Winchester County, VA Homes

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  /17

  $199,900

  $15K PRICE DROP

  • Land
  • 15,681 Sq Ft
  • $555,278 per Acre

  506 Fairmont Ave, Winchester, VA 22601

  NEW CITY LOT! This newly configured lot in the heart of downtown Winchester has been expanded and is ready for you to build your dream home. Featuring a width of approximately 100 feet, you have plenty of space to accommodate nearly any home of your choice. As a bonus, the driveway will be on the neighboring lot, which allows even more buildable space. Additionally, you do not have to worry about

  Dan Whitacre Colony Realty

  506 Fairmont Ave, Winchester, VA 22601
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  /16

  $1,950 Plus Fees

  • 3 Beds
  • 2 Baths
  • 1,362 Sq Ft
  • Condo for Rent

  553 Highland Ave, Winchester, VA 22601

  Welcome to your new home in lovely Winchester, VA. This charming property offers the perfect balance of comfort and convenience, making it an ideal living space for those seeking a vibrant community with plenty to explore.Key property features include spacious bedrooms and bathrooms, providing ample room for relaxation and privacy. You’ll enjoy the benefits of central heating and cooling,

  553 Highland Ave, Winchester, VA 22601
• 

  

  

  /36

  $525,000

  Sold Nov 14, 2025

  2723 Windwood Dr, Winchester, VA 22601

  • 3 Beds
  • 3 Baths
  • 2,726 Sq Ft
  • Built 1999

  Last Sold Summary

  • $193/SF
  • 38 Days On Market

  Current Estimated Value $555,126

  Last Listing Agent LESLIE WEBB Long & Foster Real Estate, Inc.

  2723 Windwood Dr, Winchester, VA 22601
• 

  

  

  /26

  Est $422,211

  Not Listed For Sale

  444 Superior Ave, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • Built 2008

  444 Superior Ave, Winchester, VA 22601

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Kathryn Symenow CENTURY 21 New Millennium
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  /127

  $3,175,000

  • 6 Beds
  • 7 Baths
  • 8,593 Sq Ft

  730 Merrimans Ln, Winchester, VA 22601

  A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern Luxury Rarely does a property of this caliber, history, and scale become available within Winchester city limits. Perfectly positioned on 5.49 acres of breathtaking, park-like grounds, this historic masterpiece is a true private oasis. Painstakingly and lovingly renovated, the estate offers an unparalleled blend of 18th-century charm

  Justin Mistretta Berkshire Hathaway HomeServices PenFed Realty

  730 Merrimans Ln, Winchester, VA 22601
• 

  

  /13

  $2,000 Per Month

  • 800 Sq Ft
  • Condo for Rent

  2971 Valley Ave, Winchester, VA 22601

  Fully furnished loft style apartments. Lower level consists of living room, dining room, kitchen and bath. The bedroom is on the second level. These are full furnished units that allow pets. Perfect all inclusive rental. Owners pays for everything to include cable and internet. These units can be rented weekly also

  Meridee Powars Link Realty Services LLC

  2971 Valley Ave, Winchester, VA 22601
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  /47

  $555,000

  Sold Dec 22, 2025

  2307 Stoneridge Rd, Winchester, VA 22601

  • 5 Beds
  • 3.5 Baths
  • 3,280 Sq Ft
  • Built 2016

  Last Sold Summary

  • $169/SF
  • 5 Days On Market

  Current Estimated Value $592,540

  Last Listing Agent Dave Spence RE/MAX Roots

  2307 Stoneridge Rd, Winchester, VA 22601
• 

  

  /24

  Est $430,272

  Not Listed For Sale

  428 Superior Ave, Winchester, VA 22601

  • 4 Beds
  • 3 Baths
  • 2,288 Sq Ft
  • Built 1967

  428 Superior Ave, Winchester, VA 22601

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Devin Moore Innovation Properties, LLC
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  /39

  $449,900

  Pending

  • 2 Beds
  • 2 Baths
  • 2,370 Sq Ft

  443 Fairmont Ave, Winchester, VA 22601

  So much potential !!! Great location, private yard, lots of square feet. Lot is 3/4 acre !Needs TLC. Listed $120,000 under tax assessment to allow room for updating. Kitchen has Corion counter tops , great cabinets. Very large room with beautiful book case built in, has fantastic screened in porch, Very large ( 24 X 24 ) family room with fireplace .

  Jeff Webber Long & Foster Real Estate, Inc.

  443 Fairmont Ave, Winchester, VA 22601
• 

  

  /14

  $1,650

  Total Monthly Price

  • Studio
  • 1 Bath
  • 850 Sq Ft
  • August Only: Submit your application this month and pay a reduced application fee of just $32.Cha...

  505 N Cameron St, Winchester, VA 22601

  Beautifully renovated ground level unit in a classic 1920s home offering the perfect blend of historic charm and modern finishes. This bright and inviting apartment features high ceilings, abundant natural light, and updated appliances throughout, including a private washer and dryer, dishwasher, refrigerator, and garbage disposal.The spacious bathroom offers a full tub and shower

  505 N Cameron St, Winchester, VA 22601
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  /44

  $438,000

  Sold May 08, 2026

  21 W Pall Mall St, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 1,805 Sq Ft
  • Built 1930

  Last Sold Summary

  • 3% Above List Price
  • $243/SF
  • 10 Days On Market

  Current Estimated Value $426,691

  Last Listing Agent Allyson Lenz Compass

  21 W Pall Mall St, Winchester, VA 22601
• 

  

  /43

  Est $446,039

  Not Listed For Sale

  441 Superior Ave, Winchester, VA 22601

  • 2 Beds
  • 2 Baths
  • 1,672 Sq Ft
  • Built 1998

  441 Superior Ave, Winchester, VA 22601

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Curtis Siever NextHome Realty Select
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  /96

  $459,999

  $30K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 1,887 Sq Ft

  419 Summit Ave, Winchester, VA 22601

  Welcome Home! This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and granite countertops in the kitchen, this home combines style and functionality. A new roof adds peace of mind, and the fully finished lower level provides additional living space for relaxation or entertainment. With 5 spacious

  Waqas Abbasi Lifestyle Realty, LLC.

  419 Summit Ave, Winchester, VA 22601
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  /15

  $1,350 Per Month

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

  204 E Whitlock Ave, Winchester, VA 22601

  Conveniently located near Downtown Winchester, Shenandoah University, shopping, restaurants, and other everyday amenities, this well-maintained 2-bedroom, 1-bath townhome offers comfortable living with plenty of functional space. The main and upper levels feature hardwood flooring, while the updated eat-in kitchen has durable vinyl flooring. Exceptional closet space throughout the home provides

  Meghan Pachas MAP Property Solutions, LLC.

  204 E Whitlock Ave, Winchester, VA 22601
• 

  

  /46

  $506,000

  Sold May 13, 2026

  312 W Cecil St, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,698 Sq Ft
  • Built 1915

  Last Sold Summary

  • 3% Above List Price
  • $298/SF
  • 5 Days On Market

  Current Estimated Value $491,290

  Last Listing Agent Jeanne Mezzatesta Colony Realty

  312 W Cecil St, Winchester, VA 22601
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  /39

  Est $400,770

  Not Listed For Sale

  417 Superior Ave, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,747 Sq Ft
  • Built 1964

  417 Superior Ave, Winchester, VA 22601

  Last Sold Summary

  • 79 Days On Market

  Last Listing Agent Bruce Elsey Long & Foster Real Estate, Inc.
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  /28

  $400,000

  $29K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,432 Sq Ft

  115 E Monmouth St, Winchester, VA 22601

  Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

  Mafe Zambrano Inmobiliaria De Las Casas LLC

  115 E Monmouth St, Winchester, VA 22601
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  /50

  $1,425

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • Condo for Rent

  2533 Bradford Ct, Winchester, VA 22601

  The Flats of Winchester is an SDF Residential community located in Winchester, VA, offering a blend of renovated 1- and 2-bedroom apartments. The property features front patio gardens throughout, along with a unique landscape that sets it apart from other apartment complexes while preserving the quaint charm of the surrounding communityYour new home comes freshly remodeled and equipped

  2533 Bradford Ct, Winchester, VA 22601
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  /38

  $449,990

  Sold Sep 18, 2025

  1823 Reese Ct, Winchester, VA 22601

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

  Move in Ready Sold Summary

  • $238/SF
  • 6 Days On Market

  D.R. Horton Abrams Crossing at Meadow Branch

  1823 Reese Ct, Winchester, VA 22601
• 

  

  /54

  Est $364,354

  Not Listed For Sale

  444 Imperial St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,221 Sq Ft
  • Built 1959

  444 Imperial St, Winchester, VA 22601

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Alexandra Brown Spring Hill Real Estate, LLC.
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  /33

  $399,000

  $26K PRICE DROP

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

  1025 S Loudoun St, Winchester, VA 22601

  TONS OF UPGRADES! This home has been updated top to bottom. From the roof, windows, kitchen, bathrooms, light fixtures, HVAC, and so on. Located just 1 block from Handley High School, this home and all of its high end improvements make it a treasure waiting to be discovered. As you walk through this home you'll notice that a ton of care and thoughtfulness was put into what it is today. The

  Michael Sprague Samson Properties

  1025 S Loudoun St, Winchester, VA 22601
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  /18

  $2,300 Per Month

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft
  • House for Rent

  317 S Kent St, Winchester, VA 22601

  Charming 1931 brick home available for rent! This spacious home features 4 bedrooms, 1 full bath and 1 half bath, and the convenience of a main-level washer and dryer. Each bedroom includes ample closet space. Relax on the welcoming front porch or enjoy the fenced in backyard. The home is located right next to the Ruth Jackson Memorial Park and the Green Circle entrance is right across the

  Danielle Spriggs Samson Properties

  317 S Kent St, Winchester, VA 22601
• 

  

  /31

  $325,000

  Sold Dec 30, 2025

  414 Elm St, Winchester, VA 22601

  • 4 Beds
  • 2 Baths
  • 915 Sq Ft
  • Built 1960

  Last Sold Summary

  • $355/SF
  • 109 Days On Market

  Current Estimated Value $330,236

  Last Listing Agent Aracely Rivera First Decision Realty LLC

  414 Elm St, Winchester, VA 22601
• 

  

  /14

  Est $396,403

  Not Listed For Sale

  3128 Papermill Rd, Winchester, VA 22601

  • 3 Beds
  • 3 Baths
  • 1,970 Sq Ft
  • Built 2002

  3128 Papermill Rd, Winchester, VA 22601

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Natalie Dalecky ERA Oakcrest Realty, Inc.
• 

  

  /10

  $399,000

  • Land
  • 3,920 Sq Ft
  • $4,433,333 per Acre

  1 N Braddock St, Winchester, VA 22601

  Make Offer! Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and

  Gillian Greenfield Coldwell Banker Premier

  1 N Braddock St, Winchester, VA 22601
• 

  

  /14

  $1,695

  Total Monthly Price

  • 3 Beds
  • 1 Bath
  • 1,474 Sq Ft
  • House for Rent

  26 Jackson Ave, Winchester, VA 22601

  ***COMING SOON***Beautiful, large 3 bedroom 1 bath home with a nice sitting porch, fenced back yard, 1 car detached garage, storage shed.OIL HEATPETS PERMITTED WITH APPROVAL AND ADDITIONAL FEE 3 Bedroom 1 Bath

  26 Jackson Ave, Winchester, VA 22601
• 

  

  /34

  $265,000

  Sold Sep 09, 2025

  2301 Tower Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1989

  Last Sold Summary

  • $276/SF
  • 90 Days On Market

  Current Estimated Value $273,074

  Last Listing Agent Clint Pierpoint NextHome Realty Select

  2301 Tower Ave, Winchester, VA 22601
• 

  

  /68

  Est $407,018

  Not Listed For Sale

  3020 Papermill Rd, Winchester, VA 22601

  • 4 Beds
  • 2 Baths
  • 2,902 Sq Ft
  • Built 1961

  3020 Papermill Rd, Winchester, VA 22601

  Last Sold Summary

  • 68 Days On Market

  Last Listing Agent Dave Spence RE/MAX Roots
• 

  

  /30

  $385,000

  • 3 Beds
  • 1 Bath
  • 1,280 Sq Ft

  540 Bellview Ave, Winchester, VA 22601

  Attention investors! Charming rambler just minutes from historic Old Town Winchester with convenient access to I-81, making commuting simple and stress-free. This inviting home features beautiful hardwood floors, a spacious living room with a cozy fireplace, and a formal dining room perfect for hosting family and friends. The kitchen offers easy access to the backyard, creating a seamless flow

  Heloisa Amar Samson Properties

  540 Bellview Ave, Winchester, VA 22601
• 

  

  /38

  $1,550 Per Month

  • 2 Beds
  • 1.5 Baths
  • 5,504 Sq Ft
  • Townhouse for Rent

  527 Gray Ave Unit 1, Winchester, VA 22601

  Renovated townhouse end unit in the heart of Winchester. Rent includes water, sewer, exterior maintenance and lawn care. Unit ready for immediate move in. Washer/ Dryer hook ups available in unit. Owner looking for a credit score of 650 or above. Pets allowed for a monthly fee.

  Joshua Jenkins Samson Properties

  527 Gray Ave Unit 1, Winchester, VA 22601
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  /48

  $574,900

  Sold Oct 17, 2025

  1629 Pondview Dr, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 2,602 Sq Ft
  • Built 1995

  Last Sold Summary

  • $221/SF
  • 83 Days On Market

  Current Estimated Value $606,416

  Last Listing Agent Kerry & Ed Stinson Berkshire Hathaway HomeServices PenFed Realty

  1629 Pondview Dr, Winchester, VA 22601
• 

  

  /29

  Est $319,995

  Not Listed For Sale

  3141 Papermill Rd, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,183 Sq Ft
  • Built 1950

  3141 Papermill Rd, Winchester, VA 22601

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Dalton Stem LPT Realty, LLC
• 

  

  /31

  $545,000

  $15K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,068 Sq Ft

  110 Russelcroft Rd, Winchester, VA 22601

  Nestled in the established Cedarmeade community, this beautifully updated 4-bedroom, 3-bath ranch home offers the perfect combination of comfort, style, and functionality. With over 2,000 square feet of finished living space, this home is designed to accommodate both everyday living and effortless entertaining. Step inside to find warm hardwood flooring, abundant natural light, and thoughtfully

  Grace Mooney Coldwell Banker Premier

  110 Russelcroft Rd, Winchester, VA 22601
• 

  

  /12

  $1,150

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  22 Peyton St Unit 3, Winchester, VA 22601

  22 Peyton St Unit 3, Winchester, VA 22601
• 

  

  /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
• 

  

  /20

  Est $306,583

  Not Listed For Sale

  3113 Papermill Rd, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 895 Sq Ft
  • Built 1956

  3113 Papermill Rd, Winchester, VA 22601

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Marcy Cantatore Corcoran McEnearney
• 

  

  /10

  $239,000

  $6K PRICE DROP Pending

  • 2 Beds
  • 2.5 Baths
  • 1,280 Sq Ft

  2967 Sorrell Ct, Winchester, VA 22601

  This diamond in the rough has solid bones and plenty of potential for the right buyer. The HVAC system is only two years old, the water heater is brand new, and both full bathrooms have already been updated. The home could use some fresh paint, and the dishwasher is currently not working, but the major systems are in great shape—making this an excellent opportunity for a starter home or

  Jamie Cook Treck Realty LLC

  2967 Sorrell Ct, Winchester, VA 22601
• 

  

  /10

  $1,500 Per Month

  • 2 Beds
  • 2 Baths
  • 23,305 Sq Ft
  • Condo for Rent

  443 Millwood Ave Unit 3, Winchester, VA 22601

  Clean and updated 2-bedroom, 2-bath apartment ideally located near Shenandoah University and downtown Winchester. Features include a functional floor plan, in-unit washer and dryer, and two full bathrooms for added convenience. One assigned parking space conveys, plus street parking options nearby. Situated above commercial space with close proximity to local restaurants, shops, and major

  Rachel Olsen Keller Williams Realty

  443 Millwood Ave Unit 3, Winchester, VA 22601
• 

  

  /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
• 

  

  /37

  Est $359,000

  Not Listed For Sale

  2905 First St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1968

  2905 First St, Winchester, VA 22601

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Melissa Johnston ERA Oakcrest Realty, Inc.

Showing Results 161 - 200, Page 5 of 18