Detached in Oakville (Oo Old Oakville)

Browse 34 active listings

$3,695,000
Median

Market Analysis

In Oakville's Old Oakville neighborhood, the detached home market attracts a diverse clientele, ranging from young families seeking spacious residences to retirees looking for tranquility near the lakeshore. Many buyers are drawn to the lifestyle that combines suburban comfort with urban convenience. The area is known for its picturesque streets and vibrant community life, appealing to those who value a sense of belonging. Families often prioritize proximity to high-ranking schools like St. Mildred's-Lightbourn School and E.J. James Public School. Professionals who work in Toronto appreciate the ease of commuting from the Oakville GO Station, located near the scenic Kerr Village, which adds to the neighborhood's allure. Additionally, with a balanced market providing steady options, buyers can find homes that cater to both their practical needs and lifestyle aspirations, whether they're looking for a historic property on Lakeshore Road or a modern build on Maple Grove Drive.

Price Insights

The average price of detached homes in Old Oakville sits at a notable $4,235,948, reflecting the premium nature of this sought-after area. Buyers can expect to discover a range of properties, from charming heritage homes with character on streets like Thomas Street, to contemporary builds featuring open-concept designs and luxurious finishes on Oakville's premier cul-de-sacs. Each price band offers something unique, and the variety in architectural styles means that potential homeowners can select a residence that not only meets their budget but also aligns with their aesthetic preferences. For instance, a well-preserved Victorian property may command a higher price due to its historical significance, while a newly constructed home with energy-efficient features could present a more modern option, catering to eco-conscious buyers. This balanced market allows for strategic decision-making, ensuring that buyers can make informed choices without compromising on quality or location.

Available Properties

View all on map
🏠
No Photo Available
494 Chartwell Road
+38 photos
$1,920,000
494 Chartwell Road
Oakville (OO Old Oakville), Ontario
6 beds • 3 baths
Detached Home
Gorgeous Family Home on Prestigious Chartwell Road in Old OakvilleNestled on a prime 0.29-acre west-...
🏠
No Photo Available
74 Howard Avenue
+31 photos
$5,500,000
74 Howard Avenue
Oakville (OO Old Oakville), Ontario
5 beds • 4 baths
Detached Home
This English Country Garden home, framed by a storybook white picket fence, sits on a truly exceptio...
🏠
No Photo Available
69 Allan Street
+40 photos
$3,695,000
69 Allan Street
Oakville (OO Old Oakville), Ontario
3 beds • 4 baths
Detached Home
Located south of Lakeshore, this beautiful turn-key Bungaloft offers the rare combination of contemp...
🏠
No Photo Available
184 Chartwell Road
+30 photos
$5,699,000
184 Chartwell Road
Oakville (OO Old Oakville), Ontario
5 beds • 7 baths
Detached Home
Welcome to 184 Chartwell Road, a distinguished residence offering over 7,800 sq. ft. of living space...
🏠
No Photo Available
1123 Lakeshore Road East
+41 photos
$2,699,000
1123 Lakeshore Road East
Oakville (OO Old Oakville), Ontario
5 beds • 3 baths
Detached Home
Welcome to 1123 Lakeshore Road, Bright, sun-filled and nestled on a rare and expansive 100 x 150 ft...
🏠
No Photo Available
78 Trafalgar Road
+32 photos
$3,495,000
78 Trafalgar Road
Oakville (OO Old Oakville), Ontario
3 beds • 4 baths
Detached Home
Welcome to this stunning, never before lived in custom-built 3-storey townhouse in the heart of down...
🏠
No Photo Available
116 Chartwell Road
+38 photos
$7,995,000
116 Chartwell Road
Oakville (OO Old Oakville), Ontario
4 beds • 6 baths
Detached Home
Welcome to 116 Chartwell Road, one of Southeast Oakville's architecturally significant and environme...
🏠
No Photo Available
506 Maple Avenue
+22 photos
Price on Request
506 Maple Avenue
Oakville (OO Old Oakville), Ontario
5 beds • 3 baths
Detached Home
Renovated 4 Bedrm, 3 Bathrm Home In Old Oakville On Ravine Lot. Walking Distance To Downtown. Open C...
🏠
No Photo Available
376 Chartwell Road
+49 photos
$4,400,000
376 Chartwell Road
Oakville (OO Old Oakville), Ontario
6 beds • 5 baths
Detached Home
A truly one-of-a-kind, professionally restored home that blends timeless Victorian charm with modern...
🏠
No Photo Available
350 King Street
+49 photos
$12,900,000
350 King Street
Oakville (OO Old Oakville), Ontario
5 beds • 5 baths
Detached Home
Nestled in the heart of downtown Oakville, this magnificent historical home offers unparalleled char...
🏠
No Photo Available
288 Trafalgar Road
+42 photos
$1,749,900
288 Trafalgar Road
Oakville (OO Old Oakville), Ontario
3 beds • 2 baths
Detached Home
RARE WATERFRONT OPPORTUNITY IN OLD OAKVILLE! Discover a rare opportunity to own a Waterfront Propert...
🏠
No Photo Available
200 Chartwell Road
+49 photos
$6,299,000
200 Chartwell Road
Oakville (OO Old Oakville), Ontario
5 beds • 7 baths
Detached Home
Nestled behind private gates on one of Oakville's most coveted "Street of Dreams," this exceptional ...

About This Property Type

Detached homes in Old Oakville are characterized by their spacious layouts and diverse architectural styles, ranging from classic designs to modern masterpieces. These properties often feature large lots, providing ample outdoor space for gardens or recreational areas, which is particularly appealing to families. Homes along Morrison Road and by the prestigious Oakville Golf Club are known for their expansive yards and scenic views, lending a certain prestige to the neighborhood. The construction quality tends to be high, with many homes boasting premium finishes and upgraded amenities such as gourmet kitchens and custom cabinetry. Buyers can often find features like finished basements, multi-car garages, and luxurious master suites that enhance everyday living, making these properties not just residences, but true family sanctuaries.

Location Highlights

Old Oakville is celebrated for its blend of heritage charm and modern conveniences, making it a unique enclave in Ontario. The region is bordered by the picturesque shores of Lake Ontario, where residents can enjoy scenic views and waterfront parks like Bronte Creek Provincial Park and the tranquil Coronation Park. These green spaces provide opportunities for outdoor activities, from walking and cycling to picnicking with family. Moreover, the community is rich in cultural establishments, including the Oakville Centre for the Performing Arts and the local art galleries that host various exhibitions throughout the year. Shopping is a delight, with the trendy boutiques lining Kerr Street and the bustling Oakville Place offering everything from gourmet dining to unique retail experiences, ensuring there’s always something to enjoy just a stone's throw away.

Investment Advice

Investing in a detached home in Old Oakville presents a smart long-term strategy, particularly given the area's consistent property value growth. With its desirable location and family-friendly amenities, homes in this neighborhood tend to retain their worth, making them a reliable investment for buyers. The surrounding community is known for its stable economic conditions, which are bolstered by continuous interest from affluent buyers looking for quality living spaces. Furthermore, the ongoing development in the area signals a healthy future for property values. Prospective homeowners should consider that while the initial costs may be higher than average, the potential for appreciation and the quality of life provided by Old Oakville can yield significant returns in both monetary and lifestyle satisfaction.

Buying Tips

When considering a detached home in Old Oakville, it’s beneficial to prioritize specific neighborhoods that align with your lifestyle needs and budget. Each street, such as the family-friendly areas near Trafalgar Road, offers unique characteristics that may appeal to different buyers, from vibrant community activities to quiet, serene surroundings. It's wise to enlist the help of a local real estate expert who understands the nuances of the Oakville market and can guide you through the intricacies of purchasing a home in this competitive area. Additionally, consider visiting open houses and exploring the community during different times of the day to get a genuine feel for the neighborhood. This hands-on approach will help you identify the perfect property that not only fits your needs but also feels like home.

Related Searches

Frequently Asked Questions About Oakville (Oo Old Oakville)

There are currently 34 detached homes listed for sale in Oakville (Oo Old Oakville). Listings are updated multiple times per day from CREA's DDF®.

REALTOR®, REALTORS®, and the REALTOR® logo are certification marks that are owned by REALTOR® Canada Inc. and licensed exclusively to The Canadian Real Estate Association (CREA). These certification marks identify real estate professionals who are members of CREA and who must abide by CREA's By-Laws, Rules, and the REALTOR® Code.

The MLS® trademark and the MLS® logo are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA.

The information contained on this site is based in whole or in part on information that is provided by members of CREA, who are responsible for its accuracy. CREA reproduces and distributes this information as a service for its members and assumes no responsibility for its accuracy.

The listing content on this website is protected by copyright and other laws. Screen scraping, database scraping, and all other forms of automated data collection are prohibited.

Oakwyn Realty Ltd.

Oakwyn Realty Ltd.

Search Listings Online Inc.

3195 Oak St, Vancouver, BC V6H 2L2

REALTOR®, REALTORS®, and the REALTOR® logo are certification marks that are owned by REALTOR® Canada Inc. and licensed exclusively to The Canadian Real Estate Association (CREA). These certification marks identify real estate professionals who are members of CREA and who must abide by CREA's By-Laws, Rules, and the REALTOR® Code. The MLS® trademark and the MLS® logo are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. The information contained on this site is based in whole or in part on information that is provided by members of CREA, who are responsible for its accuracy. CREA reproduces and distributes this information as a service for its members and assumes no responsibility for its accuracy.

The listing content on this website is protected by copyright and other laws. Screen scraping, database scraping, and all other forms of automated data collection are prohibited.

© 2026 Search Listings Online. Powered by CREA DDF