1013 - OO Old Oakville Real Estate

1013 - OO Old Oakville Real Estate

Welcome to the enchanting neighborhood of 1013 - OO Old Oakville, a hidden gem nestled in the heart of Oakville, Ontario. Known for its picturesque streets and vibrant community spirit, this charming area offers a perfect blend of suburban tranquility and urban convenience.

Old Oakville is characterized by its stunning tree-lined streets, historic architecture, and beautifully maintained parks. As you stroll through the neighborhood, you’ll be captivated by the charming homes that reflect a rich heritage, with many properties dating back to the 19th century. The blend of classic and modern designs creates a unique aesthetic that appeals to a diverse range of residents.

Families will appreciate the top-rated schools in the area, providing quality education and a nurturing environment for children. The neighborhood is also home to an array of amenities, including boutique shops, cozy cafes, and fine dining options that cater to every palate. The vibrant local arts scene, featuring galleries and cultural events, adds to the area’s charm, making it a hub for creativity and community engagement.

For outdoor enthusiasts, the nearby waterfront offers stunning views of Lake Ontario, perfect for leisurely walks, cycling, or picnicking with loved ones. The local parks, such as the picturesque Bronte Creek Provincial Park, provide ample opportunities for hiking and enjoying nature.

With its ideal location, rich history, and welcoming community, 1013 - OO Old Oakville is not just a place to live; it’s a place to thrive. Come and discover the magic of this delightful neighborhood, where every day feels like a breath of fresh air!

Newest Listings in 1013 - OO Old 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
103-105 Dunn Street, Oakville
$2,498,000
W14140408 MLS
Prime Downtown Oakville Mixed-Use Investment. A rare opportunity to acquire a detached commercial-residential building in the heart of Downtown Oakville, just steps from the Town Square and Lake Ontario. Featuring a remarkable 35 feet of frontage, this well-maintained property offers exceptional versatility for investors, live-work users, or end-users alike. Retail Level: Currently configured as a single expansive retail space totaling approx. 1,879 sq. ft. (originally two separate units). It boasts high ceilings, large display windows for maximum street exposure, plus an approximate 1,000 sq. ft. lower-level storage area with a 2-piece bathroom. Residential Level: Accessed via a secure, charming arched entryway, the second floor features three light and bright apartments: one studio (~363 sq. ft.) and two 1-bedroom units (~525 sq. ft. and ~591 sq. ft.). Tenants also benefit from dedicated lower-level laundry and storage space. Recent significant capital expenses include flat roofing and basement improvements. A standout addition to any investment portfolio. Please respect tenant privacy; viewings strictly by appointment only.

103-105 Dunn Street, Oakville
129 Watson Avenue, Oakville
$4,350,000
4 Beds ⋅ 5 Baths ⋅ W14128732 MLS
5 Elite Picks! Here Are 5 Reasons To Make This Home Your Own: 1. Stunning Custom-Designed Kitchen Boasting Abundant Cabinetry, Oversized Island with Breakfast Bar, Quartz Countertops, Top-of-the-Line Appliances (Including Pizza Oven!) & Double W/O to Porch/Patio, Combined with Bright & Beautiful Dining Room with Gas Fireplace, Ample Oversized Windows & Sun-Filled Sitting/Reading Nook Overlooking the Backyard... Plus Gorgeous Great Room Featuring Ample Oversized Windows, Gas Fireplace & Stunning Custom Coffered Ceiling! 2. Spacious 2nd Level Boasting 3 Large Bedrooms (Each with Custom W/I Closet & Its Own Ensuite!), Office Nook with B/I Desk/Shelving & Beautiful Upper Level Laundry Room with Chic Tile Flooring & B/I Storage. 3. Spacious Primary Bedroom Suite Featuring Bountiful B/I Storage Thruout, Plus W/I Closet/Dressing Room & Breathtaking 5pc Ensuite with Huge Double Vanity, Freestanding Soaker Tub & Large Glass-Enclosed Rain Shower with B/I Seat. 4. Bright & Beautiful Finished Basement with Oversized Windows Boasting Spacious Open Concept Rec/Games Room with Generous Wet Bar Area, Plus Multi-Functional Room (Office, Theatre Room, etc.) with B/I Storage, Stunning 3pc Bath & Large 4th Bedroom with Access to W/I Closet/Fabulous 2nd Laundry with Ample B/I Storage! 5. Gorgeous Private Lot with Oversized Patio, No-Maintenance Artificial Turf (Including Front Yard Putting Green Area!) & Mature Trees & Shrubs, Located in Beautiful Old Oakville Just Steps from Downtown Oakville with Boutique Shopping, Classy Restaurants & Much More! All This & More!! Convenient 2nd Entry to Mud Room with B/I Storage Nook. Striking 2pc Powder Room on Main Level. Solid Hdwd Flooring Thru Main & 2nd Levels. Nearly 3,000 Sq.Ft. A/G Finished Living Space + 1,800 Sq.Ft. in the Finished Basement! 10' Ceilings on Main Level / 9' on 2nd Level & Basement. Dual A/C Units for Efficient Cooling (2nd Unit Added '25)! Heated Flooring in Basement & All Baths!

129 Watson Avenue, Oakville
533 Carson Lane, Oakville
$5,950,000
6 Beds ⋅ 7 Baths ⋅ W14127864 MLS
This magnificent custom residence is nestled in one of Oakville's most prestigious neighbourhoods, just a short stroll from the lake and downtown Oakville. Offering over 6,500 sq. ft. of exquisitely designed living space, this exceptional home seamlessly blends contemporary sophistication with exceptional luxury. Every detail has been meticulously considered, from heated floors on the main and lower levels to a private elevator serving all three floors. A sunlit two-storey foyer introduces an elegant interior defined by refined finishes and thoughtful design. The expansive Great Room features soaring 20-foot ceilings and a dramatic wall of windows overlooking the professionally landscaped grounds. Walk out to an elegant new patio (with new waterproof membrane) with gas BBQ hookup, ideal for summer entertaining and alfresco dining. The gourmet kitchen is a true showpiece, featuring sophisticated two-tone cabinetry, an expansive centre island and state-of-the-art appliances. The adjoining butler's pantry provides additional prep space and connects seamlessly to the elegant Dining Room, where built-in speakers and views of the front gardens create an exceptional setting for entertaining. A serene formal Living Room offers a refined retreat, while the main-floor bedroom, easily converted to an office, features a private ensuite and direct patio access. A sculptural floating staircase leads to the skylit second level, where the luxurious primary suite offers two walk-in closets and a spa-inspired ensuite. Three additional bedrooms, each with secure closets and heated ensuites, provide comfort and privacy. The lower level is an entertainer's dream, featuring a heated underground garage with vehicle turntable, stylish recreation room with walk-up to the backyard, and space for a state-of-the-art theatre or gym. An extraordinary residence offering sophisticated design, exceptional amenities and an unparalleled Oakville lifestyle.

533 Carson Lane, 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
$2,499,900
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
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