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

2144 Rebecca Street, Oakville
$1,449,000
4 Beds ⋅ 3 Baths ⋅ W14120944 MLS
Welcome to 2144 Rebecca Street, a stunning, newly renovated and never-lived-in 4-bedroom, 3-bathroom backsplit nestled on an impressive 75 x120 ft lot in the highly sought-after Bronte community. Step through the elegant double-door entry with decorative frosted glass inserts into a bright and beautifully designed open-concept interior featuring pot lights throughout and no carpet. The inviting living room is filled with natural light from a large picture window overlooking the front yard. At the heart of the home is a stylish, modern kitchen showcasing stainless steel appliances, a centre island, abundant cabinetry and excellent storage, perfect for both everyday living and entertaining. Generously sized bedrooms provide plenty of space and comfort, complemented by two beautifully updated 3-piece bathrooms, while the spacious primary bedroom enjoys its own private 3-piece ensuite. The beautifully finished basement adds valuable living space with a large recreation room, wood flooring and a convenient laundry area with washer and dryer. Set on a rare oversized lot, this freshly renovated, move-in-ready home offers the perfect combination of modern style, comfortable living and an exceptional Bronte location.**Some pictures are virtually staged**

2144 Rebecca Street, Oakville
362 Winston Road, Oakville
$1,799,900
3 Beds ⋅ 4 Baths ⋅ W14117948 MLS
Welcome to 362 Winston Road, a sophisticated South Oakville residence situated on a coveted street surrounded by custom multimillion-dollar homes, and walking distance from Appleby College. This deceptively large, renovated bungalow features an amazing, multi-level rear addition that dramatically expands its square footage and provides distinct, functional living zones. The heart of the addition is a spacious ground-floor family room with a gas fireplace, large windows, and a direct walk-out to a private, west-facing backyard. Positioned on its own dedicated upper level, the expansive primary bedroom retreat serves as a private sanctuary complete with a sitting area, skylight, generous closet space, and a 5-piece ensuite. The original main level accommodates daily living with hardwood floors, solid wood California shutters, an updated skylit kitchen, a breakfast nook, a formal dining room, two additional bedrooms, and a 4-piece bathroom. The home's footprint extends into a fully finished lower level, significantly increasing functional space with a large recreation room, home office, gym, laundry area, full 3-piece bathroom, and extensive storage. With four full bathrooms distributed throughout, the layout effortlessly accommodates families and guests. Externally, the property features a rare, oversized attached four-car garage and mature landscaping. This property offers a rare blend of space, privacy, and location in one of South Oakville's premier enclaves.

362 Winston Road, Oakville
240 Colchester Drive, Oakville
$3,130,000
6 Beds ⋅ 4 Baths ⋅ W14116714 MLS
Set on a remarkable estate-sized lot in coveted Morrison, this traditional family home offers an exceptional opportunity in one of SE Oakville's most established + sought-after neighbourhoods. Surrounded by towering mature trees + an enclave of beautiful homes, the setting offers privacy, character + permanence. Walk to elementary + secondary schools, Lake Ontario, Gairloch Gardens, waterfront trails + parks, while enjoying the rare scale of a 100'x150' lot. The immaculate grounds + private rear yard create a wonderful setting for family life through every season. With 5+1 beds, 3.5 baths + triple car garage, it's poised to welcome a large family. Expansive principal spaces create a sense of scale across the main level. Beautifully appointed kitchen offers abundant cabinetry, ample workspace + picturesque views of the yard, w/a separate breakfast area connecting easily to the living + dining rooms. Tucked away, the main floor laundry + mudroom add everyday convenience. Bright solarium-style family room w/fireplace provides a warm space to gather, surrounded by generous glazing. Upstairs, five bright bedrooms offer generous proportions + natural light. Refined main bath serves the family bedroom wing, while the expansive primary suite features a very large ensuite + comfortable retreat-like proportions. LL is designed for family life w/a spacious recreation room, wet bar, gym area, 6th bed + full bath. There is room for movie nights, guests, older children + everything in between. Masterfully landscaped + incredibly private, the rear yard is anchored by a linear pool, stone lounges + layered gardens. A cedar-thatched gazebo w/fireplace creates a cozy gathering spot, while the stone patio is ideal for al-fresco dining. Flat grassy areas provide plenty of space for summer games + even a winter rink. Cherished neighbourhood known for its natural beauty, community + enduring appeal, Morrison offers an exceptional place to set down roots + truly enjoy the neighbourhood.

240 Colchester Drive, Oakville
105 WHITTINGTON Place, Oakville
$2,850,000
4 Beds ⋅ 6 Baths ⋅ W14113358 MLS
Straight from the pages of a design magazine, this beautifully renovated, on-trend home offers more than 4,500 sq. ft. of thoughtfully designed living space. Tucked away on a quiet cul-de-sac in prestigious Southwest Oakville, it's just steps from Appleby College and the shores of Lake Ontario. The property is professionally landscaped by award-winning Gildermans, creating a stunning setting that perfectly complements this exceptional home. Designed for both everyday living and effortless entertaining, the main floor features a spacious formal dining room and a warm, inviting family room with a wood-burning fireplace. The stunning chef's kitchen is a true showpiece, featuring a Wolf induction cooktop, two double wall ovens, Sub-Zero refrigerator, two Miele dishwashers, two Marvel wine and beverage refrigerators, quartz countertops, and an impressive 9-foot island. The kitchen flows seamlessly into the family room, creating the perfect setting for gathering with family and friends. Upstairs, the luxurious primary suite serves as a private retreat, complete with a spa-inspired five-piece ensuite, walk-in closet, and an expansive terrace-ideal for enjoying your morning coffee or unwinding in the evening sun. This level also includes a generously sized second bedroom with its own ensuite, two additional bedrooms, a home office, a full bathroom, and a brand-new full laundry room for ultimate convenience. The finished lower level offers exceptional additional living space with a large recreation room, a second laundry room featuring a Miele washer and dryer, and a three-piece bathroom. Step outside to your own private backyard oasis, where a sparkling saltwater pool and beautifully landscaped gardens create the perfect escape. This exceptional home combines luxury, comfort, thoughtful design, and an unbeatable location-an opportunity not to be missed.

105 WHITTINGTON Place, Oakville
1517 Elm Road Unit 9, Oakville
$650,000
3 Beds ⋅ 2 Baths ⋅ W14112720 MLS
Welcome to this charming 3-bedroom, 2-bathroom, two-storey brick condo townhouse, nestled in an established Oakville community surrounded by mature trees, landscaped green space and pedestrian walkways. A private covered entrance leads into a bright and welcoming foyer. The functional kitchen features crisp white cabinetry, generous counter space, subway tile backsplash, stainless steel appliances and large windows that fill the space with natural light and offer views of the greenery. The spacious dining area flows into the adjoining living room, both featuring beautiful hardwood flooring and a comfortable layout ideal for everyday living and entertaining. The bright living room offers large windows, sliding glass doors overlooking the outdoor space and a freestanding fireplace adding warmth and character. Upstairs, the spacious primary bedroom features hardwood flooring, multiple windows, ample closet space and room for a dedicated home office or work-from-home area. Two additional bright bedrooms provide excellent flexibility for family, guests or office space, complemented by a well-maintained main bathroom with a tub/shower combination and generous vanity. The finished lower level offers versatile living space with a spacious recreation area, perfect for a family room, games area or home office. This level also features a finished bathroom with glass-enclosed shower, convenient laundry area, utility sink and additional storage. Step outside to enjoy the fully fenced private backyard with an interlocking patio and mature greenery, creating a peaceful setting for outdoor dining, relaxing or entertaining. Convenient covered parking is located just steps from the home. Ideally situated in a family-friendly Oakville neighbourhood close to parks, green space, everyday amenities and nearby schools, including Munn's Public School and White Oaks Secondary School, this welcoming home offers an excellent combination of comfort, functionality, privacy and community living.

1517 Elm Road Unit 9, Oakville
341 Lynnwood Drive, Oakville
$1,199,900
3 Beds ⋅ 2 Baths ⋅ W14111866 MLS
Welcome to 341 Lynnwood Drive, a beautifully updated 3-bedroom, 2-bathroom sidesplit situated on a generous corner lot in Oakville's highly desirable Falgarwood neighbourhood. Surrounded by mature trees & well-maintained gardens, this inviting home offers a wonderful blend of modern updates, comfortable living spaces, and a private outdoor retreat. Step inside to discover a bright interior featuring new engineered wide plank hardwood flooring for the main & upper levels, including the staircase, banister, & spindles (2024), elegant wood California shutters, and updated smooth ceilings with pot lights (2025). Spacious living room is filled with natural light from a large bay window, and the dining room offers a walkout to the deck, perfect for indoor-outdoor entertaining. Renovated kitchen (2025) features quartz countertops, a stylish backsplash, pantry, and a convenient walkout to the backyard. All three bedrooms are located on the upper level, including the primary bedroom with custom built-ins (2025). Both bathrooms have been tastefully renovated with updated showers & vanities (2021). Fully finished lower level offers additional living space with an above-grade window, a generous laundry room, and abundant crawl-space storage. Outside, enjoy a lush, private, fully fenced backyard with mature gardens, trees, updated deck, fence, & gates (2022). Attached double garage with new garage door (2017) and updated driveway (2017). Additional improvements include exterior painting of the eavestroughs, soffits & windows (2021), furnace & A/C (2018), owned hot water tank, sump pump (2021), and brand new roof (2026). Ideally located in the heart of Falgarwood, just a short walk to Sheridan College & close to excellent schools, parks, trails, shopping, recreation centres, the GO Train, QEW, & vibrant Downtown Oakville. A wonderful opportunity to enjoy a welcoming home in one of Oakville's most established & convenient neighbourhoods!

341 Lynnwood Drive, Oakville
383 Maplehurst Avenue, Oakville
$2,295,000
4 Beds ⋅ 3 Baths ⋅ W14111246 MLS
An exceptional opportunity to secure a substantial 75 272 ft lot (approximately 20,505 sq. ft.) in one of West Oakville's most established luxury residential neighbourhoods. Surrounded by distinguished custom-built homes on a quiet, tree-lined street, this remarkable property presents an outstanding opportunity to renovate, expand, or create a bespoke estate residence. Zoned RL2 SP:1, the property offers a compelling framework for custom-home development, with provisions permitting a detached dwelling of up to three storeys and 12 metres in height, subject to applicable zoning requirements and municipal approvals. The impressive lot dimensions provide flexibility for thoughtful architectural design, generous setbacks, and expansive outdoor living spaces, including the potential for a swimming pool, cabana, outdoor entertaining areas, and landscaped gardens. The property's setting is equally appealing. Maplehurst Avenue is characterized by mature trees, generous lots, custom residences, and a quiet streetscape without sidewalks. The existing bungalow provides immediate utility, including potential rental income, while buyers explore future redevelopment or renovation plans. Ideally situated near Lake Ontario, Appleby College, Downtown Oakville, Bronte Harbour, waterfront parks, and excellent public and private schools, the location offers an attractive balance of privacy, convenience, and lifestyle. Easy access to the QEW, Highway 403, and GO Transit further enhances connectivity throughout the Greater Toronto Area. Whether envisioned as a distinctive custom-built estate, a long-term investment, or a strategic acquisition for future redevelopment, 383 Maplehurst Avenue offers an exceptional combination of lot size, location, and potential in the heart of West Oakville.

383 Maplehurst Avenue, Oakville
316 Kerr Street, Oakville
$179,900
W14110472 MLS
Well established location for the best eat in or take out Pizza, local diner friendly bar. Bring your restaurant concept to Oakville's Kerr Village. This long-established restaurant and bar location features a full kitchen, dedicated lower-level prep space, a spacious bar and an inviting front patio. Surrounded by local shops and established residential neighbourhoods, with downtown Oakville, waterfront parks and community amenities nearby, the space offers an established setting for a new name, menu and atmosphere. Nearby municipal parking and convenient transit connections to Oakville GO add to the location's appeal. Located in Oakville's established Kerr Village neighbourhood, the restaurant is surrounded by a mix of residential communities, independent businesses, recreation facilities and cultural destinations.

316 Kerr Street, Oakville
1348 Fieldcrest Lane, Oakville
$1,629,000
5 Beds ⋅ 4 Baths ⋅ W14104942 MLS
Welcome to this spacious 4+1-bedroom, 4-bathroom detached family home, ideally situated in sought-after Glen Abbey and backing onto peaceful green space.A double-door entrance opens to an impressive foyer with a grand staircase and leads into featuring hardwood flooringoffers plenty of cabinetry, generous prep space and a spacious eat-in area, with direct access to a beautiful multi-tiered deck overlooking the private backyard oasis.The inviting family room is centred around a gas fireplace with a classic brick surround, creating a warm and comfortable space for everyday living. A convenient mudroom provides additional storage, a double-door closet and a separate side entrance.Upstairs, you'll find four generously sized bedrooms, including a spacious primary retreat complete with a walk-in closet and grand four-piece ensuite. Three additional well-proportioned bedrooms and a full main bathroom provide plenty of room for the entire family.The finished lower level adds even more versatile living space with a large recreation area, three-piece bathroom and an additional room perfect for a fifth bedroom, home office, gym or guest space.Outside, the multi-tiered deck and private backyard create a true retreat, made even more special by the tranquil green space beyond. Offering generous living space inside and out, this is a wonderful opportunity to enjoy a well-appointed family home in one of Oakville's most established and desirable communities.

1348 Fieldcrest Lane, Oakville
153 Oliver Place, Oakville
$1,099,998
5 Beds ⋅ 2 Baths ⋅ W14102370 MLS
Attention Builders and Investors! Rare opportunity in one of Oakville's fastest-transforming luxury neighbourhoods. Excellent value and great curb appeal 60 x 125 lot. 3 + 2 bedroom spacious bungalow with great floor plan on deep pool sized lot in beautiful, established College Park. Surrounded by multi million dollar homes. The double driveway can easily accommodate 6 vehicles. Convenient rear yard shed with power, rear deck and front yard veranda complete. Kitchen replaced (2015) Windows and doors replaced. Metal roof installed with 50 year pro-rated warranty (1994). Open concept bright living and dining room with massive front window. Hardwood throughout the main floor was refinished 2012. On the lower level you will find a large rec room with 2 extra rooms with closets, 3 piece bath and laundry area plus storage. College Park is a well established up and coming neighbourhood with easy access to major highways, public transit and walking distance to Sunningdale School. Seller offering VTB w/25% down.A few minutes drive Oakville Trafalgar Memorial Hospital, Glen Abbey Golf Club, Sheridan College, Go Station, Sixteen Mile Creek, Oakville Place Mall. Close to all Major Highways, A great location and still offers affordability for builders and first time home buyers alike.

153 Oliver Place, Oakville
269 Sunray Road, Oakville
$1,899,000
4 Beds ⋅ 4 Baths ⋅ W14102272 MLS
BEAUTIFULLY REIMAGINED FAMILY LIVING IN SOUGHT-AFTER BRONTE! PRIVATE BACKYARD OASIS WITH POOL! Discover an exceptional blend of thoughtful design, quality craftsmanship, and inviting outdoor living at 269 Sunray Road. Set on a quiet, family-friendly street in established Bronte, this four bedroom residence was extensively redesigned in 2015, including a substantial 600 square foot addition above the garage, creating an impressive primary retreat complete with an electric fireplace, walk-in closet, and spa-inspired four-piece ensuite. The open concept main level is perfectly suited to everyday family life and entertaining, featuring a bright, well-appointed kitchen with quartz countertops, stainless steel appliances, extensive cabinetry, and a large centre island that naturally brings everyone together. PurParket hardwood flooring, made in Canada, enhances the main level (2026) and upper level (2015), while custom cabinetry by Precision Cabinetry adds a refined finishing touch. Extensive upgrades include spray foam insulation throughout, updated electrical, hardwired smoke and carbon monoxide detectors, a 200-amp breaker panel, and a furnace and roof replaced in 2015. The backyard is a true highlight, offering a private outdoor escape with a 16' x 30' inground saltwater pool and hot tub, both installed in 2018, creating the perfect setting for summer gatherings, relaxed evenings, and memorable family moments. Enjoy the convenience of walking to Eastview Public School, neighbourhood parks, Queen Elizabeth Park Community and Cultural Centre, and South Oakville Centre (Hopedale Mall). Just minutes from the charm of Bronte Village and the waterfront, this is an outstanding opportunity to enjoy comfortable, beautifully updated family living in one of South Oakville's most welcoming neighbourhoods. (certain images have been digitally enhanced)

269 Sunray Road, Oakville
18 Osborne Crescent, Oakville
$999,000
3 Beds ⋅ 2 Baths ⋅ W14098920 MLS
Lovingly maintained one-owner 4-level split in Oakville's sought-after College Park community on an extra-deep lot, ideally located within walking distance of White Oaks, Montclair, Munn's and Sunningdale Public Schools; Oakdale, Oxford and Sunningdale Parks, Oakville Golf Club and scenic Sixteen Mile Creek trails. Just minutes to Sheridan College, Glen Abbey Golf Club, Oakville Place, Oakville GO Station, the QEW and everyday amenities, offering exceptional convenience for families and commuters alike. The oversized backyard features mature trees and shrubs, a large garden shed, slab-stone patio and ample space for a future pool, while the extra-long driveway, attached garage, roof shingles (2024) and newer windows enhance curb appeal and peace of mind. The functional multi-level layout includes a welcoming foyer with a convenient 2-piece bathroom and backyard access, a bright living room with an oversized window, formal dining room, and an eat-in kitchen with abundant white cabinetry, tiled walls, California shutters and three appliances. Upstairs offers three spacious bedrooms and a 4-piece bathroom with a soaker tub/shower combination, while the lower-level recreation room provides the perfect space for family gatherings, a media room, children's play area or home office. An outstanding opportunity to own a well-cared-for family home in one of Oakville's most established, family-friendly neighbourhoods.

18 Osborne Crescent, Oakville
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