Oakville Luxury Real Estate
Trying to find Luxury Oakville homes for sale? Luxury Oakville Real Estate $2.5 Million Homes.
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2250 Chancery Lane W in Oakville: 1006 - FD Ford Single Family Residence for sale (1 - Oakville) : MLS®# 40792589
2250 Chancery Lane W Oakville L6J 6A3 
$8,750,000Residential- Status:
- Active
- MLS® Num:
- 40792589
- Bedrooms:
- 5
- Bathrooms:
- 7
- Floor Area:
- 9,177 sq. ft.
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. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
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- 1 (905) 6166821
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15 Chartwell Road in Oakville: 1011 - MO Morrison Single Family Residence for sale (1 - Oakville) : MLS®# 40794232
15 Chartwell Road Oakville L6J 3Z3
$11,750,000Residential- Status:
- Active
- MLS® Num:
- 40794232
- Bedrooms:
- 5
- Bathrooms:
- 7
- Floor Area:
- 10,281 sq. ft.
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 windows & French doors flood the house with light .Cascading waterfalls flank the hall.The Dining Room has statement lighting & servery making hosting a breeze.Soaring 18ft 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 w/ 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 13ft ceilings, an exquisite 6-pc ensuite &2 walk-in closets. A private balcony overlooks the yard.3 add'l bedrms have 10-ft ceilings,private ensuites & walk-in closets.The LL caters to all family members.A 5th bedroom/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 & walkout.Heated garage,baths & LL floors.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. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
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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
- RMXESCBU4BJ
- 1 (905) 6166821
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827 3500 Lakeshore Road W in Oakville: 1001 - BR Bronte Condo/Apt Unit for sale (1 - Oakville) : MLS®# 40794860
827 3500 Lakeshore Road W Oakville L6L 0B4
$2,799,000Residential- Status:
- Active
- MLS® Num:
- 40794860
- Bedrooms:
- 3
- Bathrooms:
- 4
- Floor Area:
- 2,708 sq. ft.
Elevate your lifestyle to unprecedented heights in this exquisite penthouse sanctuary, where sophisticated urban living meets breathtaking natural splendor. This remarkable three-bedroom, three-and-a-half-bathroom residence spans an impressive 2,708 square feet of meticulously crafted living space, designed for the most discerning homeowner. The southwest-facing orientation bathes the interior in golden light while showcasing panoramic vistas of the majestic escarpment and the endless expanse of Lake Ontario. The open-concept kitchen, adorned with lustrous new porcelain tile, features a striking island that serves as the culinary centerpiece, seamlessly connecting to the breakfast nook and intimate sitting area—a perfect orchestration of form and function. The thoughtfully designed split floor plan ensures privacy, with the primary bedroom suite positioned away from guest accommodations. Guest suites boast their own private ensuite and generous walk-in closets, creating a personal retreat. Throughout the residence, rich hardwood flooring adds warmth and timeless elegance. Step onto the spectacular wrap-around balcony accessible through multiple walkouts, complete with a BBQ gas line for personal grilling. The building exemplifies luxury living with resort-style amenities including a sparkling pool, tranquil sitting areas, fully equipped fitness center, rejuvenating whirlpool, sophisticated social lounge, and convenient guest suite. This penthouse represents the pinnacle of Oakville living, where every sunrise and sunset promises new possibilities. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
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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
- RMXESCBU4BJ
- 1 (905) 6166821
- Contact by Email
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170 Cavendish Court in Oakville: 1011 - MO Morrison Single Family Residence for sale (1 - Oakville) : MLS®# 40793328
170 Cavendish Court Oakville L6J 5S2
$2,548,000Residential- Status:
- Active
- MLS® Num:
- 40793328
- Bedrooms:
- 5
- Bathrooms:
- 4
- Floor Area:
- 2,760 sq. ft.
170 Cavendish Court is a rare offering in South East Oakville’s prestigious Morrison enclave. Set on a premium ravine lot with southwest exposure, this 5-bedroom, 4-bathroom residence delivers exceptional privacy, natural views, and a Muskoka-like setting that is increasingly hard to find. Thoughtfully updated in 2025, the home features wide-plank hardwood floors on the main and upper levels, hardwood stairs, a renovated chef’s kitchen, and tastefully updated bathrooms throughout. The functional layout includes elegant principal rooms, a home office, convenient laundry, and a private in-law suite—ideal for multi-generational living or added flexibility. Upstairs offers a serene primary retreat with renovated ensuite, plus three additional bedrooms and a 5-piece bath. The finished basement adds versatile living space. The backyard is a true retreat, featuring a multi-level deck and saltwater pool, seamlessly surrounded by mature trees and a tranquil creek backdrop. Walk to top-ranked schools with quick access to highways and GO Transit. Live, invest, or build—this is a rare opportunity to secure premium land, lifestyle, and long-term value in one of Oakville’s most established neighbourhoods. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
- Contact by Email
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297 Watson Avenue in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40796651
297 Watson Avenue Oakville L6J 3V3
$2,999,999Residential- Status:
- Active
- MLS® Num:
- 40796651
- Bedrooms:
- 4
- Bathrooms:
- 4
- Floor Area:
- 3,971 sq. ft.
Located in prestigious Old Oakville, this craftsman style home is a curated blend of enduring elegance and thoughtful contemporary design. Meticulously reimagined, where timeless character is enhanced by unsparing modern appointments. The stately exterior of new Bevel Lap wood siding and a custom solid wood door honours its distinguished surroundings. Inside, new hardwood floors flow through principal rooms grounded by sophisticated gas fireplaces. The gourmet kitchen is a culinary masterpiece with Thermador, Sub-Zero, and Miele appliances, serving as the heart of the home. A dramatic, custom 13-foot sliding door creates a seamless transition from the family room to the private, tree-lined grounds, blurring the lines between indoor and outdoor living. The primary suite is a private sanctuary, featuring a spa-like seven-piece ensuite with a custom vanity, quartz countertops, heated floors, and a luxurious soaker tub. Throughout the home, custom millwork, new solid wood interior doors, and a professionally appointed wine cellar with temperature control provide a touch of practical luxury. Located on coveted Watson Avenue, this home offers a lifestyle of unparalleled convenience. Stroll to downtown’s celebrated restaurants, the Oakville Trafalgar Community Centre, serene waterfront trails, and the GO Station. For those who value story and stewardship, this is more than a home; it is the continuation of a legacy. More detailsListed by Martin Group- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
- Contact by Email
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408 Saville Crescent in Oakville: 1020 - WO West Single Family Residence for sale (1 - Oakville) : MLS®# 40797222
408 Saville Crescent Oakville L6L 3T8
$4,295,000Residential- Status:
- Active
- MLS® Num:
- 40797222
- Bedrooms:
- 5
- Bathrooms:
- 4
- Floor Area:
- 4,134 sq. ft.
Every so often, a home comes along that sets a new benchmark. This custom-built residence combines timeless architecture, magazine-worthy interiors, and a resort-style backyard with over 6,100 sq. ft. of finished living space. Set on one of the largest pie-shaped lots in the neighbourhood (over 45% larger than average) and just 3km to Appleby College, it offers a rare sense of scale and privacy. Southwest-facing gardens showcase a heated saltwater pool, tiered lounging areas, ambient lighting, and mature hedging. Inside, 10’ ceilings, wide-plank hardwood, and bespoke millwork create quiet sophistication. The open-concept kitchen and family room with gas fireplace and French doors connect seamlessly to the gardens. A formal living room, elegant dining area, and private office complete the main floor. Upstairs, the primary suite rivals a luxury hotel with spa-inspired ensuite and dressing room, complemented by 3 bedrooms and laundry. The finished lower level adds a rec room with wet bar, gym, sauna, bedroom, and bathroom, ideal for teens, guests, or multigenerational families. More detailsListed by RE/MAX Aboutowne Realty Corp.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
- Contact by Email
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2201 Galloway Drive in Oakville: 1009 - JC Joshua Creek Single Family Residence for sale (1 - Oakville) : MLS®# 40797672
2201 Galloway Drive Oakville L6H 5M1
$2,895,000Residential- Status:
- Active
- MLS® Num:
- 40797672
- Bedrooms:
- 5
- Bathrooms:
- 5
- Floor Area:
- 4,665 sq. ft.
Custom-built residence in the heart of Joshua Creek (4,700 sq. ft. of living space) on a premium 59x165 foot lot with an in-ground pool. Thoughtfully designed and renovated main level features a gracious foyer, formal living and dining rooms, and a private office with cathedral ceiling-ideal for working from home. The family room showcases soaring ceilings, a fireplace and oversized ceiling-height windows. The kitchen was updated in 2020 and offers a large centre island, quality cabinetry, premium appliances, and walk-out to an expansive wood deck overlooking the pool, gazebo, and tranquil ravine setting. A main-floor laundry room with garage access and a convenient powder room complete this level.The upper floor luxurious primary suite complete with a spa-inspired ensuite (renovated 2020) and walk-in closet. Generously sized bedrooms with ensuite or semi-ensuite access overlook the open-to-below family room, enhancing the home's sense of light and volume.The professionally finished walk-out lower level (approx. 1,640 sq. ft.) featuring a large home theatre recr room with built-in bar and walk-out to the yard, a separate media room with fireplace, a dedicated music room, a den, a full bathroom, cold room, utility and ample storage - ideal for in-law suite. A new downstairs guest bedroom was completed in 2020.The spectacular backyard is a private retreat with a large deck, gazebo and a beautifully maintained in-ground pool, backing directly onto mature greenery for exceptional privacy. Located in a highly sought-after school district, top-ranked Joshua Creek Public School and Iroquois Ridge High School, and minutes to highways, shopping, parks, and all amenities, this move-in-ready home offers an outstanding combination of luxury, space, upgrades, and setting in one of Oakville's most desirable neighbourhoods. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
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234 Walby Drive in Oakville: 1017 - SW Southwest Single Family Residence for sale (1 - Oakville) : MLS®# 40796482
234 Walby Drive Oakville L6L 4E5
$4,250,000Residential- Status:
- Active
- MLS® Num:
- 40796482
- Bedrooms:
- 4
- Bathrooms:
- 6
- Floor Area:
- 4,108 sq. ft.
Designed to be enjoyed in all seasons, this decadently appointed custom built executive home in sought after Coronation Park delivers exceptional warmth and comfort, especially in the winter months. This spacious open concept home with 20ft soaring ceilings in the main living areas, features a MAIN FLOOR PRIMARY RETREAT with lavish ensuite. An abundance of natural light abounds from the bi-fold doors, expansive European double glazed low e-argon windows and six skylights, delivering exceptional insulation energy efficiency and year round comfort. Heated flooring (non wood areas), heated garage, heated driveway and walkway means life is much easier here! Outside the backyard transforms with seasons, offering a heated saltwater pool, double-sided gas fireplace, extensive patio, built-in kitchen and a private 2pc bathroom. Perfect for both summer entertaining and cozy winter evenings by the fire. Enjoy life by the lake, this exceptional home offers comfort all year long! More detailsListed by Royal LePage Realty Plus Oakville Ltd. and Re/Max Your Community Brokerage Limited- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
- Contact by Email
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1319 Greeneagle Drive in Oakville: 1007 - GA Glen Abbey Single Family Residence for sale (1 - Oakville) : MLS®# 40798525
1319 Greeneagle Drive Oakville L6M 2N1
$2,998,000Residential- Status:
- Active
- MLS® Num:
- 40798525
- Bedrooms:
- 5
- Bathrooms:
- 4
- Floor Area:
- 4,200 sq. ft.
Location! Location! Welcome to 1319 Greeneagle Drive nestled in the sought after Gated community of Fairway Hills. Quiet cul-de-sac plus granted access to 11 acres of meticulously maintained grounds. Backing onto the 5th fairway offering breathtaking views as soon as you walk in. This spectacular family home has been extensively renovated with well over 300K spent by the current owners. Painted throughout in crisp designer white, smooth ceilings, over 170 pot lights, updated 200amp panel, new shingles, skylight + insulation, stone driveway and walkway, commercial grade extensive home automation system with security/smart locks, EV ready and smart closet designs. The lower level has been professionally finished with a rec room, 5th bedroom, full washroom, gym and a fantastic pantry/storage room. The primary suite has been transformed to create his and hers closets and a spa- like ensuite with heated floors, glass curb less shower and soaker tub. Entertainers backyard with large deck and heated in ground pool. Close to top rated schools, hiking in the 16 mile trail system, shopping and highway access. Move in and enjoy! More detailsListed by RE/MAX Aboutowne Realty Corp.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
- Contact by Email
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46 Second Street in Oakville: 1013 - OO Old Oakville Single Family Residence for sale (1 - Oakville) : MLS®# 40799158
46 Second Street Oakville L6J 3T2
$8,479,000Residential- Status:
- Active
- MLS® Num:
- 40799158
- Bedrooms:
- 5
- Bathrooms:
- 7
- Floor Area:
- 6,830 sq. ft.
Discover an extraordinary custom built residence in prestigious Old Oakville, where architectural excellence meets modern luxury just steps from the lake.This 2024 Net Zero Ready masterpiece represents a distinguished collaboration between renowned industry leaders Chatsworth Fine Homes,architect John Willmott,and designer Jane Lockhart.The impressive foyer welcomes you with sophisticated elegance, flowing into a formal dining room adorned w/ dual chandeliers,herringbone white oak floors,and exquisite wall treatments.Panel moldings throughout create timeless continuity.The gourmet kitchen showcases premium Miele & SubZero appliances.This culinary centerpiece seamlessly connects to the Great Room,where a sleek linear f/p anchors custom built-ins and expansive windows extending to outdoor entertaining spaces.A servery,custom mudroom with exterior access,and private main floor office enhance functionality.Upstairs,the luxurious primary suite provides a serene sanctuary featuring a spa-inspired ensuite w/ freestanding tub,oversized shower,double vanity,makeup area & walk-in closet complete with island.Secondary bedrooms offer private ensuites & generous walk-in closets.All bathrooms include heated floors & curbless showers.A super functional laundry room is also on this level.The lower level transforms into an entertainment haven with spacious rec room, custom bar and kitchenette,bedrm, gym,3 & 2 pc bath,theatre room, and storage. Convenient walk-up access to the backyard.The outdoor oasis features a covered heated lounge,inground pool w/ waterfall,hot tub,and professional landscaping.Extra features incl heated driveway,west-facing yard capturing afternoon sun,partial lake views,radiant in-floor heating & Crestron home automation deliver unparalleled comfort and efficiency,R/I Tesla Supercharger & Generator.Tarion warranty.This remarkable residence epitomizes architectural distinction and refined living.LUXURY CERTIFIED. More detailsListed by RE/MAX Escarpment Realty Inc.- ELENA CIPRIANO
- RMXESCBU4BJ
- 1 (905) 6166821
- Contact by Email
Data was last updated February 8, 2026 at 07:50 PM (UTC)
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