Winchester County, VA Homes

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  /32

  $449,000

  • 4 Beds
  • 4.5 Baths
  • 1,913 Sq Ft

  315 National Ave, Winchester, VA 22601

  Fully reimagined for modern living while preserving its timeless charm, this stunning 1910 home in the heart of Downtown Winchester offers the perfect blend of character, luxury, and value. Completely renovated from top to bottom, every detail has been thoughtfully updated—delivering the feel of new construction within a classic architectural setting.This spacious residence features 4

  

  Carlos Soares

  Samson Properties

  (540) 787-2197

  315 National Ave, Winchester, VA 22601
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  /40

  Starting at $1,772

  Total Monthly Price

  • 1 - 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

  (540) 502-3449

  

  900-1024 N Braddock St, 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 $297,567

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

  209 S Braddock St, Winchester, VA 22601
• 

  

  

  /51

  Est $412,444

  Not Listed For Sale

  315 E Piccadilly St, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,409 Sq Ft
  • Built 2015

  315 E Piccadilly St, Winchester, VA 22601

  Last Sold Summary

  • 12 Days On Market
• 

  

  

  /30

  $326,000

  $1K PRICE INCREASE Under Contract

  • 4 Beds
  • 2 Baths
  • 1,273 Sq Ft

  629 National Ave, Winchester, VA 22601

  Beautifully charming and completely move-in ready, this updated 4-bedroom, 2-bath home offers the perfect blend of style, comfort, and functionality. Step inside to find updated flooring and an open-concept main living area designed for today's lifestyle. The heart of the home is the stunning kitchen, featuring granite countertops, white cabinetry, updated fixtures, and a spacious center island

  

  Walther Vasquez Johnson

  Samson Properties

  (540) 889-0898

  629 National Ave, Winchester, VA 22601
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  /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

  (540) 516-3301

  312 E Piccadilly St, Winchester, VA 22601
• 

  

  /22

  $379,900

  Sold Jul 10, 2025

  1806 Kershaw Ln, Winchester, VA 22601

  • 2 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Built 2003

  Last Sold Summary

  • $263/SF
  • 3 Days On Market

  Current Estimated Value $386,496

  Last Listing Agent Dan Whitacre Colony Realty

  1806 Kershaw Ln, Winchester, VA 22601
• 

  

  /25

  Est $518,761

  Not Listed For Sale

  423 W Monmouth St, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 2,296 Sq Ft
  • Built 1963

  423 W Monmouth St, Winchester, VA 22601

  Last Sold Summary

  • 13 Days On Market
• 

  

  /24

  $255,000

  $10K PRICE DROP Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,068 Sq Ft

  103 E Germain St, Winchester, VA 22601

  Welcome home to 103 E Germain St, a rare end-of-row townhouse combining the historic elegance of downtown Winchester with the modern ease of late-80s construction. Whether you are a first-time buyer looking for a move-in ready home or a savvy investor looking for a high-demand rental with excellent yield potential, this property ticks every single box. Flooded with natural light, the main level

  

  Jodi Cilley

  Realty ONE Group Old Towne

  (540) 924-1926

  103 E Germain 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

  (844) 431-3204

  

  2260 Wilson Blvd, Winchester, VA 22601
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  /68

  $635,000

  Sold Aug 01, 2025

  800 Kennedy Dr, Winchester, VA 22601

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

  Last Sold Summary

  • $241/SF
  • 22 Days On Market

  Current Estimated Value $630,995

  Last Listing Agent Cindy Greenya Keller Williams Realty

  800 Kennedy Dr, Winchester, VA 22601
• 

  

  /47

  Est $591,939

  Not Listed For Sale

  134 Omps Dr, Winchester, VA 22601

  • 5 Beds
  • 2.5 Baths
  • 2,478 Sq Ft
  • Built 1992

  134 Omps Dr, Winchester, VA 22601

  Last Sold Summary

  • 0 Days On Market
• 

  

  /65

  $379,900

  $10K PRICE DROP Under Contract

  • 4 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  317 Gray Ave, Winchester, VA 22601

  Welcome to 317 Gray Ave in Winchester, Virginia. This charming Colonial blends historic character with extensive modern updates, creating the perfect balance of vintage appeal and contemporary comfort. The home features 4 bedrooms, 2 full bathrooms, and 1 half bathroom, along with a recently finished attic that offers flexible additional living space. The primary suite includes a beautifully

  

  Matthew Abregu

  Keller Williams Realty

  (540) 701-3590

  317 Gray Ave, Winchester, VA 22601
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  /34

  $1,950 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,369 Sq Ft
  • Townhouse for Rent

  6 E Cecil St, Winchester, VA 22601

  PRICE IMPROVEMENT! Charming Historic 2-Bedroom Rental Just Two Blocks from the Loudoun Street Walking Mall! Live steps from downtown in this beautifully appointed duplex featuring 2-bedrooms and an additional small office/den upstairs. The home is full of historic character and modern comfort, boasting original hardwood floors, soaring ceilings, and timeless architectural charm throughout. A

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 251-7132

  6 E Cecil St, Winchester, VA 22601
• 

  

  /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 $509,591

  Last Listing Agent Dave Spence RE/MAX Roots

  216 Fairmont Ave, Winchester, VA 22601
• 

  

  /47

  Est $426,804

  Not Listed For Sale

  530 Fox Dr, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,351 Sq Ft
  • Built 1955

  530 Fox Dr, Winchester, VA 22601

  Last Sold Summary

  • 9 Days On Market
• 

  

  /13

  $274,999

  • 2 Beds
  • 2.5 Baths
  • 1,080 Sq Ft

  206 Kimberly Way, Winchester, VA 22601

  Beautifully remodeled 2-bedroom, 2.5-bath townhouse that's ready for you to move right in! This home features a stunning updated kitchen with granite countertops and stainless steel appliances, along with modern finishes throughout. Major improvements include a new roof and heat pump installed in 2023, providing added comfort and peace of mind. Spacious living areas, updated bathrooms, and

  

  Frank Armstrong, IV

  Colony Realty

  (540) 516-5187

  206 Kimberly Way, Winchester, VA 22601
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  /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

  (540) 546-5968

  548 Brookfield Dr, Winchester, VA 22601
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  /18

  $330,000

  Sold Jul 28, 2025

  411 N Loudoun St Unit 104, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 1,202 Sq Ft
  • Built 1830

  Last Sold Summary

  • $275/SF
  • 0 Days On Market

  Last Listing Agent Lori Bales Keller Williams Realty

  411 N Loudoun St Unit 104, Winchester, VA 22601
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  /37

  Est $427,192

  Not Listed For Sale

  222 E Piccadilly St, Winchester, VA 22601

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

  222 E Piccadilly St, Winchester, VA 22601

  Last Sold Summary

  • 595 Days On Market
• 

  /2

  $175,000

  • Land
  • 16,117 Sq Ft
  • $472,973 per Acre

  719 Kennedy Dr, Winchester, VA 22601

  Vacant Lot in Rolling HillsOne of the last opportunities to own a vacant lot in the desirable Rolling Hills community. This property offers the perfect setting to build your new home or presents an excellent opportunity for a long-term investment. Enjoy a well-established neighborhood with limited remaining buildable lots. Buyer to verify zoning, utilities, and intended use. Water and Sewer

  

  Frank Armstrong, IV

  Colony Realty

  (540) 709-9357

  719 Kennedy Dr, Winchester, VA 22601
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  /12

  $2,200 Per Month

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  21 S Stewart St Unit 4, Winchester, VA 22601

  Charming Remodeled 2-Bedroom Apartment Near Old Town Winchester!Enjoy the perfect mix of comfort and convenience in this beautifully remodeled 2 bedroom, 2 bathroom apartment located just steps from historic Old Town Winchester. This spacious unit features modern updates, in-unit laundry, and a fully fenced private yard—ideal for relaxing or entertaining. You'll also love the generous storage

  

  Frank Armstrong, IV

  Colony Realty

  (540) 318-1292

  21 S Stewart St Unit 4, Winchester, VA 22601
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  /34

  $412,000

  Sold Jul 23, 2025

  2320 Tower Ave, Winchester, VA 22601

  • 4 Beds
  • 2 Baths
  • 1,762 Sq Ft
  • Built 2006

  Last Sold Summary

  • $234/SF
  • 136 Days On Market

  Current Estimated Value $393,337

  Last Listing Agent Alex Adomako-Acheampong Samson Properties

  2320 Tower Ave, Winchester, VA 22601
• 

  

  /20

  Est $443,377

  Not Listed For Sale

  206 N Kent St, Winchester, VA 22601

  • 2 Beds
  • 4 Baths
  • 2,160 Sq Ft
  • Built 2022

  206 N Kent St, Winchester, VA 22601

  Last Sold Summary

  • 0 Days On Market
• 

  

  /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

  (540) 698-4119

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

  

  /20

  Starting at $1,610 Plus Fees

  • 1 - 2 Beds

  2310 Valor Dr, Winchester, VA 22601

  Harrison Plaza is a new mixed-use development located at the intersection of Hope Drive and Valor Drive in the heart of Winchester, VA. This three-building community offers 70 one- and two-bedroom spacious modern apartments minutes away from local shopping centers, restaurants, and entertainment venues.Interior features include an open floor plan with stylish cabinets, granite countertops,

  HARRISON PLAZA RESIDENTIAL

  (540) 502-3969

  

  2310 Valor Dr, Winchester, VA 22601
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  /71

  $1,025,000

  Sold Aug 01, 2025

  331 N Braddock St, Winchester, VA 22601

  • 5 Beds
  • 6 Baths
  • 6,517 Sq Ft
  • Built 1863

  Last Sold Summary

  • $157/SF
  • 36 Days On Market

  Last Listing Agent John Schroth Colony Realty

  331 N Braddock St, Winchester, VA 22601
• 

  

  /43

  Est $400,369

  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
• 

  

  /40

  $349,000

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

  802 E Cork St, Winchester, VA 22601

  Motivated Seller! Now offering a 3% Buyer's Credit (of sales price)! 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

  Jennifer Egen Samson Properties

  802 E Cork St, Winchester, VA 22601
• 

  

  /13

  $1,500 Per Month

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

  21 S Stewart St Unit 2, Winchester, VA 22601

  2 Bedroom Apartment for Rent – Downtown Winchester Great 2nd-floor apartment located in downtown Winchester with 2 bedrooms and 1 bathroom. This home is just a short walk from Old Town Winchester, giving you easy access to local restaurants, shops, and entertainment. The apartment features very spacious bedrooms, a comfortable family room, and a fully enclosed back porch, perfect for relaxing or

  

  Frank Armstrong, IV

  Colony Realty

  (540) 534-4239

  21 S Stewart St Unit 2, 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 $425,063

  Last Listing Agent James King RE/MAX Roots

  1332 Ramseur Ln, 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
• 

  /2

  $374,990

  New Construction $35K PRICE DROP Pending

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

  221 Monteith Dr, Winchester, VA 22601

  END UNIT Luxury 3 level/3 bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the basement available!***OFFERING UP TO $7K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*MOVE-IN READY! Explore Winchester’s new luxury

  Brittany Newman DRB Group Realty, LLC

  221 Monteith Dr, Winchester, VA 22601
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  /9

  Starting at $1,800 Plus Fees

  • 1 - 2 Beds

  210 S Cameron St, Winchester, VA 22601

  This fully furnished and recently renovated property is located in the heart off Old Town Winchester and includes a log cabin structure, premium appliances, granite countertops and assigned parking spaces.Come and enjoy the excitement of living in Old Town with many excellent restaurants and drinking establishments , six breweries, multiple music venues, fabulous shopping, museums and art

  (540) 486-2865

  210 S Cameron 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 $417,919

  Last Listing Agent Sineenat Sirimas Pearson Smith Realty, LLC

  743 Berryville Ave, Winchester, VA 22601
• 

  

  /49

  Est $422,610

  Not Listed For Sale

  110 W Monmouth St, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft
  • Built 1900

  110 W Monmouth St, Winchester, VA 22601

  Last Sold Summary

  • 30 Days On Market
• 

  

  /12

  $80,000

  • Land
  • 5,662 Sq Ft
  • $615,385 per Acre

  520 Highland Ave, Winchester, VA 22601

  Empty lot ready to build a home one. The lot is fully fenced with front and rear gates. The front of the lot meets the sidewalks and road of Highland Ave. The rear of the lot meets a gravel alley way that could give access to off street parking on this lot. Homes in the city are in demand, so don't miss this opportunity. Zoned HR-1Can only be used for single family dwellingsFront setback:

  Michael Sprague Samson Properties

  520 Highland Ave, Winchester, VA 22601
• 

  

  /8

  $1,600 Per Month

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  619 S Cameron St Unit 1, Winchester, VA 22601

  Charming apartment located in 2 family unit, walking distance to Old Town Winchester. Original hardwood floors, light and bright unit with washer and dryer in unit. Landlord pays water and sewer and tenant pays electric. Shared yard.

  

  Brock Harris

  Samson Properties

  (540) 235-5717

  619 S Cameron 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 $535,270

  Last Listing Agent M. Kelly Walker RE/MAX Roots

  121 N Washington St, Winchester, VA 22601
• 

  /2

  Est $275,891

  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

Showing Results 41 - 80, Page 2 of 18