Welcome to 155 Chestnut Street, a beautifully maintained and extensively upgraded triplex in the heart of Wolseley, one of Winnipeg's most beloved and walkable neighbourhoods.

Offering 2,428 square feet of living space across three suites, this is far more than a typical income property. The current and previous owners have approached this building as long-term stewards, investing thoughtfully in both the infrastructure and the living experience while preserving the character, craftsmanship, and integrity of this historic home.

For investors, this is the type of property that rarely becomes available. For owner-occupiers, an exciting opportunity awaits with the main floor suite becoming vacant July 1.

💰 Strong Income Potential

Current rental income includes:

• Main Floor Suite: Potential rent of $1,985+ per month (vacant July 1)
• Second Floor Suite: $1,630/month with lease secured to July 2027
• Third Floor Suite: $920/month with lease secured to August 2027

Located minutes from the University of Winnipeg, Health Sciences Centre, downtown, transit routes, restaurants, and local shops, the property consistently attracts quality long-term tenants and experiences minimal vacancy.

✨ Owner-Occupy or House Hack

The spacious main floor suite is a standout feature.

Fully renovated during the 2006 conversion, it offers five bedrooms, two full bathrooms, bright living spaces, beautiful character details, and exclusive use of the single garage.

Whether you're looking to live in one suite while collecting rental income or maximize cash flow as a full investment property, the flexibility here is exceptional.

🔨 Extensive Capital Improvements

Significant investments have been made throughout the property, including:

✔ Legal triplex conversion and full main floor renovation (2006)
✔ Complete rewiring (2006)
✔ Exterior waterproofing around the entire perimeter
✔ Weeping tile installation
✔ Sump pump and backwater valve
✔ Exterior rigid insulation
✔ PVC slider windows
✔ Renovated kitchens and bathrooms
✔ High-efficiency furnace and central air conditioning (2022)
✔ Hot water tank (2021)
✔ Exterior painting (2025)

In 2018, over $30,000 was invested into the upper suites, including updated kitchens with quartz countertops, matte black cabinetry, new fixtures, appliances, flooring, bathroom renovations, and maple hardwoods.