Oakville Homes with 100+ Approx Age

Oakville Homes with 100+ Approx Age

Welcome to Oakville, Ontario – a charming lakeside gem that beautifully marries rich history with modern living. Nestled along the shores of Lake Ontario, Oakville is renowned for its picturesque waterfront, vibrant arts scene, and lush green spaces. With a population that embraces diversity, this town offers a warm, welcoming atmosphere that appeals to families, young professionals, and retirees alike.

One of Oakville's most enchanting features is its collection of homes with an impressive age of 100 years or more. These historic residences, often characterized by their stunning architecture and unique craftsmanship, tell the story of Oakville's past while providing modern comforts. Walking through neighborhoods like Old Oakville, you’ll find beautifully preserved Victorian and Edwardian homes, each with its own character and charm. These properties not only offer a glimpse into the town’s heritage but also provide a sense of community that is hard to find in newer developments.

Living in Oakville means enjoying a blend of urban conveniences and serene natural surroundings. Residents have access to top-rated schools, boutique shopping, and an array of dining options, all while being just a short drive from bustling Toronto. With its strong community spirit, excellent recreational facilities, and scenic parks, Oakville is the perfect place to call home. Whether you’re drawn to the allure of historic homes or the vibrant lifestyle, Oakville invites you to explore its timeless beauty and find your dream residence amidst its storied streets.

Newest Oakville Homes with 100+ Approx Age

$2,398,900
3 Beds ⋅ 4 Baths ⋅ W13767320 MLS
Welcome to 433 Allan Street, a distinctive residence designed for effortless living offering a perfect blend of timeless sophistication and low maintenance convenience set privately behind gates on a professionally landscaped tree lined lot. Newly renovated, spacious 9ft ceilings throughout and skylights create a bright inviting atmosphere including rich hardwood floors, custom millwork and built in cabinetry. The chef inspired kitchen features premium Bosch appliances, generous island and an inviting living room anchored by a striking fireplace. Wake up to the morning sunrise as the primary suite is a tranquil retreat with high ceilings, skylights, a spa-inspired ensuite including make up vanity, heated floors and a private outdoor living space overlooking the private grounds. A second bedroom, additional bathroom with heated floors and discreet stacked laundry alcove complete the main level with exceptional convenience. Entertain in style with a premium outdoor kitchen in a stunning alfresco setting with your own pizza oven and fire bowl. A finished lower level, featuring a third bedroom, full bathroom, kitchenette, laundry room, private courtyard and a separate walk up entrance offers flexibility for family and guests. Just steps outside, a detached garden suite with garage complete with bedroom, bathroom, kitchenette and private courtyard adds rare versatility for guests, extended family, a studio, home office, nanny suite or gym. A carport and ample parking for 10+ vehicles further enhance the property. Additional features include new windows 2023, hot tub and artificial turf. Offering just over 1375 square feet of living space with an additional 374 square feet in the garden suite. The best of downtown Oakville's lifestyle living is just steps away from waterfront, marina, parks, boutiques,restaurants,GO Station,Whole Foods,major highways and sought after schools. A rare opportunity to own a turn key property offering privacy and character in SE Oakville.

433 Allan Street, Oakville
$1,899,900
5 Beds ⋅ 1 Baths ⋅ W13721624 MLS
This residential property in North Oakville presents a unique redevelopment opportunity. Buyers can renovate and occupy the existing home, rent it out, or explore rezoning options to unlock its full potential (construction of up to 8 story residential building). Located at the prime intersection of Dundas and Bronte, it offers easy access to a range of amenities, making it an ideal investment or project for the future. Please note: seller is willing to entertain a vendor take back mortgage!

2527 Dundas Street W, Oakville
$2,599,000
5 Beds ⋅ 3 Baths ⋅ W13716436 MLS
South East Oakville Home Dream. Nestled on a premium, light-filled south-facing lot on Palmer Avenue, this beautifully updated heritage home seamlessly blends timeless architectural character with modern comforts. Every space has been thoughtfully updated to maximize natural light and highlight effortless flow throughout the residence. The main level showcases rich plank flooring, expansive formal living and dining spaces, and a welcoming great room anchored by a stunning Rumford fireplace. The kitchen features clean line sand timeless craftsmanship for a busy family featuring an additional dishwasher and luxurious heated floors paired with a highly functional rear galley pantry for exceptional storage. A main-floor fifth bedroom serves as an ideal guest suite or private home office. Upstairs, the expansive primary suite acts as a private sanctuary with its own Rumford fireplace, walk-in closet and private 5 piece ensuite. A second floor laundry, and three additional spacious bedrooms complete the upper level. Downstairs, the finished lower level offers versatile space perfectly suited for a media room, home gym, or play area along with ample storage. The backyard settles in with old world charm enjoying a south-facing private retreat featuring two oversized decks, one covered, designed for entertaining amidst mature, lush grounds. Complete with major mechanical updates-including a newer furnace, central A/C, and an owned hot water tank-this distinguished home offers total peace of mind. Located just steps from downtown Oakville, the lake, top-ranked schools, and scenic parks, this is a rare opportunity to own a turnkey heritage property in one of Oakville's most coveted neighborhoods.

332 Palmer Avenue, Oakville
$2,099,000
5 Beds ⋅ 2 Baths ⋅ W13637112 MLS
**An exceptional opportunity to secure one of Old Oakville's most desirable building lots.** Situated on prestigious Douglas Avenue, this rare **48' x 150'** property offers the perfect canvas to create a custom luxury residence in one of Oakville's most sought-after neighbourhoods. Flat, private, and free of significant obstructions, the lot provides outstanding design flexibility for your dream home. Located in the heart of Old Oakville, you'll enjoy an unbeatable lifestyle just steps to vibrant downtown Oakville, boutique shopping, renowned restaurants, cafés, parks, the lakefront, and the Oakville GO Station, with convenient access to major highways. Opportunities to acquire premium building lots this close to downtown are exceptionally rare. Whether you're an end user ready to build your forever home or a builder seeking a premier location, this is a property that offers both exceptional value and limitless potential. Experience the charm, prestige, and walkable lifestyle that make Old Oakville one of the GTA's most coveted communities. A truly rare offering in an irreplaceable location.

235 Douglas Avenue, Oakville
$999,999
4 Beds ⋅ 2 Baths ⋅ W13528986 MLS
Welcome to 135 Deane Ave, where modern comfort meets the charm of Kerr Village. Just a short stroll from local cafes, boutique shops, and the shores of Lake Ontario, this beautifully renovated bungalow invites you to slow down and feel at home. Step into the sun-filled four-season sunroom, wrapped in windows and natural light - the perfect spot for morning coffee as the neighbourhood comes to life. From there, the home opens into a warm and welcoming living and dining space, anchored by an exposed brick fireplace that tells its own story of character and comfort. At the back of the home, the thoughtfully updated kitchen awaits, complete with quartz countertops, crisp white subway tile, and stainless steel appliances. Whether you're preparing a quiet weeknight dinner or hosting friends, this space flows effortlessly onto a spacious deck overlooking a private, tree-lined backyard - ideal for summer evenings under the stars. Two generous bedrooms and a sleek three-piece bath complete the main level, while a mudroom offers practical everyday convenience and access to the lower level. Downstairs, the fully finished basement expands the possibilities, featuring a large recreation room, two additional bedrooms, a full bath, and a separate entrance with laundry and kitchen rough-ins - ready to be converted into a self-contained unit for guests or extended family. With a detached garage and ample driveway parking, this home is more than a place to live - it's a place to belong.

135 DEANE Avenue, Oakville
$10,900,000
5 Beds ⋅ 5 Baths ⋅ W13430514 MLS
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.

350 King Street, Oakville
$3,850,000
4 Beds ⋅ 4 Baths ⋅ W13018186 MLS
It is rare to find a home that respects its history while boldly defining its future. Set within Oakville's prestigious West Harbour neighbourhood, 55 Chisholm Street is a study in modern heritage, where a century-old stone foundation anchors a home defined by thoughtful design and sustainable innovation. Superior craftsmanship and comfortable, functional spaces create a residence that is both considered and effortlessly livable. Every detail reflects a singular vision. The architecture bridges past and present with quiet confidence, pairing natural plaster walls and custom ironwork with a sculptural three-dimensional stairwell and a professional Valcucine kitchen outfitted with integrated Miele appliances. A striking soapstone fireplace grounds the main living area, while open-concept spaces extend toward landscaped gardens, creating a seamless connection between indoors and out. Its intelligence is expressed through restraint. Geothermal heating, energy-recovery ventilation, and rainwater harvesting are fully integrated, supporting a high level of performance without compromising design integrity. Upstairs, three well-appointed bedrooms and two bathrooms offer calm and privacy. The primary suite opens to a private terrace, while a treetop lookout captures elevated views across the neighbourhood canopy. The lower level includes a modern gym, cedar-lined wine cellar, and guest suite. Outside, the grounds continue the experience with a cedar sauna, outdoor shower, fire pit, and full outdoor kitchen. Steps from the lake and Downtown Oakville, this is a legacy property reimagined for the next century, offering a rare balance of architectural integrity, modern performance, and quiet, enduring livability.

55 Chisholm Street, Oakville
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