1013 - OO Old Oakville Homes for Sale

1013 - OO Old Oakville Homes for Sale

Welcome to 1013 - OO Old Oakville, a charming enclave nestled in the heart of one of Ontario's most sought-after towns. Known for its picturesque streets, lush greenery, and a vibrant community spirit, Old Oakville is the perfect blend of historic charm and modern living.

As you stroll through this enchanting neighborhood, you'll be captivated by its tree-lined avenues, beautifully maintained heritage homes, and the welcoming atmosphere that makes it feel like a true community. The area is steeped in history, with many of its buildings reflecting the architectural elegance of days gone by, while contemporary amenities seamlessly integrate into the landscape.

Residents of Old Oakville enjoy an array of local boutiques, cafes, and fine dining options, all just a stone’s throw from their front doors. The nearby waterfront, with its stunning views of Lake Ontario, offers a perfect escape for outdoor enthusiasts and families alike, featuring parks, walking trails, and recreational activities.

For those considering a move, there are a variety of homes for sale in this desirable neighborhood. Whether you're seeking a cozy bungalow, a spacious family home, or a luxurious estate, Old Oakville has something to suit every taste and lifestyle. With its strong sense of community, excellent schools, and proximity to major highways and transit options, this area is ideal for families, professionals, and retirees alike.

Discover the charm of Old Oakville and find your dream home today in this enchanting neighborhood where history and modernity coexist beautifully!

Newest 1013 - OO Old Oakville Homes for Sale

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
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
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
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
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
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
426 Trafalgar Road, Oakville
$4,099,000
4 Beds ⋅ 6 Baths ⋅ W13843702 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 façade. 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
374 Spruce Street, Oakville
$1,899,000
4 Beds ⋅ 4 Baths ⋅ W13833914 MLS
**EXCEPTIONAL LOCATION. RARE 60' x 142' LOT. OUTSTANDING OPPORTUNITY IN THE HEART OF OAKVILLE.**Welcome to 374 Spruce Street, ideally situated within walking distance of **Downtown Oakville, the GO Train and Old Oakville Marketplace**. This is a rare opportunity to secure a substantial property in one of Oakville's most desirable and established neighbourhoods. Set on an impressive **60' x 142' lot**, the property offers exciting possibilities for the next owner. Build a stunning new home of approximately **4000 sq. ft.**, subject to approvals, or embrace the existing home and undertake a complete renovation to create your ideal residence. The generous lot provides plenty of room to design a home that suits your lifestyle, while the exceptional location puts some of Oakville's best amenities right at your doorstep. Enjoy the convenience of walking to the charming shops, restaurants and cafés of Downtown Oakville, commuting easily via the GO Train, or accessing everyday shopping and services at Old Oakville Marketplace. Whether you're a builder looking for an outstanding opportunity, a family ready to create a custom home, or a buyer with a vision for transforming the existing residence, **374 Spruce Street offers flexibility, location and long-term potential.****Rare 60' frontage. Exceptional walkability. Established Oakville location. Priced to sell.**

374 Spruce Street, Oakville
139 Allan Street, Oakville
$2,749,000
4 Beds ⋅ 3 Baths ⋅ W13798472 MLS
A rare combination of character, space and exceptional walkability in the heart of Downtown Oakville. Set on an impressive 70-foot-wide property, this beautifully renovated four-bedroom home blends the charm of an established residence with the quality and functionality of a thoughtful, high-end renovation. Extensively updated by Stonewood Homes, the interior features wide-plank white oak flooring, exposed wood beams, natural stone fireplaces and custom millwork throughout. The main level offers an impressive collection of living spaces, beginning with a bright enclosed sunroom and flowing through separate living and dining rooms to the open-concept kitchen and family room at the rear of the home. The kitchen is beautifully appointed with custom Chervin cabinetry, high-end appliances and a large centre island with seating. A substantial walk-through servery provides exceptional storage complete with additional cabinetry, sink, beverage refrigeration and wine storage. Upstairs, four bedrooms include a spacious primary suite with a walk-in closet and a beautifully finished ensuite featuring a freestanding tub. Three additional bedrooms and a second full bathroom provide an ideal layout for family living. The finished lower level adds valuable living space with a large recreation room, laundry room, workshop and extensive storage. Outside, the unusually wide lot allows for multiple outdoor living spaces surrounded by mature trees that create a wonderful sense of privacy. A large rear deck extends the main living area outdoors, while the landscaped backyard leads to a separate covered pavilion. Adding to the property's appeal is a detached two-car garage and two separate driveways, a rare offering this close to Downtown Oakville. Located just steps from the restaurants of downtown, and within easy reach of the lakefront, harbour, parks and schools, this is a unique opportunity to enjoy one of Oakville's most desirable and walkable neighbourhoods.

139 Allan Street, Oakville
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