Advantage Group Real Estate
286 Watson Avenue • Oakville, ON photo 1
286 Watson Avenue • Oakville, ON photo 2
286 Watson Avenue • Oakville, ON photo 3
286 Watson Avenue • Oakville, ON photo 4
286 Watson Avenue • Oakville, ON photo 5
286 Watson Avenue • Oakville, ON photo 6
286 Watson Avenue • Oakville, ON photo 7
286 Watson Avenue • Oakville, ON photo 8
286 Watson Avenue • Oakville, ON photo 9
286 Watson Avenue • Oakville, ON photo 10
286 Watson Avenue • Oakville, ON photo 11
286 Watson Avenue • Oakville, ON photo 12
286 Watson Avenue • Oakville, ON photo 13
286 Watson Avenue • Oakville, ON photo 14
286 Watson Avenue • Oakville, ON photo 15
286 Watson Avenue • Oakville, ON photo 16
286 Watson Avenue • Oakville, ON photo 17
286 Watson Avenue • Oakville, ON photo 18
286 Watson Avenue • Oakville, ON photo 19
286 Watson Avenue • Oakville, ON photo 20
286 Watson Avenue • Oakville, ON photo 21
286 Watson Avenue • Oakville, ON photo 22
286 Watson Avenue • Oakville, ON photo 23
286 Watson Avenue • Oakville, ON photo 24
286 Watson Avenue • Oakville, ON photo 25
286 Watson Avenue • Oakville, ON photo 26
286 Watson Avenue • Oakville, ON photo 27
286 Watson Avenue • Oakville, ON photo 28
286 Watson Avenue • Oakville, ON photo 29
286 Watson Avenue • Oakville, ON photo 30
286 Watson Avenue • Oakville, ON photo 31
286 Watson Avenue • Oakville, ON photo 32
286 Watson Avenue • Oakville, ON photo 33
286 Watson Avenue • Oakville, ON photo 34
286 Watson Avenue • Oakville, ON photo 35
286 Watson Avenue • Oakville, ON photo 36
286 Watson Avenue • Oakville, ON photo 37
286 Watson Avenue • Oakville, ON photo 38
286 Watson Avenue • Oakville, ON photo 39
286 Watson Avenue • Oakville, ON photo 40
286 Watson Avenue • Oakville, ON photo 41
286 Watson Avenue • Oakville, ON photo 42
286 Watson Avenue • Oakville, ON photo 43
286 Watson Avenue • Oakville, ON photo 44
286 Watson Avenue • Oakville, ON photo 45
286 Watson Avenue • Oakville, ON photo 46
286 Watson Avenue • Oakville, ON photo 47
286 Watson Avenue • Oakville, ON photo 48
286 Watson Avenue • Oakville, ON photo 49
286 Watson Avenue • Oakville, ON photo 50
New1 / 50
$2,950,000
286 Watson Avenue • Oakville, ONNew
Courtesy of RE/MAX ABOUTOWNE REALTY CORP.
3
Bedrooms
4
Bathrooms
1500-2000
Square feet
7
Parking

About this home

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 details

Property type
Detached
Style
2-Storey
Approx. age (yrs)
51-99
Total rooms
10
Lot size
46 × 150 ft
Property taxes
$11,973.36 (2026)
Occupancy
Flexible
Days on market
1
Status
Active
MLS®

Property history

Recently sold nearby

Listing data last updated: Nov 5, 2026, 10:08 a.m. EST via TRREB IDX.

First listed: Nov 5, 2026, 10:08 a.m. EST.