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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 136 listings, but only 100 are available for public display. To get instant access to all 136 listings, please .
1-12/100
  • 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
  • 104 Lakeshore Road W in Oakville: Old Oakville Property for sale : MLS®# W9012273

    104 Lakeshore Road W Old Oakville Oakville L6K 1E3
    Main Photo: 104 Lakeshore Road W in Oakville: Old Oakville Property for sale : MLS®# W9012273
    $11,950,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    W9012273
    Major Bus.:
    Retail Store Related
    Total Area:
    9,675 sq. ft.
    The Beer Store is an excellent AAA Tenant With a 15-year lease plus options with both parties having Termination rights. The Tenant's after 10 years and the Landlord's termination rights can beexecuted at any time for re-development. Ask the listing agent for details.This single tenant property is situated on 0.58 acres of land & is located on the southwest corner of Lakeshore Road West and Kerr Street. This rare opportunity in downtown Oakville is just a quick walk to Lake Ontario. It's the perfect scenario that provides income today and incredible mix use re-development in the future. Ask the listing agent about an identical property two blocks away which recently received a staff recommendation report and an official plan amendment, which allows them eight floors andapproximately 109,000 ft.2 More details
    Listed by SUTTON GROUP-ADMIRAL REALTY INC.
    Tanya Crepulja
    Steven Fontes
  • 27 Park Avenue in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W9369754

    27 Park Avenue Old Oakville Oakville L6J 3X9
    Main Photo: 27 Park Avenue in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W9369754
    $11,000,000
    Freehold
    Status:
    Active
    MLS® Num:
    W9369754
    Bedrooms:
    5
    Bathrooms:
    9
    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 10,000 square feet on an expansive lot adorned with lush landscaping. A retreat awaits outdoors, boasting a resort-style infinity pool, a chic 950 square foot pool house featuring a bar, fireplace, and vaulted ceiling, alongside your personal putting green and in-ground trampoline. Inside, indulge in luxury with marble heated floors, 10-inch wide plank white oak flooring, and designer light fixtures throughout. The heart of the home is the gourmet kitchen, complete with a La Cornue oven and premium appliances, complemented by a generous pantry. With 4+1 bedrooms, two of which feature spacious dedicated study areas, sure to inspire students seeking independent study and 9 bespoke bathrooms, every corner exudes sophistication. Enhanced by a state-of-the-art security and sound system, the main floor offers a parlour, office, laundry room, formal dining room with servery, great room, and mud room off the heated garage. Descend the grand staircase to discover the fully finished lower level, featuring two full baths, a gym, extensive wine cellar, theatre room, bar, bedroom, mechanical room, media room, safe room, cedar closet, and ample storage. Park Avenue named for the horse and buggies that use to park on it when attending the polo matches in the 1800s. It was once the home of many cottagers who visited in the summer to enjoy Orchard Beach on Lake Ontario. So much history for where this timeless lakeside home resides. With a short walk to town, its proximity to the lake and the outstanding finishes throughout, it is truly one of the most gracious new homes in the area. More details
    Listed by RE/MAX ABOUTOWNE REALTY CORP.
    Tanya Crepulja
    Steven Fontes
  • 26 Trafalgar Road in Oakville: Old Oakville House (3-Storey) for sale : MLS®# W9011999

    26 Trafalgar Road Old Oakville Oakville L6J 3E7
    Main Photo: 26 Trafalgar Road in Oakville: Old Oakville House (3-Storey) for sale : MLS®# W9011999
    $9,998,000
    Freehold
    Status:
    Active
    MLS® Num:
    W9011999
    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 lakefront 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 6 beautifully 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
  • 128 Balsam Drive in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8440984

    128 Balsam Drive Old Oakville Oakville L6J 3X5
    Main Photo: 128 Balsam Drive in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8440984
    $7,350,000
    Freehold
    Status:
    Active
    MLS® Num:
    W8440984
    Bedrooms:
    7
    Bathrooms:
    9
    Masterfully crafted west coast transitional set back on one of the most prestigious streets in SE Oakville. A few homes north of Lakeshore Road on a large estate lot, this newly built custom home is incredible. Seamless flow w/an easy layout that provides connected main living spaces + privacy. Timeless aesthetic w/a blend of white oak, natural marble, beautiful fixtures, neutral-hued quartz + custom milled cabinetry throughout this is warm west coast style at its finest. 9107 total square feet. 5+2 bedrooms + 10 baths. Private office w/ wall-to-wall built-ins, formal living w/fp + dining w/walnut-clad servery. Expansive kitchen w/custom full-height cabinetry, integrated appliances + expansive marble+walnut island w/prep space + seating. Sunroom style breakfast area + family room w/cozy gas fp. Both breakfast + fr have double glass doors that open to the rear portico. A picturesque place to enjoy a morning coffee or an evening meal. Mudroom maximizes utility w/ wall-to-wall cabinetry + access to the garage + yard + 3-piece bath. The primary is a retreat with expansive glazing, double glass doors, beautiful millwork, 2-sided fireplace, dressing room with custom built-ins + a boutique hotel spa ensuite. Each additional bedroom is generously sized with walk-in + ensuite. Cleverly placed windows + 7 skylights keep this level bright + upper laundry offers convenience. The lower level expands living space w/rec room, games space, custom wine cellar/tasting room, wet bar, theatre w/tiered seating + 2 beds w/ensuites. This is a fun family level. Expansive rear yard w/wood-clad portico w/stone fp + flat grassy area. Perennials+mature trees frame the back fence line. Steps to Lakeshore Road, walk the paths along the shores of Lake Ontario, explore downtown Oakville and enjoy easy access to the GO train and major HWYs. Walk to New Central Elementary + close to private + public schools. More details
    Listed by CENTURY 21 MILLER REAL ESTATE LTD.
    Tanya Crepulja
    Steven Fontes
  • 280 Balsam Drive in Oakville: Old Oakville House (Sidesplit 3) for sale : MLS®# W9265179

    280 Balsam Drive Old Oakville Oakville L6J 3X6
    Main Photo: 280 Balsam Drive in Oakville: Old Oakville House (Sidesplit 3) for sale : MLS®# W9265179
    $6,695,000
    Freehold
    Status:
    Active
    MLS® Num:
    W9265179
    Bedrooms:
    4
    Bathrooms:
    7
    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 meticulously designed living space, this residence offers a blend of elegance and comfort. Each of the spacious bedrms features its own private ensuite, ensuring convenience and privacy for everyone. Entertain in style with 3 well-appointed bars, perfect for hosting gatherings or relaxing with friends. The homes incredible landscaping/hardscaping create a picturesque outdoor setting, complementing the beautifully maintained interior. Work from home with ease in one of the two dedicated offices, or unwind in the covered, screened porch with its inviting fireplace. Every inch of this home has been fully updated and boasts high-end finishes and thoughtful upgrades throughout. This property is more than just a home, it's a lifestyle! More details
    Listed by RE/MAX ABOUTOWNE REALTY CORP.
    Tanya Crepulja
    Steven Fontes
  • 18 Holyrood Avenue in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W9266728

    18 Holyrood Avenue Old Oakville Oakville L6K 2V3
    Main Photo: 18 Holyrood Avenue in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W9266728
    $6,250,000
    Freehold
    Status:
    Active
    MLS® Num:
    W9266728
    Bedrooms:
    3
    Bathrooms:
    5
    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 wonderful neighbors, this home is designed with family in mind and exudes a coastal ambiance inspired by the timeless style of Nancy Meyers. Step inside to find a fully renovated interior where every detail has been meticulously curated to enhance comfort and sophistication. The open-concept main floor features a spacious kitchen and family room, both drenched in natural light and boasting unobstructed lake views. Morning coffee on the rear deck or kitchen banquette is the perfect space to reflect in the morning or unwind at night. Offering 3 generously sized bedrooms all equipped with their own private ensuites, providing ample space and privacy for every member of the family. The master suite is a private retreat, complete with its own spa-like bathroom, private dressing room, and picturesque views of the lake. One of the standout features of this property is its direct lake access, allowing you to easily launch a paddleboard or simply enjoy the serene waters right at your doorstep. Whether you're an avid water sports enthusiast or just looking for a peaceful spot to unwind, this home delivers. Located just minutes from Appleby College, downtown Oakville, and a host of other amenities, this property offers both convenience and a high-quality lifestyle. From shopping and dining to top-rated schools and recreational activities, everything you need is within easy reach. This waterfront gem is everything a family could wish for - luxury, comfort, and an unbeatable location. Don't miss the opportunity to make this dream home your own. More details
    Listed by RE/MAX ABOUTOWNE REALTY CORP.
    Tanya Crepulja
    Steven Fontes
  • 200 Chartwell Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W9295111

    200 Chartwell Road Old Oakville Oakville L6J 3Z8
    Main Photo: 200 Chartwell Road in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W9295111
    $5,995,000
    Freehold
    Status:
    Active
    MLS® Num:
    W9295111
    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
  • 24 Raymar Place in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8478560

    24 Raymar Place Old Oakville Oakville L6J 6M1
    Main Photo: 24 Raymar Place in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W8478560
    $5,850,000
    Freehold
    Status:
    Active
    MLS® Num:
    W8478560
    Bedrooms:
    6
    Bathrooms:
    5
    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 in 2011, outdoor space added in 2015. 18,535sqft pie-shaped property, complete with saltwater pool & hot tub. Impeccably maintained. Timeless architecture & impressive curb appeal. Main floor features large principal rooms with Travertine tile, hardwood, Pella windows (with B/I blinds), pot lighting, B/I speakers, 2 storey high ceilings (in sitting room) & skylights. High end kitchen with Wolf, Subzerio and Miele appliances, oversized centre island, custom cabinetry & adjacent eat-in breakfast room. Kitchen opens to family room with 9'6 coffered ceilings, gas fireplace (with marble surround & wood mantle). Enclosed outdoor space with mounted heaters, ceiling fans, retractable screens, flatscreen TV, two-sided fireplace and outdoor kitchen with built-in Lynx BBQ. 2nd floor boasts large primary with walk-in closet (with custom organizers), California shutters & B/I speakers. 5pc ensuite with double vanity, soaker BainUltra tub (with Perrin & Rowe hardware) & oversized glass enclosed shower. 2nd floor includes 3 additional large bedrooms, 2 additional bathrooms and laundry room. 2nd floor also features combination exercise room/office with 3-sided fireplace & vaulted coffered ceiling. Large basement complete with 2 bedrooms, full bath, bar area, rec room, temperature controlled wine cellar & recently improved utility room. Professionally landscaped, towering trees & manicured gardens. Hardscaped with armour stone, interlock stone work and border & retaining walls. Salt water pool with adjoining hot tub with stone waterfall feature. 3 car garage. Raymar is one of Oakvilles most desirable streets, offering a rare combination of tranquility & easy access to Downtown Oakville amenities. More details
    Listed by ROYAL LEPAGE REAL ESTATE SERVICES LTD.
    Tanya Crepulja
    Steven Fontes
  • 235 Lakewood Drive in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W9366585

    235 Lakewood Drive Old Oakville Oakville L6K 1B3
    Main Photo: 235 Lakewood Drive in Oakville: Old Oakville House (2-Storey) for sale : MLS®# W9366585
    $4,999,998
    Freehold
    Status:
    Active
    MLS® Num:
    W9366585
    Bedrooms:
    5
    Bathrooms:
    6
    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 renowned architect Gren Weis, the fusion of stone and wood siding spans over 6,200 square feet. Step into the foyer with its soaring cathedral ceilings, offering glimpses of the expansive living spaces beyond. Designed for seamless flow, this sophisticated layout effortlessly accommodates both grand and intimate gatherings. A bespoke oak staircase adorned with shimmering Schonbek chandeliers leads to the upper levels, where solid oak hardwood flooring graces much of the home. The living room boasts exquisite millwork, custom fireplace, and state-of-the-art entertainment amenities by Canadian Sound Ltd. The gourmet kitchen, recently reimagined, features top-tier appliances, quartz countertops, and abundant storage, with access to a sprawling composite, low maintenance deck. A stately maple wood-paneled study overlooks manicured gardens, providing a serene retreat. Five generous bedrooms, each with an ensuite and ample closets, offer luxurious comfort. The primary suite is a haven of indulgence, flaunting dual walk-in closets, spa-like ensuite with airy vaulted ceilings, skylights, and deluxe fixtures. The lower level is all about leisure and function, boasting a custom-painted wood-paneled rec room with lakeside vibes, alongside a gym, wine cellar, and top-notch utility room. Outside, the meticulously landscaped grounds offer a saltwater pool with waterfall, a spa, and outdoor entertainment system, perfect for alfresco movie nights. This home boasts a brand new roof with lifetime warranty! Stroll to lovely downtown Oakville, trendy Kerr Village, Tannery Park along the Lake & waterfront trails. Close proximity to highly esteemed schools. More details
    Listed by RE/MAX ABOUTOWNE REALTY CORP.
    Tanya Crepulja
    Steven Fontes
  • 21 Second Street in Oakville: Old Oakville House (1 1/2 Storey) for sale : MLS®# W9347095

    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®# W9347095
    $4,999,000
    Freehold
    Status:
    Active
    MLS® Num:
    W9347095
    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
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Data was last updated September 26, 2024 at 11:55 PM (UTC)
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