$ 5,130,000

317 Gloucester Avenue, Oakville

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. (id:1945)
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Property details for 317 Gloucester Avenue, Oakville

Type
Residential
Bedrooms
5
Bathrooms
4
Living Area
5,246 square feet
Lot Size
154.7 x 151.3 FT
Stories
2.5
Basement
Partially finished, Full
Parking
Attached Garage, Garage
Heating
Radiant heat, Other
Cooling
Central air conditioning
Exterior
Stucco
Ownership
Freehold
Annual Taxes
$24,430

Nearby Listings Stat

Estimated price and comparable properties near 317 Gloucester Avenue

Active Listings
10
Min Price
$1,299,000
Max Price
$15,900,000
Avg Price
$4,955,470
Days on Market
44
days
Sold Listings
6
Min Sold Price
$1,799,000
Max Sold Price
$3,099,000
Avg Sold Price
$2,664,500
Days until Sold
34
days

Price History

Listed
October 9, 2026
by RE/MAX REALTY ENTERPRISES INC.
Current Price
$5,130,000
+3% from last change
Type
Residential
For Sale
Price Changes
3
Date Price Change
Current $5,130,000 +$150,000 (+3%)
Oct 9, 2026 $4,980,000 $600,000 (-10.8%)
May 22, 2026 $5,580,000 $120,000 (-2.1%)
Apr 22, 2026 $5,700,000 Listed

Contact Agent Get in touch about 317 Gloucester Avenue, Oakville

TONY DEAKON
TONY DEAKON
RE/MAX REALTY ENTERPRISES INC.