Oakville Real Estate | Oakville Properties between $2,000,000 and $3,000,000 for Sale

Welcome to 455 Samford Place, a remarkable custom-built luxury home in one of Southwest Oakville's most sought-after neighbourhoods. Set on a premium 65' x 115' lot, this stunning residence blends sophisticated design, exceptional craftsmanship, and modern family living. Its limestone and stucco exterior, expansive driveway, double-car garage, and rare rear-access garage door create an impressive first impression. Step inside to bright, open-concept living with 10-foot ceilings, oversized windows, and elegant custom millwork throughout. Designed for everyday living and entertaining, the chef's kitchen features a large quartz island, designer lighting, premium Thermador appliances, and a convenient spice kitchen. The family room is a true gathering space, highlighted by a dramatic floor-to-ceiling porcelain fireplace feature wall and French doors opening to the private backyard for seamless indoor-outdoor living. A grand wood staircase with skylight and custom paneling leads to the upper level, where four spacious bedrooms each offer an ensuite and walk-in or built-in closet. The primary suite is a private retreat with a beautiful feature wall and spa-inspired ensuite showcasing double walnut vanities and luxurious porcelain finishes. The professionally finished lower level offers endless flexibility for entertaining, recreation, or multi-generational living, featuring a spacious rec room, second laundry area, stylish wet bar with sink, dishwasher, fridge, wine storage, and space for a beverage cooler. A separate walk-up to the backyard adds exceptional convenience and versatility. With refined finishes, premium upgrades, and an unbeatable Oakville location close to schools, parks, shopping, and the lake, this exceptional home offers the perfect blend of luxury, comfort, and timeless elegance. (id:5764)

455 SAMFORD Place, Oakville

Listing courtesy of RE/MAX Aboutowne Realty Corp..

$2,850,000

4 Beds ⋅ 6 Baths ⋅ 40873712 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. (id:5764)

105 WHITTINGTON Place, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$2,888,000

5 Beds ⋅ 4 Baths ⋅ 40872865 MLS® #

Tucked away in prestigious Southeast Oakville, this extraordinary custom-built bungalow tells a story of timeless elegance and effortless family living. Offering 4,356 sq. ft. of beautifully crafted space on a premium lot, every corner of this home was designed for comfort, connection, and refined everyday living. Beyond the doors, a private backyard retreat and expansive deck create the perfect setting for quiet mornings, lively gatherings, and evenings under the stars. Inside, soaring 10 foot ceilings and rich hardwood floors guide you through sun-filled formal living and dining spaces, warmed by a gas fireplace and framed by grand 8-foot sliding doors. At the heart of the home, the chef-inspired kitchen invites everyone to gather, featuring granite countertops, a Bertazzoni gas stove, a charming Belfast sink, and a bright breakfast area that opens seamlessly to the deck for easy indoor outdoor living. The main-floor primary suite is a peaceful retreat of its own, complete with French doors to the deck, a spacious walk-in closet, & a spa-inspired five-piece ensuite with a clawfoot soaker tub. Two additional bedrooms on the main level offer comfort and flexibility for family or guests. Downstairs, the finished lower level extends the story with a welcoming recreation room, second gas fireplace, games area, wet bar, laundry, and two additional bedrooms ideal for extended family, guests, or a private home office setup. Car enthusiasts will appreciate the double car garage with soaring ceilings ready for a lift, along with a double-wide driveway accommodating up to six vehicles. Designed for seamless one level living, this home offers the perfect balance of luxury and practicality for families, professionals, & downsizers alike. Just moments from Oakville Trafalgar High School, Deer Run Park, and Sobeys Maple Grove, this move in-ready residence captures the best of Southeast Oakville living where sophistication, warmth and memories come together. Luxury Certified. (id:5764)

2073 DERAMORE Drive, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$2,749,000

5 Beds ⋅ 5 Baths ⋅ 40871522 MLS® #

A covered porch, stone and shingle exterior and mature gardens set the tone for this custom-built West Oakville home. With 4+1 bedrooms and 4+1 baths on a 60 × 125 ft lot, it offers generous space for family life, minutes from the lake. Inside, dark-stained wide-plank hardwood, wainscoting and crown moulding extend through the main floor, with a private office near the entrance. At the rear, the kitchen brings together full-height white Shaker cabinetry, a veined slab backsplash, a five-burner Wolf gas cooktop, two Miele built-in ovens, a paneled fridge and Miele dishwasher, walk in pantry and an island that seats four. The adjoining dining area and vaulted family room with a gas fireplace keep the main living spaces connected. A mudroom with a built-in bench, cubbies and laundry provides a practical place for daily arrivals. Sliding glass doors extend the living space to a covered patio with Phantom retractable screens, a stone outdoor fireplace, mounted TV and built-in speakers. Beyond, mature trees frame a private, fenced backyard with two raised vegetable gardens, included with the home. The upper level has four bedrooms and three full bathrooms. The primary suite includes a walk-in closet and a five-piece ensuite with heated floors and a freestanding tub. An expanded second bedroom offers its own sitting area and ensuite. Downstairs, a large rec room is complemented by a gym that could serve as an office or studio, along with a spacious nanny or in-law suite with a private bathroom and walk-in closet. An oversized storage room beneath the porch provides additional storage. The waterfront, Bronte Harbour, downtown Oakville, the YMCA, Appleby College and local schools are nearby, with GO Transit and the QEW a short drive away. From the main-floor office to the lower-level suite, the layout offers flexibility as a family’s needs change. (id:5764)

1394 WAVERLY Avenue, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$2,699,000

4 Beds ⋅ 5 Baths ⋅ 40869024 MLS® #

Welcome to 2434 Taylorwood Drive, where exceptional design is found in every detail. Owned and thoughtfully curated by an interior designer, this is a home where custom is not an upgrade, it is the standard. The main floor is defined by 10' ceilings, beautifully proportioned spaces and sophisticated finishes throughout. A formal living room and dining room set the tone, complemented by a private home office and walk-in hall closet. The expansive family room features coffered ceilings, custom built-in shelving surrounding the television, a built-in desk and an exquisite marble surround framing the gas fireplace. At the heart of the home, the chef's kitchen is designed for both everyday living and entertaining, while custom drapery, millwork and carefully considered details create a polished, cohesive feel throughout. Upstairs, four bedrooms each enjoy their own ensuite, while custom built-in closet systems provide exceptional organization. The primary suite goes well beyond the expected with a separate dressing room/sitting room that can also function as a private office. A dedicated homework room with chalkboard, second-floor laundry and a window nook between the first and second floors add another layer of thoughtful functionality. For the car enthusiast, the garage may steal the show. Outfitted with a car lift, built-in tool bench and racking system, it has been designed with the same attention to detail as the rest of the home. Outside, an inground pool, pergola and outdoor kitchen create a backyard designed for entertaining and relaxed family living. The pool house with outdoor bathroom tops off the outdoor oasis! This is a home where form and function have been considered in equal measure, and where the difference truly is in the details. (id:5764)

2434 TAYLORWOOD Drive, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd..

$2,998,000

3 Beds ⋅ 4 Baths ⋅ 40869469 MLS® #

SPECTACULAR LUXURY TOWNHOME IN THE HEART OF DOWNTOWN OAKVILLE! This stunning freehold end-unit residence offers approx 2,950 sq. ft. of luxurious living space and has been completely transformed from the studs with exceptional craftsmanship and high-end finishes throughout. Offered fully furnished and professionally designed, this turnkey home features 2+1 bedrooms, 4 baths, oak hardwood flooring, two fireplaces and a custom Brahms kitchen. A separate entrance to the lower level adds convenience and versatility. Enjoy a private terrace off the kitchen and a private rooftop terrace, ideal for outdoor entertaining. A rare double-car garage with parking for three vehicles completes this exceptional offering. Perfectly situated steps from downtown Oakville’s finest restaurants, boutiques, cafés and waterfront. An extraordinary opportunity to enjoy sophisticated, maintenance-free luxury living in one of Oakville’s most desirable locations. Simply move in and enjoy! (id:5764)

305 RANDALL Street, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$2,899,000

4 Beds ⋅ 3 Baths ⋅ 40869826 MLS® #

Welcome to this exceptional, completely rebuilt and renovated detached bungalow nestled in one of Southeast Oakville's most sought-after neighborhoods. Set on a rare, oversized lot, one of the largest on the street, this 3+1 bedroom, 3-bathroom home offers approximately 3,000 square feet of beautifully finished living space designed for comfort, elegance, and functionality. Step inside to discover soaring cathedral ceilings, an open-concept layout filled with natural light, and a seamless blend of luxury and warmth. The custom kitchen with high-end appliances flows effortlessly into the spacious living and dining areas, perfect for entertaining or everyday living. A private primary suite with a 150 square foot addition features a spa-inspired ensuite and serene views. The fully finished walk-out basement includes a large lower-level living area, guest bedroom with walkout, full bathroom, and generous storage, ideal for extended family, a home office, or nanny/in-law suite. Step outside to your expansive deck, ideal for summer gatherings and outdoor dining. The professionally landscaped yard is equipped with a full irrigation system, making lawn and garden maintenance a breeze. Located in prestigious Southeast Oakville, this home is surrounded by top-rated schools, mature trees, and quiet, family-friendly streets, offering a rare combination of privacy and convenience. Previously approved plans for an inground pool and patio from with drawings available upon request, subject to renewed permits and approvals! (id:5764)

201 TRELAWN Avenue, Oakville

Listing courtesy of The Agency.

$2,438,000

4 Beds ⋅ 4 Baths ⋅ 40868099 MLS® #

Welcome to an exceptional custom residence in the heart of Downtown Oakville, where timeless character meets beautifully updated modern living. Thoughtfully renovated throughout, this 4-bedroom, 4-bathroom home offers a bright, sophisticated layout designed for both everyday living and effortless entertaining. Step inside to an impressive open-concept main level filled with natural light, featuring hardwood flooring, designer lighting, and spacious living and dining areas. At the heart of the home, the gourmet eat-in kitchen makes a statement with quartz countertops, custom cabinetry, high-end stainless steel appliances, and an oversized centre island made for gathering. Upstairs, the primary suite offers a peaceful retreat with custom built-in cabinetry and a spa-inspired ensuite featuring a glass walk-in shower, freestanding tub, and double vanity. Two additional bedrooms share a beautifully appointed 4-piece bathroom. Continue to the top floor where an expansive, light-filled loft offers incredible flexibility as a fourth bedroom, home office, lounge, or studio, complete with ensuite bathroom potential. A generous mudroom landing provides direct garage access and additional storage. The fully finished lower level adds even more living space with oversized above-grade windows and a stunning 3-piece bathroom with steam shower. Outside, multiple walkouts lead to a private, maintenance-free backyard oasis designed for relaxing and entertaining. Extensive improvements include renovated bathrooms and laundry (2018), flooring updates, basement window wells (2024), freezer (2024), and new roof, windows, and garage door (2025). Just steps from the lake, Oakville Harbour, Downtown boutiques, restaurants, parks, and highly regarded schools, this turnkey home offers an exceptional lifestyle in one of Oakville's most coveted neighbourhoods. (id:5764)

48 FORSYTHE Street, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$2,998,000

3 Beds ⋅ 3 Baths ⋅ 40867529 MLS® #

Set on a spectacular 0.566-acre lot, this property is enveloped by towering trees and lush gardens, and backing onto the tranquil Kings Park Woods. Offering nearly 25,000 sq. ft. of privacy and tranquility, this Muskoka-like retreat sits on one of Southeast Oakville's most prestigious streets. A generously sized interlocked driveway leads past the elegant front yard to an impressive 3-car garage. Lovingly maintained by the same family for over 40 years, the home is in pristine condition. The interior features expansive principal rooms, including formal living and dining spaces, a large kitchen with a breakfast area addition, and an open-concept family room—perfect for both day-to-day living and entertaining. A wealth of windows throughout brings in abundant natural light and frames beautiful views of the front streetscape as well as the forested backyard. With multiple fireplaces and hardwood floors throughout the main level, the home exudes warmth and charm. Convenient access to the garage is provided through the laundry room. Upstairs, the spacious primary suite is complemented by three double closets, built-in bookcases, a 3-piece ensuite, and additional flexible space. Two more generously sized bedrooms, along with a 4-piece bathroom featuring a jacuzzi tub, complete this level. The true highlight of the home is the backyard—a private oasis of mature trees, manicured gardens, and a well-positioned pool that basks in sunlight. A full irrigation system ensures the landscaping stays lush. Recent upgrades include a new roof, furnace, and electrical panel, while the garage boasts 50-amp service, ideal for a lift or electric vehicle charging. Walking distance to Oakville’s top public and private schools, including OT and St. Mildred’s, and just minutes to shopping, this property offers exceptional potential. Whether you choose to build a custom home or renovate and expand this charming residence, the large lot allows for endless possibilities. (id:5764)

1296 CUMNOCK Crescent, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd..

$2,499,000

4 Beds ⋅ 4 Baths ⋅ 40865765 MLS® #

Welcome to 3270 Shelburne Place, tucked away on a quiet cul-de-sac in sought-after Bronte, south of Lakeshore Road and just steps from Lake Ontario, parks and scenic walking trails. This beautifully updated 4-bedroom home offers an impressive list of improvements and generous living space. The main level features a family room, oak hardwood flooring throughout, 6” baseboards and California shutters. At the heart of the home is the stunning renovated kitchen, featuring an oversized 85” x 42” island, abundant cabinetry and storage, brushed-gold accents, ceramic backsplash, under-cabinet, pot and pendant lighting. The sunny adjoining eating area features a double-sided wood-burning fireplace, skylight, and sliding glass doors, walk out to the patio and pool with waterfall area. The stylish, renovated laundry room features shiplap walls, a butcher-block counter, a laundry sink, custom storage and updated flooring. The main-floor powder room has also been beautifully updated. The upgraded oak staircase adds warmth and character, leading to 4 bedrooms with updated carpeting, lighting and California shutters. The primary suite offers a private sitting area, walk-in closet and 4-piece ensuite with a skylight, while the 5-piece main bath features heated floors, a glass shower, jetted tub and double sinks. The finished lower level provides even more living and entertaining space, new vinyl flooring, pot lights, a wet bar with ceramic backsplash and shelving, an updated 2-piece bathroom, a sauna with a separate shower and plenty of storage. Step outside to your own private backyard retreat featuring a heated saltwater pool and stone patios, perfect for summer entertaining. The property also offers ample driveway parking, security lighting and an updated garage with a newly painted floor. A wonderful opportunity to enjoy a beautiful home in one of Bronte’s most desirable pockets, close to the lake, parks, schools, shopping and restaurants. (id:5764)

3270 SHELBURNE Place, Oakville

Listing courtesy of Real Broker Ontario Ltd..

$2,198,000

4 Beds ⋅ 2 Baths ⋅ 40866851 MLS® #

Welcome to this bright and beautifully maintained raised bungalow, offering over 2,600 sq. ft. of finished living space and a spectacular backyard oasis, ideally situated in the highly sought-after West River neighbourhood. The sun-filled eat-in kitchen is a true highlight, surrounded by wraparound windows overlooking the private backyard and featuring an extended quartz peninsula, generous pantry space, gas stove, reverse osmosis water system, and patio doors leading directly to the outdoor entertaining areas. The inviting living and dining rooms feature built-in bookcases and offer an ideal setting for entertaining family and friends. The main level also includes a spacious primary bedroom, two additional well-sized bedrooms—one currently used as a home office—and a 4-piece bathroom. The finished lower level provides exceptional additional living space with a cozy den featuring a gas fireplace, a large sun-filled bedroom, 3-piece bathroom, spacious recreation room currently used as an office, and a functional laundry room with ample cabinetry and counter space. Step outside and discover your own private backyard retreat, complete with multiple decks and patios, a gazebo, raised reading nook, storage shed, beautifully landscaped mature gardens and trees, and an impressive inground pool with spillover hot tub. Whether entertaining guests, enjoying summer days by the pool, or simply relaxing in the peaceful surroundings, this backyard offers something for everyone. Ideally located within walking distance of downtown Oakville, vibrant Kerr Village, Oakville GO Station, Westwood Park and Forster Park with its playground and splash pad, as well as public transit and school bus routes. A wonderful opportunity to enjoy comfortable family living, exceptional outdoor space, and a convenient Oakville location. (id:5764)

316 RIVER SIDE Drive, Oakville

Listing courtesy of RE/MAX Aboutowne Realty Corp..

$2,198,000

3 Beds ⋅ 3 Baths ⋅ 40865228 MLS® #

If you’re a buyer looking in Morrison under the $2.5M mark, you may be finding your options to be a little…complicated. At this price point, properties tend to fall somewhere along the axis of land or house. Finding one where you have a compelling case for both is considerably harder. So, first things first. Buy on the best street you can afford. This is where Donlea delivers. A genuinely quiet street, beautiful homes, right at the heart of the neighbourhood and with schools close enough for the children to walk themselves. Frankly put, it’s ideal. Then there’s the land. With a new survey available, this west-backing 93’ x 185’ lot with stream offers the potential to build approximately 5,200 sq. ft. For those looking to create their forever home, it’s a rare opportunity to secure a substantial piece of land in one of Oakville’s premier neighbourhoods. But it would be remiss not to acknowledge that there is also a great deal of house here to love - and renovate. The existing 3,263 sq. ft., four-level side-split is surprisingly generous, with large bedrooms, a double garage and plenty of scope to reimagine the spaces. Think contemporary interiors, wall-to-wall windows and a seamless floorplan, all while retaining the scale and character that make this house work. A fantastic opportunity for those who want to control their budget while creating equity. In other words, you have options. Build new. Renovate. Or simply take your time and decide what makes the most sense for you. With this kind of flexibility, the upside is yours to create. (id:5764)

1242 DONLEA Crescent, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd..

$2,699,900

4 Beds ⋅ 5 Baths ⋅ 40863699 MLS® #

Some homes impress with their interiors. Others with their setting. Rarely do you find one that delivers both quite like this. Tucked into a quiet court and set against a spectacular mature ravine in the heart of River Oaks, this exclusive Merrick Seven Oaks Collection Grosvenor model offers over 6,000 sq ft of finished living space and a remarkable combination of privacy, scale and timeless sophistication. Generous principal rooms unfold across a light-filled main level, from elegant living and dining rooms to a 25-ft kitchen with custom cabinetry and premium built-inappliances and a separate family room with fireplace. At the rear, a nearly 22-ft sun room with skylights and fireplace draws your eye to the greenery beyond. Upstairs, the impressive primary retreat spans almost 30 ft and is joined by three generous bedrooms and a substantial private office with its own fireplace. The lower level is made for entertaining, with a large recreation room and wet bar, gym, full bath, wine cellar, separate tasting room and walk-up to the backyard. But step outside and the character of this property changes completely. More private resort than backyard, a series of outdoor living spaces unfolds against the ravine. A sparkling pool and hot tub anchor the setting, surrounded by extensive hardscaping and an elevated deck for dining and BBQs. A covered pergola creates an intimate outdoor lounge, while a separate terrace tucked among the trees offers another quiet escape. Mature landscaping wraps around it all, creating remarkable privacy and a backdrop that changes with the seasons. All this in one of Oakville's most established family neighbourhoods, surrounded by parks and trails and close to highly regarded public and private schools. A home where exceptional space, remarkable privacy and the natural beauty of its ravine setting come together in one of River Oaks' most desirable locations. (id:5764)

324 OAKRIDGE Court, Oakville

Listing courtesy of RE/MAX Aboutowne Realty Corp..

$2,299,000

5 Beds ⋅ 4 Baths ⋅ 40861787 MLS® #

Welcome to this rarely offered custom Fernbrook Bungaloft located on a quiet street in sought after Bronte Creek. This exceptional stone, stucco and brick residence offers 3,239 sq. ft. above grade living, plus over 1,900 sq. ft. of professionally finished lower-level living space - perfectly suited for multi-generational living. Inside you'll find elegant and thoughtful details throughout. Rich hardwood flooring, custom lighting, soaring ceilings and oversized windows that fill the interior with natural light. The chef-inspired kitchen features custom cabinetry, stainless steel appliances and a large centre island overlooking the great room with a cast stone fireplace. Spacious breakfast area opens through French doors to the private deck overlooking the manicured backyard. The main-floor primary suite offers the ease of bungalow living, complete with his and her closets and a spa-inspired five-piece ensuite. A formal dining room with coffered ceiling, private office, powder room and laundry room complete the main level. Upstairs two generously sized bedrooms share a full bath. The walk-out lower level is an exceptional extension of the home, incredible natural light, a full kitchen, an expansive recreation room with gas fireplace, two bedrooms, a three-piece bathroom and roughed in second laundry room. With direct access to the backyard, this thoughtfully designed space is ideal for extended family, older children, guests or multi-generational living. The fully landscaped front and rear grounds feature an inground sprinkler system, stone pavers and thoughtfully designed living areas that maximize privacy and entertaining. A true double-car garage with loft storage provides exceptional functionality. Ideally located steps from Bronte Creek Provincial Park, scenic walking trails, and green space, this incredible home offers an exceptional lifestyle in one of Oakville’s most coveted communities. (id:5764)

3248 RIBBLE Crescent, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$2,749,000

4 Beds ⋅ 3 Baths ⋅ 40864314 MLS® #

A rare combination of character, space and exceptional walkability in the heart of Downtown Oakville. Set on an impressive 70-foot-wide property, this beautifully renovated four-bedroom home blends the charm of an established residence with the quality and functionality of a thoughtful, high-end renovation. Extensively updated by Stonewood Homes, the interior features wide-plank white oak flooring, exposed wood beams, natural stone fireplaces and custom millwork throughout. The main level offers an impressive collection of living spaces, beginning with a bright enclosed sunroom and flowing through separate living and dining rooms to the open-concept kitchen and family room at the rear of the home. The kitchen is beautifully appointed with custom Chervin cabinetry, high-end appliances and a large centre island with seating. A substantial walk-through servery provides exceptional storage complete with additional cabinetry, sink, beverage refrigeration and wine storage. Upstairs, four bedrooms include a spacious primary suite with a walk-in closet and a beautifully finished ensuite featuring a freestanding tub. Three additional bedrooms and a second full bathroom provide an ideal layout for family living. The finished lower level adds valuable living space with a large recreation room, laundry room, workshop and extensive storage. Outside, the unusually wide lot allows for multiple outdoor living spaces surrounded by mature trees that create a wonderful sense of privacy. A large rear deck extends the main living area outdoors, while the landscaped backyard leads to a separate covered pavilion. Adding to the property's appeal is a detached two-car garage and two separate driveways, a rare offering this close to Downtown Oakville. Located just steps from the restaurants of downtown, and within easy reach of the lakefront, harbour, parks and schools, this is a unique opportunity to enjoy one of Oakville's most desirable and walkable neighbourhoods. (id:5764)

139 ALLAN Street, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd..

$2,690,000

5 Beds ⋅ 5 Baths ⋅ 40862377 MLS® #

Welcome to 408 Seabourne Drive, a charming 4 + 1 bedroom and 4.5 Bath custom-built home in desirable West Oakville, surrounded by mature trees and showcasing exceptional curb appeal. The stone and stucco exterior, architectural metal accents, extensive interlocking and covered entrance create a striking first impression. Inside, the bright and beautifully finished main level features marble-look flooring, rich hardwood, crown moulding, pot lights, an elegant staircase and a living area with large windows and a dramatic floor-to-ceiling fireplace. The stunning custom kitchen offers extensive cabinetry, quartz-style countertops and backsplash, a large contrasting island with seating, decorative glass cabinetry, under-cabinet lighting and stainless steel appliances, along with a spacious family room, private office and stylish powder room. The upper level features hardwood floors, generous bedrooms and excellent closet space. The impressive primary retreat includes a custom walk-in closet and spa-inspired ensuite with dual vanities, freestanding soaker tub and oversized glass shower. Convenient upper-level laundry adds everyday functionality. The expansive finished lower level offers a large recreation/media area, second kitchen with grey cabinetry, wood countertops, stainless steel appliances and a striking live-edge island, plus a wood-lined pantry, bedroom, renovated bathroom and flexible space for a gym, office or games area. The garage is equipped with separate heating equipment, providing added comfort and year-round functionality. Outside, enjoy a generous private lot with mature trees, landscaped grounds, expansive interlock patios, tiered gardens and a large covered gazebo with decorative lighting. Ideally located close to green space, tennis courts, community amenities and beautiful Lake Ontario. A beautifully appointed home combining custom craftsmanship, modern elegance and exceptional indoor-outdoor living. (id:5764)

408 SEABOURNE Drive, Oakville

Listing courtesy of RE/MAX Aboutowne Realty Corp..

$2,300,000

4 Beds ⋅ 4 Baths ⋅ 40859993 MLS® #

Welcome to 489 Rebecca Street in one of South West Oakville's most desirable neighbourhoods. Beautifully renovated with a transitional contemporary style, blending timeless character, warm natural finishes, and modern updates throughout, this 3+1 bedroom, 4 bathroom home offers 2,483 square feet plus a finished lower level. The thoughtfully redesigned main floor features engineered hardwood, custom cabinetry, two gas fireplaces, a spacious great room, a main floor den, powder room, mudroom, and an inviting kitchen and dining area designed for everyday living and entertaining. Upstairs, the private bedroom level offers three generous bedrooms, including a serene primary retreat with walk-in closet, a separate sitting room/den, and a spa-inspired 5-piece en suite. The finished lower level adds excellent flexibility with a large rec room/bedroom, 4-piece bathroom, laundry area, storage, and utility/workshop space. The backyard is the showpiece of the property - an award-winning private oasis with extensive stonework, lush landscaping, irrigation, multiple seating areas, two pergolas, natural gas BBQ connection, and a stunning saltwater pool with waterfall feature, hot tub, gas heater, and remote-controlled pool system. A detached two-car garage adds further convenience and has been updated with a new garage door and opener, exterior keypad, reinforced roof structure, and set up for EV charging. (id:5764)

489 REBECCA Street, Oakville

Listing courtesy of RE/MAX Aboutowne Realty Corp..

$2,599,000

4 Beds ⋅ 3 Baths ⋅ 40859137 MLS® #

Welcome to this exceptional two-storey family residence nestled on one of South East Oakville's most desirable, tree-lined streets. Combining traditional charm with an ideal functional layout. There are generous spaces for entertaining and everyday family life. Step into the inviting living room, featuring a cozy fireplace and elegant California shutters that fill the space with warm, natural light. The updated eat-in kitchen serves as the heart of the home, complete with built-in appliances, ample cabinetry, and a spacious eat in area. For formal gatherings, the spacious dedicated dining room easily accommodates large family dinners and holiday celebrations. The dramatic main-floor family room steals the show with its soaring vaulted ceilings, second fireplace, and expansive windows. Slide open the doors to step directly onto the private back deck, overlooking a beautifully landscaped, west-facing rear garden-the ultimate setting for enjoying golden-hour sunsets, outdoor dining, and summer entertaining. Conveniently located on the main level, the spacious primary bedroom serves as a peaceful retreat, complete with a private 4-piece ensuite bath. Upstairs, you will find two additional bright bedrooms, fantastic storage solutions, and a second full 4-piece bathroom, making it ideal for kids, guests, or a dedicated home office. The fully finished basement significantly extends your living space, offering endless possibilities for a media room, play area, or home gym, along with a third 4-piece bathroom for added convenience.Located in a premier school district close to top-rated public and private schools, downtown Oakville's boutique shopping and dining, parks, and the lakefront, this South East Oakville gem perfectly blends main-floor comfort with long-term versatility. A rare opportunity on a prime street! (id:5764)

380 WATSON Avenue, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$2,195,000

4 Beds ⋅ 2 Baths ⋅ 40856200 MLS® #

Welcome to a home perfect for young couples, growing families or retirees looking to enjoy one of Oakville’s most established neighbourhoods. Loved by the same family for over 50 years, this home is filled with a lifetime of memories. Set in the highly sought after Morrison neighbourhood of Southeast Oakville, this special property offers privacy, mature surroundings and an exceptional location close to top rated schools, parks and everything this incredible community has to offer. Inside, the home feels bright and welcoming, with a comfortable layout for everyday living. The updated kitchen features a sunny breakfast area and flows naturally into the dining room, where a walkout leads to the deck and backyard. The spacious living room is filled with natural light from a large picture window, creating an inviting place to relax or entertain. Upstairs are three generously sized bedrooms and a four-piece bathroom. A few steps down, the family room offers another warm and comfortable gathering space, complete with a wood burning fireplace perfect for cozy winter afternoons. Around the corner is a fourth above grade bedroom that could also make an ideal home office, along with a two-piece bathroom. This level also features a walkout to the backyard, making it easy to enjoy the outdoor space. The unfinished basement provides even more potential, with laundry, storage and the opportunity to create additional living space to suit your needs. Outside, a three car driveway plus a single car garage provides plenty of parking. With an incredible location, beautiful mature surroundings and more than 50 years of memories within its walls, this is a special place to call home. Now it’s ready for a new chapter and new memories to be made. (id:5764)

401 CAIRNCROFT Road, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$2,150,000

4 Beds ⋅ 3 Baths ⋅ 40846782 MLS® #

Luxury lakeside living in Bronte’s coveted Schooner’s Reach. Completely reimagined, this freehold townhome offers beautifully renovated, low-maintenance living just steps to the lake, marina and vibrant shops and restaurants of Bronte Village. When your home feels larger than you need and upkeep begins to take more than it gives back, the idea of change becomes compelling. Here, you have the space you want with none of the demands you don’t. The main level features wide-plank flooring, expansive sightlines and a refined redesign throughout. The kitchen includes custom cabinetry, quartz surfaces, integrated wall ovens, gas cooktop and two-tone finishes. Additional windows enhance natural light in the family room, while patio doors lead to a large private terrace, ideal for outdoor dining or relaxed evenings under the stars. A rebuilt staircase across all three levels with hardwood treads and modern railings serves as a striking architectural feature. Pot lighting, contemporary fixtures and under-cabinet lighting add warmth and function. The second level offers three flexible rooms suited to bedrooms, office or living space. One larger room works well as a lounge or workspace, while still allowing for two additional bedrooms. A renovated full bath and laundry complete the level. The third floor is dedicated to a private primary retreat with a spacious bedroom, custom dressing area, three walk-in closets, a five-piece ensuite and its own balcony. A flexible lower level provides space for a home office, gym or media room, along with storage and interior access to the double garage. Membership in the Schooner’s Reach Owners Association, currently $150 per month, includes lawn care, landscaping, spring and fall cleanups, snow removal and seasonal window cleaning, along with a private tennis court and shared greenspace. A lock-and-go lifestyle in a friendly, freehold lakeside community. (id:5764)

63 TRADEWIND Drive, Oakville

Listing courtesy of RE/MAX Aboutowne Realty Corp..

$2,599,999

5 Beds ⋅ 4 Baths ⋅ 40845570 MLS® #

Perfectly positioned in one of Southwest Oakville's most sought-after neighbourhoods, directly across from the prestigious Appleby College, this exceptional family residence offers over 5,000 square feet across all levels, blending timeless elegance with outstanding functionality. Thoughtfully designed for both everyday living and entertaining, the main level showcases expansive principal rooms filled with natural light. The chef-inspired kitchen is the heart of the home, featuring custom cabinetry, granite countertops, a large centre island, quality appliances, and an adjoining breakfast area overlooking the private backyard. The inviting family room offers beautiful seamless access to the outdoor living spaces, while the formal living and dining rooms provide refined spaces for hosting family gatherings and special occasions. A handsome wood-panelled home office creates the perfect work-from-home environment. Upstairs, the home offers 3 spacious bedrooms, highlighted by a luxurious primary retreat complete with a generous walk-in dressing room and spa-inspired ensuite with heated floors. The additional bedrooms are well-proportioned and ideal for family or guests. The finished lower level extends the living space with 2 additional bedrooms, a large recreation/media room, a custom wine cellar, ample storage, and flexible space perfect for extended family, teenagers, or a home gym. Set on a private, mature lot, the backyard features an in-ground pool, hot tub and exceptional privacy, creating the perfect setting for summer entertaining. Ideally located just moments from the lake, parks, downtown Oakville, and top-rated schools, this is an outstanding opportunity to own a distinguished family home in one of Oakville's most coveted neighbourhoods. (id:5764)

104 WHITTINGTON Place, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$2,495,000

3 Beds ⋅ 2 Baths ⋅ 40841480 MLS® #

Tucked into the coveted Orchard Beach enclave in southeast Oakville and just steps from the lake, 32 Park Avenue is a timeless residence that blends classic charm w/thoughtful modern updates. Set beyond a magnificent magnolia tree on one of Oakville’s most desirable streets, this meticulously renovated home offers an exceptional lifestyle in a coveted lakeside setting. Enjoy morning strolls along the Esplanade, peaceful waterfront moments + views of sailboats gliding across the harbour. Inside, light-filled principal rooms unfold w/warmth and sophistication. The chef’s kitchen is beautifully appointed with commercial grade appliances, Carrara marble countertops, slate flooring + Perrin & Rowe fixtures. Designed for both everyday living + entertaining, it flows seamlessly into the dining room + inviting living room. A glass-enclosed sunroom overlooks the gardens + is warmed by a gas stove, creating a tranquil retreat that can be enjoyed year-round. Upstairs, three generous bedrooms are served by a beautifully renovated four-piece bath. The primary bedroom enjoys access to a private terrace, offering a peaceful setting for morning coffee or quiet relaxation. The finished lower level extends the living space with a welcoming recreation room, gas fireplace, bar area + custom walnut-and-glass wine display. Outside, mature magnolias, Japanese maples, rhododendrons, hemlocks + moonbeam plantings create an enchanting English garden setting. Curated landscaping lighting + frequent visits from songbirds enhance the sense of serenity. Offering a rare blend of tranquillity + convenience, this exceptional property is just a short stroll to downtown Oakville’s boutiques, cafes, restaurants, parks, harbour + waterfront trails, with GO Transit and top-ranked schools close at hand. Rarely does an opportunity arise in this prestigious lakeside pocket. Elegant, welcoming + undeniably special, this is Orchard Beach living at its finest. (id:5764)

32 PARK Avenue, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd..

$2,679,000

5 Beds ⋅ 6 Baths ⋅ 40828660 MLS® #

An exceptional custom residence set on a commanding 150 x 75 ft lot in one of Southwest Oakville's most established and coveted neighbourhoods.Boasting over 6,300 square feet of total living space, this home offers 5 bedrooms and 6 bathrooms across three beautifully finished levels. This home showcases a rare and highly desirable layout with two primary suites - one on the main floor and a second grand retreat upstairs. Designed for elevated living and effortless entertaining, the home features refined principal rooms including formal living and dining areas, a private office, two powder rooms, and a full laundry suite. At its heart, the chef's kitchen impresses with rich cabinetry, granite countertops, marble flooring, a large centre island with seating, built-in stainless steel double wall ovens, gas cooktop, beverage fridge, and seamless flow into the family room with gas fireplace and custom built-ins. The main-floor primary suite offers privacy, an ensuite bath, and walk-in closet - ideal for multigenerational living or main-level convenience. Upstairs, the second primary retreat feels like a private sanctuary with its own fireplace, spa-inspired ensuite, and generous dressing space. Two additional bedrooms share a spacious 5-piece Jack & Jill bath, creating a functional family wing. The fully finished lower level enhances the lifestyle appeal with a large recreation lounge, wet bar, gym area, fifth bedroom, and full bath - perfect for guests or extended family. Outdoors, a private backyard oasis framed by mature landscaping features an inground pool, pergola-covered lounge, multiple hardscape entertaining areas, and a detached shed. A double garage with upgraded tiled flooring and private driveway complete this distinguished offering. Five bedrooms. Two primary suites. Three finished levels. A rare estate-sized lot in Southwest Oakville. 390 Seaton Drive - a home of scale, versatility, and enduring elegance. (id:5764)

390 SEATON Drive, Oakville

Listing courtesy of RE/MAX Aboutowne Realty Corp..

$2,449,000

4 Beds ⋅ 4 Baths ⋅ 40817114 MLS® #

MOVE BEYOND THE STANDARD in Oakville’s prestigious Joshua Creek. This refined 4,200+ SF residential asset is a masterclass in architectural volume and intentional flow. Engineered for grand-scale entertaining, the residence opens to a soaring double-height foyer and a curved staircase, leading into a light-filled living space anchored by a sophisticated two-sided gas fireplace. The formal dining room features custom coffered ceilings, while the chef-inspired kitchen and breakfast room offer a seamless transition to the private porch and rear grounds. STRATEGIC LAYOUT & DESIGN A secondary staircase provides direct lower-level access, complemented by a dedicated mudroom/laundry and abundant storage solutions. The upper gallery leads to a primary suite designed as a private sanctuary, featuring a spa-caliber ensuite and dual walk-in closets. Three additional oversized bedrooms offer unparalleled versatility, including a semi-ensuite and a private ensuite with a custom window bench. PREMIER LOCATION & ACCESS Positioned within the catchment of Ontario’s top-tier institutions—Joshua Creek Elementary and Iroquois Ridge SS—this property offers proximity to elite golf clubs, tranquil trail systems, and rapid transit/highway corridors (403/QEW/407). Experience the intersection of luxury and logic. Move Beyond the Search. (id:5764)

2238 LYNDHURST Drive, Oakville

Listing courtesy of ROYAL LEPAGE SIGNATURE REALTY.

$2,096,640

40802471 MLS® #

Three Oaks Business Centre presents occupiers and investors a rare opportunity to own state-of-the-art industrial condo including mezzanine. Built by Beedie, one of Canada's largest private industrial developers, Three Oaks Business Centre is designed to position your business for success with exceptional connectivity, operational efficiency, and the highest quality construction. Connect better with your customers and employees with direct access to the QEW. (id:5764)

3323 SUPERIOR Court Unit C103, Oakville

Listing courtesy of Colliers Macaulay Nicolls Inc..

Oakville Properties between $2,000,000 and $3,000,000 for Sale

Newest Oakville Properties between $2,000,000 and $3,000,000 for Sale

How much is your home worth?

How much is your home worth?

Contact Us

Services