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$1,395,000 Just Listed

  • For Sale
  • Active
  • Commercial Service
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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!

Full Property Details for 185 Loudoun Street N

General

  • Price: $1,395,000
  • Taxes: $6,402 (2025)
  • Status: Active
  • Type: Commercial Service
  • Source: BrightMLSMidAtlantic
  • MLS ID: VAWI2011270
  • Updated: 7/31/2026
  • Added to Site: 2 day(s) ago

Business

  • Business Type: Professional, Other/General Retail

Parking

  • Total Spaces: 500
  • Parking Type: On Street

Location

  • County: WINCHESTER CITY
  • Driving Directions: Corner of North side of Walking Mall and Piccadilly Street
  • City Limits: Yes

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: 90% Forced Air
  • Heating Fuel: Natural Gas, Electric
  • Water Heater: Natural Gas

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Construction: Brick
  • Building Size: 7500
  • Year Built: 1900
  • Year Built Source: Estimated
  • Property Condition: Excellent

Unit Information

  • # Tenants: Multiple

Lot Features

  • Lot Size (Acres): 0.04
  • Lot Size (Sq. Ft.): 1,873
  • Lot Size Source: Estimated
  • Zoning: B1

Financial Considerations

  • Price Per Sq. Ft.: $186
  • Tax w/Assessment: $624,600
  • Tax Amount: $6,402
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple

Listed by Coldwell Banker Premier, Gillian Joy Greenfield

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Listing agent

— 185 Loudoun Street N —

  • Gillian Joy Greenfield

    Coldwell Banker Premier

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 185 Loudoun Street N

School District:Winchester City Public Schools
NameGradesDistance
John Kerr Elementary
427 Meadow Branch Avenue, Winchester, VA 22601
PK-41.5 mi
Daniel Morgan Middle School
48 South Purcell Avenue, Winchester, VA 22601
7-80.9 mi
John Handley High School
425 Handley Boulevard, Winchester, VA 22601
9-120.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 185 Loudoun Street N Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/31/2026
Listed
$1,395,000
3.33%
MLS
5/12/2023
Sold
$1,350,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 185 Loudoun Street N

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,937
100%
$624,600
1%
2024
100%
$621,000
9%
2024
-100%
$570,200
—
2023
$6,044
5%
$570,200
15%
2022
$5,776
—
$497,900
—
2021
$5,776
—
$497,900
—
2020
$5,776
—
$497,900
—
2018
$5,776
2%
$497,900
—
2018
$5,676
-5%
$497,900
—
2016
$5,968
—
$497,900
-5%
2016
$5,968
—
$523,500
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 185 Loudoun Street N

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Coldwell Banker Premier, Gillian Joy Greenfield

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185 Loudoun Street N, Winchester, VA 22601 (MLS# VAWI2011270) is a Commercial Service property. 185 Loudoun Street N is currently listed for $1,395,000 and was received on July 31, 2026. Want to learn more about 185 Loudoun Street N? Do you have questions about finding other Commercial Service real estate for sale in Winchester? You can browse all Winchester real estate or contact a Coldwell Banker agent to request more information.

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