Winchester County, VA Homes

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  /17

  $349,990

  New Construction $40K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,784 Sq Ft

  TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601

  ***OFFERING UP TO $7K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*Featuring Bedford II in Valor Crossing! Open concept kitchen located next to the country kitchen and living room. Optional features include box bay rear window and 10' x 14' deck. Primary suite with large

  Brittany Newman DRB Group Realty, LLC

  TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601
• 

  

  

  /32

  $400,000

  Sold Sep 02, 2025

  423 Crescent Dr, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,548 Sq Ft
  • Built 1998

  Last Sold Summary

  • $258/SF
  • 4 Days On Market

  Current Estimated Value $395,236

  Last Listing Agent Sharon Farinholt Realty ONE Group Old Towne

  423 Crescent Dr, Winchester, VA 22601
• 

  

  

  /54

  Est $658,551

  Not Listed For Sale

  2513 Stoneridge Rd, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 3,297 Sq Ft
  • Built 2005

  2513 Stoneridge Rd, Winchester, VA 22601

  Last Sold Summary
• 

  

  

  /83

  $559,900

  • 2 Beds
  • 2.5 Baths
  • 2,031 Sq Ft

  411-U105 N Loudoun St Unit 105, Winchester, VA 22601

  Experience a rare opportunity to own a piece of Winchester history at The Fort, one of Old Town's most distinctive residential communities. Located just blocks from the vibrant Walking Mall, this beautifully renovated 2-bedroom, 2.5-bath condominium seamlessly blends historic character with modern luxury. Unit 105 features an open-concept floor plan with soaring ceilings, rich architectural

  Jen Richards MarketPlace REALTY

  411-U105 N Loudoun St Unit 105, Winchester, VA 22601
• 

  

  

  /60

  $405,000

  Sold Mar 30, 2026

  139 Biscane Ct, Winchester, VA 22602

  • 3 Beds
  • 3.5 Baths
  • 2,250 Sq Ft
  • Built 2018

  Last Sold Summary

  • 4% Below List Price
  • $180/SF
  • 28 Days On Market

  Current Estimated Value $406,179

  Last Listing Agent Roberto Cardoza Orellana Pearson Smith Realty, LLC

  139 Biscane Ct, Winchester, VA 22602
• 

  

  /90

  Est $680,826

  Not Listed For Sale

  953 Meadow Ct, Winchester, VA 22601

  • 4 Beds
  • 4.5 Baths
  • 4,042 Sq Ft
  • Built 2005

  953 Meadow Ct, Winchester, VA 22601

  Last Sold Summary

  • 6 Days On Market
• 

  

  /46

  $359,999

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  307 1/2 E Piccadilly St, Winchester, VA 22601

  Welcome to 307 1/2 E Piccadilly Street, a charming detached home offering comfort, convenience, and character in the heart of Winchester. Ideally located just minutes from Old Town Winchester, the Walking Mall, local restaurants, shopping, parks, and commuter routes, this property places you close to downtown amenities while still offering the privacy and feel of a standalone home. Inside, you’ll

  Nate Crandell HoneyWay

  307 1/2 E Piccadilly St, Winchester, VA 22601
• 

  

  /28

  $320,000

  Sold Sep 25, 2025

  230 Allison Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,376 Sq Ft
  • Built 1962

  Last Sold Summary

  • $233/SF
  • 87 Days On Market

  Current Estimated Value $315,592

  Last Listing Agent Jon Fleming Weichert Realtors - Blue Ribbon

  230 Allison Ave, Winchester, VA 22601
• 

  

  /72

  Est $660,976

  Not Listed For Sale

  938 Meadow Ct, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 4,336 Sq Ft
  • Built 2004

  938 Meadow Ct, Winchester, VA 22601

  Last Sold Summary
• 

  

  /6

  $4,500,000

  Under Contract

  • Land
  • 11.43 Acres
  • $393,701 per Acre

  801 Fairmont Ave, Winchester, VA 22601

  Unprecedented Development Opportunity, City of Winchester, 10.34 acres plus 3 SFH fronting Fairmont Ave (additional 1.09 acres). Gateway to downtown Old Town Winchester. Prime location for high density multifamily and mixed use commercial. Public utilities to site. Truly a catalyst development opportunity, located in the fast growing metropolitan area in Virginia. Voted #1 Main Street and Places

  Gillian Greenfield Coldwell Banker Premier

  801 Fairmont Ave, Winchester, VA 22601
• 

  

  /27

  $333,000

  Sold Sep 10, 2025

  509 W Cork St, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft
  • Built 1955

  Last Sold Summary

  • $325/SF
  • 78 Days On Market

  Current Estimated Value $323,139

  Last Listing Agent Dan Whitacre Colony Realty

  509 W Cork St, Winchester, VA 22601
• 

  

  /62

  Est $670,912

  Not Listed For Sale

  2304 Stoneridge Rd, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 3,419 Sq Ft
  • Built 2006

  2304 Stoneridge Rd, Winchester, VA 22601

  Last Sold Summary

  • 4 Days On Market
• 

  

  /29

  $259,900

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  1125 Conway St, Winchester, VA 22601

  Check out this Very Cute Bungalow in Winchester City! It has a Brand NEW Roof, Freshly Painted throughout, NEW kitchen/hall/bath flooring, NEW Stainless Steel Refrigerator, Restored deck, and Lovely Hardwood! Cozy with 2 Bedrooms and 1 Bath. Surely to be perfect for the first time Home Buyer! Great Location close to shopping & restaurants. Great for commuters as well as it's on the East side of

  Jodi Costello ERA Oakcrest Realty, Inc.

  1125 Conway St, Winchester, VA 22601
• 

  /2

  $925,000

  Sold Jan 16, 2026

  413 N Braddock St, Winchester, VA 22601

  • 5 Beds
  • 3 Baths
  • 2,782 Sq Ft
  • Built 1920

  Last Sold Summary

  • $332/SF

  Current Estimated Value $873,867

  Last Listing Agent Dan Whitacre Colony Realty

  413 N Braddock St, Winchester, VA 22601
• 

  

  /48

  Est $701,923

  Not Listed For Sale

  2329 Stoneridge Rd, Winchester, VA 22601

  • 5 Beds
  • 3.5 Baths
  • 4,529 Sq Ft
  • Built 2005

  2329 Stoneridge Rd, Winchester, VA 22601

  Last Sold Summary

  • 3 Days On Market
• 

  

  /41

  $374,000

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,809 Sq Ft

  328 Longview Ave, Winchester, VA 22601

  Highly motivated seller; priced reduced 15K. Welcome to this meticulously maintained, move-in-ready ranch home located within Winchester City limits. Perfectly situated on a premium, near-half-acre lot (.46 acres) off Papermill Road, this property offers the ultimate blend of city convenience and peaceful privacy with no backyard neighbors. Borders Buffalo Lick Run. Beautiful hardwood floors.

  Kelly Bauer Coldwell Banker Premier

  328 Longview Ave, Winchester, VA 22601
• 

  

  /36

  $419,990

  Sold Nov 19, 2025

  1810 Blythe Way, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $222/SF
  • 12 Days On Market

  D.R. Horton Abrams Crossing at Meadow Branch

  1810 Blythe Way, Winchester, VA 22601
• 

  

  /23

  Est $632,911

  Not Listed For Sale

  2313 Stoneridge Rd, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,921 Sq Ft
  • Built 2005

  2313 Stoneridge Rd, Winchester, VA 22601

  Last Sold Summary

  • 18 Days On Market
• 

  

  /23

  $275,000

  Under Contract

  • 2 Beds
  • 1 Bath
  • 1,472 Sq Ft

  323 Fairview Ave, Winchester, VA 22601

  Welcome home to this beautifully updated 2-bedroom, 1-bath single-family residence offering charm, comfort, and modern upgrades throughout. From the inviting front porch to the spacious fenced backyard, this move-in ready home combines classic character with thoughtful renovations. Inside, you’ll find brand new LVP flooring on both levels and a completely renovated kitchen featuring ceramic tile

  Jeremy Browne EXP Realty, LLC

  323 Fairview Ave, Winchester, VA 22601
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  /14

  $364,990

  Sold Oct 17, 2025

  627 Laurelwood Cir, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,442 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $253/SF
  • 31 Days On Market

  627 Laurelwood Cir, Winchester, VA 22601
• 

  

  /61

  Est $681,556

  Not Listed For Sale

  2624 Windwood Dr, Winchester, VA 22601

  • 6 Beds
  • 3.5 Baths
  • 4,768 Sq Ft
  • Built 2002

  2624 Windwood Dr, Winchester, VA 22601

  Last Sold Summary

  • 48 Days On Market
• 

  

  /8

  $689,000

  • 4 Beds
  • 2.5 Baths
  • 3,108 Sq Ft

  1950 Melvor Ln, Winchester, VA 22601

  Step into this meticulously maintained colonial home, a testament to quality craftsmanship and thoughtful design by Richmond American Homes. Situated in the desirable Meadow Branch South neighborhood, this residence offers an exceptional living experience with a perfect balance of formal and casual spaces This home is situated in a vibrant community with easy access to major roads, shopping, and

  Kim Kroner Washington Dulles Real Estate Group

  1950 Melvor Ln, Winchester, VA 22601
• 

  

  /14

  $312,000

  Sold Sep 05, 2025

  10 Richards Ave, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,704 Sq Ft
  • Built 1940

  Last Sold Summary

  • $183/SF
  • 65 Days On Market

  Current Estimated Value $308,631

  Last Listing Agent Lindsey Richardson ERA Oakcrest Realty, Inc.

  10 Richards Ave, Winchester, VA 22601
• 

  

  /51

  Est $564,942

  Not Listed For Sale

  2628 Windwood Dr, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,919 Sq Ft
  • Built 1996

  2628 Windwood Dr, Winchester, VA 22601

  Last Sold Summary

  • 8 Days On Market
• 

  

  /22

  $319,950

  $180K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,310 Sq Ft

  593 N Kent St, Winchester, VA 22601

  This charming home, a short walk from historic Winchester, underwent a complete studs up renovation a few years ago. With all new insulation, roof, energy efficient double pane windows, and updated systems, it offers efficiency and ease. The open floor plan flows into a kitchen with a dedicated pantry closet. Three appropriately sized bedrooms include a master with its own bath. Plus, enjoy

  Lawrence Lessin Homes By Owner, Inc.

  593 N Kent St, Winchester, VA 22601
• 

  

  /51

  $431,000

  Sold May 29, 2026

  202 Russelcroft Rd, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Built 1996

  Last Sold Summary

  • 1% Above List Price
  • $239/SF
  • 5 Days On Market

  Current Estimated Value $419,023

  Last Listing Agent Laura White ERA Oakcrest Realty, Inc.

  202 Russelcroft Rd, Winchester, VA 22601
• 

  

  /38

  Est $443,740

  Not Listed For Sale

  2535 Middle Rd, Winchester, VA 22601

  • 4 Beds
  • 2 Baths
  • 1,836 Sq Ft
  • Built 1987

  2535 Middle Rd, Winchester, VA 22601

  Last Sold Summary

  • 20 Days On Market
• 

  

  /52

  $459,900

  • 4 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  620 Crystal Ct, Winchester, VA 22601

  Rare Cul-de-Sac Gem in the Heart of Winchester! Now priced nearly to sell by motivated seller. Discover the perfect blend of tranquility and city convenience at 620 Crystal Court. Situated in a sought-after, quiet cul-de-sac right in the center of Winchester, this stunning 4-bedroom, 2.5-bathroom residence has been thoughtfully updated and is ready for you to call home. Main Level Elegance &

  VAIBHAV AGARWAL Realty FC, LLC

  620 Crystal Ct, Winchester, VA 22601
• 

  

  /27

  $325,000

  Sold Jul 25, 2025

  412 Fairview Ave, Winchester, VA 22601

  • 3 Beds
  • 3 Baths
  • 1,900 Sq Ft
  • Built 1964

  Last Sold Summary

  • $171/SF
  • 3 Days On Market

  Current Estimated Value $314,158

  Last Listing Agent Junue Hernandez Rojas Long & Foster Real Estate, Inc.

  412 Fairview Ave, Winchester, VA 22601
• 

  

  /59

  Est $393,406

  Not Listed For Sale

  2543 Middle Rd, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 1,585 Sq Ft
  • Built 1989

  2543 Middle Rd, Winchester, VA 22601

  Last Sold Summary

  • 45 Days On Market
• 

  

  /34

  $344,900

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,395 Sq Ft

  420 E Pall Mall St, Winchester, VA 22601

  "Beautifully Renovated On Pall Mall St." This 2-bedroom, 2-full bath ranch style home is ready for you to move right in! Home has been completely painted on the inside, and the outside brick/concrete, side handrails, outside/inside of doors have been freshly painted. The kitchen has new granite counters, new sink & faucet, new LVP flooring and new stainless-steel appliances. Huge family room with

  Matt Kilmer Samson Properties

  420 E Pall Mall St, Winchester, VA 22601
• 

  

  /17

  $329,000

  Sold Jun 08, 2026

  2952 Grace St, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1985

  Last Sold Summary

  • $343/SF
  • 5 Days On Market

  Current Estimated Value $318,681

  Last Listing Agent Carolina Mosquera Weichert, REALTORS

  2952 Grace St, Winchester, VA 22601
• 

  

  /44

  Est $504,523

  Not Listed For Sale

  2518 Windwood Dr, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,082 Sq Ft
  • Built 1990

  2518 Windwood Dr, Winchester, VA 22601

  Last Sold Summary

  • 0 Days On Market
• 

  

  /9

  $139,895

  Pending

  • 2 Beds
  • 1 Bath
  • 796 Sq Ft

  1124 Conway St, Winchester, VA 22601

  2 Level Rambler Featuring Spacious Bedrooms and a Functional Layout Perfect for Comfortable Living. Enjoy Quiet Mornings or Evening Relaxation on the Inviting Covered Front Porch, and Take Advantage of the Rear Deck for Outdoor Dining and Entertaining. The Property Also Includes a Walk Out Basement and Storage Shed Providing Extra Space For Tools, Equipment, or Seasonal Items. Situated on a

  Matthew Altizer ANR Realty, LLC

  1124 Conway St, Winchester, VA 22601
• 

  

  /50

  $450,000

  Sold Jun 26, 2025

  319 Walker St, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,309 Sq Ft
  • Built 1968

  Last Sold Summary

  • $195/SF
  • 14 Days On Market

  Current Estimated Value $468,258

  Last Listing Agent Tiffany Hunter ERA Oakcrest Realty, Inc.

  319 Walker St, Winchester, VA 22601
• 

  

  /33

  Est $501,713

  Not Listed For Sale

  621 Bittersweet Ct, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 1,976 Sq Ft
  • Built 1993

  621 Bittersweet Ct, Winchester, VA 22601

  Last Sold Summary

  • 3 Days On Market
• 

  

  /36

  $550,000

  Sold Jun 27, 2025

  212 Allison Ave, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 1,992 Sq Ft
  • Built 2025

  Last Sold Summary

  • $276/SF
  • 3 Days On Market

  Current Estimated Value $392,556

  Last Listing Agent Brittany Reyes Medrano Century 21 Redwood Realty

  212 Allison Ave, Winchester, VA 22601
• 

  

  /38

  Est $638,245

  Not Listed For Sale

  929 Meadow Ct, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 4,159 Sq Ft
  • Built 2005

  929 Meadow Ct, Winchester, VA 22601

  Last Sold Summary

  • 6 Days On Market
• 

  

  /26

  $374,990

  Sold Feb 11, 2026

  226 Monteith Dr, Winchester, VA 22601

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $210/SF
  • 25 Days On Market

  DRB Homes Village at Valor Crossing - Townhomes

  226 Monteith Dr, Winchester, VA 22601
• 

  

  /42

  Est $568,255

  Not Listed For Sale

  2025 Taylor Grace Ct, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 3,288 Sq Ft
  • Built 2008

  2025 Taylor Grace Ct, Winchester, VA 22601

  Last Sold Summary

  • 10 Days On Market

Showing Results 521 - 560, Page 14 of 18