• 114 days on site
  • 5 views

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.

Source: BRIGHT MLS, MLS#: VACL2006578

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  • Property Type
    Residential
  • Lot
    15.00 acres

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  • Median Age
    48
  • Population Density
    61
  • College Educated
    49%
  • Estimated Median Income
    $121,563
  • Estimated Total Home Owners
    945
  • Estimated Total Renters
    137
  • Owner / Renter Divide
    87% / 13%
  • Estimated Average Household Size
    3
  • Total Population
    2,865
  • Community data courtesy of LiveBy, Inc.

Owning this Home

$
$ %
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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

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Life at 1344 OLD WINCHESTER ROAD


Schools


School data courtesy of LiveBy, Inc.
Ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating. The schools displayed on this website are for informational purposes only and may not represent a complete or up-to-date list. School assignments are subject to change and should be verified directly with the local school district. Please contact the appropriate school district to confirm school zoning and enrollment eligibility for this property.

History

Date Event Value Agent
6/22/2026Source: BRIGHT MLS Status Change
ACTIVE UNDER CONTRACT
6/11/2026Source: BRIGHT MLS Price Reduction
$921,500 -2.9%
5/6/2026Source: BRIGHT MLS Price Reduction
$949,000 -3.1%
4/9/2026Source: BRIGHT MLS Price Reduction
$979,000 -1.0%
3/19/2026Source: BRIGHT MLS Status Change
ACTIVE
3/7/2026Source: BRIGHT MLS Added to Database
March 07, 2026
12/3/2024Source: BRIGHT MLS Added to Database
August 08, 2022
12/3/2024Source: BRIGHT MLS Added to Database
August 08, 2022
Listing provided courtesy of Compass- MLS# VACL2006578MLS ProviderContact Information: 7033106111

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