1013 - OO Old Oakville Real Estate for Sale

41 Listings
336 Maple Avenue, Oakville
3
BEDS
3
BATHS
$2,188,000
FOR SALE
Welcome to this charming family home in desirable Old Oakville, ideally located near Oakville GO Station, downtown Oakville, Highway 403, the QEW and the lake. Warm oak hardwood flooring and inviting living spaces create a comfortable setting for everyday living and entertaining. The open-concept living and dining areas feature a fireplace and double French doors with a walkout to the outdoors. The renovated kitchen offers granite countertops, high-end appliances, including a new dishwasher, microwave and refrigerator, and a cozy breakfast nook with custom built-in bench seating. A character-filled family room features a second fireplace, custom built-in bookshelves and decorative wood accent beams, with convenient access to the mudroom, two-piece bathroom and wooden deck. The primary bedroom offers a dedicated study area, walk-in closet and three-piece ensuite with marble tile flooring and a shower. Two additional bedrooms, each with double closets, share another three-piece bathroom. The private backyard is designed for relaxation and entertaining, featuring an in-ground swimming pool with a new heater, new filter and robotic pool cleaner. Beautiful gardens with an irrigation system surround the outdoor space, while a built-in BBQ, new hot tub and built-in fire pit create the perfect setting for summer gatherings. The full basement is partially finished and includes an additional bedroom. Additional features include a new furnace and air-conditioning system, new washer and dryer, whole-house water softening system and central vacuum. An inviting family home offering comfortable indoor living and exceptional outdoor entertaining, all in a sought-after Old Oakville location.
426 Trafalgar Road, Oakville
4
BEDS
6
BATHS
$3,949,000
FOR SALE
A private retreat in the heart of South East Oakville, with the city at your doorstep. Driving south on Trafalgar Road, this expansive Tudor is one of the first homes to welcome you into SE Oakville. What makes this residence special is what happens beyond its distinguished facade. Step into the backyard & the world changes: mature trees, ravine, 16 Mile Creek & complete privacy create a setting wonderfully removed from the city. Enjoy morning coffee overlooking the creek, dinner in the outdoor kitchen, evenings around the fire pit, or simply relax beneath the trees & enjoy the wildlife & changing seasons. With riparian rights, professionally landscaped gardens, perennial beds, flowering trees, hedges, timber deck, pergola, gazebo, Napoleon & Lynx outdoor kitchen, the backyard feels like a private escape. Inside, this beautifully maintained Tudor offers 3,000+ sqft. 4 bedrooms, 6 bathrooms. Exceptional craftsmanship includes Jatoba hardwood, handmade plaster crown moulding, 8-inch baseboards, Ciot tile, Hansgrohe fixtures & triple-pane windows. The renovated kitchen features custom cabinetry, premium granite & Viking, Wolf & Miele appliances, while the breakfast & family rooms capture spectacular ravine views. The primary suite is a private retreat with three skylights, unobstructed views of the16 Mile Creek, a private balcony & a custom dressing room. The spa-inspired ensuite features a Neptune air-jetted tub & glass shower. Improvements include updated kitchen finishes & flooring, custom fireplace cabinetry, extensive pot & art lighting, new owned furnace, AC & hot water tank, 200-amp service, wine cellar, irrigation, security & smart-controlled systems. Location is exceptional: approximately a 3-minute walk to Oakville GO, under 5 minutes to Downtown Oakville & Lakeshore, & walking distance to groceries, restaurants & shops. QEW, 407 & 410 access is minutes away. Enjoy the peace & privacy of nature while remaining effortlessly connected.
335 Helen Lawson Lane, Oakville
3
BEDS
4
BATHS
$3,199,000
FOR SALE
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
286 Watson Avenue, Oakville
3
BEDS
4
BATHS
$2,950,000
FOR SALE
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.
129 Watson Avenue, Oakville
3+1
BEDS
5
BATHS
$4,350,000
FOR SALE
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!
533 Carson Lane, Oakville
5+1
BEDS
7
BATHS
$5,950,000
FOR SALE
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.
121 Lakeshore Road 5, Oakville
3
BEDS
4
BATHS
$1,549,900
FOR SALE
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.
287 Macdonald Road, Oakville
4
BEDS
5
BATHS
$3,769,000
FOR SALE
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
343 Douglas Avenue, Oakville
4+1
BEDS
6
BATHS
$1,999,999
FOR SALE
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.
305 Randall Street, Oakville
2+1
BEDS
4
BATHS
$2,499,900
FOR SALE
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!
54 Raymar Place, Oakville
3+2
BEDS
5
BATHS
$6,500,000
FOR SALE
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.
146 Reynolds Street, Oakville
2+1
BEDS
4
BATHS
$2,598,000
FOR SALE
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.
60 Old Mill Road 409, Oakville
2
BEDS
2
BATHS
$599,900
FOR SALE
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.
221 Robinson Street 307, Oakville
2
BEDS
2
BATHS
$798,000
FOR SALE
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.
25 Howard Avenue, Oakville
3+2
BEDS
2
BATHS
$2,799,999
FOR SALE
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.
50 Old Mill Road 503, Oakville
3+1
BEDS
4
BATHS
$1,795,000
FOR SALE
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.
221 Robinson Street 211, Oakville
2
BEDS
2
BATHS
$1,249,000
FOR SALE
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.
374 Spruce Street, Oakville
3+1
BEDS
4
BATHS
$1,899,000
FOR SALE
**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.**
50 Old Mill Road 703, Oakville
2+1
BEDS
2
BATHS
$999,999
FOR SALE
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
236 Randall Street, Oakville
4
BEDS
3
BATHS
$1,670,000
FOR SALE
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+++
221 Robinson Street 204, Oakville
1
BEDS
2
BATHS
$589,900
FOR SALE
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.
74 Howard Avenue, Oakville
4+1
BEDS
4
BATHS
$4,998,000
FOR SALE
DEVELOP, RENOVATE, OR REBUILD IN ORCHARD BEACH, OLD OAKVILLE. Welcome to 74 Howard Avenue, where premium, large-lot offerings are exceptionally rare. This home sits on a truly spectacular 100'x168' lot in Orchard Beach, situated south of Lakeshore Road in highly coveted Old Oakville. This unique property offers ultimate flexibility-enjoy the charming existing home as-is, renovate to suit your taste, or completely redevelop. RL3-0 zoning allows for maximum lot coverage, and the property comes complete with existing, transferable permits in place to sever the lot and build two separate homes.This approved severance is based on a conceptual design by renowned architect John Willmott, envisioning two distinct up to 3,331 sq ft, 4+1-bedroom residences, each featuring spacious two-car garages.Framed by a storybook white picket fence on a quiet avenue just two blocks long, Howard Avenue is one of only a handful of streets in Oakville offering unobstructed views of Lake Ontario.Cherished by the same family for 30 yrs, this property boasts stunning perennial gardens and a coveted southwest exposure that bathes the home in golden-hour light.The current 4+1 bedroom residence includes two seamlessly integrated additions.The first addition features a spacious kitchen, private office, and a principal suite with a gas fireplace.The second is a vaulted, light-filled family room with an additional gas fireplace.Built for entertaining, the main floor also offers a formal dining room & an enchanting living room with an original wood-burning fireplace.A detached, oversized double garage/coach house includes a heated loft, perfect for a private home office or premium storage space. The mature, tree-lined lot perimeter provides rare privacy.Enjoy lakeside morning walks & long, sun-filled evenings just a short stroll from downtown Oakville's boutique shopping, fine dining, top-rated schools & major highways. Secure your legacy in one of the GTAs most prestigious settings. Luxury Certified
372 Trafalgar Road, Oakville
4
BEDS
3
BATHS
$2,200,000
FOR SALE
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!
382 Trafalgar Road, Oakville
2+2
BEDS
4
BATHS
$3,795,000
FOR SALE
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.
60 Old Mill Road Ph1, Oakville
2+1
BEDS
3
BATHS
$1,379,000
FOR SALE
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 702, Oakville
2
BEDS
2
BATHS
$999,000
FOR SALE
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.
344 Maple Avenue, Oakville
3
BEDS
2
BATHS
$1,750,000
FOR SALE
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!
380 Watson Avenue, Oakville
3+1
BEDS
3
BATHS
$2,599,000
FOR SALE
Welcome to this exceptional two-storey family residence nestled on one of South East Oakville's most desirable, tree-lined streets. Combining traditional charm with an ideal functional layout. There are generous spaces for entertaining and everyday family life. Step into the inviting living room, featuring a cozy fireplace and elegant California shutters that fill the space with warm, natural light. The updated eat-in kitchen serves as the heart of the home, complete with built-in appliances, ample cabinetry, and a spacious eat in area. For formal gatherings, the spacious dedicated dining room easily accommodates large family dinners and holiday celebrations. The dramatic main-floor family room steals the show with its soaring vaulted ceilings, second fireplace, and expansive windows. Slide open the doors to step directly onto the private back deck, overlooking a beautifully landscaped, west-facing rear garden-the ultimate setting for enjoying golden-hour sunsets, outdoor dining, and summer entertaining. Conveniently located on the main level, the spacious primary bedroom serves as a peaceful retreat, complete with a private 4-piece ensuite bath. Upstairs, you will find two additional bright bedrooms, fantastic storage solutions, and a second full 4-piece bathroom, making it ideal for kids, guests, or a dedicated home office. The fully finished basement significantly extends your living space, offering endless possibilities for a media room, play area, or home gym, along with a third 4-piece bathroom for added convenience.Located in a premier school district close to top-rated public and private schools, downtown Oakville's boutique shopping and dining, parks, and the lakefront, this South East Oakville gem perfectly blends main-floor comfort with long-term versatility. A rare opportunity on a prime street!
200 William Street, Oakville
5
BEDS
3
BATHS
$2,999,000
FOR SALE
Well positioned property in historic Old Oakville, south of Lakeshore, just steps to the beach, Oakville harbour and Town Square. Sitting proudly up on a rise, this 2 1/2 storey home features wonderful views, light and plenty of space to create your dream home. With lot dimensions of 105' x 105' this full-sized 11,044 SF lot is exactly twice the size of adjacent properties. Savvy buyers may investigate opportunities to sever the lot or explore the creation of an accessory dwelling unit on the property. Zoning RL3, Special Provision 11. The existing home sits entirely on one half of the property in the northeast corner leaving the south and the west portions of the lot open to potential. The existing residence features high ceilings, a grand staircase, formal living room with wood burning fireplace and adjacent sunroom. Lovely southeast dining room takes in all the sunlight. The kitchen and back entrance are in the southwest corner of the main floor. The second floor features 4 bedrooms and one main bathroom. The third floor with two large rooms used as the Primary suite features wonderful views over the garden, the lake, church tower and the beautiful trees of Old Oakville.
15 Chartwell Road, Oakville
4+1
BEDS
6
BATHS
$9,995,000
FOR SALE
15 Chartwell Rd offers a lifestyle of unparalleled luxury. Drive through the gates & discover the grandeur of this palatial estate. South of Lakeshore,1 door from the lake on a HALF ACRE LOT. Painstakingly curated, the contemporary limestone masterpiece you've been waiting for. Solid iron doors lead to a grand foyer revealing the opulent book matched marble floors. Floor to ceiling wdws & French doors flood the house with light. Cascading waterfalls fank the hall.The Dining Room has statement lighting & servery making hosting a breeze. Soaring 18-ft ceilings & a grand gas f/p are focal points of the Great Room,w/captivating views of the resort style yard. Experience culinary excellence in the black lacquer& glass kitchen by NEFF that features top of the line appliances & a B/I coffee machine & butlers pantry. The intimate Living Room with f/p is the ideal retreat. A main floor office w/built-in cabinetry.2 powder & 2 laundry rooms. The backyard oasis has a gunite pool, waterfalls, fire bowls, covered terrace & outdoor kitchen & f/p.The pool house has a change room,3-pc bath & servery. Towering trees surround the home & are positioned to create privacy. A stone driveway,circular fountain & lush gardens create a breathtaking landscape.Floating marble stairs divide the 3 levels of this home or, you can take the elevator. Skylights make the upstairs airy & bright.The principal suite has nearly 13-ft ceilings, an exquisite 6-piece ensuite & 2 W/I closets. A private balcony overlooks the yard.3 add'l bdrms have 10-ft ceilings,private ensuites & W/I closets. The LL caters to all family members. A 5th bdrm/ensuite makes an ideal guest suite.Gym,R/I Golf Simulator,home theatre,Wine Cellar& doggie Spa. The Games & Rec Rooms have a 2nd kitchen & W/O.Heated garage,baths &LL flrs.Automation. Designed by Bill Hicks & features the artistic creativity of the KT Design Group. Located on Oakville's Street of Dreams, this is an iconic living space designed to impress! LUXURY CERTIFIED
46 Second Street, Oakville
4+1
BEDS
7
BATHS
$7,599,000
FOR SALE
Walk to downtown Oakville from this 2024 custom-built residence, just three houses from Lake Ontario on a 65' x 158' lot south of Lakeshore. A rare new-construction opportunity in Old Oakville's most walkable pocket-minutes from the harbour, the Oakville Club, Lakeshore Road dining, and waterfront trails. Offers 4,362 sq. ft. above grade plus a 2,468 sq. ft. finished lower level (6,830 sq. ft. total). Net Zero Ready with a Tarion warranty, crafted by Chatsworth Fine Homes alongside architect John Willmott and designer Jane Lockhart. Main floor features herringbone white oak floors, panel mouldings, a private office, custom mudroom, and a formal dining room. The chef's kitchen boasts Miele appliances (plumbed coffee system, dual steam/standard ovens), SubZero refrigeration, and a wine column. It opens to a great room with a linear fireplace, custom built-ins, and floor-to-ceiling garden views. The primary suite serves as a spa-inspired retreat with a freestanding tub, oversized shower, double vanity, and a dressing-island walk-in closet. Secondary bedrooms each feature private ensuites. Includes heated floors, curbless showers, and upper-level laundry with two washer/dryer sets. The lower level (10' ceilings) is built to entertain: rec room with custom bar/kitchenette, gym, theatre, full bath, additional bedroom, and walk-up access to the yard. The west-facing rear yard catches optimal afternoon sun, complete with a covered heated lounge, in-ground pool with waterfall, and a hot tub. Extras include partial lake views, a heated driveway, radiant floor heating, Crestron automation, Tesla charger rough-in, and a standby generator. A turn-key luxury home in prime Old Oakville where inventory like this rarely comes to market. LUXURY CERTIFIED.
300 Randall Road Ph5, Oakville
2
BEDS
3
BATHS
$2,999,900
FOR SALE
Experience an exceptional standard of luxury in this rare penthouse at The Randall Residences, Oakville's most prestigious boutique condominium. Reserved exclusively for the penthouse level, soaring 12-foot ceilings, exquisite custom millwork, and refined finishes create an atmosphere of timeless elegance. A grand circular stone floor foyer welcomes you into this beautifully designed residence, complete with a spacious front hall closet, powder room, and an generous walk-in laundry room with laundry sink. The spectacular open-concept kitchen is the heart of the home, featuring a generous centre island, marble countertops, premium appliances, and seamless flow into the dining area with custom built-in pantry cabinetry. The living room is framed by floor-to-ceiling wraparound windows that flood the space with natural light, while custom built-ins and a striking fireplace provide warmth and sophistication. Step onto the private south-facing balcony to enjoy sunny views and effortless indoor-outdoor living. The luxurious primary retreat offers a beautifully appointed dressing room and a spa-inspired five-piece marble ensuite. The second bedroom is equally impressive with floor-to-ceiling south-facing windows, a generous closet, and its own private three-piece ensuite. With only 32 exclusive residences, The Randall offers unparalleled privacy and service, including 24-hour concierge, three elevator banks, impeccably maintained underground parking with soaring ceilings, two premium parking spaces, and a private locker. Perfectly situated in the heart of downtown Oakville, you're just steps from the lake, boutique shopping, cafés, fine dining, and the renowned Sotto Sotto restaurant located on the main floor. A truly exceptional opportunity to own one of downtown Oakville's most distinguished penthouse residences.
185 Robinson Street 202, Oakville
2
BEDS
2
BATHS
$699,900
FOR SALE
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!
488 Macdonald Road, Oakville
4
BEDS
5
BATHS
$4,999,000
FOR SALE
Grand Grounds. Timeless Elegance. Extraordinary Potential.An exceptional opportunity in one of Olde Oakville's most prestigious neighbourhoods. Tucked behind private gates and nestled beneath a magnificent canopy of mature trees, this beautifully landscaped and increasingly rare 0.82-acre estate offers over 7,100 square feet of living space in an irreplaceable setting just moments from Downtown Oakville.Approached by a sweeping circular drive, the timeless brick residence immediately impresses with its classic Colonial Williamsburg-inspired architecture, elegant symmetry, and commanding presence. Beyond the front entrance, peaceful views of the private pond and lush landscape create a tranquil, park-like retreat rarely found in such a coveted urban location.Custom built in 1980, this stately four-bedroom residence offers an extraordinary opportunity to reimagine an exceptional property. Offered in "as is" condition, the home presents the perfect canvas for those looking to undertake a significant renovation, thoughtfully restore its timeless character, or explore the opportunity to create a magnificent custom estate (subject to all necessary approvals). Whether preserving its enduring architectural charm or designing an entirely new vision, the possibilities are truly exceptional.The expansive grounds provide an incredible backdrop for family living, entertaining, and creating lasting memories for generations to come. Properties offering this rare combination of land, privacy, scale, and location are becoming increasingly difficult to find.Ideally situated within one of Oakville's most sought-after school districts and just a short walk to Downtown Oakville, the Oakville GO Station, public and private schools, Post Park, Whole Foods, Longo's, boutique shopping, restaurants, and the lakefront, this is more than an exceptional property-it is a rare opportunity to create a legacy estate in one of Olde Oakville's most coveted locations.
300 Randall Street Ph1, Oakville
3
BEDS
4
BATHS
$5,999,900
FOR SALE
RESTORATION HARDWARE SHOW SUITE: Welcome to the crown jewel of The Randall Residences, Oakville's most prestigious address. This sun-filled Signature Penthouse Suite is the largest residence inside and out, offering approximately 3,337 sq. ft. of sophisticated living plus a 386 sq. ft. second-storey lounge with skylight and an expansive 1,327 sq. ft. southeast-facing terrace. Enter through a grand rotunda foyer with marble floors and an impressive RH chandelier, setting the tone for this exceptional home. The open-concept living and dining areas boast 12-foot ceilings, floor-to-ceiling wrap-around windows, custom Downsview cabinetry, top-of-the-line appliances, and a gas fireplace - an entertainer's dream. Restoration Hardware fixtures illuminate throughout the suite exuding an atmosphere of sophisticated refinement. The principal bedroom retreat is a haven of tranquility with a custom zebra-wood dressing room and a spa-inspired 6-piece ensuite, complete with heated marble floors, polished nickel fixtures, and a freestanding soaking tub. Two additional bedrooms each feature their own private ensuites for ultimate comfort and privacy. Ascend to the second-storey lounge, ideal for a home gym, office, or serene retreat, and step out to your private rooftop terrace designed for entertaining, featuring multiple lounging and dining zones with a gas BBQ hookup. Additional luxuries include a Crestron home automation system, integrated entertainment features, 3 parking spaces, and 2 storage lockers. Residents enjoy 24-hour concierge service in this award-winning Rosehaven Homes development, celebrated for its impeccable craftsmanship and timeless elegance. Sotto Sotto on the ground floor. Located steps from Lake Ontario, fine dining, boutique shopping, and just minutes to major highways, this penthouse represents the pinnacle of luxury living in Oakville. If you demand the best, look no further. Luxury Certified. Listed US$4,255,000
253 Church Street 402, Oakville
2
BEDS
3
BATHS
$2,999,999
FOR SALE
Welcome to The Coventry Penthouse-one of downtown Oakville's most distinguished luxury residences. This architecturally significant suite, designed by acclaimed architect Bill Hicks, offers an unparalleled lifestyle just steps from the lake, waterfront parks, shopping, and dining. Occupying a premier position within this exclusive boutique building, the penthouse delivers exceptional privacy and sophistication. Expansive living spaces are highlighted by soaring ceilings, a dramatic skylight, custom Downsview kitchen, walk-in pantry, formal dining room, integrated Sonos sound system, and elegant indoor-outdoor living. Two sets of French doors open to a covered terrace featuring a striking two-sided fireplace, while a spectacular private rooftop terrace creates the perfect setting for entertaining and relaxation. The luxurious primary retreat includes terrace access, a spacious walk-in closet, and spa-inspired five-piece ensuite. Complete with a second bedroom, den (den can be converted to a third bedroom), 2.5 bathrooms, two premium parking spaces, and a locker, this exceptional residence offers the comfort of a custom home with the ease and convenience of luxury condominium living. A rare opportunity to own a truly unique penthouse in the heart of downtown Oakville. *Some photos may be virtually staged
350 King Street, Oakville
3+2
BEDS
5
BATHS
$10,900,000
FOR SALE
Nestled in the heart of downtown Oakville, this magnificent historical home offers unparalleled charm and elegance, combined with modern amenities. Spanning over 8,000 square feet, the expansive layout provides both grandeur and comfort, perfect for family living or entertaining on a grand scale. With stunning views of the sparkling waters of Lake Ontario, every room is designed to maximize the beauty of its lakeside setting. The home boasts high ceilings, intricate architectural details and walnut hardwood floors, blending timeless craftsmanship with contemporary design. The private lush yard with 104 feet of frontage is a rare gem, providing a serene outdoor oasis with mature trees and ample space for outdoor activities or quiet relaxation and complete privacy. Whether you're enjoying a morning coffee while gazing at the lake or hosting a summer gathering, the outdoor space is as inviting as the interiors. The property's prime location puts you just steps from Oakville's charming downtown, offering convenient access to world-class dining, shopping, and cultural attractions, while still providing the tranquility of lakeside living. With its rich history, extraordinary space, and unbeatable location, this is a once-in-a-lifetime opportunity to own a piece of Oakville's heritage.
338 Macdonald Road, Oakville
4
BEDS
4
BATHS
$3,790,000
FOR SALE
Nestled in an immensely desired mature pocket of Old Oakville, this exclusive Fernbrook development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. A selection of distinct detached single family models, each magnificently crafted with varying elevations, with spacious layouts, heightened ceilings and thoughtful distinctions between entertaining and principal gathering spaces. A true exhibit of flawless design and impeccable taste. Impressive detached w/47-foot frontage, 2836 sqft of finished space w/an additional 1,000+ sqft(approx) in the lower level left untouched. Curated:4 beds + 3.5 baths. Utility wing from garage, chef's kitchen w/w/in pantry, expansive breakfast+great room. Quality finishes are evident; with 11' ceilings on the main, 9' on the upper & lower levels and large glazing throughout, including 12-foot glass sliders to the rear terrace from great room. Quality millwork w/solid poplar interior doors/trim, plaster crown moulding, oak flooring & porcelain tiling. Customize stone for kitchen & baths, gas fireplace, central vacuum, recessed LED pot lights & smart home wiring. Downsview kitchen w/walk-in pantry, top appliances, dedicated breakfast + expansive glazing. Primary retreat impresses w/2 walk-ins + hotel-worthy bath. Bedroom 2 & 3 share ensuite & 4th bedroom enjoys a lavish ensuite. Convenient upper level laundry. No detail or comfort will be overlooked, w/high efficiency HVAC, low flow Toto lavatories, high R-value insulation, including fully drywalled, primed & gas proofed garage interiors. Refined interior with clever layout and expansive rear yard offering a sophisticated escape for relaxation or entertainment.
321 Helen Lawson Lane, Oakville
3
BEDS
5
BATHS
$3,195,000
FOR SALE
Nestled in an immensely desired mature pocket of Old Oakville, this exclusive Fernbrook development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. A selection of distinct models, each magnificently crafted, with spacious layouts, heightened ceilings and thoughtful distinctions between entertaining and contemporary gathering spaces. A true exhibit of flawless design and impeccable taste. The Arlington; 3,677 sqft of finished space, 3 beds, 3 full baths + 2 half baths, this model includes 622 FIN sqft in the LL. A few optional layouts ground + upper. Garage w/interior access to mudroom, ground floor laundry, walk-in closet, full bath + family room w/French door to rear yard. A private elevator services all levels. Quality finishes are evident; with 10 ceilings on the main, 9 on the ground & upper levels. Large glazing throughout, glass sliders to both rear terraces & front terrace. Quality millwork & flooring choices. Customize stone for kitchen & baths, gas fireplace, central vacuum, recessed LED pot lights & smart home wiring. Chefs kitchen w/top appliances, dedicated breakfast, overlooking great room. Primary retreat impresses with large dressing, private terrace & spa bath. No detail or comfort will be overlooked, with high efficiency HVAC, low flow Toto lavatories, high R-value insulation, including fully drywalled, primed & gas proofed garage interiors. Expansive outdoor spaces; three terraces & a full rear yard. Perfectly positioned within a canopy of century old trees, a stones throw to the state-of-the-art Oakville Trafalgar Community Centre and a short walk to Oakvilles downtown core, harbour and lakeside parks. This is a landmark exclusive development in one of Canadas most exclusive communities. Only a handful of townhomes left. Full Tarion warranty. Occupation estimated summer 2026.
Lot 101 Douglas Avenue, Oakville
4
BEDS
4
BATHS
$4,290,000
FOR SALE
Nestled in an immensely desired mature pocket of Old Oakville, this exclusive Fernbrook development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. The Douglas Collection is an extension of the inaugural development with an exclusive collection of seven homes located on Douglas Avenue. Distinct detached single family models, each magnificently crafted with varying elevations, with spacious layouts, heightened ceilings and thoughtful distinctions between entertaining and principal gathering spaces. A true exhibit of flawless design and impeccable taste. "The Chatsworth"; detached home with 48-foot frontage, between 3,188-3,204sf finished space w/an additional 1,000+sf (approx)in the lower level & 4beds & 3.5 baths. Utility wing from garage, chef's kitchen w/w/in pantry+ generous breakfast, expansive great room overlooking LL walk-up. Quality finishes are evident; with 11' ceilings on the main, 9' on the upper & lower levels and large glazing throughout, including 12-foot glass sliders to the rear terrace from great room. Quality millwork w/solid poplar interior doors/trim, plaster crown moulding, oak flooring & porcelain tiling. Customize stone for kitchen & baths, gas fireplace, central vacuum, recessed LED pot lights & smart home wiring. Downsview kitchen w/walk-in pantry, top appliances, dedicated breakfast + expansive glazing. Primary retreat impresses w/2 walk-ins + hotel-worthy bath. Bedroom 2 & 3 share ensuite & 4th bedroom enjoys a lavish ensuite. Convenient upper level laundry. No detail or comfort will be overlooked, w/high efficiency HVAC, low flow Toto lavatories, high R-value insulation, including fully drywalled, primed & gas proofed garage interiors. Refined interior with clever layout and expansive rear yard offering a sophisticated escape for relaxation or entertainment.
53 Thomas Street, Oakville
4
BEDS
3
BATHS
$3,250,000
FOR SALE
Nestled south of Lakeshore in the heart of Old Oakvilles historic district, this beautifully restored Georgian-style home, designed by Gren Weis, blends timeless character with modern updates. Steps from the lake, river, and vibrant Downtown, it offers an unmatched lifestyle location.The home boasts exceptional curb appeal with a flagstone path leading to a spacious foyer. Sun-filled interiors feature Farrow & Ball paint, new hardwood on the main level, preserved fir upstairs, smooth ceilings, and recessed LED lighting.The updated kitchen includes a large island, built-in appliances, and desk area. The dining room offers panelled walls, RH sconces, French doors to the garden, and plantation shutters. A charming living room features built-in bookcases, window seat, wood-burning fireplace, and walkouts to a sunroom overlooking the southwest garden and pool. A mudroom and stylish powder room complete the main floor.Upstairs are four bedrooms with ample closets and antique brass hardware. The primary suite offers custom built-ins and a renovated ensuite with heated Carrara marble floors and zero-threshold shower.The fully finished lower level (8 ceilings, slate flooring) adds living space with a media room, workout room, cedar closet, laundry, and storage. Updated mechanicals include a high-efficiency furnace, central AC, 100 AMP panel, irrigation. Cedar roof, new fencing, cobblestone driveway. Outside enjoy a private oasis with saltwater inground pool, brick patios, and landscaped gardens. Steps to the Lake, Oakville Club, Yacht Squadron, Library, Performing Arts Centre, Downtown, and top schools.
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