Oakville Homes with 51-99 Approx Age

Oakville Homes with 51-99 Approx Age

Welcome to Oakville, Ontario – a picturesque gem nestled along the shores of Lake Ontario, just a short drive from the bustling city of Toronto. Known for its charming downtown, vibrant arts scene, and lush green parks, Oakville offers a perfect blend of suburban tranquility and urban convenience. With a rich history dating back to the early 19th century, this vibrant community boasts a diverse population and a welcoming atmosphere that makes it an ideal place to call home.

For those seeking homes with character and charm, Oakville's properties built between 51 to 99 years ago offer a unique opportunity to experience the elegance of yesteryear combined with modern comforts. These homes often feature stunning architectural details, such as intricate moldings, hardwood floors, and spacious layouts, all while being situated in established neighborhoods that exude a sense of community. Imagine sipping your morning coffee on a sunlit porch or hosting gatherings in a beautifully landscaped yard, all within the serene backdrop of Oakville's tree-lined streets.

Living in Oakville means enjoying easy access to top-rated schools, boutique shops, and gourmet dining options, not to mention the stunning waterfront parks and recreational facilities that encourage an active lifestyle. Whether you’re a young family, a professional, or looking to retire in style, Oakville’s homes from the mid-20th century offer a delightful blend of history and modern living. Come discover the charm of Oakville, where your dream home awaits!

Newest Oakville Homes with 51-99 Approx Age

$1,098,000
3 Beds ⋅ 1 Baths ⋅ W13803122 MLS
Welcome to the heart of Bronte! Situated on a quiet crescent just a short walk from the beautiful shores of Lake Ontario and the charming Bronte Village, this storey-and-a-half home offers an exceptional location and exciting potential. Enjoy nearby waterfront walking trails, local beaches, parks, shops and restaurants, all just minutes from your doorstep. Set on a very private lot with a generous building envelope, the existing home is both comfortable and highly livable. The main level features a bright front living area with large windows that fill the space with natural light, an eat-in galley kitchen and a convenient main-floor bedroom. Hardwood flooring extends throughout the main and upper levels, while the main bath features a newer walk-in, spa-like tub. The kitchen is equipped with a brand-new dishwasher, and the existing fridge, stove, washer and dryer are all currently in working condition and are being sold in "as is" condition. Upstairs, you'll find two generously sized bedrooms, providing excellent space for a growing family, guests or a home office. The property also includes a separate single-car garage with hydro. Whether you're looking for a single-family home in a fantastic lakeside community, an opportunity to add onto the existing residence, or the potential for a complete new build, this property offers exciting possibilities. With its prime Bronte location, private setting and excellent potential, this is an opportunity not to be missed. One of the few homes currently available for sale in this sought-after area!

243 Jennings Crescent, Oakville
$865,000
4 Beds ⋅ 2 Baths ⋅ W13799910 MLS
Spacious and beautifully maintained, this 4-bedroom, 4-level back-split offers over 2399 sq. ft. of total living space, set on a 35 x 125 ft. lot in a prime Oakville neighbourhood. The main level features hardwood flooring throughout the principal living areas. The kitchen is open to the family living space and overlooks the formal dining and living rooms, creating a bright, connected layout with a centre island and breakfast bar. The upper level offers 3 well-appointed bedrooms with closets and a full bathroom. The ground level showcases a converted sunroom with large windows, a gas fireplace, and its own separate entrance, creating excellent potential for an in-law suite, private home office, or guest retreat. An additional living room with hardwood flooring, a fourth bedroom, and a full bathroom complete the level, with direct access to the impressively sized, fully fenced rear yard. Exceptionally well maintained, the home has also benefited from significant recent mechanical updates, including a newer furnace (2026), air conditioner (2026), and electrical panel (2026).The location offers exceptional everyday convenience, with highly rated IB schools, Sheridan College, Oakville Golf Club, Oakville Place, restaurants, parks, and trails all nearby, along with easy access to the Oakville GO, QEW, and major commuter routes.

1237 REDBANK Crescent, Oakville
$1,199,900
4 Beds ⋅ 2 Baths ⋅ W13797664 MLS
LOVINGLY MAINTAINED BUNGALOW IN THE HEART OF OAKVILLE'S DOWNTOWN CORE! MASSIVE 150' DEEP LOT WITH AN INGROUND POOL! ELEVATOR! An excellent opportunity to enjoy exceptional outdoor space, comfortable bungalow living, and an enviable location. Situated on an impressive 150' deep lot, this charming home offers a wonderful blend of indoor and outdoor living, with a beautifully landscaped backyard designed for summer enjoyment and relaxation. The main level features open concept living and dining rooms, a spacious kitchen, primary bedroom with walkout to a sunroom with direct backyard access, two additional bedrooms (one with hardwood flooring), and a four-piece bathroom. An elevator adds valuable accessibility and convenience, while a second sunroom off the garage provides additional flexible space. The partially finished basement offers a large recreation room with a brick floor-to-ceiling woodburning fireplace, den/fourth bedroom, laundry/utility room, and three-piece bathroom with an oversized walk-in shower. Updates include furnace (2022), roof (2013), and electrical and plumbing (1999). The inviting and private backyard is the true highlight, featuring an inground pool with a concrete surround, interlock patio, raised deck, beautiful garden, and mature hedges creating a wonderfully secluded setting for relaxing, entertaining, and enjoying warm summer days. Parking for 10 vehicles includes two spaces in the attached garage and eight on the driveway. Ideally located just steps from Oakwood Public School, parks, Sixteen Mile Creek, and the shops and restaurants of Kerr Village, with the Oakville Centre for the Performing Arts, downtown, lake, transit, highways, and GO Station all close by. A truly special downtown Oakville setting offering privacy, a pool, and an exceptional outdoor lifestyle. (certain exterior photos have been digitally enhanced to showcase potential landscaping possibilities)

305 Queen Mary Drive, Oakville
$850,000
5 Beds ⋅ 2 Baths ⋅ W13794226 MLS
Welcome to 1272 Pallatine Drive in Oakville's highly desirable College Park community. This semi-detached backsplit features five bedrooms, two full bathrooms, a separate main-floor laundry room, and a private drive. Offers 1,733 sq ft plus 378 sq ft basement. This property is close to Montclair Public School, White Oaks Secondary School, and Sheridan College. It offers convenient access to the highway and is a short drive to the GO station.

1272 Pallatine Drive, Oakville
$1,349,888
4 Beds ⋅ 2 Baths ⋅ W13791408 MLS
Seize this rare opportunity to own a beautifully updated 4-level backsplit with a full basement and true double-car garage, ideally situated on a quiet, family-friendly street in highly sought-after West Oakville. Welcome to 2033 Saxon Road, offering over 2,300 sq. ft. of spacious and versatile living space designed with growing families in mind. The main level features a stylish, updated kitchen with modern cabinetry, stainless steel appliances, additional pantry storage, and convenient access to the backyard. Bright, open-concept living and dining areas provide the perfect setting for everyday living and entertaining, with a walkout to the rear patio, gazebo, and beautifully landscaped yard. Upstairs, you'll find a generous primary bedroom, two additional bedrooms, and a refreshed main bathroom. The lower level offers a warm and inviting family room with a gas fireplace, a 3-piece bathroom, and a laundry/utility room with a separate walk-up entrance to the backyard. The finished basement adds even more flexibility with a fourth bedroom, recreation area, and additional space ideal for a home office, gym, teenagers, or extended family. Step outside and enjoy your own private backyard retreat, complete with a spacious gazebo, expansive patio area, beautifully landscaped gardens, a tranquil water feature, and an above-ground pool-perfect for summer entertaining and family enjoyment. Conveniently located close to Bronte GO Station, excellent schools, the Queen Elizabeth Park Community and Cultural Centre, shopping, restaurants, transit, and everyday amenities. Enjoy being within walking distance of Bronte Harbour and Bronte Creek Lands Park while coming home to the peace and privacy of a quiet crescent in one of West Oakville's most desirable neighbourhoods. A wonderful family home offering space, comfort, and an exceptional location-this is one you won't want to miss!

2033 Saxon Road, Oakville
$1,449,900
4 Beds ⋅ 3 Baths ⋅ W13790452 MLS
Tucked away at the end of a quiet cul-de-sac in a family-friendly South-West Oakville neighbourhood, this beautifully renovated 4-bedroom home offers the character of an established property with the comfort of a thoughtfully updated interior. Taken down to the studs and extensively renovated from top to bottom in 2022, updates include: vinyl siding, newer roof, electrical, plumbing,windows, floors, doors and so much more!! A huge, wrap-around front porch welcomes you inside, where oversized windows flood the home with natural light. Freshly painted throughout in soft, neutral colours. Beautiful hardwood and tile flooring throughout.The main floor offers a bright Living Room with views of the gardens, open-concept Dining Room opens to the cozy Family Room with gas f/p, and eat-in kitchen with centre island, perfect for casual meals and entertaining. Upstairs, the Primary Bedroom features a 2-piece ensuite, while three additional bedrooms share a beautifully finished 4-piece bath. The finished lower level adds even more living space with a Recreation area,with wood-burning fireplace, reclaimed brick surround & extensive built-ins. Additional Games Room, huge cold cellar & oversized Utility Room/Laundry area and workshop. Outside is where this property truly shines. The private, fenced backyard is surrounded by mature trees and stunning, perennial English gardens, backing onto the natural beauty of Fourteen Mile Creek. Cobblestone patios and pathways wind through the gardens, while a huge covered rear deck and charming gazebo create wonderful spaces for outdoor dining, entertaining or simply enjoying the peaceful setting. Complete with a 2-car garage and located in a sought-after school district, this exceptional South-West Oakville home offers space, privacy, beautiful natural surroundings and an extensively updated interior. Close proximity to the Lake, and easy access to all major highway. Meticulously maintained, this truly is a move-in ready home!!

1252 Wood Place, Oakville
$1,159,000
6 Beds ⋅ 2 Baths ⋅ W13788524 MLS
3+3 bedrooms Bungalow with separate entrance in College Park area. Renovated throughout with an eat-in kitchen, open-concept living/dining, spacious 3 bedrooms, a granite 4-pc bath, and laundry on the main level. Professionally finished lower level offers 3 bedrooms, Eat in kitchen, living room, 3 pc bath and laundry. Walking distance to Sheridan College, French Immersion Public & Catholic Elementary and High Schools, Oakville Place, Library & Parks. Just minutes to QEW, 403, 407 & Go Transit access.

35 Culham Street, Oakville
$980,000
3 Beds ⋅ 2 Baths ⋅ W13781814 MLS
Welcome to this charming 1.5 storey home, ideally situated in a convenient and sought-after Oakville location! With 3 bedrooms and 2 bathrooms, this inviting home offers a functional layout with an open-concept kitchen overlooking the living room, creating a bright, connected space for everyday living and entertaining. A versatile main-floor office or den provides the perfect setting for working from home, a quiet study space or an additional living area. Ideally located just moments from vibrant Kerr Village, enjoy easy access to an excellent selection of local shops, cafés, restaurants and everyday amenities. Parks, recreation facilities and the Lake Ontario waterfront are also nearby, while Downtown Oakville, Oakville GO Station and major commuter routes are all within easy reach. Don't miss out on this wonderful opportunity! Property is being sold under Power of Sale. Sold as is, where is.

7 Washington Avenue, Oakville
$3,175,000
3 Beds ⋅ 4 Baths ⋅ W13775010 MLS
This bespoke architecturally designed single-storey residence, created in the Contemporary Shed Style, combines refined architecture with exceptional functionality and craftsmanship. Designed for sophisticated entertaining and comfortable family living, the home features dramatic interior rooms, clean lines, and seamless indoor-outdoor connections. Principal living spaces and bedrooms are positioned to maximize privacy and natural light through expansive floor-to-ceiling windows overlooking landscaped gardens. A generous foyer introduces over 3,100 sq. ft. of refined single-level living. At the heart of the home, a striking four-sided wood-burning fireplace connects the formal living and dining areas. The gourmet kitchen is equipped with premium appliances, sky-lighting, custom cabinetry, walk-in pantry storage, and built-in serving functions, while oversized glass doors open directly to the gardens and outdoor entertaining spaces. The adjoining family room is filled with natural light from extensive glazing and skylights, complemented by wide plank white oak flooring, custom millwork, and cathedral tongue-and-groove willow ceilings. The private primary suite includes a spa-inspired ensuite, walk-in closet, and direct garden access. Two additional bedrooms feature oversized windows and double closets. The lower level offers excellent versatility with a recreation room, oversized laundry and craft area, workshop, cedar storage room, and wine storage. Completing the property are a cedar shake roof, cobblestone driveway, double carport, and oversized double garage with parking capacity for up to seven vehicles, delivering a rare blend of luxury, comfort, and practicality.

1168 Carey Road, Oakville
$459,900
2 Beds ⋅ 1 Baths ⋅ W13773690 MLS
Welcome to Arbour Glen in the heart of Kerr Village! This spacious, professionally measured 930sq. ft. two-bedroom suite offers comfortable living today and an exciting opportunity topersonalize over time. Located on the ninth floor, the unit features an exceptionally generousliving and dining area, wall-to-wall windows providing an abundance of natural light, afunctional galley kitchen, two well-proportioned bedrooms and excellent in-suite storage.Lovingly maintained, the suite provides a wonderful canvas for buyers looking to update andcreate a home that reflects their own style. Set on beautifully landscaped grounds in anestablished condominium community, you are within walking distance of Kerr Village shops, cafésand restaurants, Trafalgar Park Community Centre, downtown Oakville, the lakefront and scenicwaterfront trails. Public transit is nearby, with convenient access to the Oakville GO Stationand major highways. An excellent opportunity for first-time buyers, downsizers or renovatorsseeking generous space, value and a highly walkable Oakville lifestyle.

212 Kerr Street Unit 906, Oakville
$1,665,000
5 Beds ⋅ 2 Baths ⋅ W13773634 MLS
Welcome to this stunningly renovated 3+2 bedroom set on an expansive mature lot in one of Oakville's most coveted neighbourhoods, just moments from the shores of Lake Ontario. Surrounded by majestic trees in front providing that extra security and stunning view, 2066 Rebecca Street boasts exceptional curb appeal & a welcoming foyer highlighted by elegant wood staircases. The home is filled with massive windows &patio doors throughout, picturesque green scenic views from nearly every room. The sun-filled living room features oversized windows & potlights throughout, seamlessly flowing into the open-concept living, dining & kitchen spaces, perfect for both everyday living & entertaining. The beautifully appointed kitchen offers stainless steel appliances, Skylight, abundant cabinetry & a charming breakfast nook. Unwind in the inviting family room with a cozy fireplace & walk-out to a private, fully fenced backyard oasis complete with a wooden patio & storage shed, ideal for summer gatherings. Main floor office provides the perfect work-from-home setup. The main level features 3 generously sized bedrooms, including a luxurious retreat with a spa-inspired 4-pc bath & wrap-around balcony overlooking the tranquil surroundings. The fully finished basement with a separate walk-up entrance offers incredible versatility with 2 additional bedrooms, walk in closet, a spacious rec room, family room, 3-pc bath, utility room & laundry area, ideal for extended family or in-law potential. The raised walk-out basement features large windows that allow an abundance of natural light, creating a bright & inviting lower level. It also includes provisions for a future kitchen with plumbing &stove setup already in place, offering excellent potential for multi-generational living or added convenience. Perfectly situated close to schools, parks, shopping & the lakefront, this exceptional home offers the perfect blend of elegance, comfort, & convenience for today's modern family.

2066 Rebecca Street, Oakville
$1,849,900
3 Beds ⋅ 3 Baths ⋅ W13773492 MLS
Discover this beautifully upgraded bungalow in one of Oakville's most desirable locations, just a short walk to Kerr Village and downtown Oakville. Thoughtfully designed for easy, comfortable living, the home offers a bright open-concept layout with a modern kitchen overlooking spacious living, dining, and family areas, perfect for everyday life and entertaining (two dishwashers!).The main level features two bedrooms and 1.5 baths, with the flexibility to create a private primary retreat. The finished basement adds valuable living space for guests, a home office, hobbies, or family time. Outside, the beautifully landscaped backyard is a true extension of the home, complete with a built-in pool added in 2020. It's a wonderful setting for summer afternoons, relaxed evenings, and entertaining friends and family. An ideal opportunity for downsizers looking to enjoy single-level living without giving up space, a finished basement, or a beautiful backyard. Equally well suited to a young family, this is a home that offers flexibility for years to come. With its thoughtful updates, inviting layout, private outdoor space, and walkable location close to shops, restaurants, parks, and the lake, this is a rare opportunity in the heart of Oakville.

278 Carolyn Drive, Oakville
Start Your Search