Winchester, VA Homes

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  /44

  Est $317,980

  Not Listed For Sale

  412 Fawn Dr, Winchester, VA 22602

  • 3 Beds
  • 2.5 Baths
  • 1,285 Sq Ft
  • Built 2009

  412 Fawn Dr, Winchester, VA 22602

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Jodi Costello ERA Oakcrest Realty, Inc.
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  /59

  $839,900

  Under Contract

  • 4 Beds
  • 4.5 Baths
  • 4,059 Sq Ft

  160 Wilton Dr, Winchester, VA 22603

  Welcome to this Beautiful 4 bedroom, 4.5 Bath All Brick Home where traditional character and modern charm meet together all nestled on a Picturesque 4.18-Acre Estate in the Highly Desirable Apple Pie Ridge Area. Experience the perfect blend of peaceful living and everyday convenience in this spacious All Brick home located just minutes from Schools, Valley Health Hospital, Shopping and all your

  Nancy Shiley Samson Properties

  160 Wilton Dr, Winchester, VA 22603
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  /87

  $578,000

  Sold Nov 18, 2025

  107 Roszel Rd, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 3,232 Sq Ft
  • Built 1960

  Last Sold Summary

  • $179/SF
  • 59 Days On Market

  Current Estimated Value $627,244

  Last Listing Agent John Scully Colony Realty

  107 Roszel Rd, Winchester, VA 22601
• 

  

  

  /34

  Est $541,942

  Not Listed For Sale

  104 Arthur Ln, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 3,310 Sq Ft
  • Built 2008

  104 Arthur Ln, Winchester, VA 22602

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Waleed Abuzar RE/MAX Galaxy
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  /15

  $375,990

  New Construction $16K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,752 Sq Ft

  105 Heirloom Way, Winchester, VA 22603

  This stunning two-level villa boasts a modern open concept design that seamlessly connects living spaces for an inviting and spacious feel. The main level features a living room that opens effortlessly to the dining area, creating a perfect space for entertaining and family gatherings. The expansive rear kitchen includes an L-shaped layout with an eating bar and an island with additional bar

  Brookfield Residential Builder

  105 Heirloom Way, Winchester, VA 22603
• 

  

  /30

  $280,000

  Sold Jun 12, 2026

  704 Watson Ave, Winchester, VA 22601

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2003

  Last Sold Summary

  • 5% Below List Price
  • $324/SF
  • 39 Days On Market

  Current Estimated Value $279,313

  Last Listing Agent Carlos Soares Samson Properties

  704 Watson Ave, Winchester, VA 22601
• 

  

  /27

  Est $347,335

  Not Listed For Sale

  113 Monticello Square, Winchester, VA 22602

  • 3 Beds
  • 4 Baths
  • 1,740 Sq Ft
  • Built 2009

  113 Monticello Square, Winchester, VA 22602

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Angie Ordonez NextHome Realty Select
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  /14

  $509,990

  New Construction Open Sat 12PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 2,216 Sq Ft

  101 Seminole Dr, Winchester, VA 22602

  The Glendale is a 2,216 square foot corner homesite, open concept two-story home with a finished basement that offers four bedrooms, three and a half bathrooms with a two-car garage. You will immediately feel at home as you enter the foyer and make your way into the spacious family room. This living space flows nicely into the eat-in kitchen with plenty of cabinets and island overlooking the

  D.R. Horton Builder

  101 Seminole Dr, Winchester, VA 22602
• 

  

  /39

  $409,990

  Sold May 18, 2026

  1813 Harvest Dr, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 1,920 Sq Ft
  • Built 2025

  Last Sold Summary

  • 9% Below List Price
  • $214/SF
  • 58 Days On Market

  Last Listing Agent Victoria Clark D R Horton Realty of Virginia LLC

  1813 Harvest Dr, Winchester, VA 22601
• 

  

  /28

  Est $345,754

  Not Listed For Sale

  109 Monticello Square, Winchester, VA 22602

  • 3 Beds
  • 4 Baths
  • 1,780 Sq Ft
  • Built 2009

  109 Monticello Square, Winchester, VA 22602

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Katie Deskins Century 21 Redwood Realty
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  /22

  $550,000

  Under Contract

  • Land
  • 3.69 Acres
  • $149,051 per Acre

  353 Greenwood Rd, Winchester, VA 22602

  Raw land totaling 3.69 acres zoned R-P in a great location right off Route 7 at the intersection of Greenwood Road and Valley Mill. Great opportunity with the possibility to build a home or even multiple townhouses!Survey attached to the listing.

  Amanda Magana RE/MAX Roots

  353 Greenwood Rd, Winchester, VA 22602
• 

  /2

  $60,000

  Sold Jul 27, 2026

  0 Winding Ridge Ln, Winchester, VA 22603

  • Land
  • 5 Acres
  • $12,000 per Acre

  Last Sold Summary

  • 41% Above List Price
  • 38 Days On Market

  Last Listing Agent Sheila Pack RE/MAX Roots

  0 Winding Ridge Ln, Winchester, VA 22603
• 

  

  /58

  Est $714,811

  Not Listed For Sale

  730 Old Baltimore Rd, Winchester, VA 22603

  • 4 Beds
  • 2.5 Baths
  • 3,912 Sq Ft
  • Built 2009

  730 Old Baltimore Rd, Winchester, VA 22603

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Cara Wilkins MarketPlace REALTY
• 

  

  /22

  $549,990

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,658 Sq Ft

  206 Williamson Rd, Winchester, VA 22602

  THIS IS A TO-BE-BUILT HOME THAT CAN BE BUILT ON ANY AVAILABLE HOMESITE. If the homesite shown is no longer available, we have other lots to choose from. The Avalon is a stunning 3‐bedroom, 2‐bath home offering up to 2,538 square feet of thoughtfully designed living space. This single‐family layout emphasizes main‐level living with an open floor plan that brings together a spacious great room, a

  Greta Fernandez New Home Star Virginia, LLC

  206 Williamson Rd, Winchester, VA 22602
• 

  /2

  $405,990

  Sold Mar 20, 2026

  137 Woodrow Rd, Winchester, VA 22602

  • 3 Beds
  • 2 Baths
  • 1,763 Sq Ft
  • Built 1997

  Last Sold Summary

  • $230/SF
  • 2 Days On Market

  Current Estimated Value $406,391

  Last Listing Agent Pamela Baber Coldwell Banker Premier

  137 Woodrow Rd, Winchester, VA 22602
• 

  

  /11

  Est $232,142

  Not Listed For Sale

  164 Brookland Ct Unit 11, Winchester, VA 22602

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Built 2002

  164 Brookland Ct Unit 11, Winchester, VA 22602

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Kevin Drake Coldwell Banker Premier
• 

  

  /50

  $799,000

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 3,256 Sq Ft

  201 Nathaniel Dr, Winchester, VA 22603

  Stunning new construction modern contemporary home situated on nearly 6 private wooded acres, offering the perfect balance of privacy and convenience. This thoughtfully designed home features an open-concept layout filled with abundant natural sunlight and beautiful wooded views throughout.The main living area showcases engineered hardwood flooring, a spacious living room and dining area, and

  Renee Waymire Samson Properties

  201 Nathaniel Dr, Winchester, VA 22603
• 

  

  /38

  $510,000

  Sold Jun 12, 2026

  121 Van Gogh Terrace, Winchester, VA 22602

  • 4 Beds
  • 2.5 Baths
  • 3,104 Sq Ft
  • Built 2005

  Last Sold Summary

  • 2% Above List Price
  • $164/SF
  • 4 Days On Market

  Current Estimated Value $515,684

  Last Listing Agent Kaitlyn Behr Samson Properties

  121 Van Gogh Terrace, Winchester, VA 22602
• 

  

  /26

  Est $241,285

  Not Listed For Sale

  164 Brookland Ct Unit 10, Winchester, VA 22602

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Built 2003

  164 Brookland Ct Unit 10, Winchester, VA 22602

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Stephanie Ryall Realty ONE Group Old Towne
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  /7

  $499,000

  • Land
  • 17.98 Acres
  • $27,753 per Acre

  Lot 13 Tavistock Dr, Winchester, VA 22602

  Beautiful 17.98 acre Lot, approved for 3 bedroom perk, Tavistock Estates, one of the last lots remaining! A gorgeous 7 minute drive from town through farmland and full of mountain views. Excellent neighborhood, road access is great, level lot among 'horse country' estates! Build your dream mini equestrian farm or just enjoy peace, quiet, and serenity with the genius of a quick commute into town!

  Gillian Greenfield Coldwell Banker Premier

  Lot 13 Tavistock Dr, Winchester, VA 22602

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