Winchester County, VA Homes

• 

  

  

  /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
• 

  

  

  /50

  Starting at $1,889 Plus Fees

  • 1 - 3 Beds

  1864 Old Jube Square, Winchester, VA 22601

  We've got it all at the Lofts at Jubal Square, the newest addition to the charming andhistoric Winchester cityscape. We offer a total commitment to better living, boasting largeapartments with loft and garage options, as well as amenities ideal for all those seeking anexceptional apartment lifestyle. Discover the Lofts at Jubal Square and discover what itmeans to live the good

  The Lofts at Jubal Square

  

  1864 Old Jube Square, Winchester, VA 22601
• 

  

  

  /73

  $497,000

  Sold Aug 25, 2025

  903 Crestview Terrace, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 3,204 Sq Ft
  • Built 2006

  Last Sold Summary

  • $155/SF
  • 64 Days On Market

  Current Estimated Value $580,372

  Last Listing Agent MARIA STRIBLING CENTURY 21 New Millennium

  903 Crestview Terrace, Winchester, VA 22601
• 

  

  

  /43

  Est $392,749

  Not Listed For Sale

  230 Chestnut St, Winchester, VA 22601

  • Studio
  • 1,238 Sq Ft
  • Built 1951

  230 Chestnut St, Winchester, VA 22601

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Jeff Boppe Long & Foster Real Estate, Inc.
• 

  

  

  /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
• 

  

  /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
• 

  

  /23

  $270,000

  Sold Sep 24, 2025

  209 S Braddock St, Winchester, VA 22601

  • 2 Beds
  • 2 Baths
  • 1,446 Sq Ft
  • Built 1900

  Last Sold Summary

  • $187/SF
  • 52 Days On Market

  Current Estimated Value $295,820

  Last Listing Agent Ela Moyer Long & Foster Real Estate, Inc.

  209 S Braddock St, Winchester, VA 22601
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  /36

  Not Listed For Sale

  912 S Braddock St, Winchester, VA 22601

  • Studio
  • 3,790 Sq Ft
  • Built 1946

  912 S Braddock St, Winchester, VA 22601

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Daniel Langberg Washington International Service Executives, 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
• 

  

  /22

  Starting at $1,495

  Total Monthly Price

  • 2 - 4 Beds

  2260 Wilson Blvd, Winchester, VA 22601

  Discover the perfect blend of comfort and convenience at Blue Ridge Apartments in Winchester, VA. Our recently updated homes feature a variety of floor plans. Nestled in a pet-friendly community, you're just minutes away from Winchester's scenic spots, historic downtown, Apple Blossom Mall, and major employers. With easy access to I-81 and Route 7, the best of Winchester is always within reach.

  Blue Ridge Apartments

  

  2260 Wilson Blvd, Winchester, VA 22601
• 

  

  /47

  $335,000

  Sold Jul 28, 2026

  517 Dunlap St, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,366 Sq Ft
  • Built 1941

  Last Sold Summary

  • 9% Below List Price
  • $245/SF
  • 45 Days On Market

  Current Estimated Value $335,259

  Last Listing Agent Carolyn Young Samson Properties

  517 Dunlap St, Winchester, VA 22601
• 

  /2

  Est $273,448

  Not Listed For Sale

  127 S Euclid Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1920

  127 S Euclid Ave, Winchester, VA 22601

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Ned Stock Berkshire Hathaway HomeServices PenFed Realty
• 

  

  /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
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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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  /47

  $512,000

  Sold Feb 27, 2026

  216 Fairmont Ave, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 2,177 Sq Ft
  • Built 1911

  Last Sold Summary

  • $235/SF
  • 81 Days On Market

  Current Estimated Value $551,338

  Last Listing Agent Dave Spence RE/MAX Roots

  216 Fairmont Ave, Winchester, VA 22601
• 

  

  /19

  Est $375,564

  Not Listed For Sale

  204 N Kent St, Winchester, VA 22601

  • 2 Beds
  • 4 Baths
  • 2,052 Sq Ft
  • Built 2022

  204 N Kent St, Winchester, VA 22601

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent Jason Aikens RE/MAX Roots
• 

  

  /22

  $949,000

  New Construction Under Contract

  • 4 Beds
  • 3.5 Baths
  • 2,546 Sq Ft

  0 Oak Ridge Ln Unit VAFV2039728, Winchester, VA 22602

  TO BE BUILT: Fauver and Browning Homes proudly presents The Tremont House—a masterfully designed modern residence that blurs the line between architecture and nature. Thoughtfully crafted to harmonize with its surroundings, this home offers a calm, refined living experience. Tucked at the end of a private cul-de-sac in desirable Fairway Estates, overlooking Winchester Country Club, the design

  

  Jeanne Mezzatesta

  Colony Realty

  0 Oak Ridge Ln Unit VAFV2039728, Winchester, VA 22602
• 

  

  /17

  Starting at $500 Plus Fees

  • 1 - 2 Beds

  548 Brookfield Dr, Winchester, VA 22601

  We are excited to share that we are under new ownership and management, and we're eager to welcome new guests to our community.Located at 500 Brookfield Drive, Winchester, VA 22601, Brookfield Corporate Apartments offers spacious, fully furnished one and two-bedroom apartments. Each apartment is designed with your comfort in mind and comes equipped with linens, kitchenware, two TVs with

  Brookfield Corporate Apartments

  548 Brookfield Dr, Winchester, VA 22601
• 

  

  /29

  $374,990

  Sold Jun 02, 2026

  221 Monteith Dr, Winchester, VA 22601

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • 9% Below List Price
  • $210/SF
  • 87 Days On Market

  DRB Homes Village at Valor Crossing - Townhomes

  221 Monteith Dr, Winchester, VA 22601
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  /37

  Not Listed For Sale

  216 E Piccadilly St, Winchester, VA 22601

  • 3 Beds
  • 3.5 Baths
  • 2,052 Sq Ft
  • Built 2022

  216 E Piccadilly St, Winchester, VA 22601

  Last Sold Summary

  • 651 Days On Market

  Last Listing Agent Jason Aikens RE/MAX Roots
• 

  

  /34

  $524,900

  • 3 Beds
  • 3.5 Baths
  • 3,021 Sq Ft

  1352 Ramseur Ln, Winchester, VA 22601

  Welcome to this beautifully maintained townhome in the desirable Meadowbranch Mews community, where comfort, style, and convenience come together. Featuring three bedrooms and three-and-a-half bathrooms, this brick-front home offers timeless curb appeal and thoughtfully designed living spaces throughout. Step inside to a welcoming foyer with tile flooring that leads to an open and inviting main

  Melissa Donnelly Redfin Corporation

  1352 Ramseur Ln, Winchester, VA 22601
• 

  

  /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
• 

  

  /43

  $410,000

  Sold Apr 20, 2026

  1332 Ramseur Ln, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 2,648 Sq Ft
  • Built 1994

  Last Sold Summary

  • 4% Below List Price
  • $155/SF
  • 16 Days On Market

  Current Estimated Value $414,253

  Last Listing Agent James King RE/MAX Roots

  1332 Ramseur Ln, Winchester, VA 22601
• 

  

  /5

  Not Listed For Sale

  378 National Ave, Winchester, VA 22601

  • Studio
  • 3,032 Sq Ft
  • Built 1910

  378 National Ave, Winchester, VA 22601

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Bill Nordman Commercial Specialists
• 

  

  /46

  $435,000

  Open House 8/16

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  338 Lanny Dr, Winchester, VA 22601

  Come home to Whittier Acres and this well maintained Rancher with 1-car garage just minutes from Winchester Medical Center. You'll love the cozy living room with wood burning fireplace, crown molding & built in bookshelves. Gleaming hardwood floors grace the main level (just refinished). The kitchen has a French door refrigerator, electric range, built-in microwave, dishwasher, a built-in spice

  Gina Chatham Century 21 Redwood Realty

  338 Lanny Dr, Winchester, VA 22601
• 

  /2

  Starting at $1,600 Plus Fees

  • 1 - 2 Beds

  148 N Loudoun St, Winchester, VA 22601

  Beautiful 1 and 2 bedroom fully furnished apartments. Located directly on the old town walking mall. Washer dryer included in the unit. On site parking.

  148 N Loudoun St, Winchester, VA 22601
• 

  

  /56

  $425,000

  Sold Jun 15, 2026

  743 Berryville Ave, Winchester, VA 22601

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1934

  Last Sold Summary

  • 3% Below List Price
  • $304/SF
  • 56 Days On Market

  Current Estimated Value $419,990

  Last Listing Agent Sineenat Sirimas Pearson Smith Realty, LLC

  743 Berryville Ave, Winchester, VA 22601
• 

  

  /37

  Est $410,716

  Not Listed For Sale

  204 E Piccadilly St, Winchester, VA 22601

  • 3 Beds
  • 3.5 Baths
  • 2,052 Sq Ft
  • Built 2022

  204 E Piccadilly St, Winchester, VA 22601

  Last Sold Summary

  • 741 Days On Market

  Last Listing Agent Jason Aikens RE/MAX Roots
• 

  

  /40

  $309,000

  $40K PRICE DROP Pending

  • 4 Beds
  • 2 Baths
  • 1,996 Sq Ft

  802 E Cork St, Winchester, VA 22601

  Motivated Seller! Check out the Virtual Tour! Rich with character and steeped in history, this spacious vintage home sits proudly on a corner lot, offering timeless appeal with many original features still intact. From the moment you enter, you’ll appreciate the craftsmanship of a bygone era—complete with built-in bookshelves, a charming upper-level sleeping porch, and a traditional canning

  Jennifer Egen Samson Properties

  802 E Cork St, 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
• 

  

  /60

  $529,000

  Sold Dec 04, 2025

  121 N Washington St, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 3,100 Sq Ft
  • Built 1807

  Last Sold Summary

  • $171/SF
  • 69 Days On Market

  Current Estimated Value $567,305

  Last Listing Agent M. Kelly Walker RE/MAX Roots

  121 N Washington St, Winchester, VA 22601
• 

  

  /14

  Not Listed For Sale

  611 Laurelwood Cir, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,442 Sq Ft

  611 Laurelwood Cir, Winchester, VA 22601

  Last Sold Summary

  • 28 Days On Market
• 

  

  /23

  $127,750

  • Land
  • 8.11 Acres
  • $15,752 per Acre

  0 Wolf Spring Trail Unit LotWP001, Winchester, VA 22602

  Rare opportunity to own three adjoining fully wooded parcels in the quiet and peaceful Shawneeland community. Numerous residential and recreational possibilities exist with ownership of these tracts. Located just a few miles west of Winchester in the Rosenberger area of the county. Access is secured via extensive road frontage on paved Wolf Spring Trail. Utilities are close by, making for easy

  Chad Pangle Whitetail Properties Real Estate

  0 Wolf Spring Trail Unit LotWP001, Winchester, VA 22602
• 

  

  /20

  Starting at $1,700 Plus Fees

  • Studio - 2 Beds

  114 N Loudoun St, Winchester, VA 22601

  Brand new fully furnished extended stay apartments in the heart of Old Town Winchester Virginia including all utilities, washer /dyer, high speed internet, free nightly and weekend parking ( 5pm to 8 am), keyless entry, 10' ceilings, exposed brick interior partitions and optional weekly cleaning.. More information can be found at themerchantsuites

  The Merchant Suites at 114 North Loudoun

  114 N Loudoun St, Winchester, VA 22601
• 

  

  /49

  $675,000

  Sold Apr 20, 2026

  200 & 210 W Fairfax Ln, Winchester, VA 22601

  • 5 Beds
  • 3.5 Baths
  • 3,294 Sq Ft
  • Built 1928

  Last Sold Summary

  • $205/SF
  • 3 Days On Market

  Last Listing Agent John Schroth Colony Realty

  200 & 210 W Fairfax Ln, Winchester, VA 22601
• 

  

  /39

  Not Listed For Sale

  320 Russellcroft Rd, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,833 Sq Ft
  • Built 1964

  320 Russellcroft Rd, Winchester, VA 22601

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Jeanne Mezzatesta Colony Realty
• 

  

  /22

  $269,000

  • Land
  • 42,253 Sq Ft
  • $277,320 per Acre

  823 Armistead St, Winchester, VA 22601

  *** Price shown is for lot only. Seller is willing to assist Buyer in building this beautiful home plandesigned by Seller customized for this lot and optimized for cost effective construction. Closingon the lot may occur upon issuance of the Building Permit in Buyer’s name by the City ofWinchester. ***This modern farmhouse style home includes 5,630 square feet of living space

  Janet Flaherty Keller Williams Realty

  823 Armistead 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
• 

  

  /43

  $385,000

  Sold Feb 13, 2026

  420 Russelcroft Rd, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,580 Sq Ft
  • Built 1996

  Last Sold Summary

  • 4% Below List Price
  • $244/SF
  • 26 Days On Market

  Current Estimated Value $409,080

  Last Listing Agent Brian Yoder Realty ONE Group Old Towne

  420 Russelcroft Rd, Winchester, VA 22601
• 

  

  /22

  Not Listed For Sale

  3144 Eton Place, Winchester, VA 22601

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

  3144 Eton Place, Winchester, VA 22601

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Brittany Newman DRB Group Realty, LLC

Showing Results 41 - 80, Page 2 of 18