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Connie Byers
REALTOR®, Associate Broker
(804) 869-3314
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40325 Charles Town Pike, Hamilton, VA 20158

$1,475,000
  • 40325 Charles Town Pike, Hamilton, VA 20158 Main Photo

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ACTIVE Price Reduced by $400,000 on November 12th, 2026
MLS#VALO2119052
STATUSACTIVE PROPERTY TYPECommercial - SCHOOLLOUDOUN COUNTY PUBLIC SCHOOLS

Property Description

MAJOR PRICE IMPROVEMENT! Now priced to reflect its current permitted uses, this 3.5-acre Hamilton property offers exceptional versatility as a private weekend retreat or a short-term rental destination. Zoned Rural A-3, the estate overlooks a neighboring 20-acre horse farm. While commercial events are not currently approved, Loudoun County allows buyers to apply for a minor special exception, though approval is not guaranteed. Featuring four distinct structures, the property provides remarkable flexibility for living, hosting, and business opportunities. Occupy the fully updated main house as a primary residence while operating the guest cottage as a short-term rental, or utilize the campus as a multi-building retreat. The main house features a primary main-level bedroom with a luxurious en-suite bath, alongside an additional upper-level bedroom suite. The adjacent guest cottage includes one bedroom, one bathroom, a loft, and access to a fenced-in pool and hot tub in the rear. The red barn tasting room boasts two half baths and expansive open space for entertaining, seamlessly extending out to a 1,200-square-foot Trex deck and flat lawn. A separate converted garage, known as "The Jar," features a wine cellar, a lounge tailored for game days with seating for three TVs, and flexible upper-level space. Out front, a half-acre vineyard is ready for home winemaking enthusiasts. Extensively updated since 2020 with refreshed interiors, a new roof on the converted garage, and a metal roof on the tasting room, this turn-key property presents an outstanding value in Loudoun County. The property's additional structures set it apart. An expansive barn with a finished tasting room, a detached flex building, dual entrances, and parking for 50+ vehicles give the next owner room to live, work, entertain, and grow. Approximately half an acre remains under vine, a nod to the property's winery heritage and a distinctive feature of the grounds. Outdoor living is where the property shines: a 1,200 square foot deck, fire pit area, and multiple gathering spaces overlook the pastoral setting, creating an exceptional backdrop for everyday living and entertaining. Recent improvements include new septic systems, updated HVAC, solar lighting, and infrastructure upgrades throughout. Zoned A-3, the property falls within a district that accommodates a range of residential, agricultural, and rural business uses; buyers should verify intended uses with Loudoun County. Whether you are seeking a one-of-a-kind primary residence with built-in rental income or a private estate with room for your vision, this property offers lifestyle and flexibility that rarely come to market in one of Northern Virginia's most sought-after settings.

40325 Charles Town Pike | MLS# VALO2119052

This commercial property located at 40325 Charles Town Pike, Hamilton, VA 20158 is currently listed for sale with an asking price of $1,475,000. Charles Town Pike is located within the LOUDOUN COUNTY PUBLIC SCHOOLS school district. Search Hamilton real estate on www.conniebyers.com today.

Upcoming Open Houses

Open House Sunday November 15th, 11:00am - 1:00pm

Property Features

Property Type: Commercial -
Cooling: Central A/C
Fuel Type: Natural Gas
Heating: Forced Air
Lot Size: 3.46 Acres
Taxes: $10,299
Year Built: 1981

Feature Descriptions

Accessibility: Level Entry - Main
Days on Site: 197
Exterior: Wood Siding
Flooring: Wood
Location: Rural
Lot: Level, Premium, Private
Lot Dimensions: 3.46 Acre(S)
Sewer: On Site Septic
Total Garage/Parking Spaces: 50
Water: Private, Well

Local Schools

High School: LOUDOUN VALLEY
Middle School: BLUE RIDGE
Elementary School: KENNETH W. CULBERT
School District: LOUDOUN COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Redfin Corporation
Agency Phone: 7036656665

Shown By

Agent Name: Connie Byers
Agent Phone: (804) 869-3314
Agency Title: Joyner Fine Properties

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©Joyner Fine Properties - Seller will consider paying buyer agent compensation based upon the terms and conditions of any offer made. Said compensation to be negotiated in the purchase agreement. Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 11/12/2026. The listing information on this page last changed on 11/12/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 11/12/2026 8:09:28 AM EST) or CAAR MLS (last updated Thu 11/12/2026 7:55:09 AM EST) or CVRMLS (last updated Thu 11/12/2026 8:08:22 AM EST) or Bright MLS (last updated Thu 11/12/2026 7:53:04 AM EST). Real estate listings held by brokerage firms other than Joyner Fine Properties may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

©Joyner Fine Properties - Seller will consider paying buyer agent compensation based upon the terms and conditions of any offer made. Said compensation to be negotiated in the purchase agreement.

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Agency License Information: Joyner Fine Properties and its agents are licensed in the Commonwealth of Virginia.



Agent License Information:  Licensed in the Commonwealth of Virginia

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