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Awaiting its next stewards, this picture-perfect vintage farmhouse is beautifully sited on 15 acres in coveted...In real estate, it’s all about location. This isn’t just a location—it’s a high-cation. Opportunities like this are exceedingly rare: surrounded by large, protected parcels—many in conservation easement—in the heart of Hunt Country, under $1M, and an hour to Washington, D.C. This is the unicorn, offering a truly uncommon chance to embrace peaceful, abundant country living without compromise.
Awaiting its next stewards, this picture-perfect vintage farmhouse is beautifully sited on 15 acres in coveted Blue Ridge Hunt territory, where a constant breeze and soft eastern mountain views set the rhythm of daily life.
A winding half-mile drive sets the tone, leading to a storybook setting where historic charm meets modern ease. Inside, original hardwood floors, custom built-ins, and a wood-burning fireplace create a warm, inviting atmosphere. Three well-appointed bedrooms feature tailored storage, while a dedicated home office, laundry/mudroom with utility sink, and a private outdoor shower add thoughtful functionality. Every room is framed by picturesque views of the surrounding landscape.
Outdoors, the property is equally compelling. A two-story barn with electricity offers three stalls, a workshop, and ample space for hobbies or future expansion. Additional improvements include a large metal equipment shed, a smaller ruminant barn, and repurposed grain silos reimagined as charming chicken houses—blending practicality with a touch of whimsy.
During their time here, the current owners have thoughtfully shaped the land for both beauty and utility—clearing acreage for pasture, adding extensive fencing, and creating a productive vegetable garden. The groundwork is in place for small-scale animal husbandry and a true farm-to-table lifestyle. It’s a property that invites you to live off the land, surrounded by character and authenticity that typically commands a far higher price point.
For those looking to expand, the vision is already in place. Veritas Construction—renowned for their mastery of historic additions and timeless design—has created expansion plans for both the home and barn, seamlessly blending old and new. These plans convey with the property, offering a turnkey path to elevate the estate while preserving its original charm.
The dream of country living is already here—quiet, intentional, and deeply rooted in the land—yet thoughtfully prepared for its next chapter.
Ideally located just 6 miles to Berryville, 8 miles to Winchester, and just 20 minutes to Middleburg, this offering strikes a rare balance—peaceful, private, and beautifully connected. NO DRIVE INS PLEASE.
Property Details for 1344 Old Winchester Road
Property Details for 1344 Old Winchester Road
| Status | Active |
|---|---|
| MLS # | VACL2006578 |
| Days on Market | 36 |
| Taxes | $1,792 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Property Type | Single Family |
| MLS Type | Residential / Fee Simple |
| Year Built | 1910 |
| Lot Size | 15.00 AC / 653,400 SF |
| County | Clarke County |
| Buyer's Agent Compensation | 2.5% |
Location
Listing Courtesy of: .
Building Information for 1344 Old Winchester Road
Payment Calculator
$5,079 per month
30 year fixed, 6.46% Interest
$4,930
$149
$0
Property Information for 1344 Old Winchester Road
- In City Limits: No
- School District Name: CLARKE COUNTY PUBLIC SCHOOLS
- School District County ID: 121141013768
- County: CLARKE
- Water View: No
- Water Access: No
- Water Oriented: No
- Navigable Water: No
- Tidal Water: No
- Riparian Rights Y/N: No
- Property Manager Y/N: No
- Senior Community: No
- Tax Year: 2021
- Tax Assessed Value: $419,100
- Zoning: AOC
- Automatically Update Tax Values Y/N: Yes
- # Bedrooms Count Main Level: 0
- # Bathrooms Count Main Level: 0
- # Bathrooms Full Main Level: 0
- # Bathrooms Half Main Level: 0
- # Bedrooms Count All Upper Levels: 3
- # Bathrooms Count All Upper Levels: 1
- # Bathrooms Full All Upper Levels: 1
- # Bedrooms Count Upper Level: 3
- # Bathrooms Count Upper Level: 1
- # Bathrooms Full Upper Level: 1
- Room List: Bedroom 2, Bedroom 3, Kitchen, Den, Foyer, Bedroom 1, Laundry, Office, Bathroom 1
- Stories: Main, Upper 1
- Room Type: Den
- Room Level: Main
- Room Exists: Yes
- Room Features: Built-Ins, Fireplace - Wood Burning, Flooring - HardWood
- Room Type: Foyer
- Room Level: Main
- Room Exists: Yes
- Room Features: Flooring - HardWood
- Room Type: Kitchen
- Room Level: Main
- Room Exists: Yes
- Room Features: Dining Area, Kitchen - Eat-in
- Room Type: Office
- Room Level: Main
- Room Exists: Yes
- Room Features: Built-Ins, Flooring - HardWood
- Room Type: Laundry
- Room Level: Main
- Room Exists: Yes
- Room Type: Bedroom 1
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Flooring - HardWood
- Room Type: Bathroom 1
- Room Level: Upper 1
- Room Exists: Yes
- Room Type: Bedroom 2
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Flooring - HardWood
- Room Type: Bedroom 3
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Flooring - HardWood
- Total Finished SQFT: 1,028.00
- Total Finished SQFT Source: Estimated
- Total SQFT: 1,028.00
- Total SQFT Source: Estimated
- Main Entrance Orientation: Southeast
- Construction Materials: Stucco
- Roof: Metal
- Wall and Ceiling Types: Dry Wall, Paneled Walls
- Flooring Type: Hardwood, Tile/Brick
- Basement Type: Full, Outside Entrance, Unfinished
- RFactor Basement: 0
- Foundation Details: Block, Slab
- Room and Floor: Bedrooms-Upper Level 1-1, Bedrooms-Upper Level 1-2, Bedrooms-Upper Level 1-3, Bathrooms Full-Upper Level 1-1
- # Bathrooms Full: 1
- # Bathrooms Half: 0
- Other Structure: Barn, Barn/Stable, Other, Run-in Shed, Shed
- Lot Size Source: Estimated
- Lot Features: Open, Partly Wooded, Private, Sloping
- Road Surface Type: Gravel
- Road Responsibility: Private, Easement/Right of Way
- Fencing: Barbed Wire, Board
- Parcel ID: 17034416
- Additional Parcels: No
- Ground Rent Exists: No
- Type Of Parking: Driveway
- Parking Features: Circular Driveway
- Interior Features: Built-Ins, Combination Kitchen/Dining, Water Treat System, Window Treatments, Wood Floors
- Fireplace: Yes
- Fireplaces Count: 1
- Fireplace Features: Marble, Other, Wood
- Appliances: Dishwasher, Dryer, Oven/Range - Electric, Refrigerator, Washer
- Accessibility Features: None
- Security Features: Security System
- Window Features: Casement, Double Hung, Replacement, Vinyl Clad
- Laundry Type: Has Laundry, Main Floor
- Exterior Features: Outbuilding(s), Outside Shower
- Outdoor Living Structures: Porch(es)
- Pool: No Pool
- Horse: Yes
- Horse Amenities: Paddock, Stable(s)
- Utilities: Phone
- Heating: Yes
- Cooling Type: Central A/C
- Cooling Fuel: Electric
- Heating Type: Central, Forced Air, Heat Pump(s)
- Heating Fuel: Electric, Oil
- Hot Water: Electric
- Water Source: Well
- Sewer Septic: On Site Septic
- List Agent AOR: Dulles Area Association of REALTORS
Property History for 1344 Old Winchester Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Apr 9, 2026 | Price Change BRIGHT #VACL2006578 | $979,000 | — |
| Mar 20, 2026 | Listed (Active) BRIGHT #VACL2006578 | $989,000 | — |
| Mar 7, 2026 | Withdrawn BRIGHT #VACL2006154 | — | |
| Mar 7, 2026 | Temp Off Market BRIGHT #VACL2006154 | — | |
| Mar 7, 2026 | Listed (Active) BRIGHT #VACL2006154 | $989,000 | — |
| Jun 24, 2022 | Closed BRIGHT #VACL2000986 | $802,500 | — |
| Jun 23, 2022 | Closed BRIGHT #VACL2000998 | $802,500 | — |
| Jun 22, 2022 | Closed (Public Record) Public Record #1493015819 | $802,500 | — |
| Jun 22, 2022 | Closed (Public Record) Public Record #1493015819 | $802,500 | — |
| Jun 22, 2022 | Closed (Public Record) Public Record #1493015819 | $802,500 | +2.4% / yr |
| May 16, 2022 | Pending BRIGHT #VACL2000986 | — | |
| May 16, 2022 | Pending BRIGHT #VACL2000998 | — | |
| May 16, 2022 | Active Under Contract BRIGHT #VACL2000986 | — | |
| May 16, 2022 | Active Under Contract BRIGHT #VACL2000998 | — | |
| May 12, 2022 | Closed BRIGHT #VACL2000850 | $225,000 | — |
| May 12, 2022 | Listed (Active) BRIGHT #VACL2000998 | $739,900 | — |
| May 12, 2022 | Listed (Active) BRIGHT #VACL2000986 | $739,900 | — |
| Apr 4, 2022 | Pending BRIGHT #VACL2000850 | — | |
| Apr 4, 2022 | Active Under Contract BRIGHT #VACL2000850 | — | |
| Apr 4, 2022 | Listed (Active) BRIGHT #VACL2000850 | $225,000 | — |
| Apr 28, 2006 | Closed BRIGHT #VACL100542 | $544,000 | — |
| Apr 27, 2006 | Closed (Public Record) Public Record #1255860701 | $544,000 | — |
| Mar 21, 2006 | Pending BRIGHT #VACL100542 | — | |
| Mar 16, 2006 | Listed (Active) BRIGHT #VACL100542 | $547,000 | — |
| Mar 16, 2000 | Closed BRIGHT #VACL103748 | $250,000 | — |
| Mar 16, 2000 | Pending BRIGHT #VACL103748 | — | |
| Mar 16, 2000 | Listed (Active) BRIGHT #VACL103748 | $260,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 04/09/2026 | Price Change BRIGHT #VACL2006578 | $979,000 |
| 03/20/2026 | Listed (Active) BRIGHT #VACL2006578 | $989,000 |
| 03/07/2026 | Withdrawn BRIGHT #VACL2006154 | — |
| 03/07/2026 | Temp Off Market BRIGHT #VACL2006154 | — |
| 03/07/2026 | Listed (Active) BRIGHT #VACL2006154 | $989,000 |
| 06/24/2022 | Closed BRIGHT #VACL2000986 | $802,500 |
| 06/23/2022 | Closed BRIGHT #VACL2000998 | $802,500 |
| 06/22/2022 | Closed (Public Record) Public Record #1493015819 | $802,500 |
| 06/22/2022 | Closed (Public Record) Public Record #1493015819 | $802,500 |
| 06/22/2022 | Closed (Public Record) Public Record #1493015819 | $802,500 +2.4% / yr |
| 05/16/2022 | Pending BRIGHT #VACL2000986 | — |
| 05/16/2022 | Pending BRIGHT #VACL2000998 | — |
| 05/16/2022 | Active Under Contract BRIGHT #VACL2000986 | — |
| 05/16/2022 | Active Under Contract BRIGHT #VACL2000998 | — |
| 05/12/2022 | Closed BRIGHT #VACL2000850 | $225,000 |
| 05/12/2022 | Listed (Active) BRIGHT #VACL2000998 | $739,900 |
| 05/12/2022 | Listed (Active) BRIGHT #VACL2000986 | $739,900 |
| 04/04/2022 | Pending BRIGHT #VACL2000850 | — |
| 04/04/2022 | Active Under Contract BRIGHT #VACL2000850 | — |
| 04/04/2022 | Listed (Active) BRIGHT #VACL2000850 | $225,000 |
| 04/28/2006 | Closed BRIGHT #VACL100542 | $544,000 |
| 04/27/2006 | Closed (Public Record) Public Record #1255860701 | $544,000 |
| 03/21/2006 | Pending BRIGHT #VACL100542 | — |
| 03/16/2006 | Listed (Active) BRIGHT #VACL100542 | $547,000 |
| 03/16/2000 | Closed BRIGHT #VACL103748 | $250,000 |
| 03/16/2000 | Pending BRIGHT #VACL103748 | — |
| 03/16/2000 | Listed (Active) BRIGHT #VACL103748 | $260,000 |
For completeness, Compass often displays two records for one sale: the MLS record and the public record.
Public Records for 1344 Old Winchester Road
Schools near 1344 Old Winchester Road
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | K to 5 | |||
| Public - | 6 to 8 | |||
| Public - | 9 to 12 | |||
| Public - | PK to 5 |
Rating | School | Distance |
|---|---|---|
Boyce Elementary School PublicK to 5 | ||
Johnson-Williams Middle School Public6 to 8 | ||
Clarke County High School Public9 to 12 | ||
D G Cooley Elementary School PublicPK to 5 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.
© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 04/23/2026 11:23 AM


















































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