Discover winter luxury at 15 Shepherd Road, a custom luxury bungalow set on a premium 102.48 ft x 352.51 ft lot backing onto the peaceful winter landscape of Heber Down Conservation Area. This beautifully updated home features four main-floor bedrooms, each with its own en-suite and walk-in closet, 10-foot ceilings, new engineered hardwood floors, fresh paint (2025), and a stunning great room with a 16-foot cathedral ceiling and gas fireplace. The brand-new kitchen includes stainless steel appliances, crown moulding, large baseboards, and California shutters. The primary suite offers a custom ceiling with pot lights, a spacious walk-in dressing room, and a 5-piece spa-like en-suite with views of the pool and conservation area. The finished walk-out basement adds exceptional versatility with three additional bedrooms, a gym, two recreation rooms, a gas fireplace, and a rough-in kitchen ideal for multi-generational living. The attached workshop with 60 Amp service provides space for hobbies, a golf simulator, or storage. With its brick, stone, and stucco exterior, updated pool system (new liner, heater, UV system Aug 2025), and no rental items, this is a rare opportunity in prestigious Macedonian Village-luxury, privacy, and comfort in every season.
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
Bungalow
Total Approx Floor Area:
3000-3500
Lot Size:
.50-1.99
Lot Depth:
352'4"107 m
Lot Frontage:
102'5¾"31.2 m
Lot Details:
100.00 x 352.33 Feet
Direction Faces:
East
Bedrooms:
4+3
Bathrooms:
7.0
Water supply:
Well
Kitchens:
1
Bedrooms Above Grade:
4
Bedrooms Below Grade:
3
Kitchens Above Grade:
1
# Main Level Bedrooms:
2
# Main Level Bathrooms:
0
Rooms Above Grade:
15
Rooms Below Grade:
8
Rooms:
10
Heating type:
Forced Air
Heating Fuel:
Gas
Cooling:
Yes
Foundation:
Concrete
Roof:
Shingles
Basement:
Finished with Walk-Out
Fireplace Features:
Natural Gas
Fireplace/Stove:
Yes
Attached Garage:
Yes
Garage:
Attached
Garage Spaces:
2.0
Other Structures:
Workshop
Parking Features:
Private, Circular Drive, Front Yard Parking, Private Double
Parking Spaces:
10
Total Parking Spaces:
12.0
Family Room:
Yes
Possession Details:
TBD
Pool:
Inground
Link:
No
HST Applicable To Sale Price:
Included In
Taxes:
$14,041 /
2025
Assessment:
$- /
-
Durham
Whitby
Rural Whitby
Cul de Sac/Dead End, Greenbelt/Conservation, Ravine, Fenced Yard, School Bus Route, River/Stream
Data was last updated December 11, 2025 at 04:15 PM (UTC)
Area Statistics
Listings on market:
39
Avg list price:
$1,499,990
Min list price:
$749,000
Max list price:
$4,198,000
Avg days on market:
37
Min days on market:
1
Max days on market:
305
These statistics are generated based on the current listing's property type
and located in
Rural Whitby. Average values are
derived using median calculations. This data is not produced by the MLS® system.
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website.
The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.