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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1-12/22
  • 350 King Street in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W12698652

    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®# W12698652
    $12,900,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W12698652
    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. 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®# W12824170

    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®# W12824170
    $11,750,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W12824170
    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 and RE/MAX Escarpment Realty Inc
  • 115 Trafalgar Road in Oakville: 1013 - OO Old Oakville Commercial for sale : MLS®# W12700720

    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®# W12700720
    $8,999,999 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    W12700720
    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. More details
    Listed by RE/MAX REALTY ENTERPRISES INC.
  • 46 Second Street in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W12704590

    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®# W12704590
    $8,479,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W12704590
    Bedrooms:
    5
    Bathrooms:
    7
    Discover an extraordinary custom built residence in prestigious Old Oakville, where architectural excellence meets modern luxury just steps from the lake.This 2024 Net Zero Ready masterpiece represents a distinguished collaboration between renowned industry leaders Chatsworth Fine Homes,architect John Willmott,and designer Jane Lockhart.The impressive foyer welcomes you with sophisticated elegance, flowing into a formal dining room adorned w/ dual chandeliers,herringbone white oak floors,and exquisite wall treatments.Panel moldings throughout create timeless continuity.The gourmet kitchen showcases premium Miele & SubZero appliances.This culinary centerpiece seamlessly connects to the Great Room,where a sleek linear f/p anchors custom built-ins and expansive windows extending to outdoor entertaining spaces.A servery,custom mudroom with exterior access,and private main floor office enhance functionality.Upstairs,the luxurious primary suite provides a serene sanctuary featuring a spa-inspired ensuite w/ freestanding tub,oversized shower,double vanity,makeup area & walk-in closet complete with island.Secondary bedrooms offer private ensuites & generous walk-in closets.All bathrooms include heated floors & curbless showers.A super functional laundry room is also on this level.The lower level w/ 10' ceilings transforms into an entertainment haven with spacious rec room, custom bar and kitchenette,bedrm, gym,3 & 2 pc bath,theatre room, and storage. Convenient walk-up access to the backyard.The outdoor oasis features a covered heated lounge,inground pool w/ waterfall,hot tub,and professional landscaping.Extra features incl heated driveway,west-facing yard capturing afternoon sun,partial lake views,radiant in-floor heating & Crestron home automation deliver unparalleled comfort and efficiency,R/I Tesla Supercharger & Generator.Tarion warranty.This remarkable residence epitomizes architectural distinction and refined living.LUXURY CERTIFIED. More details
    Listed by RE/MAX Escarpment Realty Inc., Brokerage and RE/MAX Escarpment Realty Inc
  • 116 Chartwell Road in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W12490592

    116 Chartwell Road 1013 - OO Old Oakville Oakville L6J 3Z6
    Main Photo: 116 Chartwell Road in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W12490592
    $7,995,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W12490592
    Bedrooms:
    4
    Bathrooms:
    6
    Welcome to 116 Chartwell Road, one of Southeast Oakville's architecturally significant and environmentally advanced residences. Built to Net-Zero specifications, this home is a masterclass in modern sustainability, where wellness, technology and design exist in seamless harmony. This eco-friendly home prioritizes your health with a fully sealed building envelope, advanced insulation, and a geothermal system paired with a 14.49kW solar array. This ensures clean, energy-efficient living by reducing exposure to pollutants and maintaining exceptional indoor air quality and comfort. The open-concept layout is bathed in natural light featuring custom mahogany-framed floor-to-ceiling windows and a striking pyramid skylight. The gourmet kitchen features a generous Diamante Quartzite island, custom lacquered cabinetry, and top-tier Gaggenau appliances. The main floor primary suite is a serene retreat with a luxurious 5-piece ensuite featuring a steam shower and an oversized soaking tub. The home office, with its serene garden views and a floor-to-ceiling oak bookcase offers a calming workspace. Outdoors, a stylish covered patio with a mahogany-clad ceiling, dual Kenyon barbecues, a stainless steel hot tub, and surround sound creates an inviting space for relaxation and entertaining. Smart home technology seamlessly integrates audio-visual, lighting, and security systems, controlled via intuitive apps. The exterior impresses with Neolith cladding, automated gates, irrigation and lighting. A tandem four-car garage with a hydraulic lift and EV charging, extra outdoor parking speaks to the car enthusiast. In times of need the Generac generator covers the entire home. This is not simply a luxury home, it is a forward thinking modern masterpiece in one of Oakville's most prestigious enclaves. More details
    Listed by Sotheby's International Realty Canada, Brokerage
  • 221 Lakeshore Road E in Oakville: 1013 - OO Old Oakville Commercial for sale : MLS®# W12707962

    221 Lakeshore Road E 1013 - OO Old Oakville Oakville L6J 1H7
    Main Photo: 221 Lakeshore Road E in Oakville: 1013 - OO Old Oakville Commercial for sale : MLS®# W12707962
    $7,650,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    W12707962
    Total Area:
    14,736 sq. ft.
    An exceptional opportunity to acquire a fully leased, multi-use investment property in the centre of downtown Oakville. The building boasts 14,736 sq. ft. across three storeys and features prime frontage on Lakeshore Road East. Marketing brochure and financial information available upon request. More details
    Listed by CDN Global Indusite Realty
    To access this listing,
    please create a free account

  • 221 Lakeshore Road E in Oakville: 1013 - OO Old Oakville Commercial for sale : MLS®# W12707970

    221 Lakeshore Road E 1013 - OO Old Oakville Oakville L6J 1H7
    Main Photo: 221 Lakeshore Road E in Oakville: 1013 - OO Old Oakville Commercial for sale : MLS®# W12707970
    $7,650,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    W12707970
    Total Area:
    14,736 sq. ft.
    An exceptional opportunity to acquire a fully leased, multi-use investment property in the centre of downtown Oakville. The building boasts 14,736 sq. ft. across three storeys and features prime frontage on Lakeshore Road East. More details
    Listed by CDN Global Indusite Realty
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    please create a free account

  • 200 Chartwell Road in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W12783046

    200 Chartwell Road 1013 - OO Old Oakville Oakville L6J 3Z8
    Main Photo: 200 Chartwell Road in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W12783046
    $6,299,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W12783046
    Bedrooms:
    5
    Bathrooms:
    7
    Nestled behind private gates on one of Oakville's most coveted "Street of Dreams," this exceptional estate sits on a spectacular 100 x 225 ft lot and offers over 7,500 sq ft of luxurious finished living space. Surrounded by manicured gardens and mature trees, the home blends timeless architecture with sophisticated, on-trend finishes and commanding curb appeal. A grand double-height foyer introduces an elegant interior designed for refined living and effortless entertaining. The main level features a chef-inspired kitchen with custom cabinetry, seamlessly open to a spacious family room. A private office, formal living room, piano lounge, and a stunning three-season Muskoka room extend the living space into the tranquil backyard. Upstairs, the luxurious principal retreat showcases a sleek linear gas fireplace, dual spa-inspired ensuites, separate walk-in closets, and a boutique-style dressing room, with a private balcony overlooking the Muskoka-like setting. Three additional bedrooms each offer private ensuites and generous custom closets for ultimate comfort and privacy. The fully finished lower level-accessible by both the main staircase and a unique main-floor slide-offers expansive recreation and games areas, a theatre, gym/fifth bedroom, full bath, and abundant storage. Two laundry rooms provide exceptional convenience for modern family living.Since 2025, the owner has invested significantly in premium upgrades, including enhancements to the kitchen cabinetry, custom closet built-ins, lower-level laundry room, fireplaces in the living and family rooms, window treatments, appliances, primary dressing area, and multiple bathrooms-further elevating the home's quality and turnkey appeal. A rare opportunity to own a gated estate of scale, elegance, and enduring value in prestigious S.E Oakville. More details
    Listed by Re/Max Hallmark Realty Ltd.
  • PH1 300 RANDALL Street in Oakville: 1013 - OO Old Oakville Condo Apartment for sale : MLS®# W12517736

    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®# W12517736
    $5,999,900
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    W12517736
    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 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. More details
    Listed by RE/MAX ESCARPMENT REALTY INC.
  • 184 Chartwell Road in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W12726244

    184 Chartwell Road 1013 - OO Old Oakville Oakville L6J 3Z8
    Main Photo: 184 Chartwell Road in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W12726244
    $5,699,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W12726244
    Bedrooms:
    5
    Bathrooms:
    7
    Welcome to 184 Chartwell Road, a distinguished residence offering over 7,800 sq. ft. of living space on a rare 100 x 238 ft premium lot (RL-1 zoning) in one of Oakville's most sought-after neighbourhoods. With 5 bedrooms, 4 bathrooms, and over 23,000 sq. ft. of land, this exceptional property presents a perfect opportunity to enjoy as a family home or build your dream estate. A seamless blend of classic design and modern functionality, the home features a private main-floor office with custom millwork, built-ins, and a wet bar-ideal for today's work-from-home lifestyle. The grand open-to-above foyer boasts soaring 18-ft ceilings and leads into a well-appointed kitchen with a large pantry and breakfast area, overlooking the great room with a gas fireplace and adjacent sunroom. The formal dining and living rooms flow effortlessly together, filled with abundant natural light. The second level offers four spacious bedrooms, three updated bathrooms, and the convenience of upper-level laundry. The third floor retreat includes an additional bedroom with a walk-in closet and a renovated 4-piece bathroom with ample storage-perfect for guests or extended family. Designed for entertaining, the fully finished basement features a home theatre, billiards room, wet bar, and additional bathroom. Outdoors, enjoy a professionally landscaped backyard complete with a pool, built-in BBQ, and mature privacy trees, creating a serene private oasis. Car enthusiasts will appreciate the 4-car garage, complete with a home gym. A truly exceptional offering in a premier location. Luxury Certified. More details
    Listed by RE/MAX ESCARPMENT REALTY INC.
  • 94 George Street in Oakville: 1013 - OO Old Oakville Commercial for sale : MLS®# W12406811

    94 George Street 1013 - OO Old Oakville Oakville L6J 3B7
    Main Photo: 94 George Street in Oakville: 1013 - OO Old Oakville Commercial for sale : MLS®# W12406811
    $5,500,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    W12406811
    Total Area:
    5,606 sq. ft.
    Located in the heart of Downtown Oakville's Towne Square, this highly recognizable 5,606 square-foot building at 94 George Street is an exceptional opportunity for investors and end-users or a combination of both. This prominent two-level retail and commercial property features 62 feet of frontage onto Towne Square and is anchored in a prime location featuring high end retail and restaurants. The flexible floor plan allows for a configuration of one to six units, with some currently set up for retail and others for restaurant use with existing kitchen, seating, and patios. The building is zoned Central Business District (CBD), which offers a wide range of permitted uses. Surrounded by top retailers and restaurants, the area is known for its strong demographics, including a high-income household base, and benefits from high pedestrian traffic driven by its charming lakeside appeal, strong tourism, and a growing residential and employment base. The planned revitalization of Towne Square will further enhance the inviting atmosphere with improved seating, greenery, and other enhanced features, providing an even more adaptable space for community events. The building will be sold vacant. More details
    Listed by CLEARSTREAM COMMERCIAL REAL ESTATE LTD.
    To access this listing,
    please create a free account

  • 74 Howard Avenue in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W12812048

    74 Howard Avenue 1013 - OO Old Oakville Oakville L6J 3Y5
    Main Photo: 74 Howard Avenue in Oakville: 1013 - OO Old Oakville House for sale : MLS®# W12812048
    $5,500,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    W12812048
    Bedrooms:
    5
    Bathrooms:
    4
    This English Country Garden home, framed by a storybook white picket fence, sits on a truly exceptional 100' x 168' lot in Orchard Beach, south of Lakeshore Rd in Old Oakville. Quiet and serene Howard Avenue, just two blocks long, is one of only a handful of streets in Oakville offering unobstructed views of Lake Ontario. Further 74 Howard Avenue enjoys coveted southwest exposure, bathing the home in golden-hour light. Cherished by the same owners for 30 years, this residence has been a wonderful home and location to raise their family. The gardens are simply stunning, with perennial plants, too numerous to mention. The home offers 4+1 bedrooms and features two thoughtfully integrated additions. The first includes a spacious kitchen, office, and principal suite with a gas fireplace. The second is a vaulted, light-filled family room with an additional gas fireplace. This is a wonderful home for dinner parties with a formal dining room and an architecturally charming living room featuring an original well enjoyed wood-burning fireplace. A detached, oversized double garage/coach house with loft has most recently been used as an office. The property offers exceptional flexibility: enjoy as-is, renovate, or redevelop. RL3-0 zoning allows premium lot coverage, with permits in place and transferable to sever and build two homes. Severance approval is based on a conceptual design by John Willmott, Architect, envisioning up to a 3,331 sq ft, 4+1-bedroom residence with a two-car garage. Morning walks deliver breathtaking sunrises by the lake, while the SW exposure provides long, light-filled evenings ideal for indoor-outdoor living. The tree-lined perimeter offers rare privacy. Just a short stroll to downtown Oakville, boutique shopping, fine dining, top-rated schools, and major highways. Premium land offerings in Old Oakville are rare-secure your legacy in one of the GTA's most prestigious settings. Luxury Certified. More details
    Listed by RE/MAX Escarpment Realty Inc., Brokerage and RE/MAX ESCARPMENT REALTY INC.
1-12/22
Data was last updated April 15, 2026 at 06:15 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.