1344 Old Winchester Road
Description
Awaiting its next stewards, this picture-perfect vintage farmhouse is beautifully sited on 15.9 acres...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 15.9 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, the 1,732 sq ft home is warm and complete — original hardwood floors, custom built-ins, and a wood-burning fireplace create an inviting atmosphere that is immediately livable. 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 historic 60x40 two-story oak barn with electricity offers three stalls, a workshop, and a hay loft of extraordinary scale — a historical structure that defines the character of the entire property. A 40x100 metal equipment shed with concrete flooring provides serious working infrastructure. Additional outbuildings include 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 alongside a Virginia native flower garden and a dedicated cut flower 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.
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.
Listing Agent
Location
Sold By Corcoran McEnearney
Payment Calculator
$4,852 per month
30 year fixed, 6.71% Interest
$4,702
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1Property Information for 1344 Old Winchester Road
- Taxes: $1,792 / year
- MLS Type: Residential / Fee Simple
- County: Clarke County
- Tax ID Number: 21--A-83C
- Ownership: Fee Simple
- Condo Coop Association: No
- HOA: No
- Structure Type: Detached
- Style: Farmhouse/National Folk
- Levels/Stories: 2
- Waterfront: No
- Views: Mountain, Panoramic, Pasture, Scenic Vista
- Garage: No
- Expected On Market Date: 03-20-2026
- Subdivision: ROYSTON
- Subdivision: ROYSTON (CLARKE VA)
- Central Air: Yes
- Basement: Yes
- Above Grade Finished SQFT: 1,732.00
- Above Grade Fin SQFT Source: Estimated
- New Construction: No
- Property Condition: Very Good
- Stories: 2
- Year Built: 1910
- Lot Size: 15.00 AC / 653,400 SF
- 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: 1,732.00
- Total Finished SQFT Source: Estimated
- Total SQFT: 1,732.00
- 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 |
|---|---|---|---|
| Aug 6, 2026 | Closed BRIGHT #VACL2006578 | $910,000 | — |
| Jul 21, 2026 | Closed (Public Record) Public Record #144542468 | $910,000 | +3.1% / yr |
| Jun 22, 2026 | Pending BRIGHT #VACL2006578 | — | |
| Jun 22, 2026 | Active Under Contract BRIGHT #VACL2006578 | — | |
| Jun 11, 2026 | Price Change BRIGHT #VACL2006578 | $921,500 | — |
| May 6, 2026 | Price Change BRIGHT #VACL2006578 | $949,000 | — |
| 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 Williamsburg Multiple Listing Service #BMTVACL2000986 | $802,500 | — |
| Jun 24, 2022 | Closed BRIGHT #VACL2000986 | $802,500 | — |
| Jun 23, 2022 | Closed Williamsburg Multiple Listing Service #BMTVACL2000998 | $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 | — |
| 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 | Listed (Active) BRIGHT #VACL2000986 | $739,900 | — |
| May 12, 2022 | Closed BRIGHT #VACL2000850 | $225,000 | — |
| May 12, 2022 | Listed (Active) BRIGHT #VACL2000998 | $739,900 | — |
| May 9, 2022 | Listed (Active) Williamsburg Multiple Listing Service #BMTVACL2000998 | $739,900 | — |
| May 8, 2022 | Listed (Active) Williamsburg Multiple Listing Service #BMTVACL2000986 | $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 |
|---|---|---|
| 08/06/2026 | Closed BRIGHT #VACL2006578 | $910,000 |
| 07/21/2026 | Closed (Public Record) Public Record #144542468 | $910,000 +3.1% / yr |
| 06/22/2026 | Pending BRIGHT #VACL2006578 | — |
| 06/22/2026 | Active Under Contract BRIGHT #VACL2006578 | — |
| 06/11/2026 | Price Change BRIGHT #VACL2006578 | $921,500 |
| 05/06/2026 | Price Change BRIGHT #VACL2006578 | $949,000 |
| 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 Williamsburg Multiple Listing Service #BMTVACL2000986 | $802,500 |
| 06/24/2022 | Closed BRIGHT #VACL2000986 | $802,500 |
| 06/23/2022 | Closed Williamsburg Multiple Listing Service #BMTVACL2000998 | $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 |
| 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 | Listed (Active) BRIGHT #VACL2000986 | $739,900 |
| 05/12/2022 | Closed BRIGHT #VACL2000850 | $225,000 |
| 05/12/2022 | Listed (Active) BRIGHT #VACL2000998 | $739,900 |
| 05/09/2022 | Listed (Active) Williamsburg Multiple Listing Service #BMTVACL2000998 | $739,900 |
| 05/08/2022 | Listed (Active) Williamsburg Multiple Listing Service #BMTVACL2000986 | $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, we 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 any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. 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 08/06/2026 06:36 PM