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!
For sale
$605,000
540 Monticello St, Winchester, VA 22601
9beds
4baths
4,396sqft
Triplex
Built in 1956
-- sqft lot
$-- Zestimate®
$138/sqft
$-- HOA
What's special
- 6 days
- 111
- 13
Zillow last checked:
Listing updated:
Listed by:
Laura King 540-409-8683,
MarketPlace REALTY 540-450-2747
Source: Bright MLS,MLS#: VAWI2011668
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 9
- Bathrooms: 4
Basement
- Area: 0
Heating
- Heat Pump, Electric
Cooling
- Heat Pump, Electric
Appliances
- Included: Dishwasher, Microwave, Oven/Range - Electric, Water Heater, Electric Water Heater
- Laundry: Washer/Dryer Hookups Only
Features
- 2nd Kitchen, Additional Stairway, Bathroom - Tub Shower, Breakfast Area, Combination Dining/Living, Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Eat-in Kitchen, Kitchen - Table Space, Dry Wall
- Flooring: Carpet, Laminate
- Doors: Insulated, Six Panel
- Windows: Double Pane Windows
- Has basement: No
- Has fireplace: No
Interior area
- Total structure area: 4,396
- Total interior livable area: 4,396 sqft
Property
Parking
- Parking features: Driveway, Assigned
- Has uncovered spaces: Yes
- Details: Assigned Parking
Accessibility
- Accessibility features: None
Features
- Pool features: None
- Frontage type: Road Frontage
Lot
- Size: 3,999 Square Feet
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 3300227
- Zoning: B2
- Special conditions: Standard
Construction
Type & style
- Home type: MultiFamily
- Architectural style: Other
- Property subtype: Triplex
Materials
- HardiPlank Type
- Foundation: Slab
- Roof: Architectural Shingle
Condition
- Very Good
- New construction: No
- Year built: 1956
- Major remodel year: 2007
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Available, Multiple Phone Lines
Community & HOA
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $138/sqft
- Tax assessed value: $461,600
- Annual tax amount: $3,669
- Date on market: 9/21/2026
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Total actual rent: 45000
- Income includes: Apartment Rentals, Laundry, Parking
- Road surface type: Paved
Estimated market value
Not available
Estimated sales range
Not available
$1,343/mo
Price history
| Date | Event | Price |
|---|---|---|
| 9/22/2026 | Listed for sale | $605,000$138/sqft |
Source: | ||
| 7/15/2026 | Listing removed | $605,000$138/sqft |
Source: | ||
| 2/17/2026 | Listed for sale | $605,000$138/sqft |
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| 1/4/2026 | Listing removed | $605,000$138/sqft |
Source: | ||
| 10/24/2025 | Listed for sale | $605,000-1.6%$138/sqft |
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| 10/22/2025 | Listing removed | $615,000$140/sqft |
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| 7/25/2025 | Price change | $615,000-1.6%$140/sqft |
Source: | ||
| 4/23/2025 | Listed for sale | $625,000+7.8%$142/sqft |
Source: | ||
| 2/1/2025 | Listing removed | $579,900$132/sqft |
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| 1/7/2025 | Price change | $579,9000%$132/sqft |
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| 1/3/2025 | Price change | $579,9250%$132/sqft |
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| 12/6/2024 | Price change | $579,9500%$132/sqft |
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| 12/5/2024 | Price change | $579,9750%$132/sqft |
Source: | ||
| 9/8/2024 | Listed for sale | $580,000$132/sqft |
Source: | ||
| 7/26/2023 | Listing removed | -- |
Source: Zillow Rentals Report a problem | ||
| 7/15/2023 | Listed for rent | $1,000-9.1% |
Source: Zillow Rentals Report a problem | ||
| 11/3/2022 | Listing removed | -- |
Source: Zillow Rental Manager Report a problem | ||
| 10/26/2022 | Listed for rent | $1,100+15.8% |
Source: Zillow Rental Manager Report a problem | ||
| 7/30/2021 | Listing removed | -- |
Source: Zillow Rental Manager Report a problem | ||
| 7/23/2021 | Listed for rent | $950+2.7% |
Source: Zillow Rental Manager Report a problem | ||
| 3/10/2021 | Listing removed | -- |
Source: Owner Report a problem | ||
| 12/4/2020 | Price change | $925+2.8% |
Source: Owner Report a problem | ||
| 10/20/2020 | Listed for rent | $900 |
Source: Owner Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2026 | $3,670 | $461,600 |
| 2025 | $3,670 +17.8% | $461,600 +23% |
| 2024 | $3,115 | $375,300 |
| 2023 | $3,115 +36% | $375,300 +52.4% |
| 2022 | $2,290 | $246,200 |
| 2021 | $2,290 +2.2% | $246,200 |
| 2020 | $2,240 | $246,200 |
| 2019 | $2,240 | $246,200 |
| 2018 | $2,240 +9.2% | $246,200 |
| 2017 | $2,051 | $246,200 +9.2% |
| 2016 | $2,051 | $225,400 |
| 2015 | $2,051 +85.6% | $225,400 -3.1% |
| 2014 | $1,105 | $232,700 |
| 2013 | -- | $232,700 |
| 2012 | -- | $232,700 |
| 2011 | -- | $232,700 |
| 2010 | -- | $232,700 |
| 2009 | -- | $232,700 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 22601
Nearby schools
Schools provided by the listing agent
- District: Winchester City Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.




