibre to the home, cable, DSL internet listedFibre to the home: Bell. Cable: Rogers. DSL: Bell. Fixed wireless: 4KNetworks, Bell, Dash Networks, Rogers, Routcom, Ruralwave, Vianet. Mobile: Bell, Freedom Mobile, Rogers, Telus. Satellite: Xplore. ISED’s list for the surrounding ~25 km² area; check with a provider for this address.Area-wide

Ontario Energy Board · Innovation, Science and Economic Development Canada

Each record is placed at the distance its own line states. None of it is an inspection of the property. Confirm anything that matters to you with the municipality, Toronto and Region Conservation Authority or the record’s publisher.

Contains information licensed under the Open Government Licence – Canada. Contains information licensed under the Open Government Licence – Ontario. Contains information made available under the Toronto and Region Conservation Authority Open Data Licence v1.0.

Schools nearby

ElementaryTypeDistanceEQAO average 2024–25
Claremont Public SchoolDurham DSBPublic · grades JK–81.8 km66%Grade 6 average
Valley View Public SchoolDurham DSBPublic · grades JK–88.1 km88%Grade 6 average
Barbara Reid Public SchoolYork Region DSBPublic · grades JK–88.3 km83%Grade 6 average
St Brigid Catholic Elementary SchoolYork CDSBCatholic · grades JK–89.5 km83%Grade 6 average
SecondaryTypeDistanceGrade 9 math 2024–25
ÉSC Pape-FrançoisConseil scolaire catholique MonAvenirFrench-language Catholic · grades 9–1211 km86%Grade 9 math
Stouffville District Secondary SchoolYork Region DSBPublic · grades 9–1211 km63%Grade 9 math
Brooklin High SchoolDurham DSBPublic · grades 9–1213 km62%Grade 9 math
Bill Hogarth Secondary SchoolYork Region DSBPublic · grades 9–12 · French Immersion13 km78%Grade 9 math

EQAO: share of students at or above the provincial standard, 2024–25 (Ontario open data). These are the schools nearest this home, not the schools it is assigned to: boundaries change, and some schools take students by application. Confirm with the board before you buy. Contains information licensed under the Open Government Licence – Ontario.

Lot

Street frontage
1,308.4 ft398.8 m
Depth
2,659.53 ft810.6 m
Lot size
50 – 99.99 acresAs the board bands it

The record marks this lot irregular, so its area is not the frontage multiplied by the depth. It is not given here. Confirm with a survey before you buy.

Source: the MLS® listing record, measured by GeoWarehouse.

Comparable sales

Comparable sales require sign in

Closing prices and sold comps are available to registered visitors who accept MLS® VOW terms on this site.

Mortgage Calculator

Plan with the current asking price

20% · $1,960,000

CMHC insurance: not required at 20% down. Payments use Canadian semi-annual compounding.

Mortgage Details

4.8% · 5-year term · 25-year amortization · 20% down

Total down payment
$1,960,000
Total mortgage amount
$7,840,000
Total interest payment
$5,573,000
Total purchase cost
$15,373,000
Mortgage payment
$44,710/mo

Cash Flow Analysis

If you rented this home out at 20% down

Break-even down payment

—

Monthly carrying cost

$45,529
−$45,529per month
  • Rent $0
  • Shortfall $45,529

Rental income starts at $0: enter the rent you expect. This is a planning tool, not advice.

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