1013 - OO Old Oakville Real Estate

1013 - OO Old Oakville Real Estate

Welcome to 1013 - OO Old Oakville, a charming neighborhood that beautifully blends historical elegance with modern convenience. Nestled in the heart of Oakville, Ontario, this area is renowned for its picturesque streets, tree-lined avenues, and a vibrant community spirit that makes it one of the most desirable places to live in the Greater Toronto Area.

Old Oakville is steeped in rich history, with many heritage homes dating back to the 19th century, showcasing stunning architectural designs that reflect the area’s storied past. As you stroll through the neighborhood, you'll be captivated by the quaint boutiques, artisanal cafes, and gourmet restaurants that line the streets, offering a delightful mix of shopping and dining experiences right at your doorstep.

Families will appreciate the top-rated schools and proximity to numerous parks and recreational facilities, providing ample opportunities for outdoor activities. The serene waterfront along Lake Ontario is just a stone's throw away, inviting residents to enjoy scenic walks, picnics, and breathtaking sunsets.

Old Oakville is also well-connected to major highways and public transit, making commuting to Toronto and surrounding areas a breeze. With a strong sense of community and a calendar full of local events, including farmers' markets and seasonal festivals, there’s always something happening that brings neighbors together.

In 1013 - OO Old Oakville, you’ll find not just a home, but a lifestyle that embraces both tranquility and vibrancy. Discover the charm of this remarkable neighborhood and make it your own—where every day feels like a retreat in the heart of Oakville!

Newest Listings in 1013 - OO Old Oakville

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
254 Donessle Drive, Oakville
$5,349,000
6 Beds ⋅ 6 Baths ⋅ W14110352 MLS
From the moment you arrive, 254 Donessle Drive makes a lasting impression. Stately and estate-like, this meticulously maintained residence showcases timeless architecture, exceptional craftsmanship and the generous proportions of a distinguished family home.Set on a magnificent 108' x 192' west-facing property on one of Southeast Oakville's most coveted streets, the home offers approximately 7,531 sq. ft. of living space amid mature trees, established gardens and remarkable privacy.A soaring two-storey foyer introduces rich hardwood floors, exquisite millwork and elegant principal rooms. The dramatic two-storey living room features towering windows, French doors and a floor-to-ceiling stone fireplace. A wood-panelled executive den and formal dining room provide refined spaces for work and entertaining.The expansive kitchen features custom Downsview cabinetry, a 13' island with granite countertop and Wolf and Sub-Zero appliances. Open to the breakfast area and fireside family room, it forms the heart of the home.Upstairs, four bedrooms each enjoy a private ensuite. The primary retreat includes a fireplace, custom walk-in closet and luxurious five-piece bath with heated floors, steam shower and air-jet tub. The finished lower level offers a recreation room, custom bar, wine cellar, gym and two additional bedrooms.Outside, the west-facing gardens are equally impressive, with a heated saltwater pool, custom cabana with bar and change room, stone terraces and expansive lawns-an exceptional setting for afternoon sun and evening entertaining. A triple-car garage, fitted mudroom and abundant storage complete the home.Moments from the lake, excellent schools and local amenities, 254 Donessle Drive is a rare opportunity to own a home of enduring quality, where the grounds are every bit as remarkable as the residence itself. Luxury Certified.

254 Donessle Drive, Oakville
121 Lakeshore Road W Unit 5, Oakville
$1,549,900
3 Beds ⋅ 4 Baths ⋅ W14105644 MLS
Beautiful, fully renovated freehold live/work property offering exceptional versatility inprime area of Downtown Oakville. Ideal for business owners, investors, this turnkey property features distinct commercial and residential components. The commercial unit with excellent visibility spans approximately 880 sqft. with high ceilings, dedicated office/kitchenette, and a 2-piece washroom. The residential 3-story layout features bright, open-concept living with generous principal rooms and large windows throughout. The layout includes 3 bedrooms, 2.5bathrooms, second-floor laundry and a private primary bedroom retreat complete with a walk-in closet and spa-inspired ensuite. Upgrades include wooden floors throughout, potlights, newer appliances, granite counters, custom made kitchen cabinets and built-in wall unit. Enjoy outdoor entertaining on the private rooftop terrace with sunset views. Fantastic location, steps to Oakville marina, lake, waterfront trails, cafes, and restaurants, with quick access to the GO Train, QEW, and 407.

121 Lakeshore Road W Unit 5, 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
146 Reynolds Street, Oakville
$2,598,000
3 Beds ⋅ 4 Baths ⋅ W14088748 MLS
Welcome to sophisticated downtown Oakville living. This beautifully renovated luxury townhome offers over 2700sq.ft. of total living space, an exceptional combination of elegant design, generous spaces, and an unbeatable walkable location. Thoughtfully updated throughout with quality finishes and timeless style, this turnkey residence is ideal for discerning buyers seeking a refined, low-maintenance lifestyle in one of Oakville's most coveted neighbourhoods. The bright and spacious main living area is designed for comfort and effortless entertaining. Expansive living and dining areas are filled with natural light and flow seamlessly into a stunning renovated kitchen featuring premium appliances, extensive custom cabinetry, an oversized centre island, abundant storage, and a functional layout that will impress the most avid home chef. Step directly from the kitchen onto a large private deck, creating the perfect extension of your living space for outdoor entertaining, or simply enjoying a quiet morning coffee. Offering 2+1 bedrooms and 3+1 bathrooms, this home provides remarkable flexibility for families, professionals, and downsizers alike. The spacious primary retreat offers comfort andprivacy, while additional bedrooms accommodate family and guests with ease. A dedicated main floor office creates the ideal work from home environment, providing separation from the main living spaces without sacrificing convenience. The walk-up from the lower level presents endless possibilities and is perfectly suited for a nanny suite, in-law accommodation, guest quarters, home gym, or additional living space. With its own direct access, this level adds tremendous versatility to an already exceptional floorplan. Outdoor living is further enhanced by two private decks, offering multiple spaces to relax and entertain. A rare attached double car garage, combined with parking for an additional vehicle in the back drive, provides convenience seldom found in downtown locations.

146 Reynolds Street, Oakville
343 Douglas Avenue, Oakville
$4,265,000
5 Beds ⋅ 6 Baths ⋅ W14083808 MLS
An exceptional opportunity to secure pre-construction pricing in the heart of Old Oakville. Completion is anticipated for September 2027. Photos are of the builders work to show detail and craftsmanship. This lot is tucked along one of the neighbourhood's most coveted streets, and this custom residence offers an exceptionally private, tree-lined setting just a stroll from downtown's shops, restaurants, and waterfront. Refined finishes, thoughtful proportions, and exceptional craftsmanship define the home, complemented by a rarely offered double-car garage and fully finished lower level. With a dedicated interior designer guiding your selections throughout the build, each finish becomes an opportunity to make the home distinctly yours. An optional elevator is available. Crafted by a trusted custom builder with nearly 20 years of experience, this is a rare chance to shape a timeless home in a prestigious, walkable neighbourhood. Drawings are approved by the Committee of Adjustment, the permit process is underway.

343 Douglas Avenue, Oakville
305 Randall Street, Oakville
$2,998,000
3 Beds ⋅ 4 Baths ⋅ W13886706 MLS
SPECTACULAR LUXURY TOWNHOME IN THE HEART OF DOWNTOWN OAKVILLE! This stunning freehold end-unit residence offers approx 2,950 sq. ft. of luxurious living space and has been completely transformed from the studs with exceptional craftsmanship and high-end finishes throughout. Offered fully furnished and professionally designed, this turnkey home features 2+1 bedrooms, 4 baths, oak hardwood flooring, two fireplaces and a custom Brahms kitchen. A separate entrance to the lower level adds convenience and versatility. Enjoy a private terrace off the kitchen and a private rooftop terrace, ideal for outdoor entertaining. A rare double-car garage with parking for three vehicles completes this exceptional offering. Perfectly situated steps from downtown Oakville's finest restaurants, boutiques, cafés and waterfront. An extraordinary opportunity to enjoy sophisticated, maintenance-free luxury living in one of Oakville's most desirable locations. Simply move in and enjoy!

305 Randall Street, Oakville
317 Gloucester Avenue, Oakville
$5,130,000
4 Beds ⋅ 4 Baths ⋅ W13879172 MLS
Timeless Elegance in the Heart of Olde Oakville. A rare property on one of the community's most coveted streets. Experience refined living in this exceptional residence set on a triple lot over 1/2 acres with an impressive 154.73ft frontage, curated for those who value privacy, design and indoor-outdoor living at its finest. Beautifully reimagined in 2024 & 2026, the main level showcases a sophisticated blend of transitional elegance and casual upscale comfort, perfect for both everyday living and effortless entertaining. A Main Floor Redesigned for Modern Luxury. Step inside to wide-plank oak hardwood floors, luxurious finishes, and stunning sightlines to the property's park-like grounds. The custom kitchen is a true showpiece, featuring: Main kitchen+ second "messy kitchen" for concealed prep, storage, and small appliances. Square island with integrated fridge/freezer drawers. Quartz countertops & full-height backsplash in both kitchens. Built-in wine/beverage and dedicated coffee station. A walk-out from the dining room and a large picture window open to views of the serene screened-in sun porch ,creating a seamless flow for indoor-outdoor enjoyment. The magnificent great room features dramatic cathedral ceilings, a stone wood-burning fireplace with aged beam mantel. A second walk-out continues to the sun porch framed by nature. The upper level has been thoughtfully elevated with beautiful new wide plank oak hardwood flooring creating a warm and sophisticated foundation for the home. This exceptional level features flexible living spaces with 4 bedrooms and 3 full bathrooms offering both comfort and functionality. Third floor loft/suite ideal as 4th bedroom, guest suite or office. Every detail has been carefully considered, including new custom window coverings throughout & beautifully appointed spaces filled with natural light.

317 Gloucester Avenue, Oakville
337 Lakeshore Road E, Oakville
$149,000
W13869580 MLS
Rare opportunity to acquire the original Sunnyside Grill in a desirable Old Oakville location. This established restaurant offers a well-maintained space with evident pride of ownership and an inviting setting for patrons.The restaurant specializes in breakfast and lunch offerings, providing a selection of popular breakfast favourites and lunch-style meals. An opportunity for an owner-operator or experienced restaurateur to continue the existing concept. Conveniently located in Old Oakville, surrounded by established residential neighbourhoods, local businesses, shopping, services and other amenities. The location provides an excellent setting for a restaurant serving the local community.A rare opportunity to acquire the original Sunnyside Grill and establish your presence in one of Oakville's well-known communities. Business, chattels, equipment and other inclusions are subject to the terms of the sale. Buyers and their representatives are advised to conduct their own due diligence regarding financials, lease, licensing, zoning and permitted uses.

337 Lakeshore Road E, Oakville
60 Old Mill Road Unit 409, Oakville
$599,900
2 Beds ⋅ 2 Baths ⋅ W13863414 MLS
Step into Oakridge Heights, tucked into the heart of Oakville and just minutes from Highway 403 and the Oakville GO, so getting anywhere is a breeze (though once you see the place, you might not want to go anywhere at all). This bright corner 2-bed, 2-bath suite has that open, light-filled feel that makes a home easy to love, with an electric fireplace for cozy nights in and a private balcony for your morning coffee on sunny ones. The primary bedroom is a real retreat, with a full four-piece ensuite and a true walk-in closet (actual walk-in space, not a "closet" in name only). The second bedroom has its own three-piece cheater ensuite, so it works just as well for guests, a roommate, or the home office you keep meaning to set up. The building amenities could fill a weekend: indoor pool, gym, sauna, billiards room and party room, plus visitor parking so friends aren't circling the block when you host. Your own underground parking spot means no scraping ice off the windshield and no frosty starts on January mornings. Around you is one of Oakville's most sought-after neighbourhoods, close to great shopping, dining, parks, waterfront trails and an easy commute into Toronto. It's comfortable, convenient and well located, and it doesn't need to oversell any of that. And here's the bonus: we're offering $5,000 toward new appliances, so you can make it yours from day one.

60 Old Mill Road Unit 409, 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
25 Howard Avenue, Oakville
$2,799,999
5 Beds ⋅ 2 Baths ⋅ W13858982 MLS
Rare opportunity in coveted Orchard Beach, just steps from Lake Ontario and the waterfront trail. Set on a premium 50 x 160 ft lot, this property comes with completed architectural and engineering drawings and Committee of Adjustment approval for a proposed 3,800 sq ft residence. An exceptional offering for a buyer looking to move forward with confidence, with extensive completed work including floor plan and exterior concepts, colour renderings, arborist report, architectural drawing package, sealed roof truss package, sealed LVL layout, sealed structural engineering package, HVAC design, grading and drainage plan, soil test, and stormwater management report.The existing home was updated in 2024 with electrical improvements, a renovated bathroom, updated flooring, a new kitchen, and new appliances, offering flexibility to live in or hold the property while completing the final permit stage. Zoning and Committee of Adjustment approvals are already in place, with remaining steps in progress. Located a short stroll from downtown Oakville, the lake, and top schools, this is a rare opportunity to secure a prime property with meaningful value already created.

25 Howard Avenue, Oakville
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