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Old Oakville MLS® Listings

(42)
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3 Ennisclare Dr, Oakville
$16,000,000 CAD
4 baths
5 beds
( )
- BTC
One of the last remaining developable Riparian Lakefront estates in South East Oakville boasting unrivalled and expansive views of Lake Ontario from Downtown Toronto to the Niagara Escarpment. With 184ft of lake frontage and boat access and with a total of 3.63 acres...
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230 Weybourne Rd, Oakville
$2,000,000 CAD
3 baths
4+1 beds
Weybourne Rd
( )
- BTC
Welcome to this lovely 4+1 bedroom family home situated on a quiet and child-safe court just steps from Downtown, Kerr Village, Appleby College, and renowned schools. This home has been meticulously updated, showcasing on-site finished hardwood floors, solid doors with...
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420 Randall St, Oakville
$5,200,000 CAD
5 baths
6 beds
Randall St
( )
- BTC
Situated in Old Oakville and surrounded by large mature trees, this is a rare offering for those who appreciate a warm living space with historical detail in turnkey condition. This home has undergone a complete transformation having been completely renovated...
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260 Robinson St, Oakville
$1,699,000 CAD
0 baths
0 beds
Robinson St
( )
- BTC
Prime Value Add & Development Opportunity in the heart of Oakville. Zoned RM1 with drawings available for a multifamily development or a single family residence designed by Gren Weis (4500 Sq Ft). Prime Location, and steps away from Downtown Oakville and Lakeshore...
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431 River Side Dr, Oakville
$2,488,000 CAD
4 baths
3+1 beds
River Side Dr
( )
- BTC
Situated on a stunning ravine lot this fully renovated central Oakville family home has 3+1 bedrooms and 3.1 baths. An award-winning front and backyard oasis was created by ProScape Land Design in 2022 including a new driveway, full irrigation system, fire pit, hot tub...
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283 Douglas Ave, Oakville
$2,999,000 CAD
4 baths
3+1 beds
Douglas Ave
( )
- BTC
Welcome to 283 Douglas Avenue, a prestigious picture-perfect street with soaring trees, walking distance to the lake in SE Oakville. The million-dollar view from the family room addition features floor-to-ceiling windows showcasing an outdoor oasis complete w/pool and...
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55 Chisholm St, Oakville
$4,990,000 CAD
4 baths
3+1 beds
Chisholm St
( )
- BTC
For the discerning few, step into a realm of unparalleled luxury and sustainability at 55 Chisholm St, Oakville. Nestled in West Harbour, steps to the lake access of Tannery Park, and magical Downtown Oakville, this iconic residence seamlessly blends old-world elegance...
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398 Lakeshore Rd, Oakville
$4,750,000 CAD
5 baths
4+1 beds
Lakeshore Rd
( )
- BTC
Nestled in one of Oakville's most prestigious neighborhoods, this impressive 5,600 square foot home offers a unique blend of tranquility and luxury just 600 meters from the shores of a beautiful lake. Surrounded by lush landscaping and facing south towards the calming...
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232 Slater Cres, Oakville
$1,399,000 CAD
2 baths
3+1 beds
Slater Cres
( )
- BTC
Housemate moves to Europe at end of May and home will be solely owner occupied June 1. Beautiful sidesplit on a quiet crescent in the high demand (south of QEW) neighbourhood of Kerr Village. Walk to the lake, downtown & cafes along Kerr St. Easy access to the highways...
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67 Raymar Pl, Oakville
$2,898,000 CAD
3 baths
3 beds
Raymar Pl
( )
- BTC
Custom built with main floor Primary suite by Cochren Homes & Gren Weis Architect in 1985 & updated in 2022. This move-in ready home is ideal for the down-sizer or small family within walking distance to top schools, the lake and downtown Oakville. Generous floor plan...
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312 Mary St, Oakville
$1,449,900 CAD
2 baths
3+1 beds
Mary St
( )
- BTC
Nestled in the heart of West Oakville, Situated in a family-friendly neighborhood. Inside, you'll find an inviting eat-in kitchen, and a separate living room for entertaining. This home offers three bedrooms, plus an additional room that can serve as a fourth bedroom...
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143 Balsam Dr, Oakville
$4,750,000 CAD
4 baths
5 beds
Balsam Dr
( )
- BTC
Rare offering of a lush, private 102' x 296' lot (approx 0.7 acre) on coveted street in SE Oakville, close to downtown shops & restaurants. Build or enjoy as is! Long, meandering drive leads to existing family home of approx. 3,140 sq ft. Featuring 5 bedrooms and 4...
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199 Chartwell Rd, Oakville
$11,995,000 CAD
7 baths
4+1 beds
Chartwell Rd
( )
- BTC
Magnificent gated estate on a meticulously landscaped 3/4 acre lot, on Oakville's coveted ' Street of Dreams'. This Architectural monument was designed & Built by one of the World's most renowned master builders of uber-luxury residences. Solid limestone construction...
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124 Chisholm St, Oakville
$1,849,900 CAD
2 baths
2 beds
( )
- BTC
Own a piece of history while enjoying the best lifestyle Oakville has to offer! Walking distance to downtown Oakville, the Oakville Centre of the Performing Arts, Lake Ontario and the Oakville Club, this location can't be beat. This 2 bed 2 bath residential/commercial...
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224 Weybourne Rd, Oakville
$1,949,900 CAD
2 baths
4 beds
( )
- BTC
This 4-lvl side split is beautiful inside & out situated at the end of a quiet court in sought-after S/W Oakville. Newer front door leads to main lvl w/ living rm, dining rm & kitchen offering storage w/ pot drawers & pantry. Recently installed (22) hardwd stairs...
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128 Balsam Dr, Oakville
$7,798,000 CAD
10 baths
5+2 beds
( )
- BTC
Welcome to 128 Balsam Drive in South East Oakville, One of the Prettiest, Most Exclusive and Desirable Streets in the Greater Toronto Area!This Extraordinary Custom Built Homes is just steps to Oakville's Historic Downtown Shopping District, Plethora of Private Schools...
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234 William St, Oakville
$3,500,000 CAD
4 baths
4 beds
William St
( )
- BTC
RARE opportunity to live right in the heart of Old Oakville! A charming brick home with ample parking, just steps to downtown Oakville and Lake Ontario. With over 4500 square feet of living space, this home has a fantastic floor plan for todays family. As you enter the...
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298 River Side Dr, Oakville
$3,100,000 CAD
4 baths
4+1 beds
( )
- BTC
Experience the unique charm of this well-maintained bungalow loft, situated in one of Oakville's most sought-after neighborhoods! Boasting a perfect blend of comfort, style, and convenience, this delightful home is the ideal choice for your next move. The main floor...
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150 Dianne Ave, Oakville
$3,550,000 CAD
3 baths
3+1 beds
Dianne Ave
( )
- BTC
Live In/Reno/New-build/Landbank Opportunity. A livable/rentable charming traditional family home nicely positioned on a large 16,081 square foot lot in the much-desired Morrison neighbourhood of south east Oakville. Within walking distance to Lake Ontario + renowned...
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220 Reynolds St, Oakville
$3,000,000 CAD
5 baths
4+1 beds
Reynolds St
( )
- BTC
Fabulous Family Home In Old Oakville Perfect For Extended Family. Entertainer's Dream Backyard With Salt Water Pool, Patio And Shed, Elegant Hardwood Flooring And Staircases Throughout, In-Law/Nanny Suite And Rec Room In Finished Basement, Large Eat-In Kitchen With S/S...
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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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