Oakville ON 5 Bedroom Real Estate, Homes, Condos for Sale

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

$7,470,000

5 Beds ⋅ 7 Baths ⋅ W13429066 MLS

Welcome to 129 Wolfdale Ave, a custom-designed modern craftsman estate, positioned on a premium lot in Southwest Oakville. With approximately 7,300 sq.ft. of living space, and an incredible 1,700 sq.ft. two level garage that stores 6 cars indoors, serviced by a car elevator. This exceptional home blends refined architecture resort-inspired outdoor living, surrounded by a private, tree-lined backdrop. The portico leads into a breathtaking foyer, setting the stage for the elegant interiors beyond. Considered finishes include coffered ceilings, herringbone marble flooring, and wide-plank oak throughout the principal spaces. A stylish main floor office, complete with bespoke millwork. The great room features 14' ceilings, a custom walnut media wall, and a floor-to-ceiling stone fireplace. This space flows effortlessly into the chef's kitchen, beautifully appointed with a full Thermador fridge and freezer, Gaggenau double ovens, range, steam oven, warming drawer, and quartz countertops. A fully equipped butler's pantry that keeps entertaining effortless. The upper-level hosts four spacious bedrooms, each with private ensuites with heated floors. The primary suite is a true retreat, featuring a private balcony, a spa-inspired five-piece ensuite, and a custom walk-through closet. The finished lower level offers additional living space, including a fifth bedroom, walk-up access to the rear garden, gym and home theatre. All six garage spaces, along with driveway and front walkway are radiant heated, ensuring year-round comfort and no snow buildup. Luxury Certified.

129 WOLFDALE Avenue, Oakville

$1,610,000

5 Beds ⋅ 4 Baths ⋅ W13431348 MLS

Freshly renovated executive home in prestigious Wedgewood Creek! This spacious 5-bedroom, 4-bathroom residence offers approximately 2825 sq. ft. of beautifully designed living space featuring new flooring throughout the main and upper levels, formal living and dining rooms, a dedicated home office, and a welcoming family room with a gas fireplace. The updated kitchen boasts quartz countertops, stainless steel appliances, a centre island, and a walkout to a private backyard. Upstairs, enjoy a luxurious primary retreat with a 5-piece ensuite, plus a versatile fifth bedroom with its own ensuite-ideal for guests or multigenerational living. A full, unfinished basement offers incredible future potential. Furnace (2020), NEW AC ( 2026), and water heater (2023) are new, no rentals. Washer/dryer 2025. Double garage and 4-car driveway. Located near top-rated schools, parks, trails, shopping, community centres, and major highways. An exceptional opportunity in one of Oakville's most desirable family communities.

2425 Nichols Drive, Oakville

$10,900,000

5 Beds ⋅ 5 Baths ⋅ W13430514 MLS

Nestled in the heart of downtown Oakville, this magnificent historical home offers unparalleled charm and elegance, combined with modern amenities. Spanning over 8,000 square feet, the expansive layout provides both grandeur and comfort, perfect for family living or entertaining on a grand scale. With stunning views of the sparkling waters of Lake Ontario, every room is designed to maximize the beauty of its lakeside setting. The home boasts high ceilings, intricate architectural details and walnut hardwood floors, blending timeless craftsmanship with contemporary design. The private lush yard with 104 feet of frontage is a rare gem, providing a serene outdoor oasis with mature trees and ample space for outdoor activities or quiet relaxation and complete privacy. Whether you're enjoying a morning coffee while gazing at the lake or hosting a summer gathering, the outdoor space is as inviting as the interiors. The property's prime location puts you just steps from Oakville's charming downtown, offering convenient access to world-class dining, shopping, and cultural attractions, while still providing the tranquility of lakeside living. With its rich history, extraordinary space, and unbeatable location, this is a once-in-a-lifetime opportunity to own a piece of Oakville's heritage.

350 King Street, Oakville

$5,399,000

5 Beds ⋅ 7 Baths ⋅ W13419574 MLS

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

581 Maplehurst Avenue, Oakville

$1,999,900

5 Beds ⋅ 4 Baths ⋅ W13417624 MLS

Welcome to 2205 Shaftesbury Court, nestled in Oakville's beloved Joshua Creek community. This stunning 4+1 bedroom home features athoughtfully designed main floor with a formal living and dining room, eat-in kitchen, and family room, perfect for everyday family living andentertaining. The walkout basement complete with in-law suite offers incredible flexibility for multigenerational families, a teenager retreat, orrental income potential. Sitting at the end of a quiet court, enjoy an extended driveway with ample parking for family and guests. Steps to top-rated Halton district schools, a park, and all the charm that makes Joshua Creek one of Oakville's most sought-after communities. A home thatadapts to every stage of family life, this one is truly special.

2205 Shaftesbury Court, Oakville

$1,188,000

5 Beds ⋅ 2 Baths ⋅ W13221180 MLS

A truly rare offering in one of Oakville's most sought-after neighbourhoods, this 3+2 bedroom, 2-bathroom, 1+2 kitchens (rare) bungalow is set on an exceptional pie-shaped lot - a highly rare find that presents outstanding potential for families, builders or investors. The main floor features a generous, light-filled living room anchored by a classic wood-burning fireplace, with large bedrooms and a functional layout throughout. Primary bedroom features a large walk in closet. For families, there is a walk-out basement with private separate entrance, 2 bedrooms, and full kitchen providing immediate rental income potential or an in-law suite. The massive tree-lined backyard is among the largest and most private available in this market, offering limitless possibilities for luxury outdoor living, future development, or both. An extended private driveway provides ample parking with a charming front yard. Perfectly positioned minutes from Appleby College, The Oakville waterfront, walking trails, shopping, QEW/401, and the GO Train corridor. A compelling combination of lot size, location, and income potential in one charming home!

517 Pinegrove Road, Oakville

$1,999,900

5 Beds ⋅ 5 Baths ⋅ W13212812 MLS

Welcome To This Modern, Extensively Upgraded Luxury Residence Nestled Within An Exclusive Enclave In The Prestigious River Oaks Community - Just Steps To 16 Mile Creek & Lion's Valley Park.Offering Approximately 4,000 Sq. Ft. Of Thoughtfully Designed Living Space, This Exceptional 4+1 Bedroom Family Home Delivers A Perfect Blend Of Sophistication, Comfort & Lifestyle.Soaring 9-Foot Ceilings, Rich Hardwood Flooring & Pot Lights Flow Seamlessly Throughout The Open-Concept Layout. The Two-Storey High Family Room Creates A Striking Architectural Statement At The Heart Of The Home.The Chef's Dream Kitchen Showcases A Centre Island, Custom Cabinetry & A Full Suite Of Premium Appliances, Including A Sub-Zero Two-Door Refrigerator, Wolf Cooktop, Dual Ovens (Steam & Conventional), Built-In Warmer & ASKO Dishwasher - Truly Curated For The Discerning Entertainer.The Expansive Primary Suite Retreat Features Custom Built-In Closets With Professionally Designed Organizers & A Spa-Inspired 5-Piece Ensuite Complete With Heated Floors. The Generously Appointed Second Primary Bedroom Enjoys Its Own Private 3-Piece Ensuite - Perfect For Extended Family Or Guest Stays. Two Additional Upper Bedrooms Complete This Level.The Finished Basement Adds Versatile Living Space With A Fifth Bedroom, Jenn-Air Wine Fridge & Jenn-Air Built-In Microwave - Ideal For Entertaining Or In-Law Use. Perfectly Positioned For Commuters & Families Alike, This Prime Location Offers Effortless Access To Hwy 403, The QEW & Hwy 407. Top-Ranked Public & Private Schools Including St. Ignatius Of Loyola, Forest Trail Public School & White Oaks Secondary Are Just Minutes Away.Shopping, Grocery Stores, Fine Dining, Medical Centres & The Vibrant Oakville GO Station Are All Nearby - Offering The Ultimate Balance Of Peaceful Neighbourhood Living & Urban Convenience.

2480 Upper Valley Crescent, 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

$2,679,000

5 Beds ⋅ 6 Baths ⋅ W13126692 MLS

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

390 Seaton Drive, Oakville

$3,800,000

5 Beds ⋅ 6 Baths ⋅ W13125176 MLS

Be the first to live in this custom built upgraded 5-bedroom, 6-washroom home in the sought-after Glen Abbey Encore community. Situated on a ravine-backed corner lot overlooking the Fourteen Mile Creek, this home offers over 4,440 sq ft above grade plus over 2,160 sq ft of unfinished basement space with walk-up access to a fully fenced backyard. Enjoy access to one of the area's largest parks featuring tennis & pickleball courts, basketball, soccer field, splash pad, playground, and trails. Featuring 11 ft ceilings on the main floor and 9 ft ceilings on the second floor and basement, upgraded 90" solid-core interior doors, hardwood flooring, coffered ceilings with crown moulding, pot lights, oversized windows, skylight above the staircase, open-riser staircase with stainless steel square spindles, elevated deck, dual furnaces & A/C systems, central vacuum including garage connection, smart lighting, exterior cameras, motorized blinds, and smart garage door openers with integrated cameras. All five bedrooms feature direct bathroom access, including three ensuites and a Jack & Jill bath. The primary suite offers ravine views, dual walk-in closets, and a spa-inspired ensuite with heated floors. The home also features two exterior entrances with covered porches, plus a main-floor office/den connected to a full bathroom. The custom Downsview Kitchen (one of Canada's premier luxury kitchen brands) features premium appliances including Sub-Zero column fridge/freezer and undercounter refrigerator, Wolf built-in oven, microwave & gas range, Miele built-in coffee system, and two Bosch dishwashers. Finished with quartz slab backsplash, double waterfall quartz island, large-format porcelain slab flooring, designer apron-front workstation sink, custom pull-out organizers, deep soft-close cabinetry, under-sink retractable central vacuum hose system, and a fully equipped servery with additional sink and second dishwasher connected to the breakfast area overlooking the ravine.

1283 Meadowside Path, Oakville

$1,165,888

5 Beds ⋅ 4 Baths ⋅ W13079916 MLS

Welcome to 313 Bronte Road, a beautifully updated home nestled in the heart of Bronte, one of Oakville's most desirable communities. Situated on a quiet, family-friendly street south of Rebecca Street, this property offers exceptional versatility and investment potential.This property includes three separate living spaces:Main Floor: Three-bedroom, unit Second Floor: One-bedroom and unit Basement: One-bedroom, An excellent opportunity for investors or end-users looking to live in one unit while generating rental income from the other two units.Enjoy the best of Bronte living just minutes from the lake, scenic waterfront trails, Bronte Harbour, parks, GO Transit, top-rated schools, shopping, and a wide variety of amenities. This is a rare opportunity to own in a quiet, established neighbourhood while remaining close to everything you need.Total Monthly Rental Income: $6,400.00 from three units, Main Floor, Second Floor and Basement. Buyers and buyer agents are responsible for conducting their own due diligence regarding the property, including verifying all measurements, retrofit status.

313 Bronte Road, Oakville

$2,698,000

5 Beds ⋅ 5 Baths ⋅ W13066506 MLS

This Architecturally Designed Home Comes Complete With 5 Bedrooms 3 Full Baths And 2 Half Baths A Custom Kitchen With Built In Appliances, Located In A Highly Sought After Tree Lined Quiet Street In South West Oakville This Quality Custom Built Home Offers Exceptional Decor High End Features And Over 5000 Sq Feet Of Finished Living Space. Great Room Open To Above, Fully Finished Basement, In-Ground 24X32 Salt Water Pool With Extensive Landscaping & Mature Gardens.

531 Jeanette Drive, Oakville

$6,459,000

5 Beds ⋅ 8 Baths ⋅ W13050914 MLS

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

172 Burgundy Drive, Oakville

$23,980,000

5 Beds ⋅ 8 Baths ⋅ W13030806 MLS

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

489 Lakeshore Road E, Oakville

$1,999,999

5 Beds ⋅ 4 Baths ⋅ W12876160 MLS

Welcome To This Unique, Custom-Built Home In Desirable East Oakville. Situated On A Premium, Treed Lot, This Home Features An Amazing Heated Sunroom With Massive Windows, Tile Floors, And A Stunning Entertainment Wall Including A Fireplace, Desk, And A Space For Your Wall-Mounted TV. Double Entry French Doors Lead To A Backyard Retreat Patio Area Equipped With An Outdoor Kitchen, Gazebo, Waterfall Feature, Garden Shed, And Ample Room For A Pool Or Hot Tub. Inside Features An Open Concept Main Floor Design With A Grand Kitchen, Built-In Appliances, Granite Countertops, Backsplash, Center Island, Pot Lights, And Large Windows. The Main Floor Bedroom Has Access To A Full 3-Piece Bathroom And Can Be Easily Converted To A Separate Formal Dining Room Or Office. The Space Also Includes Extensive Wall Trims And Hardwood Floors Throughout. The 2nd Floor Has 4 Additional Bedrooms And A Laundry Room. The Finished Basement Has A Possible Side Entrance And An Open Concept Layout With A Kitchen And 3-Piece Bath, Perfect For Large Family Gatherings, An In-Law Suite, Or Additional Income!

427 Pinegrove Road, Oakville

Browse All Oakville ON 5 Bedroom Properties for Sale

5 Bedroom Oakville Real Estate

How much is your home worth?

How much is your home worth?