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Old Oakville

Home Cost

$1,107,200

Average Family Income

$705,865

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About Old Oakville

Old Oakville is the original settlement of the area dating back to the 1800’s, and the historic buildings and grandiose waterfront mansions create an impressive visual punch. This is luxury at its finest, and this is probably Oakville’s most expensive and most desirable area.

Who Lives Here

There is plenty of old money in Old Oakville, and you’ll find lots of affluent families with kids, as well as many empty nesters and seniors. There’s also an influx of young professionals populating those condos and town homes. This is a very popular area, and those who can afford it absolutely adore it.

What's Great About It?

As with most of Oakville, there’s a beautiful waterfront and refreshing greenery at every turn. What’s unique about this area, however, is that historic feel throughout much of it—something noticeably different from the newer areas in Oakville. There’s a unique charm that continues to appeal to people. Go for a stroll and you’ll see for yourself!

Schools

St. Vincent Elementary (JK-Gr 8)
St. Joseph Elementary (Gr 5-8) (Fr. Imm.)
St. Thomas Aquinas Secondary (Gr 9-12) (Fr. Imm.)
Maple Grove Elementary (JK-Gr 8)
New Central Elementary (JK-Gr 6)
E.J. James Elementary (Gr. 1-8) (Fr. Imm.)
Oakville Trafalgar Secondary (Gr 9-12) (Fr. Imm.)

Many of Old Oakville’s affluent residents choose to send their children to one of the many surrounding private schools such as MacLachlan College, Dearcroft Montessori, St. Mildred’s-Lightbourn School, West Wind Montessori Jr. High School, and Appleby College.

Homes for sale in Old Oakville

Looking for listings in Old Oakville for sale? You’re only seeing some of the listings available here. To see them all, just click the ‘Signup’ or ‘Login’ links below.

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We have found a total of 131 listings, but only 89 are available for public display. To get instant access to all 131 listings, please .
1-12/89
  • 489 Lakeshore Road E in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8183300

    489 Lakeshore Road E Old Oakville Oakville L6K 1G4
    Main Photo: 489 Lakeshore Road E in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8183300
    $27,850,000
    Freehold
    Status:
    Active
    MLS® Num:
    W8183300
    Bedrooms:
    5
    Bathrooms:
    8
    Welcome to 489 Lakeshore Road East, a truly rare and exceptional estate crafted by the renowned Ferris Rafauli, nestled in the prestigious enclave of southeast Oakville along the serene shores of Lake Ontario. This rare one-acre property boasts a remarkable 16,000+ square foot steel-frame home, meticulously designed to showcase unparalleled craftsmanship and timeless elegance. Every detail of this exquisite residence speaks to a dedication to luxury living, from its concrete structure to its five bedrooms and eight baths, eight fireplaces, three kitchens, and elevator for seamless access to all levels. Indulge in the ultimate relaxation with amenities such as a Versace inspired indoor pool, built-in spa and gym, dry sauna, and cabana with a full kitchen. The property also features a four-car garage, 600-amp electrical service, in-floor heating, and cutting-edge building operation systems, all complemented by award-winning landscaping. More details
    Listed by ENGEL & VOLKERS TORONTO CITY
    Tanya Crepulja
    Steven Fontes
  • 199 Chartwell Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8217968

    199 Chartwell Road Old Oakville Oakville L6J 3Z7
    Main Photo: 199 Chartwell Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8217968
    $11,995,000
    Freehold
    Status:
    Active
    MLS® Num:
    W8217968
    Bedrooms:
    5
    Bathrooms:
    7
    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, slate rf, copper eaves & stone pillars. 11,000 + sq ft of exq finishes t/o incl walls & ceilings, exotic woods, imported marbles, features inc cstm elevator,2 storey Grt Rm w 24 ft 2 sided limestone f/p open to stately Library .Chef's dream kit w ebony & walnut cabinetry, marble counters & serving pantry. Frml Din Rm o/l front gardens. 2nd lvl w Grand Prim retreat w lavish 6 pc ensuite & boutique-style Dressing Rm, 3 addtnl beds w lux ensuites & opulent LA Rm. LL w 5th bed, 2 baths, hm office, s/o/t/a hm thtr, gym, Recreation area, wet bar & wine Rm. Resort-style b/yrd w inground salt-water pool w cascading jets, wtfl spa, fire bowls, linear f/p, stone decking & gorgeous Cabana!! Steps to lake & town. Exc school distict! More details
    Listed by SOTHEBY`S INTERNATIONAL REALTY CANADA
    Tanya Crepulja
    Steven Fontes
  • 26 Trafalgar Road in Oakville: Old Oakville House (3-Storey) for sale : MLS®# W8191522

    26 Trafalgar Road Old Oakville Oakville L6J 3E7
    Main Photo: 26 Trafalgar Road in Oakville: Old Oakville House (3-Storey) for sale : MLS®# W8191522
    $9,998,000
    Freehold
    Status:
    Active
    MLS® Num:
    W8191522
    Bedrooms:
    6
    Bathrooms:
    9
    Nestled at the base of Trafalgar Road, in the heart of Old Oakville, this home boasts an impressive Walk Store of 94 out of 100. With lake front access, steps to lakefront trails, parks, the marina, boutique stores and fine dining. This expansive property boasts dimensions of 155 by 104 ft., and offers a sweeping vista of the ever-changing lake, endless horizons, and magnificent sunrises. Steeped in a rich history, the house has undergone a transformation into a stunning residence spanning 10,000 sq. ft. across three levels. With 4 bedrooms and an additional 2, totaling 6beautifully appointed bedrooms, and a generous 9 bathrooms, this home exudes refined luxury .Step inside to discover a custom kitchen seamlessly blending classic charm modern convenience. Luxurious amenities abound, from the elevator to the lofty ceilings adding grandeur, a captivating walk-in wine cellar, a walk-out basement ,an expansive area for a nanny or in-law suite, a well-equipped gym and a loft. More details
    Listed by CENTURY 21 LEADING EDGE REALTY INC.
    Tanya Crepulja
    Steven Fontes
  • 210 Chartwell Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8086756

    210 Chartwell Road Old Oakville Oakville L6J 3Z8
    Main Photo: 210 Chartwell Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8086756
    $9,998,000
    Freehold
    Status:
    Active
    MLS® Num:
    W8086756
    Bedrooms:
    4
    Bathrooms:
    6
    Exceptional Californian inspired Custom rebuild on one of Oakvilles most sought-after streets. Modern Luxury awaits you at 210 Chartwell road.Gren Weis contemporary interior design and architecture along with Mazengas craftsmanship, created over 7500 sf of spectacular living space offering the perfect entertainers home. Chefs' kitchen with double islands and oversized walk-in pantry, living and dining room with 18ft ceilings, all with floor to ceiling windows. Upstairs offers 3 large bedrooms, all with ensuites and upper level living room. Built on an expansive 102 x 235lot with tiered manicured gardens, gunite saltwater pool and hot tub, custom fountain, and year-round turf grass. Ideally located, just a walk to Downtown Oakville. More details
    Listed by RE/MAX ABOUTOWNE REALTY CORP.
    Tanya Crepulja
    Steven Fontes
  • 511 Macdonald Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8156614

    511 Macdonald Road Old Oakville Oakville L6J 2B7
    Main Photo: 511 Macdonald Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8156614
    $7,950,000
    Freehold
    Status:
    Active
    MLS® Num:
    W8156614
    Bedrooms:
    5
    Bathrooms:
    7
    A Visionary Architectural Concept Focused On Hosting And Gatherings Is Showcased In This Beautiful Property, Characterized By Meticulous Attention To Detail & Craftsmanship, Seamless Continuity, Minimalist Aesthetics, And Distinctive Artisanal Finishes That Flow Effortlessly Throughout The Spacious Open Floor Plan And Into The Bespoke Kitchen. The Dining Area And Family Room Are Enveloped By Modern Floor-To-Ceiling Glass Doors That Elegantly Retract, Seamlessly Blending Indoor And Outdoor Living Spaces. An Arresting Curved Staircase Adds To The Visual Allure. The Primary Bedroom, Reminiscent Of A Luxurious Spa, Exudes A Hotel-Inspired Ambiance With Stylish Features. The Spacious Lower Level Offers A Range Of Entertainments, Including A Rec. Room, Billiards Area, Fitness Studio, And Theatre. 3 Indoor Fireplaces, Outdoor Fire Pit And Fireplace.Thoughtful Landscaping Enhances The Property's Privacy Plus Pizza Oven To Enjoy. Minutes To Downtown Restaurants, Shops, Entertainments And More! More details
    Listed by FORESTWOOD REAL ESTATE INC.
    Tanya Crepulja
    Steven Fontes
  • 128 Balsam Drive in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8209234

    128 Balsam Drive Old Oakville Oakville L6J 3X5
    Main Photo: 128 Balsam Drive in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8209234
    $7,798,000
    Freehold
    Status:
    Active
    MLS® Num:
    W8209234
    Bedrooms:
    7
    Bathrooms:
    10
    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 and Plenty of Waterfront Parks. This Gorgeous Home Boots Over 7,500 sf of Luxurious Living Space on a Generous 100x152" Lot. The Main Floor Is an Entertainer's Dream! Offering a Hollywood Style Kitchen with Wolf Stove, A Massive Centre Island Equipped with 2 Sinks and Plenty of Sitting space, Open Concept to Family Room and Breakfast Area All which Overlook the Lovely Backyard. This Home has 7 Bedrooms Each with it's own Personal Ensuite, 9 Bathrooms, 5 Gas Fireplaces, a Beautiful Walnut Wine Cellar and MUCH more! This Home was Built with All the Comforts and Luxuries in mind. More details
    Listed by RE/MAX ESCARPMENT REALTY INC.
    Tanya Crepulja
    Steven Fontes
  • 200 Chartwell Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8009782

    200 Chartwell Road Old Oakville Oakville L6J 3Z8
    Main Photo: 200 Chartwell Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8009782
    $6,995,000
    Freehold
    Status:
    Active
    MLS® Num:
    W8009782
    Bedrooms:
    5
    Bathrooms:
    7
    Exceptional gated estate home nestled on a spectacular 100' x 225' lot on Oakville's most coveted street of dreams, completely reconstructed in 2020 with over 7500 sf luxury finished living space on trend finishes & manicured gardens with the timeless character and curb appeal. The main level boasts airy kitchen w/ finest cabinetry opens to a spacious family room that's meticulously designed for entertaining, the office, formal living room, piano lounge and 3 season screened Muskoka room.Luxuriate in the principal suite w/linear gas fireplace, dual ensuites, separate walk-in closets & a boutique-like dressing room.Private walk out balcony overlooks the private Muskoka like yard with towering trees. All 3 additional upper level bedrooms each have private en-suites and generous closets.Take the main floor slide or the stairs to a fully finished lower level with recreation, games rooms, gym, 5th bdrm, full bathroom & plenty of storage.2 laundry rooms provide optimal laundry efficiency. More details
    Listed by RE/MAX HALLMARK ALLIANCE REALTY
    Tanya Crepulja
    Steven Fontes
  • 177 Gloucester Avenue in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8053260

    177 Gloucester Avenue Old Oakville Oakville L6J 3W3
    Main Photo: 177 Gloucester Avenue in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8053260
    $6,250,000
    Freehold
    Status:
    Active
    MLS® Num:
    W8053260
    Bedrooms:
    6
    Bathrooms:
    8
    Nestled in Old Oakville, this exceptional home stands on a 0.581-acre lot. The 6,800 sf residence (total) is within walking distance to Downtown, the Community Centre, the lake. The thoughtfully designed layout features a main floor office w/ custom features, a chef's dream kitchen w/ dbl islands, formal dining rm, expansive family rm, (gas fireplaces), mudroom, sauna. Upper level - 5 spacious bedrooms, incl the luxe primary, each w/ ensuite, w/i closets, & fab laundry rm. The lower level offers versatility w/ recreation room (fireplace), guest bedrm, 3-piece bathrm, theater, wine cellar. The extraordinary outdoor oasis features extensive deck/patios, hot tub, cabana, a saltwater pool, a basketball court, firepit, mature trees. A 2018 renovation brought an addition w/ extensive updates throughout the home, & a walk-up to the garden. Triple car garage. More than just a home, it is a rare blend of location, functionality, & outdoor enjoyment, representing the pinnacle of upscale living. More details
    Listed by SOTHEBY`S INTERNATIONAL REALTY CANADA
    Tanya Crepulja
    Steven Fontes
  • 9 Lambert Common in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W7379330

    9 Lambert Common Old Oakville Oakville L6K 0H6
    Main Photo: 9 Lambert Common in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W7379330
    $5,580,000
    Freehold
    Status:
    Active
    MLS® Num:
    W7379330
    Bedrooms:
    4
    Bathrooms:
    6
    Quiet Cul De Sac, Walk Distance To Appleby College. Rare Oakville Lakefront Estate Home W/Limestone Exterior & Contemporary Interior. Total 12 Spots: 6 Inside Parking Spaces & 6 Outside Parking Spaces. 1st Flr 11 Ft, 2nd Flr 10 Ft, Basement 9Ft With Wet Bar, Billiard Room, Gym Room & Media Rm. Upper Level All Bedrooms W/Ensuite. TWO Master Rm With Big Terrace + Lakeview, 3 Fireplaces, All Bathrooms With Heated Floor. $$$ Upgrade Finishes$$$ More details
    Listed by BAY ST. POPULAR REAL ESTATE
    Tanya Crepulja
    Steven Fontes
  • 21 Second Street in Oakville: Old Oakville House (1 1/2 Storey) for sale : MLS®# W8100018

    21 Second Street Old Oakville Oakville L6J 3T1
    Main Photo: 21 Second Street in Oakville: Old Oakville House (1 1/2 Storey) for sale : MLS®# W8100018
    $5,500,000
    Freehold
    Status:
    Active
    MLS® Num:
    W8100018
    Bedrooms:
    3
    Bathrooms:
    2
    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 functional layout with an open concept living and dining room as well as a separate family room with views to the water! There are 2 main floor bedrooms, a 3-pc bathroom and a conveniently located main floor laundry room. Upstairs, the principal retreat provides a walk-in closet, 4-piece bathroom, 3 skylights, and a den with walkout to the upper flat roof where you can watch sailboats gliding across the Lake. Rare, detached double car garage. Located on an approximately 67ft x 170ft riparian lot, graced by mature trees and magnificent lake views off the 2-tiered deck to the water. More details
    Listed by RE/MAX ESCARPMENT REALTY INC.
    Tanya Crepulja
    Steven Fontes
  • 55 Chisholm Street in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8233862

    55 Chisholm Street Old Oakville Oakville L6K 3H6
    Main Photo: 55 Chisholm Street in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8233862
    $4,990,000
    Freehold
    Status:
    Active
    MLS® Num:
    W8233862
    Bedrooms:
    4
    Bathrooms:
    4
    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 with modern innovation. Discover a meticulously crafted residence that exudes sophistication and comfort. Central to the home stands the exquisite soapstone fireplace with all rooms surrounding it effortlessly flowing into each other. Your Scavolini kitchen with Miele appliances serves as the heart of the home and will delight the most sophisticated of home chefs. Not a day will go by without you discovering something new in the whimsical touches that abound. From a three-dimensional stairwell wall, custom ironwork to natural plaster walls, every element speaks to the meticulous attention to detail and dedication to craftsmanship and quality that defines this exceptional property. Upstairs you will find 3 bedrooms and 2 bathrooms with the primary enjoying its own private outside terrace space. Ascend another floor to enjoy your treetop lookout terrace. Your lower level is a testimony to artistry as you appreciate the beauty of the exposed original stone foundation, and boasting a huge den, bedroom, luxurious bathroom, gym, laundry and cedar lined wine cellar. Venture outdoors and find yourself in your own private sanctuary. A lush backyard retreat complete with firepit area, sauna, outdoor shower, outdoor kitchen and dining area, perfect for entertaining or unwinding in style. Your exterior offers an astounding 9 seating areas to relax and unwind. Designed with environmental consciousness in mind, this home incorporates cutting-edge green concepts and sustainable practices. From geothermal heating and cooling, energy recovery ventilation and rainwater harvesting, every feature prioritizes sustainability without compromising on luxury. 55 Chisholm St is reserved for those who seek the extraordinary. More details
    Listed by SOTHEBY`S INTERNATIONAL REALTY CANADA
    Tanya Crepulja
    Steven Fontes
  • 301 Lakeshore Road W in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8107972

    301 Lakeshore Road W Old Oakville Oakville L6K 1G2
    Main Photo: 301 Lakeshore Road W in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8107972
    $4,850,000
    Freehold
    Status:
    Active
    MLS® Num:
    W8107972
    Bedrooms:
    5
    Bathrooms:
    6
    Brand new custom home sit on a private 75 x 140 ft lot surrounded by mature trees. 4+1 bedrooms / 5+1 washrooms, built by Scott Ryan, designed by Keeren Design. Lot boasts extra large circular driveway can park over 8 cars. Main floor features soaring 10-ft ceilings, oversized floor to ceiling windows, Radiant heated porcelain tile flooring throughout main and lower levels, a pot lights, Open white Oak staircases w/ glass panels. Great room features approx 11 ft ceilings, feature wall w/ gas fireplace.Gourmet chef's kitchen features Italian-made cabinetry w/ Quartz countertop & backsplash, top of the line appliances,fully equipped secondary kitchen on the main level! Main floor office B/I cabinetry, oversized window overlooking professionally landscaped front yard. 2nd floor features 9ft ceilings, skylight, hardwood flooring, All bedrooms each include their own private ensuite washroom w/ heated floors! All closets have custom B/I cabinetry. 2nd floor Laundry room w/ B/I cabinetry. More details
    Listed by RIGHT AT HOME REALTY
    Tanya Crepulja
    Steven Fontes
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Data was last updated April 20, 2024 at 03:55 PM (UTC)
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