12,945

Winchester County, VA Homes

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  • /31

    $329,000

    $30K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    608 Dunlap St, Winchester, VA 22601

    Charming 3-bedroom, 1-bath ranch-style home in a highly convenient Winchester location! This well-maintained home is in great condition and has been freshly painted, offering a clean, move-in ready feel. Featuring beautiful hardwood floors throughout and a fully fenced backyard—perfect for pets, entertaining, or relaxing evenings. Central heating and air conditioning for year-round comfort.

    Richard Butcher Coldwell Banker Premier

    608 Dunlap St, Winchester, VA 22601
  • /47

    $2,000 Per Month

    • 3 Beds
    • 3 Baths
    • 2,052 Sq Ft
    • Townhouse for Rent

    824 Appleseed Ct, Winchester, VA 22601

    Fully renovated in 2025—this move-in-ready 3-level townhouse checks all the boxes.Step inside to fresh flooring, neutral paint, and a bright, modern feel throughout. The updated kitchen features granite countertops, stylish cabinetry, and newer appliances, opening into a comfortable living space with a cozy wood-burning fireplace. All three bathrooms have been completely redone with clean,

    Marisa Varley ERA Oakcrest Realty, Inc.

    824 Appleseed Ct, Winchester, VA 22601
  • /39

    $270,000

    Sold Jan 21, 2026

    423 Highland Ave, Winchester, VA 22601

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 1930

    Last Sold Summary

    • $208/SF
    • 44 Days On Market

    Current Estimated Value $265,455

    Last Listing Agent Carlos Soares Samson Properties

    423 Highland Ave, Winchester, VA 22601
    • /18

      Est $276,580

      Not Listed For Sale

      2947 Sorrell Ct, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,332 Sq Ft
      • Built 2001
      2947 Sorrell Ct, Winchester, VA 22601

      Last Sold Summary

      • 4 Days On Market

  • /34

    $364,900

    • 4 Beds
    • 2.5 Baths
    • 2,050 Sq Ft

    621 Patterson Ave, Winchester, VA 22601

    Enchanting Cape Cod in an ideal in‐town location, this home has a welcoming ease to it, offering 3–4 bedrooms and 2.5 bathrooms with a layout that adapts beautifully to everyday living. The main level includes two convenient bedrooms, a comfortable, light‐filled living room, a separate dining area, and a renovated kitchen featuring new cabinets and stainless‐steel appliances. In 2021, the home

    LESLIE WEBB Long & Foster Real Estate, Inc.

    621 Patterson Ave, Winchester, VA 22601
  • /137

    $3,500 Per Month

    • 4 Beds
    • 3 Baths
    • 3,060 Sq Ft
    • House for Rent

    209 N Washington St, Winchester, VA 22601

    Live in the heart of Historic Winchester! This beautifully restored 1853 home offers a rare opportunity to enjoy timeless character paired with modern comfort just blocks from the Old Town Walking Mall and steps from the Apple Blossom Parade Route. Boasting over 3,000 square feet of finished living space, this one-of-a-kind home showcases the craftsmanship of a bygone era with 10-foot ceilings,

    Chris Roszko Colony Realty

    209 N Washington St, Winchester, VA 22601
  • /34

    $450,000

    Sold Oct 17, 2025

    711 S Braddock St, Winchester, VA 22601

    • 3 Beds
    • 3.5 Baths
    • 2,052 Sq Ft
    • Built 2016

    Last Sold Summary

    • $219/SF
    • 7 Days On Market

    Current Estimated Value $466,640

    Last Listing Agent Dave Spence RE/MAX Roots

    711 S Braddock St, Winchester, VA 22601
    • /30

      Est $282,018

      Not Listed For Sale

      2955 Sorrell Ct, Winchester, VA 22601

      • 2 Beds
      • 1.5 Baths
      • 1,332 Sq Ft
      • Built 2001
      2955 Sorrell Ct, Winchester, VA 22601

      Last Sold Summary

      • 5 Days On Market

  • /11

    $649,900

    $50K PRICE DROP
    • Studio
    • 3,190 Sq Ft

    434-434 1/2 Fairmont Ave, Winchester, VA 22601

    Major Price Reduction.....ATTENTION ALL INVESTORS OR FUTURE LANDLORDS COME CHECKOUT THIS MULTI FAMILY 3 UNIT PROPERTY. IT CONSIST OF 2 HOUSES. EACH UNIT IS A 2 BED 1BATH EACH HAVE STOVE REFRIGERATOR MICROWAVE WASHER DRYER. CURRENTLY FULLY RENTED. SO NOW IS YOUR CHANCE TO OWN A TURNKEY RENTAL PROPERTY ALL WELL MAINTAINED WITH OFF STREET PARKING. CLOSE TO DOWNTOWN & SHOPPINGRESTRICTED SHOWINGS.

    Richard Kozlowski Long & Foster Real Estate, Inc.

    434-434 1/2 Fairmont Ave, Winchester, VA 22601
  • /12

    $1,100 Per Month

    • 1 Bed
    • 1 Bath
    • 6,578 Sq Ft
    • Condo for Rent

    213 E Whitlock Ave Unit B, Winchester, VA 22601

    The rental application is attached and available in the documents section.There is a $45 application fee for each applicant age 18 or older. Completed applications and application fees must be dropped off at our Winchester office. Application fees must be paid in cash.Applicants must be able to pass a background check and credit check.No Smoking Charming newly renovated one bedroom

    Joseph Clotzman Cambridge Premier Realty, LLC.

    213 E Whitlock Ave Unit B, Winchester, VA 22601
  • /105

    $1,149,000

    Sold Feb 20, 2026

    819 Armistead St, Winchester, VA 22601

    • 5 Beds
    • 3.5 Baths
    • 5,262 Sq Ft
    • Built 1989

    Last Sold Summary

    • 4% Below List Price
    • $218/SF
    • 1 Day On Market

    Current Estimated Value $1,147,584

    Last Listing Agent Natalie Langford ERA Oakcrest Realty, Inc.

    819 Armistead St, Winchester, VA 22601
    • /16

      Est $284,295

      Not Listed For Sale

      2975 Sorrell Ct, Winchester, VA 22601

      • 2 Beds
      • 2.5 Baths
      • 1,880 Sq Ft
      • Built 1990
      2975 Sorrell Ct, Winchester, VA 22601

      Last Sold Summary

  • /21

    $269,000

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    321 N Kent St, Winchester, VA 22601

    Wonderful opportunity to own in downtown Winchester! Walking distance to the Old Town Mall restaurants, shopping, the library and more. Easy access to Rt. 7 and 81. The main level has a nice open floor plan, consisting of kitchen, dining and living areas. The main level also features a half bath and bonus room, perfect for an office or den. Upstairs you will find three bedrooms, full bathroom and

    Amy Capitano MarketPlace REALTY

    321 N Kent St, Winchester, VA 22601
  • /24

    $1,900 Per Month

    • 3 Beds
    • 1 Bath
    • 1,956 Sq Ft
    • House for Rent

    233 Molden Dr, Winchester, VA 22601

    Enjoy comfortable living in this beautifully finished, fully furnished basement apartment with all utilities included. Nestled in a quiet residential neighborhood with easy access to I-81, this move-in-ready space offers the perfect combination of convenience and comfort. The apartment features luxury vinyl plank (LVP) flooring throughout, accented by beautiful exposed beams that add warmth and

    Heloisa Amar Samson Properties

    233 Molden Dr, Winchester, VA 22601
  • /44

    $782,000

    Sold Oct 03, 2025

    939 Buckner Dr, Winchester, VA 22601

    • 5 Beds
    • 4.5 Baths
    • 6,122 Sq Ft
    • Built 2000

    Last Sold Summary

    • $128/SF
    • 46 Days On Market

    Current Estimated Value $845,483

    Last Listing Agent Kiran K. Morzaria Parekh Samson Properties

    939 Buckner Dr, Winchester, VA 22601
    • /23

      Est $284,143

      Not Listed For Sale

      2950 Sorrell Ct, Winchester, VA 22601

      • 3 Beds
      • 3.5 Baths
      • 1,280 Sq Ft
      • Built 1990
      2950 Sorrell Ct, Winchester, VA 22601

      Last Sold Summary

      • 34 Days On Market

  • /33

    $353,990

    New Construction
    • 3 Beds
    • 4 Baths
    • 1,669 Sq Ft

    136 Swansong Place, Winchester, VA 22603

    Brand New, townhome with 3 finished levels, is under construction and will be ready for you to call home this Summer! With builder incentives available, there is no reason to wait to make this the next place you call home!Backing to open space in the newest section of Snowden Bridge, this home will be in close proximity to all of the newest amenities. Natural light flows through the kitchen

    Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

    136 Swansong Place, Winchester, VA 22603
  • /2

    $1,149 Per Month

    • 1 Bed
    • 1 Bath
    • 7,992 Sq Ft
    • Townhouse for Rent

    3103 3107 Shawnee Dr Unit 3, Winchester, VA 22601

    Ashley Crabill Coldwell Banker Premier

    3103 3107 Shawnee Dr Unit 3, Winchester, VA 22601
  • /42

    $464,000

    Sold Apr 13, 2026

    407 Jefferson St, Winchester, VA 22601

    • 3 Beds
    • 3 Baths
    • 2,805 Sq Ft
    • Built 1950

    Last Sold Summary

    • 3% Below List Price
    • $165/SF
    • 64 Days On Market

    Current Estimated Value $457,655

    Last Listing Agent Gillian Greenfield Coldwell Banker Premier

    407 Jefferson St, Winchester, VA 22601
    • /47

      Est $450,239

      Not Listed For Sale

      2894 Packer St, Winchester, VA 22601

      • 4 Beds
      • 2.5 Baths
      • 2,460 Sq Ft
      • Built 2006
      2894 Packer St, Winchester, VA 22601

      Last Sold Summary

      • 7 Days On Market

  • /51

    $480,000

    • 4 Beds
    • 2 Baths
    • 2,268 Sq Ft

    1306 Vanceright Cir, Winchester, VA 22601

    Filled with storybook charm and timeless character, this enchanting cottage-style home is much larger than it appears! Newly refinished hardwood floors flow throughout the home, blending warmth and elegance with everyday comfort. The updated kitchen offers modern convenience while maintaining the home's inviting charm. The partially finished basement provides flexible space for a family room,

    Julie Teets ERA Oakcrest Realty, Inc.

    1306 Vanceright Cir, Winchester, VA 22601
  • /5

    $950 Per Month

    • 1 Bed
    • 1 Bath
    • 4,672 Sq Ft
    • Condo for Rent

    418 N Loudoun St Unit 3, Winchester, VA 22601

    Historic Downtown Winchester: 2nd floor 1 bedroom apartment AVAILABLE NOW for rent! Water/sewer/trash included, tenant pays electric. No smoking and no animals please. $50 app fee paid by cash or money order or you may apply online thru website.

    Mandie Gladwell OliveTree Property Group, LLC

    418 N Loudoun St Unit 3, Winchester, VA 22601
  • /49

    $528,000

    Sold Jun 24, 2025

    645 Beehive Way, Winchester, VA 22601

    • 4 Beds
    • 2.5 Baths
    • 2,748 Sq Ft
    • Built 2007

    Last Sold Summary

    • $192/SF
    • 19 Days On Market

    Current Estimated Value $544,679

    Last Listing Agent Laura White ERA Oakcrest Realty, Inc.

    645 Beehive Way, Winchester, VA 22601
    • /46

      Est $453,493

      Not Listed For Sale

      201 Russelcroft Rd, Winchester, VA 22601

      • 3 Beds
      • 2.5 Baths
      • 3,066 Sq Ft
      • Built 1970
      201 Russelcroft Rd, Winchester, VA 22601

      Last Sold Summary

      • 10 Days On Market

  • /34

    $349,900

    $10K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    16 S Pleasant Valley Rd, Winchester, VA 22601

    Welcome to 16 S Pleasant Valley Rd, a beautifully maintained home offering a bright and inviting layout filled with natural light throughout. Enjoy your morning coffee on the rear patio and unwind in the evenings on the welcoming front porch while taking in the sunset views. The private fenced backyard provides the perfect space for relaxing, entertaining, or gathering around a fire pit with

    Vanessa Couture Samson Properties

    16 S Pleasant Valley Rd, Winchester, VA 22601
  • /11

    $1,149 Per Month

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

    1704 Roberts St Unit 2, Winchester, VA 22601

    RECENTLY RENOVATED, ALL-BRICK BUILDING THAT WAS COMPLETELY REDONE OVER LAST SEVERAL YEARS * UNIT HAS NEWER STAINLESS-STEEL APPLIANCES AND NEWER VINYL-PLANK FLOORING * EXTERIOR OF BUILDING WAS PAINTED IN 2018. NEW WINDOWS, NEW GUTTERS AND NEW ROOF ADDED IN 2018. ALL NEW ELECTRIC SERVICE IN 2018, ALSO * AWESOME KITCHEN W/NEWER CABINETS & GRANITE C'TOPS * REDONE BATH W/CERAMIC TILE FLOORS & TUB

    John Gregory Holmes Samson Properties

    1704 Roberts St Unit 2, Winchester, VA 22601
  • /3

    $271,000

    Sold Jul 01, 2025

    421 Superior Ave, Winchester, VA 22601

    • 3 Beds
    • 1.5 Baths
    • 1,197 Sq Ft
    • Built 1965

    Last Sold Summary

    • $226/SF
    • 23 Days On Market

    Current Estimated Value $430,067

    Last Listing Agent Cathy Caniford Crossroads, Realtors

    421 Superior Ave, Winchester, VA 22601
    • /73

      Est $455,968

      Not Listed For Sale

      212 W Cedarmeade Ave, Winchester, VA 22601

      • 5 Beds
      • 2.5 Baths
      • 2,899 Sq Ft
      • Built 1967
      212 W Cedarmeade Ave, Winchester, VA 22601

      Last Sold Summary

      • 91 Days On Market

  • /42

    $459,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,695 Sq Ft

    244 Parkway St, Winchester, VA 22601

    Discover the perfectly updated turnkey home you’ve been searching for in Historic Winchester. This beautifully maintained property offers 3 bedrooms and 2.5 bathrooms, including a spacious primary suite with a full bath and walk‐in closet, convenient main‐level laundry, and a flat, usable backyard with alley access—ideal for a future garage or additional off‐street parking. Gardeners will love

    Erika De Azagra ERA Oakcrest Realty, Inc.

    244 Parkway St, Winchester, VA 22601
  • /14

    $1,499 Per Month

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

    1111 Franklin St, Winchester, VA 22601

    2 levels TOWNHOUSE, 2 bathrooms and 2 bedroom with large walking closet, large living room and Eat in kitchen with laundry hook up, located near I-81,Rt-7 leesburg access, Rt 50 and medical college, hospital, Amazon & many auto warehouses, TREK & many other industrial companies, also 35 minutes to one hour drive for many NOVA SUBURB like Leesburg, Dulles airport, DC Metro, Tyson’s corner and

    Ram Beladia First American Real Estate

    1111 Franklin St, Winchester, VA 22601
  • /52

    $347,500

    Sold Apr 09, 2026

    217 Myrtle Ave, Winchester, VA 22601

    • 3 Beds
    • 1 Bath
    • 907 Sq Ft
    • Built 1961

    Last Sold Summary

    • 7% Below List Price
    • $383/SF
    • 50 Days On Market

    Current Estimated Value $341,861

    Last Listing Agent Pamela Foltz Realty ONE Group Old Towne

    217 Myrtle Ave, Winchester, VA 22601
    • /41

      Est $334,486

      Not Listed For Sale

      309 Wentworth Dr, Winchester, VA 22601

      • 3 Beds
      • 1.5 Baths
      • 1,148 Sq Ft
      • Built 1966
      309 Wentworth Dr, Winchester, VA 22601

      Last Sold Summary

      • 4 Days On Market

  • /64

    $499,999

    $19K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,837 Sq Ft

    1317 Caroline St, Winchester, VA 22601

    Conveniently located in the heart of Winchester, this spacious brick ranch offers the perfect combination of timeless character, thoughtful updates, and flexible living space. Situated on a nearly half-acre corner lot, the property provides room to spread out while remaining just minutes from Winchester Medical Center, shopping, dining, and major commuter routes. Inside, you'll find beautiful

    Kristina Towns Weichert Realtors - Blue Ribbon

    1317 Caroline St, Winchester, VA 22601
  • /14

    $1,400 Per Month

    • 2 Beds
    • 1 Bath
    • 1,248 Sq Ft
    • Condo for Rent

    2641 Valley Ave Unit C, Winchester, VA 22601

    Available Immediately!Character filled second level 2-bedroom, 1-bath apartment available for rent. An affordable opportunity for those seeking a basic and comfortable place to call home. Just minutes to Old Town Winchester, restaurants and grocery stores. Pets allowed with some restrictions and fees.

    Danielle Spriggs Samson Properties

    2641 Valley Ave Unit C, Winchester, VA 22601
  • /40

    $632,500

    Sold Apr 24, 2026

    162 Omps Dr, Winchester, VA 22601

    • 6 Beds
    • 3.5 Baths
    • 3,192 Sq Ft
    • Built 1990

    Last Sold Summary

    • 1% Below List Price
    • $198/SF
    • 13 Days On Market

    Current Estimated Value $629,490

    Last Listing Agent Kimberly Schroeder Long & Foster Real Estate, Inc.

    162 Omps Dr, Winchester, VA 22601
    • /33

      Est $383,514

      Not Listed For Sale

      430 Wentworth Dr, Winchester, VA 22601

      • 3 Beds
      • 2 Baths
      • 2,211 Sq Ft
      • Built 1954
      430 Wentworth Dr, Winchester, VA 22601

      Last Sold Summary

      • 108 Days On Market

  • /61

    $429,000

    $30K PRICE DROP Pending
    • 6 Beds
    • 3 Baths
    • 1,552 Sq Ft

    2250 Roosevelt Blvd, Winchester, VA 22601

    Charming Cape Cod nestled in a quiet residential neighborhood, just minutes from Route 11 and I-81 for easy commuting. This light-filled home welcomes you with a bright living room featuring a stunning stone fireplace as its centerpiece. The cabinet-packed kitchen is the heart of the home and offers granite countertops and a bar-height peninsula that opens seamlessly to the living room . The main

    Heloisa Amar Samson Properties

    2250 Roosevelt Blvd, Winchester, VA 22601
  • /26

    $1,550 Per Month

    • 1 Bed
    • 1 Bath
    • 5,222 Sq Ft
    • Condo for Rent

    105 N Loudoun St Unit 2, Winchester, VA 22601

    Welcome home to 105 N Loudoun St Apartment #2. This fully renovated apartment is the one you've been searching for! This fantastic second floor apartment is above the Village Square restaurant, on the walking mall. Minutes to Shenandoah University. Includes 1 assigned parking spot downtown! Shared washer and dryer a few steps from your door step. Water, Sewer, and trash are included! Call today

    Chris Roszko Colony Realty

    105 N Loudoun St Unit 2, Winchester, VA 22601
  • /36

    $284,900

    Sold Aug 15, 2025

    516 Hollingsworth Dr, Winchester, VA 22601

    • 2 Beds
    • 1 Bath
    • 813 Sq Ft
    • Built 1956

    Last Sold Summary

    • $350/SF
    • 28 Days On Market

    Current Estimated Value $274,030

    Last Listing Agent Chris Zarou Pearson Smith Realty, LLC

    516 Hollingsworth Dr, Winchester, VA 22601
    • /37

      Est $390,504

      Not Listed For Sale

      429 Beechcroft Rd, Winchester, VA 22601

      • 3 Beds
      • 2 Baths
      • 2,004 Sq Ft
      • Built 1965
      429 Beechcroft Rd, Winchester, VA 22601

      Last Sold Summary

      • 18 Days On Market

Showing Results 361 - 400, Page 10 of 18

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