5-Bedroom Houses for Sale in Oakville

Trafalgar Road South; William Street West Well positioned property in historic Old Oakville, south of Lakeshore, just steps to the beach, Oakville harbour\r\nand Town Square. Sitting proudly up on a rise, this 2 1/2 storey home features wonderful views, light and\r\nplenty of space to create

Watson and Lakeshore Situated mere minutes from downtown Oakville in the esteemed southeast neighborhood, this exquisite custom-built residence, completed in 2024, showcases an elegant blend of design, functionality, and comfort. The property features a west-facing rear garden that benefits

TRAFALGAR ROAD Welcome to 302 William Street in the heart of downtown Oakville. This classic red-brick home is steeped in character and warmth. Lovingly cared for and updated over the past 54 years by the current owners, it has beautiful gardens and mature trees. This home has over 2,700 square

Chartwell Rd & Cornwall Rd Gorgeous Family Home on Prestigious Chartwell Road in Old OakvilleNestled on a prime 0.29-acre west-facing lot backing onto serene woodlands, this immaculate 4+2 bedroom residence is situated on the coveted "Street of Dreams" Chartwell Road in the heart of highly

Lakeshore Rd E and Brentwood Rd Welcome to 64 Brentwood Road, where a exquisitely crafted home masterfully blends timeless design and modern features. Located on one of the most coveted and prestigious streets and steps to the shoreline of Lake Ontario, this exceptional home is situated on

Lakeshore Rd E-Raymar Place Stately residence at the bottom of an exclusive cul de sac, one house away from the Lake and steps to Downtown Oakville. Over 8000 sqft total space, including 5293 main & second floor, plus 902sqft heated & enclosed outdoor space. Extensively renovated by Cochren

Chartwell/Esselmont/Donessle A rare opportunity to own an estate property on one of Old Oakvilles most prestigious streets. Set on an oversized 100' x 171' lot, this David Small-designed home offers over 8,000 square feet of finished living space, ideal for modern family living and entertaining.

Douglas St & Randall St Nestled steps from downtown Oakville and the lakefront, this extraordinary residence at 399 Randall St. stands as a testament to architectural brilliance and uncompromising craftsmanship. Designed by the renowned Gren Weis and masterfully executed by Whitehall Construction,

MacDonald Rd/Allan St Nestled in an immensely desired mature pocket of Old Oakville, this exclusive Fernbrook development, aptly named Lifestyles at South East Oakville, offers the ease, convenience + allure of new while honouring the tradition of a well-established neighbourhood. A selection

Cornwall Rd/Trafalgar Rd Welcome to 430 Reynolds Street, a luxurious custom-built home located in the heart of Old Oakville. This exquisite residence, constructed in 2022, showcases an open-concept design with 9-foot ceilings and oak hardwood flooring throughout the main and second floors.

Cornwall and Watson This striking contemporary home offers a seamless blend of modern design, true open-concept living, & refined functionality. Located on one of the most charming streets in Old Oakville, clean lines, expansive windows & impressive architectural details such as a metal roof,

King Street & Thomas Street A rare opportunity to own one of Old Oakville's most iconic heritage estates, masterfully restored and ideally situated just steps to the lake and downtown. This distinguished Georgian brick residence offers timeless elegance with modern sophistication featuring

Lakeshore and Caulder Rare opportunity to own a spacious bungalow on a premium 145.28 ft x 124.33 ft lot in the prestigious heart of Southeast Oakville. Nestled among towering trees and surrounded by multi-million dollar estates, this exceptional property is located in one of Oakville's most

Lakeshore E & Burgundy Dr Welcome To This Lovely, Bright Sun-Filled Bungalow, In Sought-After Prime South East Oakville, You Have A Rare Opportunity To Choose Your Ideal Living Space: **Option 1. Live In This Lovely 4000 Sq Ft Home** On A 150 X 100 Ft Professionally Landscaped Mature-Treed

South of Lakeshore/Trafalgar A Rare Gem: This Elegant Home Is Situated In The Heart Of Vibrant & Historic Downtown Oakville! Nestled On A Generous 96' X 104' Wooded Lot Along A Picturesque, Tree-Lined Street, This Exceptional Property Is Only 100 Steps To The Lake & Town Square. Meticulously

Chartwell Rd/Maple Ave Fantastic opportunity to live in desirable Old Oakville! This well-maintained raised bungalow features 3+2 bedrooms, 2 full bathrooms, a spacious eat-in kitchen and finished basement complete with a large family room, cozy gas fireplace and bright above-grade windows.

Steeles Ave & James Snow Pkwy Excellent Location, Great Opportunity to Own this Unique property, Very Rare to find *Over 53 Acres* , 4 Separate Dwellings On Property*Well Appointed Country Estate*Main House With 6+2 Bedroom , 8 Washrooms With Inground Indoor Pool & Sauna*One Two Bedroom Apartment

Dundas / 6th Line "Experience luxury detached home spanning 3,262 sq ft plus a finished basement!. The exterior boasts a striking combination of brick and stone with double wrought iron glass doors. Inside, enjoy $$$ in upgrades including crown moulding, 9' ceilings, and hardwood flooring throughout.

MacDonald Road between Allan and Reynolds Located in one of Oakville's most desirable pockets this new custom home creates a stylish atmosphere that will impress even the most detailed buyer. Architecture by Hicks Design Studio and built by Gasparro Homes this home features over 3,100 square

Chartwell/Esselmont/Donessle A rare opportunity to own an estate property on one of Old Oakville’s most prestigious streets. Set on an oversized 100' x 171' lot, this David Small-designed home offers over 8,000 square feet of finished living space, ideal for modern family living and entertaining.

Lakeshore & Brentwood Located south of Lakeshore Road and just steps to Lake Ontario, this distinguished residence blends classic architecture with contemporary refinement and was custom-built as a Princess Margaret Home Lottery Grand Prize in 2021, a testament to its exceptional design, craftsmanship,

Fourth Line & Bridge Rd Welcome to the heart of south west oakville. This renovated Corner bungalow, surrounded by custom homes, sits on an oversized lot (108.19' x 126.59'). Beautiful detached bungalow with 3 + 3 bedrooms and 2 bathroom. Large backyard and front yard. Ideal for builders and

Magnolia Cres and Hines Dr Welcome to 222 Magnolia Crescent - one of the most sought-after Mattamy homes, nestled on a quiet yet conveniently located crescent in Oakville's prestigious Preserve community. This rare Orchid model offers around 5,300 sq. ft. of luxurious living space, including

Cornwall Rd. / Chartwell Rd. Welcome to 446 Copeland Court, an exceptionally inviting family home, tucked away on a quiet court in the coveted Morrison district of South East Oakville! This unique executive is within walking distance to Downtown Oakville, the Lakefront and Canadas top schools,

Dundas & 3rd Line Beautifully maintained home on a quiet, friendly street in Oakville, just steps from scenic trails, a pond, and a short walk to Oakville Soccer Clubs four outdoor fields. Supermarkets and everyday essentials are close by, offering exceptional convenience. Located within walking

Third Line and Lakeshore Welcome to 1529 Venetia Drive, a turn-key masterpiece in Oakville's Coronation Park. This ~7000 sq ft residence on a sprawling third of an acre lot offers an unparalleled family experience. This fully automated home features bespoke living with oak floors, an abundance

Leighland / Bomorda Welcome to 1081 Bomorda Drive A Custom-Built Executive Home in College Park - Set on a rare 100' x 100' lot in one of Oakville's most established neighborhoods, this 2018 custom-built home offers approximately 6,000 sq. ft. of refined living space designed for comfort, functionality,

Cranberry Way to Bracken Drive. Nestled in the heart of Oakville's desirable Westmount neighbourhood, this meticulously maintained 4+1 bedroom, 3.5 bathroom home exudes charm and sophistication. Its inviting curb appeal is highlighted by manicured landscaping and a welcoming front entrance,

- 15 Chartwell Road 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

Lakeshore & Maple Grove Client RemarksThis beautifully updated 5-bedroom executive home offers 3,568 sq ft of total living space and features a rare 3-car garage on a quiet street in the prestigious Morrison neighborhood, just steps from Oakvilles top-ranked schools including Oakville Trafalgar

Dundas/Trafalgar Welcome to Your Dream Home in the Heart of Oakville! Discover a hidden gem nestled in the prestigious Preserve community this rarely offered Sinclair model by Mattamy Homes is a perfect fusion of elegance, comfort, and thoughtful design. Boasting three beautifully finished

Lakeshore Drive and Morrison Road Welcome to 1253 Crawford Court, an exceptional custom-built luxury estate situated in the prestigious Morrison neighborhood of South Oakville. Located on a premium, mature tree-lined pie-shaped lot within a private cul-de-sac, this property represents a rare

Lakeshore/Charnwood Spacious 5-Bedroom Home in Prime Eastlake Over 9,000 sqft Lot. Outstanding opportunity in one of Southeast Oakville's most prestigious neighborhoods! Set on a quiet crescent in the highly sought-after Eastlake community, this updated 5-bedroom, 4-bathroom 2-storey detached

Carpenters Cir This exceptional 3,646 above grade-square-foot Glen Abbey residence is perfectly positioned on a quiet, sought-after street, backing onto the lush, dense ravine of the 14-Mile Creek, meandering trails weave through the untouched serenity of nature, offering an idyllic escape

Maple Grove/Warren/Cavendish Meticulously renovated home nestled on a serene 0.42-acre lot at the end of a quiet court, this home offers a harmonious blend of timeless elegance and family-friendly comfort. Boasting 4+1 bedrooms, a 3-car garage, and nearly 4,500 sf of beautifully finished living

Upper Middle Rd W and Oxford Ave Nestled near the picturesque Sixteen Mile Creek in northeast Oakville, this stunning neoclassical house offers 3,400 square feet of elegant living space above ground. Scheduled for completion by mid-2026, the home features four spacious bedrooms, each with its

Third Line & Bridge Positioned on an exceptional 66-foot wide lot, this property offers a level of frontage that supports a full-sized custom home with over 3,150 square feet above grade, something increasingly difficult to find in this part of Oakville. What truly sets this home apart, beyond

Lakeshore/ South on Alexander A masterclass in scale and proportion, this custom-built residence is quietly positioned on 1/2 acre in one of South East Oakville’s most prestigious and tranquil enclaves. Spanning over 10,000 sq ft the lake facing residence offers exceptional privacy and

Great Lakes Blvd & Creek Path Avenue Welcome to 273 Duskywing Way, a truly exceptional executive residence nestled in the heart of Oakville's coveted Lakeshore Woods community. Set on a premium RAVNE LOT with a pool, this stunning home offers uninterrupted views of nature, privacy, and effortless

Bronte Road to Sovereign Street Welcome to 2293 Sovereign St, Oakville, a stunning property that blends luxury with comfort. This spacious home boasts 4,650 square feet of living space nestled on a generous lot of 10,947 square feet. With an asking price of $3,199,900, step into a realm of

Lakeshore Rd/Ennisclare Presenting, 21 Ennisclare Dr. East in the heart of Oakville, Ontario. An impressive waterfront property situated on Lake Ontario, boasting beauty from every angle. Be one of the few privileged homeowners in Oakville to have unsurpassed beauty at your doorstep. With a

Dundas and 6th Line Welcome to this luxury home by Fernbrook Homes (Medici Model), located in Oakville's prestigious uptown core. Boasting nearly 5,000 sq. ft.(3,507 above-grade + Finished basement) of impeccably designed living space. This home is a sure add to your viewing list. 5 Bedroom,5.5

Eighth Line & Upper Middle Rd. E Exceptionally Rare Ravine-Side Gem In One Of Oakville's Most Coveted Neighbourhoods! Welcome To The Fully Renovated 1379 Golden Meadow Trail - Nestled At The End Of A Quiet Street In Oakville's Most Desirable Communities. Set On A Rare, Pie-Shaped Ravine Lot

Morden Rd and Weighton Dr Breathtaking Custom-Built Residence Nestled In Oakville's Highly Coveted Bronte Neighbourhood. Offering over 3,300 sq. ft. of luxurious above-grade living space, plus a fully finished walkout basement, this architectural masterpiece seamlessly blends modern elegance

Morrison/Linbrook Situated on a nearly 1/2 acre lot, this custom home, designed by John Wilmott & built by Platt Fine Homes, features expansive windows & high ceilings that fill the space with light. While modern in design, warm & inviting elements like white oak & natural stone create a perfect

Robert Brown/North Park Enjoy this Beautiful Luxury Rosehaven Home from the original owners who have meticulously maintained the house Nestled In Sought after Rural Oakville area. The main floor welcomes you with open concept layout and *Stunning, Modern & grand 18 feet Ceiling Family Room

Postmaster/Pineglen Discover this stunning 4+1 bedroom home on a large corner lot in a quiet street with 2457 Sq. Ft as per the Builder floor plan and basement living area approx. 1100 Sq ft. With 9-ft ceilings and an open-concept design, carpet free, this home is filled with natural light,

Cornwall Rd/ Maple Grove Dr Welcome to 338 Maple Grove Drive – Morrison Neighborhood of South East Oakville Set on a premium 100 x 159 ft lot, this classic Tudor-style home is nestled in the highly regarded Morrison neighborhood of South East Oakville. Move in and customize the exiting

Ford Dr & Aspen Forest Dr Welcome to 2350 Deer Run Avenue, a Perfect Home for Entertainers with a Huge Swimming pool and a Bright sunroom in prestigious South East Oakville. This Well-Maintained Treed House Boasts 4 +2 Bedrooms 6 Bathrooms (2*2 PC,4 full size).Both Living and Family Room with

Chartwell / Melvin Spectacular custom home in Morrison SE Oakville. Sits on a mature south-facing lot. Boasts a well-thought-out floor plan focused on craftsmanship and quality finishes. Architecturally unique in its design and layout. Over 7200 Sq.Ft. of luxury living space. With 4+2 bedrooms,