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Old Oakville MLS® Listings

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319 Macdonald Rd, Oakville
$2,578,000 CAD
3 baths
3 beds
( )
- BTC
Prime Redevelopment Opportunity in the Heart of Old Oakville! This 61' x 147' lot, located in the highly desirable Old Oakville neighborhood, offers an exceptional opportunity for builders and investors. Surrounded by luxury custom homes and high-end redevelopment...
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233 Lakewood Dr, Oakville
$7,988,000 CAD
5 baths
4+1 beds
Lakewood Dr
( )
- 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...
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279 Macdonald Rd, Oakville
$2,498,000 CAD
2 baths
4 beds
( )
- BTC
Fabulous renovation opportunity in prime Old Oakville. Original C.1912 brick 2 1/2 storey residence with dreamy front porch. Located mid-block and in an elevated position on this exceptionally bright and quiet property measuring 60' x 192' and over 11,500 Square Feet...
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64 Brentwood Rd, Oakville
$8,499,000 CAD
9 baths
4+1 beds
Brentwood Rd
( )
- BTC
Incredible custom-built home situated on a beautiful 100 x 162' lot with desirable SW exposure steps from the lake on one of Southeast Oakville's most coveted streets. The house is Michael Pettes designed and PCM built and offers incredible and hard to replicate...
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18 Holyrood Ave, Oakville
$6,250,000 CAD
5 baths
3 beds
Holyrood Ave
( )
- BTC
Discover the epitome of waterfront living on Holyrood Avenue in Oakville. This stunning home offers over 5,500 sqft of living space with a blend of serene lakeside charm and modern elegance. Nestled in a close-knit community on a quiet cul-de-sac surrounded by...
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76 Brock St, Oakville
$2,445,000 CAD
4 baths
4 beds
Brock St
( )
- BTC
Beautiful home located in one of Oakville's sought after neighborhood. This property is south of Lakeshore with close proximity to the Lake. Nestled in a serene family friendly neighborhood with a blend of natural beauty, upscale living and convenient accesss to...
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280 Balsam Dr, Oakville
$6,495,000 CAD
7 baths
4 beds
Balsam Dr
( )
- BTC
Welcome to an Extraordinary Custom-Built Masterpiece in Downtown Oakville. Step into unparalleled luxury with this stunning custom-built sidesplit, just moments away from the vibrant downtown Oakville and the serene lakefront. Spanning over 6,600 square feet of...
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27 Park Ave, Oakville
$11,000,000 CAD
9 baths
4+1 beds
Park Ave
( )
- BTC
Welcome to 27 Park Avenue, nestled in the prestigious Orchard Beach community of Old Oakville, where the allure of the Hamptons meets the tranquility of Lake Ontario. Crafted by renowned architect Gus Ricci with handpicked finishes by Studio H, this estate spans over...
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200 William St, Oakville
$3,250,000 CAD
3 baths
5 beds
William St
( )
- BTC
Well positioned property in historic Old Oakville, south of Lakeshore, just steps to the beach, Oakville harbour and Town Square. Sitting proudly up on a rise, this 2 1/2 storey home features wonderful views, light and plenty of space to create your dream home. With...
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50 Burnet St, Oakville
$2,499,000 CAD
3 baths
4 beds
Burnet St
( )
- BTC
Location! Location! Live in the Highly Coveted "West Harbour" Neighborhood steps to Downtown Oakville, Tannery Park & Kerr Village. This Charming, Beautifully Renovated 4-bedroom, 3-bathroom home showcases over $200K in renovations, including a remodel by Gren Weis...
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235 Lakewood Dr, Oakville
$4,999,998 CAD
6 baths
3+2 beds
( )
- BTC
Located in coveted West Harbour, come discover tranquility and elegance at 235 Lakewood Drive. Nestled on a generous .56-acre lot, embraced by majestic foliage in a private cul-de-sac, this residence epitomizes serene living mere steps from the lake. Crafted by...
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397 Trafalgar Rd, Oakville
$2,774,900 CAD
4 baths
4 beds
Trafalgar Rd
( )
- BTC
Stunning Century Home with modern conveniences on an expansive lot in Old Oakville. Think about the possibilities of subdividing this oversized lot! Dating back to the early 1920's, you will find enduring charm & elegance. Featuring original architectural details...
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316 Pinegrove Rd, Oakville
$1,629,000 CAD
4 baths
4+1 beds
Pinegrove Rd
( )
- BTC
This charming Family home, in the heart of central South Oakville, provides on-the-go easy access to all that this wonderful community has to offer. Updated extensively in recent years & spacious and comfortable throughout, other features include living, dining, and...
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1044 Argyle Dr, Oakville
$12,995,000 CAD
3 baths
3+1 beds
Argyle Dr
( )
- 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 125...
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24 Raymar Pl, Oakville
$5,850,000 CAD
5 baths
4+2 beds
Raymar Pl
( )
- 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...
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55 Stewart St, Oakville
$939,000 CAD
1 baths
3 beds
Stewart St
( )
- 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...
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192 Waneta Dr, Oakville
$2,399,000 CAD
4 baths
4 beds
Waneta Dr
( )
- BTC
Step into this extraordinary custom-built home on a tranquil crescent, just minutes from Lake Ontario, Appleby College, and downtown Oakville. Combining timeless elegance with modern updates, this property offers a refined luxury living style and exceptional potential...
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282 Tudor Ave, Oakville
$3,999,000 CAD
6 baths
4+1 beds
Tudor Ave
( )
- BTC
Welcome to The Royal Oakville Club (ROC), an exclusive enclave of homes situated in the heart of beautiful downtown Oakville. This 4,062 square foot, 4-bedroom home, with each bedroom featuring an ensuite bathroom, is situated on a premium lot and has been upgraded...
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279 Macdonald Rd, Oakville
$2,498,000 CAD
2 baths
4 beds
( )
- BTC
Fabulous renovation opportunity in prime Old Oakville. Original C.1912 brick 2 1/2 storey residence with dreamy front porch. Located mid-block and in an elevated position on this exceptionally bright and quiet property measuring 60' x 192' and over 11,500 Square Feet...
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396 River Side Dr, Oakville
$1,999,000 CAD
6 baths
4+2 beds
River Side Dr
( )
- BTC
Nestled in the peaceful and charming community of South Oakville, this stunning modern home is surrounded by the serene 16 Mile Creek while being just a short walk to downtown. Enjoy the perfect blend of countryside tranquility and urban convenience. Rebuilt in 2022...
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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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