Old Oakville Luxury Homes

Old Oakville is the crown jewel of the Halton Region, offering a seamless blend of 19th-century charm and contemporary luxury. Nestled along the shores of Lake Ontario, this walkable "Downtown" enclave is the preferred destination for those seeking a prestigious, nautical lifestyle with a distinct small-town feel.

  • Premium Real Estate: Features a majestic mix of restored heritage estates, luxury custom-builds, and exclusive low-rise lakeview condominiums.

  • The Harbor Lifestyle: Centered around the Oakville Harbour and 16 Mile Creek, offering elite yachting, rowing, and lakeside trail systems.

  • Historic Downtown: Immediate access to the upscale boutiques, artisan galleries, and fine dining of Lakeside Park and the George Street corridor.

  • Elite Connectivity: Within walking distance to the Oakville GO Station, providing a sophisticated commute to Toronto’s Financial District.

From the vibrant energy of Trafalgar Road to the quiet, tree-lined streets of the Heritage District, Old Oakville represents the pinnacle of lakeside living and enduring property value.

Curated Lifestyle

Explore the luxury this neighbourhood has to offer

We've searched the Internet and compiled a list of resources we think will be helpful as you set out to buy or sell a home. Please take some time to browse. And feel free to contact us any time with questions or suggestions. We'd love to hear from you!

Market Snapshot

Neighbourhood Story

Price Range

$2,500,000 – $25,000,000+

Inventory Type

A prestigious mix of meticulously restored 1800s heritage manors, custom-built lakeside "New Classics," and ultra-luxury low-rise condominiums with harbor views.

Investment Value

Generational Wealth Preservation. Old Oakville real estate is characterized by extreme scarcity. Its strict heritage protections and proximity to the water create a price floor that has historically outperformed the broader GTA market.

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Featured Properties

Old Oakville Luxury Homes

Explore Old Oakville luxury homes, waterfront estates & historic residences in one of Ontario’s most prestigious lakefront communities.
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1-12/20
  • 350 King Street in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W13430514

    350 King Street 1013 - OO Old Oakville Oakville L6J 1C2
    Main Photo: 350 King Street in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W13430514
    $10,900,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W13430514
    Bedrooms:
    5
    Bathrooms:
    5
    Nestled in the heart of downtown Oakville, this magnificent historical home offers unparalleled charm and elegance, combined with modern amenities. Spanning over 8,000 square feet, the expansive layout provides both grandeur and comfort, perfect for family living or entertaining on a grand scale. With stunning views of the sparkling waters of Lake Ontario, every room is designed to maximize the beauty of its lakeside setting. The home boasts high ceilings, intricate architectural details and walnut hardwood floors, blending timeless craftsmanship with contemporary design. The private lush yard with 104 feet of frontage is a rare gem, providing a serene outdoor oasis with mature trees and ample space for outdoor activities or quiet relaxation and complete privacy. Whether you're enjoying a morning coffee while gazing at the lake or hosting a summer gathering, the outdoor space is as inviting as the interiors. The property's prime location puts you just steps from Oakville's charming downtown, offering convenient access to world-class dining, shopping, and cultural attractions, while still providing the tranquility of lakeside living. With its rich history, extraordinary space, and unbeatable location, this is a once-in-a-lifetime opportunity to own a piece of Oakville's heritage. More details
    Listed by RE/MAX Aboutowne Realty Corp., Brokerage
  • 15 Chartwell Road in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W13707486

    15 Chartwell Road 1013 - OO Old Oakville Oakville L6J 3Z3
    Main Photo: 15 Chartwell Road in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W13707486
    $9,995,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W13707486
    Bedrooms:
    5
    Bathrooms:
    6
    15 Chartwell Rd offers a lifestyle of unparalleled luxury. Drive through the gates & discover the grandeur of this palatial estate. South of Lakeshore,1 door from the lake on a HALF ACRE LOT. Painstakingly curated, the contemporary limestone masterpiece you've been waiting for. Solid iron doors lead to a grand foyer revealing the opulent book matched marble floors. Floor to ceiling wdws & French doors flood the house with light. Cascading waterfalls fank the hall.The Dining Room has statement lighting & servery making hosting a breeze. Soaring 18-ft ceilings & a grand gas f/p are focal points of the Great Room,w/captivating views of the resort style yard. Experience culinary excellence in the black lacquer& glass kitchen by NEFF that features top of the line appliances & a B/I coffee machine & butlers pantry. The intimate Living Room with f/p is the ideal retreat. A main floor office w/built-in cabinetry.2 powder & 2 laundry rooms. The backyard oasis has a gunite pool, waterfalls, fire bowls, covered terrace & outdoor kitchen & f/p.The pool house has a change room,3-pc bath & servery. Towering trees surround the home & are positioned to create privacy. A stone driveway,circular fountain & lush gardens create a breathtaking landscape.Floating marble stairs divide the 3 levels of this home or, you can take the elevator. Skylights make the upstairs airy & bright.The principal suite has nearly 13-ft ceilings, an exquisite 6-piece ensuite & 2 W/I closets. A private balcony overlooks the yard.3 add'l bdrms have 10-ft ceilings,private ensuites & W/I closets. The LL caters to all family members. A 5th bdrm/ensuite makes an ideal guest suite.Gym,R/I Golf Simulator,home theatre,Wine Cellar& doggie Spa. The Games & Rec Rooms have a 2nd kitchen & W/O.Heated garage,baths &LL flrs.Automation. Designed by Bill Hicks & features the artistic creativity of the KT Design Group. Located on Oakville's Street of Dreams, this is an iconic living space designed to impress! LUXURY CERTIFIED More details
    Listed by RE/MAX Escarpment Realty Inc., Brokerage
  • 115 Trafalgar Road in Oakville: 1013 - OO Old Oakville Commercial for sale : MLS®# W13237504

    115 Trafalgar Road 1013 - OO Old Oakville Oakville L6J 3G3
    Main Photo: 115 Trafalgar Road in Oakville: 1013 - OO Old Oakville Commercial for sale : MLS®# W13237504
    $8,999,999 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    W13237504
    Total Area:
    18,997 sq. ft.
    Rare opportunity to own a building right on Trafalgar in Downtown Oakville. Already passed approval to build up to 6 stories! Amazing future development site ready to go! New leases in place on some units at proper market rents. When fully leased over a 6% cap rate. More details
    Listed by RE/MAX REALTY ENTERPRISES INC.
  • 46 Second Street in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W13694012

    46 Second Street 1013 - OO Old Oakville Oakville L6J 3T2
    Main Photo: 46 Second Street in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W13694012
    $7,599,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W13694012
    Bedrooms:
    5
    Bathrooms:
    7
    Walk to downtown Oakville from this 2024 custom-built residence, just three houses from Lake Ontario on a 65' x 158' lot south of Lakeshore. A rare new-construction opportunity in Old Oakville's most walkable pocket-minutes from the harbour, the Oakville Club, Lakeshore Road dining, and waterfront trails. Offers 4,362 sq. ft. above grade plus a 2,468 sq. ft. finished lower level (6,830 sq. ft. total). Net Zero Ready with a Tarion warranty, crafted by Chatsworth Fine Homes alongside architect John Willmott and designer Jane Lockhart. Main floor features herringbone white oak floors, panel mouldings, a private office, custom mudroom, and a formal dining room. The chef's kitchen boasts Miele appliances (plumbed coffee system, dual steam/standard ovens), SubZero refrigeration, and a wine column. It opens to a great room with a linear fireplace, custom built-ins, and floor-to-ceiling garden views. The primary suite serves as a spa-inspired retreat with a freestanding tub, oversized shower, double vanity, and a dressing-island walk-in closet. Secondary bedrooms each feature private ensuites. Includes heated floors, curbless showers, and upper-level laundry with two washer/dryer sets. The lower level (10' ceilings) is built to entertain: rec room with custom bar/kitchenette, gym, theatre, full bath, additional bedroom, and walk-up access to the yard. The west-facing rear yard catches optimal afternoon sun, complete with a covered heated lounge, in-ground pool with waterfall, and a hot tub. Extras include partial lake views, a heated driveway, radiant floor heating, Crestron automation, Tesla charger rough-in, and a standby generator. A turn-key luxury home in prime Old Oakville where inventory like this rarely comes to market. LUXURY CERTIFIED. More details
    Listed by RE/MAX Escarpment Realty Inc., Brokerage and RE/MAX Escarpment Realty Inc
  • 305 Church Street in Oakville: 1013 - OO Old Oakville Commercial for sale : MLS®# W13793920

    305 Church Street 1013 - OO Old Oakville Oakville L6J 7T2
    Main Photo: 305 Church Street in Oakville: 1013 - OO Old Oakville Commercial for sale : MLS®# W13793920
    $7,000,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    W13793920
    Major Bus.:
    Bank
    Total Area:
    11,573 sq. ft.
    An exceptional opportunity to own a substantial 11,000 sq. ft. four-storey office building in the heart of downtown Oakville. Ideally located within walking distance of Oakville's vibrant downtown, restaurants, cafés, shops and amenities. Featuring high-end executive finishes, the property currently serves as the headquarters of a prestigious financial wealth management firm catering to high-net-worth clients. The sophisticated layout includes multiple private offices, boardrooms, four kitchens, two fireplaces and an outdoor patio. The flexible configuration provides an excellent opportunity for an owner-user, corporate headquarters or multi-tenant investment strategy. A rare downtown Oakville offering combining scale, quality, location and flexibility-ideal for investors or professional users seeking a distinctive commercial property in one of Oakville's most desirable business locations. More details
    Listed by RE/MAX REALTY SPECIALISTS INC.
  • 153 Balsam Drive in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W13779262

    153 Balsam Drive 1013 - OO Old Oakville Oakville L6J 3X4
    Main Photo: 153 Balsam Drive in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W13779262
    $6,575,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W13779262
    Bedrooms:
    5
    Bathrooms:
    5
    153 Balsam Drive is a sophisticated 4,337 sqft custom residence set on a 50' x 304' park-like lot in one of Oakville's most sought-after settings. Close to Downtown Oakville, top-rated schools, the home pairs craftsmanship with thoughtful functionality. A dramatic double-volume marble foyer with heated flooring and architectural staircase creates an elegant arrival, while custom millwork, designer lighting, oversized windows and premium white oak flooring establish a refined aesthetic throughout. The main level is designed for family living and entertaining, with gracious living and dining spaces flowing into a warm family room with a wood-burning fireplace. A dedicated office overlooks mature greenery. At the heart of the home, the kitchen features a 10' x 4' marble island, face-frame cabinetry, marble surfaces, bespoke lighting and a 60" Lacanche range with a custom plaster hood. A marble-finished pantry and heated natural-stone mudroom add function and elegance. Upstairs, four bedrooms each feature a walk-in closet. The primary suite offers a vaulted ceiling, double skylights with remote blinds, a lounge area and an oversized walk-in closet. The spa-inspired ensuite features heated marble floors, a steam shower with double heated marble seating, custom wainscoting, detailed marble trim and an imported Water Monopoly bathtub. The lower level extends the home's living and entertaining spaces with 10' ceilings and zoned underfloor heating. A fifth bedroom, recreation and games rooms, gym, wine cellar and theatre/flex space offer exceptional versatility for family living and entertaining. A heated three-car garage with car-lift capacity for two additional vehicles, plus exterior snow-melt infrastructure, adds year-round convenience. 153 Balsam Drive is a rare combination of timeless architecture, refined materials, modern functionality and exceptional attention to detail, thoughtfully brought together on one of Oakville's most coveted streets. More details
    Listed by CENTURY 21 MILLER REAL ESTATE LTD.
  • 54 RAYMAR Place in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W14097832

    54 RAYMAR Place 1013 - OO Old Oakville Oakville L6J 6M1
    Main Photo: 54 RAYMAR Place in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W14097832
    $6,500,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W14097832
    Bedrooms:
    5
    Bathrooms:
    5
    This exceptional residence has been extensively upgraded with curated enhancements that seamlessly blend timeless architecture with modern luxury, advanced technology and exceptional craftsmanship. Designed for effortless indoor-outdoor living, the enclosed lanai features floor-to-ceiling glass sliding doors on three sides with automated electronic screens for year-round comfort and privacy. The professionally landscaped grounds include a custom 13' x 9' powered garden pavilion, natural stone entertaining terrace, 1,100 sq. ft. wraparound composite deck, approximately 500 sq. ft. of Ipe hardwood privacy screening, luxury hot tub, heated saltwater pool with waterfall, 20-foot motorized retractable awning and a fully automated seven-zone irrigation system and hot tub. The gourmet kitchen has been refreshed w/ custom cabinetry doors and drawer fronts while maintaining its timeless design. Premium appliances include two built-in dishwashers, two wall ovens, integrated refrigerator and freezer, built-in microwave, approximately 100-bottle wine refrigerator and two oversized island prep sinks with garburators. The principal fireplace has been restored with a custom surround, creating a stunning focal point. The luxurious primary suite features restored wood paneling, a custom dressing room, spa-inspired ensuite with freestanding tub, steam shower, heated floors and heated towel warmers. A DuraDek waterproof roof system (2023) was installed over the private terrace. All upper bedroom ensuites also feature radiant heated floors and heated towel warmers. An upgraded Crestron Smart Home system controls lighting, climate, motorized blinds, distributed audio and home automation. The home is equipped with three owned high-efficiency furnaces, three air con. systems, two steam humid., two-zone climate control. Exterior Shower. Every detail has been thoughtfully curated to deliver timeless elegance & intelligent technology. More details
    Listed by RE/MAX ESCARPMENT REALTY INC.
  • 533 Carson Lane in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W13724050

    533 Carson Lane 1013 - OO Old Oakville Oakville L6J 6M3
    Main Photo: 533 Carson Lane in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W13724050
    $6,250,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W13724050
    Bedrooms:
    6
    Bathrooms:
    7
    This magnificent custom residence is nestled in one of Oakville's most prestigious neighbourhoods, just a short stroll from the lake and downtown Oakville. Offering over 6,500 sq. ft. of exquisitely designed living space, this exceptional home seamlessly blends contemporary sophistication with exceptional luxury. Every detail has been meticulously considered, from heated floors on the main and lower levels to a private elevator serving all three floors. A sunlit two-storey foyer introduces an elegant interior defined by refined finishes and thoughtful design. The expansive Great Room features soaring 20-foot ceilings and a dramatic wall of windows overlooking the professionally landscaped grounds. Walk out to an elegant patio with gas BBQ hookup, ideal for summer entertaining and alfresco dining. The gourmet kitchen is a true showpiece, featuring sophisticated two-tone cabinetry, an expansive centre island and state-of-the-art appliances. The adjoining butler's pantry provides additional prep space and connects seamlessly to the elegant Dining Room, where built-in speakers and views of the front gardens create an exceptional setting for entertaining.A serene formal Living Room offers a refined retreat, while the main-floor bedroom, easily converted to an office, features a private ensuite and direct patio access. A sculptural floating staircase leads to the skylit second level, where the luxurious primary suite offers two walk-in closets and a spa-inspired ensuite. Three additional bedrooms, each with secure closets and heated ensuites, provide comfort and privacy. The lower level is an entertainer's dream, featuring a heated underground garage with vehicle turntable, stylish recreation room with walk-up to the backyard, and space for a state-of-the-art theatre or gym.An extraordinary residence offering sophisticated design, exceptional amenities and an unparalleled Oakville lifestyle. More details
    Listed by ROYAL LEPAGE REAL ESTATE SERVICES PHINNEY REAL EST
  • PH1 300 Randall Street in Oakville: 1013 - OO Old Oakville Condo Apartment for sale : MLS®# W13453644

    PH1 300 Randall Street 1013 - OO Old Oakville Oakville L6J 0G2
    Main Photo: PH1 300 Randall Street in Oakville: 1013 - OO Old Oakville Condo Apartment for sale : MLS®# W13453644
    $5,999,900
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    W13453644
    Bedrooms:
    3
    Bathrooms:
    4
    RESTORATION HARDWARE SHOW SUITE: Welcome to the crown jewel of The Randall Residences, Oakville's most prestigious address. This sun-filled Signature Penthouse Suite is the largest residence inside and out, offering approximately 3,337 sq. ft. of sophisticated living plus a 386 sq. ft. second-storey lounge with skylight and an expansive 1,327 sq. ft. southeast-facing terrace. Enter through a grand rotunda foyer with marble floors and an impressive RH chandelier, setting the tone for this exceptional home. The open-concept living and dining areas boast 12-foot ceilings, floor-to-ceiling wrap-around windows, custom Downsview cabinetry, top-of-the-line appliances, and a gas fireplace - an entertainer's dream. Restoration Hardware fixtures illuminate throughout the suite exuding an atmosphere of sophisticated refinement. The principal bedroom retreat is a haven of tranquility with a custom zebra-wood dressing room and a spa-inspired 6-piece ensuite, complete with heated marble floors, polished nickel fixtures, and a freestanding soaking tub. Two additional bedrooms each feature their own private ensuites for ultimate comfort and privacy. Ascend to the second-storey lounge, ideal for a home gym, office, or serene retreat, and step out to your private rooftop terrace designed for entertaining, featuring multiple lounging and dining zones with a gas BBQ hookup. Additional luxuries include a Crestron home automation system, integrated entertainment features, 3 parking spaces, and 2 storage lockers. Residents enjoy 24-hour concierge service in this award-winning Rosehaven Homes development, celebrated for its impeccable craftsmanship and timeless elegance. Sotto Sotto on the ground floor. Located steps from Lake Ontario, fine dining, boutique shopping, and just minutes to major highways, this penthouse represents the pinnacle of luxury living in Oakville. If you demand the best, look no further. Luxury Certified. Listed US$4,255,000 More details
    Listed by RE/MAX ESCARPMENT REALTY INC.
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  • 254 Donessle Drive in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W14110352

    254 Donessle Drive 1013 - OO Old Oakville Oakville L6J 3Y6
    Main Photo: 254 Donessle Drive in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W14110352
    $5,349,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W14110352
    Bedrooms:
    6
    Bathrooms:
    6
    From the moment you arrive, 254 Donessle Drive makes a lasting impression. Stately and estate-like, this meticulously maintained residence showcases timeless architecture, exceptional craftsmanship and the generous proportions of a distinguished family home.Set on a magnificent 108' x 192' west-facing property on one of Southeast Oakville's most coveted streets, the home offers approximately 7,531 sq. ft. of living space amid mature trees, established gardens and remarkable privacy.A soaring two-storey foyer introduces rich hardwood floors, exquisite millwork and elegant principal rooms. The dramatic two-storey living room features towering windows, French doors and a floor-to-ceiling stone fireplace. A wood-panelled executive den and formal dining room provide refined spaces for work and entertaining.The expansive kitchen features custom Downsview cabinetry, a 13' island with granite countertop and Wolf and Sub-Zero appliances. Open to the breakfast area and fireside family room, it forms the heart of the home.Upstairs, four bedrooms each enjoy a private ensuite. The primary retreat includes a fireplace, custom walk-in closet and luxurious five-piece bath with heated floors, steam shower and air-jet tub. The finished lower level offers a recreation room, custom bar, wine cellar, gym and two additional bedrooms.Outside, the west-facing gardens are equally impressive, with a heated saltwater pool, custom cabana with bar and change room, stone terraces and expansive lawns-an exceptional setting for afternoon sun and evening entertaining. A triple-car garage, fitted mudroom and abundant storage complete the home.Moments from the lake, excellent schools and local amenities, 254 Donessle Drive is a rare opportunity to own a home of enduring quality, where the grounds are every bit as remarkable as the residence itself. Luxury Certified. More details
    Listed by RE/MAX Escarpment Realty Inc., Brokerage
  • 317 Gloucester Avenue in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W13879172

    317 Gloucester Avenue 1013 - OO Old Oakville Oakville L6J 3W8
    Main Photo: 317 Gloucester Avenue in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W13879172
    $5,130,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W13879172
    Bedrooms:
    4
    Bathrooms:
    4
    Timeless Elegance in the Heart of Olde Oakville. A rare property on one of the community's most coveted streets. Experience refined living in this exceptional residence set on a triple lot over 1/2 acres with an impressive 154.73ft frontage, curated for those who value privacy, design and indoor-outdoor living at its finest. Beautifully reimagined in 2024 & 2026, the main level showcases a sophisticated blend of transitional elegance and casual upscale comfort, perfect for both everyday living and effortless entertaining. A Main Floor Redesigned for Modern Luxury. Step inside to wide-plank oak hardwood floors, luxurious finishes, and stunning sightlines to the property's park-like grounds. The custom kitchen is a true showpiece, featuring: Main kitchen+ second "messy kitchen" for concealed prep, storage, and small appliances. Square island with integrated fridge/freezer drawers. Quartz countertops & full-height backsplash in both kitchens. Built-in wine/beverage and dedicated coffee station. A walk-out from the dining room and a large picture window open to views of the serene screened-in sun porch ,creating a seamless flow for indoor-outdoor enjoyment. The magnificent great room features dramatic cathedral ceilings, a stone wood-burning fireplace with aged beam mantel. A second walk-out continues to the sun porch framed by nature. The upper level has been thoughtfully elevated with beautiful new wide plank oak hardwood flooring creating a warm and sophisticated foundation for the home. This exceptional level features flexible living spaces with 4 bedrooms and 3 full bathrooms offering both comfort and functionality. Third floor loft/suite ideal as 4th bedroom, guest suite or office. Every detail has been carefully considered, including new custom window coverings throughout & beautifully appointed spaces filled with natural light. More details
    Listed by RE/MAX REALTY ENTERPRISES INC.
1-12/20
Data was last updated October 24, 2026 at 04:15 AM (UTC)
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.