Quick Oakville ON MLS Search

Browse All Oakville ON 5 Bedroom Properties for Sale

183 Kaitting Trail, Oakville
$1,558,000
5 Beds ⋅ 4 Baths ⋅ W13747176 MLS
Stunning former Remington model home on a premium lot with greenspace at the back and along the side for exceptional privacy.This beautifully appointed home features smooth 9-ft ceilings on both the main and second floors, quartz countertops in the kitchen, bathrooms and laundry room, upgraded hardwood and ceramic flooring, pot lights throughout the principal rooms, kitchen, hallways and primary bedroom, elegant main-floor cornice mouldings, and an oak staircase with wrought-iron pickets. The open-concept kitchen and family room are ideal for entertaining, with under-cabinet lighting, an upgraded chimney-style hood fan, custom built-in banquette seating and a new dishwasher (July 2026). The spacious primary suite offers a walk-in closet and a luxurious ensuite with a frameless glass shower, quartz countertop and designer wallpaper. California shutters and Drapes are featured throughout. The large main-floor laundry room includes quartz counters, upper cabinetry, a utility sink, ample storage, interior garage access, exterior access, and a newer washer and dryer (2025). A brand-new, never rented, legal one bedroom basement apartment offers a separate ground-level entrance, extra-large above-grade windows, a spacious bedroom, private bathroom, separate laundry, quartz counters, built-in cabinetry and generous storage-ideal for income potential (Approx. $2000) or multigenerational living. Enjoy professionally landscaped and hardscaped grounds, a premium stone patio, covered porch with natural gas BBQ hookup, two fruit trees and parking for three vehicles. The garage features an epoxy-coated floor, built-in shelving and a smart opener. Ideally located near schools, with public transit just one block away. Additional street parking is available by permit from the town for approximately $50 per month. A rare opportunity combining luxury finishes, income potential and an exceptional location. (Seller is a registered real estate agent).

183 Kaitting Trail, Oakville

1321 Monks Passage N/A, Oakville
$2,280,000
5 Beds ⋅ 4 Baths ⋅ W13742366 MLS
Luxurious and Renovated 5 Bedrooms + Main Floor Office 3.5 Baths in Prestigious Glen Abbey! This stunning Mattamy 'Yorkshire' model features 3,791 sqft plus an additional 1,200 sqft of finished basement space. Fully transformed and meticulously maintained gem in the top-ranked Abbey Park High School district. Gorgeous dark hardwood floors flow throughout the main and upper levels. smooth ceiling and pot lights thru out main floor. The beautifully renovated dream kitchen boasts solid maple cabinets, gas stove, quartz countertops, breakfast bar, walk-in pantry and chef's desk with with illuminated display cabinets. Gorgeous family room with bow window, wainscoting,limestone fronted fireplace. convenient office on main floor with double door entry. a grand Scarlett O'Hara staircase illuminated by a large skylight leads to the upper floor, where you'll find 5 bedrooms and 3 full bathrooms. The massive primary suite includes a renovated bathroom with a free-standing bathtub, frameless glass shower, double sinks, and a massive walk-in closet. An adjoining bedroom which is open to master bedroom offers flexible and convenient space as a nursery, media room, or second office. renovated Jack-and-Jill bathroom with 2nd skylight.The finished basement, featuring new vinyl flooring, is perfect for entertainment with dedicated game, media w/ gas fireplace and exercise rooms. over 530sf unfinished storage room for all your stuff. entire house is freshly painted. Escape to your private summer retreat, featuring a refreshing 18'x36' pool with new pool heater and pump(23) and a deep diving end, an interlocking patio, a charming muskoka rock garden, and fruit trees and bushes including Raspberry, Prune and Peach. **EXTRAS** freshly painted(24),bsmt vinyl flooring(24),renewed kit.(24),W/D(23), pool pump(23),pool heater(23),Attic insulation(22), flooring & three bathrooms (16), Windows14, Roof 12, Pool Rebuilt13, Furnace W Hepa Filter 00/10, Ac 05.

1321 Monks Passage N/A, Oakville

10 Brookfield Road, Oakville
$10,900,000
5 Beds ⋅ 4 Baths ⋅ W13738344 MLS
Situated on just over half an acre on the shores of Lake Ontario, 10 Brookfield Road is a truly exceptional waterfront property offering an extraordinary combination of views, privacy, recreation and year-round enjoyment. With unobstructed vistas of Lake Ontario from virtually every angle, the setting is as captivating as it is rare. The property's exceptional waterfront experience begins with riparian rights- the ultimate in waterfront living - and is highlighted by a detached boathouse with dedicated boat storage and a marine rail. Above, a spacious viewing deck and built-in gazebo create an ideal setting for entertaining, intimate gatherings, a lakeside bar or live music, all overlooking breathtaking panoramic views of the lake. Beyond the waterfront, an in-ground swimming pool and pool house with change rooms create a private, resort-like environment for summer entertaining and relaxed days at home. A parkette immediately to the east adds an exceptional sense of privacy, openness and seclusion rarely found in such a prominent waterfront setting. The natural topography creates distinct elevations and vantage points, allowing the home and outdoor spaces to fully embrace the lake. Inside, the spacious great room is designed for both everyday living and entertaining, complemented by an updated kitchen, walkout lower level and expansive windows that flood the home with natural light and showcase the views. Multiple walkouts provide seamless access to generous decks and outdoor entertaining spaces. Ideally located in close proximity to Lakeshore and Kerr Village, the property is also only a 15-minute walk to Downtown Oakville, offering convenient access to shops, restaurants, cafes and the vibrant village atmosphere. Whether enjoying a quiet morning overlooking the water, hosting friends poolside or launching a boat from the boathouse, 10 Brookfield Road is a truly rare waterfront offering. Luxury Certified.

10 Brookfield Road, Oakville

2372 Carrington Place, Oakville
$5,399,000
5 Beds ⋅ 5 Baths ⋅ W13729598 MLS
WATERFRONT PROPERTY! Experience the Potential of Lakeside Living. Perfectly situated on a premium 90' x 152' lakefront lot, this residence offers breathtaking, unobstructed water views from every principal room. With over 5,700 square feet of finished living space, the home presents an exceptional opportunity to bring your vision to a truly remarkable waterfront setting. The existing layout offers generous space for family living and entertaining, with rich hardwood flooring, limestone tiles, four skylights, two spacious family rooms, a private office, and a large kitchen with lake views! Upstairs, four generously sized bedrooms provide excellent space and privacy, while the primary suite showcases spectacular lake views. A convenient upper-level laundry room and walkout to the second-floor terrace offer additional potential to create a beautiful retreat overlooking the water. The fully finished lower level includes a fifth bedroom with a private ensuite, ideal for guests, extended family, or a nanny suite. Outdoors, the property offers an incredible foundation for creating your own waterfront oasis. The views, privacy, and ever-changing beauty of the waterfront truly have to be experienced to be fully appreciated, as the changing seasons, light, and skies create a new view from moment to moment. Additional highlights include a three-car garage, four fireplaces, an irrigation system, and ample storage throughout. This is a rare opportunity to transform an expansive waterfront property into a spectacular lakeside home, while enjoying the privacy, scale, and extraordinary setting that cannot be replicated. Luxury Certified.

2372 Carrington Place, Oakville

6 Ennisclare Drive W, Oakville
$13,500,000
5 Beds ⋅ 6 Baths ⋅ W13723478 MLS
Designed by architect Gren Weis and built by Lakehurst Construction, this exceptional custom estate is beautifully positioned on the shores of Lake Ontario in one of South-East Oakville's most prestigious waterfront enclaves. Set on a remarkable property with coveted riparian rights, the residence offers breathtaking lake views, exceptional privacy, and a seamless blend of timeless architecture and modern luxury.Classical proportions and outstanding craftsmanship are showcased throughout, with intricate millwork, detailed ceilings, radiant heated floors, and upgraded lighting. Generous principal rooms are thoughtfully positioned to maximize sweeping water views. The main level features a magnificent living room with double French doors opening to the lake breeze, a light-filled solarium overlooking landscaped gardens, an elegant dining room, and a gourmet kitchen with professional-grade appliances and dedicated prep kitchen. A sun-filled family room with striking waffle ceilings completes the space. Upstairs, the serene primary retreat offers spectacular views, a spa-inspired ensuite, and beautifully appointed dressing room. Three additional bedrooms, two elegant bathrooms, and a sophisticated lake-view library complete the level.The lower level offers full-size windows, radiant heated floors, a recreation room with wet bar, fitness studio with full bathroom, private guest suite with ensuite, and extensive storage. Outside, manicured gardens flow naturally toward the shoreline, creating a private waterfront setting designed to be enjoyed throughout the seasons. Multiple walkouts provide effortless access to the grounds and lake, where morning paddleboarding, or an evening canoe launch can become part of everyday life. Steps from Gairloch Gardens and minutes from Downtown Oakville's boutiques, restaurants, cultural amenities, and highly regarded schools, this extraordinary estate offers the very best of South-East Oakville waterfront living

6 Ennisclare Drive W, Oakville

3200 Ernest Appelbe Boulevard, Oakville
$1,699,999
5 Beds ⋅ 5 Baths ⋅ W13717066 MLS
Welcome to 3200 Ernest Appelebe Blvd, a beautifully maintained detached home only 9 years old, offering an impressive 3,369 sq.ft of above-grade living space plus a full basement and double-car garage. Featuring a rare and highly desirable 2-storey + loft layout design, this exceptional home offers an abundance of space and flexibility for modern family living. With 9-ft ceilings on both the main and second floors, this home feels a bright, open and spacious throughout. The upgraded kitchen(2022) features modern finishes, quartz countertops and backsplash, creating both style and functionality for everyday living and entertaining. Dual-zone HVAC with separate temperature controls for the main/basement and second floor/loft, providing enhanced comfort throughout the home. The second floor is thoughtfully designed with four spacious bedrooms and three full bathrooms-two bedrooms feature their own ensuites, while the other two share a bathroom, offering an ideal layout for family living. The expansive third-floor loft, completed with its own full bathroom, is a standout feature of this unique floor plan and provides exceptional flexibility-perfect as a fifth bedroom, home office, media room, guest suite or private retreat. Ideally located in Oakville's sought-after Glenorchy community, with convenient access to shopping, parks, schools and major highways. A rare opportunity to enjoy over 3,300 sq.ft above grade, a unique and versatile floor plan in Oakville's desirable neighbourhood.

3200 Ernest Appelbe Boulevard, Oakville

15 Chartwell Road, Oakville
$9,995,000
5 Beds ⋅ 6 Baths ⋅ W13707486 MLS
15 Chartwell Rd offers a lifestyle of unparalleled luxury. Drive through the gates & discover the grandeur of this palatial estate. South of Lakeshore,1 door from the lake on a HALF ACRE LOT. Painstakingly curated, the contemporary limestone masterpiece you've been waiting for. Solid iron doors lead to a grand foyer revealing the opulent book matched marble floors. Floor to ceiling wdws & French doors flood the house with light. Cascading waterfalls fank the hall.The Dining Room has statement lighting & servery making hosting a breeze. Soaring 18-ft ceilings & a grand gas f/p are focal points of the Great Room,w/captivating views of the resort style yard. Experience culinary excellence in the black lacquer& glass kitchen by NEFF that features top of the line appliances & a B/I coffee machine & butlers pantry. The intimate Living Room with f/p is the ideal retreat. A main floor office w/built-in cabinetry.2 powder & 2 laundry rooms. The backyard oasis has a gunite pool, waterfalls, fire bowls, covered terrace & outdoor kitchen & f/p.The pool house has a change room,3-pc bath & servery. Towering trees surround the home & are positioned to create privacy. A stone driveway,circular fountain & lush gardens create a breathtaking landscape.Floating marble stairs divide the 3 levels of this home or, you can take the elevator. Skylights make the upstairs airy & bright.The principal suite has nearly 13-ft ceilings, an exquisite 6-piece ensuite & 2 W/I closets. A private balcony overlooks the yard.3 add'l bdrms have 10-ft ceilings,private ensuites & W/I closets. The LL caters to all family members. A 5th bdrm/ensuite makes an ideal guest suite.Gym,R/I Golf Simulator,home theatre,Wine Cellar& doggie Spa. The Games & Rec Rooms have a 2nd kitchen & W/O.Heated garage,baths &LL flrs.Automation. Designed by Bill Hicks & features the artistic creativity of the KT Design Group. Located on Oakville's Street of Dreams, this is an iconic living space designed to impress! LUXURY CERTIFIED

15 Chartwell Road, Oakville

150 Wolfdale Avenue, 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

79 Mevira Gardens, Oakville
$1,888,000
5 Beds ⋅ 5 Baths ⋅ W13703388 MLS
Welcome to this stunning, one-of-a-kind Primont-built residence, an extensively customized masterpiece showcasing exceptional craftsmanship, sophisticated design and luxurious finishes throughout. Nestled in Oakville's highly desirable Glenorchy community, this remarkable home makes an unforgettable first impression with its striking custom front entrance. Step inside to soaring 10-ft ceilings on the main level, abundant natural light, elegant chandeliers and extensive pot lighting inside & out. The show-stopping designer kitchen is the heart of the home, featuring an oversized island, servery, stone countertops, premium built-in JennAir appliances, custom cabinetry and designer built-ins-perfect for everyday living and entertaining. The main-floor Den/Home Office offers flexibility as a potential 6th bedroom. Upstairs features 5 spacious bedrooms, including an impressive Primary Retreat with a luxurious 5-pc ensuite and dual walk-in closets. Every bedroom enjoys convenient access to a washroom and custom built-in closet organization. The unfinished basement with high ceilings offers incredible potential for an in-law suite, home theatre, gym or entertainment space. Ideally located near top-rated schools, parks, trails, shopping, dining and major highways including 403, 407 & QEW. A truly special custom-inspired home combining architectural elegance, modern convenience and practical luxury-designed to impress even the most discerning buyer!

79 Mevira Gardens, Oakville

518 Sherin Drive, 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

46 Second Street, Oakville
$7,599,000
5 Beds ⋅ 7 Baths ⋅ W13694012 MLS
Walk to downtown Oakville from this 2024 custom-built residence, just three houses from Lake Ontario on a 65' x 158' lot south of Lakeshore. A rare new-construction opportunity in Old Oakville's most walkable pocket-minutes from the harbour, the Oakville Club, Lakeshore Road dining, and waterfront trails. Offers 4,362 sq. ft. above grade plus a 2,468 sq. ft. finished lower level (6,830 sq. ft. total). Net Zero Ready with a Tarion warranty, crafted by Chatsworth Fine Homes alongside architect John Willmott and designer Jane Lockhart. Main floor features herringbone white oak floors, panel mouldings, a private office, custom mudroom, and a formal dining room. The chef's kitchen boasts Miele appliances (plumbed coffee system, dual steam/standard ovens), SubZero refrigeration, and a wine column. It opens to a great room with a linear fireplace, custom built-ins, and floor-to-ceiling garden views. The primary suite serves as a spa-inspired retreat with a freestanding tub, oversized shower, double vanity, and a dressing-island walk-in closet. Secondary bedrooms each feature private ensuites. Includes heated floors, curbless showers, and upper-level laundry with two washer/dryer sets. The lower level (10' ceilings) is built to entertain: rec room with custom bar/kitchenette, gym, theatre, full bath, additional bedroom, and walk-up access to the yard. The west-facing rear yard catches optimal afternoon sun, complete with a covered heated lounge, in-ground pool with waterfall, and a hot tub. Extras include partial lake views, a heated driveway, radiant floor heating, Crestron automation, Tesla charger rough-in, and a standby generator. A turn-key luxury home in prime Old Oakville where inventory like this rarely comes to market. LUXURY CERTIFIED.

46 Second Street, Oakville

2378 Rebecca Street, Oakville
$2,989,000
5 Beds ⋅ 7 Baths ⋅ W13692950 MLS
Custom contemporary masterpiece set on a rare, deep 150-foot lot in prime South Oakville, surrounded by prestigious multi-million-dollar estates. Spanning over 5,000 square feet of meticulously crafted total living space, this architectural home seamlessly blends European sophistication with cutting-edge modern luxury.Step inside to an breathtaking open-concept layout defined by soaring 20-foot ceilings in the grand foyer and main living room. The entire main floor features imported Italian Versace tile with integrated radiant floor heating, creating an ambiance of absolute refinement. The heart of the home is a chef-inspired gourmet kitchen equipped with dual marble islands, an extended breakfast bar, premium cabinetry, and an adjoining double-sided marble stone Dimplex fireplace with dual-mounted TV setups. A dramatic floor-to-ceiling marble waterfall feature wall serves as a stunning visual centerpiece.Ascend the architectural floating glass staircase to the second level, where you will find 4 spacious bedroom suites. Every bedroom boasts its own private heated-floor ensuite bathroom and tailored custom closet built-ins. The primary retreat offers a tranquil sanctuary featuring a private walk-out balcony and a lavish spa-like ensuite with a deep standalone soaking tub.The bright, sun-filled walk-out lower level expands your living options with 9-foot ceilings and oversized windows throughout. It includes a spacious open-concept recreation room, a 5th bedroom ideal for a nanny or guest suite, 2 additional bathrooms, and pre-plumbed rough-ins ready for a future second kitchen or custom wet bar.Located minutes from elite private schools, Oakville Harbour, downtown boutiques, fine dining, parks, and major transit routes. Uncompromising quality, world-class finishes, and an unbeatable South Oakville address!

2378 Rebecca Street, Oakville

1221 Ironbridge Road, Oakville
$2,199,999
5 Beds ⋅ 5 Baths ⋅ W13691884 MLS
Welcome to 1221 Ironbridge Road, an exceptional Fernbrook-built home completed in 2023 and offering nearly 3,600 sq. ft. of thoughtfully designed living space above grade. Designed for modern family living, this impressive 5-bedroom residence features 10-foot ceilings on the main level and 9-foot ceilings on both the second floor and basement, creating an airy and sophisticated feel throughout. Every bedroom enjoys convenient access to a bathroom, including three private ensuites and a Jack-and-Jill bath, making this home ideal for growing families and multi-generational living. The heart of the home is the chef-inspired kitchen, showcasing upgraded custom cabinetry, a built-in sub-zero refrigerator and dishwasher, double pantry storage, and a premium Wolf range. California shutters throughout add timeless elegance and privacy. Outside, extensive interlocking stonework installed in 2026 extends across the front yard, side yard, and backyard, creating a beautiful, low-maintenance outdoor space perfectly suited for busy families. Located in Oakville's sought-after Saw Whet community, just west of Glen Abbey, this prime location offers exceptional convenience for commuters with the QEW only one minute away and Bronte GO Station just five minutes from your doorstep. Families will appreciate being within the catchment area for highly regarded Abbey Park High School, one of Oakville's top-ranked secondary schools. A rare opportunity to own a nearly new luxury home in one of Oakville's most desirable communities.

1221 Ironbridge Road, Oakville

290 Duskywing Way, Oakville
$1,799,000
5 Beds ⋅ 5 Baths ⋅ W13691492 MLS
Welcome to 290 Duskywing Way, where bright, elegant family living meets a private backyard retreat in sought-after Lakeshore Woods. Beautifully positioned on a landscaped corner lot, this impressive 4-bedroom, 5-bathroom home benefits from additional windows and abundant natural light, creating a bright and airy feel throughout. Freshly painted and thoughtfully improved, it showcases extensive upgrades inside and out.The main level features soaring ceilings, upgraded hardwood flooring, California shutters, generous living and dining areas, and a spacious family room with fireplace-an inviting gathering place for family and friends. The kitchen offers abundant cabinetry, granite counters and centre island, with a convenient butler's servery connecting to the dining room. Main-floor laundry features a new washer and dryer. Upstairs, four generous bedrooms include a spacious primary retreat with walk-in closet and ensuite. A rare highlight is 3 bathrooms on the second level, including a Jack & Jill connecting two bedrooms. The professionally finished lower level offers an expansive recreation and billiards area, wet bar, gym, bathroom and private office that could serve as an additional bedroom, with excellent potential for extended-family or in-law living. Outside, enjoy a private, maturely landscaped backyard featuring a recently maintained in-ground pool with brand-new liner, gazebo, extensive hardscaping and inviting spaces for dining, lounging and entertaining. A large, recently sealed exposed aggregate concrete driveway complements the upgraded garage with new epoxy flooring and built-in cabinetry. Further improvements include newer furnace & A/C, owned hot water tank, central vacuum and irrigation system. Ideally located in a welcoming, family-friendly neighbourhood near Lake Ontario, Bronte Harbour, parks, trails, schools, shopping, dining and highways. A beautifully cared-for Lakeshore Woods home reflecting pride of ownership throughout.

290 Duskywing Way, Oakville

496 George Ryan Avenue, Oakville
$1,399,000
5 Beds ⋅ 5 Baths ⋅ W13679356 MLS
Beautifully upgraded executive corner-lot semi detached house located in one of Oakville's most desirable family-friendly communities. This stunning 4 bedroom plus 1, 3-bathroom plus 2 home offers luxury, functionality, and modern living with over $225,000 spent on premium renovations and upgrades throughout. The extended concrete driveway provides parking for up to 3 vehicles including the garage, a rare feature in the area. Inside, the bright open-concept layout features hardwood flooring throughout the entire home, upgraded lighting, elegant black hardware, modern zebra blinds, and high-end finishes completed with exceptional attention to detail. The upgraded kitchen flows seamlessly into the spacious living and dining areas, creating the perfect space for entertaining and everyday family living. Upstairs, all bathrooms have been renovated with double vanities, while the luxurious primary ensuite features a freestanding soaker tub and spa-inspired finishes. A major highlight of this home is the professionally finished legal second dwelling basement apartment with a separate side entrance. This beautifully finished 1-bedroom suite offers excellent income potential or space for extended family. Every inch of this home has been thoughtfully renovated with quality craftsmanship and pride of ownership throughout. Located close to top-rated schools, parks, trails, shopping, highways, restaurants, and all major amenities, this turnkey property offers a rare opportunity to own a fully upgraded home in one of Oakville's most sought-after neighbourhoods.

496 George Ryan Avenue, Oakville

1485 Duncan Road, 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

235 LAKEWOOD Drive, 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

3353 Liptay Avenue Unit 17, Oakville
$1,629,000
5 Beds ⋅ 4 Baths ⋅ W13672844 MLS
Welcome to this one-of-a-kind end-unit freehold bungalow with loft, double garage, and backyard backing onto protected greenspace in Oakville's desirable Bronte Creek community. Offering 2,356 sq. ft. above grade plus a fully finished basement, this home combines accessible living with privacy and community. Wide doorways and smooth, level flooring provide added convenience for those using mobility aids. Step inside to bright living and dining areas, two main-floor bedrooms, and convenient main-floor laundry. Upstairs, a spacious loft with an additional bedroom offers flexibility for guests or a private retreat. The finished basement (2013) features two additional bedrooms, kitchen, bathroom, and living space, ideal for extended family or multigenerational living. Outside, enjoy a peaceful backyard backing onto protected provincial parkland, with no future development directly behind, plus a stone patio completed in 2021. Situated on an exclusive private street, residents benefit from professionally maintained common greenspaces, prompt snow removal, additional visitor parking, and a monthly condominium road fee of $216.60. A recently established, invitation-only neighbourhood group chat connects verified property owners, encouraging mutual support, communication, and neighbourhood safety. Annual late-summer potluck gatherings offer further opportunities to connect with neighbours and enjoy a genuine sense of community. Additional highlights include excellent soundproofing, an oversized double garage, parking for four vehicles, roof and windows (2011), and a furnace, heat pump, and privately owned water heater, all replaced together in 2024, paid for, and covered by 10-year manufacturer and installer warranties. No water heater rental contract! Approximately 10 minutes from Oakville Trafalgar Memorial Hospital and close to parks, schools, shopping, and amenities, this unique home offers an exceptional combination of comfort, accessibility, privacy, and community.

3353 Liptay Avenue Unit 17, Oakville

2076 GLENFOREST Crescent, 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

56 Birch Hill Lane, 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

1516 Pinery Crescent, 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

1472 Oakhill Drive, Oakville
$7,998,000
5 Beds ⋅ 6 Baths ⋅ W13643716 MLS
Welcome to 1472 Oakhill Drive, a newly built contemporary residence in the heart of prestigious South East Oakville, where timeless sophistication meets exceptional craftsmanship. Offering nearly 7,800 sq.ft. of exquisitely finished living space across three levels, this custom designed home delivers an elevated lifestyle defined by refined architecture, luxurious finishes and effortless indoor-outdoor living. A striking façade with a metal roof, heated driveway and walkways, professional landscaping and a triple tandem garage creates an unforgettable first impression. Inside, soaring 10-foot ceilings, a dramatic two-storey foyer, solid mahogany entry door and bespoke millwork throughout set the tone for the home's impeccable attention to detail. Designed for both elegant entertaining and everyday living, the open concept main floor features a stunning chef's kitchen appointed with premium Gaggenau integrated appliances, custom cabinetry, and seamless access to the spectacular outdoor living spaces. The covered rear porch is a true extension of the home, complete with automated retractable screens, a built-in outdoor kitchen, cedar tongue-and-groove ceiling and generous lounge and dining areas. The resort inspired backyard is centred around a 14' x 34' saltwater Gunite pool with an integrated hot tub, waterfall feature and a custom cabana. The second level offers four spacious bedrooms, each with a private ensuite and custom closet solutions, creating a luxurious retreat for every family member. The finished lower level adds exceptional versatility with a fifth bedroom, a full bathroom, and expansive recreation and entertainment space. Set on one of South East Oakville's most desirable streets, this exceptional residence combines modern design, superior construction, and resort-calibre amenities in a location renowned for its top-ranked schools, lakefront parks, and proximity to downtown Oakville. A rare opportunity to own a truly distinguished custom home.

1472 Oakhill Drive, Oakville

1102 Crestview Street, Oakville
$6,250,000
5 Beds ⋅ 7 Baths ⋅ W13558096 MLS
This is not your average home-it's a statement.Set on a premium, near half-acre lot, this custom masterpiece brings together the vision of Gren Weis, the craftsmanship of Bachly Construction, and the landscape artistry of Mark Pettes-creating a residence that feels as elevated as it is effortless.From the moment you step inside, the energy shifts. Soaring 10-ft ceilings and a stunning 17-ft sun-drenched family room set the tone-open, airy, and designed to impress. A dedicated main floor office offers the perfect balance of productivity and privacy, ideal for today's work-from-home lifestyle. Whether it's an intimate night in or a full house of guests, the flow is seamless. A prep kitchen keeps everything behind the scenes running smoothly, while the newly added main-floor bar invites you to pour a drink and stay awhile. The glass-encased wine room? Pure drama-in the best way.Every bedroom is its own private retreat, complete with a luxe ensuite-because comfort should never be compromised.Downstairs, the vibe continues. Think late nights at the wet bar, morning workouts in your private gym, spa-level relaxation, and a fully equipped nanny suite. A walk-out lower level leads directly to the hot tub-blurring the line between indoor comfort and outdoor indulgence. This level isn't just extra space, it's a lifestyle.And then there's the backyard. Tiered, curated, and designed to be lived in. A newly added pool sets the scene, while the covered cabana lounge and outdoor kitchen make entertaining feel like a vacation. There's even a dedicated dog run-because every detail has been considered.Sleek, bold, and undeniably fun-this is a home that doesn't just look good, it lives beautifully.

1102 Crestview Street, Oakville

1179 Carey Road, 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

104 Whittington Place, 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

2194 Lower Base Line, Oakville
$1,779,000
5 Beds ⋅ 4 Baths ⋅ W13511208 MLS
The driveway winds in through mature trees and the house appears at the end in the centre - a stucco Spanish-style villa on 10.33 acres in Rural Oakville. By the time you reach the front door, the city is completely out of sight & sound. South-facing, Conservation Halton land on the edges. Circular drive for 10 vehicles, attached 2-car garage, A/C workshop & central vacuum. {MAIN LEVEL} Tile foyer with double mirror closet. Two main-floor bdrms - one overlooks the front yard, one the backyard - both with hardwood floors & closets. 5pc tile bath. Kitchen with skylight overhead, SS appliances (fridge, oven, built-in microwave, range hood & countertop stove), tile floors, backsplash, double sink & pot lights. Large eat-in area with W/O to balcony - you're looking straight into your own trees. Dining rm with hardwood, textured ceiling & pot lights. Family rm with hardwood, wood-burning fireplace & pot lights. {UPPER LEVEL } Primary bdrm overlooks the backyard - trees, not rooftops. Walk-in closet & separate closet. Ornate 5pc ensuite with stand-up shower & Jacuzzi tub. 5pc main bath with hardwood floors. Flexible room with built-in shelving & cabinets - office, study or storage. Third bdrm with hardwood floors & closet.{BASEMENT}Finished W/O basement. Rec room with wood-burning fireplace & built-in shelving flows directly into the wet bar area - built-in wooden bar & W/O to patio. Summer evenings are covered. Basement bdrm with closet overlooks backyard. 3pc ceramic bath. Full laundry with washer, dryer, fridge & freezer. Utility rm with water softener, HWT & HVAC. {LOCATION} Rural Oakville Greenbelt. Sixteen Mile Creek nearby, Conservation Halton land on the edges. Gateway to Bronte Creek Provincial Park trails. Golf minutes away. Hwy 407 ETR accessible - Milton & Mississauga both within easy reach. Far enough from everything to feel like an escape. Close enough that you're never actually far.

2194 Lower Base Line, Oakville

2212 Urwin Crescent, Oakville
$1,799,000
5 Beds ⋅ 5 Baths ⋅ W13505840 MLS
RECENTLY REIMAGINED FOR MODERN FAMILY LIVING WITH A RESORT-STYLE BACKYARD IN SOUGHT-AFTER WEST OAKVILLE! JUST MINUTES TO THE LAKE! This exceptional residence offers 4+1 bedrooms, 4.5 bathrooms, and a professionally finished lower level, seamlessly blending sophisticated design with everyday functionality. The open concept main level is enhanced by engineered hardwood flooring, expansive floor-to-ceiling windows, and light-filled principal rooms designed for everyday living and entertaining. The stunning custom kitchen features quartz countertops, oversized centre island with sink, JennAir gas range, pot filler, and access to the backyard. An open-riser staircase with glass panels creates a striking architectural focal point, while the living room is anchored by a dramatic feature wall with gas fireplace. Upstairs, engineered hardwood continues throughout. The primary retreat showcases a designer accent wall, elegant wall sconces, a walk-in closet with window and custom built-ins, and a spa-inspired five-piece ensuite with freestanding tub, glass shower with rainfall showerhead, and double vanity. A second bedroom features its own private three-piece ensuite, while two additional bedrooms share a beautifully appointed four-piece bathroom. A laundry room with sink completes the upper level. The backyard is a private oasis designed for entertaining and relaxation, featuring an inground pool with an eco-friendly, cost-effective copper ionizer system, extensive stone hardscaping, and a covered outdoor living area with gas fireplace. A dedicated BBQ station with natural gas line and convenient side-door access to the kitchen further enhances the outdoor experience. Ideally located close to parks, top-rated schools, Queen Elizabeth Park Community and Cultural Centre, shopping, transit, major highways, and the lake. This remarkable home offers an exceptional lifestyle in a coveted family-friendly neighbourhood. (certain exterior images have been digitally enhanced)

2212 Urwin Crescent, Oakville

1338 Chalfield Drive, Oakville
$1,888,000
5 Beds ⋅ 4 Baths ⋅ W13470090 MLS
Welcome to this exceptional Georgian-style family home, lovingly maintained by its original owner for 39 years and beautifully renovated within the past 12 months. Offering approximately 3,000 sq. ft. above ground of thoughtfully designed living space, this move-in-ready residence combines timeless charm and modern upgrades in one of East Oakville's most sought-after family-friendly neighbourhoods, Clearview.Featuring 4 spacious bedrooms, a finished basement, and outstanding curb appeal, this home has been meticulously updated with a stunning renovated kitchen, stylish new flooring throughout, and beautifully renovated bathrooms. An upgraded roof adds further peace of mind, allowing buyers to simply move in and enjoy. The elegant Georgian exterior creates a lasting first impression, while the interior showcases pride of ownership at every turn.Designed for family living, the home offers generous principal rooms, functional living spaces, and a warm, welcoming atmosphere.Perfectly located for commuters, minutes from QEW/403, for quick access and easy drive into the city. Families will especially appreciate having one of Oakville's top-rated elementary schools James Hill just steps away at the end of the street, and also St.Luke Catholic School just along the street on Kingsway.A rare opportunity (offered for the first time by original owners) to own a meticulously cared-for home with extensive recent renovations, timeless character, and an unbeatable family-friendly location. This is the one you've been waiting for.

1338 Chalfield Drive, Oakville

262 Maple Grove Drive, Oakville
$10,880,000
5 Beds ⋅ 7 Baths ⋅ W13448452 MLS
Set on one of Morrison's most coveted streets, this extraordinary custom-built estate offers over 10,800 sq ft of impeccably designed living space, complemented by a remarkable 3,400 sq ft two-level garage and showroom with accommodation for up to 10 vehicles. A striking stone façade introduces interiors defined by exceptional craftsmanship, soaring ceilings, expansive principal rooms, and walls of glass that seamlessly connect to the resort-inspired grounds. Designed for both grand-scale entertaining and refined family living, the main level features elegant formal living and dining rooms, a private executive office, and a spectacular chef's kitchen with bespoke cabinetry, premium appliances, an oversized island, walk-in pantry, and full servery. The adjoining family room and Muskoka-inspired lounge create an effortless indoor-outdoor lifestyle experience. The upper level is anchored by a luxurious primary retreat featuring a private balcony, fireplace, custom dressing rooms, and a spa-inspired ensuite. Additional bedroom suites offer exceptional comfort with custom finishes, walk-in closets, and ensuite bathrooms. The lower level is dedicated to recreation and wellness, featuring a state-of-the-art home theatre, games area, fitness studio, sauna, custom bar, wine display room, and expansive entertainment spaces. Outdoors, the estate transforms into a private resort oasis, featuring meticulously landscaped grounds, extensive entertaining terraces, and a spectacular pool setting that offers complete privacy and tranquility. Located in one of Oakville's most prestigious neighbourhoods, this exceptional residence is moments from top-ranked schools, downtown Oakville, lakefront parks, private clubs, and all the amenities that define this premier community. A truly remarkable family estate where architectural excellence, luxury, and lifestyle converge.

262 Maple Grove Drive, Oakville

Start Your Search

5 Bedroom Oakville Real Estate

Our website features the best real estate search for 5 bedroom properties available in Oakville and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

How much is your home worth?

Get instant property value now!