Winchester County, VA Homes

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  /65

  $389,990

  • 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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  /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 areas 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

  (434) 443-7642

  

  230 Spring St, Winchester, VA 22601
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  /57

  $630,000 Sold Jul 03, 2025

  716 S Washington St, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 2,774 Sq Ft
  • Built 1865

  Last Sold Summary

  • $227/SF
  • 28 Days On Market

  Current Estimated Value $626,532

  Last Listing Agent Lisa Alberti Pearson Smith Realty, LLC

  716 S Washington St, Winchester, VA 22601
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  /15

  Not Listed For Sale

  634 Hemsworth Ln, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,916 Sq Ft
  • Built 2025

  634 Hemsworth Ln, Winchester, VA 22601

  Last Sold Summary

  • $203/SF
  • 14 Days On Market

  • Last Sold Price $388,756
  • Apr 30, 2025

  Last Listing Agent Brittany Newman DRB Group Realty, LLC
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  /20

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  514 Cather Ave, Winchester, VA 22601

  Welcome to this home where classic charm meets modern versatility! Built in 1948, this property offers warmth, character, and flexible living spaces designed to fit today’s lifestyle. Step inside to a spacious main level featuring a bright and inviting family room, a dedicated dining area, and an eat-in kitchen—perfect for everyday living and entertaining. This home offers 3–4 bedroom options,

  

  Paula Keiper

  EXP Realty, LLC

  (540) 452-9510

  514 Cather Ave, 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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  /56

  $545,000 Sold Nov 07, 2025

  509 Marion St, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,691 Sq Ft
  • Built 1992

  Last Sold Summary

  • $203/SF
  • 3 Days On Market

  Current Estimated Value $549,774

  Last Listing Agent Mark Francis Real Broker LLC

  509 Marion St, Winchester, VA 22601
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  /40

  Est $309,319 Not Listed For Sale

  1616 S Braddock St, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,610 Sq Ft
  • Built 1956

  1616 S Braddock St, Winchester, VA 22601

  Last Sold Summary

  • 2% Below List Price
  • $196/SF
  • 9 Days On Market

  • Last Sold Price $315,000
  • May 06, 2025

  Last Listing Agent Leah Marabella Realty ONE Group Old Towne
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  /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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  /38

  Starting at $1,873 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

  (540) 502-3204

  

  424 Ridgewood Ln, Winchester, VA 22601
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  /2

  $270,000 Sold Mar 20, 2026

  407 van Fossen St, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 954 Sq Ft
  • Built 1956

  Last Sold Summary

  • 4% Below List Price
  • $283/SF
  • 7 Days On Market

  Current Estimated Value $272,604

  Last Listing Agent Michele Gibson Samson Properties

  407 van Fossen St, Winchester, VA 22601
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  /48

  Est $404,922 Not Listed For Sale

  119 E Germain St, Winchester, VA 22601

  • 2 Beds
  • 2.5 Baths
  • 1,769 Sq Ft
  • Built 1866

  119 E Germain St, Winchester, VA 22601

  Last Sold Summary

  • $229/SF
  • 8 Days On Market

  • Last Sold Price $405,000
  • Apr 29, 2025

  Last Listing Agent Tiffany Hunter ERA Oakcrest Realty, Inc.
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  /6

  $220,000

  • 2 Beds
  • 1.5 Baths
  • 1,064 Sq Ft

  523 Monticello St, Winchester, VA 22601

  Nice duplex. Needs a little updating. Hardwood floors in living room and throughout the 2nd level. Property at this price doesn't include the lot that is being used as part of the yard now. Property can be bought with the lot for $240k Tax id number 330-02-19.Agent related to seller.

  

  Ned Stock

  Berkshire Hathaway HomeServices PenFed Realty

  (540) 660-7920

  523 Monticello St, Winchester, VA 22601
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  /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
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  /48

  $335,200 Sold Jul 25, 2025

  128 Fox Dr, Winchester, VA 22601

  • 4 Beds
  • 3 Baths
  • 2,606 Sq Ft
  • Built 1961

  Last Sold Summary

  • $129/SF
  • 25 Days On Market

  Current Estimated Value $340,253

  Last Listing Agent MJ Frazier Serhant

  128 Fox Dr, Winchester, VA 22601
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  /93

  Est $1,290,259 Not Listed For Sale

  788 Johnston Ct, Winchester, VA 22601

  • 5 Beds
  • 4.5 Baths
  • 8,070 Sq Ft
  • Built 1999

  788 Johnston Ct, Winchester, VA 22601

  Last Sold Summary

  • 2% Above List Price
  • $157/SF
  • 3 Days On Market

  • Last Sold Price $1,265,000
  • Apr 25, 2025

  Last Listing Agent Lisa Thompson Hunt Country Sotheby's International Realty
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  /3

  $435,000 Open Sat 11AM - 12PM

  • 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, plus a versatile bonus room in the basement ideal for a variety of uses. Well-maintained and located in a convenient neighborhood with no HOA.

  

  Carlos Soares

  Samson Properties

  (540) 253-3199

  623 Smithfield Ave, Winchester, VA 22601
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  /46

  Starting at $1,780 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

  (540) 546-6430

  

  1981 Randolph Place, Winchester, VA 22601
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  /25

  $359,990 Sold Feb 17, 2026

  230 Monteith Dr, Winchester, VA 22601

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

  Move in Ready Sold Summary

  • $202/SF
  • 86 Days On Market

  DRB Homes Village at Valor Crossing - Townhomes

  230 Monteith Dr, Winchester, VA 22601
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  /54

  Est $760,249 Not Listed For Sale

  1026 Armistead St, Winchester, VA 22601

  • 5 Beds
  • 4.5 Baths
  • 5,061 Sq Ft
  • Built 2005

  1026 Armistead St, Winchester, VA 22601

  Last Sold Summary

  • 1% Above List Price
  • $148/SF
  • 4 Days On Market

  • Last Sold Price $749,900
  • May 08, 2025

  Last Listing Agent Cary Embury Thomas and Talbot Estate Properties, Inc.
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  /46

  $489,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,698 Sq Ft

  312 W Cecil St, Winchester, VA 22601

  Don’t miss your chance to live on sought-after W. Cecil in this charming, beautifully maintained historic home, just a few blocks from the walking mall. Light-filled and inviting, this home welcomes you with a classic covered front porch and warm hardwood floors that set the tone for the character throughout. The cozy living room features a recently converted gas fireplace, lovely built-ins, and

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 405-6463

  312 W Cecil St, Winchester, VA 22601
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  /2

  $1,350 Per Month

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

  550 N Loudoun St Unit 4, 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 June 14, 2026. Pets are considered on a case-by-case basis with

  

  Robert Adams

  Weichert Realtors - Blue Ribbon

  (540) 503-4407

  550 N Loudoun St Unit 4, Winchester, VA 22601
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  /61

  $580,000 Sold Dec 09, 2025

  553 Bellview Ave, Winchester, VA 22601

  • 5 Beds
  • 2.5 Baths
  • 2,386 Sq Ft
  • Built 1978

  Last Sold Summary

  • $243/SF
  • 2 Days On Market

  Current Estimated Value $575,464

  Last Listing Agent Dan Whitacre Colony Realty

  553 Bellview Ave, Winchester, VA 22601
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  /26

  Est $315,837 Not Listed For Sale

  641 Dunlap St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1978

  641 Dunlap St, Winchester, VA 22601

  Last Sold Summary

  • 1% Below List Price
  • $315/SF
  • 16 Days On Market

  • Last Sold Price $318,000
  • May 05, 2025

  Last Listing Agent Heloisa Amar Samson Properties
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  /30

  $285,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  704 Watson Ave, Winchester, VA 22601

  Beautifully Maintained Bungalow in a Prime Location! SELLER MOTIVATED! This home offers 2 bedrooms and 1 full bath on the main level, showcasing pride of ownership throughout. Ideally located just blocks from shopping, coffee shops, and all the conveniences the city has to offer, this property combines comfort with unbeatable accessibility. Enjoy a spacious eat-in kitchen with plenty of room for

  

  Carlos Soares

  Samson Properties

  (540) 530-4023

  704 Watson Ave, Winchester, VA 22601
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  /50

  Starting at $1,850 Plus Fees

  • 1 - 2 Beds

  151 Hope Dr, Winchester, VA 22601

  This new mixed-use community is centrally located in Winchester with quick access to Routes 522 and I-81. Designed for modern, convenient living, Carl's Corner features three residential buildings and a standalone commercial complex.The community offers 18 one-bedroom and 60 two-bedroom apartments, all within walking distance of shopping centers and just minutes from restaurants and

  CARLS CORNER RESIDENTIAL

  (540) 773-2474

  

  151 Hope Dr, Winchester, VA 22601
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  /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 $549,441

  Last Listing Agent MARIA STRIBLING CENTURY 21 New Millennium

  903 Crestview Terrace, Winchester, VA 22601
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  /9

  Est $189,239 Not Listed For Sale

  326 E Piccadilly St, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 1,066 Sq Ft
  • Built 1922

  326 E Piccadilly St, Winchester, VA 22601

  Last Sold Summary

  • 18% Above List Price
  • $150/SF
  • 4 Days On Market

  • Last Sold Price $160,000
  • Apr 30, 2025

  Last Listing Agent George Johnson Jim Barb Realty Inc.
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  /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

  (540) 530-3068

  821,829,839, and 851 Fox Dr, Winchester, VA 22603
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  /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
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  /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 $287,146

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

  209 S Braddock St, Winchester, VA 22601
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  /80

  Est $435,445 Not Listed For Sale

  526 N Braddock St, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,375 Sq Ft
  • Built 1927

  526 N Braddock St, Winchester, VA 22601

  Last Sold Summary

  • 5% Above List Price
  • $175/SF
  • 5 Days On Market

  • Last Sold Price $415,000
  • May 08, 2025

  Last Listing Agent Leah Clowser RE/MAX
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  /38

  $349,900 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,890 Sq Ft

  113 Christopher Dr, Winchester, VA 22601

  Meticulously maintained 3 bedroom, 1.5 bath home in a convenient in-town Winchester location! This home shows beautifully and features hardwood floors that add warmth and character throughout the main living areas. Spacious bedrooms and updates made over the years make this home functional and livable, while still providing an opportunity to personalize as desired. The partially finished basement

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 318-0527

  113 Christopher Dr, Winchester, VA 22601
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  /50

  Starting at $1,843 Plus Fees

  • 1 - 3 Beds

  1864 Old Jube Square, Winchester, VA 22601

  Weve 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 life.

  The Lofts at Jubal Square

  (540) 837-6802

  

  1864 Old Jube Square, Winchester, VA 22601
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  /25

  $520,000 Sold Jun 19, 2025

  423 W Monmouth St, Winchester, VA 22601

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

  Last Sold Summary

  • $226/SF
  • 13 Days On Market

  Current Estimated Value $519,341

  Last Listing Agent Lindsey Richardson ERA Oakcrest Realty, Inc.

  423 W Monmouth St, Winchester, VA 22601
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  /64

  Est $548,683 Not Listed For Sale

  344 Linden Dr, Winchester, VA 22601

  • 3 Beds
  • 4 Baths
  • 3,360 Sq Ft
  • Built 2007

  344 Linden Dr, Winchester, VA 22601

  Last Sold Summary

  • 4% Above List Price
  • $158/SF
  • 0 Days On Market

  • Last Sold Price $530,000
  • Apr 25, 2025

  Last Listing Agent Jodi Costello ERA Oakcrest Realty, Inc.
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  /3

  $519,900 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 2,879 Sq Ft

  315 Walker St, Winchester, VA 22601

  Beautiful brick split-foyer home tucked away on a quiet dead-end street in the desirable Whittier Acres community. This location is one of Winchester’s best kept secrets! 315 Walker St has nearly 2,900 finished square feet, combining space, flexibility, and a peaceful setting just minutes from Old Town Winchester, Winchester Medical Center, and everyday conveniences. The main level features a

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 698-3569

  315 Walker St, Winchester, VA 22601
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  /10

  $1,700 Per Month

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

  44 S Loudoun St Unit 12, Winchester, VA 22601

  Charming one-bedroom apartment in the heart of historic downtown Winchester! Located right on the Walking Mall, you’ll be surrounded by local shops, restaurants, and entertainment. This inviting apartment features a spacious living room, an updated kitchen with newer cabinets and stainless steel appliances, convenient in-unit laundry, and one assigned parking space in a private lot. Enjoy

  

  Brock Harris

  Samson Properties

  (540) 413-0384

  44 S Loudoun St Unit 12, Winchester, VA 22601
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  /47

  $309,000 Sold Jul 28, 2025

  233 Molden Dr, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 2,348 Sq Ft
  • Built 1950

  Last Sold Summary

  • $132/SF
  • 6 Days On Market

  Current Estimated Value $329,361

  Last Listing Agent Kevin Smith Sager Real Estate

  233 Molden Dr, Winchester, VA 22601
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  /34

  Est $322,007 Not Listed For Sale

  1322 S Kent St, Winchester, VA 22601

  • 2 Beds
  • 2.5 Baths
  • 1,238 Sq Ft
  • Built 2020

  1322 S Kent St, Winchester, VA 22601

  Last Sold Summary

  • 2% Above List Price
  • $254/SF
  • 2 Days On Market

  • Last Sold Price $314,900
  • Apr 30, 2025

  Last Listing Agent Lisa Cox Colony Realty

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