Winchester County, VA Homes

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  $585,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,909 Sq Ft

  328 Sheridan Ave, Winchester, VA 22601

  Timeless charm meets thoughtful updates in this beautifully maintained all-brick 1958 home, offering effortless one-level living with a warm retro vibe. Freshly painted throughout and enhanced with new quartz countertops, classic subway tile backsplash, updated sink and faucet, and stylish new lighting, this home blends character with modern comfort. The main level is inviting and functional,

  Mary Casselano Dream Real Estate

  328 Sheridan Ave, Winchester, VA 22601
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  $1,595 per month

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Townhouse for Rent

  28 E Pall Mall St, Winchester, VA 22601

  Welcome to 28 E Pall Mall Street, a charming rental located just minutes from the vibrant Old Town Winchester area. This well-maintained home offers the perfect blend of comfort, convenience, and historic charm. Step inside to find spacious living areas filled with natural light, comfortable bedrooms, and a functional layout ideal for everyday living. The home features a bright kitchen with

  tiffany pollard Coldwell Banker Elite

  28 E Pall Mall St, Winchester, VA 22601
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  $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 $575,724

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

  1629 Pondview Dr, Winchester, VA 22601
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  Est $306,353 Not Listed For Sale

  2917 First St, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,250 Sq Ft
  • Built 1952

  2917 First St, Winchester, VA 22601

  Last Sold Summary

  • 11% Above List Price
  • $220/SF
  • 90 Days On Market

  Last Sold Price $275,000

  Last Listing Agent James King RE/MAX
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  $279,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,176 Sq Ft

  239 Chestnut St, Winchester, VA 22601

  ******Price Reduction******239 Chestnut Street is a charming rancher in the heart of Winchester. 2 bedrooms, 1 bath, a large rear deck, eat in kitchen, laundry room could be converted into a third bedroom. Building in the back yard could be used as storage or a 1 car garage. This is a solid starter or downsizing home convenient to shopping,schools and parks. A little TLC will go a long way

  William Wertz Wildhawks Realty LLC

  239 Chestnut St, Winchester, VA 22601
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  $1,975 per month

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Condo for Rent

  342 Fairmont Ave Unit 3, Winchester, VA 22601

  Gorgeous, large, fully furnished two bedroom apartment.Amazing location in beautiful well-established neighborhood. Just two short walking blocks to the Old Town Winchester pedestrian mall with shops, restaurants, cafes and entertainment.Located inside an 1840s hstoric house, this two bedroom apartment features original hardwood floors, high ceilings, crown molding, large windows,

  342 Fairmont Ave Unit 3, Winchester, VA 22601
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  $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 $589,555

  Last Listing Agent John Scully Colony Realty

  107 Roszel Rd, Winchester, VA 22601
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  /31

  Est $284,625 Not Listed For Sale

  2944 Second St, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 850 Sq Ft
  • Built 1953

  2944 Second St, Winchester, VA 22601

  Last Sold Summary

  • 12% Above List Price
  • $298/SF
  • 126 Days On Market

  Last Sold Price $253,300

  Last Listing Agent Amira Wali Spring Hill Real Estate, LLC.
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  $889,000 Under Contract

  • 5 Beds
  • 4.5 Baths
  • 4,957 Sq Ft

  1540 Meadow Branch Ave, Winchester, VA 22601

  An exceptional offering of luxury living in the City of Winchester, this stately brick residence presents 4,958 square feet or refined, custom-designed living space. The home features 5 generously sized bedrooms and 4.5 beautifully appointed bathrooms, thoughtfully crafted for both elegant entertaining and everyday comfort. Rich architectural details and custom finishes are showcased throughout,

  John Schroth Colony Realty

  1540 Meadow Branch Ave, Winchester, VA 22601
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  $2,395 per month

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • Townhouse for Rent

  3141 Eton Place, Winchester, VA 22601

  NEWER END UNIT, 2-CAR GARAGE LUXURY TOWNHOUSE! 3 BR 2.5 BA w/ over 2,100 sq ft and 9-ft ceilings on three levels with HIGH end finishes throughout and a 4 foot extension on all levels! The main level features a center gourmet kitchen with upgraded cabinets, stainless steel appliances, quartz countertops, oversized island, luxury vinyl plank flooring and upgrades throughout. Kitchen opens to a

  Susie Kontzias Suburban Homes Realty, Inc.

  3141 Eton Place, Winchester, VA 22601
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  $850,000 Sold May 13, 2025

  765 Seldon Dr, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 4,144 Sq Ft
  • Built 1998

  Last Sold Summary

  • $205/SF
  • 0 Days On Market

  Current Estimated Value $851,728

  Last Listing Agent Dan Whitacre Colony Realty

  765 Seldon Dr, Winchester, VA 22601
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  /19

  Est $323,808 Not Listed For Sale

  2928 First St, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,472 Sq Ft
  • Built 1972

  2928 First St, Winchester, VA 22601

  Last Sold Summary

  • 22% Above List Price
  • $180/SF
  • 11 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Kimberly Schroeder Long & Foster Real Estate, Inc.
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  $300,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,789 Sq Ft

  501 Battle Ave, Winchester, VA 22601

  Unwind on the covered front porch of this charming stone Cape Cod, ideally located on a spacious corner lot with sidewalks and a large, fenced backyard. Inside, the inviting living room features hardwood floors and a brick gas-log fireplace—perfect for cozy evenings. Hardwood flooring continues throughout the home, complemented by a convenient kitchen and dining combination. Two bedrooms are

  Susan Caulfield Pearson Smith Realty, LLC

  501 Battle Ave, Winchester, VA 22601
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  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • House for Rent

  226 Allison Ave, Winchester, VA 22601

  Great location by Winchester Medical Center hospital and downtown Winchester's Old Town pedestrian mall with shops, restaurants, cafes and entertainment. Split level house by Whittier Field and park.Three bedrooms Two full bathsLarge fenced yard Beautiful landscaping Parking spaces Utility Laundry Room with Washer & Dryer No pets.

  226 Allison Ave, Winchester, VA 22601
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  $675,000 Sold Feb 12, 2026

  800 Lake Dr, Winchester, VA 22601

  • 5 Beds
  • 4 Baths
  • 4,576 Sq Ft
  • Built 2010

  Last Sold Summary

  • $148/SF
  • 87 Days On Market

  Current Estimated Value $791,647

  Last Listing Agent Lisa Behr Hunt Country Sotheby's International Realty

  800 Lake Dr, Winchester, VA 22601
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  Est $243,912 Not Listed For Sale

  521 Monticello St, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 1,064 Sq Ft
  • Built 1981

  521 Monticello St, Winchester, VA 22601

  Last Sold Summary

  • 16% Above List Price
  • $197/SF
  • 4 Days On Market

  Last Sold Price $210,000

  Last Listing Agent Ned Stock BHHS PenFed (actual)
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  $1,200,000 Open Sat 11AM - 2PM

  • 6 Beds
  • 5 Baths
  • 6,682 Sq Ft

  217 W Boscawen St, Winchester, VA 22601

  Historic Water Street Inn a magnificent legacy residence, profitable Bed & Breakfast, or sophisticated professional office opportunity! Located in Winchester's Historic District, two blocks from Old Town Walking Mall! Six large bedrooms and five full baths, this historically significant property is one of a kind, offering private garden spaces, romantic terraces, sunlight filled porches, and

  Gillian Greenfield Coldwell Banker Premier

  217 W Boscawen St, Winchester, VA 22601
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  $1,650 per month

  • 2 Beds
  • 1.5 Baths
  • 1,047 Sq Ft
  • Townhouse for Rent

  1105 Franklin St Unit 1105, Winchester, VA 22601

  2 levels TOWNHOUSE, 2 bathrooms and 2 bedroom with large walking closet, large living room and Eat in kitchen with new Laundry set, near I-81,Rt-70, Rt 50 and medical college, hospital, Amazon & many auto warehouses, TREK & many industrial companies, also 35 minutes to one hour drive for many NOVA SUBURB like Leesburg, Dulles airport, DC Metro, Tyson’s corner and Charleston casino and near by

  Ram Beladia First American Real Estate

  1105 Franklin St Unit 1105, Winchester, VA 22601
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  $330,000 Sold Jun 20, 2025

  111 Montague Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,172 Sq Ft
  • Built 1955

  Last Sold Summary

  • $282/SF
  • 3 Days On Market

  Current Estimated Value $327,425

  Last Listing Agent Tracie Clawson ERA Oakcrest Realty, Inc.

  111 Montague Ave, Winchester, VA 22601
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  /22

  Est $266,874 Not Listed For Sale

  514 Armour Dale, Winchester, VA 22601

  • 2 Beds
  • 1 Bath
  • 765 Sq Ft
  • Built 1955

  514 Armour Dale, Winchester, VA 22601

  Last Sold Summary

  • 7% Above List Price
  • $325/SF
  • 4 Days On Market

  Last Sold Price $249,000

  Last Listing Agent Katy Kidwell Burch Real Estate Group, LLC
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  $320,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft

  1610 S Loudoun St, Winchester, VA 22601

  Welcome to this charming Cape Cod located in the heart of Winchester. Centrally situated just minutes from Old Town Winchester and Shenandoah University, this home offers both convenience and character.Step inside to a spacious living room featuring a cozy fireplace, which flows seamlessly into the kitchen and continues on to the dining room, creating an inviting layout for everyday living

  Heloisa Amar Samson Properties

  1610 S Loudoun St, Winchester, VA 22601
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  $2,000 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  130 Montague Ave, Winchester, VA 22601

  Cute brick two bedroom one bathroom house with family room, dining room, kitchen and additional unfinished attic space for storage. There is a fenced in backyard with patio and shed. Off street parking. Shared washer dryer with basement tenant. Utilities included. No pets, No smoking. $2000/month. Available 4/1. First months rent plus $2000 deposit required

  130 Montague Ave, Winchester, VA 22601
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  $370,000 Sold Jul 18, 2025

  625 Butler Ave, Winchester, VA 22601

  • 5 Beds
  • 2.5 Baths
  • 1,050 Sq Ft
  • Built 1968

  Last Sold Summary

  • $352/SF
  • 4 Days On Market

  Current Estimated Value $360,846

  Last Listing Agent Aracely Rivera First Decision Realty LLC

  625 Butler Ave, Winchester, VA 22601
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  Est $341,944 Not Listed For Sale

  517 Armour Dale, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 1,600 Sq Ft
  • Built 1935

  517 Armour Dale, Winchester, VA 22601

  Last Sold Summary

  • 15% Below List Price
  • $250/SF
  • 3 Days On Market

  Last Sold Price $400,000

  Last Listing Agent John Ashton Equity Realty
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  $1,100,000

  • Land
  • 2.3 Acres
  • $478,261 per Acre

  0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601

  2.3 Acre Outparcel on Pleasant Valley Road for Sale Neighbors include Walmart, Ross, Target, Panera Bread, Olive Garden, Petco, and the list goes on! Zoned CM1, ideal for auto sales, offices, retail, and flex development. All utilities to site. Outstanding proximity to massive commercial and multifamily growth. VA's fastest growing City in it's fastest growing commercial district. Almost 500'

  Gillian Greenfield Coldwell Banker Premier

  0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601
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  $2,350 per month

  • 3 Beds
  • 2 Baths
  • 1,291 Sq Ft
  • House for Rent

  216 Wood Ave, Winchester, VA 22601

  Remodeled 3-bedroom, 2-bath brick rancher located in the desirable Northwestern Hills area with small park. This home offers hardwood flooring throughout the main level, a bright living space, and an updated kitchen featuring granite countertops and stainless steel appliances. Newly remodeled bathrooms & kitchen ! Freshly painted with refinished floors, the home feels clean, modern, and move-in

  Sheila Pack RE/MAX Roots

  216 Wood Ave, Winchester, VA 22601
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  $650,000 Sold Sep 16, 2025

  504 Old Fort Rd, Winchester, VA 22601

  • 5 Beds
  • 6 Baths
  • 3,824 Sq Ft
  • Built 2003

  Last Sold Summary

  • $170/SF
  • 74 Days On Market

  Current Estimated Value $658,529

  Last Listing Agent Dallas Croft Samson Properties

  504 Old Fort Rd, Winchester, VA 22601
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  Est $519,957 Not Listed For Sale

  605 Kernstown Ct, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,568 Sq Ft
  • Built 1997

  605 Kernstown Ct, Winchester, VA 22601

  Last Sold Summary

  • 7% Above List Price
  • $189/SF
  • 14 Days On Market

  Last Sold Price $485,000

  Last Listing Agent Omar Gonzalez Real Living at Home
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  $215,000

  • Land
  • 0.36 Acre
  • $597,222 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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  $2,000 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  130 Montague Ave, Winchester, VA 22601

  Cute brick two bedroom one bathroom house with family room, dining room, kitchen and additional unfinished attic space for storage. There is a fenced in backyard with patio and shed. Off street parking. Shared washer dryer with basement tenant. Utilities included. No pets, No smoking. $2000/month. Available 4/1. First months rent plus $2000 deposit required

  130 Montague Ave, Winchester, VA 22601
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  $425,000 Sold Mar 11, 2026

  431 Jefferson St, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft
  • Built 1956

  Last Sold Summary

  • 1% Above List Price
  • $260/SF
  • 4 Days On Market

  Current Estimated Value $443,107

  Last Listing Agent Dan Whitacre Colony Realty

  431 Jefferson St, Winchester, VA 22601
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  Est $508,564 Not Listed For Sale

  3022 Saratoga Dr, Winchester, VA 22601

  • 4 Beds
  • 3 Baths
  • 2,312 Sq Ft
  • Built 2000

  3022 Saratoga Dr, Winchester, VA 22601

  Last Sold Summary

  • 4% Above List Price
  • $212/SF
  • 42 Days On Market

  Last Sold Price $489,000

  Last Listing Agent Brett Sowder RE/MAX
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  $347,500 Under Contract

  • 3 Beds
  • 1 Bath
  • 907 Sq Ft

  217 Myrtle Ave, Winchester, VA 22601

  PRICE IMPROVEMENT!! Newly renovated and move-in ready! Everything is brand new in this super cute ranch home with a craftsman-style feel. Located in the City of Winchester in Northwestern Hills, schedule your appointment to see this stunning 3 BR 1 BA home with detached garage. New vinyl siding, roof, heat pump, GE appliances, cabinets, granite countertops, undercabinet lighting, flooring,

  Pamela Foltz Realty ONE Group Old Towne

  217 Myrtle Ave, Winchester, VA 22601
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  $1,200 per month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  811 S Braddock St Unit 6, Winchester, VA 22601

  2 bedroom 1 bath 2nd floor apartment now available. Less than 1 block away from Handley High School. Hardwood floors throughout. Water/sewer included, tenant pays electric. Coin op laundry located in finished basement area. Application requried, Apply on listers website or NVAR or VAR rental application with $50 application fee paid by cash or money order, no personal checks. No animals. No

  Mandie Gladwell OliveTree Property Group, LLC

  811 S Braddock St Unit 6, Winchester, VA 22601
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  $405,000 Sold Apr 29, 2025

  119 E Germain St, Winchester, VA 22601

  • 2 Beds
  • 2.5 Baths
  • 1,769 Sq Ft
  • Built 1866

  Last Sold Summary

  • $229/SF
  • 8 Days On Market

  Current Estimated Value $405,108

  Last Listing Agent Tiffany Hunter ERA Oakcrest Realty, Inc.

  119 E Germain St, Winchester, VA 22601
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  Est $585,801 Not Listed For Sale

  3026 Saratoga Dr, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 3,379 Sq Ft
  • Built 1998

  3026 Saratoga Dr, Winchester, VA 22601

  Last Sold Summary

  • 4% Above List Price
  • $167/SF
  • 3 Days On Market

  Last Sold Price $565,000

  Last Listing Agent Stephanie Ryall Realty ONE Group Old Towne
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  $150,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 882 Sq Ft

  222 Liberty Ave, Winchester, VA 22601

  Calling all investors, contractors, and savvy home buyers! Seize this incredible opportunity to own a 3-bedroom, 1-bath home in an up-and-coming Winchester neighborhood. This property is the definition of "sweat equity," and the heavy lifting has already been started for you. Property has had a recently survey and property lines are marked. The current owner has completed the two hardest parts of

  Kandi McKenzie Realty ONE Group Old Towne

  222 Liberty Ave, Winchester, VA 22601
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  $1,500 per month

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft
  • Townhouse for Rent

  127-A Peyton St, Winchester, VA 22601

  Gorgeous two story apartment with private entrance in the heart of historic downtown Winchester. Walking distance from the Old Town Winchester pedestrian mall with shops, restaurants, cafes and entertainment and the beautiful Handley library.Huge Two bedroom 1.5 bath Apartment with beautiful details located in the bottom two levels of a four story house built in the early 1890s. This is a

  127-A Peyton St, Winchester, VA 22601
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  $375,000 Sold Feb 06, 2026

  318 E Piccadilly St, Winchester, VA 22601

  • 4 Beds
  • 1.5 Baths
  • 1,953 Sq Ft
  • Built 1929

  Last Sold Summary

  • 6% Below List Price
  • $192/SF
  • 40 Days On Market

  Current Estimated Value $390,676

  Last Listing Agent Dan Whitacre Colony Realty

  318 E Piccadilly St, Winchester, VA 22601
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  Est $447,971 Not Listed For Sale

  2817 Broadview St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 2,355 Sq Ft
  • Built 1955

  2817 Broadview St, Winchester, VA 22601

  Last Sold Summary

  • 10% Below List Price
  • $212/SF
  • 47 Days On Market

  Last Sold Price $499,900

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

Showing Results 201 - 240, Page 6 of 18