Oakville Luxury Real Estate
Trying to find Luxury Oakville homes for sale? Luxury Oakville Real Estate $2.5 Million Homes.
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390 Seaton Drive in Oakville: 1020 - WO West Single Family Residence for sale (1 - Oakville) : MLS®# 40828660
390 Seaton Drive Oakville L6L 3Y2 
$2,799,000Residential- Status:
- Active
- MLS® Num:
- 40828660
- Bedrooms:
- 5
- Bathrooms:
- 6
- Floor Area:
- 6,357 sq. ft.
An exceptional custom residence set on a commanding 150 x 75 ft lot in one of Southwest Oakville's most established and coveted neighbourhoods.Boasting over 6,300 square feet of total living space, this home offers 5 bedrooms and 6 bathrooms across three beautifully finished levels. This home showcases a rare and highly desirable layout with two primary suites - one on the main floor and a second grand retreat upstairs. Designed for elevated living and effortless entertaining, the home features refined principal rooms including formal living and dining areas, a private office, two powder rooms, and a full laundry suite. At its heart, the chef's kitchen impresses with rich cabinetry, granite countertops, marble flooring, a large centre island with seating, built-in stainless steel double wall ovens, gas cooktop, beverage fridge, and seamless flow into the family room with gas fireplace and custom built-ins. The main-floor primary suite offers privacy, an ensuite bath, and walk-in closet - ideal for multigenerational living or main-level convenience. Upstairs, the second primary retreat feels like a private sanctuary with its own fireplace, spa-inspired ensuite, and generous dressing space. Two additional bedrooms share a spacious 5-piece Jack & Jill bath, creating a functional family wing. The fully finished lower level enhances the lifestyle appeal with a large recreation lounge, wet bar, gym area, fifth bedroom, and full bath - perfect for guests or extended family. Outdoors, a private backyard oasis framed by mature landscaping features an inground pool, pergola-covered lounge, multiple hardscape entertaining areas, and a detached shed. A double garage with upgraded tiled flooring and private driveway complete this distinguished offering. Five bedrooms. Two primary suites. Three finished levels. A rare estate-sized lot in Southwest Oakville. 390 Seaton Drive - a home of scale, versatility, and enduring elegance. More detailsListed by RE/MAX Aboutowne Realty Corp.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
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150 Cairncroft Road in Oakville: 1011 - MO Morrison Single Family Residence for sale (1 - Oakville) : MLS®# 40837779
150 Cairncroft Road Oakville L6J 4L9
$2,799,000Residential- Status:
- Active
- MLS® Num:
- 40837779
- Bedrooms:
- 4
- Bathrooms:
- 3
- Floor Area:
- 3,931 sq. ft.
Welcome to 150 Cairncroft, a rare opportunity to own a distinctive property in one of Oakville's most coveted neighbourhoods. Nestled on a stunning 0.4 acre (17,416 sq ft) corner lot, this charming 3,052 sq ft residence is enveloped by mature trees and lush landscaping, offering the perfect blend of privacy and prestige. Set just steps from the lake and picturesque Gairloch Gardens, the location is unparalleled for those seeking an upscale lifestyle surrounded by nature, yet within easy reach of top-rated schools, downtown Oakville, major commuter routes & transit. Whether you're looking to move right in, renovate, or build your custom dream home (RL1-0 zoning), this property delivers exceptional potential. The existing home is rich in character and warmth with its Mediterranean-inspired façade and design, offering 4 bedrooms + den, and 2.5 bathrooms. The living room showcases exposed structural beams set amongst 1 of this home's 4 cozy fireplaces, lending a rustic allure and architectural interest. While the soaring two-storey foyer also offers captivating views of the inviting yet secluded courtyard-style patio - ideal for entertaining or relaxing under the canopy of greenery. Properties of this caliber and location are exceedingly rare. Don't miss your chance to secure a premium foothold in a neighbourhood known for luxury homes, timeless appeal, and rare public lakefront access only steps away! More detailsListed by RE/MAX Aboutowne Realty Corp.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
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129 Wolfdale Avenue in Oakville: 1017 - SW Southwest Single Family Residence for sale (1 - Oakville) : MLS®# 40839389
129 Wolfdale Avenue Oakville L6L 4R9
$7,470,000Residential- Status:
- Active
- MLS® Num:
- 40839389
- Bedrooms:
- 5
- Bathrooms:
- 7
- Floor Area:
- 6,891 sq. ft.
Welcome to 129 Wolfdale Ave, a custom-designed modern craftsman estate, positioned on a premium lot in Southwest Oakville. With approximately 7,300 sq.ft. of living space, and an incredible 1,700 sq.ft. two level garage that stores 6 cars indoors, serviced by a car elevator. This exceptional home blends refined architecture resort-inspired outdoor living, surrounded by a private, tree-lined backdrop. The portico leads into a breathtaking foyer, setting the stage for the elegant interiors beyond. Considered finishes include coffered ceilings, herringbone marble flooring, and wide-plank oak throughout the principal spaces. A stylish main floor office, complete with bespoke millwork. The great room features 14' ceilings, a custom walnut media wall, and a floor-to-ceiling stone fireplace. This space flows effortlessly into the chef's kitchen, beautifully appointed with a full Thermador fridge and freezer, Gaggenau double ovens, range, steam oven, warming drawer, and quartz countertops. A fully equipped butler's pantry that keeps entertaining effortless. The upper-level hosts four spacious bedrooms, each with private ensuites with heated floors. The primary suite is a true retreat, featuring a private balcony, a spa-inspired five-piece ensuite, and a custom walk-through closet. The finished lower level offers additional living space, including a fifth bedroom, walk-up access to the rear garden, gym and home theatre. All six garage spaces, along with driveway and front walkway are radiant heated, ensuring year-round comfort and no snow buildup. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
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2054 Lakeshore Road E in Oakville: 1006 - FD Ford Single Family Residence for sale (1 - Oakville) : MLS®# 40839819
2054 Lakeshore Road E Oakville L6J 1M3
$33,000,000Residential- Status:
- Active
- MLS® Num:
- 40839819
- Bedrooms:
- 7
- Bathrooms:
- 12
- Floor Area:
- 19,210 sq. ft.
2054 Lakeshore Rd. East is one of Oakville's finest lakefront estates.Situated on 1.6 acres & 164.22 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.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 theatre, 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&Her double car garages to accommodate 4 vehicles w/additional parking for 15 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 where every detail has been carefully curated to create an environment of uncompromising luxury & comfort. LUXURY CERTIFIED. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
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343 Douglas Avenue in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40840927
343 Douglas Avenue Oakville L6J 3S7
$4,265,000Residential- Status:
- Active
- MLS® Num:
- 40840927
- Bedrooms:
- 5
- Bathrooms:
- 6
- Floor Area:
- 3,100 sq. ft.
A rare opportunity to create a new, luxurious custom-home on one of Old Oakville's most coveted streets, set on an exceptionally private, tree-lined lot. This rarely offered design features a double-car garage and a fully finished lower level, thoughtfully crafted to deliver both elegance and functionality. Enjoy the expertise of a dedicated interior designer throughout the entire building process, ensuring every finish and detail is tailored to your vision. Features include: Curated luxury finishes throughout. Personalized interior design consultation and selection services. Optional elevator upgrade available with a three bedroom floorplan. Exceptional craftsmanship by a trusted custom builder with nearly 20 years of experience. An extraordinary opportunity to build a timeless custom home in one of Oakville's most prestigious neighbourhoods. Drawings are approved by Committee of Adjustments. Projected completion date August 2027 /Permit Process Underway. Great opportunity to take advantage of pre- build pricing. More detailsListed by Royal LePage Real Estate Services Phinney Real Estate- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
- Contact by Email
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113 Maple Grove Drive in Oakville: 1006 - FD Ford Single Family Residence for sale (1 - Oakville) : MLS®# 40838815
113 Maple Grove Drive Oakville L6J 4T9
$12,000,000Residential- Status:
- Active
- MLS® Num:
- 40838815
- Bedrooms:
- 6
- Bathrooms:
- 10
- Floor Area:
- 8,548 sq. ft.
Gracefully positioned behind gated entry on an expansive 0.78-acre parcel in South-East Oakville, this distinguished residence offers an exceptional blend of privacy, scale, and refined living. Thoughtfully designed for both grand entertaining and comfortable family living, the home showcases timeless architecture, remarkable craftsmanship, and elegant interiors throughout. A refined material palette features heated marble flooring with decorative inlay and galaxy border, quarter-sawn white oak hardwood flooring, crown moldings with extensive ceiling detailing and custom millwork. Carefully considered architectural details, custom cabinetry, integrated technology, and seamless indoor-outdoor connections create a residence that feels both impressive and effortlessly livable. Surrounded by mature landscaping and resort- style outdoor spaces-including a spectacular ozone pool and cabana setting, covered entertaining areas, and a year-round hot tub-the property offers an exceptional lifestyle just moments from the lake, top schools, and the amenities of downtown Oakville. More detailsListed by Royal LePage Real Estate Services Phinney Real Estate- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
- Contact by Email
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1098 Lakeshore Road W in Oakville: 1017 - SW Southwest Single Family Residence for sale (1 - Oakville) : MLS®# 40842845
1098 Lakeshore Road W Oakville L6L 1E9
$4,499,000Residential- Status:
- Active
- MLS® Num:
- 40842845
- Bedrooms:
- 5
- Bathrooms:
- 5
- Floor Area:
- 6,849 sq. ft.
Set on a rare and private 1/2+ acre estate lot in one of South West Oakville's most coveted lakeside neighbourhoods, this stunning custom designed home offers over 6,500 sq. ft. of luxurious living space just steps from Lake Ontario and within minutes to esteemed Appleby College. Thoughtfully designed for both everyday living and grand-scale entertaining, the home features 10' ceilings on the main level, 9' ceilings on the upper and lower levels, extensive custom millwork, rich hardwood flooring, and exceptional craftsmanship throughout. The Hampton-inspired custom kitchen and butler's pantry serve as the heart of the home, complemented by luxurious ensuite bathrooms and high-end finishes at every turn. The main floor primary retreat offers the convenience of single-level living, complete with a custom walk-in closet, spa-inspired 5-piece ensuite, gas fireplace, and serene backyard views. The fully finished lower level is ideal for multigenerational living, featuring a second kitchen, two additional bedrooms, a gym, wet bar, games area, and expansive recreation room. Step outside to your own private resort, where mature landscaping surrounds a saltwater pool, waterfall feature, and covered outdoor living area. A truly exceptional opportunity to own a custom estate property on one of Oakville's most prestigious streets, surrounded by luxury homes, steps to the lake, and moments to top-ranked schools, parks, and downtown Oakville. Some opportunities are measured in sq footage, others are measured in land, location and the life you'll build there. 1098 Lakeshore Rd is not to be missed. More detailsListed by The Agency- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
- Contact by Email
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153 Cairncroft Road in Oakville: 1011 - MO Morrison Single Family Residence for sale (1 - Oakville) : MLS®# 40844841
153 Cairncroft Road Oakville L6J 4L8
$3,890,000Residential- Status:
- Active
- MLS® Num:
- 40844841
- Bedrooms:
- 4
- Bathrooms:
- 5
- Floor Area:
- 4,367 sq. ft.
Nestled on an exceptional 94' x 141' mature lot in prestigious Southeast Oakville, this beautifully renovated executive residence offers timeless elegance, luxurious finishes, and an unbeatable location within walking distance to top-ranked schools, including OTHS, EJ PS etc. Offering approximately 3487 sqft. above grade plus a finished lower level, this exceptional home features 4 bedrooms, 5 bathrooms, and thoughtfully designed living spaces perfect for both family living and entertaining.Rich wide-plank hardwood floors, crown mouldings, custom millwork, wainscoting, built-ins, pot lights, stone flooring, an impressive oak staircase with iron pickets, and four gas fireplaces showcase the home's exceptional craftsmanship. The stunning renovated chef's kitchen is appointed with premium Miele appliances, custom cabinetry, and overlooks the inviting sunken family room, creating the perfect gathering space. Elegant formal living and dining rooms provide refined spaces for entertaining, with the living room easily accommodating a baby grand piano.The luxurious primary retreat features its own gas fireplace, an expansive dressing room, and a spa-inspired 4-piece ensuite with a glass shower. The finished lower level offers a spacious recreation room, exercise room, 2-piece bath, and abundant storage.Extensive updates include a complete kitchen renovation, premium Miele appliances, exterior LED lighting, renovated garage, repaved driveway, new eavestroughs, freshly painted exterior façade, new pool liner and heater, and numerous quality improvements throughout.The spectacular backyard is a private oasis featuring a sprawling stone patio, covered terrace, and sparkling in-ground pool surrounded by mature landscaping-perfect for summer entertaining. Ideally located just steps to Lake Ontario, Gairloch Gardens, parks, trails, and only a 3-minute drive to downtown Oakville's boutique shops, fine dining, and waterfront. More detailsListed by RE/MAX Hallmark Realty Ltd- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
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104 Whittington Place in Oakville: 1017 - SW Southwest Single Family Residence for sale (1 - Oakville) : MLS®# 40845570
104 Whittington Place Oakville L6K 3V9
$2,599,999Residential- Status:
- Active
- MLS® Num:
- 40845570
- Bedrooms:
- 5
- Bathrooms:
- 4
- Floor Area:
- 5,003 sq. ft.
Perfectly positioned in one of Southwest Oakville's most sought-after neighbourhoods, directly across from the prestigious Appleby College, this exceptional family residence offers over 5,000 square feet across all levels, blending timeless elegance with outstanding functionality. Thoughtfully designed for both everyday living and entertaining, the main level showcases expansive principal rooms filled with natural light. The chef-inspired kitchen is the heart of the home, featuring custom cabinetry, granite countertops, a large centre island, quality appliances, and an adjoining breakfast area overlooking the private backyard. The inviting family room offers beautiful seamless access to the outdoor living spaces, while the formal living and dining rooms provide refined spaces for hosting family gatherings and special occasions. A handsome wood-panelled home office creates the perfect work-from-home environment. Upstairs, the home offers 3 spacious bedrooms, highlighted by a luxurious primary retreat complete with a generous walk-in dressing room and spa-inspired ensuite with heated floors. The additional bedrooms are well-proportioned and ideal for family or guests. The finished lower level extends the living space with 2 additional bedrooms, a large recreation/media room, a custom wine cellar, ample storage, and flexible space perfect for extended family, teenagers, or a home gym. Set on a private, mature lot, the backyard features an in-ground pool, hot tub and exceptional privacy, creating the perfect setting for summer entertaining. Ideally located just moments from the lake, parks, downtown Oakville, and top-rated schools, this is an outstanding opportunity to own a distinguished family home in one of Oakville's most coveted neighbourhoods. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
- Contact by Email
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1102 Crestview Street in Oakville: 1011 - MO Morrison Single Family Residence for sale (1 - Oakville) : MLS®# 40846783
1102 Crestview Street Oakville L6J 2C6
$6,250,000Residential- Status:
- Active
- MLS® Num:
- 40846783
- Bedrooms:
- 5
- Bathrooms:
- 7
- Floor Area:
- 7,139 sq. ft.
This is not your average home-it's a statement.Set on a premium, near half-acre lot, this custom masterpiece brings together the vision of Gren Weis, the craftsmanship of Bachly Construction, and the landscape artistry of Mark Pettes-creating a residence that feels as elevated as it is effortless.From the moment you step inside, the energy shifts. Soaring 10-ft ceilings and a stunning 17-ft sun-drenched family room set the tone-open, airy, and designed to impress. A dedicated main floor office offers the perfect balance of productivity and privacy, ideal for today's work-from-home lifestyle. Whether it's an intimate night in or a full house of guests, the flow is seamless. A prep kitchen keeps everything behind the scenes running smoothly, while the newly added main-floor bar invites you to pour a drink and stay awhile. The glass-encased wine room? Pure drama-in the best way.Every bedroom is its own private retreat, complete with a luxe ensuite-because comfort should never be compromised.Downstairs, the vibe continues. Think late nights at the wet bar, morning workouts in your private gym, spa-level relaxation, and a fully equipped nanny suite. A walk-out lower level leads directly to the hot tub-blurring the line between indoor comfort and outdoor indulgence. This level isn't just extra space, it's a lifestyle.And then there's the backyard. Tiered, curated, and designed to be lived in. A newly added pool sets the scene, while the covered cabana lounge and outdoor kitchen make entertaining feel like a vacation. There's even a dedicated dog run-because every detail has been considered.Sleek, bold, and undeniably fun-this is a home that doesn't just look good, it lives beautifully. More detailsListed by Royal LePage Real Estate Services Phinney Real Estate- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
- Contact by Email
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2458 Meadowood Crescent in Oakville: 1001 - BR Bronte Single Family Residence for sale (1 - Oakville) : MLS®# 40848426
2458 Meadowood Crescent Oakville L6L 1V6
$3,498,000Residential- Status:
- Active
- MLS® Num:
- 40848426
- Bedrooms:
- 4
- Bathrooms:
- 5
- Floor Area:
- 5,684 sq. ft.
Tucked away on a quiet dead-end crescent on one of Bronte's best streets, this custom-built home blends thoughtful design and family-friendly living. It is steps from a park and playground, and within walking distance of Bronte's renowned restaurants, waterfront, and marina.Offering over 3,500 square feet above grade, plus a newly finished basement (2026), every inch has been designed for everyday living and effortless entertaining. A formal foyer creates a beautiful first impression, opening to an elegant living room and private main floor office.The heart of the home is an impressive chef's kitchen with premium appliances, an oversized centre island, and exceptional storage. A butler's pantry seamlessly connects the kitchen to the walk-in pantry and formal dining room. A generous breakfast area flows into the inviting family room, featuring a warm gas fireplace.Designed as an extension of the living space, the professionally landscaped backyard was transformed by ProScape Land Design into a private outdoor retreat. It features a covered dining area with a built-in BBQ, tiered seating beneath a pergola, and a private putting green.Upstairs, the layout offers privacy for everyone. The primary suite is a true retreat with a spa-inspired ensuite and a spacious walk-in closet. Two secondary bedrooms share a beautifully appointed Jack-and-Jill bathroom, while the fourth bedroom enjoys its own private ensuite.The newly completed lower level expands the living space with beautifully finished recreation areas, a custom built-in bar with beverage and wine refrigerators, a wine display, extensive built-in cabinetry, a dedicated home gym, and a convenient two-piece bathroom.From its exceptional custom design and family-friendly layout to its magazine-worthy backyard and unbeatable Bronte location, this home is a fantastic opportunity in one of Oakville's most cherished neighbourhoods. More detailsListed by Century 21 Miller Real Estate Ltd.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
- Contact by Email
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1077 Bridge Road in Oakville: 1020 - WO West Single Family Residence for sale (1 - Oakville) : MLS®# 40850482
1077 Bridge Road Oakville L6L 2B6
$3,099,900Residential- Status:
- Active
- MLS® Num:
- 40850482
- Bedrooms:
- 5
- Bathrooms:
- 5
- Floor Area:
- 5,327 sq. ft.
1077 Bridge Road offers over 5,300 sq. ft. of finished living space on a landscaped 100' x 120' lot in sought-after West Oakville, minutes to downtown Oakville, Bronte Harbour, Lake Ontario, parks, the YMCA, top-rated schools, and Appleby College.A grand foyer with 10-foot ceilings, plaster crown moulding, and a hardwood staircase leads to a private office, formal dining room, and butler's servery with wine fridge. Wide-plank hardwood floors, 9-inch baseboards, custom millwork, coffered ceilings, and a gas fireplace complement the open-concept living space. The chef's kitchen features Sub-Zero, Wolf, and Bosch appliances, a large island, and breakfast area.The second level offers four bedrooms with ensuite access, including a primary suite with a walk-in closet and a heated-floor ensuite. A second bedroom has a private ensuite, while two others share a Jack-and-Jill bath. Second-floor laundry adds convenience.The finished lower level features heated floors, a spacious rec room with a stone gas fireplace, fifth bedroom, 3-piece bath, and flexible space for a gym, media room, or games area.Outside, enjoy a covered porch, stone patio, landscaped backyard with irrigation, Generac whole-home generator, security system, and epoxy-finished double garage. A custom-built home combining quality craftsmanship, functional design, and an exceptional West Oakville location. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
- Contact by Email
Data was last updated October 9, 2026 at 05:50 AM (UTC)
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