Upperville, VA Homes

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  $11,200,000

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

  1610 Delaplane Grade Rd, Upperville, VA 20184

  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 added 21 rooms creating an ornate and classic Jeffersonian

  Susan Hensley Hunt Country Sotheby's International Realty

  1610 Delaplane Grade Rd, Upperville, VA 20184
• Explore Upperville

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  /21

  $2,750 per month

  • 3 Beds
  • 2 Baths
  • 1,982 Sq Ft
  • House for Rent

  1079 Greystone Rd, Upperville, VA 20184

  This charming three bedroom, two bath cottage is ideally located on a private estate in Upperville. A long, picturesque driveway leads to this secluded and private property. The historic villages of Upperville and Middleburg are just minutes away. The breathtaking views of the magnificent Blue Ridge Mountains serve as a backdrop and create a simply magical setting. The property features hardwood

  James Mcgowan Thomas and Talbot Estate Properties, Inc.

  1079 Greystone Rd, Upperville, VA 20184
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  $1,300,000 Sold Apr 21, 2025

  1154 Crofton Ln, Upperville, VA 20184

  • 3 Beds
  • 3.5 Baths
  • 2,462 Sq Ft
  • Built 2022

  Last Sold Summary

  • $528/SF
  • 21 Days On Market

  Current Estimated Value $1,304,030

  Last Listing Agent Kevin Chung Corcoran McEnearney

  1154 Crofton Ln, Upperville, VA 20184
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  /2

  Est $1,449,592 Not Listed For Sale

  8263 Oak Spring Rd, Upperville, VA 20184

  • 3 Beds
  • Built 2002

  8263 Oak Spring Rd, Upperville, VA 20184

  Last Sold Summary

  • 24% Above List Price
  • $540/SF
  • 0 Days On Market

  Last Sold Price $1,900,206

  Last Listing Agent John Coles Thomas and Talbot Estate Properties, Inc.
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  /50

  $19,800,000 Pending

  • 11 Beds
  • 13 Baths
  • 17,000 Sq Ft

  21846 Trappe Rd, Upperville, VA 20184

  Set amid the picturesque countryside of Upperville, Virginia, Ayrshire Farm rises from the landscape with a presence that feels both timeless and stately. Encompassing 571 acres in the heart of the Virginia Piedmont, the estate is rich in heritage, design, and purposeful land stewardship. Few properties in the region balance these elements with such ease or at this scale. The manor house,

  Daniel Heider TTR Sotheby's International Realty

  21846 Trappe Rd, Upperville, VA 20184
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  /2

  $6,500,000 Sold Nov 12, 2025

  21281 Belle Grey Ln, Upperville, VA 20184

  • 3 Beds
  • 3 Baths
  • 3,303 Sq Ft
  • Built 2009

  Last Sold Summary

  • $1,968/SF
  • 47 Days On Market

  Current Estimated Value $6,456,817

  Last Listing Agent Patrick Saltz Saltz Realty, Inc.

  21281 Belle Grey Ln, Upperville, VA 20184
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  /30

  Est $585,014 Not Listed For Sale

  9148 Walnut St, Upperville, VA 20184

  • 3 Beds
  • 2 Baths
  • 1,365 Sq Ft
  • Built 1939

  9148 Walnut St, Upperville, VA 20184

  Last Sold Summary

  • 2% Above List Price
  • $421/SF
  • 63 Days On Market

  Last Sold Price $575,000

  Last Listing Agent Paul MacMahon Sheridan-MacMahon Ltd.
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  $2,725,000

  • 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 10 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 patent

  Will Driskill Thomas and Talbot Estate Properties, Inc.

  10157 John s Mosby Hwy, Upperville, VA 20184
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  $1,135,000 Sold Jan 14, 2026

  1170 Parker St, Upperville, VA 20184

  • 4 Beds
  • 2 Baths
  • 2,775 Sq Ft
  • Built 1973

  Last Sold Summary

  • $409/SF
  • 81 Days On Market

  Current Estimated Value $907,898

  Last Listing Agent Cricket Bedford Thomas and Talbot Estate Properties, Inc.

  1170 Parker St, Upperville, VA 20184
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  /50

  Est $1,832,947 Not Listed For Sale

  22128 Willisville Rd, Upperville, VA 20184

  • 4 Beds
  • 3.5 Baths
  • 4,129 Sq Ft
  • Built 1985

  22128 Willisville Rd, Upperville, VA 20184

  Last Sold Summary

  • 50% Above List Price
  • $295/SF
  • 7 Days On Market

  Last Sold Price $1,220,000

  Last Listing Agent Mary Ann McGowan Thomas and Talbot Estate Properties, Inc.
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  $892,000 Sold Oct 16, 2025

  9068 John s Mosby Hwy, Upperville, VA 20184

  • 3 Beds
  • 3 Baths
  • 2,165 Sq Ft
  • Built 1939

  Last Sold Summary

  • $412/SF
  • 85 Days On Market

  Current Estimated Value $885,559

  Last Listing Agent Cricket Bedford Thomas and Talbot Estate Properties, Inc.

  9068 John s Mosby Hwy, Upperville, VA 20184
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  Est $2,410,834 Not Listed For Sale

  20532 Trappe Rd, Upperville, VA 20184

  • 3 Beds
  • 3.5 Baths
  • 4,214 Sq Ft
  • Built 1740

  20532 Trappe Rd, Upperville, VA 20184

  Last Sold Summary

  • 7% Below List Price
  • $616/SF
  • 1 Day On Market

  Last Sold Price $2,595,000

  Last Listing Agent Cricket Bedford Thomas and Talbot Estate Properties, Inc.
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  $4,500,000 Sold Jun 25, 2025

  1388 Crenshaw Rd, Upperville, VA 20184

  • 5 Beds
  • 7 Baths
  • 7,225 Sq Ft
  • Built 1997

  Last Sold Summary

  • $623/SF
  • 8 Days On Market

  Current Estimated Value $4,470,000

  Last Listing Agent Laura Farrell TTR Sotheby's International Realty

  1388 Crenshaw Rd, Upperville, VA 20184
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  /60

  Est $6,668,171 Not Listed For Sale

  33846 Foxlease Ln, Upperville, VA 20184

  • 7 Beds
  • 8 Baths
  • 12,620 Sq Ft
  • Built 1950

  33846 Foxlease Ln, Upperville, VA 20184

  Last Sold Summary

  • 5% Below List Price
  • $555/SF
  • 296 Days On Market

  Last Sold Price $7,007,777

  Last Listing Agent Julia O’Regan Thomas and Talbot Estate Properties, Inc.
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  $900,000 Sold Jun 09, 2025

  9082 John s Mosby Hwy, Upperville, VA 20184

  • 3 Beds
  • 3 Baths
  • 2,938 Sq Ft
  • Built 1823

  Last Sold Summary

  • $306/SF
  • 80 Days On Market

  Current Estimated Value $948,586

  Last Listing Agent Will Driskill Thomas and Talbot Estate Properties, Inc.

  9082 John s Mosby Hwy, Upperville, VA 20184
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  /2

  Est $458,031 Not Listed For Sale

  9337 Brooks Cluster Cir, Upperville, VA 20184

  • 3 Beds
  • 2 Baths
  • 1,353 Sq Ft
  • Built 1984

  9337 Brooks Cluster Cir, Upperville, VA 20184

  Last Sold Summary

  • 48% Below List Price
  • $229/SF

  Last Sold Price $310,000

  Last Listing Agent Margaret Mullery Washington Fine Properties
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  $1,225,000 Sold Aug 11, 2025

  9050 Hogan Ln, Upperville, VA 20184

  • 4 Beds
  • 4.5 Baths
  • 3,587 Sq Ft
  • Built 1986

  Last Sold Summary

  • $342/SF
  • 111 Days On Market

  Current Estimated Value $1,220,510

  Last Listing Agent Heather Wells Real Broker, LLC

  9050 Hogan Ln, Upperville, VA 20184
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  /2

  Est $870,257 Not Listed For Sale

  1177 Parker St, Upperville, VA 20184

  • 3 Beds
  • 4 Baths
  • 3,454 Sq Ft
  • Built 1984

  1177 Parker St, Upperville, VA 20184

  Last Sold Summary

  • 1% Below List Price
  • $250/SF

  Last Sold Price $865,000

  Last Listing Agent Cricket Bedford Thomas and Talbot Estate Properties, Inc.
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  $21,350,000 Sold Jan 29, 2026

  21515 Trappe Rd, Upperville, VA 20184

  • 9 Beds
  • 11 Baths
  • 12,500 Sq Ft
  • Built 1795

  Last Sold Summary

  • 19% Below List Price
  • $1,708/SF
  • 524 Days On Market

  Current Estimated Value $15,290,878

  Last Listing Agent Alex Webel HALL AND HALL PARTNERS, LLP

  21515 Trappe Rd, Upperville, VA 20184
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  Est $680,449 Not Listed For Sale

  1179 Parker St, Upperville, VA 20184

  • 3 Beds
  • 2.5 Baths
  • 2,336 Sq Ft
  • Built 1969

  1179 Parker St, Upperville, VA 20184

  Last Sold Summary

  • 17% Above List Price
  • $248/SF
  • 153 Days On Market

  Last Sold Price $580,000

  Last Listing Agent Cricket Bedford Thomas and Talbot Estate Properties, Inc.
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  $2,495,000 Sold May 14, 2025

  21881 Willisville Rd, Upperville, VA 20184

  • 5 Beds
  • 6.5 Baths
  • 8,187 Sq Ft
  • Built 2023

  Last Sold Summary

  • $305/SF
  • 59 Days On Market

  Current Estimated Value $2,669,084

  Last Listing Agent Will Driskill Thomas and Talbot Estate Properties, Inc.

  21881 Willisville Rd, Upperville, VA 20184
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  /31

  Est $1,270,613 Not Listed For Sale

  1248 Delaplane Grade Rd, Upperville, VA 20184

  • 3 Beds
  • 2.5 Baths
  • 3,110 Sq Ft
  • Built 1984

  1248 Delaplane Grade Rd, Upperville, VA 20184

  Last Sold Summary

  • 5% Above List Price
  • $429/SF
  • 32 Days On Market

  Last Sold Price $1,335,000

  Last Listing Agent John Coles Thomas and Talbot Estate Properties, Inc.
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  /5

  $995,000 Sold Aug 04, 2025

  7521 John s Mosby Hwy, Upperville, VA 20184

  • 3 Beds
  • 2 Baths
  • 2,112 Sq Ft
  • Built 1983

  Last Sold Summary

  • $471/SF
  • 12 Days On Market

  Current Estimated Value $1,014,882

  Last Listing Agent Emily Ristau Thomas and Talbot Estate Properties, Inc.

  7521 John s Mosby Hwy, Upperville, VA 20184
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  Not Listed For Sale

  0 Crofton Ln Lot C, Upperville, VA 20184

  0 Crofton Ln Lot C, Upperville, VA 20184

  Last Sold Summary

  Last Sold Price $245,000

  Last Listing Agent Scott Buzzelli Atoka Properties | Middleburg Real Estate
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  /40

  $615,000 Sold Jun 30, 2025

  9259 John s Mosby Hwy, Upperville, VA 20184

  • 1 Bed
  • 1 Bath
  • 936 Sq Ft
  • Built 2021

  Last Sold Summary

  • $657/SF
  • 53 Days On Market

  Current Estimated Value $636,915

  Last Listing Agent John Denny Long & Foster Real Estate, Inc.

  9259 John s Mosby Hwy, Upperville, VA 20184
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  /2

  Not Listed For Sale

  0 Rokeby Unit VAFQ2010508, Upperville, VA 20184

  0 Rokeby Unit VAFQ2010508, Upperville, VA 20184

  Last Sold Summary

  Last Sold Price $425,000

  Last Listing Agent Helen MacMahon Sheridan-MacMahon Ltd.
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  $2,710,000 Sold Aug 11, 2025

  1129 Delaplane Grade Rd, Upperville, VA 20184

  • 5 Beds
  • 4.5 Baths
  • 5,856 Sq Ft
  • Built 1832

  Last Sold Summary

  • $463/SF
  • 25 Days On Market

  Current Estimated Value $2,636,415

  Last Listing Agent Kathryn Harrell Washington Fine Properties, LLC

  1129 Delaplane Grade Rd, Upperville, VA 20184
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  /2

  Est $540,787 Not Listed For Sale

  9211 Patrick St, Upperville, VA 20184

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Built 2023

  9211 Patrick St, Upperville, VA 20184

  Last Sold Summary

  • 9% Below List Price
  • $619/SF

  Last Sold Price $495,000

  Last Listing Agent Casey A Sutherland Rosemont Real Estate, LLC
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  /30

  Est $594,271 Not Listed For Sale

  9233 Patrick St, Upperville, VA 20184

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Built 2023

  9233 Patrick St, Upperville, VA 20184

  Last Sold Summary

  • 4% Above List Price
  • $712/SF

  Last Sold Price $570,000

  Last Listing Agent Will Driskill Thomas and Talbot Estate Properties, Inc.
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  /25

  Est $1,353,454 Not Listed For Sale

  1225 Dunvegan Dr, Upperville, VA 20184

  • 3 Beds
  • 3 Baths
  • 3,052 Sq Ft
  • Built 1997

  1225 Dunvegan Dr, Upperville, VA 20184

  Last Sold Summary

  • 5% Above List Price
  • $424/SF
  • 276 Days On Market

  Last Sold Price $1,295,000

  Last Listing Agent Cricket Bedford Thomas and Talbot Estate Properties, Inc.
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  /2

  Est $754,138 Not Listed For Sale

  10153 John s Mosby Hwy, Upperville, VA 20185

  • Studio

  10153 John s Mosby Hwy, Upperville, VA 20185

  Last Sold Summary

  • 14% Below List Price

  Last Sold Price $660,000

  Last Listing Agent Will Driskill Thomas and Talbot Estate Properties, Inc.
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  /2

  Est $1,383,712 Not Listed For Sale

  1143 Crofton Ln, Upperville, VA 20184

  • 6 Beds
  • 6 Baths
  • 6,000 Sq Ft
  • Built 2023

  1143 Crofton Ln, Upperville, VA 20184

  Last Sold Summary

  • 11% Below List Price
  • $208/SF

  Last Sold Price $1,248,000

  Last Listing Agent Scott Buzzelli Atoka Properties | Middleburg Real Estate
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  /2

  Not Listed For Sale

  9160 John s Mosby Hwy, Upperville, VA 20184

  • 1 Bed
  • 2 Baths
  • 2,152 Sq Ft
  • Built 1890

  9160 John s Mosby Hwy, Upperville, VA 20184

  Last Sold Summary

  • 10% Below List Price
  • $395/SF

  Last Sold Price $851,000

  Last Listing Agent Maria Eldredge Thomas and Talbot Estate Properties, Inc.
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  Est $969,220 Not Listed For Sale

  20551 Trappe Rd, Upperville, VA 20184

  • 3 Beds
  • 2 Baths
  • 1,459 Sq Ft
  • Built 1984

  20551 Trappe Rd, Upperville, VA 20184

  Last Sold Summary

  • 21% Above List Price
  • $548/SF
  • 307 Days On Market

  Last Sold Price $798,937

  Last Listing Agent Ron Cawthorne Century 21 Redwood Realty
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  Not Listed For Sale

  0 Welbourne, Upperville, VA 20184

  0 Welbourne, Upperville, VA 20184

  Last Sold Summary

  • 952 Days On Market

  Last Sold Price $925,000

  Last Listing Agent Paul MacMahon Sheridan-MacMahon Ltd.
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  /13

  Est $937,736 Not Listed For Sale

  22340 Willisville Rd, Upperville, VA 20184

  22340 Willisville Rd, Upperville, VA 20184

  Last Sold Summary

  • 53% Below List Price
  • 177 Days On Market

  Last Sold Price $2,000,000

  Last Listing Agent Kathryn Harrell Washington Fine Properties
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  /2

  Est $744,656 Not Listed For Sale

  9267 Patrick St, Upperville, VA 20184

  • 4 Beds
  • 3 Baths
  • 4,498 Sq Ft
  • Built 1971

  9267 Patrick St, Upperville, VA 20184

  Last Sold Summary

  • 45% Below List Price
  • $114/SF

  Last Sold Price $512,000

  Last Listing Agent Emily Ristau Thomas and Talbot Estate Properties, Inc.
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  Est $458,372 Not Listed For Sale

  34055 Welbourne Rd, Upperville, VA 20184

  • 4 Beds
  • 3 Baths
  • 1,894 Sq Ft
  • Built 1970

  34055 Welbourne Rd, Upperville, VA 20184

  Last Sold Summary

  • 22% Above List Price
  • $198/SF
  • 172 Days On Market

  Last Sold Price $375,000

  Last Listing Agent Joyce Santiago Century 21 Redwood Realty
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  /47

  Est $1,000,075 Not Listed For Sale

  22202 Trappe Rd, Upperville, VA 20184

  • 3 Beds
  • 2 Baths
  • 1,779 Sq Ft
  • Built 1889

  22202 Trappe Rd, Upperville, VA 20184

  Last Sold Summary

  • 54% Above List Price
  • $365/SF
  • 10 Days On Market

  Last Sold Price $650,000

  Last Listing Agent Gitte Long Redfin Corporation
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  /54

  Est $4,989,445 Not Listed For Sale

  21167 Trappe Rd, Upperville, VA 20184

  • 4 Beds
  • 6 Baths
  • 5,308 Sq Ft
  • Built 1986

  21167 Trappe Rd, Upperville, VA 20184

  Last Sold Summary

  • 37% Above List Price
  • $688/SF
  • 300 Days On Market

  Last Sold Price $3,650,000

  Last Listing Agent Peter Pejacsevich Atoka Properties | Middleburg Real Estate

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