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$1,920,000
6 Beds ⋅ 3 Baths ⋅ W12894154 MLS
Gorgeous Family Home on Prestigious Chartwell Road in Old OakvilleNestled on a prime 0.29-acre west-facing lot backing onto serene woodlands, this immaculate 4+2 bedroom residence is situated on the coveted "Street of Dreams" Chartwell Road in the heart of highly sought-after Old Oakville. Offering endless potential, this exceptional property is ideal for families looking to move in, renovate, or build their custom dream home in a prestigious neighbourhood.The beautifully maintained home features gleaming hardwood floors, spacious living, dining, family principal rooms, and a thoughtfully updated patio and deck perfect for outdoor entertaining. The finished basement, with a private separate entrance, includes a 2-bedroom in-law suite complete with a full kitchen and bathroom, offering incredible flexibility for multigenerational living or rental income.Enjoy unparalleled convenience with a short walk to Whole Foods, Longos, charming local restaurants, top-rated schools, and minutes to the GO Station and QEW. This is a rare opportunity to own a slice of Oakville's most desirable enclave where lifestyle, luxury, and location meet.

494 Chartwell Road, Oakville
$1,549,000
4 Beds ⋅ 4 Baths ⋅ W13609074 MLS
Prized Location Matters! Top-Rated Private and Public Schools! Key Commuter Routes! Charming family home nestled in the heart of Old Oakville, one of the area's most sought-after neighbourhoods. Meticulously maintained 1.5-storey residence on a beautifully landscaped 50' x 141.8' lot, tucked away on a quiet, tree-lined cul-de-sac. Surrounded by inviting covered porches and decks, a peaceful setting to enjoy nature while remaining close to all amenities. Originally purchased over 40 years ago as a quaint cottage with a garage, large addition/renovation completed 1992, generously sized principal rooms, including a sunken, oversized family room showcasing a reclaimed brick faced, wood-burning fireplace with a barn board mantel, along with a matching bar and sliding doors that open to a Muskoka-inspired backyard. Expansive rear-facing windows flood the home with natural light and lead to a spacious 36'4" x 14'6" deck-perfect for entertaining or relaxing year-round. With over 2,050 sq. ft. of above-grade living space, this home seamlessly blends timeless character with modern comfort. The home offers 3+1 bedrooms, 2 ensuites, +2 bathrooms, and a versatile living room currently used as a formal dining space. The finished basement provides additional flexibility for growing families. The main floor includes a bedroom that can also serve as a home office or den, along with an updated bathroom. Hardwood flooring and ceramic tiles enhance the main level, while the spacious kitchen features abundant cabinetry, a large pantry, and a double sink. Additional highlights include a separate main floor laundry room with a utility sink, folding counter, and ample storage. At the rear of the property, two detached outbuildings with electricity offer excellent potential for a garage, workshop, studio, or garden storage. Long term value with endless possibilities for renovation or addition. Downtown Oakville, Whole Foods, LCBO, charming shops, the lakefront, parks, walk to GO transit

322 Pine Avenue, Oakville
$1,397,000
3 Beds ⋅ 3 Baths ⋅ W13417488 MLS
Penthouse Perfection with Lake Ontario & Toronto Skyline Views. Welcome to Oakridge Heights, one of Oakville's most prestigious addresses, where this 1,956 square foot, 3-bedroom, 2.5-bath penthouse delivers a rare combination of size, style, and spectacular wraparound views. Renovated to exacting standards, this home offers an open, light-filled layout with south exposure over the Sixteen Mile Creek with vistas of Lake Ontario and east exposure to the glittering Toronto skyline, enjoyed from a private wraparound balcony that spans multiple living areas and offers an additional 486 square feet of space. The owners have invested heavily in this beautiful suite, upgrading it to its present stylish state since they purchased it in 2019. No expense has been spared, and the new owner will benefit from the ultimate turnkey experience, able to relax and enjoy all that this spectacular unit has to offer. For commuters, access to the Oakville GO station and the highway is a dream. A brisk 15 minute walk to downtown Oakville. Whole Foods and other gourmet shopping is just down the road. Two side by side parking spaces right by the elevator, and two lockers. Get in soon before you miss your opportunity!

60 Old Mill Road Unit PH1, Oakville
$1,099,900
3 Beds ⋅ 2 Baths ⋅ W13148192 MLS
Welcome to Oakridge Heights in coveted Old Oakville, where bespoke design, elevated finishes, and effortless convenience come together in a truly refined condominium residence. Thoughtfully renovated with a discerning eye, this 2 bedroom + den, 2 bathroom suite offers a sophisticated sense of flow, with wide-plank flooring, expansive floor-to-ceiling windows, and sweeping treetop and lake views that bring a quiet elegance to every principal space. The open-concept living and dining area is warm, stylish, and inviting, featuring custom lighting, balcony access, and a seamless connection to the designer kitchen. Finished with dramatic stone countertops and backsplash, sleek flat-panel cabinetry, stainless steel appliances, built-in oven and microwave, and a waterfall-style peninsula, the kitchen makes an impressive statement. The suite also features a well-designed home office with custom built-ins, a spacious primary bedroom with panoramic views, luxurious 5 pc ensuite beautifully updated bathrooms with glass showers, designer tile, gold and black accents. A well-appointed second bedroom, stylish 3-piece bathroom, dedicated office with French door and built-in shelving/desk, plus in-suite laundry with stackable washer/dryer and laundry sink add everyday function and comfort. Residents enjoy outstanding building amenities, including an indoor pool, gym, hobby room, and party space. Ideally positioned just steps to the GO/VIA Station, Whole Foods, and Olde Oakville Market Place, and only a short stroll to downtown Oakville's boutiques, restaurants, lakefront, parks, and trails, this exceptional residence offers a polished lifestyle with easy highway access and a convenient commute to downtown Toronto. Thoughtfully finished from top to bottom, this condo blends comfort, style, storage, and incredible views in one sophisticated package.

50 Old Mill Road Unit 703, Oakville
$799,900
2 Beds ⋅ 2 Baths ⋅ W13022402 MLS
Welcome to this beautifully updated 2-bedroom, 2-bath, with parking condo right on Oakville's renowned Town Square. With tasteful finishes and a timeless design, this residence offers elegant living in one of the most walkable and coveted locations in town. Enjoy sunset views from your covered terrace, steps from boutique shops, acclaimed dining, the lake, marina, and the Oakville Centre for the Performing Arts. The building itself has been fully refreshed inside, blending classic sophistication with modern comfort. Includes one parking space, with guest parking available. A rare opportunity to live in the heart of Old Oakville without the million-dollar price tag.

185 Robinson Street Unit 315, 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
$599,900
2 Beds ⋅ 2 Baths ⋅ W13129896 MLS
Welcome to Oakridge Heights - right in the heart of Oakville and perfectly placed just minutes from Highway 403 and the Oakville GO. Translation? Getting around is easy, if you need to go somewhere. But we think you'll feel right at home here, and won't need to leave. This bright, corner 2-bed, 2-bath unit has that airy, open feel you want, plus an electric fireplace for those cold, moody nights and a private balcony for the sunny ones. Best of both worlds. The primary bedroom comes with a full four-piece ensuite and a proper walk-in closet (not one of those "technically a closet" situations). The second bedroom pulls its weight too, with its own three-piece cheater ensuite - great for guests, roommates, or a home office setup. As for amenities? You're covered. Indoor pool, gym, sauna, billiards room, party space - it's all here. There's even visitor parking on site, so hosting doesn't turn into a logistical nightmare. And you'll never have to start a cold engine with your own underground parking space. Set in one of Oakville's most sought-after communities, you're close to great shopping, dining, parks, waterfront trails, and easy transit into Toronto. Basically, it's comfortable, convenient, and checks all the boxes - without trying too hard. Bonus - now offering $5000.00 towards new appliances.

60 Old Mill Road Unit 409, Oakville
$575,000
W13427514 MLS
Long established family owned and operated bakery in the heart of downtown Oakville, proven profitable business with consistent yearly growth and a loyal customer base. Includes all equipment recipes and procedures, unique open concept Theatre Baking in full view of customers. Owners retiring after over 40 years in business. Best suited for an owner operator with previous baking/food industry experience.

184 Lakeshore Road E, Oakville
$525,000
1 Beds ⋅ 1 Baths ⋅ W13587226 MLS
Welcome To Suite 204 At 40 Old Mill Road, A Beautifully Maintained Executive Suite Nestled In The Heart Of Prestigious Old Oakville. This One Bedroom Residence Offers 725 Square Feet Of Thoughtfully Designed Open-Concept Space For Comfortable Everyday Living And Effortless Entertaining. Featuring 9 Ft Ceilings, Rich Hardwood Flooring, Elegant Crown Moulding, And Large Windows That Fill The Space With Natural Light, This Suite Exudes Warmth And Timeless Appeal. The Kitchen Is Appointed With Granite Countertops, Upgraded Cabinetry, And Ample Storage, Seamlessly Flowing Into The Combined Living And Dining Area. A Charming Juliette Balcony Enhances The Living Space, While The Generous Primary Bedroom Offers A Walk-In Closet And A Large Window For A Bright And Airy Retreat. The Well-Appointed Bathroom Features A Marble Tub/Shower Alongside A Separate Glass Shower, Providing Both Function And Luxury. Ensuite Laundry With Additional Storage Adds Everyday Convenience. This Sought-After Building Is Known For Its Exceptional Amenities Including Concierge Service, Indoor Pool, Fitness Centre, Party Room, And Visitor Parking, Offering A Refined Lifestyle In A Secure And Well-Managed Community. Ideally Located Just Steps To The Oakville GO Station, Shopping, Parks, And The Scenic Trails Of Sixteen Mile Creek, And Only Minutes To Downtown Oakville's Charming Boutiques, Restaurants, And Lakefront. Situated Within The Highly Regarded Oakville Trafalgar School District, This Residence Is Perfect For First-Time Buyers, Downsizers, Or Investors Seeking A Prime Location And Turnkey Living In One Of Oakville's Most Desirable Neighbourhoods.

40 Old Mill Road Unit 204, Oakville
$514,900
2 Beds ⋅ 1 Baths ⋅ W13610030 MLS
Welcome to Oakridge Heights, where comfort, convenience, and lifestyle come together in the heart of Old Oakville. This bright and beautifully maintained 1+1 bedroom condo offers an ideal layout for young professionals, couples, downsizers, or anyone seeking flexible living space. The spacious primary bedroom features hardwood flooring, double closets, and semi-ensuite access to a 4-piece bath complete with a relaxing whirlpool tub. Soaring 9-foot ceilings and an open-concept living/dining create an airy, inviting atmosphere throughout. The versatile den is perfect as a home office, guest room, nursery, or creative studio-adapting effortlessly to your lifestyle. Complete with 1 parking space and 1 locker, this home offers both convenience and functionality. Commuters will love the easy access to the GO Station, QEW, and Highway 403, while weekends can be spent exploring Downtown Oakville's vibrant shops, cafés, and restaurants. Enjoy nearby trails along 16 Mile Creek and the shores of Lake Ontario, offering the perfect balance of urban convenience and outdoor living. Whether you're starting your next chapter together or looking for a stylish space to call your own, this Oakville gem is ready to welcome you home.

50 Old Mill Road Unit 706, Oakville
$450,000
4 Baths ⋅ W13555454 MLS
Excellent approx. 2,200 sq.ft. restaurant in the heart of Downtown Oakville right on Thomas St with an amazing outdoor patio. Currently an Italian Restaurant called "Buca di Bacco" with a full Kitchen, Exhaust Hoods, and Walk-in Fridge. Very busy and well known restaurant in Oakville. Very attractive buildout with modern and high end leasehold improvements, equipment, and furniture. Easy to operate and has Liquor License of 65. Can be Converted to many different uses and restaurant concepts. List of Chattels and equipment included attached. Very attractive Lease with a new 5 year term that commenced July 1, 2026. Current Rent is approx. $10,312.50/month including TMI plus HST, which is below market rents for the area.

130 Thomas Street Unit 101, Oakville
$350,000
W12807550 MLS
A rare opportunity to own a thriving Oakberry Acai Bowl franchise in the heart of Downtown Oakville! Situated at 327 Lakeshore Rd E, this highly sought-after location is just minutes from Lake Ontario, benefiting from strong foot traffic and a vibrant, health-conscious community.Oakberry is a globally recognized brand specializing in organic, vegan, and gluten-free Acai bowls and smoothies, offering a fast, nutritious alternative with over 30 customizable toppings. With a loyal customer base and growing demand for healthy options, this is the perfect investment in a booming industry.The 1300 sq. ft. space features a modern, inviting setup with optional Patio and a competitive lease of $6,000 per month. BONUS: Includes a basement that can be used for storage or additional workspace, adding extra value to this prime location.Backed by Oakberry's extensive training and marketing support, this location is positioned for continued success.Don't miss this exciting opportunity to own a profitable and growing franchise in one of Oakville's best locations!

327 Lakeshore Road E, Oakville
$199,000
W13479818 MLS
Excellent opportunity to acquire a well-established Halal restaurant in the heart of Downtown Oakville. Approx. 3,500 sq.ft. on two levels with 84 indoor seats plus a 25-seat patio. LLBO licensed. Fully equipped commercial kitchen featuring an 11-ft exhaust hood, walk-in cooler, walk-in freezer and extensive equipment. Turnkey operation with a loyal customer base and strong local reputation. Currently operating limited hours only: Tue-Thu 4pm-10pm and Fri-Sat 1pm-10pm, offering significant growth potential. Gross rent approximately $11,400/month including TMI, HST and water. Approximately 4.5 years remaining on the lease. Suitable for continued Halal cuisine operation or conversion to another restaurant concept, subject to landlord approval. Seller is busy with other business interests and unable to devote sufficient time to this operation.

111 Trafalgar Road, Oakville
$50,000
W13580066 MLS
Lakeshore Trophy Location - High-Profit 3-Bed RMT Clinic. Rare opportunity to own a high-visibility, 553 sq ft boutique clinic on the 2nd floor of a complex building in the 'Core of the Core' Downtown Oakville. Established in 2021 and surrounded by luxury estates, this high-efficiency practice features a direct Lakeshore Rd entrance and a versatile 3-station layout. Key Features: Maximum Spatial Agility: The flexible curtain partition system allows you to instantly reconfigure the treatment area, transitioning between private units and a premium couple's suite at zero cost.Streamlined Operations: Seamless online booking, all major insurance direct-billing portals, and a high-efficiency client management system.The Numbers: Netting $100k+ annually (solo); ongoing full-capacity operation ensures cash flow from Day 1. Massive upside to triple revenue by utilizing all 3 stations.Accessibility: Ample street parking plus adjacent municipal indoor parking with discounted commercial rates.Security: Secure 5-year lease (to 2031) with TMI and private parking included.The Transition: Owner retiring; price includes equipment, 680+ client database, and last month's rent deposit. 1-month hands-on training + optional 3-6 months paid consulting. Vetted professionals only. NDA and Proof of Qualification/Funds required.

297 Lakeshore Road E Unit 6, Oakville
$1
W13544990 MLS
Attn Builders/Investors, Site Plan Approval stage for 6 Story, 16 Boutique Condo Units in The Core of Downtown Oakville. A Unique Plan for 16 Units Ranging From 512-1681 sqft. Prime Location, Steps From The Luxurious Shops, Restaurants Of Lakeshore Rd & Walking Distance To The Oakville Waterfront.

214 Randall Street, Oakville