416-800-1055
Are You a Realtor? JOIN US

Old Oakville MLS® Listings

(34)
1 2 Next
418 Queen Mary Dr, Oakville
$3,128,800 CAD
6 baths
4+1 beds
( )
22.45658 BTC
**Stunning 2015-Built Home in sought-after Old Oakville Neighborhood**This exceptional home offers an expansive and thoughtfully designed layout that perfectly balances luxury, comfort, and practicality. With soaring 22-foot ceilings on the foyer and a grand 14-foot...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
416 Trafalgar Rd, Oakville
$3,599,000 CAD
4 baths
2+2 beds
Trafalgar Rd
( )
25.83138 BTC
Mile high luxury & vista views on the river. Welcome to 416 Trafalgar Rd! Nestled in the prestigious enclave of Old Oakville, this reno'd character home charms w/ its riverside locale & riparian privileges along 16 Mile Creek. This 4BED, 3.5BATH RES offers LUX combined...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
325 Ulric Cres, Oakville
$1,428,000 CAD
3 baths
3 beds
Ulric Cres
( )
10.24929 BTC
Do Not Miss It! Solid, Meticulously Maintained And Updated With The Attention To Quality And Details 3 Bedrooms 3 Washrooms Family Home Located On A Quite Crescent In The Heart Of Central South Oakville. This Home Is Perfect For Entertaining. Over 2800 sq.ft . Of...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
95 Bel Air Dr, Oakville
$5,519,800 CAD
5 baths
3+2 beds
Bel Air Dr
( )
39.61769 BTC
Nestled on the exclusive Bel Air Drive, home to just 13 families, this beautifully proportioned residence sits on a 103.35' x 148.59' lot in a highly sought-after South East enclave. Boasting 7,715 sq ft of elegant living space, this home showcases exquisite...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
282 Tudor Ave, Oakville
$3,699,000 CAD
6 baths
4+1 beds
Tudor Ave
( )
26.54912 BTC
Welcome to this exclusive enclave of Fernbrook homes known as The Royal Oakville Club, minutes from Downtown Oakville. This model features over 4000 square ft and has over $1M in builder upgrades. This home has been designed and customized for the most discerning buyer...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
179 Douglas Ave, Oakville
$4,680,000 CAD
5 baths
4+1 beds
Douglas Ave
( )
33.59012 BTC
Nestled just steps from the vibrant core of downtown Oakville, this custom-designed farmhouse redefines luxury living. Boasting 4+1 bedrooms and 5 bathrooms, this remarkable residence seamlessly integrates functionality with upscale features. As you enter, you're...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
430 Reynolds St, Oakville
$2,998,000 CAD
5 baths
4+1 beds
Reynolds St
( )
21.51778 BTC
Luxurious Custom Home Built in 2021 with Open Concept Design. 9 Ft Ceiling and Oak Hardwood Flooring on Ground Level and 2nd Floor. Solid Maple Wood Doors, High End Finishes and Large Windows. Beautiful Skylight Above Staircases. Modern Gourmet Kitchen with Built-In...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
55 Stewart St, Oakville
$875,000 CAD
1 baths
3 beds
Stewart St
( )
6.28020 BTC
*Opportunity Knocks * Attention Contractors, Builders, First Time Buyers * Build Your Dream Home In Oakville's Sought After Family Friendly Community Just Steps From The Welcoming, Eclectic And Trendy Vibe Of Kerr Village * Prime Chance To Own This Fully Detached Home...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
163 Maurice Dr, Oakville
$1,250,000 CAD
2 baths
3+1 beds
Maurice Dr
( )
8.97172 BTC
Located in Oakville's Kerr Village community, this property offers endless possibilities in a sought-after location. Situated on a spacious lot with RL10-0 zoning and walking distance to Lakeshore, downtown Oakville, public transit, and minutes to Highways 403/QEW/407...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
128 Balsam Dr, Oakville
$7,350,000 CAD
10 baths
5+2 beds
Balsam Dr
( )
52.75372 BTC
Discover luxury living in this exquisite custom-built West Coast-style home, nestled on a prestigious street in Southeast Oakville. This opulent residence boasts an impressive 5,484 sq ft above grade, w/ over 9,000 sq ft of finished living space, perfect for both...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
214 Donessle Dr, Oakville
$2,998,000 CAD
2 baths
4 beds
Donessle Dr
( )
21.51778 BTC
Welcome to 214 Donessle Drive. This lovely 2-storey, 4 bedroom home is located on a family friendly street in prestigious Old Oakville and sits on a 67 x 174ft lot. This spacious home has an excellent floor plan for family living and entertaining. The eat in kitchen...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
21 Second St, Oakville
$4,999,000 CAD
2 baths
3 beds
Second St
( )
35.87971 BTC
RIPARIAN WATERFRONT IN DOWNTOWN OAKVILLE. Potential abounds! Fantastic opportunity to renovate, or build a new custom home. The possibilities are endless in this secluded waterfront residence where location and privacy are second to none. Charming main floor offers a...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
302 William St, Oakville
$3,299,000 CAD
3 baths
5 beds
William St
( )
23.67817 BTC
Welcome to 302 William Street in the heart of downtown Oakville. This classic red-brick home is steeped in character and warmth. Lovingly cared for and updated over the past 54 years by the current owners, it has beautiful gardens and mature trees. This home has over 2...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
415 Queen Mary Dr, Oakville
$1,650,000 CAD
3 baths
2+1 beds
( )
11.84267 BTC
***Absolutely Immaculate***This stunning rebuild by a high-end Oakville custom builder offers a unique, exquisitely appointed home for downsizers and small families!! Exceptional detailing includes coffered 9-ft ceilings, millwork and Wainscotting throughout! The...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
112 Elton Park Rd, Oakville
$6,999,999 CAD
8 baths
4+1 beds
Elton Park Rd
( )
50.24163 BTC
Presenting This Resplendent Custom Masterpiece Located In SE Oakville Showcasing a Flawless Contemporary Design w/ Close Proximity To Lakeside Parks & All Desired Amenities. The Immaculate Interior Embodies a Luxurious Experience Spanning Over 7,426 SF Total. Down The...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
377 Tudor Ave, Oakville
$2,838,000 CAD
6 baths
4+1 beds
( )
20.36940 BTC
Welcome to the lifestyle youve been waiting for in the exclusive Royal Oakville Club, a prestigious community in West Oakville. Walk to restaurants, shops, downtown, Oakville Harbour, & Lake Ontario. Close to top-rated schools & to highways & the GO station for...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
144 Stewart St, Oakville
$2,599,000 CAD
5 baths
3+1 beds
( )
18.65400 BTC
Welcome To 144 Stewart St, A Brand New Custom Built Home In the Heart Of Kerr Village. This Exquisite Residence Is Just A Short Walk From Lake Ontario, Offering The Perfect Blend Of Luxury &Location. Built With Superior Craftsmanship & Meticulous Attention To Detail...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
24 Raymar Pl, Oakville
$5,700,000 CAD
5 baths
4+2 beds
Raymar Pl
( )
40.91105 BTC
Stately residence at the bottom of an exclusive cul de sac, one house away from the Lake and steps to Downtown Oakville. Over 8000 sqft total space, including 5293 main & second floor, plus 902sqft heated & enclosed outdoor space. Extensively renovated by Cochren Homes...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
1044 Argyle Dr, Oakville
$12,495,000 CAD
3 baths
3+1 beds
Argyle Dr
( )
89.68132 BTC
Epic waterfront lot!! This is the opportunity that you have been waiting for to build your dream home. One of the last remaining developable Lakefront lots that are walking distance to downtown Oakville! This stunning .54 acre waterfront lot has Riparian rights with...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
233 Lakewood Dr, Oakville
$7,988,000 CAD
5 baths
4+1 beds
Lakewood Dr
( )
57.33289 BTC
Located close to the shores of Lake Ontario in South Central Oakville, on the picturesque cul-de-sac Lakewood Drive, this brilliant David Smalls designed home will captivate your senses. This 4+1 bedroom, 4+1 bathroom home offers over a total 6,500 sqft. of quiet...
Book Showing
Request More Info
Send Text Message
Call: 416-800-1055
1 2 Next
Old Oakville Real Estate
Oakville has always been the core of activity, even as far back as the early 18th Century when it was established by William Chisholm, his son and brother in law. Sailors and merchants were drawn to the shores of Lake Ontario & Oakville Harbour for the flurry of activity from shipbuilding, timber exporting and farming products. The town of Oakville was becoming known for its participation in the underground railroad that aided African Americans to escape into Canada. The Grand Trunk Railway was built as a means of exporting what later became the major industry of Oakville…basket making. The new heights of successful business in Oakville drew the attention of major manufacturers who did not waste time developing an industrial area to plant their manufacturing factories and offices. It was in 1962 when Oakville merged together with a part of Trafalgar Township, Palermo, Bronte & Sheridan, it became the new and improved Town of Oakville. Communities within Oakville are: West Oak Trails, Old Oakville, Uptown Core, College Park, Kerr Village, River Oaks, Bronte, Palermo, Eastlake, Glen Abbey, Clearview, Iroquois Ridge South and Iroquois Ridge North. Part of the Greater Toronto Area, Oakville is considered a suburban town (full of residual 18th Century charm & architecture and enticing modern elements).
Oakville real estate for sale is unlike anything any home buyer has indulged in before. Condos and executive homes with waterfront views, semi-detached townhomes and detached houses that edge nature and their fitness trails, makes Oakville one of the best places in Ontario to invest. Family-friendly neighbourhoods with everyday amenities are part of the enticing factors of Oakville properties for sale. There are 22 public elementary schools, 6 public secondary schools, 18 French Immersion schools, Appleby College and Sheridan College. Transportation to, through and out of Oakville is possible with Oakville Transit public services that do connect with GO Transit services (with stations in both Bronte and Oakville), the Highway 403, the 407 ETR Highways and the Queen Elizabeth Way. Oakville station also has Via Rail services for travel between Windsor & Quebec. The real estate market coupled with the amenities and ease of transportation, over 300 national and international businesses have made Oakville their ‘go to’ premium location to set up shop involving numerous industries. Access to prime property, a highly skilled workforce and in-depth training advancements makes business launches in Oakville successful.
With over 140 parks, wooded areas, wharfs, gardens, squares, promenades, bluffs and beaches around Oakville, there is no shortage of outdoor enjoyment for the whole family locally. Trails through and around Oakville are also abundant, in the east there is the Winston Woods Trail, Joshua’s Creek Trail (Joshua’s Valley, Bayshire Woods Park, Avonhead Ridge Trail, East Joshua Creek Trail, Kingsford Gardens, Sheridan Valley Park Trail & Iroquois Shoreline Woods Trail), Morrison Valley North & South Trails, Crosstown Trail (east & west). In central Oakville is the Nipegon Trail, McCraney Valley Trail, Munn’s Creek Trail, Shannon Creek Trail, Sixteen Mile Creek Trail (3 sections – West Bank Trail, Inner Valley Trail & East Bank Trail). The waterfront provides the Larry Cain Trail. In the western area of Oakville is the Glen Abbey Trail System & West Oak Trails (Upper Middle Road Trail, Arbourview Trail, Taplow Creek Trail, Bray’s Trail, Old Abbey Trail, Birchtree Trail, McCraney Creek Trail, Dorval Trail, Indian Ridge Trail, Colonial Williams Trail, Glen Oak Creek Trail and East Fourteen Mile Creek Trail). The Bronte area unfolds many trails to explore as well (another Waterfront Trail, Bronte Creek Trail, Nautical Wood Park & Village Woods Park Trails, Sheldon Creek Trail and Donovan Bailey Park Trail).
The Harbours and marinas (Bronte Harbour and Oakville Harbour) are highly enjoyable by both residents and visitors. The quite extensive shorelines of Lake Ontario open up plenty of recreational bustle (power boating, sail boating, nautical-related facilities, shops, restaurants and heritage elements). History, heritage, culture and the arts are a staple in the lives of those who live and play in Oakville. The Erchless Estate/Gardens & Grounds, The Custom House, The Thomas House, Oakville Centre for the Performing Arts, CommUnity Arts Space, Oakville Galleries and the Oakville Museum all are the place to visit for those who wish to immerse themselves with the rich backstory to current day of Oakville. Shopping at the Oakville Place Shopping Centre is a unique experience with all of its offerings. Some of the memorable festivals and events that take place in Oakville include: The Downtown Oakville Jazz Festival (summertime), the For the Love of the Arts Festival (early Springtime), Midnight Madness (July) and the Oakville Family Ribfest (June). Farm fresh foods, crafts and locally made baked goods are just the beginning at some of the festivals and fairs, games, rides and exhibits are also abundant. Golfers will be able to enjoy the Glen Abbey Golf Course and sports enthusiasts can delight in the numerous soccer, lacrosse, swimming, rugby, fitness centers, hockey, skating, basketball, baseball and canoeing venues.
Are You a Licensed Real Estate Agent or Broker?
© 2011-2025 Real Estate Bay Realty Inc, Brokerage
The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate and may not be used for any commercial or any other purpose. Information is deemed reliable but is not guaranteed accurate by TREB, Listing.ca or Real Estate Bay Realty, Brokerage.
The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.
Real Estate Bay Realty, Brokerage
220 Duncan Mill Road, Suite 209
Toronto, ON M3B 3J5
Phone: 416-800-1055
info@listing.ca
Listing.ca on Twitter
RealEstateBay.ca on Facebook