View All Latest Oakville 5000+ Sq. Ft. Properties for Sale

Beautiful Pie shape lot/Back 130 ft x 155.19 ft. Ideal family home, move-in ready, cottage like backyard and one of the best investments in Oakville. Approx. 7,476 sqft. of living space! 9' ceiling, 5+2 beds, 5 baths 1+1office. Separate entrance + rough in plumbing/kitchen/bar in basement. 2staircases to the basement, 3 gas firepls. Primary Rm offers ensuite bath w/soaker tub, fireplace, 2 makeup desks, w/closet, separate/showers. All bedrooms have access baths. Kitchen with breakfast area, gas cooktop, granite counter tops, 2 built-in ovens, pantry, butler's pantry. The backyard features saltwater swimming pool, mature trees. Professionally landscaped gardens, covered outdoor sitting room. Nearby private schools, Park, Trails, Glen Abbey golf. lot Area: 10,785.43 ft (0.248 ac) Lot Back 130 ft x Side155.19 ft - Front 44.73 ft x Side118.45 ft

1076 Skyvalley Crescent, Oakville

Listing courtesy of Royal LePage Realty Plus Ltd., Brokerage.

$3,299,900

6 Beds ⋅ 7 Baths ⋅ 40509737 MLS

Nestled just steps away from the picturesque Lakeshore in Oakville, a new 5000 Sq.ft. custom-built masterpiece awaits completion by June 2025. Boasting six spacious bedrooms, this residence is a haven for both relaxation and entertainment. The heart of the home is a state-of-the-art kitchen, perfect for culinary enthusiasts. The open-concept living, family, and dining rooms provide ample space for gatherings, while a two-car garage ensures convenience. A dedicated office space caters to remote work needs, and a fully equipped gym room promotes a healthy lifestyle. The entertainment options are endless with a recreational room, sauna for relaxation, and a home theater for cinematic experiences. This lakeside gem redefines opulence, offering the perfect blend of elegance and functionality for discerning homeowners. This is an opportunity to book a home for your family in Oakville Bronte West and design it as per your likings and needs.

3118 Victoria Street, Oakville

Listing courtesy of Sutton Group Quantum Realty Inc., Brokerage.

$6,780,000

5 Beds ⋅ 8 Baths ⋅ 40500975 MLS

Welcome to a truly luxurious, one of a kind custom-built home, in the heart of Southeast Oakville. This exquisite property features modern elegance and exceptional amenities over 8000 SF of living space, making it an entertainer's dream. The kitchen is a culinary masterpiece with top-end appliances and cabinetry, complemented by a large pantry perfect for the aspiring chef or home entertainer. The open concept design seamlessly connects the living spaces, creating a welcoming atmosphere for family and guests. Convenience is paramount in this home with laundry, a pet wash area, and a well-appointed bathroom on the main level. Upstairs, 4 spacious bedrooms each has an ensuite and ample closet space. The primary bedroom is a luxurious sanctuary with a fireplace, custom walk-in closet, private balcony, and spa-like ensuite. The basement is a recreational haven with a theatre room, wine cellar, wet bar, gym, and a spacious recreation room. An extra room can serve as a bedroom or guest room. Stepping outside, a fully fenced backyard is a true oasis featuring a cabana, pool, hot tub, and outdoor kitchen with BBQ, making outdoor gatherings a breeze. Throughout the home, you will find the timeless beauty of walnut hardwood flooring. This property is a masterpiece of design and functionality, offering an extraordinary lifestyle in Oakville's coveted neighbourhood.

1497 Duncan Road, Oakville

Listing courtesy of HOUSESIGMA INC..

$8,500,000

3 Beds ⋅ 4 Baths ⋅ 40501730 MLS

One of the last house commission of Architect Joseph W. Storey, the two-storey lakefront house is defined by its horizontally brilliant open floor plan, commanding use of materials and seamless integration of indoor and outdoor spaces. The 6,370* square foot home is a masterful use of stone, cedar, glass and concrete. The principal rooms with 10'6" ceiling height and full height glass are positioned to take advantage of long views of lake Ontario creating the feeling of being on top of the water. The lower level has a spacious family room, stone fireplace and additional bedrooms, all with walkouts to a well manicured private landscape area with in-ground concrete pool. It is rare to see a home with this level of construction and design attributes. A true gem!

2366 Carrington Place, Oakville

Listing courtesy of Royal LePage Real Estate Services Phinney Real Est.

$9,988,000

5 Beds ⋅ 6 Baths ⋅ 40500940 MLS

Welcome to Oakville’s finest! Captivating modern masterpiece! This breathtaking mansion with a coveted 105 X 170 foot deep lot of over 10,000 sf of luxurious living space is situated in the most prestigious Oakville south east neighborhood. Tastefully designed with timeless elegance & stately sophistication to impress those who are most meticulous about quality, details and lifestyle. The main floor has a heated marble hallway, specious office with walnut cabinetry and wall paneling. The opulent main floor master bedroom is featured with indulgent marble ensuite, splendid walk-in closets, and glorious bedroom chandeliers, which offers a fabulous, inviting, and restful living space. The gorgeous custom kitchen outfitted with luxury Downsview cabinetry, oversized island with bar seating, and a breakfast area access to a covered patio. The main floor family room has a 16 ft intricate ceiling and a sumptuous glass window overlooking west facing private backyard with in-ground swimming pool. Three more large bedrooms w/ custom designed ensuites & walk-in closets complete the second level. The fully loaded lower level offers the 5th bedroom with ensuite ,recreation room, billiards room, wet bar &wine tasting room, fireplace, gym, office and laundry room with central island. Private elevator access to all levels The concrete driveway has parking for 10 cars. Ideally located close to Downtown Oakville, top-rated schools, shopping, arts centre, community centre and so much more.

76 Barringham Drive, Oakville

Listing courtesy of Right At Home Realty, Brokerage.

$6,750,000

6 Beds ⋅ 5 Baths ⋅ 40495699 MLS

233 King Street is truly one of Old Oakville’s finest estate homes. Nestled amid a canopy of trees and elegant manicured gardens on the corner of Dunn & King, this landmark home offers over 6900 sq. ft. of sophisticated living space on 4 levels. Situated on 0.351 acres of picturesque grounds, this exceptional home is brimming with character details such as the original stone floors in the sunroom, stained glass windows, 2 woodburning fireplaces with intricate mantles, and exquisite plaster moldings that harken back to a bygone era. The kitchen is well-appointed with Egyptian marble counters, built-in appliances, and hardwood floors. Take your cup of tea from the inviting breakfast room out to the shaded patio under a wisteria-covered pergola. This home offers gracious living spaces, whether you're hosting grand soirées in the formal living and dining rooms or seeking quiet moments of reflection in the family room and music/sunroom, both of which provide an abundance of natural light through their vast windows. On the second level, the primary bedroom retreat includes a sitting room, dressing room, walk-in closet, and a 5-pc ensuite. Two additional bedrooms, a full bathroom with period detailing, and a traditional linen room complete this level. The third floor is comprised of 3 more bedrooms, 2 bathrooms, and a cedar walk-in closet. This historical estate seamlessly marries the elegance of its past with the conveniences of modern living. It's a rare opportunity to own a piece of history while enjoying spacious living and the tranquility of mature gardens, stone patios, and the saltwater concrete pool and spa. Don't miss the chance to make this remarkable property your own in prime downtown Oakville with the Lake and its plethora of shops and restaurants just a stroll away.

233 King Street, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc., Brokerage.

$13,750,000

5 Beds ⋅ 7 Baths ⋅ 40489922 MLS

Magnificent Gated Estate Nestled on a Meticulously Landscaped 3/4 Acre Lot, on S/E Oakville’s Coveted Street of Dreams.This Architectural Monument was Flawlessly Designed & Built by one of the world's most Renowned Master Builders of Uber Luxury Residences. Over 11,000 sq ft. 4.1 Beds, 5.2 Baths. Indiana Buff Limestone Construction, Slate Roof, Copper Eaves & Downspouts. Painstaking Attention to Detail is Clearly Evident. Exquisite Finishes T/O inc Intricately Detailed Walls & Ceilings, Exotic Woods, Imported Marbles & Suede & Leather Wall Treatments. Dramatic Foyer w 18 ft Silver-Leaf, Hand-Painted Rotunda & Imported Murano Glass Chandelier. Grandiose 2 Storey Grt Rm w 24 ft 2 Sided F/P. Awe-Inspiring Library w 2 Walls of Built-Ins, Wet Bar w Marble Counters & Inlay & Drain-less Trough Sink. Gourmet Chef’s Dream Kitchen Features Lrg Center Island w Breakfast Bar, Flr to Ceiling Ebony & Walnut Cabinetry w Mirrored Uppers, Full Pantry, Statuario Marble Counters & Backsplash, Custom Paneled Top Of The Line Appliances & Sunny Dining Area. Adjacent Serving Pantry Complete w b/in Coffee Station, Prep Sink & Loads of Addtl Cabinetry w Integrated Seamless Door. Formal Din Rm w Ornate Coved Ceiling, Paneled & Mirrored Walls & Floor to Ceiling Wall of Windows Overlooking the Front Gardens. Jaw-Dropping Powder Rm w Coved Mirrored Ceiling, Mahogany Cabinetry & Swarovski Crystal Handles. Unique Custom Elevator Lined in Faux Ostrich. 2nd Level hosts a Grand Primary Retreat w Lavish 6 pc Ensuite & Boutique Style Dressing Room, 3 Considerable Bedrooms w Luxurious Ensuites & Opulent Laundry Rm. Impressive LL Reveals 5th Bedroom, 3 Piece Ensuite, Office, Powder Rm, Recreation Area, Gym, Wet Bar, 1100+ Bottle Wine Rm & S/O/T/A Home Theatre. Resort-Inspired Rear Yard w I/G S/W Pool w Cascading Jets, Wtrfl Spa, Cabana & Summer Shower. Steps to Lake & Downtown. Walking Distance to St Mildrid’s Lightbourne & Linbrook School. 5 min Drive to Appleby College. Excellent School District!!

199 Chartwell Road, Oakville

Listing courtesy of Sotheby's International Realty Canada, Brokerage.

$3,995,000

4 Beds ⋅ 6 Baths ⋅ 40490149 MLS

One of the last remaining lakefront lots, ready for development, in Southwest Oakville. Located in the sold-out Oak & Lake subdivision, a historic lakefront property that has been subdivided into 18 estate sized lots. This just under half acre, pie shaped lot, offers ideal proportions for a custom-built home. With 138’ of waterfront shoreline, views from almost every room will be that of serene Lake Ontario. Take in the sunrise over the water from your backyard. This lot is over 21,600 square feet, with RL1-0 zoning, allowing for 29% residential floor area – allowing you to build over 6,250 square feet above grade. Lakefront building lots are super rare as are lots that are larger than the typical 15,000 square feet. This is arguably the best lot in a brand-new plan of subdivision where you will be surrounded by all new custom-built homes. Renderings on the listing are for a home designed by John Willmott with a main floor principal bedroom. A landscaping rendering for this plan is also attached. This is an ideal location situated in between some of Oakville most desired destinations. Downtown Oakville, Kerr Village and Appleby College, just to name a few, are all within walking distance. It’s also short drive to the both the QEW and Oakville Go Train Station. A true lifestyle property.

21 Pebbleridge Place, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd., Brokerage.

$7,500,000

5 Beds ⋅ 7 Baths ⋅ 40489986 MLS

Exceptional gated estate home nestled on a spectacular 100’ x 225’ lot on Oakville’s most coveted street of dreams, completely reconstructed in 2020 with over 7500 sf luxury finished living space on trend finishes & manicured gardens with the timeless character and curb appeal. The main level boasts airy kitchen w/ finest cabinetry opens to a spacious family room that’s meticulously designed for entertaining, the office, formal living room, piano lounge and 3 season screened Muskoka room.Luxuriate in the principal suite w/linear gas fireplace, dual ensuites, separate walk-in closets & a boutique-like dressing room.Private walk out balcony overlooks the private Muskoka like yard with towering trees. All 3 additional upper level bedrooms each have private en-suites and generous closets.Take the main floor slide or the stairs to a fully finished lower level with recreation, games rooms, gym, 5th bdrm, full bathroom & plenty of storage.2 laundry rooms provide optimal laundry efficiency.

200 Chartwell Road, Oakville

Listing courtesy of Re/Max Hallmark Alliance Realty.

$10,900,000

6 Beds ⋅ 10 Baths ⋅ 40487354 MLS

Timeless elegance and quality craftsmanship is what describes 247 Donessle Drive located in the coveted Old Oakville. This one of a kind home boosts over 11,000 sq. ft. of exceptional living space across all levels. Designed by Architect, Bill Hicks, the exterior of Donessle celebrates the use of time-honoured materials such as Indiana limestone, natural stone, granite and copper detailing. The interior of the home designed by Robin Nadel, is full of luxurious finishing’s from detailed wall paneling, millwork, vaulted ceilings, natural stones and a classic timeless colour scheme. Every part of this home was created with such thought and exquisite sophistication. The main principle rooms are finely designed with unique wall panelling; plaster mouldings, and luxurious wallpaper. Walnut hardwood flooring and Crema Marfil marble carry you throughout. The high functioning gourmet kitchen is an entertainer’s dream. Designed by Downsview with custom cabinetry, an oversized island, marble counters, and integrated appliances - what better space for any entertaining. The primary bedroom is located on the second floor with stunning views from the balcony to the rear grounds The room is fully outfitted with two dressing rooms, an elegant ensuite with a cast iron soaking tub, a walk-in shower, dual vanities, and a separate water closet. Additional bedrooms are finely styled with ensuite privileges. Down the hall, you find the perfect spot for the kids in their own lounge. Enjoy the walk-up from the lower level that includes everything that one could desire. From a full spa, gym, kitchen, old world wine cellar, theatre room, wet bar, two play rooms and recreation room. Experience a summer resort in your own backyard with the utmost privacy with professionally manicured landscaping. The backyard consists of a salt-water pool finished in mosaic glass tile, cabana with outdoor shower, hot tub with a waterfall feature and an outdoor terrace with wood burning fireplace.

247 Donessle Drive, Oakville

Listing courtesy of Century 21 Miller Real Estate Ltd., Brokerage.

$5,699,000

8 Beds ⋅ 12 Baths ⋅ 40485012 MLS

Build the home of your dream! Spectacular one-of-a-kind building lot situated on a signature street set among some of Oakville’s finest real estate. This 27,770 sqft (0.638 acre) parcel gives the ultimate in privacy with mature trees and plantings. Fully fenced with a combination of quality wood and wrought iron fencing. Situated within walking distance to downtown Oakville’s shops and restaurants, great school district and easy access to highway and GO train. Rendering and plans available for 2 different homes. One of which was site plan approved under title. Call for further details. Large parcels of land such as these are rare and few. Don’t miss your chance to build the home of your dreams! Lot is service ready.

283 Balsam Drive, Oakville

Listing courtesy of RE/MAX Escarpment Realty Inc., Brokerage.

$5,800,000

7 Beds ⋅ 8 Baths ⋅ 40472611 MLS

Experience Luxury living in this custom home, designed by Bill Hicks, located on one of the most sought-after streets in South Oakville. Situated on a 110 x 141 ft large premium lot, backing onto a lush ravine! Offers approx. 5,300 sq.ft above ground plus 2,200 sq. ft. in lower level. This 5 bedroom/8 washroom home can potentially fit for two extended families with separate entrances, two staircases, and pocket doors that separate the living areas. Gourmet kitchen overlooking backyard features top of the line appliances: Sub-zero paneled fridge, Thermador gas stove, Miele Dishwasher, custom Falcon cabinetry and granite countertop. Kitchen open to large great room with vaulted ceilings and gas fireplace. Main floor also features, living room with fireplace, Dining room with servery and walk-in pantry, office, laundry room with laundry shoot from 2nd level and 2 washrooms. Master Suite features an electric fireplace and a Private Sitting Room, large walk-in closet and 5 pc ensuite. The rest of 4 bedrooms with private en-suite bathrooms. Lower Level features a recreational room, Theatre, Designer Gym, Games Room, and 2 additional bedrooms and 2 additional washrooms (3 pc and 2 pc). Enjoy the private backyard with heated inground Pool, BBQ area, cabana, a large porch. Built-in speaker system (interior and exterior), Automated Irrigation System, Security Surveillance System. Please See Features Brochure For Extensive List Of Inclusions. Steps To Lake And Appleby College, mins from downtown Oakville, parks, trails, community centres, and the QEW.

1176 Westdale Road, Oakville

Listing courtesy of Right At Home Realty, Brokerage.

$11,488,888

5 Beds ⋅ 9 Baths ⋅ 40468947 MLS

Welcome to 27 Park Avenue situated in the Orchard Beach community of Old Oakville. It’s the epitome of a lakeside home styled in the architecture of the Hamptons surrounded by towering trees, perennial gardens and inspiring lake views. Designed by Gus Ricci and select finishes by Studio H. Over 10,000 sq ft of living space on a massive lot with excess of one million dollars spent on landscaping which includes a commercial grade infinity pool, well appointed 950 sq ft pool house with a bar, fireplace, vaulted ceiling and bathroom with shower. It also boasts your own putting green and in the ground trampoline. The interior of the home features finishes specified to the highest level. Marble heated floors, 10 inch wide plank white oak flooring, stylish light fixtures, high ceilings on all 3 levels, 4 + 1 bedrooms, 2 with study areas, 9 custom designed bathrooms, gorgeous kitchen with a La Cornue oven and high end appliances and a large pantry. The home is equipped throughout with a sophisticated security and sound system. The main floor is completed with parlour, office, laundry room, formal dining room and servery, great room and mud room off the heated garage. The staircase is the highlight of the home. The fully finished basement includes two full baths, a gym, extensive wine cellar, theatre room and bar, bedroom, mechanical room, media room, a safe room, a cedar closet, ample storage areas and stairs to the garage. Park Avenue named for the horse and buggies that use to park on it when attending the polo matches in the 1800s. It was once the home of many cottagers who visited in the summer to enjoy Orchard Beach on Lake Ontario. So much history for where this timeless lakeside home resides. With a short walk to town, its proximity to the lake and the outstanding finishes throughout, it is truly one of the most gracious new homes in the area.

27 Park Avenue, Oakville

Listing courtesy of RE/MAX Aboutowne Realty Corp., Brokerage.

$22,999,000

6 Beds ⋅ 8 Baths ⋅ 40408434 MLS

A Vibrant Community In The Greater Toronto Area, Oakville Attracts Many Who Need To Get Away From Somewhere, And At The Same Time, Those Who Need To Move To A New Location. For Over 100 Years, People Have Come To Oakville Looking For The Lakeside Life, People Have Stayed In Oakville Because This Place Captures Your Heart And Draws You In With Its Setting, Culture, And Investment Opportunities. This Lake-Facing Villa With A Tennis Court In South East Of Oakville Stands Majestically In An Exclusive Context Made Of Only Luxury Properties. Designed By Hicks-Pettes Architects, This European Style Estate Has An Sweeping View Of The Lake And Provide More Than 12,300 S.F. Living Space With 6 Bedrooms And 8 Bathrooms, 6 Walkouts, 2 Patios, Garden, Tennis Court And Lakeside 2500 S.F. Terrace, It Is A Perfect Place To Live On The Shoreline. Information Package Upon Request.

1092 Argyle Drive, Oakville

Listing courtesy of Sotheby's International Realty Canada, Brokerage.

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5000+ Sq. Ft. Oakville Real Estate

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