Winchester County, VA Homes

• 

  

  

  /26

  $364,990

  New Construction $3K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  11 Monteith Dr, Winchester, VA 22601

  3 Level Townhome with Lower Level Bathroom! This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen complete with oversized island seating for four; perfect for entertaining and everyday living. The third level offers conveniently located laundry near the bedrooms for added convenience. Enjoy outdoor living on the 10x16 maintenance-free

  DRB Homes Builder

  11 Monteith Dr, Winchester, VA 22601
• 

  

  

  /10

  $1,395 Per Month

  • 3 Beds
  • 1 Bath
  • 6,578 Sq Ft
  • Townhouse for Rent

  207 E Whitlock Ave, Winchester, VA 22601

  Charming and conveniently located, 207 E Whitlock Avenue in Winchester offers comfortable living just minutes from downtown shops, restaurants, and local attractions. convenient off-street parking. Enjoy easy access to commuter routes, schools, parks, and all that historic Winchester has to offer. Pets considered on a case-by-case basis. No smoking.

  Joseph Clotzman Cambridge Premier Realty, LLC.

  207 E Whitlock Ave, Winchester, VA 22601
• 

  

  

  /35

  $270,000

  Sold Mar 03, 2026

  239 Chestnut St, Winchester, VA 22601

  • 2 Beds
  • 1 Bath
  • 1,176 Sq Ft
  • Built 1976

  Last Sold Summary

  • $230/SF
  • 100 Days On Market

  Current Estimated Value $275,275

  Last Listing Agent William Wertz Wildhawks Realty LLC

  239 Chestnut St, Winchester, VA 22601
• 

  

  

  /15

  Not Listed For Sale

  3142 Eton Place, Winchester, VA 22601

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

  3142 Eton Place, Winchester, VA 22601

  Last Sold Summary

  • 141 Days On Market
• 

  

  

  /48

  $525,000

  $20K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,317 Sq Ft

  938 Wayne Dr, Winchester, VA 22601

  Improved Price!! Welcome to this spacious and well-maintained home in the desirable Meadow Branch South community. Offering over 3,300 square feet, this 4-bedroom, 2.5-bath home provides the perfect blend of space, comfort, and thoughtful updates. The main level features an updated kitchen, ideal for both everyday living and entertaining, along with multiple living areas that offer flexibility

  Kira Grubb Realty ONE Group Old Towne

  938 Wayne Dr, Winchester, VA 22601
• 

  

  /22

  $2,400

  Total Monthly Price

  • 3 Beds
  • 1.5 Baths
  • 1,760 Sq Ft
  • House for Rent

  629 Watson Ave, Winchester, VA 22601

  Enjoy a spacious layout, fenced yard, private rear parking, and a convenient location just minutes from downtown Winchester and major commuter routes. Charming 3BR/1.5BA single-family home in the heart of Winchester featuring approximately 1,760 sq ft of living space. This well-maintained home offers a partially finished basement, a private fenced yard perfect for relaxing or entertaining, and

  629 Watson Ave, Winchester, VA 22601
• 

  

  /40

  $449,990

  Sold Aug 12, 2025

  1827 Reese Ct, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 1,923 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $234/SF
  • 6 Days On Market

  D.R. Horton Abrams Crossing at Meadow Branch

  1827 Reese Ct, Winchester, VA 22601
• 

  

  /22

  Not Listed For Sale

  3146 Eton Place, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,928 Sq Ft
  • Built 2024

  3146 Eton Place, Winchester, VA 22601

  Last Sold Summary

  • 51 Days On Market
• 

  

  /97

  $1,150,000

  $50K PRICE DROP Under Contract

  • 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
• 

  

  /23

  $2,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Condo for Rent

  210 E Boscawen St Unit 200, Winchester, VA 22601

  This two bedroom and two bath apartment has lots of natural light with windows spanning two sides of the building (window treatments already installed). The convenient location is just two blocks from the old town walking mall! Easy to clean and maintain LVP flooring has been installed throughout. The kitchen features ample cabinet space with plenty of drawers for easy organizing, and stainless

  Katie Landi Jordan Samson Properties

  210 E Boscawen St Unit 200, 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 $528,495

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

  2723 Windwood Dr, Winchester, VA 22601
• 

  

  /22

  Not Listed For Sale

  3132 Eton Place, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 2,074 Sq Ft
  • Built 2024

  3132 Eton Place, Winchester, VA 22601

  Last Sold Summary

  • 21 Days On Market
• 

  

  /67

  $549,000

  $21K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 2,450 Sq Ft

  1930 Harvest Dr, Winchester, VA 22601

  Experience the perfect blend of traditional charm and modern scale in this meticulously maintained residence located in the highly sought-after and established community of Meadow Branch South. The striking exterior, framed by a beautifully manicured lawn and mature landscaping, welcomes you into a soaring two-story foyer anchored by gleaming hardwood floors. The main level is designed for

  Dan Whitacre Colony Realty

  1930 Harvest Dr, Winchester, VA 22601
• 

  

  /10

  $1,725

  Total Monthly Price

  • Studio
  • 1 Bath
  • 850 Sq Ft
  • Charming Newly Renovated Down Stairs Apartment in the Heart of Downtown Winchester

  505 N Cameron St, Winchester, VA 22601

  Beautifully renovated upstairs 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
• 

  

  /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 $559,047

  Last Listing Agent Dave Spence RE/MAX Roots

  2307 Stoneridge Rd, Winchester, VA 22601
• 

  

  /41

  Est $480,051

  Not Listed For Sale

  2060 Taylor Grace Ct, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 1,776 Sq Ft
  • Built 2011

  2060 Taylor Grace Ct, Winchester, VA 22601

  Last Sold Summary

  • 22 Days On Market
• 

  

  /28

  $439,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,549 Sq Ft

  320 Virginia Ave, Winchester, VA 22601

  Welcome to 320 Virginia Avenue, where timeless character meets modern sophistication in one of Winchester’s most convenient locations. This beautifully updated home blends historic charm with contemporary finishes, highlighted by designer lighting, exposed brick, custom details, and thoughtful upgrades throughout. From the moment you step inside, the care and craftsmanship are evident. Original

  Cindy Greenya Keller Williams Realty

  320 Virginia Ave, Winchester, VA 22601
• 

  

  /11

  $1,300 Per Month

  • 1 Bed
  • 1 Bath
  • 2,432 Sq Ft
  • Condo for Rent

  506 N Loudoun St Unit 1, Winchester, VA 22601

  Large 1 bedroom 1 bath apartment with rear porch in Historic downtown Winchester, only a few blocks away from the walking mall. Hardwood floors throughout, large kitchen, original wood built-ins, and washer/dryer hookups. Landlord pays gas for heat, water/sewer, and trash. Tenant pays electric.Parking area behind the building or street parking. NVAR OR VAR rental application acceptable or

  Misty Miller OliveTree Property Group, LLC

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

  

  /50

  $465,000

  Sold Jul 10, 2025

  350 Lanny Dr, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 2,371 Sq Ft
  • Built 1967

  Last Sold Summary

  • $196/SF
  • 22 Days On Market

  Current Estimated Value $451,947

  Last Listing Agent Sheila Pack RE/MAX Roots

  350 Lanny Dr, Winchester, VA 22601
• 

  

  /43

  Est $562,708

  Not Listed For Sale

  2044 Taylor Grace Ct, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 3,568 Sq Ft
  • Built 2011

  2044 Taylor Grace Ct, Winchester, VA 22601

  Last Sold Summary

  • 10 Days On Market
• 

  

  /41

  $379,900

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,405 Sq Ft

  1851 Melvor Ln, Winchester, VA 22601

  Extremely well-maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottages 55+ community. This main-level living home features an open floor plan, vaulted ceiling, solar tubes for natural light, and a cozy gas fireplace in the living room. The primary suite offers a private bath, while a bright Florida room provides additional space for relaxing or entertaining. Step outside to

  RoxAnn Grimes RE/MAX Roots

  1851 Melvor Ln, 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
• 

  

  /14

  $460,000

  Sold Aug 07, 2025

  2620 Stonegate Dr, Winchester, VA 22601

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

  Last Sold Summary

  • $155/SF
  • 10 Days On Market

  Current Estimated Value $456,641

  Last Listing Agent Anthony Adamovich Key Move Properties, LLC.

  2620 Stonegate Dr, Winchester, VA 22601
• 

  

  /24

  Est $356,595

  Not Listed For Sale

  456 Imperial St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,722 Sq Ft
  • Built 1962

  456 Imperial St, Winchester, VA 22601

  Last Sold Summary

  • 76 Days On Market
• 

  

  /46

  $1,150,000

  • 5 Beds
  • 5 Baths
  • 5,695 Sq Ft

  801 Armistead St, Winchester, VA 22601

  There are homes that simply provide shelter. And then there are homes like this—homes that make you slow down, take a deep breath, and picture the life you've been working so hard to create. Nestled in one of Winchester's most beloved neighborhoods, this stately residence blends timeless elegance with the confidence that comes from knowing the important work has already been done. Over the past

  Donna Chong Samson Properties

  801 Armistead St, Winchester, VA 22601
• 

  

  /3

  $995 Per Month

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

  1816 Valley Ave Unit 7, Winchester, VA 22601

  We are okay with Short term or Yearly lease. Please contact Property Manager with inquiries.Freshly Remodeled Studio Apartment available. Centered in the heart of Winchester, walking distance to shops, restaurants, and entertainment. Utilities and WIFI are included at no charge. No pets allowed. Come and enjoy all of what Winchester has to offer. $995 per Month or $275 per Week On-site

  Raj Patel Ikon Realty - Ashburn

  1816 Valley Ave Unit 7, Winchester, VA 22601
• 

  

  /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 $416,347

  Last Listing Agent Allyson Lenz Compass

  21 W Pall Mall St, Winchester, VA 22601
• 

  

  /26

  Est $396,731

  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
• 

  

  /7

  $1,100,000

  Under Contract

  • 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
• 

  

  /6

  $1,300

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  506 N Loudoun St Unit 506 N Loudoun St Apt 1, Winchester, VA 22601

  506 N Loudoun St Unit 506 N Loudoun St Apt 1, Winchester, VA 22601
• 

  /2

  $650,000

  Sold Jul 10, 2025

  19 E Boscawen St, Winchester, VA 22601

  • 3 Beds
  • 4 Baths
  • 2,639 Sq Ft
  • Built 1900

  Last Sold Summary

  • $246/SF
  • 79 Days On Market

  Current Estimated Value $497,783

  Last Listing Agent Jen Moore ERA Oakcrest Realty, Inc.

  19 E Boscawen St, Winchester, VA 22601
• 

  

  /24

  Est $420,384

  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
• 

  

  /3

  $425,000

  • 4 Beds
  • 3 Baths
  • 2,157 Sq Ft

  1709 Brandon Dr, Winchester, VA 22601

  Spacious Home in a Prime Location! Discover the potential of this well-built Cape Cod offering generous living spaces and timeless charm. The welcoming living and dining area features a cozy fireplace, creating the perfect setting for gatherings and everyday living. The main level includes a desirable primary suite with a private full bath, an additional bedroom, and a hall bath for added

  Darcy Amburn Colony Realty

  1709 Brandon Dr, Winchester, VA 22601
• 

  

  /13

  $1,900 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.

  Meridee Powars Link Realty Services LLC

  2971 Valley 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 $481,673

  Last Listing Agent Jeanne Mezzatesta Colony Realty

  312 W Cecil St, Winchester, VA 22601
• 

  

  /43

  Est $435,835

  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
• 

  

  /55

  $299,990

  Open Sat 2:30PM - 4:30PM $11K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,474 Sq Ft

  406 Highland Ave, Winchester, VA 22601

  HERE IS YOUR CHANCE! BACK ON THE MARKET DUE TO NO FAULT OF THE SELLERS!!DIRECTIONS FOR PARKING; FROM NAT AVE TAKE RIGHT ON ATHEY ALLY TO 4 CAR PARKING AREA ON LEFT - LOOK FOR 406 MARKER. Located in The Historic Old Town Winchester area with private parking right off of Athey Alley, we are happy to list this nicely remodeled 2 story circa 1930s, center hall home.. Since the purchase of this

  Lisette Turner Century 21 Redwood Realty

  406 Highland Ave, Winchester, VA 22601
• 

  

  /6

  $1,295

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,115 Sq Ft
  • Townhouse for Rent

  307 S Kent St, Winchester, VA 22601

  ** COMING SOON** pictures of similar unit**Charming 2 Bedroom 1 Bath townhouse with full basement for extra storage. Located in the historical district of downtown Winchester. Just a short walk to many of the historical sites, a few blocks from the walking mall and government offices while just a short drive to Winchester Medical Center and Shenandoah University. Pet friendly with approval

  307 S Kent St, Winchester, VA 22601
• 

  

  /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
• 

  

  /39

  Est $390,769

  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

Showing Results 161 - 200, Page 5 of 18