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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
$2,998,000
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

50 Old Mill Road Unit 503, Oakville
$1,795,000
4 Beds ⋅ 4 Baths ⋅ W13845408 MLS ⋅ Oakridge Heights BLDG.
SPECTACULAR !! "One of a Kind" 2630 Sqft Unit, South/West facing Luxury Condo offering Panoramic RAVINE AND SIXTEEN MILE CREEK Views. 3 Spacious Bedrooms (plus one), 4 Baths, extra large Den with w/o Balcony overlooking Wooded Ravine. Private Sauna, Large Family Room w/Elegant Fireplace and Ravine Views. Two Private Balconies overlook Sixteen mile Creek and Wooded Ravine. A Fabulous location in Old Oakville, offers 2 Parking Spots, Double Size Locker, Walk to 'Go" Train, Shops, Restaurants, Downtown Oakville and Lake. Ideal for Couple downsizing or Family in need of a Nanny suite. Gleaming Hardwood Floors , Crown Molding, Elegant Lighting, in a unique 3 building development with security gate, sitting up on a hill overlooking nature.

50 Old Mill Road Unit 503, 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

221 Robinson Street Unit 211, Oakville
$1,249,000
2 Beds ⋅ 2 Baths ⋅ W13843508 MLS
Welcome to exceptional condominium living in the heart of Old Oakville. Beautifully updated and impeccably presented, this sophisticated 2-bedroom, 2-bathroom residence with two parking spaces and a large private locker offers an extraordinary opportunity to live directly on Oakville's renowned Town Square.Thoughtfully designed with timeless finishes, elegant detailing, and modern comfort, this inviting residence delivers a refined lifestyle in one of Oakville's most coveted and walkable locations. Step outside your door and immerse yourself in the very best of downtownOakville-boutique shopping, acclaimed restaurants and cafés, the lakefront, marina,Oakville Centre for the Performing Arts, library, parks, and scenic waterfront trails are all within easy reach.Enjoy the rare privilege of a true urban village lifestyle, where everyday essentials and exceptional amenities are just steps away. Spend your mornings exploring the waterfront, afternoons strolling through the charming streets of Old Oakville, and evenings dining at some of the area's finest restaurants.For commuters, the location is equally impressive, with convenient access to the GO Station,QEW and Highway 403. Nearby trails along Sixteen Mile Creek and Lake Ontario provide a wonderful connection to nature, creating the perfect balance of sophisticated urban living and outdoor enjoyment. A rare opportunity to experience the very best of Old Oakville- an exceptional address, an enviable lifestyle, and refined condominium living without the multi-million-dollar price tag.

221 Robinson Street Unit 211, 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

50 Old Mill Road Unit 703, Oakville
$999,999
3 Beds ⋅ 2 Baths ⋅ W13830744 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.Offer Remarks

50 Old Mill Road Unit 703, Oakville

236 Randall Street, Oakville
$1,699,000
4 Beds ⋅ 3 Baths ⋅ W13821004 MLS
Location! Location! Stunning Executive freehold townhome in prime downtown Oakville with no monthly maintenance fees! Fabulous low maintenance lifestyle, perfect location just steps to the charming main street with an abundance of upscale stores, fine dining, cafes, steps to theater, lake, harbour, river & fabulous Oakville Club. Built by award-winning DQI (Design Quorum Inc.) Featuring over $150,000 in modern renovations (detailed list of all upgrades 2018-2026 available upon request & attached to listing), beautiful new natural oak hardwood floors, sun filled open concept main floor great room with 10' ceilings & huge picture windows filling the home with natural light, renovated gourmet kitchen with centre island, granite counters & stainless appliances & wine fridge, 4 spacious bdrms, 2.5 renovated baths, freshly painted thruout, modern pot lights thruout, primary bdrm features 18' vaulted ceiling, spa-like ensuite & walkin closet, 4 walkouts to sundecks on main & upper levels, 4th bdrm loft features walk-in closet and walkout to private rooftop terrace, lovely views over 16 Mile Creek, handy 2nd floor laundry ideally situated close to all bdrms, professionally finished basement features spacious family room and large storage room, this beautifully appointed freehold features 2,355 sq.ft. of living space, double car garage with ability to park a 3rd car in front of garage door in lane, primary retreat features vaulted ceilings, spa-like ensuite, walk-in closet, , handy 2nd level laundry, exterior professionally painted in modern upscale colour, This home is the perfect blend of downtown convenience, modern sophistication & low maintenance offering the ultimate lifestyle 10+++

236 Randall Street, Oakville

221 Robinson Street E Unit 204, Oakville
$589,900
1 Beds ⋅ 2 Baths ⋅ W13812960 MLS
Welcome to suite living at 221 Robinson Street. Spanning 750 square feet, this meticulously maintained one-bedroom, one-and-a-half-bathroom residence offers a seamless blend of comfort, style, and boutique low-rise charm. Generous open-concept living and dining area featuring clean lines, bright windows, and an effortless flow designed for both daily living and entertaining. Move-in ready condition with modern flooring, pristine finishes, and a conveniently located partial bath (powder room) for guests in addition to the primary ensuite. Comes complete with 1 owned underground parking space and 1 storage locker. Unbeatably situated in vibrant Downtown Oakville, step outside your door to premier dining, boutique shopping, scenic lakeside parks, and the waterfront trail. Commuters will love the quick access to the Oakville GO Station, QEW, and 403.

221 Robinson Street E Unit 204, Oakville

335 Helen Lawson Lane, Oakville
$3,425,000
3 Beds ⋅ 4 Baths ⋅ W13812244 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

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

305 Church Street, Oakville
$7,000,000
W13793920 MLS
An exceptional opportunity to own a substantial 11,000 sq. ft. four-storey office building in the heart of downtown Oakville. Ideally located within walking distance of Oakville's vibrant downtown, restaurants, cafés, shops and amenities. Featuring high-end executive finishes, the property currently serves as the headquarters of a prestigious financial wealth management firm catering to high-net-worth clients. The sophisticated layout includes multiple private offices, boardrooms, four kitchens, two fireplaces and an outdoor patio. The flexible configuration provides an excellent opportunity for an owner-user, corporate headquarters or multi-tenant investment strategy. A rare downtown Oakville offering combining scale, quality, location and flexibility-ideal for investors or professional users seeking a distinctive commercial property in one of Oakville's most desirable business locations.

305 Church Street, Oakville

153 Balsam Drive, Oakville
$6,575,000
5 Beds ⋅ 5 Baths ⋅ W13779262 MLS
153 Balsam Drive is a sophisticated 4,337 sqft custom residence set on a 50' x 304' park-like lot in one of Oakville's most sought-after settings. Close to Downtown Oakville, top-rated schools, the home pairs craftsmanship with thoughtful functionality. A dramatic double-volume marble foyer with heated flooring and architectural staircase creates an elegant arrival, while custom millwork, designer lighting, oversized windows and premium white oak flooring establish a refined aesthetic throughout. The main level is designed for family living and entertaining, with gracious living and dining spaces flowing into a warm family room with a wood-burning fireplace. A dedicated office overlooks mature greenery. At the heart of the home, the kitchen features a 10' x 4' marble island, face-frame cabinetry, marble surfaces, bespoke lighting and a 60" Lacanche range with a custom plaster hood. A marble-finished pantry and heated natural-stone mudroom add function and elegance. Upstairs, four bedrooms each feature a walk-in closet. The primary suite offers a vaulted ceiling, double skylights with remote blinds, a lounge area and an oversized walk-in closet. The spa-inspired ensuite features heated marble floors, a steam shower with double heated marble seating, custom wainscoting, detailed marble trim and an imported Water Monopoly bathtub. The lower level extends the home's living and entertaining spaces with 10' ceilings and zoned underfloor heating. A fifth bedroom, recreation and games rooms, gym, wine cellar and theatre/flex space offer exceptional versatility for family living and entertaining. A heated three-car garage with car-lift capacity for two additional vehicles, plus exterior snow-melt infrastructure, adds year-round convenience. 153 Balsam Drive is a rare combination of timeless architecture, refined materials, modern functionality and exceptional attention to detail, thoughtfully brought together on one of Oakville's most coveted streets.

153 Balsam Drive, Oakville

372 Trafalgar Road, Oakville
$2,200,000
4 Beds ⋅ 3 Baths ⋅ W13765540 MLS
This rare find in the heart of Old Oakville is a bungalow duplex backing onto scenic 16 Mile Creek, beautifully renovated in 2021 and designed by Kate Zeidler (KZID). Steps from Downtown Oakville, Lake Ontario and the Oakville GO Station, this unique property offers 2 distinct 2-bedroom units - each featuring a separate garage, driveway, private decks with glass railings and breathtaking views. Unit 1 highlights hardwood floors, a gas fireplace in the family room, open-concept living and dining room, kitchen with heated floor, quartz counters & stainless steel appliances, heated floors in the 4pc bath, sunroom and private stairs leading down to the creek dock. Unit 2 offers an open-concept living area with gas fireplace, modern kitchen with breakfast bar, a primary suite with walk-in closet/office space, a 4pc bath with heated floors and ensuite laundry. Both units have independent furnace, A/C and utilities. This legal non-conforming duplex offers strong income potential for dual rental income (currently renting Unit 2 @ $4000/month), multi-generational families or live in one unit while leasing the other. Turnkey waterfront property in a premium location!

372 Trafalgar Road, Oakville

382 Trafalgar Road, Oakville
$3,795,000
4 Beds ⋅ 4 Baths ⋅ W13763614 MLS
Private, elevated, and unlike anything else in Old Oakville - A true four-season outdoor retreat, your private playground for the outdoor enthusiast-where each day invites skating, paddling, kayaking, hiking, fishing, boating and cross-country skiing, alongside wildlife watching and refined al fresco dining, embracing nature in all its seasons. This lofted waterfront residence commands breathtaking views and unmatched privacy along the tranquil 16 Mile Creek. A testament to craftsmanship and design, this waterfront retreat boasts exclusive riparian rights and a private dock, inviting you to embrace the beauty of Oakville's scenic waterways year-round. .A meticulous 2016 renovation elevated this residence with rich hand-scraped oak floors, solid wood doors, custom millwork, and elegant tray ceilings. The sprawling 1,700 sq. ft. premium Wolf PVC deck includes a hot tub oasis, integrated fire table, and motorized awnings, leading to a dock with a kayak launch, swim ladder, and floating dock. Glass-encased staircases on helical piers deliver striking architectural presence and unbroken sight lines to the creek. Inside, sophistication defines every detail. Floor-to-ceiling windows in the living room frame stunning ravine views and dramatic sunsets, while a gas fireplace with a live-edge mantel adds warmth. The chef's kitchen impresses with a leathered Taj Mahal quartzite island, Wolf and Miele appliances, and an integrated Sub-Zero fridge. Heated floors run throughout, including in the spa-like primary ensuite with marble floors, a rain shower, and double vanity. The lower level offers a linear fireplace, built-in bar, and walkout to the deck. A concrete-lined storage room playfully known as the Bomb Shelter provides additional functionality. Blending natural beauty, refined design, and year-round outdoor living, this one-of-a-kind property is just steps to downtown Oakville and the GO Train offering luxury, serenity, and convenience in equal measure.

382 Trafalgar Road, Oakville

60 Old Mill Road Unit PH1, Oakville
$1,379,000
3 Beds ⋅ 3 Baths ⋅ W13754726 MLS
Penthouse perfection with breathtaking views of Lake Ontario and the Toronto skyline. Welcome to Oakridge Heights, one of Oakville's most prestigious addresses. This beautifully renovated 1,984 sq. ft. penthouse offers three bedrooms, 2.5 bathrooms and an additional 486 sq. ft. of outdoor living space on a private wraparound balcony. Natural light fills the open concept layout, with South facing views over Sixteen Mile Creek toward Lake Ontario and east facing views of the Toronto skyline. Purchased in 2019, the suite was extensively renovated in 2020, with more than $372,000 invested in thoughtful upgrades and improvements. The kitchen and all three bathrooms were completely remodeled by Oakville Kitchen and Bath. Additional upgrades include new flooring, designer lighting, a custom entertainment centre, California Closets throughout, and automated blinds and curtains by Shades of Home. The primary bedroom features new carpeting, two walk-in closets, a built-in safe and a lockable jewelry drawer. The den's custom entertainment centre includes a 65-inch Sony television and Bose sound system, which will remain with the suite. Further improvements include new heat pumps in the den and living room and a new Samsung washing machine. Enjoy two side-by-side parking spaces conveniently located near the elevator, two storage lockers and easy access to the Oakville GO station and highways. Downtown Oakville is approximately a 15-minute walk away, with Whole Foods and other gourmet shopping just minutes from your door. Beautifully finished, exceptionally spacious and completely turnkey this is penthouse living at its finest.

60 Old Mill Road Unit PH1, Oakville

60 OLD MILL Road Unit 702, Oakville
$999,000
2 Beds ⋅ 2 Baths ⋅ W13747184 MLS
Experience timeless elegance in this rare, executive corner unit condo located in Oakville's prestigious Old Mill Community. Thisexpansive 1436 sqft residence offers a perfect blend of sophisticated design and natural beauty, featuring panoramic picturewindows that capture breathtaking unobstructed views of 16 mile creek, offering complete privacy and tranquility. Thesun-drenched living space boasts exquisite finishes, 9' ceilings, hardwood floors throughout, a chef-inspired kitchen with warmwood cabinetry, quartz counters, 4 new high end appliances (2026), a pantry closet, and a reading nook or dining area withwalk-out to a private balcony for watching the seasons change over the water. Other features include 2 spacious bedrooms withoversized closets with custom built-ins, 2 luxurious bathrooms, a Paris inspired laundry room, loads of storage space, andtandem two car parking directly beside the building entrance. Building amenities include a freshly renovated lobby, outdoorpergola and seating, pool, gym and sauna. Situated just steps from Whole Foods, historic Downtown Oakville, fine dining,boutique shopping, and the Go Station, this property offers an unparalleled lifestyle of convenience and luxury.

60 OLD MILL Road Unit 702, Oakville

344 Maple Avenue, Oakville
$1,750,000
3 Beds ⋅ 2 Baths ⋅ W13740174 MLS
Welcome to 344 Maple Avenue, an excellent example of an Old Oakville Craftsman-style bungalow on a huge lot. From the moment you arrive, you'll know you've found something special - starting with the welcoming front porch, the perfect spot to enjoy your morning coffee. This deceptively spacious 3-bedroom home features impressively large living and dining spaces, great for entertaining family and friends. It is flooded with natural light from its multiple large windows and glazed doors, yet it maintains a cozy ambiance with its wood-burning fireplace, hardwood floors throughout, and custom built-in cabinetry. The character-filled kitchen offers a highly functional layout and the bright breakfast nook enjoys views of the spectacular yard. The home is situated on an expansive 178 x 57 ft lot featuring beautifully landscaped grounds with mature trees and shrubs, perennial gardens, manicured lawns (with full sprinkler system), and multiple garden rooms, including a secluded courtyard for afternoon tea, and a private patio for evening cocktails. The oversized double-car garage is a huge bonus and a rare find in this area. This highly desirable enclave of quiet, tree-lined streets is just a short stroll from the shops of Olde Oakville Plaza, the Oakville Trafalgar Recreation Centre, Oakville GO, and everything downtown Oakville has to offer - including the harbour, lakeside parks and trails, casual and fine dining, shopping, the library, and the arts centre. The property also offers easy highway access and is within walking distance of top-tier public and private schools. This is a great opportunity to get into Old Oakville and it offers lots of options - move in and enjoy, add on and renovate to your taste, or build a new dream home on one of the largest lots in the neighbourhood. Zoning allows 25% lot coverage on this c.10,000 sq ft lot. The pictures and floor plans alone don't do this unique property justice. Book your visit to see it in person today!

344 Maple Avenue, Oakville

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