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

$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
$1,099,000
3 Beds ⋅ 2 Baths ⋅ W13771758 MLS
4 level side split on a quiet, kid-friendly crescent in west Oakville. 60X125 lot. Furnace and air conditioner replaced in 2023. Windows done in last 8 years. 3 bedrooms upstairs. Walkout from family room to covered back patio, nice place to bbq and entertain. Hardwood flooring on top 2 levels. Clever dog run setup. Lots of new development in the area. Quick access to highway and Bronte GO. Walk to rec centre. Quiet crescent in mature area in west Oakville.

557 Trafford Crescent, Oakville
$2,398,900
3 Beds ⋅ 4 Baths ⋅ W13767320 MLS
Welcome to 433 Allan Street, a distinctive residence designed for effortless living offering a perfect blend of timeless sophistication and low maintenance convenience set privately behind gates on a professionally landscaped tree lined lot. Newly renovated, spacious 9ft ceilings throughout and skylights create a bright inviting atmosphere including rich hardwood floors, custom millwork and built in cabinetry. The chef inspired kitchen features premium Bosch appliances, generous island and an inviting living room anchored by a striking fireplace. Wake up to the morning sunrise as the primary suite is a tranquil retreat with high ceilings, skylights, a spa-inspired ensuite including make up vanity, heated floors and a private outdoor living space overlooking the private grounds. A second bedroom, additional bathroom with heated floors and discreet stacked laundry alcove complete the main level with exceptional convenience. Entertain in style with a premium outdoor kitchen in a stunning alfresco setting with your own pizza oven and fire bowl. A finished lower level, featuring a third bedroom, full bathroom, kitchenette, laundry room, private courtyard and a separate walk up entrance offers flexibility for family and guests. Just steps outside, a detached garden suite with garage complete with bedroom, bathroom, kitchenette and private courtyard adds rare versatility for guests, extended family, a studio, home office, nanny suite or gym. A carport and ample parking for 10+ vehicles further enhance the property. Additional features include new windows 2023, hot tub and artificial turf. Offering just over 1375 square feet of living space with an additional 374 square feet in the garden suite. The best of downtown Oakville's lifestyle living is just steps away from waterfront, marina, parks, boutiques,restaurants,GO Station,Whole Foods,major highways and sought after schools. A rare opportunity to own a turn key property offering privacy and character in SE Oakville.

433 Allan Street, Oakville
$2,300,000
4 Beds ⋅ 3 Baths ⋅ W13765540 MLS
This rare find in the heart of Old Oakville is a bungalow duplex backing onto scenic 16 Mile Creek, beautifully renovated in 2021 and designed by Kate Zeidler (KZID). Steps from Downtown Oakville, Lake Ontario and the Oakville GO Station, this unique property offers 2 distinct 2-bedroom units - each featuring a separate garage, driveway, private decks with glass railings and breathtaking views. Unit 1 highlights hardwood floors, a gas fireplace in the family room, open-concept living and dining room, kitchen with heated floor, quartz counters & stainless steel appliances, heated floors in the 4pc bath, sunroom and private stairs leading down to the creek dock. Unit 2 offers an open-concept living area with gas fireplace, modern kitchen with breakfast bar, a primary suite with walk-in closet/office space, a 4pc bath with heated floors and ensuite laundry. Both units have independent furnace, A/C and utilities. This legal non-conforming duplex offers strong income potential for dual rental income (currently renting Unit 2 @ $4000/month), multi-generational families or live in one unit while leasing the other. Turnkey waterfront property in a premium location!

372 Trafalgar Road, Oakville
$1,349,000
3 Beds ⋅ 2 Baths ⋅ W13763380 MLS
ATTENTION BUILDERS AND INVESTORS. One of the Largest Mature Lots with 14025.36 Sq.ft Lot Area in Desirable College Park. Surrounded by Several Multi Million Dollar Homes in One of Oakville's Fastest Transforming Luxury Communities. ATTENTION EMPTY NESTERS AND DOWNSIZERS. Beautiful Open Concept Sun Drenched Bungalow on Mature Quiet Street. Turn Key and Move In Ready with Pride of Ownership Throughout. Truly An Entertainer's Paradise On This Private Muskoka Like Setting. Live In and ENJOY, Extend Or Renovate. Detached 38 x 22 Heated Garage and Mezzaine Storage, Garage Door 16 x 9. Exterior Stone and Cedar. Attached 17 x 5 Rear Outside Storage. Poured Concrete Side Pad 42 x 24 With Remote Double Gate Entry. Detached 16 x 11 Shed With Exterior Stone & Cedar makes Ideal Pool House. Features Include Natural Stone Patios, Extensive Decking, HotTub, Mature Trees, Fenced Yard, Lush Perennial Gardens, Lawn Sprinkler System with Micro Irrigation for Gardens, Small Pond with Fountain and Waterfall, Professional 5 Hole Golf Green. The House, Detached Garage and Shed Feature Steel Roofing, Leaf Guard Eaves and Pot Lighting. Walking Distance To Top Rated Schools, Parks, Nature Trails and Transit. Conveniently Close to Sheridan College, Go Station, Oakville Trafalgar Memorial Hospital, Sixteen Mile Sports Centre, Golf Courses, Shopping and Major Commuter Routes. PRIME LOCATION to LIVE, INVEST or BUILD DREAM HOME in a SOUGHT-AFTER MATURE FAMILY NEIGHBOURHOOD.

167 Oliver Place, Oakville
$469,000
2 Beds ⋅ 1 Baths ⋅ W13759866 MLS ⋅ Arbour Glen BLDG.
Bright, spacious, and full of personality, this stylish condo stands out with a smart, functional layout and an airy feel that's hard to find in the area. Thoughtfully designed for comfortable everyday living and easy entertaining, the open-concept space flows seamlessly from the modern kitchen to the generous living area and private balcony, in one of the town's most vibrant neighbourhoods. Surrounded by great dining, shopping, parks, transit, and everyday conveniences, this is an incredible opportunity for first-time buyers, downsizers or investors looking for value, lifestyle, and location. Don't miss your chance to get into one of Oakville's most dynamic communities. Includes 1 parking spot and 1 locker. Maintenance fees include heat, hydro, and water. Please note no dogs, no smoking building. Showing Note:

212 Kerr Street Unit 404, Oakville
$1,839,000
3 Beds ⋅ 2 Baths ⋅ W13758646 MLS
Calm, sun-filled, architectural & impeccably maintained, this exceptional Coronation Park home offers the perfect blend of timeless design & modern comfort on a beautiful, premium lot (79 x 157 x 97 x 134' irregular). Extensively renovated and thoughtfully updated, the home showcases outstanding craftsmanship & attention to detail throughout. At the heart of the home is a stunning light-filled kitchen featuring stainless steel appliances, granite counters, subway tile backsplash, under-cabinet lighting, pot lights & island with seating for 3. A cozy breakfast area overlooks the beautifully treed backyard & offers a walkout to the spacious composite deck with glass railings - perfect for entertaining or relaxing. The front foyer impresses with a custom front door and stylish slate-inspired flooring. The sun-drenched family room features a custom fireplace, B/I shelving, heated flooring and dramatic floor-to-ceiling windows with double-door access to the terrace. The dining room is highlighted by contemporary windows & architectural angles, while the living room offers a custom gas fireplace & large W/I bay window. Upstairs, 3 generous sized bedrooms are complemented by a beautifully renovated spa-inspired bathroom with a freestanding tub, oversized glass shower, marble feature wall, shaker-style cabinetry, Cambria countertops & 24" ceramic tile flooring. The partially finished lower level includes a recreation room with wood-burning fireplace & rough-in for a future full bathroom. Additional highlights include hardwood flooring, crown molding, updated windows, furnace (2026), roof (2012/2015), A/C (2022), siding (2012/2015), garage with updated door & flooring (2015), covered front porch with V-groove ceiling & pot lights, full irrigation system (2022) and more! South-facing lot that widens to 97' across the back, surrounded by mature trees, perennial gardens, tumbled stone terrace & walkways. Quiet, established neighbourhood, steps to Coronation Park and the lake!

1528 Warland Road, Oakville
$1,719,000
5 Beds ⋅ 2 Baths ⋅ W13752704 MLS
Welcome to highly sought-after Southwest Oakville, one of the area's most desirable neighbourhoods. Ideally situated within walking distance to the lake, Coronation Park, and scenic Josef Petriska Forest, and just minutes from top-ranked schools, this beautifully maintained home offers an exceptional combination of location, comfort, and lifestyle. Set on the south side of the street on a rare premium 75 x 150 ft. lot, this charming solid bungalow provides an abundance of space, privacy, and potential. The bright and inviting main level features 3 bedrooms and 2 bathrooms, along with an open-concept living, dining, and kitchen area designed for both everyday living and entertaining. The kitchen is complemented by a generous granite island, while hardwood and ceramic flooring flow throughout the home. Heated ceramic floors in the kitchen and main-floor bathroom add an extra touch of comfort, while elegant custom coffered ceilings enhance the warmth and character of the space. The spacious recreation room features a cozy gas fireplace, creating an inviting retreat for relaxing evenings. The lower level also offers two additional rooms that provide excellent flexibility and can be used as guest rooms, home offices, or additional living space to suit your needs. A walkout from the living area leads to a large deck and gazebo, offering the perfect setting for morning coffee, summer gatherings, or simply enjoying the peaceful and private backyard.

1422 Rebecca Street, Oakville
$1,618,000
4 Beds ⋅ 3 Baths ⋅ W13748338 MLS
Rarely Offered Backsplit On One Of The Most Prestigious Streets In Southeast Oakville's Eastlake! Set On A Stunning Ravine Lot Backing Onto Joshua's Valley Creek, This Beautifully Renovated 3+1 Bedroom, 3 Bathroom Home Combines Timeless Character With Thoughtful Modern Upgrades - Move In & Enjoy; Vacant & Ready For Quick Closing! | Approx. 1,324 Sq Ft Above Grade | RECENT UPGRADES: Newer Furnace (2023), Fresher Full-House Painting (2023) & Renovated 2nd Floor Bathroom (2023) | Main Floor Features Engineered Hardwood Flooring, Smooth Ceilings With Pot Lighting, A Custom Kitchen With Soft-Close Cabinetry, Pantry, Under-Cabinet Lighting, Glass Mosaic Backsplash, Quartzite Countertops & Breakfast Bar, Skylight, And Stainless Steel Appliances, Plus A Charming Bay Window In The Living Room | Renovated Main Bathroom With Heated Floor (As-Is) | Fully Finished Basement In-law Suite With Separate Walk-Out Entrance - Complete With Its Own Kitchen, Bedroom & 4-Piece Bathroom, Offering Excellent Income Potential Or Multi-Generational Living Space | Walk-Out From The Grade-Level Family Room To A Private Patio, Hot Tub (As-Is) & Tranquil Ravine Garden - A Rare Backyard Oasis In The Heart Of Oakville | Located In The Sought-After Maple Grove & Oakville Trafalgar High School Catchment, Steps To Famous Maple Grove St, Walking Distance To The Lake, Parks, Tennis Courts & Ice Arena | Minutes To Historic Downtown Oakville, Shopping, And Just 8 Minutes To Clarkson GO Station With Easy Access To QEW, 403, 407 & Pearson Airport | A Truly Move-In Ready Home Offering The Perfect Blend Of Nature, Convenience & Income Potential - Don't Miss This Rare Opportunity!

2283 Devon Road, Oakville
Start Your Search