Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location!
Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers convenience, charm, and long-term value.

The building features two 2-Bedroom, 1-Bath Units – Each offers large Kitchens, updated finishes, and their own Laundry Rooms. One of the units is ground level, and the other 2nd-Level unit has access to its own deck space. The largest unit of the three features two finished levels, connected with an interior staircase, 5-Bedrooms, 2 Full Baths, 2 Living Rooms, a Full kitchen, Laundry, and access to it’s own private patio & deck. It’s a unique two-level layout, perfect for multi-tenants and/or premium rental rates.
Recent renovations throughout the last few years include:
Luxury vinyl plank (LVP) flooring, fresh paint, and updated kitchens and baths
Newer appliances in each unit
A roof less than 3 years old
Designated parking for all units
With all units currently leased, this is a true turnkey investment with reliable income and minimal immediate maintenance needs. This well-maintained building features three fully occupied units, bringing in a current gross annual rental income of $43,200.
Whether you’re looking to grow your portfolio or occupy a unit while renting the others, or the potential for a short-term rental, this property checks all the boxes!