Oakville Real Estate | Oakville Properties over $5,000,000 for Sale

An exceptional opportunity to own a substantial 11,000 sq. ft. four-storey office building in the heart of downtown Oakville. Ideally located within walking distance of Oakville's vibrant downtown, restaurants, cafés, shops and amenities. Featuring high-end executive finishes, the property currently serves as the headquarters of a prestigious financial wealth management firm catering to high-net-worth clients. The sophisticated layout includes multiple private offices, boardrooms, four kitchens, two fireplaces and an outdoor patio. The flexible configuration provides an excellent opportunity for an owner-user, corporate headquarters or multi-tenant investment strategy. A rare downtown Oakville offering combining scale, quality, location and flexibility-ideal for investors or professional users seeking a distinctive commercial property in one of Oakville's most desirable business locations.

305 Church Street, Oakville

$6,575,000

5 Beds ⋅ 5 Baths ⋅ W13779262 MLS

153 Balsam Drive is a sophisticated 4,337 sqft custom residence set on a 50' x 304' park-like lot in one of Oakville's most sought-after settings. Close to Downtown Oakville, top-rated schools, the home pairs craftsmanship with thoughtful functionality. A dramatic double-volume marble foyer with heated flooring and architectural staircase creates an elegant arrival, while custom millwork, designer lighting, oversized windows and premium white oak flooring establish a refined aesthetic throughout. The main level is designed for family living and entertaining, with gracious living and dining spaces flowing into a warm family room with a wood-burning fireplace. A dedicated office overlooks mature greenery. At the heart of the home, the kitchen features a 10' x 4' marble island, face-frame cabinetry, marble surfaces, bespoke lighting and a 60" Lacanche range with a custom plaster hood. A marble-finished pantry and heated natural-stone mudroom add function and elegance. Upstairs, four bedrooms each feature a walk-in closet. The primary suite offers a vaulted ceiling, double skylights with remote blinds, a lounge area and an oversized walk-in closet. The spa-inspired ensuite features heated marble floors, a steam shower with double heated marble seating, custom wainscoting, detailed marble trim and an imported Water Monopoly bathtub. The lower level extends the home's living and entertaining spaces with 10' ceilings and zoned underfloor heating. A fifth bedroom, recreation and games rooms, gym, wine cellar and theatre/flex space offer exceptional versatility for family living and entertaining. A heated three-car garage with car-lift capacity for two additional vehicles, plus exterior snow-melt infrastructure, adds year-round convenience. 153 Balsam Drive is a rare combination of timeless architecture, refined materials, modern functionality and exceptional attention to detail, thoughtfully brought together on one of Oakville's most coveted streets.

153 Balsam Drive, Oakville

$6,399,998

6 Beds ⋅ 8 Baths ⋅ W13777260 MLS

Welcome to an approx. 7,500 sq ft of exceptional living in Southeast Oakville! Set on a professionally landscaped almost half-acre lot in the prestigious Eastlake, this custom Hightower-built estate offers thoughtfully designed, luxurious space. The crown jewel of the home is a newly upgraded, million-dollar backyard oasis. Including a 600 sq ft covered patio with a built-in kitchen with a Napoleon BBQ, a gas fireplace, a saltwater pool with spillover spa, a dedicated play area, and lush perennial gardens. Retreat to an 800 sq ft primary retreat, delivering privacy and true wow factor with vaulted ceilings, two-sided fireplace, wet bar, sitting area, boutique walk-in closet, and a spa-like ensuite featuring heated floors, a soaker tub, and a glass shower. The main floor is designed for both grand entertaining and everyday comfort with natural light pouring through oversized windows. Interior features include 10-foot ceilings, chevron-patterned wide plank hardwood, LED pot lights, built-in speakers, and designer chandeliers. The chef's kitchen is finished in dual-tone lacquered cabinetry with Caesarstone counters, premium Dacor appliances, a bright breakfast area, and a butlers server that connects to the sophisticated dining room. A sleek linear fireplace anchors the family room. The home office stands out with 15-foot cathedral ceilings, a fireplace, custom built-ins, and a walkout to the gardens. Above, you'll find three generously sized bedrooms, each with radiant heated ensuite baths and custom closets. Downstairs, the walk-up lower level is built to impress with a full wet bar, wine cellar, large rec room, two guest bedrooms, a gym with cushioned flooring, cedar infrared sauna, and a new two-tiered home theatre. Additional features include a Control4 smart home system, a two-car garage with car lift potential, and a location just minutes from top-rated public and private schools, lakefront parks, downtown Oakville, and QEW access for a seamless Toronto commute.

231 Wedgewood Drive, Oakville

$7,188,000

5 Beds ⋅ 7 Baths ⋅ W13776348 MLS

Crafted by the celebrated designer Gren Weis, this extraordinary estate stands as a testament to architectural brilliance, delivering more than 10,000 square feet of refined living across an expansive half-acre property in one of Oakville's premier lakeside enclaves. Every detail reflects master-level craftsmanship, highlighted by dramatic soaring ceilings, rich custom millwork, and an effortless layout designed to host grand gatherings or intimate family moments with equal grace. The main living areas transition smoothly into generously proportioned rooms filled with natural light. On the upper level, the home features private suites for all bedrooms, each accompanied by its own dedicated luxury ensuite bath. The lower level serves as an elite entertainment retreat, thoughtfully appointed with a climate-controlled wine cellar and a private cinematic theatre room that provides an immersive movie-going experience right at home. Outdoors, the resort-style grounds unfold into a breathtaking private sanctuary. Covered stone terraces provide space for year-round alfresco dining, complete with a fully equipped built-in outdoor kitchen and a resort-inspired luxury cabana. Meandering through the lushly planted mature gardens, a picturesque bridge crosses a natural stream, all beautifully illuminated in the evenings by custom accent landscape lighting. At the front of the property, a classic tier-inspired fountain and meticulous stonework set a commanding tone, bestowing the residence with an unmistakable and distinguished street presence on a prominent Oakville avenue. Located just moments from the region's highest-ranked public and private academies, this landmark residence seamlessly harmonizes timeless architectural prestige, modern everyday comfort, and sheer sophistication in an unrivaled setting. Luxury Certified

1081 Argyle Drive, Oakville

$5,190,000

6 Beds ⋅ 8 Baths ⋅ W13770700 MLS

SPECTACULAR CUSTOM-BUILT MODERN FARMHOUSE BY RICHCO DEVELOPMENT IN PRESTIGIOUS SOUTH-EAST OAKVILLE! Situated on an exceptional 79' x 151' mature lot, this newly constructed residence offers approximately 7,000 sq.ft. of exquisitely designed living space across all levels, including an impressive walkout lower level. Thoughtfully designed for both refined everyday living and grand-scale entertaining, this extraordinary home features elevator access to all three levels, soaring ceiling heights, extensive natural stone finishes, and expansive walls of glass throughout.The breathtaking family room showcases a dramatic 23-foot feature wall, heated flooring, a remarkable custom crystal chandelier inspired by the iconic Waldorf Astoria lobby, and a stunning floor-to-ceiling glass curtain wall. The designer kitchen is anchored by two oversized islands, premium Sub-Zero and Wolf appliances, and a fully equipped chef's kitchen, creating the perfect setting for everyday living and entertaining.The upper level is highlighted by a spectacular skylight and luxurious bedroom suites, while the walkout lower level offers exceptional additional living space complete with a sauna, steam room, jacuzzi, and a dedicated theatre room.Bi-fold doors open seamlessly to a covered porch overlooking the expansive backyard with pool potential. Surrounded by mature trees and located moments from top-rated schools, parks, and the lake, this extraordinary residence offers a rare combination of scale, craftsmanship, architectural sophistication, and timeless elegance in the heart of South-East Oakville.

1477 Duncan Road, Oakville

$9,180,000

6 Beds ⋅ 5 Baths ⋅ W13765232 MLS

Gracefully located at the foot of Trafalgar Road in the heart of prestigious Old Oakville, this extraordinary lake view estate presents a rare opportunity to own one of the area's most distinguished residences. Set on an expansive 155' x 104' property, the home enjoys breath taking views of Lake Ontario, offering ever-changing waterfront vistas, spectacular sunrises, and an unparalleled lifestyle just steps from the town's vibrant downtown core. Steeped in history and meticulously transformed into a magnificent custom residence, this approximately 10,000 sq. ft. home spans three levels of refined living space. Featuring six spacious bedrooms and nine luxurious bathrooms, every detail has been thoughtfully designed to blend timeless elegance with modern comfort. The grand interior showcases soaring ceilings, a custom chef's kitchen, sophisticated entertaining spaces, and designer finishes throughout. Exceptional amenities include a private elevator, walk-in wine cellar, fully equipped fitness area, loft space, and a walk-out lower level ideal for extended family, guests, or a nanny suite. The home's striking exterior seamlessly blends timeless architectural character with refined modern updates. Natural stone and wood exterior finishes create an elegant façade that complements its coveted waterfront setting. The expansive, maturely landscaped grounds provide exceptional privacy while maximizing lake views from multiple outdoor vantage points. It boasts your own private putting green, a fire pit area, expansive deck/entertaining area including a pizza oven and gorgeous salt water pool with a captivating water fall. Beyond the home, residents enjoy an enviable walkable lifestyle with immediate access to the lakefront, marina, scenic trails, parks, boutique shopping, cafés, and fine dining. Combining historic character, exceptional craftsmanship, and a premier waterfront-adjacent location, 26Trafalgar Road represents luxury Oakville living at its finest.

26 Trafalgar Road, Oakville

$10,950,000

5 Beds ⋅ 7 Baths ⋅ W13754954 MLS

Experience breathtaking, panoramic views from this stately lakefront estate, a true sanctuary of elegance and tranquility. Nestled on an expansive 3/4 acre lot, this rare gem boasts an impressive 100 feet of private lake frontage with riparian rights, ensuring unobstructed access to the shimmering waters of Lake Ontario. Spanning 5,800 sq. ft. (excluding the basement), this residence is designed for those who appreciate refined living and timeless sophistication. Step through the grand foyer into an atmosphere of classic luxury, where generous principal rooms flow effortlessly, highlighted by exquisite hardwood flooring and elegant finishes. Two stunning solariums maximize the lake's mesmerizing vistas, creating sun-drenched spaces perfect for relaxation and entertaining. The gourmet kitchen is a chef's dream, featuring a sprawling marble-topped island and an open layout designed for both functionality and style. Upstairs, five spacious bedrooms await, including the lavish primary suite, a private retreat with His & Hers walk-in closets and a spa-like 6pc ensuite bath. A versatile bonus room above the garage offers the perfect hideaway for a teen retreat, nanny suite, or home office. Outdoors, the beautifully landscaped backyard is an entertainer's paradise, complete with a sparkling inground pool, a picturesque patio, and the lake's serene backdrop enhancing every moment. A private gate leads directly to the lush surroundings of Gairloch Gardens, adding to the home's enchanting setting. Located in one of Oakville's most prestigious neighbourhoods, this exceptional property is just minutes from top-rated schools, fine dining, and the boutique shopping of Downtown Oakville. A rare opportunity to own a piece of lakeside luxury.

16 Ennisclare Drive W, Oakville

$7,250,000

7 Beds ⋅ 9 Baths ⋅ W13749712 MLS

Set within one of Oakville's most distinguished enclaves, 84 Pebbleridge Place is a newly built modern estate that epitomizes architectural artistry and offers over 7,000 SF of refined living space. Poised on a private lot, this residence showcases a brick and limestone exterior, full-height glass walls a curated palette of luxurious finishes for the most discerning buyer. A grand double-height foyer introduces the home w/ polished marble-style porcelain and bespoke detailing. Beyond, herringbone hardwood floors flow through expansive principal rooms to a family room defined by a sleek wood feature wall, gas fireplace, and integrated Control4 automation for effortless entertaining. The designer kitchen is both statement and function, featuring an oversized island, full-height custom cabinetry, and Calacatta-style quartz counters w/ a custom backsplash. It opens directly to a covered deck w/ a gas fireplace, perfect for al fresco dining and evenings. An elevator and striking skylit staircase lead to the upper level, where four bedrooms each feature walk-in closets, tray ceilings, and private ensuites finished to spa-like standards. The primary suite is a serene retreat w/ a boutique-style dressing room and five-piece ensuite boasting a freestanding tub, oversized glass shower, full-height stone surrounds, and heated flooring. The lower level continues the theme of luxury and versatility, offering a heated basement w/ large-format porcelain slab flooring throughout. Designed for both relaxation and entertainment, this level includes a secondary kitchen, dining area, expansive living space, fitness room w/ cushioned flooring, an acoustically designed theatre, and three additional ensuite bedrooms, all enhanced by full-size windows and a separate entrance. Additional highlights include: a rough-in sauna, built-in speakers, and recessed lighting elevate comfort and ambiance, while upper-level laundry & a tandem garage w/ epoxy flooring complete this modern masterpiece.

84 Pebbleridge Place, Oakville

$10,900,000

5 Beds ⋅ 4 Baths ⋅ W13738344 MLS

Situated on just over half an acre on the shores of Lake Ontario, 10 Brookfield Road is a truly exceptional waterfront property offering an extraordinary combination of views, privacy, recreation and year-round enjoyment. With unobstructed vistas of Lake Ontario from virtually every angle, the setting is as captivating as it is rare. The property's exceptional waterfront experience begins with riparian rights- the ultimate in waterfront living - and is highlighted by a detached boathouse with dedicated boat storage and a marine rail. Above, a spacious viewing deck and built-in gazebo create an ideal setting for entertaining, intimate gatherings, a lakeside bar or live music, all overlooking breathtaking panoramic views of the lake. Beyond the waterfront, an in-ground swimming pool and pool house with change rooms create a private, resort-like environment for summer entertaining and relaxed days at home. A parkette immediately to the east adds an exceptional sense of privacy, openness and seclusion rarely found in such a prominent waterfront setting. The natural topography creates distinct elevations and vantage points, allowing the home and outdoor spaces to fully embrace the lake. Inside, the spacious great room is designed for both everyday living and entertaining, complemented by an updated kitchen, walkout lower level and expansive windows that flood the home with natural light and showcase the views. Multiple walkouts provide seamless access to generous decks and outdoor entertaining spaces. Ideally located in close proximity to Lakeshore and Kerr Village, the property is also only a 15-minute walk to Downtown Oakville, offering convenient access to shops, restaurants, cafes and the vibrant village atmosphere. Whether enjoying a quiet morning overlooking the water, hosting friends poolside or launching a boat from the boathouse, 10 Brookfield Road is a truly rare waterfront offering. Luxury Certified.

10 Brookfield Road, Oakville

$5,900,000

6 Beds ⋅ 8 Baths ⋅ W13735244 MLS

Extraordinary custom smart home offering over 8700sqft luxury living space (5711 sqft above grade as per MPAC) on one of Oakville's most prestigious and sought-after streets. Situated on a rare 100 x 200 west-facing premium lot, with soaring 10ft high ceilings, 4+2 bedrooms/8 bathrooms/3 car garage, this home has been thoughtfully designed with exceptional attention to detail, blending timeless elegance with modern convenience.Step inside the grand 2-storey foyer, leading to a sophisticated coffered living room with gas fireplace and custom built-ins, and a formal dining room with panelled walls. The open-concept chefs kitchen is a showpiece, featuring a massive centre island, quartz and granite countertops, stainless Thermador appliances, a butler's servery, and walkout to the covered terrace. A panelled office, main floor laundry, and exquisite finishes throughout complete the main level.The upper level hosts 4 spacious bedrooms, each with private ensuites, including a primary retreat with a sitting area, fireplace, opulent dressing room, and a spa-inspired 6-piece marble ensuite with standalone tub and double sinks.The finished lower level is designed for entertainment and relaxation, offering an expansive recreation room with linear fireplace, wet bar, wine cellar, theatre, exercise room, sauna, 4-piece bath with jacuzzi tub, and radiant heated floors, a walk-up leads to the private backyard oasis.Outdoors, enjoy a beautifully landscaped west-facing backyard with a covered terrace, glass railing, stone fireplace, built-in Napoleon barbecue, and speakers, perfect for hosting. The lot provides ample potential for a large pool, tennis court, or basketball court at your choice. A 3-car tandem garage with radiant heat, mudroom access, and lower-level entry.This rare offering is a true masterpiece combining Control4 smart home features, refined craftsmanship, and resort-style amenities.

482 Morrison Road, Oakville

$5,399,000

5 Beds ⋅ 5 Baths ⋅ W13729598 MLS

WATERFRONT PROPERTY! Experience the Potential of Lakeside Living. Perfectly situated on a premium 90' x 152' lakefront lot, this residence offers breathtaking, unobstructed water views from every principal room. With over 5,700 square feet of finished living space, the home presents an exceptional opportunity to bring your vision to a truly remarkable waterfront setting. The existing layout offers generous space for family living and entertaining, with rich hardwood flooring, limestone tiles, four skylights, two spacious family rooms, a private office, and a large kitchen with lake views! Upstairs, four generously sized bedrooms provide excellent space and privacy, while the primary suite showcases spectacular lake views. A convenient upper-level laundry room and walkout to the second-floor terrace offer additional potential to create a beautiful retreat overlooking the water. The fully finished lower level includes a fifth bedroom with a private ensuite, ideal for guests, extended family, or a nanny suite. Outdoors, the property offers an incredible foundation for creating your own waterfront oasis. The views, privacy, and ever-changing beauty of the waterfront truly have to be experienced to be fully appreciated, as the changing seasons, light, and skies create a new view from moment to moment. Additional highlights include a three-car garage, four fireplaces, an irrigation system, and ample storage throughout. This is a rare opportunity to transform an expansive waterfront property into a spectacular lakeside home, while enjoying the privacy, scale, and extraordinary setting that cannot be replicated. Luxury Certified.

2372 Carrington Place, Oakville

$15,900,000

5 Beds ⋅ 4 Baths ⋅ W13728088 MLS

Build your dream home on South East Oakville's prime waterfront. With 184 feet of lake frontage and unparalleled views of the Toronto skyline, this building lot is the largest remaining and developable Riparian Lakefront parcel in South East Oakville available. Located on one of Oakville's most sought-after and mature tree lined streets and walking distance to downtown Oakville, this breathtaking and private lot offers approximately 0.77 acres of land and a further water lot of 2.86 acres. The land can comfortably accommodate a new custom home of up to10,000 square feet (not including basement) without a variance. The property is also the furthest projected vantage point for uninterrupted panoramic views in Oakville. With an extremely rare concrete dock for boat mooring and recent new Seawall (2020), this private lot offers an opportunity to build your lakefront home in Oakville's most coveted neighbourhood, with easy access to Toronto and in one of Ontario's top school districts. This is the ultimate lakefront property in Oakville, the possibilities are endless. The current home allows you to live in now or build new for your dream lifestyle.

3 Ennisclare Drive E, Oakville

$15,900,000

W13725602 MLS

Build your dream home on South East Oakville's prime waterfront. With 184 feet of lake frontage and unparalleled views of the Toronto skyline, this building lot is the largest available and developable Riparian Lakefront parcel in South East Oakville. Located on one of Oakville's most sought-after streets and walking distance to downtown Oakville, this breathtaking and private lot offers approximately 0.77 acres of land and a further water lot of 2.86 acres. The land can comfortably accommodate a new custom home of up to 10,000 square feet (not including basement) without a variance. The property is also the furthest projected vantage point for uninterrupted panoramic views in Oakville. With an extremely rare concrete dock for boat mooring and recent new Seawall (2020), this private lot offers an opportunity to build your lakefront home in Oakville's most coveted neighborhood, with easy access to Toronto and in one of Ontario's top school districts. Build the ultimate lakefront property in Oakville, the possibilities are endless.

3 Ennisclare Drive E, Oakville

$6,250,000

6 Beds ⋅ 7 Baths ⋅ W13724050 MLS

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 patio 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.

533 Carson Lane, Oakville

$13,500,000

5 Beds ⋅ 6 Baths ⋅ W13723478 MLS

Designed by architect Gren Weis and built by Lakehurst Construction, this exceptional custom estate is beautifully positioned on the shores of Lake Ontario in one of South-East Oakville's most prestigious waterfront enclaves. Set on a remarkable property with coveted riparian rights, the residence offers breathtaking lake views, exceptional privacy, and a seamless blend of timeless architecture and modern luxury.Classical proportions and outstanding craftsmanship are showcased throughout, with intricate millwork, detailed ceilings, radiant heated floors, and upgraded lighting. Generous principal rooms are thoughtfully positioned to maximize sweeping water views. The main level features a magnificent living room with double French doors opening to the lake breeze, a light-filled solarium overlooking landscaped gardens, an elegant dining room, and a gourmet kitchen with professional-grade appliances and dedicated prep kitchen. A sun-filled family room with striking waffle ceilings completes the space. Upstairs, the serene primary retreat offers spectacular views, a spa-inspired ensuite, and beautifully appointed dressing room. Three additional bedrooms, two elegant bathrooms, and a sophisticated lake-view library complete the level.The lower level offers full-size windows, radiant heated floors, a recreation room with wet bar, fitness studio with full bathroom, private guest suite with ensuite, and extensive storage. Outside, manicured gardens flow naturally toward the shoreline, creating a private waterfront setting designed to be enjoyed throughout the seasons. Multiple walkouts provide effortless access to the grounds and lake, where morning paddleboarding, or an evening canoe launch can become part of everyday life. Steps from Gairloch Gardens and minutes from Downtown Oakville's boutiques, restaurants, cultural amenities, and highly regarded schools, this extraordinary estate offers the very best of South-East Oakville waterfront living

6 Ennisclare Drive W, Oakville

$13,995,000

W13715888 MLS

Here is a rare opportunity to create your dream home on one of Oakville's last remaining waterfront building lots, ideally positioned on one of the town's most prestigious streets and within walking distance of downtown Oakville. More than two years of planning, approvals and meticulous attention to detail have gone into preparing this exceptional property for its next chapter. The result is a spectacular waterfront setting, complete with an extraordinary custom boardwalk and dock designed to create the ultimate lakeside lifestyle and entertaining experience for family and friends. Situated on over half an acre with approximately 125 feet of frontage along the water, this magnificent lot offers an increasingly rare combination of privacy, scale and direct access to Lake Ontario.Bring your own vision and complete the design of your dream residence, or take advantage of plans by renowned SMPL Design Studio for a striking modern masterpiece offering more than 11,000 sq. ft. of living space.The newly constructed boardwalk and dock have been thoughtfully designed and engineered with exceptional attention to detail and longevity, creating a waterfront amenity intended to be enjoyed for decades to come.A truly irreplaceable opportunity to build an extraordinary waterfront residence in the heart of Old Oakville.

1044 Argyle Drive, Oakville

$9,995,000

5 Beds ⋅ 6 Baths ⋅ W13707486 MLS

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

15 Chartwell Road, Oakville

$7,599,000

5 Beds ⋅ 7 Baths ⋅ W13694012 MLS

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.

46 Second Street, Oakville

$7,998,000

5 Beds ⋅ 6 Baths ⋅ W13643716 MLS

Welcome to 1472 Oakhill Drive, a newly built contemporary residence in the heart of prestigious South East Oakville, where timeless sophistication meets exceptional craftsmanship. Offering nearly 7,800 sq.ft. of exquisitely finished living space across three levels, this custom designed home delivers an elevated lifestyle defined by refined architecture, luxurious finishes and effortless indoor-outdoor living. A striking façade with a metal roof, heated driveway and walkways, professional landscaping and a triple tandem garage creates an unforgettable first impression. Inside, soaring 10-foot ceilings, a dramatic two-storey foyer, solid mahogany entry door and bespoke millwork throughout set the tone for the home's impeccable attention to detail. Designed for both elegant entertaining and everyday living, the open concept main floor features a stunning chef's kitchen appointed with premium Gaggenau integrated appliances, custom cabinetry, and seamless access to the spectacular outdoor living spaces. The covered rear porch is a true extension of the home, complete with automated retractable screens, a built-in outdoor kitchen, cedar tongue-and-groove ceiling and generous lounge and dining areas. The resort inspired backyard is centred around a 14' x 34' saltwater Gunite pool with an integrated hot tub, waterfall feature and a custom cabana. The second level offers four spacious bedrooms, each with a private ensuite and custom closet solutions, creating a luxurious retreat for every family member. The finished lower level adds exceptional versatility with a fifth bedroom, a full bathroom, and expansive recreation and entertainment space. Set on one of South East Oakville's most desirable streets, this exceptional residence combines modern design, superior construction, and resort-calibre amenities in a location renowned for its top-ranked schools, lakefront parks, and proximity to downtown Oakville. A rare opportunity to own a truly distinguished custom home.

1472 Oakhill Drive, Oakville

$6,499,000

W13633276 MLS

Some properties simply cannot be replicated. Set along one of South East Oakville's most prestigious waterfront streets, this exceptional offering represents one of the area's last opportunities to create a truly landmark custom estate.Occupying approximately 0.59 acres with 99 feet of private pebble shoreline, Riparian Rights and nearly 300 feet of depth, the property enjoys breathtaking, uninterrupted views across Lake Ontario while mature trees provide an extraordinary sense of privacy. The property offers an exceptional backdrop for a custom residence designed to embrace every aspect of waterfront living.With the potential to build over 8,000 sqft custom home (plus basement, subject to all applicable approvals), the possibilities are endless. Grand principal rooms, seamless transitions to outdoor living spaces and resort-inspired amenities can all be thoughtfully incorporated to maximize the property's panoramic lake views.Life on the water becomes part of your everyday routine. Launch a kayak or paddleboard directly from your own shoreline, enjoy coffee overlooking the lake, or simply experience the tranquility that only true lakefront living can provide.Despite its remarkable sense of seclusion, the property is only minutes from Downtown Oakville's boutique shops, acclaimed restaurants, marinas and waterfront amenities. Located within one of Ontario's most highly regarded school districts, this is an opportunity to create not simply a home, but a lasting family legacy in one of South East Oakville's most exclusive lakefront communities.

2288 Chancery Lane W, Oakville

$7,249,000

5 Beds ⋅ 5 Baths ⋅ W13625250 MLS

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,outdoor shower, 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. Every detail has been thoughtfully curated to deliver timeless elegance & intelligent technology. Approximately 7000 Sq. ft. Livingspace. Luxury Certified.

54 RAYMAR Place, Oakville

$6,975,000

3 Beds ⋅ 3 Baths ⋅ W13594134 MLS

Lakefront home, nestled on Old Oakville's Second Street, this residence offers a blend of timeless elegance, luxury, and unparalleled waterfront living. Completely reimagined top to bottom, showcasing an aesthetic designed for both family living and comfortable downsizing. Bathed in natural light, offering breathtaking lake views from nearly every room, you will find tranquility and grandeur from the moment you enter. Glowing hardwood flooring, custom millwork and paneling, recessed lighting, and designer finishes elevate every space.The kitchen, with panoramic lake views, features custom cabinetry, integrated top-of-the-line appliances, and an oversized island with seating for four. Quartz countertops and full-height quartz backsplash create a striking focal point, complemented by gold pendant lighting.The living room is designed for both comfort and style, featuring custom built-in cabinetry with illuminated shelving, gas fireplace, and expansive windows framing the sparkling waters of Lake Ontario. The main-floor primary suite, spacious and serene, featuring a walk-in closet. Spa-inspired ensuite with a freestanding soaker tub, glass walk-in shower, vanity, and gold fixtures and lighting. Two additional bedrooms on the upper level for family and guests, with private balcony overlooking the waterfront. Enjoy a beautifully appointed main-floor laundry room with custom cabinetry and stacked appliances. Enjoy riparian rights from a spectacular waterfront deck featuring glass railings and steps to the shoreline. Maximizing the panoramic water views, an unrivaled setting for entertaining, relaxing, and embracing Oakville's most prestigious waterfront lifestyle. Complete with a detached 2 car garage and ample private parking. Furniture by FOR living, Art by Harbour Gallery. Luxury Certified.

21 Second Street, Oakville

$17,300,000

W13490470 MLS

One of the last few opportunities to invest in development employment lands along the Oakville & Mississauga border. The site has unparalleled access to Highway 403, Highway 407, Dundas Street West and the newly constructed William Halton Parkway. The subject lands are amongst many parcels of land that are owned by some of Ontario's biggest commercial developers such as Erin Mills Development Corp. and Anatolia Tile. Most recently the 25 acres of vacant land to the north, located at 3480 Ninth Line, has been purchased by HIVE BUZZ HPC (High Performance Computing) a division of HIVE Digital Technologies for the development of a 320 MW AI Infrastructure data center that is aiming to be operational in the second half 2027. In recent consultations with local, Regional and Provincial authorities in Planning and Development, they indicated that there are discussions underway with a number of the developers in the immediate area to speed up timelines for servicing of the vacant land parcels along Ninth Line and William Halton Pkwy. Previously approved road widening of Ninth Line from two to four lanes is currently in the design phase. Commencement of construction for the road widening is projected to start late 2027 or early 2028.

N/A Ninth Line, Oakville

$5,250,000

4 Beds ⋅ 6 Baths ⋅ W13585382 MLS

Exceptional custom-built luxury home with approximately 4,655 sq. ft., plus the professionally finished basement on a premium 185' deep lot with west exposure, on one of Southwest Oakville's coveted lakeside streets. Steps to Lake Ontario, & a 20-minute walk to historic downtown Oakville, Oakville Harbour, trendy shops & restaurants, & close to major highways & GO Station. Outstanding curb appeal highlighting a timeless stone exterior, exposed aggregate driveway, natural stone walkways, iron fencing, irrigation system, manicured gardens & mature trees. The spectacular resort-style, dream backyard features an in-ground saltwater pool, raised hot tub, expansive stone patios, custom gazebo, covered terrace area with ceiling fans & heaters, cabana with serving bar, lush gardens, & a tranquil waterfall & creek surrounded by mature trees for exceptional privacy. The elegant interior features soaring ceilings, hardwood floors, deep crown mouldings, custom cabinetry, pot lights, built-in speakers, 4 gas fireplaces, oversized windows & walkouts, with custom blinds & draperies. Designed for both entertaining & family living, the home offers a stunning open-concept great room off the foyer, formal living room & separate private dining room, spacious family room, & a renovated chef's kitchen (2018) with premium appliances, quartz counters, a large island, breakfast bar & bright breakfast area with walkout to the backyard. Upstairs is a generous laundry room, 4 spacious bedrooms, (4th bedroom currently used as den but can be converted to 4th bedroom) & 3 full bathrooms, including a luxurious primary suite with cathedral-style ceilings, a fireplace, & a renovated 6-piece ensuite (2015). The professionally finished basement features a home theatre, recreation/games room, wet bar, gym & 3-piece bathroom. Additional updates include a new pergola & awning (2024), furnace, air conditioner, & renovated kitchen (2018), re-shingled roof & renovated ensuite bathroom (2015).

70 Shorewood Place, Oakville

$8,999,999

W13578934 MLS

Prime investment opportunity! Approximately 17,732 sq. ft. freestanding commercial building on a large corner lot in a highly desirable Oakville location. Fully leased and currently operating as a restaurant, banquet hall and lounge, offering immediate income potential. Excellent visibility, ample parking, and convenient access to the QEW, Highway 403 and Highway 407. A rare opportunity to own a high-profile commercial asset with strong long-term investment potential.

2273 Royal Windsor Drive, Oakville

$6,599,000

5 Beds ⋅ 7 Baths ⋅ W13569686 MLS

Set on an oversized 100' 170' estate lot in Morrison, one of Oakville's most established neighbourhoods, this custom-built residence offers approximately 7,800 sq. ft. of finished living space, including a walk-out lower level designed for elegant entertaining and comfortable family living.A dramatic two-storey foyer introduces expansive principal rooms with soaring ceilings, oversized windows, and custom millwork throughout. The chef-inspired kitchen features premium appliances, custom cabinetry, a walk-in pantry, wine cellar, and a large centre island, flowing seamlessly into the breakfast area and family room. Sliding glass doors open to a covered patio with a built-in BBQ, generous dining area, and separate lounge. Formal living and dining rooms, a private office, and well-planned service areas complete the main level.The second floor is highlighted by a luxurious primary suite with a custom dressing room, spa-inspired ensuite, and private balcony overlooking the landscaped grounds. Three additional spacious bedrooms each offer ensuite access and walk-in closets, providing exceptional comfort and privacy.The professionally finished walk-out lower level includes a fitness area, games room, media room, playroom, and a fifth bedroom for guests or extended family. Large windows and direct backyard access create abundant natural light and seamless indoor-outdoor living.The private backyard is surrounded by mature trees and professionally landscaped grounds, featuring a resort-inspired swimming pool, covered outdoor living area, and multiple spaces for entertaining and relaxation.Ideally located close to Lake Ontario, downtown Oakville, top-rated public and private schools, shopping, community centres, parks, and a full range of local amenities.

265 Maple Grove Drive, Oakville

$18,500,000

W13565890 MLS

Rare opportunity to acquire a well-maintained 43,074 sq ft freestanding industrial facility in the highly sought-after Winston Business Park. Located on 2.5 acres at the Oakville/Mississauga border, the property offers excellent access to Highways 401, 403 407 and the QEW. Built in 2008, the building features 26' clear height, 4 truck level doors, 1 drive-in door, and ample employee parking (1:1,000 ratio). Zoning permits a variety of industrial uses. Ideally located within an established employment node with access to public transit, labour pools, and numerous nearby amenities.

2300 Winston Park Drive, Oakville

$9,500,000

W13562054 MLS

A rare opportunity to acquire a premier downtown Oakville redevelopment asset, ideally positioned for an owner-occupier, investor, or long-term landholder. Occupying 0.58 acres at the high-profile southwest corner of Lakeshore Road West and Kerr Street, just moments from Lake Ontario, this single-tenant property combines exceptional location fundamentals with strong income potential and significant mixed-use redevelopment upside. A new roof was installed in late 2025, and the property further benefits from a filed and acknowledged Record of Site Condition, offering added confidence for sophisticated purchasers and future planning initiatives. Nearby precedent at 42 Lakeshore Road West, two blocks east at Lakeshore Road West and Chisholm Street, further supports the area's intensification trajectory; on the same lot size, the Ontario Land Tribunal approved an 11-storey mixed-use development comprising approximately 142,300 square feet of total gross floor area, 152 residential units, and ground-floor commercial/retail space. Together, the comparable scale, location, and approval history reinforce the subject property's compelling future redevelopment potential. Please refer to the attachment for a comprehensive list of permitted uses under the title "CBD".

104 Kerr Street, Oakville

$6,250,000

5 Beds ⋅ 7 Baths ⋅ W13558096 MLS

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.

1102 Crestview Street, Oakville

$6,788,999

4 Beds ⋅ 7 Baths ⋅ W13549918 MLS

A Rare Executive gated 1.39-acre ravine estate in Morrison sought after community timeless elegance meets modern luxury this residence provides unmatched privacy, lush landscaping, & refined outdoor living. Through the custom 8-foot beveled glass entry doors, the soaring foyer sets the tone with emerald pearl granite floors, a handcrafted Austrian crystal chandelier on motorized lift, & a sweeping French Provincial staircase with wool Victorian Tapestry runner. The main floor boasts elegant formal living & dining rooms with hand-carved marble fireplaces, cathedral ceilings, plaster mouldings, & Palladian windows framing ravine views. A richly appointed library & office feature maple plank flooring, crown moulding, & custom draperies. The family room offers panoramic vistas & a mahogany fireplace, while the chefs Hawthorne kitchen impresses with cherry cabinetry, granite surfaces, premium appliances, & a walkout to the terrace. Upstairs, the luxurious primary suite includes a two-way fireplace, custom lighting, & a walk-in closet with attic access. The spa-inspired ensuite offers heated floors, Jacuzzi air tub, granite shower, & Strass crystal lighting. Three additional bedrooms each enjoy private ensuites, cathedral ceilings, & custom finishes. A versatile great room with terrace access & a full laundry suite complete this level. The lower level is an entertainers dream with a billiards & games room, full walnut bar, gym, media lounge, & spa retreat with sauna & steam shower. Radiant heated floors, & abundant storage enhance the space. Outdoors, the property is equally breathtaking with two stone gazebos joined by a large pergola, extensive walking paths, & a serene koi pond and a Japanese-inspired garden creating a private resort-like escape. With 4+1 bedrooms, 7 bathrooms, elevator access to all levels, multiple terraces, & a gated circular driveway, this estate offers over 10,000 sq. ft. of refined living in one of Oakville's most coveted neighbourhoods.

1024 Linbrook Road, Oakville

$5,888,000

5 Beds ⋅ 6 Baths ⋅ W13533014 MLS

Nestled within one of Oakville's esteemed neighborhoods, this exceptional residence epitomizes luxury living. Boasting proximity to the lake, renowned schools, tennis courts, parks, and various amenities, this property offers a blend of convenience and exclusivity. Upon entering, guests are welcomed by an exquisite interior spanning over 5,000 square feet of above-grade living space. The detached home showcases a distinctive architectural design and impeccable artisanship, radiating elegance. Crafted to emulate a lavish retreat, the residence features an array of amenities including an in-ground pool, hot tub, backyard putting green, a meticulously landscaped outdoor area complete with a bathroom and shower. Inside this dream showhome offers ample space for entertaining. In the kitchen, grey-blue cabinets with black uppers pair beautifully with a sleek quartz countertop and backsplash for a modern industrial look. A two-storey hallway connects the kitchen to the rest of the main floor and offers drama of its own with rich velvet drapes and a series of French doors. Enjoy this one of a kind basement including a bowling alley, a gym room, open-concept media room and a 5th guest bedroom. Luxury Certified.

393 Maple Grove Drive, Oakville

$12,000,000

6 Beds ⋅ 10 Baths ⋅ W13475920 MLS

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.

113 Maple Grove Drive, Oakville

$6,095,000

5 Beds ⋅ 6 Baths ⋅ W13471308 MLS

Set on a rare 130' x 130' lot in the heart of Southeast Oakville, 240 Poplar Drive offers approximately 6,900 sq. ft. of finished living space on one of the area's most desirable streets.Designed by Bill Hicks, this custom home features generous principal rooms, a highly functional family layout and exceptional outdoor living. The private backyard includes mature landscaping, extensive stonework, an in-ground pool with waterfall, integrated hot tub, landscape lighting, a dedicated pool equipment house and multiple outdoor entertaining areas.The home has benefited from ongoing updates and improvements throughout ownership, including hardwood flooring, décor, landscaping and pool improvements, mechanical upgrades and integrated technology.The upper level offers spacious family accommodation highlighted by a private primary suite with steam shower ensuite. The fully finished lower level provides flexible space for recreation, fitness, hobbies, entertaining and guest accommodation.Located within walking distance of downtown Oakville, Lake Ontario, parks, restaurants, boutiques and some of Ontario's top-ranked schools, this is a rare opportunity to acquire a family home on an exceptional lot in one of Oakville's most established neighbourhoods.Large lots, mature trees and this level of privacy are increasingly difficult to find in Southeast Oakville. 240 Poplar Drive offers a rare combination of space, privacy and walkability in a premier South Oakville location.

240 Poplar Drive, Oakville

$11,999,000

W13453338 MLS

A rare and exceptional land opportunity on prestigious Lakeshore Road East! 1475 Lakeshore Rd E offers scale and long-term potential in one of Oakville's most established and coveted lakefront-adjacent corridors. Zoned RL1-0, the property presents a compelling opportunity for thoughtful redevelopment in a neighbourhood defined by multi-million-dollar estates and enduring value. With its impressive acreage, this site presents a great opportunity to rezone to permit a condominium roadway with 7 to 8 freehold houses. Alternatively, the property could accommodate a single magnificent custom estate. Other opportunities exist through this rare offering! Conveniently located just moments from Lake Ontario with immediate access to the Waterfront Trail and Coronation Park, close to Bronte Harbour, downtown Oakville, GO Transit, and easy QEW access. The surrounding area features top-rated schools and premium amenities. With opportunities along this stretch of Lakeshore becoming increasingly scarce, properties of this scale represent enduring land assets. An ideal opportunity for experienced developers, custom builders, or vision-driven purchasers seeking a prime Oakville address with long-term value in an irreplaceable lakefront setting.

1475 Lakeshore Road E, Oakville

$5,999,900

3 Beds ⋅ 4 Baths ⋅ W13453644 MLS ⋅ The Randall Residences BLDG.

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

300 Randall Street Unit PH1, Oakville

$33,000,000

7 Beds ⋅ 13 Baths ⋅ W13453124 MLS

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. Two laundry rooms .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.

2054 Lakeshore Road E, Oakville

$10,880,000

5 Beds ⋅ 7 Baths ⋅ W13448452 MLS

Set on one of Morrison's most coveted streets, this extraordinary custom-built estate offers over 10,800 sq ft of impeccably designed living space, complemented by a remarkable 3,400 sq ft two-level garage and showroom with accommodation for up to 10 vehicles. A striking stone façade introduces interiors defined by exceptional craftsmanship, soaring ceilings, expansive principal rooms, and walls of glass that seamlessly connect to the resort-inspired grounds. Designed for both grand-scale entertaining and refined family living, the main level features elegant formal living and dining rooms, a private executive office, and a spectacular chef's kitchen with bespoke cabinetry, premium appliances, an oversized island, walk-in pantry, and full servery. The adjoining family room and Muskoka-inspired lounge create an effortless indoor-outdoor lifestyle experience. The upper level is anchored by a luxurious primary retreat featuring a private balcony, fireplace, custom dressing rooms, and a spa-inspired ensuite. Additional bedroom suites offer exceptional comfort with custom finishes, walk-in closets, and ensuite bathrooms. The lower level is dedicated to recreation and wellness, featuring a state-of-the-art home theatre, games area, fitness studio, sauna, custom bar, wine display room, and expansive entertainment spaces. Outdoors, the estate transforms into a private resort oasis, featuring meticulously landscaped grounds, extensive entertaining terraces, and a spectacular pool setting that offers complete privacy and tranquility. Located in one of Oakville's most prestigious neighbourhoods, this exceptional residence is moments from top-ranked schools, downtown Oakville, lakefront parks, private clubs, and all the amenities that define this premier community. A truly remarkable family estate where architectural excellence, luxury, and lifestyle converge.

262 Maple Grove Drive, Oakville

$7,470,000

5 Beds ⋅ 7 Baths ⋅ W13429066 MLS

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. Luxury Certified.

129 WOLFDALE Avenue, Oakville

$10,900,000

5 Beds ⋅ 5 Baths ⋅ W13430514 MLS

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.

350 King Street, Oakville

$5,399,000

5 Beds ⋅ 7 Baths ⋅ W13419574 MLS

Discover luxury living in this exquisite custom-built home, nestled on a prestigious street in South Oakville. This opulent residence boasts an impressive 6,212 sq ft above grade, w/ over 9,000 sq ft of finished living space and elevator, perfect for both family life & entertaining. Step inside to find a thoughtfully designed floor plan featuring 10 ceilings on the main, upper & lower levels. The main floor showcases a separate living room, formal dining room, & home office. The heart of the home is the great room, complete w/ a fireplace flanked by custom built-ins, seamlessly flowing into the gourmet kitchen & breakfast area. Culinary enthusiasts will appreciate the atmosphere with a walk-in pantry, while side door lead to a covered terrace perfect for al fresco dining and relaxation. Ascend to the upper level, where you'll find the primary bedroom suite, a true sanctuary. The spa-like bathroom features a freestanding jacuzzi and a large shower with a steamer. Three additional bedrooms, each with their own ensuite and walk-in closet, ensure privacy and comfort for family and guests alike. The lower level extends the living and entertaining space with a recreation room, wine room, wet bar, home theatre, sauna, exercise room and additional bedroom with ensuites. Outside, the expansive rear yard is adorned with perennials and mature trees and swimming pool, creating a private oasis. this home offers the perfect blend of luxury and convenience. With easy access to the GO train and major highways, it's ideal for commuters. Experience the epitome of opulent living in this remarkable residence that seamlessly combines everyday family comfort with exceptional entertaining spaces. Approximately 80% of construction completed. Property Tax is not assessed yet

581 Maplehurst Avenue, Oakville

$8,999,999

W13237504 MLS

Rare opportunity to own a building right on Trafalgar in Downtown Oakville. Already passed approval to build up to 6 stories! Amazing future development site ready to go! New leases in place on some units at proper market rents. When fully leased over a 6% cap rate.

115 Trafalgar Road, Oakville

$5,998,000

7 Beds ⋅ 8 Baths ⋅ W13215324 MLS

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.

2096 Lakeshore Road E, Oakville

$9,572,200

6 Baths ⋅ W13149470 MLS

Very well-maintained free-standing building in the heart of Oakville, offering an ideal location to expand or establish a presence in the area. The building is situated on a generous lot, providing plenty of parking, as well as the ability to accommodate 53 ft trailers. Convenient access to major highways and transportation routes, Bronte GOstation is just a short walk. The property also has future residential redevelopment potential, making it a prime investment opportunity. Inside, the existing racking system can be purchased from the current tenant, there is ample power (1200 Amps), and the office and warehouse is fully air-conditioned and sprinklered throughout.

2240 Speers Road W, Oakville

$6,499,000

5 Beds ⋅ 8 Baths ⋅ W13080708 MLS

Welcome to this resplendent custom-built masterpiece in Southeast Oakville, where flawless contemporary design meets the serenity of lakeside living. Steps from scenic parks and every desired amenity, this home offers over 7,400 SF of exquisitely curated living space designed for those who appreciate sophistication and comfort in equal measure.From the moment you enter, the open-concept layout invites a seamless flow between elegant entertaining and relaxed everyday living. The chef's kitchen, anchored by a grand Caesarstone island and outfitted with premium Miele appliances, effortlessly connects to the dining area, perfect for hosting intimate dinners or grand celebrations. Wine enthusiasts will delight in the temperature-controlled 648-bottle cellar, while the floor-to-ceiling double-sided fireplace brings warmth. The primary suite is a private sanctuary, complete with a serene balcony, a designer walk-in closet, and a spa-inspired ensuite featuring heated floors and a double-sided fireplace. Three additional bedrooms, each with their own ensuites, ensure every guest enjoys comfort and privacy. The lower level offers a full lifestyle experience, featuring a nanny suite, fitness area, sauna, wet bar, and a spacious recreation room with a walk-up to the entertainer's backyard. Step outside to a resort-like setting with a heated inground pool, hot tub, outdoor BBQ station, and pool house, all designed for effortless entertaining year-round. Additional highlights include White Oak hardwood flooring, porcelain tiles, LED lighting, built-in speakers, and a heated driveway. This home is a true testament to craftsmanship and thoughtful design.

112 Elton Park Road, Oakville

$10,650,000

W13054176 MLS

Prominent freestand industrial building situated on a 2.54 acre lot with extra land permitting outside storage. Highly attractive corner lot emphasizes ample parking, fenced yard, multiple points of ingress/egress, with a phenomenal location to major highways for quick access. The building features 3 oversized drive-in doors and 21' clear height with a clean white boxed warehouse. Extremely well-maintained, the warehouse showcases polished concrete floors, and efficient LED lighting. The property has undertaken many recent upgrades to the office and shows beautifully.

860 Progress Court, Oakville

$6,459,000

5 Beds ⋅ 8 Baths ⋅ W13050914 MLS

This Incredibly Keeren Designed Home Built In 2022! Located In Prestigious Eastlake Neighbourhood. This Home Boasts Approx.6300sf Luxury Living Space! Featuring Top-Notch Architectural Refinements With 4+1 Bdrms, 8 Baths (6 Full, 2 Half). Exterior Facade And Walk-up Area Built With Indiana Stone From The United States, Pella Windows And Doors, 71/2"*3/4 Grandeur White Oak Colour Engineered Hardwood Floor Through Out.The First Floor Boasts 10' Ceiling, A Double-Height Entry W/A Chandelier Lift/Down/W/A Skylight. Spacious Main Flr Office Perfect For Working From Home. The Great Rm Area Includes A Cozy Gas Fireplace, Breathtaking Views Of the Stunning Backyard Pool. Kitchen Equipped With B/I High-end Wolf Gas Stove & Hood, B/I Miele 30'' Fridge, Freezer, Oven & Micro, 2 B/I Asko Dishwashers And 24" Marvel Wine Fridge. A Lg 60* 91 Centre Island, Marble Calacatta Porceline Countertop And Backsplash, Ample Upper & Lower Cabinetry Space.The Interior Showcases Detailed Trim Work, Plaster Crown Molding, A Motorized Blinds System On Main Flr And Master Bdrm, Heated Floors In The Basement And All Ensuite Upstairs. Massive Windows Flooding Every Space With Light. The 2nd Floor Offers 4 Luxurious Bdrms, Each With Its Own Ensuite And W.I.C. Primary Bdrm W/A Lg Dress Rm W/A Skylight & Elegant 5pc Ensuite. The Residence Is Further Equipped With 2 Carrier Air Conditioning Units and 2 Furnaces W/Humidifiers. The Basement Includes A Guest Bdrm W/Ensuite, Rec, Home Theatre, Gym & Glass-enclosed Wine Rm. Designed Landscaping At Front & Backyard. The Fully Fenced Rear Yard Is A True Oasis W/Salterwater Pool W/Waterfall, An Outdoor Covered Porch W/Stone Gas Fireplace & BBQ Area. Irrigation System, Security System W/HD Outdoor Cameras, An Indoor Sound System And Google Home Automation. Six Routers Allow Network Signal Transmitted Within Entire House. HWT Owned. Walking Distance To Town, Parks & The Lake. OT High School, Maple Grove, Ej James, St. Mildreds, Linbrook, Appleby, Maclachlan.

172 Burgundy Drive, Oakville

$23,980,000

5 Beds ⋅ 8 Baths ⋅ W13030806 MLS

Welcome to 489 Lakeshore Road East, a truly exceptional estate crafted by the renowned Ferris Rafauli, nestled in the prestigious enclave of southeast Oakville along the serene shores of Lake Ontario. This rare one-acre property boasts a remarkable 18,000+ square foot steel-frame home, meticulously designed to showcase unparalleled craftsmanship and timeless elegance. Every detail of this exquisite residence speaks to a dedication to luxury living, from its concrete structure to its five bedrooms and eight baths, eight fireplaces, three kitchens, and elevator for seamless access to all levels. Indulge in the ultimate relaxation with amenities such as an indoor pool, built-in spa, dry sauna, and cabana with a full kitchen. The property also features a four-car garage, 600-amp electrical service, in-floor heating, and cutting-edge building operation systems, all complemented by award-winning landscaping that surrounds this magnificent estate. For the discerning buyer seeking the epitome of luxury living, 489 Lakeshore Road East offers an unparalleled opportunity to experience a lifestyle of opulence and refinement.

489 Lakeshore Road E, Oakville

$12,500,000

W13018654 MLS

Zoning approved for ancillary outside storage/ processing. Serviced land. Adjacent to approved spec industrial multiples. Close proximity to major highways (QEW, 403, 407). Fronts Hwy 407, just west of Western Business Park in Mississauga and 403/ 407 Interchange. Up to 180,000 sf of single building or multiple divisions, or small building with outside storage/ parking. Current development application (second submission) available online at: https://www.oakville.ca/business-development/planning-development/active-development-applications/ward-7-development-and-site-plan-applications/east-west-inc-4243-sixth-line-z-1215-06/

4243 Sixth Line, Oakville

$7,900,000

6 Beds ⋅ 8 Baths ⋅ W12919550 MLS

Located on the prestigious private lane of Lambert Common this masterful 8300 square foot plus home includes a seamless 2024 addition from the original 7 year old build. This custom residential design stuns with grand proportions and meticulous detail. All three levels feature 10-foot ceilings defining the home by its impressive rooms and an atmosphere of space and luxury. The entrance is both welcoming and breathtaking with it's incredible moldings and crystal chandelier casting diamond glints across the foyer flanked by the living and dining rooms. Stepping through to the back of the house, you will enjoy panoramic views of wall to wall glass overlooking the two heated patios. The culinary wing is divided into two distinct zones for the ultimate hosting experience: The Showcase Kitchen: A visual centerpiece featuring a dramatic backlit stone wall that serves as a piece of living art. A 14-foot island, elegantly underlit to create a feeling of light providing sophisticated seating for six to enjoy the stunning kitchen. The Prep Kitchen: Positioned discreetly at the back of the main floor, this secondary kitchen allows for preparation to remain out of sight, ensuring the primary living space remains pristine. The home boasts five bedrooms with walk-in closets and ensuites. The Primary Suite is a dedicated sanctuary with his & hers walk-in closets, fireplace, and private bath, all oriented specifically to provide a serene, view of the lake, allowing the water to serve as a constant, tranquil backdrop. The upper level laundry room is spectacular an appliance package that includes a steam closet. The Entertainment & Wellness Lower Level Maintaining the same 10-foot ceiling height as the upper floors, and a destination unto itself. This level is fully equipped for a high-performance lifestyle, featuring and private glass enclosed gym, theatre room, open recreation room, secondary laundry suite & sixth bedroom with private office. This home is Luxury Certified.

15 LAMBERT Common, Oakville

$6,999,900

6 Beds ⋅ 7 Baths ⋅ W12871004 MLS

Crafted as the personal residence of a renowned designer, this 5+1 bedroom, 10,000+ sq.ft. waterfront estate is a rare offering in one of Bronte's most coveted settings. While neighbouring homes were also designed by him, none compare to the scale, craftsmanship, and artistry dedicated to this residence-his own masterpiece. Expansive windows and soaring ceilings flood the home with natural light, framing breathtaking lake views on every level. Multiple balconies and terraces offer front-row views of sunrises, sunsets, and moonlit water-creating a seamless connection to nature from morning to night. Thoughtfully designed for both family living and elegant entertaining, the main level features grand principal rooms, multiple gas fireplaces, formal and informal living spaces, and a gourmet kitchen with walkout to the lakeside terrace. Each level offers outdoor retreats - private balconies off bedrooms, and expansive terraces perfect for gatherings. The upper level includes generously sized bedrooms, including a luxurious primary suite with private balcony, spa-like ensuite, and unobstructed views of the lake. A full lower level adds an additional bedroom, recreation spaces, gym, and walkout access. Set on a quiet street with a strong sense of community, this home offers a rare blend of privacy and connection. The saltwater pool, manicured grounds, and lakeside setting make every day feel like a peaceful escape. Minutes to Bronte Harbour, boutique shops, trails, parks, and top-rated schools-this residence is more than a home; it is a lifestyle on the water.

3206 Shoreline Drive, Oakville

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