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

Beautifully built and impeccably finished, this custom residence offers more than 6,700 square feet of living space in one of Oakville's most sought-after neighbourhoods. Stone construction, a solid wood entry door, heated garage floors, and timeless architectural detailing set the tone for the quality found throughout the home. Inside, the foyer features heated marble tile, plaster crown mouldings, poplar baseboards, and sightlines that lead into bright, open spaces. A dramatic dining room anchors the main level with a soaring skylight, custom wall panelling, integrated speakers, and carefully curated lighting. The chef's kitchen is designed with extensive custom cabinetry, quartz countertops, a large island, and easy flow to the family room. The servery and mudroom connect seamlessly; each finished with thoughtful storage and heated floors. Upstairs, all four bedrooms are generously scaled and feature private ensuite baths. The primary suite includes a fireplace, custom walk-in closet, and a beautifully coordinated ensuite with heated floors, a freestanding tub, glass shower, and frosted-glass water closet. A full-size laundry room with cabinetry and folding space completes this level. The lower level offers exceptional versatility with radiant in-floor heating, two additional bedrooms, a three-piece bath with sauna, a recreation room with fireplace, a wet bar/kitchen setup, and a dedicated theatre room beneath the back porch. Wide walk-up access brings in natural light and creates an ideal in-law or extended-family space. Outdoors, the large stone terrace features a gas fireplace and outdoor kitchen with built-in BBQ, extending the home's entertaining potential. Motorized blinds, CAT-6 wiring, solid core doors, and an oak staircase with glass panels highlight the home's elevated craftsmanship. With top-ranked schools, shopping, GO access, and major highways nearby, this is a quality home in a prime location.

481 Chartwell Road, Oakville

$3,498,000

6 Beds ⋅ 5 Baths ⋅ W12831352 MLS

Unobstructed Lake Ontario views define this rare opportunity in South East Oakville's prestigious Arkendo enclave. A truly breathtaking backdrop with a year round promise of spectacular sunrises over the lake and tranquil evenings. The original but meticulously maintained 5 bedroom residence offers 3,122 sq.ft. above grade plus a 1,330sq. ft. finished lower level, presenting an ideal canvas for renewal or renovation.The generous principal rooms all have lakeviews and the functional layout and abundant natural light throughout provide a solid foundation for a new owners vision. Set among luxury homes and close to top schools, downtown Oakville, and major highways and GO transit, this property is perfect for buyers seeking to create their signature lakeview estate in one of Oakville's most exclusive waterfront pockets on a 12,000sqft lot with RL3-0 zoning and 152ft south facing rear gardens and lake views. Some photos are virtually rendered.

20 Arkendo Drive, Oakville

$2,699,000

6 Beds ⋅ 5 Baths ⋅ W12818918 MLS

Luxury Living That Surpasses Expectations!This exceptional custom-built residence offers overall 4700 sq. ft. of beautifully finished living space, plus an abundance of storage area and privacy. If you're considering any other property, this is a must-see to compare for value, features, upgrades. Designed with both elegance and practical luxury, including a laundry room on each floor.This home stands out as a rare opportunity offering outstanding value in today's luxury market. Designed with high ceilings, extra wide staircase, wood trims/crown moldings throughout and no wasted open to above space. The open-concept main floor showcases living room, dining room, office, family room and a breakfast area with access to deck. The gourmet kitchen featuring an oversized island, premium appliances and a spacious butler's pantry, perfect for hosting or everyday family living. The home offers 6 spacious bedrooms and 5 beautifully appointed bathrooms. The sizeable primary bedroom offers linear fireplace, walk in closet, and a 6 pc luxurious ensuite featuring a large glass "spa steam shower". A fully finished basement complete with French door walk-up access to the private backyard, creating ideal potential for extended family living or seamless indoor-outdoor entertaining. All basement windows extra large and not set in deep window wells. Set on a private, pool-sized lot, the outdoor space is designed for enjoyment, tiered deck, sprinkler system and a custom brick oven/BBQ, perfect for gatherings and summer entertaining. Additional features include a garage with rough-in for EV charging, adding future-ready convenience. Great curb appeal, porch and large windows. This home offers both privacy and convenience, with excellent schools and amenities close by, making it ideal for families seeking upscale living in a prime, peaceful setting. This remarkable home is loaded with premium features, and the list of upgrades truly goes on. A must see. Shows to perfections.

1211 Pinegrove Road, Oakville

$3,795,000

5 Beds ⋅ 4 Baths ⋅ W12812288 MLS

Spectacular lakefront property with 93' frontage on Lake Ontario. Located on a quiet, mature cul-de-sac, this custom built, family home offers 4+1 Bedrooms, 3.5 Baths with over 2800SF above-grade + 1400 SF Finished Lower Level. Architecturally designed with wall-to-wall windows overlooking the lake, solid brick construction with clay tile roofing, this home was built to last. 9' and 10' ceilings on the main floor. Oak hardwood floors throughout both levels. Grand entrance foyer with oak staircase. Beautiful Living Room with fabulous marble fireplace surround with gas insert open to Dining Room with wall to wall patio doors to the terrace with incredible lake views. Fabulous Kitchen/Breakfast Room is a blank canvas with the perfect space to install the waterfront Kitchen of your dreams. Walk-outs to both decks and open to the the Family Room with stunning marble fireplace with gas insert. The main floor features a mudroom with side entry and inside entry from full-sized two-car garage. The Primary suite features oversized windows and a walk-out to second floor balcony with outstanding lake views, luxury ensuite bathroom and walk-in closet. Two more Bedrooms overlook the lake with oversized windows. The front Bedroom opens to a bonus room above the garage which could be handy as a Den or quiet retreat. The Lower Level has excellent ceilings height, good windows and features one Bedroom, a 3-Piece Bathroom, Recreation Room, Den, Laundry Room, storage and more. Beautifully landscaped and maintained property fully fenced with wrought iron gate access to the lake. Cobblestone driveway accommodates 4 cars. Outstanding value on Lake Ontario. A must see!

3286 Shelburne Place, Oakville

$4,779,000

W12807870 MLS

Incredible turn-key 5,463 SF corner unit available for sale at the highly desirable Maple Grove Corporate Centre in the heart of Oakville's thriving business corridor. Flexible layout suitable for retail or office use allowing for various uses including medical. Offering a mix of reception, open space, kitchen, boardroom, washrooms and several offices and workspaces on glass including a large outdoor patio. Located in a well-maintained complex with ample on-site parking and quick access to the QEW and Highway 403. Ideal opportunity for businesses seeking a strategic and accessible Oakville location.

1525 Cornwall Road Unit 26-27, Oakville

$4,779,000

W12807826 MLS

Incredible turn-key 5,463 SF corner unit available for sale at the highly desirable Maple Grove Corporate Centre in the heart of Oakville's thriving business corridor. Flexible layout suitable for retail or office use allowing for various uses including medical. Offering a mix of reception, open space, kitchen, boardroom, washrooms and several offices and workspaces on glass including a large outdoor patio. Located in a well-maintained complex with ample on-site parking and quick access to the QEW and Highway 403. Ideal opportunity for businesses seeking a strategic and accessible Oakville location.

1525 Cornwall Road Unit 26-27, Oakville

$3,020,000

W12807814 MLS

Incredible turn-key 3,453 SF corner unit available for sale at the highly desirable Maple Grove Corporate Centre in the heart of Oakville's thriving business corridor. Flexible layout suitable for retail or office use permitting various uses including medical. Offering a mix of reception, open space, kitchen, boardroom, washrooms and several offices and workspaces on glass including a large outdoor patio. Located in a well-maintained complex with ample on-site parking and quick access to the QEW and Highway 403. Excellent opportunity for owner-occupiers or investors. Move in ready! This unit can also be sold with the neighbouring listed unit 26 for a combined total area of 5,463 SF.

1525 Cornwall Road Unit 27, Oakville

$3,020,000

W12807800 MLS

Incredible turn-key 3,453 SF corner unit available for sale at the highly desirable Maple Grove Corporate Centre in the heart of Oakville's thriving business corridor. Flexible layout suitable for retail or office use permitting various uses including medical. Offering a mix of reception, open space, kitchen, boardroom, washrooms and several offices and workspaces on glass including a large outdoor patio. Located in a well-maintained complex with ample on-site parking and quick access to the QEW and Highway 403. Excellent opportunity for owner-occupiers or investors. Move in ready! This unit can also be sold with the neighbouring listed unit 26 for a combined total area of 5,463 SF.

1525 Cornwall Road Unit 27, Oakville

$2,549,000

W12805558 MLS

Prime 2,916 SF commercial unit for sale at the Maple Grove Corporate Centre in the heart of Oakville's established business district. Functional layout suitable for office or retail permitting various uses including medical with a large open area, kitchen, washrooms, and offices on glass. Located in a well-maintained complex with ample on-site parking and professional curb appeal. Excellent access to the QEW and Highway 403, providing seamless connectivity throughout the GTA. Ideal opportunity for owner-users or investors in a high-demand commercial corridor. Move in ready!

1525 Cornwall Road Unit 5, Oakville

$2,549,000

W12805512 MLS

Prime 2,916 SF commercial unit for sale at the Maple Grove Corporate Centre in the heart of Oakville's established business district. Functional layout suitable for office or retail permitting various uses including medical with a large open area, kitchen, washrooms, and offices on glass. Located in a well-maintained complex with ample on-site parking and professional curb appeal. Excellent access to the QEW and Highway 403, providing seamless connectivity throughout the GTA. Ideal opportunity for owner-users or investors in a high-demand commercial corridor. Move in ready!

1525 Cornwall Road Unit 5, Oakville

$3,450,000

W12782366 MLS

Attention Investors & Developers! Zoning approved for four luxury townhome units (RM1) with a total buildable gross floor area of 14,736 sq. ft. on a 0.24-acre lot (building permits not included). Features both surface and underground parking. Renderings available for review. Located in a prestigious and tranquil enclave in West Oakville, just south of Lakeshore. Steps from Bronte Heritage Waterfront Park, Bronte Boathouse, and Marina! An upgraded, move-in-ready home is currently on-site, perfect for living or renting.

47 Nelson Street, Oakville

$3,499,999

3 Beds ⋅ 3 Baths ⋅ W12779900 MLS

Set on a spectacular 0.566-acre lot, this property is enveloped by towering trees and lush gardens, and backing onto the tranquil Kings Park Woods. Offering nearly 25,000 sq. ft. of privacy and tranquility, this Muskoka-like retreat sits on one of Southeast Oakville's most prestigious streets. A generously sized interlocked driveway leads past the elegant front yard to an impressive 3-car garage. Lovingly maintained by the same family for over 40 years, the home is in pristine condition. The interior features expansive principal rooms, including formal living and dining spaces, a large kitchen with a breakfast area addition, and an open-concept family room-perfect for both day-to-day living and entertaining. A wealth of windows throughout brings in abundant natural light and frames beautiful views of the front streetscape as well as the forested backyard. With multiple fireplaces and hardwood floors throughout the main level, the home exudes warmth and charm. Convenient access to the garage is provided through the laundry room. Upstairs, the spacious primary suite is complemented by three double closets, built-in bookcases, a 3-piece ensuite, and additional flexible space. Two more generously sized bedrooms, along with a 4-piece bathroom featuring a jacuzzi tub, complete this level. The true highlight of the home is the backyard-a private oasis of mature trees, manicured gardens, and a well-positioned pool that basks in sunlight. A full irrigation system ensures the landscaping stays lush. Recent upgrades include a new roof, furnace, and electrical panel, while the garage boasts 50-amp service, ideal for a lift or electric vehicle charging. Walking distance to Oakville's top public and private schools, including OT and St. Mildred's, and just minutes to shopping, this property offers exceptional potential. Whether you choose to build a custom home or renovate and expand this charming residence, the large lot allows for endless possibilities.

1296 Cumnock Crescent, Oakville

$3,450,000

3 Beds ⋅ 3 Baths ⋅ W12778182 MLS

Attention Investors & Developers! Zoning approved for four luxury townhome units (RM1) with a total buildable gross floor area of 14,736 sq. ft. on a 0.24-acre lot (building permits not included). Features both surface and underground parking. Renderings available for review. Located in a prestigious and tranquil enclave in West Oakville, just south of Lakeshore. Steps from Bronte Heritage Waterfront Park, Bronte Boathouse, and Marina! An upgraded, move-in-ready home is currently on-site, perfect for living or renting. **EXTRAS** Includes stainless steel appliances: fridge, stove, built-in dishwasher; front-loading washer and dryer; light fixtures; window coverings; garage door opener; gazebo; garden shed; and greenhouse.

47 Nelson Street, Oakville

$4,790,000

4 Beds ⋅ 8 Baths ⋅ W12774104 MLS

Your searching for a dream home stops right here. Discover an unparalleled opportunity to own a truly magnificent custom-built home. Modern and stylish, designed with meticulous attention to details, owning all stunning features dreamed for a luxury and comfort home. Prestigious location with amazing view of Lake Ontario from the upper level. Windows and skylights aplenty ensures the open concept interior is flooded with light all throughout the day. Lounge anywhere and everywhere within its massive 8461 square feet interior, with another 1469 square feet of balcony/terrace space to bask in the lake breeze and sun. Experience the luxury of waterfront living, this elegant home is sure to impress you and all your guests, with fully featured sports bar, movie room, a wine cellar, exercise room, and a fantastic rear deck with lounge area and pool to relax in. An exquisite masterpiece offering everything you need for elegant living and entertaining.

3425 Lakeshore Road W, Oakville

$3,600,000

W12773688 MLS

Prime Downtown Oakville location, this turnkey mixed-use building features two prime commercial units and four residential suites on second floor. This property sits on one of the most coveted blocks in downtown Oakville right on Lakeshore between Navy and Thomas. This offering provides a stable income stream and significant potential for future appreciation and redevelopment. Well-maintained with recent renovations including commercial spaces, windows, roof and appliances.

150 Lakeshore Road E, Oakville

$4,889,915

W12750996 MLS

Three Oaks Business Centre presents occupiers and investors a rare opportunity to own state-of-the-art industrial condo including mezzanine. Built by Beedie, one of Canada's largest private industrial developers, Three Oaks Business Centre is designed to position your business for success with exceptional connectivity, operational efficiency, and the highest quality construction. Connect better with your customers and employees with direct access to the QEW.

3303 Superior Court Unit A105, Oakville

$4,835,880

W12750984 MLS

Three Oaks Business Centre presents occupiers and investors a rare opportunity to own state-of-the-art industrial condo including mezzanine. Built by Beedie, one of Canada's largest private industrial developers, Three Oaks Business Centre is designed to position your business for success with exceptional connectivity, operational efficiency, and the highest quality construction. Connect better with your customers and employees with direct access to the QEW.

3303 Superior Court Unit A102, Oakville

$4,907,430

W12750980 MLS

Three Oaks Business Centre presents occupiers and investors a rare opportunity to own state-of-the-art industrial condo including mezzanine. Built by Beedie, one of Canada's largest private industrial developers, Three Oaks Business Centre is designed to position your business for success with exceptional connectivity, operational efficiency, and the highest quality construction. Connect better with your customers and employees with direct access to the QEW.

3303 Superior Court Unit A103, Oakville

$3,806,880

W12750974 MLS

Three Oaks Business Centre presents occupiers and investors a rare opportunity to own state-of-the-art industrial condo including mezzanine. Built by Beedie, one of Canada's largest private industrial developers, Three Oaks Business Centre is designed to position your business for success with exceptional connectivity, operational efficiency, and the highest quality construction. Connect better with your customers and employees with direct access to the QEW.

3323 Superior Court Unit C106, Oakville

$4,745,565

W12750956 MLS

Three Oaks Business Centre presents occupiers and investors a rare opportunity to own state-of-the-art industrial condo including mezzanine. Built by Beedie, one of Canada's largest private industrial developers, Three Oaks Business Centre is designed to position your business for success with exceptional connectivity, operational efficiency, and the highest quality construction. Connect better with your customers and employees with direct access to the QEW.

3313 Superior Court Unit B108, Oakville

$2,650,000

4 Beds ⋅ 4 Baths ⋅ W12723170 MLS

Nestled in the heart of Morrison, this distinguished Southeast Oakville residence offers a rare blend of privacy, elegance, and family functionality. Set on a premium 81 x 140 ft lot backing onto King's Forest, the home is framed by a charming wraparound porch and mature landscaping. Freshly renovated and meticulously maintained, the home features hardwood floors throughout, a freshly painted interior, and a bright open-concept kitchen with stainless steel appliances, an oversized island, and floor-to-ceiling windows that flood the space with natural light. The breakfast area flows seamlessly into the family room with a gas fireplace and custom built-ins-ideal for both everyday living and entertaining. The main level offers a large office, easily convertible to a main-floor bedroom, complemented by a 3-piece full bathroom-perfect for extended family, guests, or a nanny suite. The upper level features three full bathrooms, including two private ensuites, along with convenient second-floor laundry. The finished lower level provides additional recreation space and ample storage. Outdoors, the professionally landscaped backyard is surrounded by mature trees, offering exceptional privacy and a serene retreat. Ideally located within walking distance to Oakville's top-ranked schools, including: Oakville Trafalgar HS,EJ James, Maple Grove PS, , St. Vincent's, St. Mildred's, and Linbrook, parks, shopping, and the GO station. Equipped with a security system, irrigation system, and sump pump.A rare opportunity to own a refined family residence in one of Oakville's most prestigious neighborhoods. Don't miss the opportunity to make it your own!!!

427 CAIRNCROFT Road, Oakville

$4,295,000

6 Beds ⋅ 8 Baths ⋅ W12644824 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+++

408 Lakeshore Road W, Oakville

$3,250,000

4 Beds ⋅ 3 Baths ⋅ W12419345 MLS

Nestled south of Lakeshore in the heart of Old Oakvilles historic district, this beautifully restored Georgian-style home, designed by Gren Weis, blends timeless character with modern updates. Steps from the lake, river, and vibrant Downtown, it offers an unmatched lifestyle location.The home boasts exceptional curb appeal with a flagstone path leading to a spacious foyer. Sun-filled interiors feature Farrow & Ball paint, new hardwood on the main level, preserved fir upstairs, smooth ceilings, and recessed LED lighting.The updated kitchen includes a large island, built-in appliances, and desk area. The dining room offers panelled walls, RH sconces, French doors to the garden, and plantation shutters. A charming living room features built-in bookcases, window seat, wood-burning fireplace, and walkouts to a sunroom overlooking the southwest garden and pool. A mudroom and stylish powder room complete the main floor.Upstairs are four bedrooms with ample closets and antique brass hardware. The primary suite offers custom built-ins and a renovated ensuite with heated Carrara marble floors and zero-threshold shower.The fully finished lower level (8 ceilings, slate flooring) adds living space with a media room, workout room, cedar closet, laundry, and storage. Updated mechanicals include a high-efficiency furnace, central AC, 100 AMP panel, irrigation. Cedar roof, new fencing, cobblestone driveway. Outside enjoy a private oasis with saltwater inground pool, brick patios, and landscaped gardens. Steps to the Lake, Oakville Club, Yacht Squadron, Library, Performing Arts Centre, Downtown, and top schools.

53 Thomas Street, Oakville

$4,390,000

5 Beds ⋅ 5 Baths ⋅ W12346602 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

$3,250,000

5 Beds ⋅ 3 Baths ⋅ W10403987 MLS

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

200 WILLIAM Street, Oakville

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

Newest Oakville Properties between $2,500,000 and $5,000,000 for Sale