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 Old Oakville, a charming gem nestled in the heart of Ontario, Canada. Known for its rich history and picturesque landscapes, this area offers a delightful blend of heritage and modern living, making it one of the most sought-after communities in Oakville.

Old Oakville boasts a variety of homes that beautifully reflect its storied past, with many properties dating back 31 to 50 years. These residences showcase timeless architectural styles, from classic Victorian to contemporary designs, providing a unique character that appeals to families, professionals, and retirees alike. The mature trees lining the streets and the well-maintained gardens create an inviting atmosphere, perfect for leisurely strolls or family picnics.

This vibrant neighborhood is more than just its charming homes; it’s a community filled with life. Residents enjoy easy access to an array of amenities, including boutique shops, cozy cafes, and fine dining options, all within walking distance. The nearby waterfront offers stunning views of Lake Ontario, as well as recreational activities such as sailing, kayaking, and cycling along scenic trails.

Families are drawn to Old Oakville for its excellent educational institutions, both public and private, ensuring that children receive quality education. The community spirit is palpable, with local events and festivals that bring neighbors together throughout the year.

Whether you’re looking for a place to call home or simply want to explore a neighborhood rich in culture and community, Old Oakville is the perfect destination. Experience the charm and warmth of this historic area and discover why so many choose to make it their home.

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

287 MacDonald Road, Oakville
$3,769,000
4 Beds ⋅ 5 Baths ⋅ W14110702 MLS
This completely renovated contemporary residence represents the pinnacle of modern design and sophisticated living in one of Oakville's most desirable locations of Old Oakville.Every detail of this 4 Bedroom | 4+1 Bathrooms | 4,819 Sq Ft Finished Living Space has been meticulously reimagined to deliver an unparalleled standard of quality and craftsmanship.The highly functional main floor plan centers around an exceptionally sleek kitchen open to the Great Room with gas fireplace and walk out to the resort style backyard and pool.The kitchen is outfitted with luxury high-end appliances, an oversized island seating eight, and an additional peninsula for casual entertaining in the bar area.Adjacent to the kitchen, is a walk in pantry with an additional dishwasher and fridge. Not to be missed is the impressive temperature-controlled wine room accommodates approx 1,000 bottles-a striking feature for the discerning entertainer.A versatile family room/main floor bedroom with ensuite which can be used as a principal bedroom or guest suite, laundry room, walk-in main closet for storage and access to oversized double car garage.The 2nd level principal suite is a private sanctuary featuring juliette balcony, gas fireplace, two walk-in closets and a spa-inspired ensuite with heated floors, walk-in shower, and a standalone soaking tub.Two additional spacious bedrooms each with their own ensuites complete the level. Not to be missed is the finished lower level room with added storage in the pantry and crawl space area. The backyard is an entertainer's paradise, showcasing a saltwater pool, two expansive patio areas, two gazebos with a gas fire table, and premium Dutch-imported artificial turf that remains lush year-round with zero maintenance.Ideally situated steps from Whole Foods Market, Oakville GO Train, for seamless transit connectivity,and the Oakville Trafalgar Community Centre this extraordinary property offers both refined luxury and everyday convenience.LUXURY CERTIFIED

287 MacDonald Road, Oakville
54 RAYMAR Place, Oakville
$6,500,000
5 Beds ⋅ 5 Baths ⋅ W14097832 MLS
This exceptional residence has been extensively upgraded with curated enhancements that seamlessly blend timeless architecture with modern luxury, advanced technology and exceptional craftsmanship. Designed for effortless indoor-outdoor living, the enclosed lanai features floor-to-ceiling glass sliding doors on three sides with automated electronic screens for year-round comfort and privacy. The professionally landscaped grounds include a custom 13' x 9' powered garden pavilion, natural stone entertaining terrace, 1,100 sq. ft. wraparound composite deck, approximately 500 sq. ft. of Ipe hardwood privacy screening, luxury hot tub, heated saltwater pool with waterfall, 20-foot motorized retractable awning and a fully automated seven-zone irrigation system and hot tub. The gourmet kitchen has been refreshed w/ custom cabinetry doors and drawer fronts while maintaining its timeless design. Premium appliances include two built-in dishwashers, two wall ovens, integrated refrigerator and freezer, built-in microwave, approximately 100-bottle wine refrigerator and two oversized island prep sinks with garburators. The principal fireplace has been restored with a custom surround, creating a stunning focal point. The luxurious primary suite features restored wood paneling, a custom dressing room, spa-inspired ensuite with freestanding tub, steam shower, heated floors and heated towel warmers. A DuraDek waterproof roof system (2023) was installed over the private terrace. All upper bedroom ensuites also feature radiant heated floors and heated towel warmers. An upgraded Crestron Smart Home system controls lighting, climate, motorized blinds, distributed audio and home automation. The home is equipped with three owned high-efficiency furnaces, three air con. systems, two steam humid., two-zone climate control. Exterior Shower. Every detail has been thoughtfully curated to deliver timeless elegance & intelligent technology.

54 RAYMAR Place, Oakville
221 Robinson Street Unit 307, Oakville
$798,000
2 Beds ⋅ 2 Baths ⋅ W13861848 MLS
Spacious and bright two-bedroom suite in a small, exclusive complex in the heart of downtown Oakville. This prime south-facing suite enjoys treetop views and is ideally situated near the Town Square. A generous foyer with marble flooring welcomes you into the home, leading to a huge, open-concept living and dining area filled with natural light. An extra-large window, California shutters and abundant space create an inviting setting for both everyday living and entertaining. The spacious kitchen features crisp white cabinetry, under-cabinet valance lighting, a built-in breakfast bar/desk and stainless steel appliances. A convenient in-suite laundry room includes a high-capacity washer and dryer. The primary bedroom is a spacious retreat with California shutters and a large walk-in closet with a deluxe organizer. The four-piece ensuite features marble flooring and countertop, white cabinetry, a linen pantry, large tub and separate shower. The generous second bedroom offers a large window, California shutters and double-door closet. A well-appointed four-piece main bathroom includes ample cabinetry and two medicine cabinets. Immaculately maintained and move-in ready, this bright luxury suite is ideally located within walking distance of Lake Ontario, Oakville Harbour and downtown Oakville's charming boutiques, restaurants and cafés, offering everything from casual dining to fine cuisine.

221 Robinson Street Unit 307, Oakville
221 Robinson Street Unit 211, Oakville
$1,249,000
2 Beds ⋅ 2 Baths ⋅ W13843508 MLS
Welcome to exceptional condominium living in the heart of Old Oakville. Beautifully updated and impeccably presented, this sophisticated 2-bedroom, 2-bathroom residence with two parking spaces and a large private locker offers an extraordinary opportunity to live directly on Oakville's renowned Town Square.Thoughtfully designed with timeless finishes, elegant detailing, and modern comfort, this inviting residence delivers a refined lifestyle in one of Oakville's most coveted and walkable locations. Step outside your door and immerse yourself in the very best of downtownOakville-boutique shopping, acclaimed restaurants and cafés, the lakefront, marina,Oakville Centre for the Performing Arts, library, parks, and scenic waterfront trails are all within easy reach.Enjoy the rare privilege of a true urban village lifestyle, where everyday essentials and exceptional amenities are just steps away. Spend your mornings exploring the waterfront, afternoons strolling through the charming streets of Old Oakville, and evenings dining at some of the area's finest restaurants.For commuters, the location is equally impressive, with convenient access to the GO Station,QEW and Highway 403. Nearby trails along Sixteen Mile Creek and Lake Ontario provide a wonderful connection to nature, creating the perfect balance of sophisticated urban living and outdoor enjoyment. A rare opportunity to experience the very best of Old Oakville- an exceptional address, an enviable lifestyle, and refined condominium living without the multi-million-dollar price tag.

221 Robinson Street Unit 211, Oakville
185 Robinson Street Unit 202, Oakville
$699,900
2 Beds ⋅ 2 Baths ⋅ W13612886 MLS ⋅ The Ashbury BLDG.
Live where Oakville comes to life! Downtown Oakville at your doorstep! Impeccably maintained, this beautiful 2-bedroom, 2-bathroom condo blends comfort, style, & convenience with a rare private balcony, all just steps from Oakville's renowned dining scene, boutique shopping, cafés, & picturesque waterfront trails. Offering 975 sf. of thoughtfully designed living space, this bright, carpet-free suite features a functional split-bedroom layout, two walk-in closets, upgraded light fixtures, & an open-concept design that's perfect for both everyday living & entertaining.The stylish kitchen showcases matte black tile flooring, crisp white cabinetry & countertops, & three full-size appliances, including a new dishwasher. Overlooking the spacious great room, it's designed for effortless entertaining, while large sliding glass doors flood the space with natural light & lead to your private balcony.Retreat to the spacious primary suite featuring a walk-in closet, a 4-pc ensuite w/ a glass-enclosed shower, & direct access to the balcony-the perfect spot to enjoy your morning coffee or unwind at the end of the day. The generously sized second bedroom also offers a walk-in closet, while the main 4-pc bathroom features tile flooring & a glass-enclosed shower.An in-suite laundry room w/ additional cabinetry & storage adds everyday convenience, while a new fan coil 2026 provides added peace of mind.Complete w/ one underground parking space & one locker, this home truly checks every box. This boutique-style, low-rise condominium is exceptionally well managed & features beautifully updated common areas, a party room, visitor parking, & a landscaped courtyard.Nestled in the heart of charming Downtown Oakville, you're just moments from boutique shops, bakeries, cafés, acclaimed restaurants, the Oakville Centre for the Performing Arts, & the scenic waterfront.Enjoy lakeside strolls, downtown dining, shopping & all that Downtown Oakville has to offer. Welcome to a lifestyle you'll love!

185 Robinson Street Unit 202, Oakville
488 Macdonald Road, Oakville
$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
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