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

$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
$2,999,000
5 Beds ⋅ 3 Baths ⋅ W13291708 MLS
Nestled in Southeast Oakville, this beautifully renovated heritage home on Palmer Avenue offers timeless character, modern comfort and an exceptional lifestyle on a premium south-facing lot. Thoughtfully updated while preserving its architectural charm, the residence is filled with natural light and enjoys seamless connections to its private outdoor living spaces. The expansive south-facing backyard is a true retreat, featuring two spacious decks that provide multiple areas for entertaining, and relaxing while overlooking the mature grounds. Inside, the home blends heritage elegance with contemporary functionality. The welcoming great room is anchored by rich plank flooring and a stunning Rumford fireplace, creating a warm and sophisticated atmosphere for everyday living. The kitchen showcases clean lines and timeless design, complemented by a practical rear pantry hallway offering exceptional storage and organization. Large principal living and dining rooms provide generous space for formal entertaining while maintaining a sense of comfort and flow throughout the main level. The upper level offers four bedrooms, including a primary suite that features a Rumford fireplace, walk-in closet and a five-piece ensuite and laundry room The additional large fifth bedroom is on the main floor providing flex space for guests or home office. The finished lower level extends the living space with versatile area ideal for recreation, fitness, media or play, ensuring ample room for every stage of family life. Recent mechanical updates provide peace of mind, including a new furnace, owned hot water tank and central air conditioning. Combining heritage character, thoughtful renovations and an exceptional location in one of Oakville's most established neighbourhoods, this distinguished property offers a rare opportunity to enjoy sophisticated family living just moments from the lake, top-ranked schools, parks, shopping and the vibrant amenities of downtown Oakville.

332 Palmer Avenue, Oakville
$1,848,000
4 Beds ⋅ 3 Baths ⋅ W13215246 MLS
The one you have been waiting for! Situated in the heart of trendy Kerr Village, this exceptional residence perfectly pairs a charming exterior with a thoroughly modernized, high-end interior. The quaint covered front porch welcomes you into an expansive, light-filled foyer boasting high ceilings and double closets. Completely renovated and designed for modern living, the main floor features a spacious bedroom or home office, a stylish powder room, dedicated laundry, and a striking glass-enclosed open staircase. The heart of the home is the spectacular open-concept kitchen, dining, and sunken family room-a show-stopping space with vaulted ceilings, a bricked gas fireplace, floor-to-ceiling windows, and oversized sliders. Upstairs offers two generous bedrooms and a chic 3-piece bath. The fully finished lower level adds incredible versatility with a rec room, additional bedroom/office, and a sleek 3-piece glass shower bath. Outside, an ultra-private, fully fenced backyard oasis awaits, complete with a tiered wood deck, covered pergola, gas BBQ hookup, and a new garden shed. Walk around the corner to Kerr Street's bustling cafes and restaurants, or downtown Oakville. Exceptional proximity to the QEW and GO Transit. A truly rare find in this desirable and trendy neighbourhood!

119 Westside Drive, 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
$1,999,900
5 Beds ⋅ 1 Baths ⋅ W12936888 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
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