# 185 LOUDOUN Street N, Winchester, VA 22601

> **TL;DR:** commercial, $1,395,000, built 1900.
> A/C. Est. $7,461/mo. Listed 2 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $1,395,000 |
| Year Built | 1900 |
| Lot Size | 1,873 sqft (0.04 acres) |
| Property Type | Commercial (Office) |
| Status | For Sale |
| Days on Market | 2 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $7,054 |
| Estimated Insurance | $407 |
| **Total** | **$7,461** |

## Key Amenities

- A/C

## Property Highlights

- Built in 1900
- 0.04 acre lot
- 500 parking spaces

## Description

### Agent Description
Legacy Investment Opportunity: Prime, Turn-Key Asset in Downtown Historic District! 7500 SF over four floors, located on the celebrated Walking Mall, Winchester, VA, the fastest-growing metro area in Virginia! This historic building has been fully modernized and is 100% occupied with a strong leasing history. List Price: $1,395,000. CAP Rate: 7.5%. Annual Net Rent: $106K. The property features a strategic mix of four stabilized leases, including prime ground-floor retail and Class A office suites across the second, third, and fourth floors. This is a very rare income opportunity!

## Location

- **Address:** 185 LOUDOUN Street N, Winchester, VA 22601
- **County:** WINCHESTER CITY
- **Neighborhood:** NONE AVAILABLE
- **Coordinates:** 39.18222788, -78.16636485
- **Google Maps:** https://www.google.com/maps?q=39.18222788,-78.16636485

## Listing Agent

- **Name:** Gillian Joy Greenfield
- **Brokerage:** Coldwell Banker Premier
- **Phone:** 5409743927

## Primary Photo

![185 LOUDOUN Street N - Primary Photo](http://lh.rdcpix.com/8a4aad1c6dfd9a509dc39cdda781d756l-f1379799736r.jpg)

*18 total photos available on [listing page](https://www.propertysimple.ai/listing/185-loudoun-street-n-winchester-va-22601-i2011270)*

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**MLS#:** VAWI2011270 | **Updated:** 2026-08-02
**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/185-loudoun-street-n-winchester-va-22601-i2011270)

---

## Structured Data

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  "@context": "https://schema.org",
  "@type": "RealEstateListing",
  "name": "185 LOUDOUN Street N, Winchester, VA 22601",
  "description": "Legacy Investment Opportunity: Prime, Turn-Key Asset in Downtown Historic District! 7500 SF over four floors, located on the celebrated Walking Mall, Winchester, VA, the fastest-growing metro area in Virginia! This historic building has been fully modernized and is 100% occupied with a strong leasing history. List Price: $1,395,000. CAP Rate: 7.5%. Annual Net Rent: $106K. The property features a strategic mix of four stabilized leases, including prime ground-floor retail and Class A office suite",
  "url": "https://www.propertysimple.ai/listing/185-loudoun-street-n-winchester-va-22601-i2011270",
  "image": "http://lh.rdcpix.com/8a4aad1c6dfd9a509dc39cdda781d756l-f1379799736r.jpg",
  "datePosted": "2026-07-31",
  "price": 1395000,
  "priceCurrency": "USD",
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    "streetAddress": "185 LOUDOUN Street N",
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    "addressRegion": "VA",
    "postalCode": "22601",
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```