Oakville Luxury Real Estate
Trying to find Luxury Oakville homes for sale? Luxury Oakville Real Estate $2.5 Million Homes.
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2054 Lakeshore Road E in Oakville: 1006 - FD Ford Single Family Residence for sale (1 - Oakville) : MLS®# 40756821
2054 Lakeshore Road E Oakville L6J 1M3 
$39,000,000Residential- Status:
- Active
- MLS® Num:
- 40756821
- 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
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421 Chartwell Road in Oakville: 1011 - MO Morrison Single Family Residence for sale (1 - Oakville) : MLS®# 40769933
421 Chartwell Road Oakville L6J 4A4
$6,999,000Residential- Status:
- Active
- MLS® Num:
- 40769933
- Bedrooms:
- 6
- Bathrooms:
- 8
- Floor Area:
- 7,908 sq. ft.
With a stunning backyard, 5,196 sq ft of above ground living, and quality construction built by Gatestone Homes, this home is truly the total package. Stone, wood, and striking Anderson windows have been eloquently incorporated on the exterior of the home, lending to the superb curb appeal. The thoughtful design fuses modern style with timeless elegance. The foyer of the home feels as though you are entering a luxury hotel, with a stunning floating staircase and a custom hanging light feature that is a piece of art in itself! The soaring two-storey foyer is flooded with natural light from oversized windows, creating a bright and welcoming space. A custom wooden piece subtly divides the foyer from the traditional dining room that is complete with a temperature-controlled wine room and glass doors that invite you to enjoy the expansive rear deck. The heart of the home is the open concept kitchen-family-dining space that is surrounded by windows and grounded by a beautiful gas fireplace. With an oversized island there is no shortage of space for you and your guests. Adjacent to the kitchen is a conveniently located powder room as well as a laundry/mudroom that can be concealed by a pocket door. The primary suite is a true oasis. With double door entry, a gas fireplace, and five-piece ensuite, no detail was overlooked. The three additional bedrooms all have ensuite access and walk-in closets. Completing this level is a laundry room and study area with built-in desk space. The 2,712 sq ft lower-level walk-up will not disappoint. The large recreation space features a built-in projector, billiards space, and wet bar. A home gym and two additional bedrooms as well as playroom/second home office finish off this space. Lush mature trees combined with meticulous landscaping will lure you to the rear yard. With approx. 1800 sq ft of outside living space, a gunite pool, and cabana, this backyard checks all the boxes! Enjoy the beautiful summer weather in this retreat-like home! More detailsListed by Century 21 Miller Real Estate Ltd.- ELENA CIPRIANO
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212 Southview Road in Oakville: 1020 - WO West Single Family Residence for sale (1 - Oakville) : MLS®# 40778680
212 Southview Road Oakville L6K 2P4
$3,449,800Residential- Status:
- Active
- MLS® Num:
- 40778680
- Bedrooms:
- 5
- Bathrooms:
- 6
- Floor Area:
- 5,659 sq. ft.
Premium 65 X 142+ Pool Size Lot, This Gorgeous Home Boasts Approx. 5,600 Of Finished Living Area With An Array Of Hi-End Finishes And All The Best In Both Quality Of Construction As Well As Interior Finishes. Beautiful Porcelain Tiles & Wide Plank Wood Flooring, 9 3/4 Baseboards, Solid Interior Doors To Custom Cabinetry & Wall Units. Large Impressive Kitchen Features A Large Island, Quartz Countertops, High-End Built In Appliances & Walk-In Pantry. Large Breakfast Area To Entertain Large Gatherings, Family Room With Walkout To Large Covered Entertainers Patio. Gorgeous Open Concept Main Floor. Work From Home In Your Private Den With B/In Desk & Book Shelf. Huge Laundry Room With Custom Cabinetry & Built-In Shelving. Exit To Your Extra Wide And Deep Garage With Drive Through Door To Rear Yard. Open Riser Staircase Top To Bottom. Walk To 2nd Floor Leads You To A Luxurious Master Bedroom With A Huge Walk-In Closet And A Gorgeous 5pc Ensuite With Heated Floors. 3 Other Large Bedrooms With Large Closets, Ensuite & Semi-Ensuite. One Bedroom Features A Huge Secondary Room That Can Be Used As A Media Room, Private Living Room, Office, Or As Another Bedroom. A Fully Finished Basement With Amazing Party Size Rec Room, 3-Pc Bath, 5th Bedroom, And Exercise Room. Large Cold Room Perfect To Finish As Fabulous Wine Cellar. Security Cameras & Alarm System. A Gorgeous Home With A Driveway Large Enough For 6 Cars On A Quiet A Mature Area Of Prime South Oakville! More detailsListed by RE/MAX REALTY SPECIALISTS INC SHERWOODTOWNE BLVD- ELENA CIPRIANO
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166 Maple Grove Drive in Oakville: 1011 - MO Morrison Single Family Residence for sale (1 - Oakville) : MLS®# 40781486
166 Maple Grove Drive Oakville L6J 4V1
$3,399,900Residential- Status:
- Active
- MLS® Num:
- 40781486
- Bedrooms:
- 5
- Bathrooms:
- 5
- Floor Area:
- 5,444 sq. ft.
Nestled in the heart of prestigious Southeast Oakville, 166 Maple Grove Drive presents a rare opportunity to own a classic Cape Cod residence on a private, mature 1/3-acre lot. Proudly owned by the same family since its original build, this cherished home exudes timeless character and refined charm. The property showcases an impressive 112 x 128-foot lot, surrounded by lush landscaping and enhanced by landscape lighting that creates a warm evening ambiance. The backyard oasis features a sparkling in-ground pool, multi-level deck and stone patio, and a dedicated pool shed—perfect for summer entertaining or quiet relaxation in complete privacy. Inside, this spacious family home offers over 5300 square feet of living space, with five bedrooms and five bathrooms, including a thoughtfully finished lower level for additional living and recreation space. The expansive bedroom suite over the double-car garage, complete with a separate staircase, offers flexibility for an in-law, nanny, or private guest suite. With elegant principal rooms, a bright kitchen overlooking the gardens, and classic architectural details throughout, this residence combines the grace of traditional design with the comfort and functionality demanded by today’s lifestyle. Perfectly situated among Oakville’s most distinguished addresses—minutes from top-rated schools, the lakefront, and downtown Oakville this property delivers both prestige and peaceful family living. More detailsListed by Royal LePage Burloak Real Estate Services- ELENA CIPRIANO
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116-120 Speers Road in Oakville: 1001 - BR Bronte Retail for sale (1 - Oakville) : MLS®# 40782416
116-120 Speers Road Oakville L6K 2E7
$6,600,000Commercial Sale- Status:
- Active
- MLS® Num:
- 40782416
- Floor Area:
- 10,000 sq. ft.
Fully tenanted retail plaza in the heart of Oakville’s main commercial corridor. Long-standing tenants with stable income and strong covenant strength. High-traffic location along Speers Road, minutes from the QEW and Kerr Village, surrounded by national retailers and major redevelopment projects. Ideal for investors seeking steady cash flow with future upside potential. Zoned for a variety of commercial uses with possible redevelopment play excellent opportunity in one of Oakville’s most sought-after nodes. More detailsListed by Keller Williams Edge Realty- ELENA CIPRIANO
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1225 Baldwin Drive in Oakville: 1011 - MO Morrison Single Family Residence for sale (1 - Oakville) : MLS®# 40784069
1225 Baldwin Drive Oakville L6J 2W4
$3,999,888Residential- Status:
- Active
- MLS® Num:
- 40784069
- Bedrooms:
- 5
- Bathrooms:
- 7
- Floor Area:
- 5,396 sq. ft.
Welcome to this exceptional Keeren Design luxury residence nestled at a quiet cul-de-sac off Morrison Road in prestigious Southeast Oakville. Set on a lush, professionally landscaped ravine lot with creek views, this 2 year new custom-built home offers around 5,400 sqft. of refined living space, exuding elegance, unparalleled craftsmanship, and modern innovation throughout.Stepping in through the triple-pane mahogany front entry, soaring 10 ceilings on the main floor and 9 ceilings upstairs are complemented by white oak hardwood floors, extensive plaster crown moulding, custom wainscoting, and a dramatic open-riser staircase. The chefs kitchen is outfitted with double centre islands, top of the line appliances, Riobel fixtures, Zomodo sinks, Top Notch cabinetry, and a second fully equipped spice kitchen. Additional features include main floor office with custom cabinetry, accent walls through-out, a built-in mudroom, and floor-to-ceiling fiberglass windows framing the ravine.2nd floor is entrenched with natural light through the flared skylight with LED Light Valance, all bedrooms feature custom panel detail, crown moulding, and private ensuites with Riobel fixtures, large-format tiles, heated floors, and wall-hung toilets. The spa-like primary ensuite includes a steam unit and LED valance lighting. The walk-up basement boasts a 5th bedroom with private ensuite, a bar, large recreation space, and a stunning under-garage theatre room wired for Dolby Atmos.Enjoy the private resort-like outdoor living with in-ground pool, paving stone patios, armour stone accents, and a smart RainBird irrigation system, 6"x6" privacy fence, stone skirt. Smart home features include motorized blinds, Lutron lighting, 16 hardwired security cameras, Ecobee, Honeywell security, MyQ garage control, CAT6 wiring, and a smart irrigation systemall designed for seamless living in Oakvilles most coveted neighborhood. More detailsListed by RE/MAX Hallmark Alliance Realty- ELENA CIPRIANO
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116 Chartwell Road in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40784042
116 Chartwell Road Oakville L6J 3Z6
$7,995,000Residential- Status:
- Active
- MLS® Num:
- 40784042
- Bedrooms:
- 3
- Bathrooms:
- 3
- Floor Area:
- 5,570 sq. ft.
Welcome to 116 Chartwell Road, one of Southeast Oakville's architecturally significant and environmentally advanced residences. Built to Net-Zero specifications, this home is a masterclass in modern sustainability, where wellness, technology and design exist in seamless harmony.This eco-friendly home prioritizes your health with a fully sealed building envelope, advanced insulation, and a geothermal system paired with a 14.49kW solar array. This ensures clean, energy-efficient living by reducing exposure to pollutants and maintaining exceptional indoor air quality and comfort. The open-concept layout is bathed in natural light featuring custom mahogany-framed floor-to-ceiling windows and a striking pyramid skylight. The gourmet kitchen features a generous Diamante Quartzite island, custom lacquered cabinetry, and top-tier Gaggenau appliances. The main floor primary suite is a serene retreat with a luxurious 5-piece ensuite featuring a steam shower and an oversized soaking tub. The home office, with its serene garden views and a floor-to-ceiling oak bookcase offers a calming workspace. Outdoors, a stylish covered patio with a mahogany-clad ceiling, dual Kenyon barbecues, a stainless steel hot tub, and surround sound creates an inviting space for relaxation and entertaining. Smart home technology seamlessly integrates audio-visual, lighting, and security systems, controlled via intuitive apps. The exterior impresses with Neolith cladding, automated gates,irrigation and lighting. A tandem four-car garage with a hydraulic lift and EV charging, extra outdoor parking speaks to the car enthusiast. In times of need the Generac generator covers the entire home. This is not simply a luxury home, it is a forward thinking modern masterpiece in one of Oakville's most prestigious enclaves. More detailsListed by Sotheby's International Realty Canada- ELENA CIPRIANO
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115 Charnwood Drive in Oakville: 1006 - FD Ford Single Family Residence for sale (1 - Oakville) : MLS®# 40784665
115 Charnwood Drive Oakville L6J 5G8 OPEN HOUSE: Mar 22, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, March 22, 2026 2:00PM - 4:00PM
$3,199,000Residential- Status:
- Active
- MLS® Num:
- 40784665
- Bedrooms:
- 6
- Bathrooms:
- 5
- Floor Area:
- 5,808 sq. ft.
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. More detailsListed by Century 21 Miller Real Estate Ltd.- ELENA CIPRIANO
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PH1 300 Randall Street in Oakville: 1013 - OO Old Oakville Condo/Apt Unit for sale (1 - Oakville) : MLS®# 40786091
PH1 300 Randall Street Oakville L6J 0G2
$5,999,900Residential- Status:
- Active
- MLS® Num:
- 40786091
- Bedrooms:
- 3
- Bathrooms:
- 4
- Floor Area:
- 3,337 sq. ft.
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 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 More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
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1081 Argyle Drive in Oakville: 1011 - MO Morrison Single Family Residence for sale (1 - Oakville) : MLS®# 40786555
1081 Argyle Drive Oakville L6J 1A9
$7,999,000Residential- Status:
- Active
- MLS® Num:
- 40786555
- Bedrooms:
- 5
- Bathrooms:
- 7
- Floor Area:
- 10,077 sq. ft.
An architectural masterpiece by renowned Gren Weis, this exceptional residence offers over 10,000 sq. ft. of luxurious living space on more than ½ an acre in one of Oakville’s most desirable lake-influenced neighbourhoods. Showcasing soaring ceilings, extensive millwork, and superb craftsmanship, the home features spacious, elegant rooms and a seamless flow for entertaining. All bedrooms include ensuite baths, while the lower level impresses with a wine cellar and theatre. Outside, enjoy covered terraces, a built-in outdoor kitchen, luxury cabana, mature gardens, and a stream with bridge surrounded by landscape lighting. A classically inspired front fountain and spectacular landscaping enhance the property’s distinguished presence on an important street. Close to top private and public schools, this private estate blends timeless design, quality, and sophistication in a truly remarkable setting. Luxury Certified. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
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408 Lakeshore Road W in Oakville: 1017 - SW Southwest Single Family Residence for sale (1 - Oakville) : MLS®# 40793876
408 Lakeshore Road W Oakville L6K 1G1
$4,500,000Residential- Status:
- Active
- MLS® Num:
- 40793876
- Bedrooms:
- 6
- Bathrooms:
- 8
- Floor Area:
- 8,981 sq. ft.
This is a remarkable vacant lot that includes drawings and building permit. House pictures are renderings and details are from the drawings. Embark on a life of uncompromised luxury with this architectural masterpiece by renowned architect David Small. Perfectly located South of Lakeshore steps from Appleby College, lake and downtown Oakville. Evoking a sophisticated "Laneway Country" atmosphere on a rare 90’ x 340’ lot with walk-out basement. The estate features a long circular private drive that frames a sun-drenched, West-facing backyard. The home is designed as the ultimate multi-generational sanctuary, that offers a rare "Double Primary" layout: a magnificent main-floor master suite for accessible luxury, plus a second-level master retreat with separate "His & Her" ensuites. The elevator services all three levels, ensuring effortless movement throughout soaring interiors defined by dramatic cathedral ceilings. With building permits in hand and a bespoke interior package by WOLFE Interior Design, this Net Zero Ready estate blends timeless character with elite modern performance. Car enthusiasts will prize the 5-car capacity, utilizing the attached garage and the detached tandem garage within the cabana. Beyond the essentials, the floor plan is packed with exceptional features, including a main floor office, lower level dedicated music/theater room, glass-walled fitness center, custom sauna and steam room, wine cellar, and private nanny and guest suites. Surrounded by 10M-12M estates. Architectural drawings, interior design, floorplans and building permits available on request. 10+++ More detailsListed by RE/MAX Aboutowne Realty Corp.- ELENA CIPRIANO
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540 Patricia Drive in Oakville: 1020 - WO West Single Family Residence for sale (1 - Oakville) : MLS®# 40795474
540 Patricia Drive Oakville L6K 1M2
$3,999,000Residential- Status:
- Active
- MLS® Num:
- 40795474
- Bedrooms:
- 5
- Bathrooms:
- 5
- Floor Area:
- 3,200 sq. ft.
Step into this newly constructed custom residence which showcases bespoke built-in cabinetry fine craftsmanship. Stately nine-foot ceilings on the first and second floors from the wood flooring to the large scale windows you will sense refinement. Cozy in floor heating throughout the basement and all stone floors on the main and second floor includes a decadent heated garage floor, meaning no need to bundle up to access the garage making it a functional space of the home. The property is consistent with creature comforts featuring dedicated upper and lower hvac systems, circulating instant hot water throughout, and three gas fireplaces. Included is a comprehensive security system with cameras. The exterior façade combines elegant stone elements with stunning composite wood features, oversized front landing, 4 season inviting back deck with it’s own gas fireplace. Landscaping includes lighting with the addition of integrated driveway lighting to guide your way home. Luxury certified. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
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- 1 (905) 6166821
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Data was last updated March 18, 2026 at 05:50 PM (UTC)
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