# 540 MONTICELLO Street, Winchester, VA 22601 > **TL;DR:** multi-family, $605,000 ($138/sqft), built 1956, 4,396 sqft. Est. $3,235/mo. Listed 41 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $605,000 | | Price/sqft | $138 | | Square Feet | 4,396 | | Year Built | 1956 | | Lot Size | 3,999 sqft (0.09 acres) | | Property Type | Multi-Family (Triplex) | | Status | Active | | Days on Market | 41 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $3,059 | | Estimated Insurance | $176 | | **Total** | **$3,235** | ## Nearby Schools - **High:** CALL SCHOOL BOARD ## Property Highlights - Built in 1956 - 0.09 acre lot ## Description ### Agent Description 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! ## Location - **Address:** 540 MONTICELLO Street, Winchester, VA 22601 - **County:** WINCHESTER CITY - **Coordinates:** 39.14512, -78.18863 - **Google Maps:** https://www.google.com/maps?q=39.14512,-78.18863 ## Listing Agent - **Name:** Laura King · **License:** 0225221392 - **Brokerage:** MarketPlace Realty LLC - **Broker Phone:** (540) 450-2747 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/540-Monticello-St_Winchester_VA_22601_M92218-77335?f=listhub&s=TRENDPA&m=VAWI2011668&c=propsimple) ## Photos ![540 MONTICELLO Street - Photo 1](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f3733967098r.jpg) ![540 MONTICELLO Street - Photo 2](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f3974812776r.jpg) ![540 MONTICELLO Street - Photo 3](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f529133333r.jpg) ![540 MONTICELLO Street - Photo 4](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f599021189r.jpg) ![540 MONTICELLO Street - Photo 5](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f1012769742r.jpg) ![540 MONTICELLO Street - Photo 6](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f3134049251r.jpg) ![540 MONTICELLO Street - Photo 7](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f522266540r.jpg) ![540 MONTICELLO Street - Photo 8](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f1624677013r.jpg) ![540 MONTICELLO Street - Photo 9](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f3082062534r.jpg) ![540 MONTICELLO Street - Photo 10](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f4035273856r.jpg) ![540 MONTICELLO Street - Photo 11](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f3215788157r.jpg) ![540 MONTICELLO Street - Photo 12](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f1524732922r.jpg) ![540 MONTICELLO Street - Photo 13](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f773122422r.jpg) ![540 MONTICELLO Street - Photo 14](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f3018553744r.jpg) ![540 MONTICELLO Street - Photo 15](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f3831876420r.jpg) ![540 MONTICELLO Street - Photo 16](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f94987747r.jpg) ![540 MONTICELLO Street - Photo 17](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f808160842r.jpg) ![540 MONTICELLO Street - Photo 18](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f3524704302r.jpg) ![540 MONTICELLO Street - Photo 19](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f4254703378r.jpg) ![540 MONTICELLO Street - Photo 20](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f2696885056r.jpg) ![540 MONTICELLO Street - Photo 21](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f3415745562r.jpg) ![540 MONTICELLO Street - Photo 22](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f3139504620r.jpg) ![540 MONTICELLO Street - Photo 23](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f1153250300r.jpg) ![540 MONTICELLO Street - 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Photo 54](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f2143396951r.jpg) ![540 MONTICELLO Street - Photo 55](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f3207689656r.jpg) ![540 MONTICELLO Street - Photo 56](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f4198647522r.jpg) ![540 MONTICELLO Street - Photo 57](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f2165390989r.jpg) ![540 MONTICELLO Street - Photo 58](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f2149584320r.jpg) ![540 MONTICELLO Street - Photo 59](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f828237787r.jpg) ![540 MONTICELLO Street - Photo 60](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f1992220962r.jpg) ![540 MONTICELLO Street - Photo 61](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f355069376r.jpg) ![540 MONTICELLO Street - Photo 62](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f100230362r.jpg) ![540 MONTICELLO Street - Photo 63](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f1330013021r.jpg) ![540 MONTICELLO Street - Photo 64](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f3944005952r.jpg) ![540 MONTICELLO Street - Photo 65](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f1367275706r.jpg) ![540 MONTICELLO Street - Photo 66](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f1921411889r.jpg) ![540 MONTICELLO Street - Photo 67](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f1083048602r.jpg) ![540 MONTICELLO Street - Photo 68](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f3842449391r.jpg) ![540 MONTICELLO Street - Photo 69](http://lh.rdcpix.com/1cee44574687ef893c22b942c6b5b16al-f2195481065r.jpg) --- **MLS#:** VAWI2011668 | **Updated:** 2026-10-20 **Source:** listhub *Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/540-monticello-street-winchester-va-22601-d9be369d8d484816bf8af42a3688db3c) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/540-monticello-street-winchester-va-22601-d9be369d8d484816bf8af42a3688db3c#listing", "url": "https://www.propertysimple.ai/listing/540-monticello-street-winchester-va-22601-d9be369d8d484816bf8af42a3688db3c", "name": "540 MONTICELLO Street, Winchester, VA 22601", "description": "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. 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