Winchester County, VA Homes

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  $1,300,000

  • Land
  • 64.91 Acres
  • $20,028 per Acre

  Lot 7 Cedar Creek Grade, Winchester, VA

  Rare opportunity to own 64+ scenic acres on the desirable west side of Winchester, VA. This preservation parcel offers one building right and features a beautiful mix of open land and partial woodland, providing both usability and privacy. Formerly an apple orchard, the property is well suited for a small farm, specialty crops, or vineyard, with potential for additional uses with an approved

  

  Lori Bales

  Keller Williams Realty

  (540) 974-1542

  Lot 7 Cedar Creek Grade, Winchester, VA
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  $1,350 per month

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Townhouse for Rent

  233 Kern St, Winchester, VA 22601

  Downtown Winchester location, full of light and super cute! This 2 bed/1 bath duplex offers a private, fenced in backyard on the north side of town. Completely renovated in 2022. Available for immediate occupancy. Both sides of this duplex are ready to go! Bring a friend you want close, but not roommate close. LOLApplication fee $50 for everyone 18 or older, no pets, monthly income minimum of

  

  Anna Fox

  NextHome Realty Select

  (540) 299-2935

  233 Kern St, Winchester, VA 22601
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  $415,000 Sold May 08, 2025

  526 N Braddock St, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,375 Sq Ft
  • Built 1927

  Last Sold Summary

  • $175/SF
  • 5 Days On Market

  Current Estimated Value $436,413

  Last Listing Agent Leah Clowser RE/MAX Roots

  526 N Braddock St, Winchester, VA 22601
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  Not Listed For Sale

  640 Hemsworth Ln, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,916 Sq Ft
  • Built 2024

  640 Hemsworth Ln, Winchester, VA 22601

  Last Sold Summary

  • $205/SF
  • 23 Days On Market

  Last Sold Price $392,201

  Last Listing Agent Debbie Menzer Weichert Corporate
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  /65

  $389,990 Open Sat 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  317 Gray Ave, Winchester, VA 22601

  Welcome to 317 Gray Ave in Winchester, Virginia. This charming Colonial blends historic character with extensive modern updates, creating the perfect balance of vintage appeal and contemporary comfort. The home features 4 bedrooms, 2 full bathrooms, and 1 half bathroom, along with a recently finished attic that offers flexible additional living space. The primary suite includes a beautifully

  

  Matthew Abregu

  Keller Williams Realty

  (540) 701-3590

  317 Gray Ave, Winchester, VA 22601
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  $1,700 per month

  • 2 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • House for Rent

  228 Opequon Ave, Winchester, VA 22601

  coming soon- pictures will be up later today

  

  Frank Armstrong, IV

  Colony Realty

  (540) 766-5892

  228 Opequon Ave, Winchester, VA 22601
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  $630,000 Sold Jul 03, 2025

  716 S Washington St, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 2,774 Sq Ft
  • Built 1865

  Last Sold Summary

  • $227/SF
  • 28 Days On Market

  Current Estimated Value $624,057

  Last Listing Agent Lisa Alberti Pearson Smith Realty, LLC

  716 S Washington St, Winchester, VA 22601
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  Est $550,703 Not Listed For Sale

  2853 Packer St, Winchester, VA 22601

  • 5 Beds
  • 3.5 Baths
  • 3,284 Sq Ft
  • Built 2007

  2853 Packer St, Winchester, VA 22601

  Last Sold Summary

  • 5% Above List Price
  • $160/SF
  • 209 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Robert Adams Weichert Corporate
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  $549,900 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  435 Mikey Ct, Winchester, VA 22601

  Welcome to 435 Mikey Court, a beautifully appointed home tucked within the highly desirable Village at Harvest Ridge, a premier 55+ community offering comfort, quality, and ease of living. Designed for effortless main-level living, this home features a well-thought-out open floorplan that connects the living, dining, and kitchen spaces, creating a warm and inviting atmosphere with generous room

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 530-3150

  435 Mikey Ct, Winchester, VA 22601
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  $2,400 per month

  • 4 Beds
  • 3.5 Baths
  • 1,960 Sq Ft
  • Townhouse for Rent

  1801 Harvest Dr, Winchester, VA 22601

  Brand new and move-in ready, this attractive three-level end-unit townhome at 1801 Harvest Drive offers modern living in a fantastic Winchester location. Featuring a full brick front and additional sound insulation, this end unit provides both style and comfort. The entry level includes a one-car garage, a private bedroom, and a full bathroom, perfect for guests, a home office, or flexible living

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 619-5461

  1801 Harvest Dr, Winchester, VA 22601
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  $545,000 Sold Nov 07, 2025

  509 Marion St, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,691 Sq Ft
  • Built 1992

  Last Sold Summary

  • $203/SF
  • 3 Days On Market

  Current Estimated Value $550,897

  Last Listing Agent Mark Francis Real Broker LLC

  509 Marion St, Winchester, VA 22601
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  Est $347,564 Not Listed For Sale

  2943 S Pleasant Valley Rd, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,479 Sq Ft
  • Built 1962

  2943 S Pleasant Valley Rd, Winchester, VA 22601

  Last Sold Summary

  • 1% Above List Price
  • $232/SF
  • 14 Days On Market

  Last Sold Price $342,500

  Last Listing Agent Anna Fox NextHome Realty Select
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  $175,000

  • Land
  • 0.37 Acre
  • $472,973 per Acre

  719 Kennedy Dr, Winchester, VA 22601

  Vacant Lot in Rolling HillsOne of the last opportunities to own a vacant lot in the desirable Rolling Hills community. This property offers the perfect setting to build your new home or presents an excellent opportunity for a long-term investment. Enjoy a well-established neighborhood with limited remaining buildable lots. Buyer to verify zoning, utilities, and intended use. Water and Sewer

  

  Frank Armstrong, IV

  Colony Realty

  (540) 709-9357

  719 Kennedy Dr, Winchester, VA 22601
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  $1,500 per month

  • 2 Beds
  • 1 Bath
  • 3,150 Sq Ft
  • Townhouse for Rent

  121 Taft Ave, Winchester, VA 22601

  Charming 2-Bedroom Apartment – Prime Location Near Shenandoah University! This well-maintained 1-level apartment features 2 bedrooms and 1 full bathroom. Enjoy the convenience of a great location—just minutes from Shenandoah University, shopping, dining, and more! WASHER and Dryer in the unit!

  

  Frank Armstrong, IV

  Colony Realty

  (540) 755-3946

  121 Taft Ave, Winchester, VA 22601
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  $270,000 Sold Mar 20, 2026

  407 van Fossen St, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 954 Sq Ft
  • Built 1956

  Last Sold Summary

  • 4% Below List Price
  • $283/SF
  • 7 Days On Market

  Current Estimated Value $272,604

  Last Listing Agent Michele Gibson Samson Properties

  407 van Fossen St, Winchester, VA 22601
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  Est $547,558 Not Listed For Sale

  2721 Middle Rd, Winchester, VA 22601

  • 6 Beds
  • 3 Baths
  • 3,452 Sq Ft
  • Built 2002

  2721 Middle Rd, Winchester, VA 22601

  Last Sold Summary

  • 8% Above List Price
  • $147/SF
  • 90 Days On Market

  Last Sold Price $508,000

  Last Listing Agent Chad Lesman RE/MAX
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  $250,000 Coming Soon

  • 2 Beds
  • 1.5 Baths
  • 1,064 Sq Ft

  523 Monticello St, Winchester, VA 22601

  Sold "As-IS" Nice investment or starter property. Needs a little updating. Hardwoods throughout upstairs and living room downstairs. This price includes 525 Monticello lot. Tax ID #330-02-19. If any questions call listing agent. Agent related to seller.

  

  Ned Stock

  Berkshire Hathaway HomeServices PenFed Realty

  (540) 305-3611

  523 Monticello St, Winchester, VA 22601
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  $2,200 per month

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  21 S Stewart St Unit 4, Winchester, VA 22601

  Charming Remodeled 2-Bedroom Apartment Near Old Town Winchester!Enjoy the perfect mix of comfort and convenience in this beautifully remodeled 2 bedroom, 2 bathroom apartment located just steps from historic Old Town Winchester. This spacious unit features modern updates, in-unit laundry, and a fully fenced private yard—ideal for relaxing or entertaining. You'll also love the generous storage

  

  Frank Armstrong, IV

  Colony Realty

  (540) 318-1292

  21 S Stewart St Unit 4, Winchester, VA 22601
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  $335,200 Sold Jul 25, 2025

  128 Fox Dr, Winchester, VA 22601

  • 4 Beds
  • 3 Baths
  • 2,606 Sq Ft
  • Built 1961

  Last Sold Summary

  • $129/SF
  • 25 Days On Market

  Current Estimated Value $336,598

  Last Listing Agent MJ Frazier Serhant

  128 Fox Dr, Winchester, VA 22601
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  Est $380,879 Not Listed For Sale

  524 Hollingsworth Dr, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 992 Sq Ft
  • Built 1957

  524 Hollingsworth Dr, Winchester, VA 22601

  Last Sold Summary

  • 2% Below List Price
  • $390/SF
  • 2 Days On Market

  Last Sold Price $387,000

  Last Listing Agent Dalila Zamorano Samson Properties
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  /23

  $300,000

  • 3 Beds
  • 1 Bath
  • 1,134 Sq Ft

  27 Jackson Ave, Winchester, VA 22601

  Completely renovated and move-in ready, this charming 3 bedroom, 1 bath home is ideally located just minutes from downtown Winchester's shops, dining, and entertainment. Inside, you'll find beautiful hardwood floors throughout and a brand new kitchen and fully renovated bathroom. Major updates to the home include a new roof, new windows, new HVAC system, new hot water heater and new electric all

  

  Mikiala Whitacre

  ERA Oakcrest Realty, Inc.

  (540) 590-5591

  27 Jackson Ave, Winchester, VA 22601
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  $1,450 per month

  • 2 Beds
  • 2 Baths
  • 1,464 Sq Ft
  • House for Rent

  11 Taft Ave Unit 1, Winchester, VA 22601

  One of the largest 2-bedroom, 2-bathroom apartments in Winchester! This spacious ground-floor unit offers comfortable living in a convenient location close to shopping, restaurants, and Shenandoah University. The apartment features central air, washer and dryer hookups, and a generous layout with plenty of living space. Enjoy the added convenience of off-street parking and easy access to nearby

  

  Frank Armstrong, IV

  Colony Realty

  (540) 679-7819

  11 Taft Ave Unit 1, Winchester, VA 22601
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  $359,990 Sold Feb 17, 2026

  230 Monteith Dr, Winchester, VA 22601

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

  Move in Ready Sold Summary

  • $202/SF
  • 86 Days On Market

  DRB Homes Village at Valor Crossing - Townhomes

  230 Monteith Dr, Winchester, VA 22601
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  Est $566,409 Not Listed For Sale

  926 Wayne Dr, Winchester, VA 22601

  • 5 Beds
  • 3.5 Baths
  • 3,918 Sq Ft
  • Built 2003

  926 Wayne Dr, Winchester, VA 22601

  Last Sold Summary

  • 6% Above List Price
  • $137/SF
  • 138 Days On Market

  Last Sold Price $535,000

  Last Listing Agent Melissa Crider Sager Real Estate
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  $365,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft

  127 Shirley St, Winchester, VA 22601

  Comfortable living at this split-foyer home located in the heart of the City of Winchester. On the main level, you’ll find three bedrooms and a full bath. The lower level features a fourth bedroom plus a second full bath — ideal for guests, or a home office. Location is a standout. You’re just minutes from downtown dining, shopping, and community events, and enjoy easy access to schools, parks,

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 802-5087

  127 Shirley St, Winchester, VA 22601
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  $1,500 per month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  21 S Stewart St Unit 2, Winchester, VA 22601

  2 Bedroom Apartment for Rent – Downtown Winchester Great 2nd-floor apartment located in downtown Winchester with 2 bedrooms and 1 bathroom. This home is just a short walk from Old Town Winchester, giving you easy access to local restaurants, shops, and entertainment. The apartment features very spacious bedrooms, a comfortable family room, and a fully enclosed back porch, perfect for relaxing or

  

  Frank Armstrong, IV

  Colony Realty

  (540) 534-4239

  21 S Stewart St Unit 2, Winchester, VA 22601
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  $580,000 Sold Dec 09, 2025

  553 Bellview Ave, Winchester, VA 22601

  • 5 Beds
  • 2.5 Baths
  • 2,386 Sq Ft
  • Built 1978

  Last Sold Summary

  • $243/SF
  • 2 Days On Market

  Current Estimated Value $580,871

  Last Listing Agent Dan Whitacre Colony Realty

  553 Bellview Ave, Winchester, VA 22601
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  Not Listed For Sale

  315 Gray Ave, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,638 Sq Ft
  • Built 1931

  315 Gray Ave, Winchester, VA 22601

  Last Sold Summary

  • $236/SF
  • 1 Day On Market

  Last Sold Price $386,350

  Last Listing Agent Devon Fox Samson Properties
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  $295,000 Coming Soon

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  704 Watson Ave, Winchester, VA 22601

  Beautifully Maintained Bungalow in a Prime Location! This very well-kept home offers 2 bedrooms and 1 full bath on the main level, showcasing pride of ownership throughout. Ideally located just blocks from shopping, coffee shops, and all the conveniences the city has to offer, this property combines comfort with unbeatable accessibility. Enjoy a spacious eat-in kitchen with plenty of room for a

  

  Carlos Soares

  Samson Properties

  (540) 530-4023

  704 Watson Ave, Winchester, VA 22601
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  $1,700 - $3,900 per month

  The Local

  1 - 4 Beds

  230 Spring St, Winchester, VA 22601

  Modern designs, elegant finishes, and the most desirable amenities await you at the areas newest apartment home living destination, the Local. Our Winchester apartments come in one, two, three, and four-bedroom floorplans, each featuring spacious and adaptable layouts. Various interior extras adorn them including an open floorplan concept, walk-in closets, in-unit washers/dryers, and more. As a

  230 Spring St, Winchester, VA 22601
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  $497,000 Sold Aug 25, 2025

  903 Crestview Terrace, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 3,204 Sq Ft
  • Built 2006

  Last Sold Summary

  • $155/SF
  • 64 Days On Market

  Current Estimated Value $553,175

  Last Listing Agent MARIA STRIBLING CENTURY 21 New Millennium

  903 Crestview Terrace, Winchester, VA 22601
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  Est $428,548 Not Listed For Sale

  222 E Piccadilly St, Winchester, VA 22601

  • 3 Beds
  • 3.5 Baths
  • 2,052 Sq Ft
  • Built 2022

  222 E Piccadilly St, Winchester, VA 22601

  Last Sold Summary

  • 6% Above List Price
  • $197/SF
  • 595 Days On Market

  Last Sold Price $404,900

  Last Listing Agent Jason Aikens RE/MAX
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  $640,000 Under Contract

  • 6 Beds
  • 3.5 Baths
  • 3,192 Sq Ft

  162 Omps Dr, Winchester, VA 22601

  This exceptional residence is nestled in a popular neighborhood in Winchester, just moments from Winchester Medical Center. With almost 4,000 square feet of refined living space, this 6-bedroom, 3.5-bath home delivers the scale, comfort, and location today’s discerning buyer expects.Designed for both elegant entertaining and everyday ease, the home features expansive living areas filled with

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 274-1014

  162 Omps Dr, Winchester, VA 22601
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  $1,625 per month

  • 2 Beds
  • 1 Bath
  • 976 Sq Ft
  • Townhouse for Rent

  609 Smithfield Ave, Winchester, VA 22601

  For Lease – Available Immediately! Don’t miss this charming three-level end-unit townhouse, ideally located just minutes from downtown Winchester and Shenandoah University. Enjoy convenient access to shopping, dining, schools, recreational activities, and major commuter routes.This well-maintained home features two spacious bedrooms and one full bath, along with beautiful hardwood floors that

  Tracy Jewell Samson Properties

  609 Smithfield Ave, Winchester, VA 22601
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  /23

  $270,000 Sold Sep 24, 2025

  209 S Braddock St, Winchester, VA 22601

  • 2 Beds
  • 2 Baths
  • 1,446 Sq Ft
  • Built 1900

  Last Sold Summary

  • $187/SF
  • 52 Days On Market

  Current Estimated Value $282,349

  Last Listing Agent Ela Moyer Long & Foster Real Estate, Inc.

  209 S Braddock St, Winchester, VA 22601
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  Est $436,245 Not Listed For Sale

  206 N Kent St, Winchester, VA 22601

  • 2 Beds
  • 4 Baths
  • 2,160 Sq Ft
  • Built 2022

  206 N Kent St, Winchester, VA 22601

  Last Sold Summary

  • 4% Below List Price
  • $211/SF
  • 0 Days On Market

  Last Sold Price $455,400

  Last Listing Agent Jason Aikens RE/MAX
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  $270,000 Coming Soon

  • 2 Beds
  • 1.5 Baths
  • 1,024 Sq Ft

  2640 Limestone Ct, Winchester, VA 22601

  Discover this charming Colonial-style townhouse nestled in the desirable Limestone Court community. Built in 1994, this end-unit home offers a perfect blend of comfort and convenience. With 2 spacious bedrooms and 1.5 bathrooms, it's ideal for those seeking a cozy yet functional living space. The brick exterior exudes timeless appeal, while the efficient layout maximizes every square foot. Enjoy

  

  Ned Stock

  Berkshire Hathaway HomeServices PenFed Realty

  (540) 329-1991

  2640 Limestone Ct, Winchester, VA 22601
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  /22

  $1,797 - $2,507 per month

  Meadow Branch Luxury Apartments

  1 - 3 Beds

  424 Ridgewood Ln, Winchester, VA 22601

  Welcome to Meadow Branch, where luxury and convenience are standard. Our community offers beautiful 1,2 and 3 bedroom apartment homes. Community means convenience and at Meadow Branch, everything you need is nearby. We are conveniently located adjacent to Winchester Medical Center and 2 miles from Old Town Winchester.

  424 Ridgewood Ln, Winchester, VA 22601
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  $520,000 Sold Jun 19, 2025

  423 W Monmouth St, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 2,296 Sq Ft
  • Built 1963

  Last Sold Summary

  • $226/SF
  • 13 Days On Market

  Current Estimated Value $516,817

  Last Listing Agent Lindsey Richardson ERA Oakcrest Realty, Inc.

  423 W Monmouth St, Winchester, VA 22601
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  Est $288,647 Not Listed For Sale

  228 Weems Ln, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 734 Sq Ft
  • Built 1950

  228 Weems Ln, Winchester, VA 22601

  Last Sold Summary

  • 14% Above List Price
  • $346/SF
  • 8 Days On Market

  Last Sold Price $254,000

  Last Listing Agent Sam Smith Dream Real Estate

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