1013 - OO Old Oakville Real Estate

1013 - OO Old Oakville Real Estate

Welcome to 1013 - OO Old Oakville, a charming enclave nestled in the heart of Oakville, Ontario. This picturesque neighborhood effortlessly blends historic charm with modern convenience, making it one of the most sought-after locations in the Greater Toronto Area.

Old Oakville is renowned for its tree-lined streets, beautifully restored heritage homes, and a vibrant community spirit. As you stroll through the area, you’ll be captivated by the quaint boutiques, artisanal cafes, and gourmet restaurants that dot the landscape. The local shops along Lakeshore Road offer a delightful shopping experience, while the nearby Oakville Place shopping mall provides a more extensive retail selection.

For those who appreciate the outdoors, Old Oakville boasts stunning waterfront parks and scenic trails along Lake Ontario, perfect for leisurely walks, cycling, or simply soaking in the natural beauty. The nearby Bronte Creek Provincial Park offers additional recreational opportunities, including hiking and picnicking.

Families will appreciate the excellent educational institutions in the area, with top-rated public and private schools ensuring a high-quality education for children of all ages. The community’s commitment to family-friendly living is evident in its numerous parks and playgrounds, making it a wonderful place to raise a family.

With its rich history, vibrant community, and proximity to Toronto, 1013 - OO Old Oakville is more than just a location; it’s a lifestyle. Whether you’re looking to settle down or find a charming getaway, this neighborhood promises to deliver an unparalleled living experience that blends the best of urban and suburban life. Come discover the magic of Old Oakville!

Newest Listings in 1013 - OO Old Oakville

336 Maple Avenue, Oakville
$2,188,000
3 Beds ⋅ 3 Baths ⋅ W14162928 MLS
Welcome to this charming family home in desirable Old Oakville, ideally located near Oakville GO Station, downtown Oakville, Highway 403, the QEW and the lake. Warm oak hardwood flooring and inviting living spaces create a comfortable setting for everyday living and entertaining. The open-concept living and dining areas feature a fireplace and double French doors with a walkout to the outdoors. The renovated kitchen offers granite countertops, high-end appliances, including a new dishwasher, microwave and refrigerator, and a cozy breakfast nook with custom built-in bench seating. A character-filled family room features a second fireplace, custom built-in bookshelves and decorative wood accent beams, with convenient access to the mudroom, two-piece bathroom and wooden deck. The primary bedroom offers a dedicated study area, walk-in closet and three-piece ensuite with marble tile flooring and a shower. Two additional bedrooms, each with double closets, share another three-piece bathroom. The private backyard is designed for relaxation and entertaining, featuring an in-ground swimming pool with a new heater, new filter and robotic pool cleaner. Beautiful gardens with an irrigation system surround the outdoor space, while a built-in BBQ, new hot tub and built-in fire pit create the perfect setting for summer gatherings. The full basement is partially finished and includes an additional bedroom. Additional features include a new furnace and air-conditioning system, new washer and dryer, whole-house water softening system and central vacuum. An inviting family home offering comfortable indoor living and exceptional outdoor entertaining, all in a sought-after Old Oakville location.

336 Maple Avenue, Oakville
426 Trafalgar Road, Oakville
$3,949,000
4 Beds ⋅ 6 Baths ⋅ W14162108 MLS
A private retreat in the heart of South East Oakville, with the city at your doorstep. Driving south on Trafalgar Road, this expansive Tudor is one of the first homes to welcome you into SE Oakville. What makes this residence special is what happens beyond its distinguished facade. Step into the backyard & the world changes: mature trees, ravine, 16 Mile Creek & complete privacy create a setting wonderfully removed from the city. Enjoy morning coffee overlooking the creek, dinner in the outdoor kitchen, evenings around the fire pit, or simply relax beneath the trees & enjoy the wildlife & changing seasons. With riparian rights, professionally landscaped gardens, perennial beds, flowering trees, hedges, timber deck, pergola, gazebo, Napoleon & Lynx outdoor kitchen, the backyard feels like a private escape. Inside, this beautifully maintained Tudor offers 3,000+ sqft. 4 bedrooms, 6 bathrooms. Exceptional craftsmanship includes Jatoba hardwood, handmade plaster crown moulding, 8-inch baseboards, Ciot tile, Hansgrohe fixtures & triple-pane windows. The renovated kitchen features custom cabinetry, premium granite & Viking, Wolf & Miele appliances, while the breakfast & family rooms capture spectacular ravine views. The primary suite is a private retreat with three skylights, unobstructed views of the16 Mile Creek, a private balcony & a custom dressing room. The spa-inspired ensuite features a Neptune air-jetted tub & glass shower. Improvements include updated kitchen finishes & flooring, custom fireplace cabinetry, extensive pot & art lighting, new owned furnace, AC & hot water tank, 200-amp service, wine cellar, irrigation, security & smart-controlled systems. Location is exceptional: approximately a 3-minute walk to Oakville GO, under 5 minutes to Downtown Oakville & Lakeshore, & walking distance to groceries, restaurants & shops. QEW, 407 & 410 access is minutes away. Enjoy the peace & privacy of nature while remaining effortlessly connected.

426 Trafalgar Road, Oakville
335 Helen Lawson Lane, Oakville
$3,199,000
3 Beds ⋅ 4 Baths ⋅ W14159132 MLS
Poised within Fernbrook's newest Old Oakville community, 335 Helen Lawson Lane presents a rare fusion of architectural refinement, modern convenience, and effortless ownership. Brand-new and never occupied, this luminous end-unit townhome offers three bedrooms, three bathrooms, an attached garage, and more than $300,000 in thoughtfully curated upgrades. Natural light animates every level, while a private elevator connects the residence with exceptional ease. The ground-floor family room extends to a secluded backyard and includes generous storage, appliance rough-ins, and provisions for a future bar-an elegant foundation for entertaining or offering guest accommodations with the 3 pc bath.. Above, the principal living level is composed for gracious gatherings. The Downsview kitchen is appointed with Wolf, Sub-Zero, and Cove appliances, a beverage refrigerator, and a walk-in pantry and large upgraded centre island. The open concept living room offers a walk out to deck and a gas fireplace creates a sophisticated focal point. The separate dining area gives the perfect space for entertaining family and friends. A powder room completes the floor. The bedroom level reveals a tranquil primary retreat with walk out to deck and a rough-in for an additional gas fireplace. Two spacious walk in closets and a spa-inspired four-piece ensuite complete this special space. Two further bedrooms share a beautifully appointed four-piece bath, while the laundry room provides a sink and practical storage. The unfinished basement adds valuable flexibility for storage or future customization. Moments from Whole Foods Market, Oakville GO Station, downtown boutiques, acclaimed dining, and Lake Ontario. This distinguished residence offers turnkey luxury in one of Oakville's most connected settings. Need some designer ideas to complete your new home look? The Seller will offer 10 hours of designer time with Khachi Design. Luxury Certified

335 Helen Lawson Lane, 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 light and bright, with 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
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