Oakville Real Estate | Oakville Properties between $2,500,000 and $5,000,000 for Sale

Experience exceptional West Oakville living in this custom-built residence designed by renowned local architect Joris Keeren. Set on a rare pie-shaped lot widening to 97 feet at the rear, the home offers more than 6,000 sq. ft. of thoughtfully designed, light-filled living space.A dramatic 20-foot foyer introduces the main level, where the chef's kitchen features a striking T-shaped island, professional-grade appliances, and a walk-in pantry with a dedicated servery. The spectacular Great Room boasts 18-foot ceilings and opens to a cedar-lined covered porch-an inviting four-season retreat complete with a built-in BBQ, task sink, and double-sided gas fireplace.Upstairs are four generous bedrooms, including a luxurious primary suite with a custom walk-in closet and spa-inspired five-piece ensuite. A well-appointed laundry room with a steam styler adds everyday convenience.The lower level is designed for entertaining, featuring radiant in-floor heating, a wet bar with wine display, and a fully equipped home theatre with Control4 automation, projector, and included seating. Ideally located minutes from Appleby College, excellent schools, and the lake, this remarkable residence pairs architectural distinction with refined family living.

528 Wellington Crescent, Oakville

$2,979,000

5 Beds ⋅ 5 Baths ⋅ W13779562 MLS

Set on approx. 0.29 acres and backing directly onto Bronte Creek Provincial Park, this fully renovated family home offers exceptional privacy and over 5,500 sq. ft. of upgraded living space in Oakville's sought-after Bronte Creek community. Tucked away on a quiet crescent on one of the neighbourhood's largest lots, the property features professional landscaping, stamped concrete walkway, porch and French curbs, plus a 3-door, 2.5-car garage with epoxy floors, Garaga cabinetry/storage systems and EV charger. The backyard oasis features a covered patio, pool, cabana with bar and change room, and plenty of green space. Inside, the open-concept design showcases hardwood flooring, crown moulding, wainscoting, pot lights and designer lighting throughout. The main level offers formal living and dining rooms with coffered ceilings, private office, hall skylight and family room with custom built-ins and gas fireplace. The chef-inspired kitchen features quartz counters and backsplash, large island, Wolf stove, Sub-Zero fridge and breakfast area with walk-out. Main-floor laundry includes custom built-ins and sink. Upstairs are 4 spacious bedrooms, including a primary retreat with custom TV built-ins, W/I closet with organizers and spa-inspired ensuite. Bedrooms 2 & 3 share semi-ensuite access, while bedroom 4 has a W/I closet and private ensuite. The finished lower level features 9' ceilings, rec/living area with custom built-ins, wet bar, gym, 5th bedroom and full bath. Updates: renovation (2020), roof (2023), front windows (2025), pool pump (2023) & liner (2025). Walk to top-rated schools, parks & amenities; minutes to highways & transit.

3348 Skipton Lane, Oakville

$3,175,000

3 Beds ⋅ 4 Baths ⋅ W13775010 MLS

This bespoke architecturally designed single-storey residence, created in the Contemporary Shed Style, combines refined architecture with exceptional functionality and craftsmanship. Designed for sophisticated entertaining and comfortable family living, the home features dramatic interior rooms, clean lines, and seamless indoor-outdoor connections. Principal living spaces and bedrooms are positioned to maximize privacy and natural light through expansive floor-to-ceiling windows overlooking landscaped gardens. A generous foyer introduces over 3,100 sq. ft. of refined single-level living. At the heart of the home, a striking four-sided wood-burning fireplace connects the formal living and dining areas. The gourmet kitchen is equipped with premium appliances, sky-lighting, custom cabinetry, walk-in pantry storage, and built-in serving functions, while oversized glass doors open directly to the gardens and outdoor entertaining spaces. The adjoining family room is filled with natural light from extensive glazing and skylights, complemented by wide plank white oak flooring, custom millwork, and cathedral tongue-and-groove willow ceilings. The private primary suite includes a spa-inspired ensuite, walk-in closet, and direct garden access. Two additional bedrooms feature oversized windows and double closets. The lower level offers excellent versatility with a recreation room, oversized laundry and craft area, workshop, cedar storage room, and wine storage. Completing the property are a cedar shake roof, cobblestone driveway, double carport, and oversized double garage with parking capacity for up to seven vehicles, delivering a rare blend of luxury, comfort, and practicality.

1168 Carey Road, Oakville

$3,795,000

4 Beds ⋅ 4 Baths ⋅ W13774358 MLS

An exceptional opportunity on one of Southeast Oakville's most prestigious streets. Set on a nearly half-acre lot, 16 Colonial Crescent offers approximately 100 feet of frontage and more than 210 feet of depth, with outstanding proportions for a substantial custom build. The lot's generous dimensions and mature setting allow for an impressive new residence while maintaining exceptional privacy and meaningful outdoor space. Surrounded by mature trees and distinguished homes, the property offers a sense of scale and seclusion rarely found this close to the lake. RL1-0 zoning provides the potential for more than 6,000 square feet of above-grade living space, while still allowing for generous outdoor living, a pool and landscaped gardens, subject to applicable approvals. The property is currently a spacious four-bedroom residence offering approximately 3,700 square feet above grade, plus a finished lower level, attached double garage and inground pool-providing the flexibility to lease the home while planning a future build. Colonial Crescent is a quiet, established enclave known for its large properties, mature tree canopy, and impressive custom homes. Just steps from the lake and Gairloch Gardens, the location also offers convenient access to Downtown Oakville, excellent public and private schools, parks and the waterfront. A rare opportunity to secure a significant building lot on one of Southeast Oakville's premier streets and create an exceptional custom home in an highly sought-after location.

16 Colonial Crescent, Oakville

$3,999,000

6 Beds ⋅ 7 Baths ⋅ W13772104 MLS

Brand new, never lived in, and exceptionally located within walking distance of Downtown Oakville, this home offers a rare opportunity to enjoy a newly built luxury residence in one of the town's most established neighbourhoods. Designed by Keeren Design with interiors by Kate + Co, the home sits on a generous 70' wide property and offers over 3,600 square feet above grade. Thoughtfully designed across three finished levels, it pairs transitional architecture with warm, sophisticated interiors defined by soaring ceilings, expansive windows, custom millwork and a refined palette of natural wood, stone and plaster. The main level balances formal and casual living with an elegant dining room and an open-concept kitchen and family room. The custom kitchen features extensive cabinetry, integrated top-of-the-line appliances, a large island and separate servery with walk-in pantry. Beyond, the dramatic two-storey family room is filled with natural light and anchored by a beautiful plaster fireplace. A covered rear terrace extends the living space outdoors with separate dining and lounging areas centred around a two-sided gas fireplace, overlooking the backyard. Upstairs, the primary suite features a luxurious ensuite and extensively fitted dressing room. Each additional bedroom enjoys its own ensuite, while laundry is conveniently located on this level. The finished lower level offers a large recreation area with fireplace, wet bar, two additional bedrooms and bathrooms, gym, large windows and a walk-up to the rear yard. Downtown Oakville is an easy walk from your front door, with shops, restaurants, cafes and the waterfront close by. Kerr Village, parks and lakefront trails are also nearby, offering an exceptional walkable lifestyle and the ease of a brand-new home in an established Oakville neighbourhood.

61 Highland Road, Oakville

$3,250,000

5 Beds ⋅ 5 Baths ⋅ W13765332 MLS

Simply stunning. Modern farmhouse inspired, with high end European finishes from head-to-toe! Some of the features of this stylish & functional home include: top of the line chefs kitchen, 4+1 large bedrooms (2 with ensuites), 4.5 bath, main floor office, expansive walk-out basement & pool sized 72 wide lot on a quiet street. High ceilings on all floors(10 main floor, 10 second, 9 basement) wide plank engineered hardwood, thermal break aluminum triple pane windows & doors, high end plumbing hardware & solid wood interior doors. Light filled dining room with double french door walkout to back deck, modern chandelier & custom built cabinets. Jaw dropping kitchen features quartz backsplash & quartz counters & wood island with bar seating & waterfall edge. Integrated appliances including Gaggenau fridge, Bosch dishwasher, Sharpe microwave, F. Bertazzoni gas range & hood (with pot filler). Bright living room with built-in storage cupboards with slat wood feature wall & window bench. Refined glass-walled office space with custom cabinetry & shelving. Floating white oak staircase with overhead skylight leads to second level. Primary bedroom boasts hidden walk-in closet with built-in organizers, Juliet balcony, walkthrough closet to 6pc ensuite bath. Luxurious ensuite with heated porcelain tile floors, imported Italian soaker tub, glass shower with double rainhead & double vanity. 2nd bedroom (can be 2nd primary), with walk-in closet, Juliet balcony, electric fireplace feature wall with custom surround and ensuite. Ensuite bath features skylight and glass shower with rain shower head with light features. 2nd floor also includes spacious 3rd & 4th bedrooms, high end main bath and laundry room. Basement is bathed in natural light from above grade windows & walkout. Basement features a 5th bedroom, gym, rec room (with fireplace), full bathroom, storage (with rough-in for sauna), laundry room, and expansive bar area. Incredible home that impresses from start to finish!

480 Scarsdale Crescent, 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

$3,795,000

4 Beds ⋅ 4 Baths ⋅ W13763614 MLS

Private, elevated, and unlike anything else in Old Oakville - A true four-season outdoor retreat, your private playground for the outdoor enthusiast-where each day invites skating, paddling, kayaking, hiking, fishing, boating and cross-country skiing, alongside wildlife watching and refined al fresco dining, embracing nature in all its seasons. This lofted waterfront residence commands breathtaking views and unmatched privacy along the tranquil 16 Mile Creek. A testament to craftsmanship and design, this waterfront retreat boasts exclusive riparian rights and a private dock, inviting you to embrace the beauty of Oakville's scenic waterways year-round. .A meticulous 2016 renovation elevated this residence with rich hand-scraped oak floors, solid wood doors, custom millwork, and elegant tray ceilings. The sprawling 1,700 sq. ft. premium Wolf PVC deck includes a hot tub oasis, integrated fire table, and motorized awnings, leading to a dock with a kayak launch, swim ladder, and floating dock. Glass-encased staircases on helical piers deliver striking architectural presence and unbroken sight lines to the creek. Inside, sophistication defines every detail. Floor-to-ceiling windows in the living room frame stunning ravine views and dramatic sunsets, while a gas fireplace with a live-edge mantel adds warmth. The chef's kitchen impresses with a leathered Taj Mahal quartzite island, Wolf and Miele appliances, and an integrated Sub-Zero fridge. Heated floors run throughout, including in the spa-like primary ensuite with marble floors, a rain shower, and double vanity. The lower level offers a linear fireplace, built-in bar, and walkout to the deck. A concrete-lined storage room playfully known as the Bomb Shelter provides additional functionality. Blending natural beauty, refined design, and year-round outdoor living, this one-of-a-kind property is just steps to downtown Oakville and the GO Train offering luxury, serenity, and convenience in equal measure.

382 Trafalgar Road, 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

$2,999,000

5 Beds ⋅ 5 Baths ⋅ W13758398 MLS

Welcome to 168 Walby Drive, a rare offering in prestigious Coronation Park. This custom-built natural stone bungaloft, built in 2012, offers over 6,300 sq. ft. of finished living space on a premium 102.8' x 121.2' lot, including nearly 4,000 sq. ft. above grade and a fully finished lower level with a separate entrance. A dramatic two-storey foyer welcomes you into an elegant interior featuring site-finished 4" quarter-sawn white oak floors, 9' ceilings, 8" baseboards, 9" plaster crown mouldings, extensive pot lighting, and a solid oak staircase with wrought iron pickets.The flexible floor plan offers both a main-floor primary suite and a second-floor primary suite option, each with a luxurious 5-piece ensuite and walk-in closet, making the home ideal for main-floor living, multi-generational families, or traditional family living. The gourmet eat-in kitchen features a large centre island, granite countertops, under-cabinet lighting, a glass tile backsplash, a built-in computer niche, premium JennAir stainless steel appliances, and a bright breakfast area, flowing seamlessly into the adjoining family room and formal dining room.The second floor offers three bedrooms and two full bathrooms, with vaulted and sloped ceilings that add warmth and architectural character throughout, as well as the convenience of a second laundry area. The fully finished lower level, with its own separate entrance, includes a spacious entertainment room, recreation room, fifth bedroom, and full bathroom, offering exceptional flexibility for extended family, an in-law suite, or future income potential.Complete with an attached double garage, parking for six vehicles, main-floor and second-floor laundry, central vacuum, central air conditioning, and a quiet street location just steps to the lake, top-rated schools, parks, and downtown Oakville, this exceptional home combines timeless craftsmanship, outstanding flexibility, and an unbeatable South Oakville location.

168 Walby Drive, Oakville

$4,495,000

W13756534 MLS

183 Maurice Drive, Oakville. 12-Suite Apartment Building. Exceptional Oakville Multi-Residential Investment Opportunity. Well-maintained and extensively renovated 12-suite apartment building situated on a large 118.5' x 90.29' lot in Oakville. The property offers an attractive combination of renovated suites, strong in-place income, ample parking and significant recent capital improvements. Property Highlights: *12 Residential Suites *6 x Two-Bedroom Suites *6 x One-Bedroom Suites *Approximately $215,000 Net Income *16 Surface Parking Spaces * Comprehensive Renovations and Upgrades Throughout *Numerous custom kitchens featuring quartz countertops and stainless-steel appliances *Numerous Modernized bathrooms *3/4-inch solid oak hardwood flooring in many living areas and bedrooms *Extensive Suite and Building-System Improvements - providing a substantially upgraded asset with reduced anticipated near-term maintenance and capital-expenditure requirements * High-Efficiency Viessmann Boiler - 2024 * Large 118.5' x 90.29' Lot * Recent Phase One and Phase Two Environmental Reports Available. Investment Highlights: This property presents an excellent opportunity to acquire a substantially upgraded multi-residential asset in the established Oakville market. The suites and major building systems have been extensively updated, providing a turnkey investment with significantly reduced anticipated maintenance requirements for the foreseeable future. Combined with efficient building systems, generous parking, a large lot and strong in-place income, the property provides a strong foundation for long-term ownership and continued income growth.**Fully Rented**

183 Maurice Drive, Oakville

$3,998,900

4 Beds ⋅ 4 Baths ⋅ W13736840 MLS

Incredible offering in the Harbour district of Old Oakville one block from the lake and harbour and a short stroll to beautiful downtown Oakville. Over 3500SF of luxury living space. Beautiful custom build with open concept floor plan featuring soaring 10' ceilings and filled with light via wall-to wall windows and dramatic skylights. 3-floor elevator. Exceptionally high-end quality construction and attention to detail. Living Room with fireplace open to Kitchen with built-in SubZero & Wolf appliances, quartz counters, Butler's pantry with full height SubZero freezer and exceptional storage. Walk-out to a beautiful fully covered porch 27' x 11' with low maintenance composite decking. Beautiful Primary suite with south-facing lake view from Juliette Balcony, luxury Ensuite with heated floors, dual sinks, soaker tub and glass shower; Walk-in closet with built-in cabinetry. 2 further bedrooms with Juliette balconies with lake views. Main bath with heated floors and glass shower. Second floor Laundry. The ultimate lower level features high ceilings, radiant heated floors throughout, patio door walk-out to covered patio and access to the garden, large open concept Recreation Rm, full second Kitchen with high-end appliances, 4th Bedroom & guest bathroom; Cedar lined sauna with easy access to get outside to the hot tub. Triple Glazed windows throughout. Wired Security System. Irrigation System. The fenced garden features lush landscaping, large patio and gazebo for hot tub. Inside entry from oversized, 2-car garage with 12 ceilings can accommodate a car-lift.

36 Anderson Street, Oakville

$4,995,000

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

$2,599,000

4 Beds ⋅ 3 Baths ⋅ W13724754 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!

380 Watson Avenue, Oakville

$2,999,000

5 Beds ⋅ 3 Baths ⋅ W13722374 MLS

Well positioned property in historic Old Oakville, south of Lakeshore, just steps to the beach, Oakville harbour and Town Square. Sitting proudly up on a rise, this 2 1/2 storey home features wonderful views, light and plenty of space to create your dream home. With lot dimensions of 105' x 105' this full-sized 11,044 SF lot is exactly twice the size of adjacent properties. Savvy buyers may investigate opportunities to sever the lot or explore the creation of an accessory dwelling unit on the property. Zoning RL3, Special Provision 11. The existing home sits entirely on one half of the property in the northeast corner leaving the south and the west portions of the lot open to potential. The existing residence features high ceilings, a grand staircase, formal living room with wood burning fireplace and adjacent sunroom. Lovely southeast dining room takes in all the sunlight. The kitchen and back entrance are in the southwest corner of the main floor. The second floor features 4 bedrooms and one main bathroom. The third floor with two large rooms used as the Primary suite features wonderful views over the garden, the lake, church tower and the beautiful trees of Old Oakville.

200 WILLIAM Street, Oakville

$2,595,000

4 Beds ⋅ 3 Baths ⋅ W13706156 MLS

Located on one of Morrison's most sought-after streets, this 4-bedroom home enjoys an exceptional setting near the end of a quiet cul-de-sac on a premium 100' x 166' beautifully treed lot. Backing onto Wedgewood Park, the property offers a rare combination of privacy, tranquility and natural beauty. Whether you choose to move in, renovate or build your dream home, this exceptional property presents an incredible opportunity in one of Southeast Oakville's most coveted neighbourhoods just a short walk from some of Oakville's finest schools, including Oakville Trafalgar High School. Location, Location, Location!

328 Dalewood Drive, 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

$3,649,999

4 Beds ⋅ 5 Baths ⋅ W13697878 MLS

Tucked into a quiet court, this custom modern farmhouse, built by custom home builder Millbay Carpentry, sits on a 66 x 187 ft lot and offers over3,900 sq ft above grade with 4 bedrooms and 5.5 bathrooms, plus a finished walkout basement for approximately 5,500 sq ft of total living space. A custom EPAL front door opens to a double-height foyer with pine stairs and matte black railings, complemented by 10 ft main-floor and 9 ft upper- and basement-level ceilings. The great room features a wall of windows overlooking the pool and gardens, accented by cedar beams.The chef's kitchen showcases custom Barzotti cabinetry, a porcelain CIOT backsplash, JennAir appliances and an 8-burner range, along with a hidden walk-in pantry, custom built-ins and designer lighting. The primary ensuite features a steam shower, while the finished basement offers a gym, theatre, bar, lounge, gaming area and ample storage. Outdoors, enjoy a heated saltwater pool with an automatic cover, turf, irrigation and landscape lighting. Conveniently located near Oakville's only public International Baccalaureate (IB) school, as well as GO Transit, major highways and Oakville Place. (71030456)

1114 TRUMAN Avenue, Oakville

$2,599,900

5 Beds ⋅ 4 Baths ⋅ W13696852 MLS

Executive bungalow in prestigious Eastlake offering 5431 sqft of finished space on a mature, naturally elevated lot with excellent drainage. Located in top school zones (E.J. James FI, New Central, Maple Grove, OT). Ideal layout with 3 main-floor bedrooms including a primary suite with 5-pc ensuite. Vaulted ceilings, custom columns, hardwood floors, and premium windows bring elegance and comfort. Kitchen opens to family room and walk-out to saltwater pool and private yard. Walk-out basement adds 2 more rooms, rec room, office, gym, and kitchenetteideal for in-laws or teens. Recent upgrades include security camera system, alarm, recessed lighting, basement flooring, water softener, water filtration, newer A/C, and lawn irrigation system. Solid construction, quality finishes, and long-term potential in Oakvilles most coveted enclavemove-in ready, with opportunity to customize over time.

223 Trelawn Avenue, Oakville

$3,000,000

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

$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

$2,998,000

5 Beds ⋅ 3 Baths ⋅ W13673902 MLS

Rare raised bungalow featuring over 4000 SF of luxury living space in prime South East Oakville. Exceptional renovations throughout. The heart of the home is the large open concept kitchen / great room with walk-out to covered porch with retractable screens. Spectacular chef's kitchen with extensive custom cabinetry, quartz countertops, high-end appliances and a large 10x4 centre island. Large windows, 9 inch wide-plank engineered hardwood and quality lighting create an inviting living space around the exceptional stone fireplace with walnut mantel, perfect for large family gatherings. The main floor Primary suite features extensive built-in wardrobes and a luxurious 5-piece ensuite with glass shower and spa-inspired soaker tub. Two further generously-sized bedrooms with its own walk-in closets and a large newly renovated family bathroom as well as a handy main floor study area and mudroom entry complete the main floor. Fully finished lower level, featuring a large recreation room and billiard room with new luxury vinyl flooring. There are two further bedrooms with wall to wall wardrobes, a seasonal closet, renovated 3-piece bath, large walk-in closet, large laundry room and extensive storage. There is even a kitchenette creating the perfect space for a nanny or in-law suite. Step outside onto the stunning covered back porch complete with remote screens and electric heaters for all season enjoyment. The expansive 79'x151' lot has been professionally landscaped with patios, elegant outdoor lighting and a full irrigation system. Large double driveway with parking for 6 cars plus a deep garage with high-end shelving system and an EV charger. Located on a mature, sought-after street in Southeast Oakville, this home offers a rare combination of location, lot, quality and extensive recent improvements. Move-in and immediately enjoy one of Oakville's most sought after neighbourhoods just steps to Maple Grove Public School and Oakville Trafalgar High School. Don't miss!

1485 Duncan Road, 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

$4,390,000

5 Beds ⋅ 5 Baths ⋅ W13673302 MLS

Located in coveted West Harbour, come discover tranquility and elegance at 235 Lakewood Drive. Nestled on a generous .56-acre lot, embraced by majestic foliage in a private cul-de-sac, this residence epitomizes serene living mere steps from the lake. Crafted by renowned architect Gren Weis, the fusion of stone and wood siding spans over 6,200 square feet. Step into the foyer with its soaring cathedral ceilings, offering glimpses of the expansive living spaces beyond. Designed for seamless flow, this sophisticated layout effortlessly accommodates both grand and intimate gatherings. A bespoke oak staircase adorned with shimmering Schonbek chandeliers leads to the upper levels, where solid oak hardwood flooring graces much of the home. The living room boasts exquisite millwork, custom fireplace, and state-of-the-art entertainment amenities by Canadian Sound Ltd. The gourmet kitchen, recently reimagined, features top-tier appliances, quartz countertops, and abundant storage, with access to a sprawling composite, low maintenance deck. A stately maple wood-paneled study overlooks manicured gardens, providing a serene retreat. Five generous bedrooms, each with an ensuite and ample closets, offer luxurious comfort. The primary suite is a haven of indulgence, flaunting dual walk-in closets, spa-like ensuite with airy vaulted ceilings, skylights, and deluxe fixtures. The lower level is all about leisure and function, boasting a custom-painted wood-paneled rec room with lakeside vibes, alongside a gym, wine cellar, and top-notch utility room. Outside, the meticulously landscaped grounds offer a saltwater pool with waterfall, a spa, and outdoor entertainment system, perfect for alfresco movie nights. This home boasts a brand new roof with lifetime warranty! Stroll to lovely downtown Oakville, trendy Kerr Village, Tannery Park along the Lake & waterfront trails. Close proximity to highly esteemed schools.

235 LAKEWOOD Drive, Oakville

$2,850,000

4 Beds ⋅ 3 Baths ⋅ W13672736 MLS

Nestled in the heart of the coveted Morrison neighbourhood, this classic residence sits on an expansive, mature 100 x 150 foot lot within the prestigious Ennisclare Park pocket. Steps from the lake and Gairloch Gardens, this impeccably maintained 1960s home still makes a statement. The interior exudes quiet elegance, featuring a wood-panelled family room and a breathtaking sun-room with cathedral ceilings and floor-to-ceiling windows that overlook a lush, private garden oasis. Whether you choose to enjoy its timeless charm, renovate to your taste, or build your dream estate, this is a rare opportunity in one of Oakville's finest school districts

174 Claxton Drive, 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

$3,590,000

5 Beds ⋅ 4 Baths ⋅ W13669660 MLS

Spectacular 2/3-acre premium lot in South East Oakville's highly coveted private crescent. Thoughtfully designed for both refined family living and multi-generational flexibility, this beautifully renovated residence blends contemporary architecture, sophisticated finishes, and an impressive resort-style setting. At the heart of the home is the sleek Top Notch kitchen, featuring high-gloss white cabinetry, marble backsplash, an oversized 12+ feet long white Caesarstone central island, and premium appliances. The elegant living room is anchored by a linear fireplace and striking glass-enclosed wine cellar, creating a sophisticated setting for entertaining. The luxurious primary suite features a spa-inspired ensuite with heated floors, floating contemporary cabinetry, and a walk-in glass shower. Heated flooring extends through all bathrooms, the mudroom, and laundry room, adding comfort and quality throughout. A rare highlight is the fully self-contained 2-bedroom in-law suite, complete with a separate entrance, private kitchen, laundry, and bathroom-ideal for extended family, guests, or live-in support. The main residence is filled with natural light, including a stunning glass-enclosed breakfast area that overlooks the expansive grounds. Outside, the extraordinary grounds offer a true private retreat with an in-ground saltwater pool, hot tub, mini-golf area, mature landscaping, and exceptional privacy. Fully renovated to create a fresh, airy, contemporary feel, this one-of-a-kind home also enjoys a functional family-friendly layout and is within walking distance to some of Oakville's top-rated schools. A rare opportunity to own a truly distinctive residence on one of South East Oakville's most coveted large estate lots.

2076 GLENFOREST Crescent, Oakville

$3,199,000

6 Beds ⋅ 6 Baths ⋅ W13668526 MLS

Remarkable custom-built (2023) contemporary residence on an expansive irregular 76' x 143' lot in sought-after West Oakville, offering 4+2 bedrooms, 6 bathrooms and a professionally finished walk-up basement. Ideally located within walking distance to Brookdale Park & outdoor pool, St. Nicholas Catholic Elementary School, Kinoak Arena, library and Thomas A. Blakelock High School, with Coronation Park, Lake Ontario, YMCA, Appleby College and major highways minutes away. Bold stone, wood & glass exterior, stone-edged double driveway with parking for 6, attached double garage with inside entry and beautifully landscaped private rear yard with large deck, stone patio, glass railings, soffit lighting and side golf green. Exceptional construction standards and designer finishes throughout include European white oak engineered hardwood, imported Italian tiles, custom cabinetry, wall mouldings, wood-slat feature walls, designer lighting, premium plumbing fixtures and ceilings ranging from 9' to 20'. Advanced smart-home technology includes Alexa HVAC, lighting & sprinkler controls, smart locks, MyQ garage remotes, DMSS security system, built-in speakers and some automated blinds/curtains. The sophisticated open-concept main floor features an expansive living room, dining room, custom chef's kitchen, family room and office. Upstairs offers four bright bedrooms, three luxurious bathrooms and laundry, including a spectacular primary suite with custom organizer and 5-piecehotel-like ensuite; one of the additional bedrooms features its own 3-piece ensuite, ideal as a second primary suite. The walk-up lower level delivers exceptional versatility with a large recreation room, two bedrooms, two full bathrooms, second kitchen, second laundry and abundant storage. A distinctive West Oakville residence where innovative architecture, luxury finishes and cutting-edge technology unite.

564 Stonecliffe Road, Oakville

$3,258,000

6 Beds ⋅ 6 Baths ⋅ W13663186 MLS

Some homes make a statement the moment you arrive. Others reveal themselves gradually, each space uncovering another layer. This remarkable residence does both. Set on a premium ravine lot backing onto mature woodland and walking trails, extensive custom stone landscaping frames both the front and rear gardens, creating an arrival that offers little hint of what awaits within. Step inside and the experience begins. A sculptural floating staircase, soaring 10-foot ceilings and expansive European windows draw your attention to the wooded ravine beyond. Scandinavian-inspired interiors, wide-plank white oak floors, dramatic slab feature walls and bespoke millwork create a calm contemporary aesthetic where architecture, craftsmanship and nature exist in perfect balance. At the heart of the home, an exceptional chef's kitchen is anchored by a dramatic natural quartzite waterfall island, beautifully crafted cabinetry, integrated appliances and thoughtful design that brings everyday living and effortless entertaining together. Upstairs, generous family accommodation gives way to a private primary retreat. A dramatic three-sided fireplace, bespoke walk-in dressing room with custom Italian cabinetry and a beautifully appointed spa-inspired ensuite create a peaceful sanctuary at the end of each day. The finished lower level expands the home's possibilities with a private theatre and recreation lounge, together with a beautifully finished legal two-bedroom secondary suite featuring its own entrance, full kitchen, separate laundry and oversized windows. Ideal for multigenerational living, extended family, guests or supplementary income, it offers exceptional flexibility without compromise. Beautifully conceived inside and out, this is a home where exceptional design serves everyday living rather than demanding attention. Some homes are admired for their finishes. Rare ones, like this, are remembered for how they make you feel.

197 Polly Drive, Oakville

$3,088,888

6 Beds ⋅ 5 Baths ⋅ W13658672 MLS

Welcome to this bright and well-maintained home with 5-bedroom, 5-bathroom and over 4,600sf living space on a 100x151.76ft premium lot in Oakville's prestigious Eastlake community. Set on a quiet, tree-lined street surrounded by mature trees, just steps to top-ranked schools (Oakville Trafalgar High School and Maple Grove Public School)The functional main floor features formal living and dining rooms, a private office, and an open-concept kitchen, spacious breakfast area and family room with a fireplace overlooking the backyard. Multiple windows and skylights fill the space with natural light, while multiple walkouts lead to the covered porch, professionally landscaped backyard and inground pool. The kitchen features a large centre island and was refreshed in 2026 with new countertops, refrigerator, stove and range hood.Interior doors and door frames on the main and second floors were also replaced in 2026. A mudroom, laundry room and powder room complete the main level.The second floor offers a practical and well-designed layout with five bright, generously sized bedrooms and three bathrooms, including a spacious primary suite with a private ensuite and walk-in closet. The thoughtful arrangement provides excellent comfort and functionality for family living.The finished walk-up basement with a separate entrance offers exceptional flexibility and is divided into two distinct living areas. One side features a spacious recreation room with a fireplace and wet bar, while the other includes a second kitchen, bedroom, three-piece bathroom, separate laundry and direct access to the backyard. With two kitchens, two laundry areas and a flexible layout, the home is ideal for a large or multigenerational family, with excellent potential for extended family or secondary living arrangements.Additional updates include the roof in 2018 and furnace in 2025. A rare opportunity combining space, functionality, location, a premium lot and outstanding future potential. Must to see!

244 Colchester Drive, Oakville

$2,999,900

2 Beds ⋅ 3 Baths ⋅ W13658162 MLS ⋅ The Randall BLDG.

Experience an exceptional standard of luxury in this rare penthouse at The Randall Residences, Oakville's most prestigious boutique condominium. Reserved exclusively for the penthouse level, soaring 12-foot ceilings, exquisite custom millwork, and refined finishes create an atmosphere of timeless elegance. A grand circular stone floor foyer welcomes you into this beautifully designed residence, complete with a spacious front hall closet, powder room, and an generous walk-in laundry room with laundry sink. The spectacular open-concept kitchen is the heart of the home, featuring a generous centre island, marble countertops, premium appliances, and seamless flow into the dining area with custom built-in pantry cabinetry. The living room is framed by floor-to-ceiling wraparound windows that flood the space with natural light, while custom built-ins and a striking fireplace provide warmth and sophistication. Step onto the private south-facing balcony to enjoy sunny views and effortless indoor-outdoor living. The luxurious primary retreat offers a beautifully appointed dressing room and a spa-inspired five-piece marble ensuite. The second bedroom is equally impressive with floor-to-ceiling south-facing windows, a generous closet, and its own private three-piece ensuite. With only 32 exclusive residences, The Randall offers unparalleled privacy and service, including 24-hour concierge, three elevator banks, impeccably maintained underground parking with soaring ceilings, two premium parking spaces, and a private locker. Perfectly situated in the heart of downtown Oakville, you're just steps from the lake, boutique shopping, cafés, fine dining, and the renowned Sotto Sotto restaurant located on the main floor. A truly exceptional opportunity to own one of downtown Oakville's most distinguished penthouse residences.

300 Randall Road Unit PH5, Oakville

$3,750,000

5 Beds ⋅ 5 Baths ⋅ W13658150 MLS

Elegant 5-bedroom family home sitting on 0.346 acres on coveted Birch Hill Lane. This quiet and exclusive cul-de-sac south of Lakeshore is just steps to the Lake and Appleby College. Thoughtfully designed with a West Coast flare, this home offers 4336 sf above grade plus a fully finished 2400 sf lower level with separate entrance. Designed for entertaining, the main level features a formal living room with gas fireplace, separate dining room, and a secluded main floor office. The open concept kitchen offers a large centre island, built-in appliances and a rounded breakfast nook overlooking the back gardens. An inviting sunken family room with gas fireplace and custom cabinetry is the perfect end-of-day retreat. A main floor laundry room and powder room complete the main level. Direct access to the 2-car garage. Separate entrance to the lower level from the garage. Upstairs hosts a luxurious primary suite with separate sitting area, walk-in closet and a 5-pc ensuite. 4 additional bedrooms and 2 bathrooms complete the upper floor. The lower level is vast and offers large recreation room, lounge with wet bar, wine cellar, and an exercise room with adjoining spa. A true zen getaway, the 6-pc spa features a freestanding tub, double vanities and a separate steam shower perfect for post workout recovery. The professionally landscaped grounds offer multiple lounging and entertaining areas and is exceptionally private with the green space behind. Ideally located next to top-ranked schools, the lake and a short stroll to all that downtown Oakville has to offer. The perfect enclave for your family to call home.

56 Birch Hill Lane, Oakville

$2,999,000

4 Beds ⋅ 4 Baths ⋅ W13647310 MLS

Welcome to this exceptional custom-built bungaloft, thoughtfully owner-designed and completed in 2010, where timeless craftsmanship, luxurious finishes, and an unparalleled setting backing onto Sixteen Mile Creek come together to create a truly one-of-a-kind home. Offering 3 spacious bedrooms and a highly desirable main floor primary suite, this residence has been meticulously designed with no detail overlooked. The primary retreat features a luxurious 6-piece ensuite and a walkout to a private backyard oasis, creating the perfect space to begin and end each day. The heart of the home is the stunning custom kitchen, complete with soapstone countertops, a large centre island, built-in bench seating for relaxed family breakfasts, custom cabinetry with abundant storage, elegant chandeliers, and premium finishes throughout. The kitchen flows seamlessly into the impressive family room, highlighted by soaring vaulted ceilings open to the second level, creating an inviting space for everyday living and entertaining. A walkout leads to the expansive deck overlooking the beautifully landscaped backyard and saltwater pool. Exquisite architectural details, including wrought iron railings throughout, custom millwork, and quality craftsmanship, elevate every room. Main floor laundry adds everyday convenience. The fully finished lower level is designed for entertaining and relaxation, featuring a spacious recreation room overlooked by a full wet bar, games room, exercise room, and a spa-inspired 5-piece bathroom, offering the perfect extension of the home's living space. Backing onto the natural beauty of Sixteen Mile Creek, this remarkable property provides exceptional privacy, scenic views, and a tranquil setting rarely found. Move in, relax, and enjoy luxury living with nothing left to do but unpack.

379 River Side Drive, Oakville

$2,649,000

5 Beds ⋅ 5 Baths ⋅ W13646260 MLS

Prestigious Joshua Creek! Exceptional 5 Bed, 5 Bath executive home with over 5,000 sqft of finished living space. Park directly in front and private ravine lot with access to scenic trails. Safe walking distance to top-rated schools (K-G8) - enjoy the rare comfort of watching your children walk to and from school. Main floor features 15-ft ceilings in the living room, private office, formal dining, and open-concept kitchen with unique LG Viatera Quartz counters, Blum push-open cabinetry, upper pull-down storage, and all-new Dacor appliances (2023): 36" hood fan, 36" professional range, 42" built-in fridge, built-in microwave & dishwasher. Walk-out to upper deck overlooking ravine. Hardwood floors throughout main level. Upper level offers 5 bedrooms with ensuite access. Primary retreat with 5-pc ensuite, Jacuzzi tub & 2 walk-in closets. Two Jack & Jill baths serve remaining bedrooms. Fully finished walk-out basement with gas fireplace, bar, pool table area, dance/exercise space, sauna room, 3-pc bath & direct yard access. Landscaped yard with sprinkler system, gas BBQ hookup. Outdoor furniture, pool table & guest room bed included. Extensive updates include: All-new Dacor kitchen appliances (2023) New Whirlpool washer & dryer (2023) Front entry door & patio door replaced (2023) Windows resealed and recaulked (2023) Backyard drainage improvements (2023) Outdoor lighting installed (2023) Roof maintenance (2024) Deck replaced( 2026)

1516 Pinery Crescent, Oakville

$3,900,000

W13626230 MLS

Standalone building with on-site parking, extra land/yard space offering excellent signage/exposure. Major renovation in 2020, including new roof, windows, electrical, furnace, kitchen, bathroom etc. Flexible zoning permits a wide variety of uses. Immediate access to the QEW/403/407. Close proximity to numerous retail amenities including Farm Boy, Starbucks and many others.

2078 Upper Middle Road E, Oakville

$3,900,000

W13626156 MLS

Standalone building with on-site parking, extra land/yard space offering excellent signage/exposure. Major renovation in 2020, including new roof, windows, electrical, furnace, kitchen, bathroom etc. Flexible zoning permits a wide variety of uses. Immediate access to the QEW/403/407. Close proximity to numerous retail amenities including Farm Boy, Starbucks and many others.

2078 Upper Middle Road E, Oakville

$2,999,000

3 Beds ⋅ 4 Baths ⋅ W13625136 MLS

Lakefront, large and very spacious, freehold townhouse, rarely offered, in prestigious Bronte with unobstructed, panoramic views of Lake Ontario. One of only a select few waterfront residences in this exclusive enclave and seldom available, this exceptional townhouse is offered for the first time and has been professionally renovated from the ground up, representing a complete rebuild with all-new systems, infrastructure, and bespoke designer finishes throughout. Thoughtfully reimagined with refined architectural detail, the residence showcases a dramatic custom staircase, sun-filled open-concept living spaces, and expansive windows that frame breathtaking lake views from multiple levels. Seamless indoor-outdoor flow creates an unparalleled waterfront living experience rarely available in townhouse ownership. The designer kitchen features custom cabinetry and premium appliances, including a high-end stove with oven, range hood, microwave, dishwasher, and refrigerator, curated for elevated everyday living and elegant entertaining. Engineered hardwood flooring extends throughout, complemented by heated bathroom floors and three fireplaces, including two gas fireplaces and an electric fireplace in the private primary suite. The spa-inspired primary ensuite features a steam shower. The third bedroom offers flexibility to be a family room (presently used as one). Basement office/den has multiple uses. Two private waterfront decks, including an impressive 40-ft deck(approx.) on the main and a fully covered one on the third floor, provide exceptional outdoor living and spectacular sunset views. Located in one of Oakville's most coveted waterfront communities with private tennis courts, just steps to Bronte Harbour, marina, waterfront trails, fine dining, and boutique shops. A truly rare turnkey lakefront offering.

10 Southwind Terrace, Oakville

$3,498,000

4 Beds ⋅ 5 Baths ⋅ W13611774 MLS

Welcome to 1551 Warland Rd, a stunning custom-built bungaloft in the heart of highly sought-after South Oakville. Nestled just a 5-minute walk from Coronation Park and the serene shores of Lake Ontario, this exceptional residence offers over 5,700 square feet of meticulously finished living space, blending luxury, comfort, and modern convenience. Step inside to discover an inviting main floor where primary rooms exude elegance with coffered ceilings, expansive picture windows flooding the space with natural light, and rich hardwood flooring. The gourmet kitchen is a chefs dream, featuring top-of-the-line JennAir appliances, including dual dishwashers, a gas stove with a custom hoodfan, side-by-side fridge, built-in oven, and microwave. A butlers pantry and servery seamlessly connect the kitchen to the dining room, perfect for effortless entertaining. The bathrooms elevate luxury with quartz countertops, undermount sinks, sleek glass shower enclosures, and heated flooring for year-round comfort. The primary suite, conveniently located on the main level, offers a tranquil retreat with sophisticated finishes and ample space. Downstairs, the lower level impresses with a custom wet bar and wine room, ideal for hosting guests, alongside a dedicated exercise room for your wellness needs. Every detail has been thoughtfully designed to enhance your lifestyle. Step outside to the backyard oasis, where an outdoor patio steals the show with a custom pizza oven, built-in barbecue, and a covered area featuring a cozy fireplace perfect for al fresco dining or relaxing evenings under the stars. Located in one of Oakville's most desirable neighborhoods, this bungaloft combines timeless craftsmanship with modern amenities, all just steps from parks, lakefront trails, and the vibrant South Oakville community.

1551 Warland Road, Oakville

$3,099,900

5 Beds ⋅ 5 Baths ⋅ W13598106 MLS

1077 Bridge Road offers over 5,300 sq. ft. of finished living space on a landscaped 100' x 120' lot in sought-after West Oakville, minutes to downtown Oakville, Bronte Harbour, Lake Ontario, parks, the YMCA, top-rated schools, and Appleby College. A grand foyer with 10-foot ceilings, plaster crown moulding, and a hardwood staircase leads to a private office, formal dining room, and butler's servery with wine fridge. Wide-plank hardwood floors, 9-inch baseboards, custom millwork, coffered ceilings, and a gas fireplace complement the open-concept living space. The chef's kitchen features Sub-Zero, Wolf, and Bosch appliances, a large island, and breakfast area. The second level offers four bedrooms with ensuite access, including a primary suite with a walk-in closet and a heated-floor ensuite. A second bedroom has a private ensuite, while two others share a Jack-and-Jill bath. Second-floor laundry adds convenience. The finished lower level features heated floors, a spacious rec room with a stone gas fireplace, fifth bedroom, 3-piece bath, and flexible space for a gym, media room, or games area. Outside, enjoy a covered porch, stone patio, landscaped backyard with irrigation, Generac whole-home generator, security system, and epoxy-finished double garage. A custom-built home combining quality craftsmanship, functional design, and an exceptional West Oakville location.

1077 Bridge Road, Oakville

$3,498,000

4 Beds ⋅ 5 Baths ⋅ W13593236 MLS

Tucked away on a quiet dead-end crescent on one of Bronte's best streets, this custom-built home blends thoughtful design and family-friendly living. It is steps from a park and playground, and within walking distance of Bronte's renowned restaurants, waterfront, and marina. Offering over 3,500 square feet above grade, plus a newly finished basement (2026), every inch has been designed for everyday living and effortless entertaining. A formal foyer creates a beautiful first impression, opening to an elegant living room and private main floor office.The heart of the home is an impressive chef's kitchen with premium appliances, an oversized centre island, and exceptional storage. A butler's pantry seamlessly connects the kitchen to the walk-in pantry and formal dining room. A generous breakfast area flows into the inviting family room, featuring a warm gas fireplace.Designed as an extension of the living space, the professionally landscaped backyard was transformed by ProScape Land Design into a private outdoor retreat. It features a covered dining area with a built-in BBQ, tiered seating beneath a pergola, and a private putting green.Upstairs, the layout offers privacy for everyone. The primary suite is a true retreat with a spa-inspired ensuite and a spacious walk-in closet. Two secondary bedrooms share a beautifully appointed Jack-and-Jill bathroom, while the fourth bedroom enjoys its own private ensuite.The newly completed lower level expands the living space with beautifully finished recreation areas, a custom built-in bar with beverage and wine refrigerators, a wine display, extensive built-in cabinetry, a dedicated home gym, and a convenient two-piece bathroom.From its exceptional custom design and family-friendly layout to its magazine-worthy backyard and unbeatable Bronte location, this home is a fantastic opportunity in one of Oakville's most cherished neighbourhoods.

2458 Meadowood Crescent, Oakville

$3,450,000

5 Beds ⋅ 5 Baths ⋅ W13548392 MLS

Exceptional contemporary family home on a premium 87x 179 southwest lot on one of Southeast Oakville's most sought-after streets, just steps to top-ranked public schools and prestigious private schools including Linbrook School & St. Mildred's-Lightbourn School. Offering over 5,000 sq. ft. of beautifully finished living space, this impressive residence offers modern design and exceptional family functionality. A generous foyer creates a stunning first impression, with sightlines extending through the home to the beautifully landscaped rear gardens. Professionally designed outdoor living features extensive hardscaping, an inground pool, hot tub, covered gazebo, fire pit zone, and landscape lighting, creating a private resort-like setting for entertaining and family enjoyment. The thoughtfully designed layout offers 4+2 bedrooms and 3+2 bathrooms. All bedrooms feature built-in closets, while the primary generous suite boasts dual walk-in closets and a spa-inspired ensuite with double vanity, soaker tub, and separate shower. The heart of the home is a stunning contemporary kitchen overlooking the spacious family room with a gas fireplace and wall of sliding glass doors opening to the private backyard oasis. Elegant principal rooms include a formal living room with fireplace and oversized windows, a separate dining room, a dedicated main floor office, and a well-appointed mudroom with inside access to the attached two-car garage.The fully finished lower level includes a spacious rec room with gas fireplace, adjoining billiards area, two additional bedrooms, a sauna, laundry room with second refrigerator, direct access to the side yard-ideal for guests, extended family, or recreation. Nestled on one of Southeast Oakville's most desirable streets, this exceptional property offers the charm and tranquility of an established neighbourhood with mature trees, beautiful parks, and convenient access to lakeside parks and Downtown Oakville.

1179 Carey Road, Oakville

$2,599,999

5 Beds ⋅ 4 Baths ⋅ W13528872 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 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-paneled 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.

104 Whittington Place, Oakville

$4,999,000

4 Beds ⋅ 5 Baths ⋅ W13524820 MLS

Grand Grounds. Timeless Elegance. Extraordinary Potential.An exceptional opportunity in one of Olde Oakville's most prestigious neighbourhoods. Tucked behind private gates and nestled beneath a magnificent canopy of mature trees, this beautifully landscaped and increasingly rare 0.82-acre estate offers over 7,100 square feet of living space in an irreplaceable setting just moments from Downtown Oakville.Approached by a sweeping circular drive, the timeless brick residence immediately impresses with its classic Colonial Williamsburg-inspired architecture, elegant symmetry, and commanding presence. Beyond the front entrance, peaceful views of the private pond and lush landscape create a tranquil, park-like retreat rarely found in such a coveted urban location.Custom built in 1980, this stately four-bedroom residence offers an extraordinary opportunity to reimagine an exceptional property. Offered in "as is" condition, the home presents the perfect canvas for those looking to undertake a significant renovation, thoughtfully restore its timeless character, or explore the opportunity to create a magnificent custom estate (subject to all necessary approvals). Whether preserving its enduring architectural charm or designing an entirely new vision, the possibilities are truly exceptional.The expansive grounds provide an incredible backdrop for family living, entertaining, and creating lasting memories for generations to come. Properties offering this rare combination of land, privacy, scale, and location are becoming increasingly difficult to find.Ideally situated within one of Oakville's most sought-after school districts and just a short walk to Downtown Oakville, the Oakville GO Station, public and private schools, Post Park, Whole Foods, Longo's, boutique shopping, restaurants, and the lakefront, this is more than an exceptional property-it is a rare opportunity to create a legacy estate in one of Olde Oakville's most coveted locations.

488 Macdonald Road, Oakville

$4,895,000

4 Beds ⋅ 4 Baths ⋅ W13519952 MLS

Welcome to 1516 Duncan Road, an extraordinary custom-built contemporary residence in prestigious Southeast Oakville where exceptional craftsmanship and state-of-the-art smart home technology come together seamlessly. Completed in 2020, this one-of-a-kind bungalow offers 5,000 sq. ft. of living space with 3+1 bedrooms, 4 bathrooms, and a residential elevator servicing all three levels, including the rooftop terrace. Soaring 15-ft floor-to-ceiling windows flood the open-concept interior with natural light while creating a seamless connection to the landscaped backyard featuring extensive hardscaping, an outdoor gas fireplace, heated outdoor living areas, and exceptional privacy. Polished concrete floors with hydronic radiant heating, custom cabinetry, and natural stone finishes define the sophisticated interior. The designer kitchen is equipped with Thermador and Bosch appliances, Brazilian Black Fusion stone countertops, double ovens, a barista station, and a wet bar featuring Grohe Blue chilled, sparkling, and filtered water. The tranquil primary suite overlooks a private bamboo courtyard and offers custom built-ins and a luxurious spa-inspired ensuite. The finished lower level is designed for entertaining with a games area, wet bar featuring Avocatus quartzite, dedicated home theatre, guest suite, and family room. Smart living is elevated through Lutron lighting, Home Assistant automation, Sonos audio, a 24-camera surveillance system, fibre internet with Starlink backup, motorized shutters, and whole-home smart leak protection. Highlights include a heated driveway, walkways and covered porches with integrated snow-melt system, oversized double garage with EV charger, central vacuum, smart irrigation, and low-maintenance landscaping. A truly exceptional residence blending innovative technology, timeless design, and uncompromising luxury in Oakville's most sought-after neighbourhoods.

1516 Duncan Road, Oakville

$3,890,000

4 Beds ⋅ 5 Baths ⋅ W13512502 MLS

Nestled on an exceptional 15,511sqft mature lot in prestigious Southeast Oakville, this beautifully renovated executive residence offers timeless elegance, luxurious finishes, and an unbeatable location within walking distance to top-ranked schools, including OTHS, EJ PS etc. Offering approximately 3487 sqft. above grade plus a finished lower level, this exceptional home features 4 bedrooms, 5 bathrooms, and thoughtfully designed living spaces perfect for both family living and entertaining.Rich wide-plank hardwood floors, crown mouldings, custom millwork, wainscoting, built-ins, pot lights, stone flooring, an impressive oak staircase with iron pickets, and four gas fireplaces showcase the home's exceptional craftsmanship. The stunning renovated chef's kitchen is appointed with premium Miele appliances, custom cabinetry, and overlooks the inviting sunken family room, creating the perfect gathering space. Elegant formal living and dining rooms provide refined spaces for entertaining, with the living room easily accommodating a baby grand piano.The luxurious primary retreat features its own gas fireplace, an expansive dressing room, and a spa-inspired 4-piece ensuite with a glass shower. The finished lower level offers a spacious recreation room, exercise room, 2-piece bath, and abundant storage.Extensive updates include a complete kitchen renovation, premium Miele appliances, exterior LED lighting, renovated garage, repaved driveway, new eavestroughs, freshly painted exterior façade, new pool liner and heater, and numerous quality improvements throughout.The spectacular backyard is a private oasis featuring a sprawling stone patio, covered terrace, and sparkling in-ground pool surrounded by mature landscaping-perfect for summer entertaining. Ideally located just steps to Lake Ontario, Gairloch Gardens, parks, trails, and only a 3-minute drive to downtown Oakville's boutique shops, fine dining, and waterfront.

153 Cairncroft Road, Oakville

$4,399,000

6 Beds ⋅ 8 Baths ⋅ W13466488 MLS

Unparalleled elegance define this exquisite luxury detached home featuring 5 + 1 bedrooms and 8 washrooms in the prestigious Bronte West community of Oakville, offering over 5,000 sq. ft. of sophisticated living space with exceptional design and premium finishes throughout. The home welcomes you with a double door entry leading into a dramatic foyer with a 22' open-to-above ceiling, 11' across and 12' in basement. Separate living and dining areas are complemented by large windows, while the impressive family room boasts a 22' open-to-above ceiling, a gas fireplace, and expansive window. The main floor also includes a mud room for added practicality, seamlessly connecting the garage entry to the living spaces.The gourmet kitchen is equipped with built-in SS appliances, a pantry, a servery, and a breakfast area combined with the kitchen, with a walk-out to a terrace ideal for entertaining large gatherings. A private elevator, connecting all levels of the home with ease and comfort.The second floor offers a luxurious primary suite featuring his-and-her closets with a skylight and a 5-piece ensuite with dual sinks, while 4 additional spacious bedrooms each include their own closets and private ensuites, along with a second-floor laundry for added functionality. The fully finished walk-out basement includes a 1-bedroom suite, 2 bathrooms, a recreation room with wet bar that can be converted into a second kitchen, a home gym and a dedicated home theatre for entertainment, along with a cold room, plus a second laundry area in the basement for added convenience. The beautifully landscaped backyard creates a resort-style setting perfect for relaxation and entertaining. Ideally located just minutes from Coronation Park, the lakeshore, top-rated schools, fine dining, boutique shopping, and cultural amenities. Taxes have not been assessed yet.

1042 Bridge Road, Oakville

$3,739,000

5 Beds ⋅ 6 Baths ⋅ W13444624 MLS

Nestled in the heart of highly sought-after Morrison, this exceptional custom-built executive home offers 4,464sf above grade or nearly 6,000 sf of refined luxury living space, set on a rare 100 x 150 ft south-facing premium lot. Thoughtfully designed with a contemporary aesthetic and impeccable craftsmanship, this residence seamlessly blends elegance with modern functionality.Featuring a versatile layout with 2 bedrooms on the main level and 2 on the upper level, all spacious and boasts its own private ensuites and spacious walk-in closets, offering ultimate comfort and privacy. The home showcases rich hardwood flooring throughout, complemented by custom slatted wood accent walls, extensive millwork, crown mouldings, and soaring ceilings that elevate the sense of space and sophistication.The heart of the home is the breathtaking double-height family room, highlighted by floor-to-ceiling windows, and a dramatic walnut slatted feature wall-creating a true architectural statement. Walk out to a 650 sq.ft. oversized deck, perfect for seamless indoor-outdoor entertaining.The designer kitchen is a chef's dream, featuring premium cabinetry, granite countertops, and top-of-the-line appliances, flowing effortlessly into the principal living spaces. A dedicated main floor office adds convenience for modern living.The professionally finished lower level offers expansive recreation and entertainment areas, ideal for family gatherings or hosting guests.Outdoors, enjoy beautifully landscaped front and rear gardens with a full sprinkler system, interlocking stonework, and a private backyard retreat bathed in southern sunlight.Located just steps to top-ranked schools (Oakville Trafalgar High School, Maple Grove Public School) and the lake, parks, and downtown Oakville, this home represents a rare opportunity in one of Oakville's most prestigious enclaves.

1508 Oakhill Drive, Oakville

$2,999,999

2 Beds ⋅ 3 Baths ⋅ W13439412 MLS ⋅ The Coventry BLDG.

Welcome to The Coventry Penthouse-one of downtown Oakville's most distinguished luxury residences. This architecturally significant suite, designed by acclaimed architect Bill Hicks, offers an unparalleled lifestyle just steps from the lake, waterfront parks, shopping, and dining. Occupying a premier position within this exclusive boutique building, the penthouse delivers exceptional privacy and sophistication. Expansive living spaces are highlighted by soaring ceilings, a dramatic skylight, custom Downsview kitchen, walk-in pantry, formal dining room, integrated Sonos sound system, and elegant indoor-outdoor living. Two sets of French doors open to a covered terrace featuring a striking two-sided fireplace, while a spectacular private rooftop terrace creates the perfect setting for entertaining and relaxation. The luxurious primary retreat includes terrace access, a spacious walk-in closet, and spa-inspired five-piece ensuite. Complete with a second bedroom, den (den can be converted to a third bedroom), 2.5 bathrooms, two premium parking spaces, and a locker, this exceptional residence offers the comfort of a custom home with the ease and convenience of luxury condominium living. A rare opportunity to own a truly unique penthouse in the heart of downtown Oakville. *Some photos may be virtually staged

253 Church Street Unit 402, Oakville

$2,899,000

5 Beds ⋅ 4 Baths ⋅ W13215172 MLS

MUSKOKA-LIKE SETTING BACKING ONTO A RAVINE! LUXURY LIVING IN AN EXCLUSIVE ENCLAVE! MAIN FLOOR PRIMARY RETREAT! PROFESSIONALLY FINISHED WALKOUT LOWER LEVEL! Welcome to 1227 Riverbank Way, an exceptional residence in prestigious Valleyview Estates, tucked away at the end of an extremely private cul-de-sac. Upon arrival, you'll be captivated by the striking stone and stucco exterior, natural stone driveway, majestic trees, and lush landscaping. The centrepiece of the main level is the dramatic living room featuring a soaring 15'8 vaulted ceiling with decorative beams and a corner gas fireplace. A chef-inspired Downsview Kitchen with custom cabinetry, granite countertops, designer backsplash, premium stainless steel appliances, centre island, breakfast area, and walkout to the composite deck is ideal for effortless indoor/outdoor living. The rare main floor primary retreat offers a private balcony, vaulted ceiling, gas fireplace, walk-in closet, and spa-inspired five-piece ensuite with double sinks, vanity area, and luxurious soaker tub. Two additional bedrooms and a four-piece bathroom with skylight are located on the upper level. Professionally finished in 2018, the walkout lower level extends the living space even further with an oversized recreation/games area, two bedrooms, three-piece bathroom, and family room with patio access - ideal for multi-generational living. Notable updates include furnace and central air (2023), hardwood flooring throughout the upper level (2018), shingles (2018), and epoxy garage floors (2023). The tranquil backyard oasis showcases an expansive composite deck, natural stone patios and steps, stone benches, extensive river rock, landscape lighting, and the ultimate in privacy. This one-of-a-kind setting is surrounded by an extensive trail network along Sixteen Mile Creek, Lions Valley Park, forests, and greenspace, offering an unparalleled blend of luxury, nature, elegance, and lifestyle. (certain images have been virtually staged)

1227 Riverbank Way, Oakville

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