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Old Oakville MLS® Listings

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95 Bel Air Dr, Oakville
$5,519,800 CAD
5 baths
3+2 beds
( )
41.41181 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...
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214 Donessle Dr, Oakville
$2,998,000 CAD
2 baths
4 beds
Donessle Dr
( )
22.49223 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...
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179 Douglas Ave, Oakville
$4,598,000 CAD
5 baths
4+1 beds
Douglas Ave
( )
34.49609 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...
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152 Elton Park Rd, Oakville
$4,450,000 CAD
4 baths
4+1 beds
Elton Park Rd
( )
33.38573 BTC
Walking Distance To Top Local Schools, Go Train And Lake! Rarely Do We See Such A Great Blend Of Home, Land And Location. The Traditional Circular Drive Opens To A Timeless All-Stone Exterior Welcoming You To What Is Truly A Coveted Find On One Of The Most Desirable...
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117 Watson Ave, Oakville
$2,998,000 CAD
3 baths
3+1 beds
Watson Ave
( )
22.49223 BTC
Welcome to 117 Watson Avenue, a rare gem in old Oakville, where you have the unique opportunity to choose your ideal living situation. This charming bungalow, known as "A Hobbit Hollow," sits on a hard-to-find 75x150 lot, providing two exceptional options for your...
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214 Waneta Dr, Oakville
$3,149,000 CAD
5 baths
4 beds
Waneta Dr
( )
23.62509 BTC
This charming, high-end custom-built family home, set on a 75-foot front lot, is located in the heart of Oakville, just steps from the lake, Appleby College, Old Oakville's downtown, restaurants, and shopping. Featured on HGTV and built by TV personality Bryan Baeumler...
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214 Lakewood Dr, Oakville
$2,199,000 CAD
3 baths
3+1 beds
Lakewood Dr
( )
16.49780 BTC
Beautiful 3 plus 1 bedroom raised bungalow available in the West Harbour community of Downtown Oakville. South of Lakeshore rd. Steps to Lake Ontario, harbour, downtown Oakville. Quiet area nestled in mature trees and surrounded by new luxury homes. Tastefully...
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234 Maurice Dr, Oakville
$3,888,000 CAD
7 baths
4+1 beds
Maurice Dr
( )
29.16938 BTC
Designed By Award Winning Architect Steve Hamelin, Custom Built Home Crafted with Timeless Finishes Located in the Prestigious Old Oakville Neighborhood. Rarely Offered Sitting on 60 Ft X 160 Ft Prime Pool Sized Lot! Just Steps To Kerr Village, Dt Oakville, Lakefront...
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377 Tudor Ave, Oakville
$2,778,900 CAD
6 baths
4+1 beds
Tudor Ave
( )
20.84845 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...
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144 Stewart St, Oakville
$2,588,000 CAD
5 baths
3+1 beds
Stewart St
( )
19.41624 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...
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112 Elton Park Rd, Oakville
$6,999,999 CAD
8 baths
4+1 beds
( )
52.51687 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...
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2110 Blyth Cres, Oakville
$7,250,000 CAD
8 baths
5+1 beds
Blyth Cres
( )
54.39248 BTC
Discover luxury & comfort in this exquisite new 2024 David Small Designed home in coveted Southeast Oakville. Spread across a generous 4,275 sqft, this architectural gem offers state-of-the-art living in a peaceful setting where tranquility & elegance fuse seamlessly...
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415 Queen Mary Dr, Oakville
$1,650,000 CAD
3 baths
2+1 beds
Queen Mary Dr
( )
12.37898 BTC
***Absolutely Immaculate***This stunning high-end custom renovation/enlargement offers a unique, exquisitely appointed home for downsizers and small families!! Exceptional detailing includes coffered 9-ft ceilings, millwork and Wainscotting throughout! The kitchen is...
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55 Stewart St, Oakville
$875,000 CAD
1 baths
3 beds
( )
6.56461 BTC
*Opportunity Knocks*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 Conveniently Located In The Heart Of It All*Walking Distance To Downtown Shops...
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302 William St, Oakville
$3,299,000 CAD
3 baths
5 beds
William St
( )
24.75046 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...
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169 Maurice Dr, Oakville
$3,450,000 CAD
11 baths
7+4 beds
( )
25.88332 BTC
This well-maintained 11-unit apartment building presents a prime investment opportunity, featuring a balanced mix of 7 two-bedroom units and 4 one-bedroom units, catering to a diverse range of tenants. The property has undergone significant upgrades, including a new...
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416 Trafalgar Rd, Oakville
$3,599,000 CAD
4 baths
2+2 beds
Trafalgar Rd
( )
27.00118 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 (2022) character home charms w/ its riverside locale & riparian privileges along 16 Mile Creek. This 4BED, 3.5BATH RES offers LUX...
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509 Lakeshore Rd, Oakville
$2,998,888 CAD
2 baths
2 beds
Lakeshore Rd
( )
22.49889 BTC
This prime mixed-use property offers incredible potential in a prestigious, high-traffic location. The main floor currently operates as a convenience store, benefiting from its proximity to Appleby College with over 800 students, creating a built-in customer base. The...
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319 Macdonald Rd, Oakville
$2,410,000 CAD
3 baths
3 beds
Macdonald Rd
( )
18.08081 BTC
Prime Investment & Redevelopment Opportunity in Old Oakville. Exceptional 61' x 147' lot in prestigious Old Oakville, surrounded by high-end custom homes. Ideal for developers, investors, or families, the RL3-0 zoning with 35% lot coverage offers flexibility to design...
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331 Macdonald Rd, Oakville
$4,595,000 CAD
5 baths
4+1 beds
( )
34.47358 BTC
Located in one of Oakville's most desirable pockets this new custom home creates a stylish atmosphere that will impress even the most detailed buyer. Architecture by Hicks Design Studio and built by Gasparro Homes this home features over 3,100 square feet above grade...
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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.
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