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. Known for its stunning waterfront, vibrant cultural scene, and family-friendly atmosphere, Oakville is a place where community spirit thrives. With its charming downtown area filled with boutique shops, cozy cafes, and art galleries, Oakville offers a perfect blend of small-town charm and modern conveniences.

For those seeking a home in this delightful city, consider exploring properties that fall within the age range of 51 to 99 years. These homes often exude character and history, showcasing architectural styles that reflect the evolution of the area over the decades. Many of these residences feature unique design elements, spacious layouts, and mature landscaping that create a warm, inviting atmosphere.

Living in an older home in Oakville means embracing a strong sense of community, as these neighborhoods are often well-established, with friendly neighbors and a rich tapestry of local stories. You’ll find yourself just a stone's throw away from beautiful parks, top-rated schools, and excellent recreational facilities, making it an ideal place for families and professionals alike.

Whether you’re drawn to the charm of a classic Victorian or the elegance of a mid-century bungalow, homes in Oakville with a history of 51 to 99 years offer a unique opportunity to immerse yourself in a vibrant community while enjoying the comforts of modern living. Discover your dream home in Oakville today, and experience the perfect blend of history and contemporary lifestyle in this enchanting lakeside town!

Newest Oakville Homes with 51-99 Approx Age

503 Valley Drive, Oakville
$1,788,800
5 Beds ⋅ 2 Baths ⋅ W14157878 MLS
Wow! Meticulously cared for and beautifully updated, this impressive 3+2 bedroom home in Bronte West offers refined finishes and inviting spaces for everyday living and entertaining. A custom kitchen anchors the home, while thoughtful details throughout-including a walk-through primary closet-bring style, comfort and function together. The welcoming lower level extends the living space with two generously sized bedrooms and an oversized recreation room featuring a gas fireplace. Whether you're hosting family, enjoying a movie night or accommodating overnight guests, there's room to settle in and feel at home. Outside, the backyard's peaceful creek side setting and spacious vaulted gazebo offer a little Muskoka in the city. Garage is fully insulated. Property has irrigation. Enjoy quiet mornings, summer dinners and relaxed evenings surrounded by nature. Set on a quiet street with a generous lot, this property offers a beautiful home to enjoy today and space to explore your vision for the future. Move in and savour the setting, or consider the possibilities for your forever home, subject to applicable approvals. A special Bronte West property you won't want to miss!

503 Valley Drive, Oakville
2490 Yarmouth Crescent, Oakville
$945,000
4 Beds ⋅ 2 Baths ⋅ W14154474 MLS
AN EXCITING OPPORTUNITY IN WEST OAKVILLE! Discover the incredible potential of this solid brick bungalow, situated on a generous 60' x 100'+ lot in one of Oakville's established neighbourhoods. Perfect for first-time buyers, renovators, investors, or those looking to create their dream home, this property offers an excellent opportunity to transform, personalize, and add value. Offering approximately 1,312 sq. ft. above grade plus a finished lower level, this 3+1 bedroom, 2-bathroom home features a functional layout with plenty of possibilities. The separate basement walk-up provides added flexibility for extended family, guests, or future living arrangements. An attached double garage and driveway offer parking for up to six vehicles, while the spacious lot provides excellent potential for outdoor living, landscaping, or future improvements. Important updates have already been completed, including a new roof (2025), furnace (2018), and central air conditioning (2018), providing a solid starting point for your renovation plans. The interior is ready for a refresh, offering a blank canvas to bring your vision to life and create a home that truly reflects your style. LOCATION, LOCATION, LOCATION! Nestled in desirable West Oakville, this property is conveniently located near Gladys Speers Public School, St. Dominic Catholic Elementary School, T.A. Blakelock High School, parks, trails, and the Queen Elizabeth Park Community & Cultural Centre. Just minutes from Lake Ontario, Bronte Village, and Bronte Harbour, enjoy waterfront trails, charming cafés, restaurants, boutique shopping, and marina views. Commuters will appreciate easy access to Bronte GO, the QEW, and major routes throughout the GTA. With a generous lot, double garage, separate walk-up, and outstanding renovation potential, this is your chance to unlock the possibilities of West Oakville living. Bring your vision and make it your own! Offers welcome anytime!

2490 Yarmouth Crescent, Oakville
62 Burnhamthorpe Road W, Oakville
$2,790,000
5 Beds ⋅ 3 Baths ⋅ W14152324 MLS
This one-of-a-kind, beautifully updated split-level home sits on 0.75 acres, backs up to protected forest and offers versatile living space, exceptional privacy, and outstanding potential for multi-generational living, investment, or future development. Enjoy the ultimate country-in-the-city lifestyle in this dream home, with a 3-car garage and a massive new (2025) driveway for 20 cars! A foyer leads to a large formal dining room, a renovated (2024) powder room, an office and a walkout door to a deck. Inside, this generous upper-level home features 4 oversized bedrooms with walk-in closets, wide-plank engineered floors, 2 fully renovated washrooms, and a new laundry room with custom cabinetry for easy tasks. The primary suite boasts a luxury ensuite with a free-standing tub and shower, plus a walk-out to a balcony backyard and the swimming pool.overlooking a private The elevated main level features a family/living room and a light-filled, large kitchen with new stainless steel appliances and a walk-out to a three-tier deck. The lower level features a recreation room with a wood stove and an additional fully renovated 5th bedroom with plenty of storage, an exercise room, and a utility room. Thousands have been spent on recent updates, including pot lights throughout the house, a hot water tank, updated plaster/ stucco, new concrete walkways, and a new stone front With excellent access to Hwy 401, 403, 407, and QEW, the property offers endless possibilities for someone looking for a new familyporch. home within walking distance of a new school and the daycare, or a builder/developer seeking redevelopment opportunities.

62 Burnhamthorpe Road W, Oakville
286 Watson Avenue, Oakville
$2,950,000
3 Beds ⋅ 4 Baths ⋅ W14152080 MLS
Some streets are more than an address. Watson Avenue is one of Old Oakville's most admired, cherished for its mature tree canopy, beautiful homes, renowned schools and exceptional walkability to Downtown Oakville. Welcome to 286 Watson Avenue, a charming, move-in-ready home thoughtfully updated by its current owners. Recent improvements inside and out include freshly painted wood siding, custom Inline Fibreglass windows and front door, and refreshed landscaping that creates a warm welcome from the moment you arrive. Inside offers over 2300sqft of living space, with vintage Oak hardwood floors and generously proportioned principal rooms bringing warmth and character throughout. The main floor offers both formal living and dining rooms, alongside a bright white kitchen appointed with Wolf and Sub-Zero appliances. A cozy breakfast nook and wood-burning fireplace make it a natural gathering place, while expansive windows frame views of the backyard and gardens. Upstairs, three well-sized bedrooms feature generous closets, newer hardwood flooring, updated trim and fresh paint. Two renovated bathrooms complete the level. The finished walk-out basement adds valuable flexibility, with a spacious recreation room, room for a home office or gym, a full bathroom and a renovated laundry room with additional storage. The west-facing backyard is a private, sun-drenched retreat, framed by mature trees and beautifully established gardens. Spend summer afternoons by the heated 16' x 32' in ground pool, or gather with family and friends in the cabana. A special opportunity to enjoy a thoughtfully updated home, a wonderful outdoor setting and the distinctive lifestyle of one of Old Oakville's most coveted streets. See the attached list of improvements for additional details.

286 Watson Avenue, Oakville
255 Spring Garden Road, Oakville
$1,699,000
4 Beds ⋅ 3 Baths ⋅ W14152016 MLS
Welcome to this exceptional Southwest Oakville family home, where space, privacy, and an unbeatable location come together. Nestled on a quiet street and set on a premium 79 x 140-foot lot, this 4-bedroom residence offers approximately 2,300 sq. ft. of living space in one of Oakville's most sought-after neighbourhoods. Surrounded by mature trees, this home offers exceptional privacy while providing the convenience of being close to everything Oakville has to offer. The expansive backyard is a true private retreat, featuring a kidney-shaped in-ground pool and spacious patio-perfect for summer entertaining, family gatherings, or relaxing outdoors. The bright and functional main level is designed for everyday family living and entertaining. The well-equipped kitchen features abundant cabinetry, and a bright breakfast area with direct access to the backyard. The formal living and dining rooms offer excellent flow for hosting guests, while the inviting family room provides a cozy atmosphere with a fireplace and California shutters adding warmth and character. A convenient main floor laundry room and powder room complete the main level. Upstairs, you'll find four spacious bedrooms, including a generous primary suite with a walk-in closet and private 4-piece ensuite. The unfinished lower level offers endless possibilities to create additional living space tailored to your family's needs, whether it's a recreation room, home gym, office, or entertainment area. Located in a highly sought-after Southwest Oakville neighbourhood, this home is surrounded by top-rated schools, including the prestigious Appleby College, along with excellent public and Catholic school options. Enjoy easy access to Lake Ontario, Coronation Park, trails, shopping, restaurants, libraries, and the GO Station. A wonderful opportunity to move in and enjoy this well-loved home or bring your vision and create your dream property in one of Oakville's most established and coveted communities.

255 Spring Garden Road, Oakville
58 Onslow Court, Oakville
$899,900
3 Beds ⋅ 2 Baths ⋅ W14144558 MLS
Welcome to 58 Onslow! A beautifully refreshed three bedroom, two full bath townhouse in a desirable Oakville court location, offering one of the largest yards in the neighbourhood. With no additional monthly fees, an excellent school catchment and a fantastic family-friendly setting, this home checks all the boxes.Inside, enjoy a newly renovated kitchen and bathroom, updated flooring and fresh paint, while the refreshed exterior adds to its welcoming curb appeal. The major updates have been taken care of, leaving the perfect opportunity for a new family to add their own personal touches and make it truly theirs. Whether it's family dinners in the kitchen, summer evenings in the backyard or making memories for years to come, 58 Onslow is ready for its next chapter. All that's missing is the family to make it home! RSA

58 Onslow Court, Oakville
2035 Hixon Street, Oakville
$1,599,900
3 Beds ⋅ 3 Baths ⋅ W14144432 MLS
Set on a sought-after Bronte street surrounded by custom-built homes, this bungalow offers a bright open-concept main floor with hardwood and tile throughout. The kitchen features granite countertops, built-in appliances and a large centre island, perfect for everyday living and entertaining. A walk-out to the deck provides seamless indoor-outdoor living. The dining area flows into the living room, where you can cozy up by the gas fireplace next to a large picture window that fills the space with sunlight. Two well-sized bedrooms and a 4-piece bath complete the main level.The finished lower level has a separate walk-out to the backyard. It includes a private primary suite with a walk-in closet and ensuite, set apart from the main-floor bedrooms. Custom built-in cabinetry creates a work-from-home space, and the spacious family room is a great place to relax or entertain. A powder room and laundry room round out this level.Outside, the spacious backyard is ideal for entertaining, gardening or play. The detached 1.5-car garage adds room for parking, storage or a workshop.Walk to the shops, restaurants, harbour and waterfront trails of Bronte Village, and to Coronation Park on Lake Ontario. This home suits downsizers and young families looking to settle in one of Oakville's most desirable lakeside communities. It's also a great opportunity for anyone planning a future custom build, with a comfortable home to live in while you design your dream home.

2035 Hixon Street, Oakville
1100 INVICTA Drive Unit 23, Oakville
$18
2 Baths ⋅ W14140286 MLS
THIS 2000 S.F. INDUSTRIAL UNIT, HAS APPROXIMATELY 250 S.F. OF BEAUTIFULLY FINISHED FRONT OFFICE SPACE, 2 WASHROOMS, A SMALL KITCHENETTE AND EXCELLENT DOCK LEVEL LOADING AT THE REAR.

1100 INVICTA Drive Unit 23, Oakville
89 Holyrood Avenue, Oakville
$1,999,900
4 Beds ⋅ 4 Baths ⋅ W14127802 MLS
Rare Lakeshore Opportunity in Prestigious Oakville. A rare opportunity to own a beautiful home tucked away on a prestigious private cul-de-sac just off Lakeshore, near the water's edge. Set on a premium 60' x 144' fenced lot, this property offers an exceptional blend of privacy, space and location.Inside, the open-concept layout is filled with natural light and features warm hardwood flooring, high-end appliances and inviting living spaces designed for both everyday living and entertaining.Step outside to your own private retreat, where mature trees create a lush, peaceful backdrop and the generous backyard feels more like a Muskoka escape than a home in Oakville. Relax in the hot tub, entertain family and friends, or simply enjoy the tranquility and privacy of this exceptional setting.A truly special property in a sought-after Lakeshore location - where everyday living feels like a vacation.

89 Holyrood Avenue, Oakville
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
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