317 Gloucester Avenue, Oakville, ON L6J 3W8
Timeless Elegance in the Heart of Olde Oakville. A rare property on one of the community's most coveted streets. Experience refined living in this exceptional residence set on a triple lot over 1/2 acres with an impressive 154.73ft frontage, curated for those who value privacy, design and indoor-outdoor living at its finest. Beautifully reimagined in 2024 & 2026, the main level showcases a sophisticated blend of transitional elegance and casual upscale comfort, perfect for both everyday living and effortless entertaining. A Main Floor Redesigned for Modern Luxury. Step inside to wide-plank oak hardwood floors, luxurious finishes, and stunning sightlines to the property's park-like grounds. The custom kitchen is a true showpiece, featuring: Main kitchen+ second "messy kitchen" for concealed prep, storage, and small appliances. Square island with integrated fridge/freezer drawers. Quartz countertops & full-height backsplash in both kitchens. Built-in wine/beverage and dedicated coffee station. A walk-out from the dining room and a large picture window open to views of the serene screened-in sun porch ,creating a seamless flow for indoor-outdoor enjoyment. The magnificent great room features dramatic cathedral ceilings, a stone wood-burning fireplace with aged beam mantel. A second walk-out continues to the sun porch framed by nature. The upper level has been thoughtfully elevated with beautiful new wide plank oak hardwood flooring creating a warm and sophisticated foundation for the home. This exceptional level features flexible living spaces with 4 bedrooms and 3 full bathrooms offering both comfort and functionality. Third floor loft/suite ideal as 4th bedroom, guest suite or office. Every detail has been carefully considered, including new custom window coverings throughout & beautifully appointed spaces filled with natural light.
Dining Room
W/O To Deck, Hardwood Floor, Picture Window
6.22 x 4.22
Ground
Kitchen
Open Concept, Centre Island, Hardwood Floor
9.07 x 4.27
Ground
Great Room
Hardwood Floor, Fireplace, Cathedral Ceiling(s)
7.21 x 6.08 m
Ground
Sunroom
4.7 x 3.63 m
Ground
Primary Bedroom
Large Closet, 5 Pc Ensuite, Hardwood Floor
8.48 x 3.45
Second
Foyer
Hardwood Floor
2.82 x 2.39
Main
Bedroom 2
Walk-In Closet(s), Hardwood Floor
4.04 x 3.4 m
Second
Bedroom 3
Walk-In Closet(s), Hardwood Floor
3.35 x 3.33 m
Second
Bedroom 4
3 Pc Ensuite, Cedar Closet(s), Hardwood Floor
4.44 x 4.04
Third
Recreation
8.64 x 4.19 m
Basement
Interior features
Auto Garage Door Remote, Bar Fridge, Water Softener
Basement
Full, Partially Finished
Bathrooms
1 × 3-piece — Ground, 1 × 3-piece — Second, 1 × 5-piece — Second, 1 × 3-piece — Third
Fireplace
Yes
Family room
Yes
Kitchens
1
Rooms (above / below grade)
8 above, 1 below
Architectural style
2 1/2 Storey
Construction materials
Stucco (Plaster)
Foundation
Concrete Block
Roof
Asphalt Shingle
Exterior features
Landscaped, Deck, Landscape Lighting, Lawn Sprinkler System, Patio, Privacy, Porch Enclosed
Direction faces
East
Garage type
Attached
Garage spaces
2
Total parking spaces
12
Driveway parking
10
Parking features
Private Double
Lot size
154.73 x 151.34 ft
Cross street
Lakeshore & Gloucester
Directions
Lakeshore to Gloucester
Neighbourhood
1013 - OO Old Oakville
Heating
Radiant — Other
Cooling
Central Air
Water
Sewer
Sewer
List price
$5,130,000
Original list price
Annual taxes
$24,430
Tax year
2026
Legal description
PT LT 78, PL 1009 , PART 4 , 20R1646 ; OAKVILLE
Inclusions
Exclusions
MLS #
W13879172
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 REALTY ENTERPRISES INC.
$3,795,000
Median list price
23
Active listings
New in last 30 days
Median days on market
Estimated monthly payment
$24,593
Educational estimate only — actual payment depends on your lender, credit, and insurance requirements.
Sign in to see recent sold prices for homes like this one nearby.

$4,999,000
488 Macdonald Road, Oakville, ON L6J 2B9
RE/MAX Escarpment Realty Inc., Brokerage

$4,290,000
Lot 101 Douglas Avenue, Oakville, ON L6J 2B7
CENTURY 21 MILLER REAL ESTATE LTD.

$4,265,000
343 Douglas Avenue, Oakville, ON L6J 3S7
ROYAL LEPAGE REAL ESTATE SERVICES PHINNEY REAL EST

$4,149,000
426 Trafalgar Road, Oakville, ON L6J 3H7
RE/MAX ABOUTOWNE REALTY CORP.

$6,250,000
533 Carson Lane, Oakville, ON L6J 6M3
ROYAL LEPAGE REAL ESTATE SERVICES PHINNEY REAL EST

$3,949,000
287 MacDonald Road, Oakville, ON L6J 2A6
RE/MAX Escarpment Realty Inc., Brokerage