Eastlake Luxury Homes in Oakville

2054 Lakeshore Road E, Oakville: $39,000,000

Tue, 05 Aug 2025 00:00:00 GMT

Residential Freehold. Listed at $39,000,000. Bedrooms: 7. Bathrooms: 13.0. 2054 Lakeshore Rd. East is one of Oakville's finest lakefront estates.Situated on 1.6 acres & 166 ft of pristine shoreline, complete with deck & stairway access to the water. Designed by renowned architect Gren Weis & brought to life by the exceptional craftsmanship of Coulson Fine Homes.This magnificent 7-bdrm, 13-bath home spans an impressive 19,210 sq ft living space.Step into the grand formal entrance where limestone cast walls create a dramatic first impression serving as a prelude to the extraordinary spaces beyond.The residence showcases 12 ft ceilings on the main level, Brazilian walnut flooring thru-out & custom cabinetry adorns this remarkable home.The estate features an expansive living & dining rm w/breathtaking water views, perfect for intimate gatherings or grand celebrations.Step outside to the covered terrace where you can relax to the sounds of the "Bellagio" inspired fountains & waterfall.The gourmet open-concept kit.flows effortlessly into the fam.rm where water views & fp create a relaxed & comfortable space.The lower-level transforms into an entertainer's paradise, w/a state-of-the-art home theater, gym w/direct access to the infinity edge pool,steam room,golf simulator, wine cellar, billiards area w/rec room & catering kit.A private 2-bdrm nanny suite w/sep. entrance provides additional flexibility.An elevator gives you convenient access to all 5 levels of this thoughtfully designed home.The outdoors offers multiple entertaining areas nestled within the manicured landscaped grounds, the lakefront deck & poolside.The power screened sunroom offers 3 season enjoyment.His & Hers double car garages to accommodate 4 vehicles w/additional parking for 20 more on the circular driveway & auxiliary prkng areas-perfect for hosting memorable events.This waterfront estate represents more than just a home it's a lifestyle statement and every detail is curated to create an environment of uncompromising luxury and comfort. LUXURY CERTIFIED.

2250 Chancery Lane W, Oakville: $8,500,000

Fri, 06 Mar 2026 00:00:00 GMT

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Residential Freehold. Listed at $8,500,000. Bedrooms: 5. Bathrooms: 7.0. Designed to capture panoramic water views - Waterfront luxury awaits at 2250 Chancery Lane W. On exclusive SE Oakville enclave, this modern masterpiece offers 9,177 sf w/5 bdrms & 7 baths. Bright & airy w/ soaring 10ft ceilings on every level & vast windows. Chef's kitchen w/ modern cabinetry, quartz countertops & slab backsplash & top-of-the-line Gaggenau B/I appliances. All living & entertaining spaces are generously proportioned, offer lake vistas & lux finishes such as suspended slab fireplaces, designer lighting & integrated storage to maintain a sleek aesthetic. Multiple walkouts lead to natural stone terrace & infinity pool. MF office. Upstairs - Primary retreat, w/spa-like ensuite & Lake views. 3 add'l bdrms, each w/ensuite, & a laundry rm. Lower Level-Automated theatre, golf simulator, rec/games room w/wet bar; 5th bedroom, exercise room, wine wall, 2 full bathrooms, & walk-up to yard. 3-level elevator, heated tiled floors & full home automation. LUXURY CERTIFIED.

2096 Lakeshore Road E, Oakville: $6,288,000

Thu, 09 Apr 2026 00:00:00 GMT

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Residential Freehold. Listed at $6,288,000. Bedrooms: 7. Bathrooms: 8.0. Tucked behind stately gates and mature trees for exceptional privacy and security, this custom residence sits on just under half an acre and offers a timeless blend of elegant architecture and resort-inspired outdoor living in prime Southeast Oakville. Designed for both entertaining and everyday living with soaring ceilings, oversized windows and refined finishes which create a bright, sophisticated interior. At the heart of the home is a beautifully appointed chef's kitchen with a large centre island, premium appliances, servery and a sun-filled breakfast area overlooking the backyard. Just beyond, the dramatic family room with ceiling height and a wood-burning fireplace creates a warm yet impressive gathering space. A true highlight of the home is the main floor primary suite - a rare and highly sought-after feature. Privately positioned and beautifully scaled, this serene retreat offers a spacious walk-in closet and spa-inspired ensuite, creating an ideal layout for long-term living. Thoughtfully designed mudroom/laundry with separate exterior access, garage entry and private access to the second-floor nanny suite complete the main level. The second level provides exceptional family accommodation with generously sized bedrooms, beautifully appointed bathrooms and a flexible in-law/nanny suite. The expansive lower level features a media room, recreation/games areas, wet bar, wine cellar, gym, additional bedroom and ample storage. Outdoors, the property transforms into a private backyard retreat, complete with mature landscaping, a spectacular in-ground pool, multiple seating and entertaining areas, and a charming, covered cabana/lounge designed for unforgettable summer entertaining. Located moments to the lake, top public and private schools, parks, shopping and commuter routes, this is a rare opportunity to own a gated estate in one of Oakville's most prestigious neighbourhoods.

2055 Lakeshore Road E, Oakville: $5,450,000

Thu, 22 Jan 2026 00:00:00 GMT

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Residential Freehold. Listed at $5,450,000. Bedrooms: 4. Bathrooms: 3.0. Nestled at the end of a private laneway on .996 acre in sought-after South East Oakville, tranquility awaits. This Arts and Crafts-style home, boasting a wrap-around veranda, sits amidst nearly an acre of meticulously manicured gardens, complete with a stunning addition designed by Gren Weis.Step inside this charming 4-bedroom residence, offering over 3600 sqft of living space, and be enveloped in its timeless character.The sun-drenched kitchen is a chefs dream, featuring an AGA stove, step down to the breakfast area with multiple walkouts to the gardens, seamlessly blending indoor and outdoor living. The great room is the perfect place to relax in front of the fire at any time of the day.Entertain with ease in the expansive living and dining room, while a tucked-away main floor office provides privacy.Upstairs, the large principal bedroom overlooks the backyard and gardens, boasting a b/i vanity area, bookcase, custom w/i closet, and a luxurious 3-piece ensuite. Two additional generously sized bedrooms share a timeless 4-piece bath, while the fourth bedroom, currently used as a gym and laundry area, offers flexibility to suit your needs. Outside, is a dining gazebo and stone patio area, complete with a wood f/p, that set the stage for al fresco entertaining amidst the natural beauty of majestic evergreens and perennials.A vegetable garden provides a farm-to-table experience, while a potting shed stands ready to house all your gardening tools. An oversized detached double car garage offers ample storage, with an unfinished coach house space above, roughed in for plumbing and electrical, awaiting your vision to become a work at home office, gym, guest suite, or in-law quarters.Experience the rare tranquility this home brings as you relax in nature,listening to the birds sing on your estate-sized lot. Ideally located steps from the lake, parks, and a short distance to all Downtown Oakville has to offer, including great public and private schools. Luxury Certified.

2322 Bennington Gate, Oakville: $4,699,000

Fri, 10 Apr 2026 00:00:00 GMT

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Residential Freehold. Listed at $4,699,000. Bedrooms: 0. Bathrooms: .0. Welcome to 2232 Bennington Gate-an exceptional opportunity in one of southeast Oakville's most desirable pockets. Tucked discreetly down a private laneway and just one home from the shores of Lake Ontario, this rare offering combines privacy, charm, and proximity to nature.Set on approximately one acre and zoned RL1-0, this remarkable parcel presents the perfect canvas to design and build a custom residence tailored to your vision. Envision a beautifully crafted home surrounded by mature greenery, where peaceful, lakeside living meets timeless comfort.Ideally located for commuters, with convenient access to major highways and just minutes to the Clarkson GO, this address offers both serenity and connectivity. A truly rare chance to create a custom retreat in an exclusive and highly sought-after Oakville neighbourhood.

302 Pinehurst Drive W, Oakville: $4,690,000

Fri, 16 Jan 2026 00:00:00 GMT

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Residential Freehold. Listed at $4,690,000. Bedrooms: 5. Bathrooms: 7.0. Beautiful Custom Built Home In Fabulous Southeast Oakville Location. 4,140 Sq Ft. Very Private And Bright Corner Lot. Spacious Side Centre Hall Plan With Expansive Kitchen, Family Room And Walk-Out To 335 Sq Ft Of Covered Deck. Gas Line On The Deck And Walk Out To Backyard Oasis. Still Room To Add A Pool. Main Floor Has Separate Formal Living Room, Dining Room And Home Office. 24 X 21 Double Garage Will Hold Two Cars Easily. ALL 4 Bedrooms On The Second Floor Have Ensuites. Second Floor Also Has Laundry Room With Side By Side Machines. Lower Level Has 2 Potential Extra Bedrooms, Screening Room, Wet Bar, Wine Cellar, Gym. Winding Streets And Mature Trees Characterize This Prime Eastwood Neighbourhood. Established, Family Community With Excellent Schools. Walk To Maple Grove Public, St. Vincent, Oakville Trafalgar High School & Ej James. QEW And Lakeshore Blvd Equidistant. Trails To The Lake Are Close By.

20 Arkendo Drive, Oakville: $4,298,000

Sun, 01 Mar 2026 00:00:00 GMT

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Residential Freehold. Listed at $4,298,000. Bedrooms: 6. Bathrooms: 5.0. Unobstructed Lake Ontario views define this rare opportunity in South East Oakville's prestigious Arkendo enclave. A truly breathtaking backdrop with a year round promise of spectacular sunrises over the lake and tranquil evenings. The original but meticulously maintained 5 bedroom residence offers 3,122 sq.ft. above grade plus a 1,330sq. ft. finished lower level, presenting an ideal canvas for renewal or renovation.The generous principal rooms all have lakeviews and the functional layout and abundant natural light throughout provide a solid foundation for a new owners vision. Set among luxury homes and close to top schools, downtown Oakville, and major highways and GO transit, this property is perfect for buyers seeking to create their signature lakeview estate in one of Oakville's most exclusive waterfront pockets on a 12,000sqft lot with RL3-0 zoning and 152ft south facing rear gardens and lake views. Some photos are virtually rendered.

24 Birkbank Drive, Oakville: $3,550,000

Thu, 12 Mar 2026 00:00:00 GMT

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Residential Freehold. Listed at $3,550,000. Bedrooms: 4. Bathrooms: 5.0. Warm, serene, and inviting, this English farmhouse-inspired residence sits on an expansive 0.42-acre corner lot, offering a rare blend of character, privacy, and natural beauty. The impressive frontage and side yard create a true estate-like presence, with generous outdoor space on all sides of the home. Inside, a double-height foyer, gleaming hardwood floors, and an airy sense of volume set the tone for the rest of the residence. To one side, an intimate living room provides a refined setting for quiet conversation or reading, while on the other, a substantial main-floor study with rich architectural details is ideal as a home office, library, or music room. Beyond these formal spaces, the home opens into a relaxed, open-concept layout designed for modern living and effortless entertaining. A sunken family room anchors the informal wing and flows into a welcoming dining room highlighted by a wood-burning fireplace that adds warmth and ambiance to gatherings with family and friends. At the heart of the home, the kitchen is bathed in natural light from overhead skylights. Stainless steel appliances, sleek countertops, generous cabinetry, and warm accents create a space that is both highly functional and inviting. Thoughtfully designed with cozy elegance, the home offers four bedrooms, three full bathrooms, and two half bathrooms. Large windows frame views of manicured corner-lot gardens and offer peek-a-boo glimpses of the lake, giving the property a tranquil, retreat-like feel. Outside, beautifully landscaped grounds wrap the home with multiple outdoor zones, including a hot tub, Scandinavian-style sauna, and enclosed swimming pool, creating a resort-like experience in your own backyard. This exceptional property offers convenient access to major highways, lakeside walking trails, and a highly regarded school catchment area, delivering an elevated lifestyle in one of Oakville's most sought-after neighbourhoods.

250 Gatestone Avenue, Oakville: $3,299,900

Mon, 16 Mar 2026 00:00:00 GMT

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Residential Freehold. Listed at $3,299,900. Bedrooms: 5. Bathrooms: 4.0. Welcome to 250 Gatestone Avenue- where every season feels like home! Tucked away on a picturesque tree - lined street, this pride of ownership home is situated in a sought after neighborhood of East Oakville. Sprawling property of 100 x 150 ft lot size is surrounded by mature trees , professionally landscaped complete w/irrigation and shed (2020). This 5 bedroom home has elegant curb appeal and the driveway conveniently accommodates 6 vehicles with an additional double car garage ! Step inside the covered veranda to an oversized foyer featuring a solid wood staircase and lots of natural light from the bay windows showcasing the front gardens. Elegant living room/dining room open concept, carpet free w/custom wood wainscoting. The eat-in kitchen is complete with island, desk area and walk out to a private deck, ideal for entertaining around the outdoor fireplace perfect for your own personal escape. The family room has a cozy wood fireplace w/ walk-out to the backyard deck. The home boasts over 3500 square ft of total liveable space, all five bedrooms on the second level are generous in size and offer comfort and connection for the family . The spacious primary has double door entry , ensuite privileges (renovated 2019) walk in closet and a balcony accommodating lounge chairs and table. The lower level is timeless w/solid wood wet bar and bar fridge and oversized recreation room w/custom wood built-in shelves and custom solid oak wood walls. An additional bathroom , work shop, cedar closet and tons of storage! Excellent schools in the area such as St. Vincents, Oakville Trafalgar Highschool, Maple Grove Public School, St. Mildreds Lightbourne Schools and close proximity to QEW. Follow your Dream, Home.

477 Candler Road, Oakville: $3,220,000

Tue, 14 Apr 2026 00:00:00 GMT

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Residential Freehold. Listed at $3,220,000. Bedrooms: 5. Bathrooms: 6.0. Custom-built home in a highly desirable Southeast Oakville location. Set on an expansive corner lot, this impressive two-storey residence offers over 3,000 sq. ft. of beautifully finished living space-ideal for growing families. A refined transitional design is showcased throughout, beginning with the elegant living and dining rooms just off the welcoming front foyer. The thoughtfully designed chef's kitchen features, stunning two-toned cabinetry, and seamless flow into the spacious family room, complete with a gas fireplace and sliding doors leading to a fully fenced backyard with a covered porch-perfect for entertaining. Upstairs, the bright and airy primary suite boasts large windows, a private balcony, walk-in closet, and a well-appointed ensuite. Three additional generously sized bedrooms offer ample closet space and convenient washroom access. Lower level provides exceptional versatility with a large recreation room, home theatre, gym, fifth bedroom, and an additional washroom. Ideally located within walking distance to Oakville Trafalgar High School, Maple Grove Public School, and a wide range of everyday amenities, this home offers both comfort and convenience in one of Oakville's most sought-after neighbourhoods. Property sold as is.

115 Charnwood Drive, Oakville: $3,199,000

Fri, 31 Oct 2025 00:00:00 GMT

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Residential Freehold. Listed at $3,199,000. Bedrooms: 6. Bathrooms: 5.0. If you have a large family, this home just may be the perfect fit! Completely renovated inside and out, offering an impressive 4,242 sq ft above grade and six spacious bedrooms, an exceptional find in any neighbourhood! Every room is generously sized, even the mudroom, a layout truly designed for family life. The timeless Cape Cod exterior features an oversized double garage and sits on a stunning 16,000+ sq ft lot, fully fenced, ultra private, and ideal for family fun. There's an enormous pool with surrounding deck, plus a covered porch and plenty of green space for play or relaxation. Inside, the main floor sprawls with rich espresso hardwood, two staircases, and fresh paint throughout. The custom kitchen offers hardwood cabinetry, white countertops, a work station, top-tier appliances, a pantry and abundant seating, all anchored by a sun-filled breakfast area that opens to the backyard oasis. The dining room is large enough for any gathering, yet it's the even larger family room that steals the show, with wall-to-wall windows, a fireplace and room for as much seating as you could want. Upstairs, the six bedrooms offer unmatched flexibility: convert one or two into offices, playrooms, or guest suites. The primary retreat includes a vaulted ceiling, large walk-in closet and a hotel-inspired ensuite, your own private escape. The lower level features a full walk-up, home gym, full bath, sauna and an oversized rec room. With immediate occupancy available, you can enjoy summer in this one-of-a-kind home. A true rarity in both space and style.