Oakville Homes with 51-99 Approx Age

Oakville Homes with 51-99 Approx Age

Welcome to Oakville, Ontario—a charming town that beautifully marries the tranquility of suburban life with the vibrancy of urban amenities. Nestled along the picturesque shores of Lake Ontario, Oakville is renowned for its stunning waterfront, lush parks, and a rich tapestry of cultural experiences. With its tree-lined streets and historic downtown, this community radiates warmth and charm, making it an ideal place for families, young professionals, and retirees alike.

In Oakville, homes aged between 51 to 99 years old offer a unique blend of character and modern living. Many of these properties boast classic architectural styles, from elegant Tudors to quaint bungalows, each with its own story to tell. These homes often feature spacious layouts, mature gardens, and charming details that reflect the craftsmanship of a bygone era. Living in one of these residences means embracing a piece of Oakville's history while enjoying the comforts of contemporary amenities.

The community is also known for its top-rated schools, vibrant arts scene, and an array of recreational facilities, making it a perfect setting for families. Residents can enjoy leisurely strolls along the waterfront, indulge in boutique shopping, or savor delightful dining experiences in the downtown area. With easy access to major highways and public transit, commuting to nearby cities like Toronto is a breeze.

Discover the allure of Oakville, where the past and present harmoniously coexist, and find your dream home in this enchanting community. Experience the charm of Oakville living today!

Newest Oakville Homes with 51-99 Approx Age

$1,049,900
3 Beds ⋅ 2 Baths ⋅ W13602522 MLS
Welcome to 2145 Sunnyvale Drive, a raised bungalow situated on a 60 x 100-foot lot in the highly desirable Bronte neighbourhood! Offering 3 bedrooms, 2 bathrooms, a double attached garage, and exceptional potential, this is a fantastic opportunity to own in one of Oakville's most sought-after communities. The bright main level features an open-concept kitchen, living, and dining area with hardwood flooring and large windows that fill the home with natural light. Whether you're a first-time buyer, downsizer, or investor, the functional layout provides an excellent foundation to make the space your own. The fully finished lower level offers incredible flexibility, with a spacious family room, a recreation room complete with a wet bar, a second kitchen, and ample space to adapt the layout to suit your lifestyle. Step outside to enjoy the peaceful backyard, offering endless possibilities for gardening, outdoor entertaining, a children's play area, or simply relaxing in your own private green space. Recent updates include a new roof (2025) and fresh paint throughout (2026). Located within a highly regarded school district and just steps to parks, playgrounds, and everyday amenities, this home offers an exceptional lifestyle. Enjoy scenic walking and cycling trails, peaceful strolls to the shores of Lake Ontario, and easy access to Bronte Harbour, Bronte Beach Park, boutique shops, cafés, restaurants, and the vibrant downtown Oakville waterfront. Commuters will appreciate the quick access to the QEW and Bronte GO Station. Offering incredible value, an unbeatable location, and endless potential, this is your opportunity to make a home your own in the heart of Bronte.

2145 Sunnyvale Drive, Oakville
$3,198,000
4 Beds ⋅ 3 Baths ⋅ W13599614 MLS
Set on a high sought-after, tree-lined street in the heart of Old Oakville, this beautifully renovated residence offers refined, move-in ready living in one of the town's most coveted neighbourhoods. Bright, sophisticated interiors are defined by wide-plank white oak floors, clean architectural lines and an effortless connection to the outdoors.At the heart of the home, the custom kitchen features sleek cabinetry, quartz countertops, premium appliances and a beverage fridge, flowing seamlessly into the breakfast area and inviting great room. A striking three-sided gas fireplace creates a natural focal point, while expansive four-panel Kolbe sliding doors open to a private backyard designed for everyday enjoyment and exceptional entertaining.The professionally landscaped gardens offer a true outdoor retreat, complete with a spacious lounge centred, dining terrace, built-in outdoor kitchen with gas barbecue and beverage fridge, mature privacy plantings and a generous lawn.The upper floor offers three well-proportioned bedrooms, including a tranquil primary suite overlooking the gardens with a walk-in closet and beautifully appointed five-piece ensuite featuring double vanities, a soaker tub and glass shower. Two additional bedrooms and a family bathroom complete this level.The finished lower level, with its side entrance, adds exceptional flexibility with a fourth bedroom, recreation room and versatile space ideally suited for a home office, gym or guest accommodation.Perfectly positioned just moments from the lake, downtown Oakville, the New Central Public School, Oakville Trafalgar High School, Whole Foods, the GO Station, and exception recreation facilities and parks. This is a rare opportunity to enjoy an outstanding home in one of Oakville's most established and sought-after neighbourhoods.

303 Watson Avenue, Oakville
$6,975,000
3 Beds ⋅ 3 Baths ⋅ W13594134 MLS
Lakefront home, nestled on Old Oakville's Second Street, this residence offers a blend of timeless elegance, luxury, and unparalleled waterfront living. Completely reimagined top to bottom, showcasing an aesthetic designed for both family living and comfortable downsizing. Bathed in natural light, offering breathtaking lake views from nearly every room, you will find tranquility and grandeur from the moment you enter. Glowing hardwood flooring, custom millwork and paneling, recessed lighting, and designer finishes elevate every space.The kitchen, with panoramic lake views, features custom cabinetry, integrated top-of-the-line appliances, and an oversized island with seating for four. Quartz countertops and full-height quartz backsplash create a striking focal point, complemented by gold pendant lighting.The living room is designed for both comfort and style, featuring custom built-in cabinetry with illuminated shelving, gas fireplace, and expansive windows framing the sparkling waters of Lake Ontario. The main-floor primary suite, spacious and serene, featuring a walk-in closet. Spa-inspired ensuite with a freestanding soaker tub, glass walk-in shower, vanity, and gold fixtures and lighting. Two additional bedrooms on the upper level for family and guests, with private balcony overlooking the waterfront. Enjoy a beautifully appointed main-floor laundry room with custom cabinetry and stacked appliances. Enjoy riparian rights from a spectacular waterfront deck featuring glass railings and steps to the shoreline. Maximizing the panoramic water views, an unrivaled setting for entertaining, relaxing, and embracing Oakville's most prestigious waterfront lifestyle. Complete with a detached 2 car garage and ample private parking. Furniture by FOR living, Art by Harbour Gallery. Luxury Certified.

21 Second Street, Oakville
$2,049,000
4 Beds ⋅ 4 Baths ⋅ W13590468 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
$1,690,000
5 Beds ⋅ 2 Baths ⋅ W13590300 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
$1,350,000
5 Beds ⋅ 2 Baths ⋅ W13587858 MLS
Welcome home to 2501 Yarmouth Crescent, a charming 3+2 bedroom, 2 bath detached raised bungalow nestled on a quiet, family-friendly street in the heart of prestigious Bronte West. Boasting a bright, open-concept layout over 2,000+ total square feet of functional design, featuring stainless steel appliances, Caesar stone countertops, a raised breakfast bar, and a separate dining area, this home is perfect for seamless family gatherings. The plush, new carpet in the bedrooms adds comfort, while the recently renovated bathrooms offer turnkey convenience. The fully finished lower level expands your living space, complete with two additional large bedrooms, a sprawling family room anchored by the cozy gas fireplace, and a second full bathroom. The tankless water heater and the attached 2-car garage with interior access add value and convenience. Embrace the ultimate outdoor lifestyle in your private backyard oasis, complete with a hot tub, relaxing gazebo, and a gas BBQ hookup ready for summer entertaining. The large, level yard on this 60x105ft lot offers the perfect canvas with plenty of space for a future pool or your very own winter hockey rink. Take a short walk along the tree-lined streets through the beautiful neighborhood to Glen Allen Park, Donovan Bailey Trail, Bronte Creek, and the QEP Community and Cultural Centre. Located minutes from top-rated schools, Highway 403, the GO Station, and the vibrant shops and dining of Bronte Harbour, this property perfectly combines the tranquility and convenience that the Bronte, Oakville community is known for!

2501 Yarmouth Crescent, Oakville
$899,999
3 Beds ⋅ 2 Baths ⋅ W13586052 MLS
Welcome to 374 St. Augustine Drive, a lovingly maintained 3-bedroom home nestled on a generous lot in the heart of Oakville's vibrant Kerr Village. Proudly owned by the same family since new, this immaculate residence is a rare opportunity to own a home meticulously cared for and cherished for decades. Step inside and discover bright, inviting living spaces filled with warmth and timeless appeal. Upgrades include fresh paint throughout and new flooring upstairs, with wood in the living area and brand new carpetting in the spacious bedrooms. Whether you're looking to move right in and enjoy its pristine condition or personalize it over time, this home offers the perfect canvas for your next chapter. The spacious lot provides endless possibilities for outdoor entertaining, gardening, future expansion, or simply enjoying the privacy and green space that's becoming increasingly difficult to find. The location is just as impressive. Kerr Village is one of Oakville's most sought-after communities, celebrated for its charming small-town atmosphere, thriving local shops, cafés and restaurants, beautiful parks, and easy access to the waterfront. Spend weekends exploring nearby Downtown Oakville, strolling the trails along Sixteen Mile Creek, or enjoying the shores of Lake Ontario. Families will appreciate excellent schools, community amenities, and convenient access to the QEW, GO Transit, and public transit, making commuting throughout the GTA effortless.Whether you're a first-time buyer searching for the perfect place to put down roots, a downsizer looking for the ease of a well-maintained home in an established neighbourhood, or an investor seeking exceptional long-term value, 374 St. Augustine Drive delivers outstanding potential in an unbeatable location. Opportunities like this-where pride of ownership, a premium lot, and one of Oakville's most desirable neighbourhoods come together-are truly rare.

374 ST. AUGUSTINE Drive, Oakville
$1,099,900
4 Beds ⋅ 2 Baths ⋅ W13577072 MLS
Looking to move this summer? This family home might just be the one for you. Offering 4 Bedrooms on the upper level, including a large Primary Bedroom with semi ensuite privileges to the updated 4 piece Bathroom. The main level features an efficient, well designed Kitchen with island, a comfortable Dining Room overlooking the private back yard, plus a huge Living Room facing the beautifully landscaped front yard. The large Family Room on the lower level is the perfect place to unwind after a busy day. The high efficiency insert makes the wood burning fireplace a focal point of the room. There is also a 3 piece Washroom on this level, plus the Laundry Area, a large Workshop and a massive Crawl Space with abundant storage. Outside, the back yard is a delight. There is a Deck and a concrete Patio, plus a large Garden Shed. The yard faces west and is very private and serene. The roof was stripped and reshingled with premium Fibreglass Shingles in September 2022. The High Efficiency Lennox Furnace and Lennox Air Conditioner were installed in 2020. Includes Water Softener & Reverse Osmosis system in the Kitchen. The street is very quiet with exceptional neighbours and is located near the Bronte GO station, which is great for commuters. Shopping, schools and parks are also nearby. Not far from Bronte Village, with easy access to the highway, as well as local transit.

556 Trafford Crescent, Oakville
$2,380,000
4 Beds ⋅ 4 Baths ⋅ W13577056 MLS
Welcome to this gorgeous, fully renovated 4-bedroom, 4-bathroom family home nestled in prestigious South West Oakville. Situated on a quiet, tree-lined cres, this exceptional property is just a short walk to the lake, renowned Appleby College, the modern YMCA, Kerr Village, École Pinegrove, and Morden Public School with its gifted program. Set on a beautifully manicured lot of over one-third of an acre (16,038 sq. ft.), this sun-filled residence offers an ideal blend of luxury, comfort, and lifestyle. A welcoming covered porch leads into the traditional center hall layout, showcasing timeless elegance and thoughtful updates throughout. The stunning new walnut kitchen features quartz countertops and backsplash, two sinks with pull-out faucets, two refrigerators, a 5-burner gas cooktop, built-in oven and microwave, and a convenient Unihopper lazy Susan. The kitchen opens seamlessly to a patio and a private, park-like backyard complete with a professionally installed play structure-perfect for family living and entertaining. The main floor offers a convenient bedroom and a beautifully renovated bathroom. The second level features three well-appointed bedrooms, including a spacious primary suite with his-and-hers closets and a charming window seat. The luxurious bathroom showcases double Kohler sinks and a modern design. The finished lower lvl provides additional living space with a generous recreation room featuring pot lights and a gas fireplace, a new bathroom with glass shower, a spacious laundry room, and a utility room with walkout access to the sunroom. Enjoy the convenience of being surrounded by parks, including Coronation Park, nearby skating arenas, community centers, and shopping. This exceptional oversized lot presents a rare opportunity to enjoy a beautifully renovated home today while offering the potential to build a spectacular custom residence of nearly 4,000 sq.ft. in one of Oakville's most sought-after neighbourhoods. Architectural Plans Available.

406 Christina Drive, Oakville
$1,399,900
4 Beds ⋅ 4 Baths ⋅ W13569974 MLS
Fabulous 4-bedroom sidesplit situated on a premium pie-shaped lot on a quiet, family-friendly crescent, backing onto the Queen Elizabeth Park Community Centre. This well-designed home offers an excellent layout with all bedrooms located above grade, while providing great separation of space and privacy across multiple levels. Ideally positioned within walking distance to several highly regarded schools, all located less than 1 km away, this is an exceptional opportunity for families seeking convenience, community, and an outstanding neighbourhood setting.Pride of ownership is evident throughout, with over $170,000 invested between 2019 and 2021 in thoughtfully completed renovations and upgrades designed for long-term enjoyment. The finished basement provides additional living space with a convenient kitchenette, offering flexibility for guests, extended family, a home office, or a variety of lifestyle needs. Improvements include a fully renovated interior featuring new flooring, stairs, kitchen, bathrooms, lighting, and modern finishes, along with significant exterior enhancements including a new furnace (2020), fence (2020), rebuilt deck (2021), front door, sliding glass door, windows (2021), and asphalt driveway (2021). These updates were completed with quality, comfort, and everyday functionality in mind, showcasing a home that has been meticulously maintained and enhanced by owners who truly cared for the property.

444 Withnell Crescent, Oakville
$2,098,000
3 Beds ⋅ 1 Baths ⋅ W13568414 MLS
A truly exceptional and rarely available offering in one of Oakville's most coveted luxury enclaves, this expansive pie-shaped, an extraordinary 17879 sqft parcel presents a premier opportunity for builders, investors, and those seeking to create a landmark custom estate. Surrounded by distinguished multi-million dollar residences, this property is ideally positioned on a quiet, tree-lined street in a neighbourhood defined by upscale redevelopment and architectural excellence. The lot is the true showpiece-boasting a 60 ft frontage that dramatically opens to an impressive 174 ft across the rear, with remarkable depths of approximately 213 ft and 145 ft. This unique configuration offers an extraordinary building envelope, providing the scale and flexibility required to design and construct a truly grand custom home with resort-style outdoor living, without compromise. The existing 3-bedroom residence features an open-concept main living area and a finished lower level with a recreation room and two Murphy beds, a huge backyard with concrete patio, offering comfortable, functional living or rental potential while future plans are realized. Additional features include an attached double garage and an extended private driveway accommodating up to six vehicles. Enjoy an unparalleled lifestyle with a short 20-minute stroll to the lake & coronation park, while everyday conveniences are just a 7-minute walk to a nearby shopping plaza featuring Walmart, LCBO, Metro, Shoppers Drug Mart and major banks. Families will appreciate the proximity to top-rated schools & public library, including Blakelock High School and elementary school, all within a 14-minute walk. This is a rare land acquisition opportunity in prime Oakville-offering unmatched lot dimensions, prestigious surroundings, and exceptional redevelopment potential. Properties of this scale and caliber are seldom offered, making this a standout investment in one of the GTA's most desirable luxury markets.

1332 Stanbury Road, Oakville
$9,500,000
W13562054 MLS
A rare opportunity to acquire a premier downtown Oakville redevelopment asset, ideally positioned for an owner-occupier, investor, or long-term landholder. Occupying 0.58 acres at the high-profile southwest corner of Lakeshore Road West and Kerr Street, just moments from Lake Ontario, this single-tenant property combines exceptional location fundamentals with strong income potential and significant mixed-use redevelopment upside. A new roof was installed in late 2025, and the property further benefits from a filed and acknowledged Record of Site Condition, offering added confidence for sophisticated purchasers and future planning initiatives. Nearby precedent at 42 Lakeshore Road West, two blocks east at Lakeshore Road West and Chisholm Street, further supports the area's intensification trajectory; on the same lot size, the Ontario Land Tribunal approved an 11-storey mixed-use development comprising approximately 142,300 square feet of total gross floor area, 152 residential units, and ground-floor commercial/retail space. Together, the comparable scale, location, and approval history reinforce the subject property's compelling future redevelopment potential. Please refer to the attachment for a comprehensive list of permitted uses under the title "CBD".

104 Kerr Street, Oakville
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