15 Shepherd Road, Whitby, ON L1M 1G8
A rare bungalow offering in Whitby's Macedonian Village. Set on an exceptional 102.48 x 352.51 ft lot backing onto Heber Down Conservation Area, this custom home combines impressive main-floor living, privacy and substantial indoor and outdoor space. The approximately 3,025 sq. ft. main level is designed around comfortable one-floor living, with four spacious bedrooms, each featuring its own en-suite and walk-in closet. Soaring 10-ft ceilings, new R60 attic insulation, new engineered hardwood flooring, and extensive mouldings run throughout the principal rooms. At the heart of the home, the kitchen and dining area feature an impressive waffle ceiling, while the adjoining great room opens dramatically beneath a 16-ft cathedral ceiling, with a gas fireplace and expansive windows framing the private conservation setting. The primary suite enjoys backyard views and features a custom ceiling with pot lights, a generous dressing room, and a 5-piece en suite. A main-floor office and laundry add everyday convenience. Downstairs, the finished walk-out lower level substantially expands the home's possibilities with three additional bedrooms, a rough-in kitchen, two large recreation areas, a gym, a gas fireplace, and a kitchen rough-in, providing exceptional flexibility for guests, extended family, recreation, hobbies, or future personalization. Outside, the property's extraordinary depth creates a private setting surrounded by mature greenery, with an 18 x 36 ft in-ground pool, updated liner, heater, and UV system. An attached workshop with an approximately 13-ft ceiling and 60-amp service adds another unique dimension for a car enthusiast, hobbyist, studio or golf-simulator space. Additional updates include fresh interior paint (2025), a water softener and an iron-removal system. No rental items.For buyers seeking a substantial bungalow on an estate-sized lot with conservation views, privacy and room to make the property their own.
Kitchen
Hardwood Floor, Quartz Counter, Combined w/Dining
8.89 x 5.11
Main
Dining Room
Combined w/Kitchen, Hardwood Floor, Crown Moulding
8.89 x 5.11
Main
Great Room
Hardwood Floor, Cathedral Ceiling(s), Gas Fireplace
5.06 x 5.34
Main
Office
Hardwood Floor, Crown Moulding, Overlook Greenbelt
3.48 x 3.09
Main
Primary Bedroom
Hardwood Floor, 5 Pc Ensuite, California Shutters
3.94 x 5.78
Main
Bedroom 2
3 Pc Ensuite, Hardwood Floor, Overlooks Backyard
5.05 x 4.54
Main
Bedroom 3
3 Pc Ensuite, Hardwood Floor, Crown Moulding
3.81 x 4.55
Main
Bedroom 4
3 Pc Ensuite, Hardwood Floor, Crown Moulding
3.53 x 4.06
Main
Bedroom 5
3 Pc Ensuite, Hardwood Floor, Overlooks Backyard
5 x 4.28
Basement
Bedroom
Hardwood Floor, Window, Closet
4.1 x 3.49
Basement
Bedroom
Hardwood Floor, Window, Closet
4.09 x 3.25
Basement
Family Room
Hardwood Floor, Pot Lights, Walk-Out
5.02 x 10.75
Basement
Recreation
Hardwood Floor, Pot Lights
8.55 x 6.73
Basement
Exercise Room
Hardwood Floor, Overlooks Backyard, Large Window
4.68 x 5.28
Basement
Laundry
Tile Floor, Window, Crown Moulding
2.69 x 3.63
Main
Foyer
Tile Floor, Crown Moulding
3.94 x 2.14
Main
Interior features
Built-In Oven
Basement
Finished with Walk-Out
Bathrooms
1 × 5-piece — Main, 1 × 3-piece — Main, 1 × 3-piece — Main, 1 × 3-piece — Main, 1 × 2-piece — Main
Fireplace
Yes
Family room
Yes
Kitchens
1
Rooms (above / below grade)
15 above, 8 below
Architectural style
Bungalow
Construction materials
Brick, Stone
Foundation
Concrete
Roof
Shingles
Direction faces
East
Pool
Inground
Garage type
Attached
Garage spaces
2
Total parking spaces
12
Driveway parking
10
Parking features
Private, Circular Drive, Front Yard Parking, Private Double
Lot size
102.48 x 352.33 ft
Cross street
Coronation and Winchester Rd W
Directions
Coronation and Winchester Rd W
Neighbourhood
Rural Whitby
Heating
Forced Air — Gas
Cooling
Central Air
Water
Sewer
Septic
List price
$2,397,000
Original list price
Annual taxes
$14,007
Tax year
2026
Legal description
Pcl 5-1 Sec M42; Lt 5, Plan M42
Inclusions
Exclusions
MLS #
E14033110
Status
Active
Transaction type
For Sale
Property type
Residential Freehold
Property sub type
Detached
Days on market
List date
Possession
Flexible
Occupancy
Owner
Listing brokerage
Re/Max Hallmark First Group Realty Ltd.
$1,299,450
Median list price
40
Active listings
New in last 30 days
Median days on market
Estimated monthly payment
$11,491
Educational estimate only — actual payment depends on your lender, credit, and insurance requirements.
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