Oakville Real Estate | Oakville Single Family Homes for Sale

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

32 PARK Avenue, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd..

$33,000,000

7 Beds ⋅ 12 Baths ⋅ 40839819 MLS® #

2054 Lakeshore Rd. East is one of Oakville's finest lakefront estates.Situated on 1.6 acres & 164.22 ft of pristine shoreline, complete with deck & stairway access to the water. Designed by renowned architect Gren Weis & brought to life by the exceptional craftsmanship of Coulson Fine Homes.This magnificent 7-bdrm, 13-bath home spans an impressive 19,210 sq ft.Step into the grand formal entrance where limestone cast walls create a dramatic first impression serving as a prelude to the extraordinary spaces beyond.The residence showcases 12 ft ceilings on the main level, Brazilian walnut flooring thru-out & custom cabinetry adorns this remarkable home.The estate features an expansive living & dining rm w/breathtaking water views, perfect for intimate gatherings or grand celebrations.Step outside to the covered terrace where you can relax to the sounds of the Bellagio inspired fountains & waterfall.The gourmet open-concept kit.flows effortlessly into the fam.rm where water views & fp create a relaxed & comfortable space.The lower-level transforms into an entertainer's paradise, w/a state-of-the-art home theatre, gym w/direct access to the infinity edge pool, steam room, golf simulator, wine cellar, billiards area w/rec room & catering kit.A private 2-bdrm nanny suite w/sep. entrance provides additional flexibility.An elevator gives you convenient access to all 5 levels of this thoughtfully designed home.The outdoors offers multiple entertaining areas nestled within the manicured landscaped grounds, the lakefront deck & poolside.The power screened sunroom offers 3 season enjoyment. His&Her double car garages to accommodate 4 vehicles w/additional parking for 15 more on the circular driveway & auxiliary prkng areas-perfect for hosting memorable events.This waterfront estate represents more than just a home it's a lifestyle statement where every detail has been carefully curated to create an environment of uncompromising luxury & comfort. LUXURY CERTIFIED. (id:5764)

2054 LAKESHORE Road East, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$7,470,000

5 Beds ⋅ 7 Baths ⋅ 40839389 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. (id:5764)

129 WOLFDALE Avenue, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc..

$1,610,000

5 Beds ⋅ 4 Baths ⋅ 40838179 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. (id:5764)

2425 NICHOLS Drive, Oakville

Listing courtesy of Right at Home Realty.

$1,999,900

5 Beds ⋅ 4 Baths ⋅ 40836934 MLS® #

Welcome to 2205 Shaftesbury Court, nestled in Oakville’s beloved Joshua Creek community. This stunning 4+1 bedroom home features a thoughtfully designed main floor with a formal living and dining room, eat-in kitchen, and family room, perfect for everyday family living and entertaining. The walkout basement complete with in-law suite offers incredible flexibility for multigenerational families, a teenager retreat, or rental 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 that adapts to every stage of family life, this one is truly special. (id:5764)

2205 SHAFTESBURY Court, Oakville

Listing courtesy of Real Broker Ontario Ltd..

$2,679,000

5 Beds ⋅ 6 Baths ⋅ 40828660 MLS® #

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

390 SEATON Drive, Oakville

Listing courtesy of RE/MAX Aboutowne Realty Corp..

$2,449,000

4 Beds ⋅ 4 Baths ⋅ 40817114 MLS® #

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

2238 LYNDHURST Drive, Oakville

Listing courtesy of ROYAL LEPAGE SIGNATURE REALTY.

$3,790,000

4 Beds ⋅ 4 Baths ⋅ 40802920 MLS® #

Nestled in an immensely desired mature pocket of Old Oakville, this exclusive development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. A selection of distinct detached single family models, each magnificently crafted with varying elevations, with spacious layouts, heightened ceilings and thoughtful distinctions between entertaining and principal gathering spaces. A true exhibit of flawless design and impeccable taste. Impressive detached w/47-foot frontage, 2836 sqft of finished space w/an additional 1,000+ sqft(approx) in the lower level left untouched. Curated:4 beds + 3.5 baths. Utility wing from garage, chef's kitchen w/w/in pantry, expansive breakfast+great room. Quality finishes are evident; with 11' ceilings on the main, 9' on the upper & lower levels and large glazing throughout, including 12-foot glass sliders to the rear terrace from great room. Quality millwork w/solid poplar interior doors/trim, plaster crown moulding, oak flooring & porcelain tiling. Customize stone for kitchen & baths, gas fireplace, central vacuum, recessed LED pot lights & smart home wiring. Downsview kitchen w/walk-in pantry, top appliances, dedicated breakfast + expansive glazing. Primary retreat impresses w/2 walk-ins + hotel-worthy bath. Bedroom 2 & 3 share ensuite & 4th bedroom enjoys a lavish ensuite. Convenient upper level laundry. No detail or comfort will be overlooked, w/high efficiency HVAC, low flow Toto lavatories, high R-value insulation, including fully drywalled, primed & gas proofed garage interiors. Refined interior with clever layout and expansive rear yard offering a sophisticated escape for relaxation or entertainment. (id:5764)

338 MACDONALD Road, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd..

$4,290,000

4 Beds ⋅ 4 Baths ⋅ 40803093 MLS® #

Nestled in an immensely desired mature pocket of Old Oakville, this exclusive development, aptly named Lifestyles at South East Oakville, offers the ease, convenience and allure of new while honouring the tradition of a well-established neighbourhood. The Douglas Collection is an extension of the inaugural development with an exclusive collection of seven homes located on Douglas Avenue. Distinct detached single family models, each magnificently crafted with varying elevations, with spacious layouts, heightened ceilings and thoughtful distinctions between entertaining and principal gathering spaces. A true exhibit of flawless design and impeccable taste. The Chatsworth; detached home with 48-foot frontage, between 3,188-3,204sf finished space w/an additional 1,000+sf (approx)in the lower level & 4beds & 3.5 baths. Utility wing from garage, chef’s kitchen w/w/in pantry+ generous breakfast, expansive great room overlooking LL walk-up. Quality finishes are evident; with 11' ceilings on the main, 9' on the upper & lower levels and large glazing throughout, including 12-foot glass sliders to the rear terrace from great room. Quality millwork w/solid poplar interior doors/trim, plaster crown moulding, oak flooring & porcelain tiling. Customize stone for kitchen & baths, gas fireplace, central vacuum, recessed LED pot lights & smart home wiring. Downsview kitchen w/walk-in pantry, top appliances, dedicated breakfast + expansive glazing. Primary retreat impresses w/2 walk-ins + hotel-worthy bath. Bedroom 2 & 3 share ensuite & 4th bedroom enjoys a lavish ensuite. Convenient upper level laundry. No detail or comfort will be overlooked, w/high efficiency HVAC, low flow Toto lavatories, high R-value insulation, including fully drywalled, primed & gas proofed garage interiors. Refined interior with clever layout and expansive rear yard offering a sophisticated escape for relaxation or entertainment. (id:5764)

101 DOUGLAS Avenue, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd..

$4,295,000

6 Beds ⋅ 8 Baths ⋅ 40793876 MLS® #

This is a remarkable vacant lot that includes drawings and building permit. House pictures are renderings and details are from the drawings. Embark on a life of uncompromised luxury with this architectural masterpiece by renowned architect David Small. Perfectly located South of Lakeshore steps from Appleby College, lake and downtown Oakville. Evoking a sophisticated Laneway Country atmosphere on a rare 90’ x 340’ lot with walk-out basement. The estate features a long circular private drive that frames a sun-drenched, West-facing backyard. The home is designed as the ultimate multi-generational sanctuary, that offers a rare Double Primary layout: a magnificent main-floor master suite for accessible luxury, plus a second-level master retreat with separate His & Her ensuites. The elevator services all three levels, ensuring effortless movement throughout soaring interiors defined by dramatic cathedral ceilings. With building permits in hand and a bespoke interior package by WOLFE Interior Design, this Net Zero Ready estate blends timeless character with elite modern performance. Car enthusiasts will prize the 5-car capacity, utilizing the attached garage and the detached tandem garage within the cabana. Beyond the essentials, the floor plan is packed with exceptional features, including a main floor office, lower level dedicated music/theater room, glass-walled fitness center, custom sauna and steam room, wine cellar, and private nanny and guest suites. Surrounded by 10M-12M estates. Architectural drawings, interior design, floorplans and building permits available on request. 10+++ (id:5764)

408 LAKESHORE Road West, Oakville

Listing courtesy of RE/MAX Aboutowne Realty Corp..

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