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

$2,498,000
3 Beds ⋅ 3 Baths ⋅ W13815744 MLS
If you're a buyer looking in Morrison under the $2.5M mark, you may be finding your options to be a little...complicated. At this price point, properties tend to fall somewhere along the axis of land or house. Finding one where you have a compelling case for both is considerably harder.So, first things first. Buy on the best street you can afford. This is where Donlea delivers. A genuinely quiet street, beautiful homes, right at the heart of the neighbourhood and with schools close enough for the children to walk themselves. Frankly put, it's ideal.Then there's the land. With a new survey available, this west-backing 93' x 185' lot with stream offers the potential to build approximately 5,200 sq. ft. For those looking to create their forever home, it's a rare opportunity to secure a substantial piece of land in one of Oakville's premier neighbourhoods.But it would be remiss not to acknowledge that there is also a great deal of house here to love - and renovate.The existing 3,263 sq. ft., four-level side-split is surprisingly generous, with large bedrooms, a double garage and plenty of scope to reimagine the spaces. Think contemporary interiors, wall-to-wall windows and a seamless floorplan, all while retaining the scale and character that make this house work. A fantastic opportunity for those who want to control their budget while creating equity. In other words, you have options. Build new. Renovate. Or simply take your time and decide what makes the most sense for you.With this kind of flexibility, the upside is yours to create.

1242 Donlea Crescent, Oakville
$1,949,000
4 Beds ⋅ 3 Baths ⋅ W13814998 MLS
How do you have it all for under $2M in downtown Oakville? Answer: Buy Smart! In this price range there are four key items that should be at the top of your list: LOCATION, GARAGE, LIVING SPACE, FINISHES. Finding all four in one home? That's the challenge and this is where Tavistock delivers. LOCATION: Nestled on a private cul-de-sac just steps from downtown and the lake, on a generous 102' x 124' west-backing lot. Add mature trees, quality neighbours and top nearby schools and the location becomes difficult to improve on.GARAGE: A double garage is a very rare find in this price range and an absolute must for protecting one's investment and joy! LIVING SPACE: With more than 2,400 sq ft above grade Tavistock delivers. The 20' x 20' family room is a standout; a space that truly sets Tavistock apart! While the four-bed layout offers flexibility. There's even a separate entrance should you want to create a private living arrangement for someone in your life. FINISHES: Completely renovated throughout with updated mechanicals, electrical, windows, appliances, flooring, trim, fixtures, cabinetry and more. In other words, the expensive work has already been done. And that's really the point.Location, Living Space, Double Garage and Quality Finishes remarkably difficult features to find under $2M Fortunately 130 Tavistock delivers on them all!

130 Tavistock Square, Oakville
$1,950,000
4 Beds ⋅ 4 Baths ⋅ W13814358 MLS
Welcome To One of Falgarwood's Most Exceptional Properties, Perfectly Positioned on a Premium 75' X 150' Ravine Lot Backing Directly onto Morrison Valley South. This Fully Renovated Four-Bedroom Executive Home Offers a Rare Blend of Luxury, Privacy, & Everyday Comfort. Surrounded by Mature Trees and Spectacular Ravine Views, Retreat to Your Own Backyard Oasis Where Nature Becomes Part of Your Everyday Lifestyle. The Beautifully Renovated Interior Showcases Rich Hardwood Flooring, Spacious Principal Rooms, and a Stunning Chef-Inspired Kitchen with Quartz Countertops, Stainless Steel Appliances, and a Large Centre Island. The Inviting Family Room with a Gas Fireplace Overlooks the Breathtaking Ravine. While the Upper-Level Features Four Generous Bedrooms, including a Luxurious Primary Retreat with a Spa-Inspired Ensuite, Walk-In Closet, Vaulted Ceiling, & Gas Fireplace. The Professionally Finished Walk-Out Basement Adds Exceptional Living Space with a Theatre Room, Gym, And Direct Access to Your Private Outdoor Retreat. Unwind in the Heated Inground Pool with Waterfall, relax in the Hot Tub, Entertain on The Expansive Patios, or Simply Enjoy the Peace & Tranquility of One of Falgarwood's Most Coveted Ravine Settings. Minutes to Top-Rated Schools, Parks, Trails, Sheridan College, GO Transit, Shopping, & Major Highways. A Truly Rare Opportunity in One of Oakville's Most Desirable Neighbourhoods.

1302 Hillview Crescent, Oakville
$1,620,000
4 Beds ⋅ 3 Baths ⋅ W13808938 MLS
Welcome to 2039 Wakely Street-a rare opportunity to enjoy, renovate or build your dream home on an impressive 75 x 150 ft. lot in sought-after Southwest Oakville. Surrounded by beautiful custom-built residences, this RL2-0-zoned property offers the potential to accommodate a custom home of at least 4,100 sq. ft. The main floor features open-concept living and dining areas, a well-equipped kitchen and a versatile bonus room ideal for a home office or additional bedroom. Hardwood flooring, large windows overlooking the front and side yards, smooth ceilings and modern pot lights create a bright, welcoming atmosphere. The kitchen offers stainless steel appliances, including a six-burner gas range. Upstairs, three well-appointed bedrooms feature hardwood flooring, smooth ceilings and modern light fixtures, complemented by a recently updated four-piece bathroom. The lower level provides a spacious recreation room with a cozy gas fireplace, a three-piece bathroom and a dedicated laundry room. The west-facing backyard is perfect for enjoying the in-ground pool and abundant afternoon sunshine with family and friends. A well-maintained lawn and mature trees create a comfortable outdoor retreat. Ideally located just minutes from the lake, shops, GO Transit, parks, coveted schools and Downtown Oakville. An exceptional opportunity to move in, renovate or build for the future. Buyers to verify zoning, building potential and all applicable municipal requirements.

2039 Wakely Street, Oakville
$999,000
4 Beds ⋅ 2 Baths ⋅ W13806874 MLS
OPPORTUNITY KNOCKS IN WEST OAKVILLE! An exceptional chance for first-time buyers, renovators, investors and contractors to get into one of Oakville's established neighbourhoods at an attractive price point. This solid brick bungalow is ready for its next chapter and offers tremendous potential to renovate, reimagine or create a home tailored to your own style.Set on a generous 60' x 100'+ lot, the home features 3+1 bedrooms, 2 bathrooms, an attached double garage, parking for up to 6 vehicles and approximately 1,312 sq. ft. above grade, plus a finished lower level with a separate walk-up. Several important components have already been updated, including the roof (2025), furnace (2018) and central air conditioning (2018). The interior requires updating and is being offered accordingly, providing an excellent opportunity to renovate, add value and build equity. FANTASTIC WEST OAKVILLE LOCATION! Families will appreciate nearby schools including Gladys Speers Public School, St. Dominic Catholic Elementary School and T.A. Blakelock High School. Enjoy convenient access to the Queen Elizabeth Park Community & Cultural Centre, along with nearby parks, playgrounds and trails.Just minutes from Lake Ontario, Bronte Village and Bronte Harbour, enjoy waterfront parks and trails, the marina, restaurants, cafés and shops along Lakeshore Road. Commuters will appreciate convenient access to Bronte GO, the QEW and major routes throughout Oakville and the GTA.A detached Oakville bungalow on a generous lot with a double garage, major mechanical updates and outstanding renovation potential - bring your ideas, build equity and make it your own. Offers welcome anytime!

2490 Yarmouth Crescent, Oakville
$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
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