140 Chartwell Road

Iconic Old Oakville Estate

Discover one of Old Oakville’s grandest and most legendary estates! Spanning over 1.5 acres of meticulously landscaped grounds, this property exudes elegance and timeless charm. The journey begins at a stately cobblestone-gated entrance, leading down a picturesque, winding driveway that sets the stage for an authentic estate experience.  

Boasting almost 9,000 sq. ft of combined total living space this quintessential traditional family estate has recently underwent millions in renovations & upgrades over recent years. The masterfully designed interior preserves the integrity and craftsmanship of the original home while seamlessly incorporating all the modern luxuries and amenities required by today's families.  

The main level is comprised of both formal and informal entertaining areas. Host and entertain guests in either the private dining or formal living room, sit back and relax with the family in the open concept kitchen and great room or sneak away for some alone time in the private office or sunroom. Rounding out the main floor is a spacious laundry room, eating area, sitting area, mudroom and two powder rooms.  

The upper level is home to five bedrooms and three bathrooms.  A large and spacious primary suite features vaulted ceilings, automated blinds, natural gas fireplace, spacious walk-in closet, reading area and a 5pc private ensuite.  

A nanny suite with separate wet bar or kitchenette area is also on this level, located above the garage and can be accessed by a second staircase leading from the back hall or main floor mudroom area.   

Some of the redesign includes a lower level reno offering an in-law suite with 3pc bath, kitchenette, bedroom with fireplace as well as the highly desired theatre room.  Additional storage, craft room and exercise room are also located on the lower level.   

Step into the ultimate outdoor sanctuary on this picturesque estate, offering an array of inviting spaces designed for both entertaining and relaxation. Enter a separately gated pool area, complete with a flagstone patio, a built-in BBQ, and a luxurious heated pool cabana with over 500 square feet of living space. The cabana boasts a cozy sitting area, two changing rooms, a shower, and a two-piece bathroom—perfect for hosting guests in style. Wander through the secluded garden, where heated walkways guide you past hand-picked sculptures symbolizing the four classical elements: Earth, Water, Air, and Fire—a truly enchanting retreat. Whether you’re hosting elegant summer garden parties or simply seeking a tranquil escape, this space delivers unparalleled charm. Even pets have their own dedicated oasis with a K9 synthetic grass area that’s drainable, cleanable, and anti-microbial. This estate offers a one-of-a-kind outdoor experience that’s sure to impress at every turn!  

Stay connected to your home with your state-of-the-art home automation system allows for personal customization and controlling of lights, blinds, front gates, home audio/video, climate & security.  

Just a short stroll away from downtown Oakville and Lake Ontario. Preferred school district with top rated public and private schools within walking distance.  

Don't miss this rare opportunity to own one of Oakville's most picturesque estates—a property that blends timeless elegance with unparalleled beauty. Your dream home awaits!  

LOT SIZE: 178.38' x 371.05' x 177.47' x 368.30'