1013 - OO Old Oakville Homes with 31-50 Approx Age

1013 - OO Old Oakville Homes with 31-50 Approx Age

Welcome to the enchanting neighborhood of 1013 - OO Old Oakville, a hidden gem nestled in the heart of Oakville, Ontario. This charming area perfectly blends historical charm with modern conveniences, making it a sought-after destination for families, professionals, and retirees alike.

Old Oakville is renowned for its picturesque streets lined with mature trees, beautiful gardens, and a delightful mix of architectural styles that reflect its rich history. Homes in this neighborhood, typically aged between 31 to 50 years, offer a unique character that newer developments simply can’t match. From cozy bungalows to spacious two-storey homes, each property tells a story, showcasing the craftsmanship and design of its era while often featuring modern updates that cater to today’s lifestyle.

Beyond the stunning homes, residents of Old Oakville enjoy a vibrant community atmosphere. The neighborhood is just a stone’s throw away from the picturesque shores of Lake Ontario, where you can indulge in outdoor activities such as hiking, biking, and leisurely strolls along the waterfront. The local parks, like the serene Bronte Creek and the expansive Coronation Park, provide ample green space for family gatherings and weekend picnics.

Old Oakville is also conveniently located near an array of amenities, including boutique shops, delightful cafes, and top-rated schools. The community is well-connected, with easy access to major highways and public transit, making commutes to Toronto and beyond a breeze.

Experience the charm and warmth of 1013 - OO Old Oakville, where history meets community, and every home has a story waiting to be told. Your dream home awaits in this inviting neighborhood!

Newest 1013 - OO Old Oakville Homes with 31-50 Approx Age

$4,999,000
4 Beds ⋅ 5 Baths ⋅ W13524820 MLS
Grand Grounds. Timeless Elegance. Extraordinary Potential.An exceptional opportunity in one of Olde Oakville's most prestigious neighbourhoods. Tucked behind private gates and nestled beneath a magnificent canopy of mature trees, this beautifully landscaped and increasingly rare 0.82-acre estate offers over 7,100 square feet of living space in an irreplaceable setting just moments from Downtown Oakville.Approached by a sweeping circular drive, the timeless brick residence immediately impresses with its classic Colonial Williamsburg-inspired architecture, elegant symmetry, and commanding presence. Beyond the front entrance, peaceful views of the private pond and lush landscape create a tranquil, park-like retreat rarely found in such a coveted urban location.Custom built in 1980, this stately four-bedroom residence offers an extraordinary opportunity to reimagine an exceptional property. Offered in "as is" condition, the home presents the perfect canvas for those looking to undertake a significant renovation, thoughtfully restore its timeless character, or explore the opportunity to create a magnificent custom estate (subject to all necessary approvals). Whether preserving its enduring architectural charm or designing an entirely new vision, the possibilities are truly exceptional.The expansive grounds provide an incredible backdrop for family living, entertaining, and creating lasting memories for generations to come. Properties offering this rare combination of land, privacy, scale, and location are becoming increasingly difficult to find.Ideally situated within one of Oakville's most sought-after school districts and just a short walk to Downtown Oakville, the Oakville GO Station, public and private schools, Post Park, Whole Foods, Longo's, boutique shopping, restaurants, and the lakefront, this is more than an exceptional property-it is a rare opportunity to create a legacy estate in one of Olde Oakville's most coveted locations.

488 Macdonald Road, Oakville
$2,988,000
3 Beds ⋅ 3 Baths ⋅ W13514262 MLS
Fully renovated luxury home just steps from the boutiques, restaurants, waterfront,and lifestyle amenities of Downtown Oakville. Designed for effortless living, this exceptional residence offers the perfect blend of modern sophistication and low-maintenance convenience.Inside, Cathedral ceilings, premium walnut finishes, engineered hardwood flooring,and skylights create a bright, elegant atmosphere. The chef-inspired kitchen features a high-end Bertazzoni stove and stainless steel appliances, ideal for both everyday living and entertaining. Additional highlights include heated floors, gas fireplaces,a private office, a built-in sound system, and a spa-inspired ensuite.Outside, enjoy beautifully designed maintenance-free grounds, offering year-round enjoyment without the upkeep. A rare opportunity to own a turnkey luxury property in one of Oakville's most sought-after walkable neighbourhoods.

160 Allan Street, Oakville
$3,590,000
6 Beds ⋅ 7 Baths ⋅ W13507594 MLS
This impressive 5,500+ sq. ft. two-and-a-half-storey residence is set back from one of Southeast Oakville's most prestigious streets on an extraordinary 29,000 sq. ft. private, park-like lot backing onto a picturesque creek. Offering over 7,000 sq. ft. of finished living space, with 5+1 bedrooms and 7 bathrooms, this home provides exceptional space, privacy and flexibility for family living and entertainment. The main floor features a beautifully renovated open-concept kitchen (2020) overlooking the living, family and dining areas with W/O to a large deck and spectacular gardens. Additional highlights include a formal dining room, elegant sitting room with a gas fireplace, soaring ceilings, oversized arched windows, a private office, mudroom and powder room.The second level offers three spacious bedrooms, including two with private 2-piece ensuites and backyard views. The third bedroom features a sitting area, double closets and an ensuite with integrated laundry. An office/playroom, walk-in closet and an additional 4-piece bathroom complete this level. The top floor offers two oversized bedrooms connected by a shared 5-piece bathroom.The finished basement includes a spacious recreation area, an additional bedroom, a 3-piece bathroom and two versatile bonus rooms ideal for a home office, gym, hobby space or storage.The private grounds feature mature trees, lush gardens, direct access to a picturesque creek, approximately 9,500 sq. ft. of additional open space for gardens or outdoor entertaining, and a hard-court area perfect for basketball, pickleball or family activities. This exceptional property is within the highly sought-after catchment for Oakville Trafalgar HS, Maple Grove PS and E.J. James PS, and just minutes from St. Mildred's-Lightbourn School and Linbrook School. Walk to grocery stores, cafés, bakeries and restaurants. A rare opportunity to own a spacious family home on an exceptional lot.

480 CHARTWELL Road, Oakville
$3,980,000
4 Beds ⋅ 4 Baths ⋅ W13109474 MLS
Set on a beautiful 100' x 136' lot in Prestigious Olde Oakville, this exceptional family home offers 4,752 sq ft of total living space of refined timeless design & impeccable craftsmanship all just a short stroll to Downtown Oakville, the lake, and some of Oakville's most sought-after schools. classic brick exterior, solid wood front door, and towering mature trees create a warm and elegant first impression. This home exudes an inviting aesthetic that feels made for family living and effortless entertaining.The kitchen features top-of-the-line appliances, two Miele dishwashers, dual walk-in pantries, water filtration system, three sinks including a coffee station/wet bar, and an oversized island that comfortably gathers family and friends for everything from casual breakfasts to holiday celebrations. The adjoining dining room is anchored by a charming wood-burning fireplace, while the spacious family room, also with a wood-burning fireplace, opens seamlessly to the private backyard, creating an ideal indoor-outdoor connection. Enjoy sunny south exposure, a sparkling saltwater swimming pool(liner/pump/heater 2024), Maibec deck with sleek glass railings, and a beautiful stone patio ideal for summer dining and lounging. Despite the impressive outdoor amenities, there remains abundant green space for children to play and the whole family to gather. The functional mudroom and sophisticated main floor den complete the thoughtfully designed main level. The second floor is equally impressive, highlighted by a luxurious primary retreat with its own gas fireplace, walk-in closet, custom built-in storage, and five-piece ensuite with heated flooring. Three additional generously sized bedrooms and a beautifully appointed full bathroom provide ample space for a growing family. Finished to the highest standards, this extraordinary residence offers the rare combination of timeless style, family-focused functionality, and an unbeatable Olde Oakville location. Welcome Home.

528 Michael Terrace, Oakville
$734,900
2 Beds ⋅ 2 Baths ⋅ W13062840 MLS ⋅ The Ashbury BLDG.
Downtown Oakville at your doorstep! Impeccably maintained 2-bedroom, 2-bathroom condo combines comfort and convenience with a rare private balcony, all just moments from Oakville's renowned dining scene, boutique shopping, and picturesque waterfront trails. Offering 975 sq. ft. of thoughtfully designed living space, this unit features a functional split bedroom layout, two walk-in closets, upgraded light fixtures and a bright, carpet-free open-concept design. The kitchen is both stylish and functional, featuring matte black tile flooring, white cabinetry & countertops, and three full size appliances including a new dishwasher. The open-concept layout makes everyday living and entertaining effortless. Kitchen is ideally connected to the great room, plus large sunny sliding glass windows to the private balcony!The spacious primary bedroom includes a walk-in closet, a 4-piece ensuite with a glass-enclosed shower and direct access to your private balcony-perfect for morning coffee or evening relaxation. The second bedroom is equally generous, also featuring a walk-in closet. The main 4-piece bathroom offers tile flooring and a glass-enclosed shower. Insuite laundry room with additional storage & cabinets adds to the convenience. BRAND NEW furnace (to be installed this fall 2026)!Complete with 1 underground parking space and 1 locker, this home checks all the boxes. This well managed building is a boutique style low rise condominium that has been beautifully updated and features a party room, visitor parking and landscaped courtyard. Located in the heart of quaint Downtown Oakville, just steps to boutiques, bakeries, cafés, Oakville Centre for performing arts centre, renowned restaurants. Your Downtown Oakville lifestyle starts here!

185 Robinson Street Unit 202, Oakville
$799,900
2 Beds ⋅ 2 Baths ⋅ W13022402 MLS
Welcome to this beautifully updated 2-bedroom, 2-bath, with parking condo right on Oakville's renowned Town Square. With tasteful finishes and a timeless design, this residence offers elegant living in one of the most walkable and coveted locations in town. Enjoy sunset views from your covered terrace, steps from boutique shops, acclaimed dining, the lake, marina, and the Oakville Centre for the Performing Arts. The building itself has been fully refreshed inside, blending classic sophistication with modern comfort. Includes one parking space, with guest parking available. A rare opportunity to live in the heart of Old Oakville without the million-dollar price tag.

185 Robinson Street Unit 315, Oakville
$3,600,000
W12773688 MLS
Prime Downtown Oakville location, this turnkey mixed-use building features two prime commercial units and four residential suites on second floor. This property sits on one of the most coveted blocks in downtown Oakville right on Lakeshore between Navy and Thomas. This offering provides a stable income stream and significant potential for future appreciation and redevelopment. Well-maintained with recent renovations including commercial spaces, windows, roof and appliances.

150 Lakeshore Road E, Oakville
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