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Upperville, VA Homes for Sale

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  • /76

    $2,595,000

    • 4 Beds
    • 4 Baths
    • 3,324 Sq Ft

    33195 Millville Rd, Upperville, VA 20184

    Small Spring Farm is being offered for the first time in over 50 years. Nestled on 27 scenic acres just north of Upperville, this charming horse property enjoys beautiful Blue Ridge Mountain views and offers a rare combination of history, character, and equine amenities in the heart of Virginia's hunt country. At the center of the farm is a unique residence created by linking two historic stone

    Agent Photo

    Cricket Bedford

    Thomas and Talbot Estate Properties, Inc.

    33195 Millville Rd, Upperville, VA 20184
  • /123

    $11,200,000

    • 4 Beds
    • 3.5 Baths
    • 8,613 Sq Ft

    1610 Delaplane Grade Rd, Upperville, VA 20184

    BACK ON THE MARKET DUE TO NO FAULT OF THE SELLER OR PROPERTY. Peace and Plenty at Bollingbrook, circa 1809, presents an outstanding property in the history of Virginia. Originally part of a 9,600-acre land patent from Lord Fairfax in 1731 it later became a wedding present of 790 acres in 1809 whereas the one-story, Federal brick house of four rooms was constructed. Later in 1830, Robert Bolling

    Susan Hensley Hunt Country Sotheby's International Realty

    1610 Delaplane Grade Rd, Upperville, VA 20184
  • /65

    $899,000

    • 3 Beds
    • 2 Baths
    • 2,384 Sq Ft

    1150 Poplar Row Ln, Upperville, VA 20184

    The simple pleasures of farmhouse living, in the heart of Upperville.There is something wonderfully comforting about an old farmhouse—the wide-plank feel of hardwood floors beneath your feet, rooms that feel connected rather than formal, sunlight moving through the windows, and the sense that generations have lived, gathered, cooked, and celebrated here. 1150 Poplar Row Lane captures that

    Jennette Taylor Keller Williams Realty

    1150 Poplar Row Ln, Upperville, VA 20184
  • /10

    $795,000

    • Land
    • 1.84 Acres
    • $432,065 per Acre

    0 Rokeby Unit VAFQ2024072, Upperville, VA 20184

    Discover a rare 1.9+/- acre parcel tucked away off prestigious Rokeby Road. This stunning piece of land is ready for someone to build their dream home. This parcel boasts gorgeous, panoramic views of the protected Virginia countryside and surrounding farms, perfectly positioned between historic Middleburg and Upperville.The current owners have thoughtfully improved the property with majestic

    Will Driskill Thomas and Talbot Estate Properties, Inc.

    0 Rokeby Unit VAFQ2024072, Upperville, VA 20184
  • /56

    $849,000

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,432 Sq Ft

    9027 John s Mosby Hwy, Upperville, VA 20184

    Nestled in the heart of historic Upperville, this charming farmhouse offers timeless character on a picturesque 1-acre lot. Featuring 3 bedrooms, 2.5 bathrooms, and over 2,400 square feet of living space, the home welcomes you with a classic covered front porch, metal roof, and mature landscaping.A standout feature is the CV (Commercial Village) zoning, presenting a unique opportunity for

    Peter Pejacsevich Corcoran McEnearney

    9027 John s Mosby Hwy, Upperville, VA 20184
  • /64

    $1,550,000

    Open Sat 12PM - 4PM Coming Soon Sep 23
    • 3 Beds
    • 2 Baths
    • 3,801 Sq Ft

    9016 John s Mosby Hwy, Upperville, VA 20184

    European-Inspired Architectural Gem in Virginia Horse Country!Just eight miles from Middleburg and approximately one hour from Washington, DC, this exceptional 3,800-square-foot residence is a rare architectural gem, blending European-inspired elegance, exceptional craftsmanship, and modern luxury in the heart of Virginia Horse Country.Ideally located along John S. Mosby Highway just off

    Ilhan Birgin Samson Properties

    9016 John s Mosby Hwy, Upperville, VA 20184
  • /80

    $2,575,000

    • 4 Beds
    • 2.5 Baths
    • 3,216 Sq Ft

    10157 John s Mosby Hwy, Upperville, VA 20184

    Welcome to Slate Hill, an exquisite country estate on almost 7+/- acres. Fully renovated interior and exterior in 2021 with all original features retained, including wide heart pine flooring throughout and detailed woodwork. This elegant c. 1700’s property has 4 bedrooms, 2.5 full baths and combines a wonderful mix of old and new. The property was originally a portion of the 2,000 acre land

    Will Driskill Thomas and Talbot Estate Properties, Inc.

    10157 John s Mosby Hwy, Upperville, VA 20184

Why Live in Upperville

In the heart of Virginia Hunt Country, Upperville is a historic village known for its equestrian heritage and time-honored country estates. Residents embrace the Hunt Country lifestyle year-round, particularly at the Upperville Colt & Horse Show, ...

Upperville, VA Home Prices

Upperville, VA
Median Home Price
$1,672,500
Median Sale Price
$1,505,000
+16% YoY
Avg. Price per Square Foot
$647
Median Single Family Price
$1,712,500
Total Active Listings
7 listings
Market Conditions
12 Months of Supply
Buyer's Market

Frequently Asked Questions

What is the average home price in Upperville, VA?
Homes for sale in Upperville, VA have an average home price of $4,194,900.
How many homes have sold over the last 12 months in Upperville, VA?
6 homes have sold in Upperville, VA over the last 12 months.
What is the average household income in Upperville, VA?
The average household income in Upperville, VA is $139K.
What are the most popular zip codes in Upperville, VA?
The most popular zip codes in Upperville, VA include 20184, 20144, 20130, 20115 and 20117.
How much do you need to make to afford a house in Upperville?
The median home price in Upperville is $1,672,500. If you put a 20% down payment of $334,500 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $8,290 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $355K a year to afford the median home price in Upperville. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Upperville is $139K.
How are the schools in Upperville, VA?
Upperville, VA has highly rated public and private schools. Some of the best schools in Upperville based on Niche Grades are Loudoun Valley High School, Blue Ridge Middle School and Banneker Elementary School. Browse all the schools in Upperville, VA to learn more.
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