Winchester, VA Homes

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  /30

  $349,900

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,412 Sq Ft

  2561 Apple Pie Ridge Rd, Winchester, VA 22603

  Welcome home to this beautifully updated rambler, offering comfort, character, and room to grow. The spacious front living room features gleaming hardwood floors and a large picture window that fills the space with natural light.Just off the garage, the remodeled den provides versatile living space perfect for a family room, home office, or recreation area. Recent updates include new drywall,

  

  Brock Harris

  Samson Properties

  2561 Apple Pie Ridge Rd, Winchester, VA 22603
• Explore Winchester

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  /74

  Starting at $1,700 Plus Fees

  • 1 - 4 Beds

  230 Spring St, Winchester, VA 22601

  Modern designs, elegant finishes, and the most desirable amenities await you at the area's 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

  The Local

  

  230 Spring St, Winchester, VA 22601
• 

  

  

  /4

  $190,000

  Sold Nov 25, 2025

  303 Barrington Ln, Winchester, VA 22601

  • 2 Beds
  • 1 Bath
  • 894 Sq Ft
  • Built 1994

  Last Sold Summary

  • $213/SF
  • 86 Days On Market

  Current Estimated Value $199,768

  Last Listing Agent Jim Stafford ERA Oakcrest Realty, Inc.

  303 Barrington Ln, Winchester, VA 22601
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  /29

  Not Listed For Sale

  709 Panther Dr, Winchester, VA 22602

  • 3 Beds
  • 2 Baths
  • 1,217 Sq Ft
  • Built 2025

  709 Panther Dr, Winchester, VA 22602

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Lisa Gill ERA Oakcrest Realty, Inc.
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  /36

  $484,990

  $15K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 1,953 Sq Ft

  111 Haida Ln, Winchester, VA 22602

  ••Welcome to The Retreat at Winding Creek, your haven in Winchester, VA, where luxury meets community living. ••Single Family * Two Level * 2528 Square Feet * 4 Bedrooms , 2.5 Baths * Two Car Garage Check out the 3D Matterport Tour! ••Why wait for a new build when you can have this stunning less than two-year-old home today? You’ll arrive just as the best parts of the neighborhood are opening up.

  

  Pamela Jones

  Long & Foster Real Estate, Inc.

  111 Haida Ln, Winchester, VA 22602
• 

  

  /8

  $1,450 Per Month

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

  2256 Roosevelt Blvd, Winchester, VA 22601

  Very spacious 2-bedroom, 1-bathroom townhouse offering comfortable living in a well-maintained setting. Features include a rear entrance leading to a private porch area and convenient parking. Shared laundry facilities are located within the complex. Ideally situated near shopping, restaurants, and Shenandoah University. Tenant pays all utilities. No smoking, no pets, and no vaping permitted.

  

  Frank Armstrong, IV

  Colony Realty

  2256 Roosevelt Blvd, Winchester, VA 22601
• 

  

  /51

  $425,000

  Sold Jun 10, 2026

  104 Van Buren Place, Winchester, VA 22602

  • 4 Beds
  • 2.5 Baths
  • 1,714 Sq Ft
  • Built 1990

  Last Sold Summary

  • 1% Above List Price
  • $248/SF
  • 6 Days On Market

  Current Estimated Value $420,528

  Last Listing Agent Leah Marabella Realty ONE Group Old Towne

  104 Van Buren Place, Winchester, VA 22602
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  /52

  Not Listed For Sale

  170 Munsee Cir, Winchester, VA 22602

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

  170 Munsee Cir, Winchester, VA 22602

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Brooks Sears Pearson Smith Realty, LLC
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  /39

  $399,000

  $46K PRICE DROP Under Contract

  • 6 Beds
  • 3 Baths
  • 1,917 Sq Ft

  623 Smithfield Ave, Winchester, VA 22601

  Spacious split-foyer home in the heart of Winchester featuring 6 bedrooms and 3 full bathrooms,. Well-maintained and located in a convenient neighborhood with no HOA. PRICE REDUCED TO SELL!

  

  Carlos Soares

  Samson Properties

  623 Smithfield Ave, Winchester, VA 22601
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  /38

  Starting at $1,837 Plus Fees

  • 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 conveniently located adjacent to Winchester Medical Center and 2 miles from Old Town Winchester.

  Denstock Meadow Branch LLC

  

  424 Ridgewood Ln, Winchester, VA 22601
• 

  

  /57

  $625,000

  Sold Oct 31, 2025

  101 Arthur Ln, Winchester, VA 22602

  • 5 Beds
  • 3.5 Baths
  • 4,787 Sq Ft
  • Built 2007

  Last Sold Summary

  • $131/SF
  • 5 Days On Market

  Current Estimated Value $633,932

  Last Listing Agent Scotti Sellers Compass

  101 Arthur Ln, Winchester, VA 22602
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  /12

  Not Listed For Sale

  124 Powhatan Trail, Winchester, VA 22602

  • 3 Beds
  • 3 Baths
  • 1,850 Sq Ft
  • Built 2025

  124 Powhatan Trail, Winchester, VA 22602

  Last Sold Summary

  • 197 Days On Market

  Last Listing Agent Jim Thomson Realty ONE Group Old Towne
• 

  

  /26

  $369,000

  • 3 Beds
  • 2.5 Baths
  • 1,737 Sq Ft

  614 Sherlock Trace, Winchester, VA 22601

  **Excellent Opportunity in the Heart of Winchester!** Don't miss the chance to own a well-located home in one of Winchester's most convenient areas. Situated on a quiet street, this property offers easy access to shopping, dining, schools, parks, and major commuter routes—everything that matters is just minutes away. Featuring **3 bedrooms** plus **two additional versatile rooms**, this home

  

  Carlos Soares

  Samson Properties

  614 Sherlock Trace, Winchester, VA 22601
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  /8

  $1,600 Per Month

  • 2 Beds
  • 2 Baths
  • 10,400 Sq Ft
  • Condo for Rent

  23 Taft Ave Unit 3, Winchester, VA 22601

  One of the largest 2-bedroom, 2-bathroom apartments in Winchester! This spacious second-floor unit offers comfortable living in a convenient location close to shopping, restaurants, and Shenandoah University. The apartment features central air, a full-size washer and dryer, and a generous layout with plenty of living space. Step outside to enjoy a private porch, perfect for relaxing, sitting, or

  

  Frank Armstrong, IV

  Colony Realty

  23 Taft Ave Unit 3, Winchester, VA 22601
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  /70

  $535,000

  Sold Jun 05, 2026

  3691 Green Spring Rd, Winchester, VA 22603

  • 4 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Built 1970

  Last Sold Summary

  • 7% Above List Price
  • $332/SF
  • 1 Day On Market

  Current Estimated Value $526,817

  Last Listing Agent Bailey Cooper RE/MAX Gateway

  3691 Green Spring Rd, Winchester, VA 22603
• 

  

  /14

  Est $473,999

  Not Listed For Sale

  2620 Stonegate Dr, Winchester, VA 22601

  • 5 Beds
  • 3 Baths
  • 2,974 Sq Ft
  • Built 1995

  2620 Stonegate Dr, Winchester, VA 22601

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Anthony Adamovich Key Move Properties, LLC.
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  /42

  $289,900

  Under Contract

  • 2 Beds
  • 1 Bath
  • 1,458 Sq Ft

  102 N Purcell Ave, Winchester, VA 22601

  Charming home ideally located just minutes from the heart of historic Winchester! Whether you're looking for convenient access to shopping, dining, entertainment, or commuter routes, this home offers an exceptional location paired with valuable updates for peace of mind. Relax on the inviting covered front porch, the perfect place to enjoy your morning coffee or unwind at the end of the day. The

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  102 N Purcell Ave, Winchester, VA 22601
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  /50

  Starting at $1,722

  Total Monthly Price

  • 2 - 3 Beds

  900-1024 N Braddock St, Winchester, VA 22601

  Welcome to Fort Collier Terrace, an inviting community you'll love being part of. Our apartments in Winchester, VA, come in one, two, and three-bedroom layouts that range from 800 to 1,000 square feet. Aside from the generous living quarters, you'll find everything you need to feel right at home. Located near N Cameron Street and Martinsburg Pike, you're a stone's throw away from the top dining,

  Fort Collier Terrace

  

  900-1024 N Braddock St, Winchester, VA 22601
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  /20

  $388,990

  Sold Jul 29, 2026

  110 Sioux Loop, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • 6% Below List Price
  • $206/SF
  • 35 Days On Market

  D.R. Horton Retreat at Winding Creek - Townhomes

  110 Sioux Loop, Winchester, VA 22602
• 

  

  /68

  Est $652,647

  Not Listed For Sale

  800 Kennedy Dr, Winchester, VA 22601

  • 5 Beds
  • 4 Baths
  • 2,639 Sq Ft
  • Built 2009

  800 Kennedy Dr, Winchester, VA 22601

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Cindy Greenya Keller Williams Realty
• 

  

  /11

  $1,499,000

  • Land
  • 2.45 Acres
  • $611,837 per Acre

  821,829,839, and 851 Fox Dr, Winchester, VA 22603

  Location Location Location! 2.45 Acres comprised of 4 Lots with 3 income producing dwellings. Site falls withing the Frederick County Comprehensive Plan for Commercial Uses. Located just off the Route 37 and Route 522 Interchange next to Sheetz and KFC. All Dwellings and Outbuildings are strictly as-is.

  

  Jim Shebest

  Coldwell Banker Realty

  821,829,839, and 851 Fox Dr, Winchester, VA 22603
• 

  

  /24

  $2,225 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,260 Sq Ft
  • Townhouse for Rent

  312 E Piccadilly St, Winchester, VA 22601

  Freshly updated and just two blocks from the Old Town Pedestrian Mall — this charming downtown duplex is the perfect blend of historic character and modern comfort. Recently renovated, this 3-bedroom, 1.5-bath home features gleaming hardwood floors, beautifully updated tile bathrooms, stainless steel appliances, abundant natural light, and timeless architectural details throughout. Enjoy relaxing

  

  Jeanne Mezzatesta

  Colony Realty

  312 E Piccadilly St, Winchester, VA 22601
• 

  

  /89

  $595,000

  Sold Aug 08, 2025

  121 Carnmore Dr, Winchester, VA 22602

  • 5 Beds
  • 4 Baths
  • 3,086 Sq Ft
  • Built 2005

  Last Sold Summary

  • $193/SF
  • 103 Days On Market

  Current Estimated Value $608,928

  Last Listing Agent Angela Duncan MarketPlace REALTY

  121 Carnmore Dr, Winchester, VA 22602
• 

  

  /34

  Est $604,988

  Not Listed For Sale

  720 Beehive Way, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 2,571 Sq Ft
  • Built 2006

  720 Beehive Way, Winchester, VA 22601

  Last Sold Summary

  • 53 Days On Market

  Last Listing Agent Amy Emerson-Kerns Beltway Realty, LLC.
• 

  

  /23

  $325,000

  $50K PRICE DROP Under Contract

  • 4 Beds
  • 3 Baths
  • 1,916 Sq Ft

  317 N Kent St, Winchester, VA 22601

  Step into a world of timeless elegance and modern luxury with this stunning Colonial residence, beautifully renovated in 2015 while preserving its historic charm. Nestled in a serene setting, this detached home offers a perfect blend of classic architecture and contemporary comforts, making it an ideal retreat for those seeking an exclusive lifestyle. As you enter, you are greeted by rich

  

  Clark Smith

  Samson Properties

  317 N Kent St, Winchester, VA 22601
• 

  

  /44

  Starting at $1,682

  Total Monthly Price

  • 2 - 3 Beds

  121 Fay St, Winchester, VA 22602

  Live on your own terms with Fay Street Apartments. Find the comfort and convenience you crave among our one, two, and three-bedroom residences, on our well-kept premises, and in the nearby, city of Winchester, VA in the Shenandoah Valley. The property is conveniently located near top employers like Shenandoah University and Valley Health System. Our apartments open doors to a myriad of

  Fay Street Apartments

  

  121 Fay St, Winchester, VA 22602
• 

  

  /18

  $644,990

  Sold Sep 04, 2025

  126 Wagtail Ln, Winchester, VA 22603

  • 3 Beds
  • 2 Baths
  • 3,122 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $207/SF
  • 0 Days On Market

  Brookfield Residential Hiatt Pointe at Snowden Bridge - 55+ Single Family Homes Collection

  126 Wagtail Ln, Winchester, VA 22603
• 

  

  /36

  Est $376,994

  Not Listed For Sale

  511 S Kent St, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Built 1900

  511 S Kent St, Winchester, VA 22601

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Lawrence Lessin Homes By Owner, Inc.
• 

  

  /27

  $359,900

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft

  601 Gray Ave, Winchester, VA 22601

  Welcome to Gray Avenue! This beautifully updated 3-bedroom, 2-bath home offers over 1,700 square feet of stylish living space, blending timeless charm with modern finishes throughout. Rich hardwood floors flow throughout the home, creating warmth and character from the moment you step inside. The sun-filled living room feels bright and inviting, highlighted by a custom light fixture and a

  

  Walther Vasquez Johnson

  Samson Properties

  601 Gray Ave, Winchester, VA 22601
• 

  

  /18

  $1,550 Per Month

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

  550 N Loudoun St Unit 1, Winchester, VA 22601

  Beautifully renovated in 2022, this charming 1 bedroom, 1 bathroom apartment is located in historic Winchester and offers updated living with classic character. The apartment features access to a shared coin-operated laundry room located next door at 548 N. Loudoun St. Tenant is responsible for all utilities. Available approximately Jon or before August 14, 2026. Pets are considered on a

  

  Robert Adams

  Weichert Realtors - Blue Ribbon

  550 N Loudoun St Unit 1, Winchester, VA 22601
• 

  

  /15

  $509,990

  Sold Mar 11, 2026

  108 Carnation Way, Winchester, VA 22603

  • 3 Beds
  • 2 Baths
  • 2,050 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $249/SF
  • 9 Days On Market

  Brookfield Residential Hiatt Pointe at Snowden Bridge - 55+ Garden Homes Collection

  108 Carnation Way, Winchester, VA 22603
• 

  

  /47

  Est $530,067

  Not Listed For Sale

  336 Miller St, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,865 Sq Ft
  • Built 1941

  336 Miller St, Winchester, VA 22601

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Julie Teets ERA Oakcrest Realty, Inc.
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  /101

  $879,900

  • 5 Beds
  • 4.5 Baths
  • 3,898 Sq Ft

  243 Summerfield Dr, Winchester, VA 22602

  Immaculate custom home sitting on a half-acre lot in desirable Raven Pointe! Beautiful hardwood floors flow throughout the main level, leading into a dramatic family room with 20-foot ceilings, custom built-ins, a gas fireplace, and high windows featuring remote-controlled custom shades. The gourmet kitchen boasts granite countertops, soft-close cabinets, stainless steel appliances, double wall

  

  Paul Gallagher

  Colony Realty

  243 Summerfield Dr, Winchester, VA 22602
• 

  

  /55

  Starting at $1,795 Plus Fees

  • 1 - 3 Beds

  1981 Randolph Place, Winchester, VA 22601

  Welcome to Stuart Hill Apartments — comfortable living in scenic Winchester, VA. Nestled in the picturesque Shenandoah Valley and just minutes from Historic Downtown Winchester, dining, shopping, Shenandoah University, and Winchester Medical Center, this well-maintained community offers spacious 1-, 2-, and 3-bedroom homes with full-size in-unit washers and dryers, generous closet space, and

  Stuart Hill

  

  1981 Randolph Place, Winchester, VA 22601
• 

  

  /84

  $618,000

  Sold Jun 08, 2026

  891 Payne Rd, Winchester, VA 22603

  • 4 Beds
  • 3.5 Baths
  • 2,849 Sq Ft
  • Built 1973

  Last Sold Summary

  • 12% Below List Price
  • $217/SF
  • 33 Days On Market

  Current Estimated Value $637,257

  Last Listing Agent Angela Duncan MarketPlace REALTY

  891 Payne Rd, Winchester, VA 22603
• 

  

  /28

  Est $285,477

  Not Listed For Sale

  946 Franklin St, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft
  • Built 1955

  946 Franklin St, Winchester, VA 22601

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Stan Dull The Wiley Companies, Inc.
• 

  

  /44

  $360,000

  Open Sun 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,230 Sq Ft

  117 E Pall Mall St, Winchester, VA 22601

  Welcome home to 117 E Pall Mall St! Ideally located within a mile of Shenandoah University and historic downtown Winchester! This 3 bedroom, 2.5 bath has lots of updates and upgrades! Updated kitchen and baths, stainless steel appliances, & a fenced in backyard! 2023 - Roof, siding, & electrical panel (and all breakers), updated kitchen and all baths, 2024 - repaired sump pump & new hot water

  

  Becky Wallace

  Pearson Smith Realty, LLC

  117 E Pall Mall St, Winchester, VA 22601
• 

  

  /12

  $1,500 Per Month

  • 1 Bed
  • 1 Bath
  • 9,518 Sq Ft
  • Condo for Rent

  44 S Loudoun St Unit 7, Winchester, VA 22601

  Historically charming one-bedroom apartment located on the famous downtown walking mall. Enjoy stylish living amongst shops, restaurants, museums, and parks. Only minutes to Winchester Medical Center, Shenandoah University and commuter routes

  

  Brock Harris

  Samson Properties

  44 S Loudoun St Unit 7, Winchester, VA 22601
• 

  

  /11

  $272,900

  Sold Nov 13, 2025

  852 Butler Ave, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,010 Sq Ft
  • Built 1994

  Last Sold Summary

  • $270/SF
  • 5 Days On Market

  Current Estimated Value $294,117

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

  852 Butler Ave, Winchester, VA 22601
• 

  

  /43

  Est $355,327

  Not Listed For Sale

  205 Parkway St, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,008 Sq Ft
  • Built 1971

  205 Parkway St, Winchester, VA 22601

  Last Sold Summary

  • 86 Days On Market

  Last Listing Agent Agustin Martinez Spring Hill Real Estate, LLC.

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