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Turnkey Winchester Triplex Investment Opportunity

540 MONTICELLO St, Winchester, VA 22601

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For Sale

$605,000

Downtown Winchester triplex with strong cash flow and commuter convenience.

Type:Investment

HighLights

Turnkey triplex investment property in a prime downtown Winchester location.
Strong cash flow with a gross annual rental income of $45,300.
Convenient access to I‑81 and I‑66, less than an hour from Northern Virginia.
Two 2‑bedroom, 1‑bath units feature updated finishes, laundry rooms, and dedicated outdoor space.
The large 5‑bedroom, 2‑bath unit includes two living rooms, full kitchen, laundry, private patio and deck.
Recent renovations include LVP flooring, fresh paint, updated kitchens and baths, newer appliances, new HVAC (2025), and a roof less than 3 years old.

We can help!

Listing Contact

Laura King

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For Sale

$605,000

Downtown Winchester triplex with strong cash flow and commuter convenience.

Type:Investment

Added:: Apr 24, 2026
Days on Market:: 56
Last Refresh:: Apr 24 at 4:17 pm

Property Features for 540 MONTICELLO St

General Information

Standard status: Active
Property subtype: Investment

Building Details

Year Built: 1956

We can help!

Listing Contact

Laura King

Listing agent Laura King License #0225221392

Listing office MarketPlace Realty LLC

Listing date Apr 24, 2026

Source Elliman

Displayed information is deemed reliable but is not guaranteed and should be independently verified.

All listing content including descriptions, pricing, images are the copyrighted material of MarketPlace Realty LLC

HighLights

Turnkey triplex investment property in a prime downtown Winchester location.
Strong cash flow with a gross annual rental income of $45,300.
Convenient access to I‑81 and I‑66, less than an hour from Northern Virginia.
Two 2‑bedroom, 1‑bath units feature updated finishes, laundry rooms, and dedicated outdoor space.
The large 5‑bedroom, 2‑bath unit includes two living rooms, full kitchen, laundry, private patio and deck.
Recent renovations include LVP flooring, fresh paint, updated kitchens and baths, newer appliances, new HVAC (2025), and a roof less than 3 years old.

Overview

Located in downtown Winchester, 540 Monticello Street is a triplex offering a multi-unit investment opportunity. The building contains two 2-bedroom, 1-bath units, each featuring large kitchens, updated finishes, and laundry rooms. One unit is ground level, while the other has access to a deck. The largest unit spans two finished levels connected by an interior staircase, and includes 5 bedrooms, 2 full baths, 2 living rooms, a full kitchen, laundry facilities, and a private patio and deck. This two-level layout is suitable for multi-tenants and may command premium rental rates. Recent renovations include luxury vinyl plank flooring, fresh paint, and updated kitchens and baths. Newer appliances are installed in each unit. The roof is less than 3 years old. New HVAC is scheduled for installation in 2025. Designated parking is available for all units. The property is currently fully leased, generating a gross annual rental income of $45,300. The property is located minutes from I-81 and I-66, and less than an hour from Northern Virginia. The property is somewhat bikeable (bike score 43) and somewhat walkable (walk score 51).

Location Intelligence

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Triplexes

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Location Insight

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Local Demand

City: Winchester
County: Frederick
State: Virginia
Longitude: -78.1886207
Latitude: 39.145098

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For sale
Triplexes
VA
Winchester
22601
540 MONTICELLO St

What type of property is this?

Triplex - Downtown Winchester triplex with strong cash flow and commuter convenience.

Where is this triplex located?

The property is located at 540 MONTICELLO St Winchester, VA.

What is the asking price?

The asking price for this property is $605,000.

What are key features of this property?

This property features: Turnkey triplex investment property in a prime downtown Winchester location.; Strong cash flow with a gross annual rental income of $45,300.; Convenient access to I‑81 and I‑66, less than an hour from Northern Virginia.