Winchester County, VA Homes

• 

  

  

  /13

  $274,999

  Under Contract

  • 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

  206 Kimberly Way, Winchester, VA 22601
• 

  

  

  /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
• 

  

  

  /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 $568,567

  Last Listing Agent Mark Francis Real Broker LLC

  509 Marion St, Winchester, VA 22601
• 

  

  

  /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.
• 

  

  /2

  $300,000

  Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,386 Sq Ft

  361 E Piccadilly St, Winchester, VA 22601

  In the heart of Winchester with 3 bedrooms and 1 full bath. Hardwood floors, fresh paint, kitchen with granite countertops, appliances, including full-sized washer and dryer. Lots of storage and private fenced backyard. Close to amenities. You don't want to miss this one!

  

  Stacy Martin

  Keller Williams Realty/Lee Beaver & Assoc.

  361 E Piccadilly St, Winchester, VA 22601
• 

  

  /22

  $2,225 Per Month

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

  314 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

  314 E Piccadilly St, Winchester, VA 22601
• 

  /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 $272,580

  Last Listing Agent Michele Gibson Samson Properties

  407 van Fossen St, Winchester, VA 22601
• 

  

  /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
• 

  /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

  719 Kennedy Dr, Winchester, VA 22601
• 

  

  /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
• 

  

  /25

  $215,000

  Sold May 15, 2026

  212 Shawnee Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 985 Sq Ft
  • Built 1966

  Last Sold Summary

  • 14% Below List Price
  • $218/SF
  • 4 Days On Market

  Current Estimated Value $236,569

  Last Listing Agent Alexander Bracke Real Broker, LLC

  212 Shawnee Ave, Winchester, VA 22601
• 

  

  /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.
• 

  

  /35

  $334,000

  $3K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 1,320 Sq Ft

  124 Worsham Terrace, Winchester, VA 22602

  Welcome to this beautifully maintained townhouse that offers the perfect blend of comfort, style, and convenience. Boasting an attractive full brick-front exterior with classic black shutters, this home offers timeless curb appeal and a welcoming first impression. The private driveway, attached one-car garage, and well-maintained landscaping add both functionality and charm. The main living level

  

  David Peña

  Corcoran McEnearney

  124 Worsham Terrace, Winchester, VA 22602
• 

  

  /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

  44 S Loudoun St Unit 12, Winchester, VA 22601
• 

  

  /74

  $340,000

  Sold May 15, 2026

  707 E Cork St, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • Built 1931

  Last Sold Summary

  • 7% Below List Price
  • $202/SF
  • 6 Days On Market

  Current Estimated Value $345,454

  Last Listing Agent Jaclyn Michelle Berkshire Hathaway HomeServices PenFed Realty

  707 E Cork St, Winchester, VA 22601
• 

  

  /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.
• 

  

  /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
• 

  

  /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
• 

  

  /29

  $369,990

  Sold Apr 28, 2026

  213 Monteith Dr, Winchester, VA 22601

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

  Move in Ready Sold Summary

  • 3% Below List Price
  • $207/SF
  • 40 Days On Market

  DRB Homes Village at Valor Crossing - Townhomes

  213 Monteith Dr, Winchester, VA 22601
• 

  

  /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.
• 

  

  /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
• 

  

  /7

  $1,800 Per Month

  • 1 Bed
  • 1 Bath
  • 2,124 Sq Ft
  • Condo for Rent

  619 S Cameron St Unit 2, 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

  619 S Cameron St Unit 2, Winchester, VA 22601
• 

  

  /13

  $275,000

  Sold Jun 26, 2026

  332 Opequon Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,404 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $196/SF
  • 24 Days On Market

  Current Estimated Value $277,017

  Last Listing Agent Renee Waymire Samson Properties

  332 Opequon Ave, Winchester, VA 22601
• 

  

  /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.
• 

  

  /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 $1,722

  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
• 

  

  /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
• 

  

  /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.
• 

  

  /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
• 

  

  /11

  $1,200 Per Month

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

  44 S Loudoun St Unit 9, Winchester, VA 22601

  Charming 1 bedroom, 1 bathroom apartment located on the Historic Downtown walking mall, with access to all of the Shops, restaurants, museums, and more right out the front door! Just minutes from Shenandoah University, Apple Blossom Mall, and Winchester Medical Center. Parking for each unit.

  

  Brock Harris

  Samson Properties

  44 S Loudoun St Unit 9, Winchester, VA 22601
• 

  

  /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 $595,313

  Last Listing Agent Dan Whitacre Colony Realty

  553 Bellview Ave, Winchester, VA 22601
• 

  

  /71

  Not Listed For Sale

  331 N Braddock St, Winchester, VA 22601

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

  331 N Braddock St, Winchester, VA 22601

  Last Sold Summary

  • 36 Days On Market

  Last Listing Agent John Schroth Colony Realty
• 

  

  /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
• 

  

  /50

  Starting at $1,850 Plus Fees

  • 1 - 2 Beds

  2351 Quinn Ct, 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

  

  2351 Quinn Ct, Winchester, VA 22601
• 

  

  /19

  $275,000

  Sold Jun 30, 2026

  2956 Grace St, Winchester, VA 22601

  • 4 Beds
  • 1 Bath
  • 1,699 Sq Ft
  • Built 1950

  Last Sold Summary

  • 19% Below List Price
  • $162/SF
  • 57 Days On Market

  Current Estimated Value $312,938

  Last Listing Agent Carolyn Young Samson Properties

  2956 Grace St, Winchester, VA 22601
• 

  

  /37

  Est $413,311

  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

  Last Listing Agent Jason Aikens RE/MAX Roots
• 

  

  /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
• 

  

  /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
• 

  

  /37

  $420,000

  Sold Jun 30, 2026

  17 E Leicester St, Winchester, VA 22601

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • Built 1928

  Last Sold Summary

  • $200/SF
  • 196 Days On Market

  Current Estimated Value $414,188

  Last Listing Agent Roger Lamborne MarketPlace REALTY

  17 E Leicester St, Winchester, VA 22601
• 

  

  /20

  Est $375,722

  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

  Last Listing Agent Jason Aikens RE/MAX Roots

Showing Results 1 - 40, Page 1 of 18