Refine Search
Sort by
$3,250,000
5 Beds 6 Baths W13771750 MLS
EXCEPTIONAL RIVER OAKS RETREAT WITH A PRIVATE BACKYARD OASIS BACKING ONTO LIONS VALLEY PARK AND SIXTEEN MILE CREEK! RARE THREE CAR GARAGE! Situated on a quiet cul-de-sac, this impressive residence delivers an exceptional lifestyle where everyday living feels like a private resort. The professionally landscaped backyard is the showpiece, featuring an inground pool framed by a natural stone surround, raised TimberTech composite deck (2020), lush gardens, mature trees, and towering cedars creating an extraordinary sense of privacy. With direct access to Lions Valley Park and Sixteen Mile Creek, this is a spectacular setting for summer entertaining, poolside gatherings, outdoor dining, and relaxed family living. Inside, the main level offers a living room with soaring 18' decorative ceiling and gas fireplace, elegant dining room, den with vaulted ceiling, and a dedicated home office. The stunning gourmet kitchen features refinished maple cabinetry (2019), granite countertops, stainless steel appliances, pantry, centre island, and bright breakfast area with built-in dining table and walkout to deck. The primary bedroom offers two walk-in closets and a five-piece ensuite renovated in 2025 with a glass shower, dual sinks, and dual toilets. The professionally finished walkout lower level offers excellent potential for an in-law or nanny suite. Highlights include 9' ceilings throughout all three levels, hardwood staircase (2025), windows (2019), front and back doors (2015), furnace and central air (2020), roof replacement with an outdoor heating element on lower roof (2015), inground sprinkler, and incredible curb appeal with an attractive stone and brick exterior. Close to trails, Sixteen Mile Sports Complex, private schools, shopping, restaurants, Glen Abbey Golf Club, transit, highways, and GO Train. A rare opportunity to enjoy exceptional family living, a resort-inspired backyard, and a remarkable sense of privacy in one of River Oaks' most coveted settings.

1036 Valley Crest Circle, Oakville

$2,358,000
6 Beds 6 Baths W13771166 MLS
NOT A COOKIE CUTTER HOME. .ONE OWNER HOME... Welcome to 3338 Fox Run Circle-where success feels right at home. Modified Builder's Plans! Spacious 2 storey; Main floor boasts of 9ft ceiling with gleaming hardwood floors. Generous 5 bedrooms on 2nd floor. Circular staircase on 3 levels. THIS ISN'T JUST A HOME IT'S A STATEMENT. Nestled on one of Oakville's most desirable streets in LAKESHORE WOODS, this exceptional residence is designed for those who appreciate quality, success, and lifestyle. Elegant spaces that impress guests yet feel effortlessly comfortable, reflecting pride of ownership and every detail enhances daily living. Whether you're entertaining in style, enjoying quiet evenings with family, or simply taking pride in owning a home that stands above the rest, this is where your next chapter begins. LAKESHORE WOODS is close to top-rated schools, APPLEBY COLLEGE, SHELL PARK, NEWLY DEVELOPED BEACHES, TRAILS. You'll enjoy the perfect balance of prestige and convenience. Featuring a 3 car tandem garage. Extended driveway to accomodate another 3 car parking. NO KITEC PLUMBING. New Costco now under construction.

3338 Fox Run Circle, 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

$2,098,800
6 Beds 6 Baths W13770214 MLS
Stunning Extensively updated sun-filled home in Prestigious Lakeshore Woods in Oakville on a Premium corner lot with extra wide frontage. Withsolid brick exterior and Custom double front door, this home welcomes you into a bright and inviting main floor. It offers 3301sqft (abovegrade)& 1534 sqft (basement)of Elegant livings pace. Formal spacious living room , Separate Dining room, Gourmet Chefs Kitchen with Amplestorage, a grand peninsula island with seating, Stainless steel appliances including a gas stove, built-in microwave, and oven. Family Roomboasts a Cathedral Ceiling with Soaring Windows, built-in cabinetry including a two-sided gas fireplace shared with the main floor office. ModernLaundry room with new washer/dryer and a bench. 2nd Floor features An expansive primary bedroom with new TV cabinets and closets, Walk-incloset, and luxurious 5-piece ensuite, plus three additional spacious bedrooms each with ensuite. Fully Finished Basement Includes twobedrooms with ensuites, a large recreation area, a separate kitchen, laundry room, and an additional 2-piece bathroom. Imported light fixtures,new engineered hardwood floors through out (2026).With a double-car garage and an extra wide driveway for 3 cars, this home provides ampleparking. Professionally completed interlocking at front, backyard and side yard. The backyard and side yard is your dream outdoor space withbeautiful trees, new grasses (2025), new gazebo (2025), standard size badminton court (2025), lots of space to add your dream features(sunroom, outdoor kitchen, shed, etc). A rare find large lot in Lakeshore Woods (6200 sqft). Great location, close to highway, schools, shoppingcenters, walking distance to trails, parks (shell park, nautical park, village wood park, shell park dog parks, and beach at south shell park.

238 Nautical Boulevard, Oakville

$3,359,000
5 Beds 6 Baths W13765006 MLS
Welcome to this exceptional custom-built residence where luxury, comfort, and thoughtful design come together. Offering 4+1 spacious bedrooms, 5 full bathrooms, and a convenient main-floor powder room, this home is perfectly suited for both family living and entertaining. The heart of the home features a stunning chef's kitchen equipped with premium JennAir appliances, including a sleek induction cooktop, blending style and performance for everyday cooking and special occasions alike. Designed for year-round comfort, the home includes forced-air heating, central air conditioning, a tankless water heater, and a central vacuum system. The primary ensuite provides a spa-like retreat with a luxurious heated bathroom floor, while the fully finished basement features radiant heated floors for added warmth and comfort. Step outside to your own private backyard oasis featuring a heated saltwater pool, underground sprinkler system, and a covered rear porch-perfect for relaxing or entertaining throughout the seasons.Additional premium features include vinyl windows, custom remote-controlled blinds, and a double-car custom-finished garage complete with built-in storage and remote door openers. A rare combination of elegance, efficiency, and modern convenience, this outstanding property offers an elevated lifestyle in every detail.

1189 Tisdale Street, Oakville

$4,150,000
4 Beds 6 Baths W13761512 MLS
A reimagined historic farmhouse that blends timeless architectural charm with warm natural finishes and a soft colour palette. This heritage home offers over 7,000 square feet of luxury living space, where timeless character and sophisticated modern design come together seamlessly. Every detail, from the craftsmanship to the carefully curated finishes, has been completed to an exceptional standard. Elegant design elements include wide oak plank flooring, black accent hardware, shiplap detailing, and a striking open staircase with tempered glass railings. The chef-inspired kitchen is designed for both everyday living and entertaining, featuring professional-grade appliances, a large centre island, custom cabinetry, and quartz countertops. The kitchen flows seamlessly into the oversized great room highlighted by expansive architectural Kolbe windows, a coffered ceiling, and a dramatic five-foot gas linear fireplace with a steel surround. Automated blinds and lighting enhance the main floor living ares. A separate living room offers inlaid herringbone oak flooring and access to the wraparound covered verandah. Upstairs, the impressive hallway showcases 14-foot ceilings and oversized skylights, leading to four spacious bedrooms, each with a private ensuite featuring heated floors. The primary retreat includes a generous walk-in dressing room and a spa-inspired five-piece ensuite complete with a freestanding tub, double vanity, heated porcelain floors, heated towel rack, and glass enclosed walk-in shower. The fully finished lower level offers a spacious recreation area with 9-foot ceilings, home gym area, wet bar, 3-piece bathroom, and roughed-in theatre room. Additional highlights include a centrally heated garage equipped with two EV chargers. Outside, the beautifully landscaped property features perennial gardens, a covered terrace, and a circular driveway. Ideally located across from Appleby College, a short walk to the lake and moments from downtown Oakville.

489 Lakeshore Road W, Oakville

$2,790,000
5 Beds 6 Baths W13761278 MLS
On rare occasion, a truly exceptional residence becomes available in Oakville.Situated mere steps from two of the provinces most respected elementary and secondary schools, and minutes from Appleby College, one of the worlds most distinguished private institutions, 370 Christina Drive is nestled on a serene, tree-lined street in a coveted postal code once defined by Environics as Wealthy and Wise. Just moments from the shimmering shores of Lake Ontario, the boutique allure of Kerr Street Village, and one of the most picturesque and desirable downtowns in all of Ontario, this is more than a home, it is a lifestyle reserved for the discerning few. Designed by award-winning architect, Neil MacDonald, this custom-built 4+1 bedroom home offers 4,922 of liveable sqft and is the perfect blend of sophistication and low-maintenance luxury. Ideal for families seeking room to grow or downsizers looking for elegance without compromise. A rare and highly desirable main floor primary suite with walk-out access to the professionally landscaped backyard offers a sense of tranquility and privacy rarely found, making it ideal for both families and down-sizers. The heart of the home is a sun-drenched open concept kitchen and family room, anchored by a cozy gas fireplace - perfect for everyday living and entertaining. A spacious formal dining room adds elegance for special gatherings, while a dedicated main floor office offers the perfect work-from-home solution. Upstairs are three generously sized bedrooms and two full bathrooms, providing ample space for children or guests. Each room is thoughtfully appointed to offer both comfort and function. Step outside to a meticulously landscaped backyard oasis designed for effortless enjoyment. Featuring "Tuff Turf" artificial grass, low-maintenance foliage, and a state-of-the-art outdoor kitchen complete with a built-in barbecue, breakfast griddle, and stone countertop - this space is the premiere backyard to host this summer! Welcome home.

370 Christina Drive, 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

$4,898,000
5 Beds 7 Baths W13754410 MLS
Tucked away on a private road, south of Lakeshore, neighbouring distinguished Appleby College, The Enclave offers a blend of luxury, privacy, & timeless design in one of Oakville's most coveted neighbourhoods. Situated on the largest of only 5 lots of unparallelled privacy. Flanked to the west is Appleby College's soccer fields, and putting green to the south. Showcasing over 6,800sqft of exquisitely finished living space w 10' ceilings on all levels. Extensive custom millwork, & intricate wall panelling create an atmosphere of sophistication throughout. Custom 'Top Notch' Cabinetry features a 13ft island w walnut base, 2 dishwashers, 6 burner gas range with 2 ovens, & built-in work space for studies. 2nd lvl is anchored by an impressive primary retreat featuring a spacious walk-in dressing room and a luxurious spa-inspired ensuite. Three additional generously proportioned bedrooms, each appointed with their own private ensuite bathroom, provide exceptional comfort & privacy for family and guests alike. fully finished lwr lvl is the perfect extension of the home's luxurious living space & features in-floor heating, a spacious 5th bdrm/office w custom built-in shelving w/a private ensuite, a dedicated theatre room, an expansive games and entertainment area with pool table and wet bar, & a striking glass-enclosed fitness studio. Outside, a resort-inspired backyard oasis awaits. Professionally landscaped gardens surround a Gibsan swimming pool, while multiple outdoor living spaces provide the perfect setting for relaxation and entertaining. Enjoy summer evenings beneath the covered flagstone terrace featuring an outdoor television, gas BBQ, and elegant dining area. Perfectly enveloped by one of Canada's most prestigious educational institutions, the lake, downtown Oakville, renowned dining, boutique shopping, and waterfront trails, this exceptional residence offers a rare opportunity to experience luxury living at its finest. This is a home that truly stands apart.

456 Lakeshore Road 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

$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

$4,250,000
4 Beds 6 Baths W13733644 MLS
Positioned on a rare 0.8-acre ravine lot in one of Southeast Oakville's most coveted neighbourhoods, this exceptional residence makes an immediate impression with its stately curb appeal and beautifully landscaped grounds. Framed by mature trees and offering exceptional privacy, the home presents a refined presence that blends seamlessly with its lush, natural surroundings. Inside, 7,000 sq. ft. of elegantly finished living space unfolds. A grand foyer sets the tone, complemented by rich hardwood flooring and soaring ceilings throughout. The home offers four spacious bedrooms, each with its own private ensuite, along with premium appliances and a custom wine cellar. A separate side entrance adds flexibility, providing a private access point with direct entry to the lower level. Designed for both elegant entertaining and relaxed everyday living, the backyard is a private resort-style retreat. A saltwater inground pool, expansive stone patio, and uninterrupted ravine views create a setting that feels more Muskoka than city. Ideally located within walking distance of Oakville's top-ranked schools and minutes from premier amenities, this home offers a rare combination of estate-scale land, striking curb appeal, and unmatched privacy in a prime urban location. Well maintained with extensive upgrades, it reflects true pride of ownership throughout.

437 Cairncroft Road, Oakville

$2,649,000
5 Beds 6 Baths W13732358 MLS
Welcome to 455 Samford Place, a remarkable custom-built luxury home in one of Southwest Oakville's most sought-after neighbourhoods.Setona premium 65' x 115' lot, this stunning residence blends sophisticated design, exceptional craftsmanship, and modern family living. Itslimestoneand stucco exterior, expansive driveway, double-car garage, and rare rear-access garage door create an impressive first impression.Step insideto bright, open-concept living with 10-foot ceilings, oversized windows, and elegant custom millwork throughout. Designed foreveryday livingand entertaining, the chef's kitchen features a large quartz island, designer lighting, premium Thermador appliances, and aconvenient spicekitchen. The family room is a true gathering space, highlighted by a dramatic floor-to-ceiling porcelain fireplace feature wall andFrench doorsopening to the private backyard for seamless indoor-outdoor living. A grand wood staircase with skylight and custom panelingleads to the upperlevel, where four spacious bedrooms each offer an ensuite and walk-in or built-in closet. The primary suite is a private retreatwith a beautifulfeature wall and spa-inspired ensuite showcasing double walnut vanities and luxurious porcelain finishes. The professionallyfinished lower leveloffers endless flexibility for entertaining, recreation, or multi-generational living, featuring a spacious rec room, secondlaundry area, stylish wetbar with sink, dishwasher, fridge, wine storage, and space for a beverage cooler. A separate walk-up to the backyardadds exceptionalconvenience and versatility. With refined finishes, premium upgrades, and an unbeatable Oakville location close to schools,parks, shopping, andthe lake, this exceptional home offers the perfect blend of luxury, comfort, and timeless elegance.

455 Samford Place, Oakville

$3,198,000
6 Beds 6 Baths W13732172 MLS
Experience uncompromising luxury in this newly built, architecturally striking residence where every detail has been meticulously curated and no expense has been spared. Designed and built by its owner-an architect-as his primary residence, this 5000 + sqfts of living space custom home reflects exceptional attention to detail and uncompromising quality throughout. From the moment you enter, the level of craftsmanship is immediately evident-featuring a sun- filled main floor office, soaring cathedral ceilings, and dramatic floor-to-ceiling triple- glazed windows and doors that flood the home with natural light. Designed for both elegance and functionality, the heart of the home is a bespoke chef's kitchen showcasing premium Miele appliances, custom cabinetry, and refined finishes, seamlessly complemented by a secondary kitchen and a fully finished lower level with matching attention to detail. The grand two-storey living space is anchored by a statement fireplace, while smart home integration enhances everyday living with built-in sound, security, and climate systems. This home is rich with high-end features, including heated flooring at the main entrance and in the primary ensuite with Wi-Fi control, an electric vehicle charger in the garage, and thoughtfully designed systems throughout. All bedrooms offer private ensuites with custom glass showers and premium fixtures, while the primary retreat provides a spa-like experience with elevated finishes and comfort. The lower level continues to impress with oversized windows allowing abundant daylight, along with a custom bar, home theatre, gym, and additional living space. It also includes a convenient secondary (backup) laundry and provisions for a full cooking kitchen, offering excellent flexibility for extended family or future use. A second-floor laundry adds everyday convenience and functionality.***

1404 Waverly Avenue SW, Oakville

$4,788,500
5 Beds 6 Baths W13730146 MLS
Introducing a truly exceptional property that redefines luxury living, elegance, and comfort! Nestled in the best location of South East Oakville, this magnificent house is a testament to sophisticated design and meticulous attention to detail. As you step into the grand foyer, you're immediately greeted by an open floor plan that seamlessly blends spaciousness and intimacy. The sprawling 7000+ square feet of living space showcases a harmonious blend of modern architecture and timeless craftsmanship, creating an atmosphere of refined opulence. The heart of this home is undoubtedly the state-of-the-art German kitchen. Equipped with the latest appliances, custom cabinetry, and high-end finishes, it's a culinary haven for the gourmet enthusiast. Whether you're entertaining guests or preparing a family meal, this kitchen is designed to elevate your culinary experience to new heights.

1286 Cambridge Drive, Oakville

$3,499,999
5 Beds 6 Baths W13727274 MLS
Welcome to 369 Wade Street, a true luxury custom family residence offering more than 5,500 square feet of refined living space, exceptional craftsmanship and an extraordinarily functional layout. Thoughtfully executed from top to bottom, the home combines impressive scale with the comfort and practicality of true family living. A massive concrete driveway creates a striking sense of arrival, while the private backyard is anchored by a pristine pool and an inviting setting for summer entertaining. Inside, the main level makes an immediate statement with soaring 10-foot ceilings, a dramatic 16-foot formal living room and a spectacular 21-foot great room that fills the principal spaces with natural light. Striking designer lighting fixtures and thoughtfully selected statement pieces throughout further elevate the home's custom aesthetic. Designed to transition effortlessly between everyday living and grand-scale entertaining, the floor plan continues with a commanding foyer, private executive office, formal dining room and an outstanding chef's kitchen showcasing extensive custom cabinetry, top-of-the-line Wolf and Sub-Zero appliances, and a bright breakfast area overlooking the pool. Upstairs, four generously sized bedrooms each enjoy 10-foot ceilings, abundant natural light, custom built-ins and their own private ensuite with heated flooring. The primary suite is elevated by beautifully executed bespoke closets with integrated LED detailing and luxurious spa-inspired ensuite, complemented by a spacious second-floor laundry room. The finished lower level adds exceptional flexibility with an expansive open-concept layout, walk-up access, a sleek bar, two additional bedrooms, a full bathroom and a separate entrance. Ideally located minutes from the QEW, Highway 407, Appleby College and downtown Oakville, 369 Wade brings together dramatic architecture, distinctive custom millwork, exceptional scale and one of the most thoughtfully designed family layouts in the area.

369 Wade Street, 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

$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

$2,549,999
6 Beds 6 Baths W13706274 MLS
Set on a coveted street in Bronte West, this 5-bedroom, 6-bathroom home is built for family life, entertaining, and complete privacy, backing directly onto greenspace with no rear neighbours in sight. For families who want room to grow without sacrificing the little details that make a house feel like home, this one delivers on every front. Inside, the open-concept kitchen anchors the main level, designed for the everyday rhythm of a busy household as much as it is for hosting, a natural gathering point for morning routines, homework at the island, and dinners with friends. The main floor also features a fully custom in-law suite, complete with its own living room, bedroom, and bathroom that opens directly to the backyard, a rare and thoughtful layout that's ideal for extended family, live-in support, or guests who deserve their own private space. Upstairs, the primary suite is a genuine retreat, offering a spa-inspired 5-piece en suite and a separate custom walk-in closet built for real storage, not just show. The remaining bedrooms give a growing family the flexibility it needs, whether that's space for kids, a home office, or a dedicated guestroom. The fully finished basement extends the living space even further, with a wet bar, fridge, dedicated laundry room, and additional crawl space for storage; every practical need is considered. Step outside, and the backyard becomes its own destination. A saltwater pool and hot tub sit alongside a separate barcabana, a custom four-season canopy for year-round enjoyment, and a custom stream that ties the whole space together. Backing onto greenspace, the setting is completely private, a rare find this close to everything Bronte has to offer. Every inch here has been designed for entertaining, unwinding, and the everyday moments that make family life good. This is a home built for families who want space, flexibility, and a backyard unlike anything else in Bronte West.

493 Tipperton Crescent, Oakville

$4,999,000
5 Beds 7 Baths W13706006 MLS
POWER OF SALE: Welcome to a true entertainer's residence - a 2023 build by Ambassador Fine Custom Homes, set on a 0.36-acre lot in one of Southwest Oakville's most coveted enclaves. Spanning 7,276 square feet across three finished levels, this estate home pairs architectural drama with impeccable craftsmanship. A 22-foot grand foyer draws you in, opening to a soaring 24-foot atrium crowned by a skylight and anchored by a sculptural circular staircase - a showpiece bathed in natural light. Radiant heated porcelain floors and near 11-foot ceilings carry that same sense of scale across the main level, complemented by a private home office, an elevator servicing all three floors, and a temperature-controlled wine cellar built for 180+ bottles. At the heart of the home, the kitchen commands attention: a 10-foot waterfall island, quartz slab backsplash, and two-toned custom cabinetry, outfitted with Wolf, Sub-Zero, and Miele appliances. It flows seamlessly into the great room and dining room - an open-concept design made for large-scale entertaining - while a tucked-away mud room, walk-in closet with custom shelving, and an elegant powder room keep daily life organized with direct access to the garage and rear yard. Upstairs, a vaulted, skylit hallway leads to a primary suite spanning the rear of the home, framed by backyard views and anchored by a spa-inspired ensuite and a skylit walk-in closet. Three additional bedrooms - each with its own ensuite - a library, and a laundry room complete the level, every space individually finished with its own character. Refined, light-filled, and built without compromise. 150 Wolfdale Avenue is a rare offering for the discerning buyer.

150 Wolfdale Avenue, Oakville

$3,298,000
5 Beds 7 Baths W13695240 MLS
A rare opportunity to own a striking custom-built contemporary home in one of Oakville's most desirable communities. Ideally located in central Oakville, just minutes from Coronation Park, the waterfront, top-rated schools, restaurants, shopping, and everyday amenities. Convenient access to the QEW, public transit, and Bronte GO Station makes commuting easy.Thoughtfully designed with modern architecture, clean lines, upscale finishes, and an abundance of natural light. Floor-to-ceiling windows and 10-foot ceilings with integrated pot lights create a bright, spacious, and inviting atmosphere. The well-planned layout offers seamless flow between the principal rooms, ideal for both everyday living and entertaining.The home features three kitchens: a main kitchen and a chef's kitchen on the main floor, plus a third kitchen in the basement. Each bedroom is generously sized and features its own ensuite bathroom and walk-in closet, offering exceptional privacy and convenience.The fully finished lower level expands the living space with a wet bar, powder room, additional bedroom with ensuite, and a large recreation area, perfect for entertaining or relaxing.The garage has been expanded by approximately 20% with City approval. The garage can accommodate 2 vehicles, with additional parking for 4 more vehicles in the driveway. A sophisticated home offering exceptional space, thoughtful design, and modern comfort in a highly sought-after Oakville location.

518 Sherin Drive, 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

$2,989,000
5 Beds 7 Baths W13692950 MLS
Custom contemporary masterpiece set on a rare, deep 150-foot lot in prime South Oakville, surrounded by prestigious multi-million-dollar estates. Spanning over 5,000 square feet of meticulously crafted total living space, this architectural home seamlessly blends European sophistication with cutting-edge modern luxury.Step inside to an breathtaking open-concept layout defined by soaring 20-foot ceilings in the grand foyer and main living room. The entire main floor features imported Italian Versace tile with integrated radiant floor heating, creating an ambiance of absolute refinement. The heart of the home is a chef-inspired gourmet kitchen equipped with dual marble islands, an extended breakfast bar, premium cabinetry, and an adjoining double-sided marble stone Dimplex fireplace with dual-mounted TV setups. A dramatic floor-to-ceiling marble waterfall feature wall serves as a stunning visual centerpiece.Ascend the architectural floating glass staircase to the second level, where you will find 4 spacious bedroom suites. Every bedroom boasts its own private heated-floor ensuite bathroom and tailored custom closet built-ins. The primary retreat offers a tranquil sanctuary featuring a private walk-out balcony and a lavish spa-like ensuite with a deep standalone soaking tub.The bright, sun-filled walk-out lower level expands your living options with 9-foot ceilings and oversized windows throughout. It includes a spacious open-concept recreation room, a 5th bedroom ideal for a nanny or guest suite, 2 additional bathrooms, and pre-plumbed rough-ins ready for a future second kitchen or custom wet bar.Located minutes from elite private schools, Oakville Harbour, downtown boutiques, fine dining, parks, and major transit routes. Uncompromising quality, world-class finishes, and an unbeatable South Oakville address!

2378 Rebecca Street, Oakville

$3,389,000
6 Beds 7 Baths W13690642 MLS
Welcome to 491 Fourth Line, an Exceptional Custom-Built Home in one of West Oakville's most sought-after neighborhoods. This residence offers over 6,152 sq. ft. of Magnificent Modern Finishes Living Space, blending timeless architecture with modern family functionality. Set on a professionally landscaped lot with circled driveway for luxury life style! the home features a fully fenced backyard, expansive fully covered patio with gas fireplace and natural Indiana-Lime Stone, and covered porch, creating the perfect outdoor living space for family gatherings and summer entertaining. Inside, soaring ceilings, 12-foot at the main floor, oversized 10-foot interior doors, and dramatic floor-to-ceiling windows fill the home with natural light. The chef-inspired kitchen with wood veneer cabinets serves as the heart of the home, featuring built-in appliances, a large centre island, double corner Bi-Folding doors to blend the exterior with the interior! butler's pantry, and separate walk-in pantry, offering exceptional storage and entertaining space. Spacious size living, dinning and family rooms wrapped by state of the art modern wall panels! The family room has16 ft ceiling height with three sided modern gas fire place, floor to ceiling window with the most fancy chandelier! As well as spacious mudroom with custom veneer closets for today's family needs. The upper level with 10 ft height ceiling offers four spacious bedrooms with their full ensuite bathrooms! As well as laundry, second furnace room and skylights for optimum level of comfort! The luxurious primary retreat features a spa-inspired ensuite complete with a free stand tub, oversized glass shower, double vanities, and walk-in closet. The professionally finished basement provides incredible additional living space with full kitchen, Gym, Theatre/Game room, two bedrooms, laundry, two washrooms, living room with gas fireplace and Bi-Folding doors at the Walk-out Basement! This is Your Dream Home!

491 Fourth Line, Oakville

$4,248,000
7 Beds 7 Baths W13685756 MLS
Welcome to 1399 Willowdown Road, an exceptional custom residence inspired by Frank Lloyd Wright's iconic Prairie designs, nestled on a spectacular ravine lot with a picturesque creek in prestigious South Oakville. Offering over 6,800 sq. ft. of beautifully finished living space, this remarkable home features 5 bedrooms upstairs plus 2 additional bedrooms in the finished lower level. The main floor impresses with soaring 10' ceilings, wide-plank oak flooring, custom millwork and an open-concept layout. At its heart is a chef-inspired kitchen with an oversized island, quartz counters, JennAir Professional Series appliances, extensive cabinetry and a butler pantry, opening to the expansive great room and breakfast area. Enjoy seamless indoor-outdoor living from the covered lanai with a fireplace and skylights overlooking the ravine. The finished lower level is designed for entertaining, featuring a dedicated home theatre, billiards and recreation areas, exercise room, 2 bedrooms and a full bathroom. Additional highlights include Lutron lighting automation, remote-controlled blinds, built-in ceiling speakers, multi-camera security, illuminated stair treads, 9' upper-level ceilings and a double garage. Just steps from Coronation Park and Lake Ontario, and minutes to top schools, shopping, dining and GO Transit. A truly rare offering combining architectural distinction, exceptional space and ravine-side privacy.

1399 WILLOWDOWN Road, Oakville

$2,999,000
4 Beds 6 Baths W13684180 MLS
Straight from the pages of a design magazine, this beautifully renovated, on-trend home offers more than 4,500 sq. ft. of thoughtfully designed living space. Tucked away on a quiet cul-de-sac in prestigious Southwest Oakville, it's just steps from Appleby College and the shores of Lake Ontario. The property is professionally landscaped by award-winning Gildermans, creating a stunning setting that perfectly complements this exceptional home.Designed for both everyday living and effortless entertaining, the main floor features a spacious formal dining room and a warm, inviting family room with a wood-burning fireplace. The stunning chef's kitchen is a true showpiece, featuring a Wolf induction cooktop, two double wall ovens, Sub-Zero refrigerator, two Miele dishwashers, two Marvel wine and beverage refrigerators, quartz countertops, and an impressive 9-foot island. The kitchen flows seamlessly into the family room, creating the perfect setting for gathering with family and friends.Upstairs, the luxurious primary suite serves as a private retreat, complete with a spa-inspired five-piece ensuite, walk-in closet, and an expansive terrace-ideal for enjoying your morning coffee or unwinding in the evening sun. This level also includes a generously sized second bedroom with its own ensuite, two additional bedrooms, a home office, a full bathroom, and a brand-new full laundry room for ultimate convenience.The finished lower level offers exceptional additional living space with a large recreation room, a second laundry room featuring a Miele washer and dryer, and a three-piece bathroom.Step outside to your own private backyard oasis, where a sparkling saltwater pool and beautifully landscaped gardens create the perfect escape. This exceptional home combines luxury, comfort, thoughtful design, and an unbeatable location-an opportunity not to be missed.

105 WHITTINGTON Place, Oakville

$7,475,000
5 Beds 7 Baths W13678660 MLS
An architectural masterpiece by renowned Gren Weis, this exceptional residence offers over 10,000 sq. ft. of luxurious living space on more than half an acre in one of Oakville's most desirable lake-influenced neighbourhoods. Showcasing soaring ceilings, extensive millwork, and superb craftsmanship, the home features spacious, elegant rooms and a seamless flow for entertaining. All bedrooms include ensuite baths, while the lower level impresses with a wine cellar and theatre. Outside, enjoy covered terraces, a built-in outdoor kitchen, luxury cabana, mature gardens, and a stream with bridge surrounded by landscape lighting. A classically inspired front fountain and spectacular landscaping enhance the property's distinguished presence on an important street. Close to top private and public schools, this private estate blends timeless design, quality, and sophistication in a truly remarkable setting. Luxury Certified.

1081 Argyle Drive, Oakville

$4,689,000
8 Beds 9 Baths W13673406 MLS
This exceptional property presents a unique opportunity for multi-generational living or income-generating potential with its fully self-contained in-law suite.Situated on a quiet tree-lined street in the highly sought-after Ford area,this impressive residence offers over 5,600 square feet of total living space,thoughtfully designed to accommodate a variety of modern lifestyles. The main house features 4+1 bedrooms and 5 baths.Step into the double-height foyer, where a statement chandelier sets the tone for the sophisticated interiors and open concept main living area with separate office area.The heart of the home is a custom-designed chef's kitchen,outfitted with premium Wolf and Sub-Zero built-in appliances,incl a beverage fridge. An oversized island,wide plank oak hardwood flooring,high-end lighting, and a spacious main floor laundry/mudroom with abundant storage complete the refined main level. Floating stairs lead you to the 2nd level.The principal bedroom features a walk in closet and 5pc spa like ensuite.3 additional bedrooms and 2x4 pc bathrooms offer comfort and privacy.The finished lower level includes an additional 5th bedroom,recreation space, a 4pc bathroom, & rough-in home theatre area. Connected via the mudroom but also offering a private separate entrance,the second dwelling home offers 2,056+ square feet of thoughtfully appointed living space.The main floor features living/dining & kitchen area with stainless steel appliances.The 2nd level with principal bedroom,walk in closet and 5 pc ensuite.2 additional bedrooms with shared ensuite access and conventiently located laundry room completes this level.Fully finished basement with wet bar and 4-piece bath.This home is perfect for extended family or tenants. Set on a large,pool-sized lot,the backyard awaits your personal touch-ideal for creating a private outdoor retreat. Don't miss the opportunity to live in one of Oakville's great neighbourhoods! Luxury Certified.

319 Beechfield Road, Oakville

$4,349,000
5 Beds 6 Baths W13670214 MLS
Set on a premium 60-foot lot in one of Oakville's most coveted pockets, this extraordinary custom residence offers over 5,800 square feet of meticulously crafted living space that redefines modern luxury through uncompromising engineering and timeless European-inspired design. Built with insulated concrete forms (ICF) extending through the second floor, the home features high-performance European windows, extensive microcement finishes, radiant heated floors throughout-including the basement and garage-and a striking architectural cantilever staircase. Highlights include a stunning main kitchen with a separate butler's pantry, an exceptional lower-level entertainment zone complete with a custom microcement bar, walk-in wine display, and private home theatre, plus a car-enthusiast garage and a backyard featuring an approved pool permit. With an estimated completion of October 2026, the purchaser still has a rare opportunity to select and customize final finishes. A masterclass in contemporary craftsmanship, delivering an unmatched standard of refined, energy-efficient living.

1387 WAVERLY Avenue, Oakville