Some streets are more than an address. Watson Avenue is one of Old Oakville's most admired, cherished for its mature tree canopy, beautiful homes, renowned schools and exceptional walkability to Downtown Oakville. Welcome to 286 Watson Avenue, a charming, move-in-ready home thoughtfully updated by its current owners. Recent improvements inside and out include freshly painted wood siding, custom Inline Fibreglass windows and front door, and refreshed landscaping that creates a warm welcome from the moment you arrive. Inside offers over 2300sqft of living space, with vintage Oak hardwood floors and generously proportioned principal rooms bringing warmth and character throughout. The main floor offers both formal living and dining rooms, alongside a bright white kitchen appointed with Wolf and Sub-Zero appliances. A cozy breakfast nook and wood-burning fireplace make it a natural gathering place, while expansive windows frame views of the backyard and gardens. Upstairs, three well-sized bedrooms feature generous closets, newer hardwood flooring, updated trim and fresh paint. Two renovated bathrooms complete the level. The finished walk-out basement adds valuable flexibility, with a spacious recreation room, room for a home office or gym, a full bathroom and a renovated laundry room with additional storage. The west-facing backyard is a private, sun-drenched retreat, framed by mature trees and beautifully established gardens. Spend summer afternoons by the heated 16' x 32' in ground pool, or gather with family and friends in the cabana. A special opportunity to enjoy a thoughtfully updated home, a wonderful outdoor setting and the distinctive lifestyle of one of Old Oakville's most coveted streets. See the attached list of improvements for additional details.
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
2-Storey
Approx. Age:
51-99
Total Approx Floor Area:
1500-2000
Lot Size:
<.50
Lot Depth:
150'45.7 m
Lot Frontage:
46'14 m
Lot Shape:
Rectangular
Topography:
Flat
Direction Faces:
West
Bedrooms:
3
Bathrooms:
4.0
Water supply:
Municipal
Kitchens:
1
Bedrooms Above Grade:
3
Kitchens Above Grade:
1
Rooms Above Grade:
10
Fractional Ownership:
No
Assignment:
No
Heating type:
Forced Air
Heating Fuel:
Gas
Fireplaces:
3
Foundation:
Block
Roof:
Asphalt Shingle
Basement:
Finished with Walk-Out
Fireplace Features:
Wood, Natural Gas
Fireplace/Stove:
Yes
Garage:
Attached
Garage Spaces:
1.0
Other Structures:
Fence - Full, Garden Shed, Storage, Workshop
Parking Features:
Private
Parking Spaces:
6
Total Parking Spaces:
7.0
Family Room:
No
Possession Details:
Flexible
Pool:
Inground
Link:
No
HST Applicable To Sale Price:
Included In
Taxes:
$11,973.36 /
2026
Assessment:
$- /
-
Halton
Oakville
1013 - OO Old Oakville
Fenced Yard, Park, Public Transit, Rec./Commun.Centre, School
Auto Garage Door Remote, Bar Fridge
Landscape Lighting, Landscaped, Lawn Sprinkler System, Lighting, Patio, Privacy, Year Round Living
Sub zero refrigerator, wolf gas stove, built in microwave, built in dishwasher, Hood vent, kitchen bar fridge, basement bar fridge, washer & dryer, garage door opener + remote, all pool equipment + safety cover, back yard shed, backyard cabana
Data was last updated November 5, 2026 at 08:31 PM (UTC)
Area Statistics
Listings on market:
26
Avg list price:
$4,182,000
Min list price:
$1,649,999
Max list price:
$10,900,000
Avg days on market:
54
Min days on market:
7
Max days on market:
409
These statistics are generated based on the current listing's property type
and located in
1013 - OO Old Oakville. 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.