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Explore Similar Homes Within 10 Miles of Upperville, VA

  • /28

    $320,000 Open Sun 1PM - 3PM

    • 2 Beds
    • 2 Baths

    2091 Old Chapel Rd, Boyce, VA 22620

    This is nice little ranch house that sits on a level acre has so much to offer. Sit on the front porch and view the pasture and the mountains. Enjoy the flowers, and room to plant a garden. Come relax and enjoy peace and tranquility.

    Katherine Gregg CENTURY 21 New Millennium

    2091 Old Chapel Rd, Boyce, VA 22620
  • /74

    $3,999,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 7 Baths
    • 11,145 Sq Ft

    3252 Winchester Rd, Delaplane, VA 20144

    Introducing Ashleigh, a storied 98-acre estate with sweeping views of the Delaplane countryside. Originally part of Chief Justice John Marshall’s Oak Hill holdings, this Greek Revival manor was built for his granddaughter and remains one of Virginia’s most admired historic properties. Ashleigh is listed on both the National Register of Historic Places and the Virginia Landmarks Register, and is

    Carolyn Young Samson Properties

    3252 Winchester Rd, Delaplane, VA 20144
  • /69

    $325,000 Open House 5/24

    • 2 Beds
    • 1 Bath
    • 832 Sq Ft

    293 Old Sawmill Rd, Front Royal, VA 22630

    This beautifully renovated A-Frame with a loft is ready for your perfect summer getaway! Nestled in a peaceful, wooded, and private setting in the Blue Mountain area of Front Royal, this home offers a serene escape where you can unwind to the soothing sounds of the wind through the trees and nature’s chorus. Enjoy over 400 square feet of deck space, ideal for relaxing or entertaining. As part of

    Margaret Halseth Keller Williams Realty Dulles

    293 Old Sawmill Rd, Front Royal, VA 22630
  • /24

    $1,399,000 Open House 5/30

    • 4 Beds
    • 3.5 Baths
    • 4,313 Sq Ft

    18290 Turnberry Dr, Round Hill, VA 20141

    COMING to the market 5/28/2026- Interior photos coming soon! Set on 1.5 acres in the Stoneleigh community of Round Hill, this updated home sits along the third hole of the golf course, with western mountain views carried throughout much of the home. The property combines open sightlines, mature trees, and professionally maintained landscaping with a layout that flows comfortably from one space to

    Hanah Desherow Pearson Smith Realty, LLC

    18290 Turnberry Dr, Round Hill, VA 20141
  • /70

    $525,000 Open Sun 3PM - 5PM

    • 4 Beds
    • 2.5 Baths
    • 2,542 Sq Ft

    116 Roseville Ct, Boyce, VA 22620

    Welcome home to 116 Roseville Ct in the charming Roseville Downs neighborhood of Boyce, Virginia! This beautifully maintained 4-bedroom, 2.5-bath home offers over 2,500 square feet of comfortable living space, thoughtfully designed for both everyday living and entertaining. Freshly painted throughout with brand new flooring, carpet, and windows, truly move-in ready. The primary suite features a

    Vicky Mashaw Samson Properties

    116 Roseville Ct, Boyce, VA 22620
  • /32

    $629,900 Open House 5/21

    • 3 Beds
    • 2 Baths
    • 2,012 Sq Ft

    1904 John Mosby Hwy, Boyce, VA 22620

    Tucked away in the rolling countryside of Clarke County, this charming farmhouse retreat at 1904 John Mosby Highway offers a rare blend of privacy, space, and income potential. Set on 18+ picturesque acres, the property has been operating as a successful short-term rental on Airbnb and VRBO since September 2024, appealing to guests seeking a peaceful escape just minutes from Winchester and the

    Jen Richards MarketPlace REALTY

    1904 John Mosby Hwy, Boyce, VA 22620
  • /45

    $2,950,000 Open Sun 12PM - 2PM

    • 5 Beds
    • 5 Baths
    • 3,993 Sq Ft

    505 Martingale Ridge Dr, Middleburg, VA 20117

    Elegant Vineyard Hunt Box at the Residences at Salamander completed and ready for move-in on very-convenient-to-town Lot 19! Be among the first to own a thoughtfully designed Vineyard Hunt Box in the exclusive Residences at Salamander—a luxury community set adjacent to the Salamander Resort & Spa in the heart of Middleburgs iconic Wine and Hunt Country. This spec home begins construction in June

    Peter Pejacsevich Corcoran McEnearney

    505 Martingale Ridge Dr, Middleburg, VA 20117

Home Trends in Upperville, VA

Housing Trends

Median Sale Price
$1,225,000
Median Single Family Sale Price
$1,225,000
Average Price Per Sq Ft
$585
Number of Homes for Sale
2
Last 12 months Home Sales
11
Months of Supply
2.20
Median List Price
$1,225,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-6%
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