About 540 Monticello St
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 The roof less than 3 years old New HVAC installed (2025) 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 $45,300. 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!
Features of 540 Monticello St
| MLS® # | VAWI2011668 |
|---|---|
| Price | $605,000 |
| Bathrooms | 0.00 |
| Square Footage | 4,396 |
| Acres | 0.09 |
| Year Built | 1956 |
| Type | Multi-Family |
| Sub-Type | Triplex,Other |
| Style | Other |
| Status | Active |
Community Information
| Address | 540 Monticello St |
|---|---|
| City | WINCHESTER |
| County | WINCHESTER CITY-VA |
| State | VA |
| Zip Code | 22601 |
Amenities
| Amenities | 2nd Kitchen, Additional Stairway, Bathroom - Tub Shower, Breakfast Area, Carpet, Combination Dining/Living, Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Kitchen - Eat-In, Kitchen - Table Space, Washer/Dryer Hookups Only |
|---|---|
| Utilities | Cable TV Available, Multiple Phone Lines |
| Parking Spaces | 5 |
| Parking | Paved Driveway, Assigned |
| Is Waterfront | No |
Interior
| Appliances | Dishwasher, Microwave, Oven/Range - Electric, Washer/Dryer Hookups Only, Water Heater |
|---|---|
| Heating | Heat Pump(s) |
| Cooling | Heat Pump(s) |
| Has Basement | No |
| Fireplace | No |
| # of Stories | 2 |
Exterior
| Exterior | HardiPlank Type |
|---|---|
| Lot Description | Road Frontage |
| Windows | Double Pane |
| Roof | Architectural Shingle |
| Construction | HardiPlank Type |
| Foundation | Slab |
School Information
| District | WINCHESTER CITY PUBLIC SCHOOLS |
|---|---|
| High | CALL SCHOOL BOARD |
Additional Information
| Date Listed | September 21st, 2026 |
|---|---|
| Days on Market | 2 |
| Zoning | B2 |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
| Listing Ownership | Fee Simple |
Listing Details
| Office | MarketPlace REALTY |
|---|
