Winchester, VA Homes

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  /15

  $399,480 Pending

  • 3 Beds
  • 4 Baths
  • 1,966 Sq Ft

  103 Marlow Ct, Winchester, VA 22602

  Rossum Crossing is Winchester's newest townhome community, which is located near shopping and dining. The St. Paul Townhome features 3 bedrooms, 2 1/2 baths, and a one-car garage. The main floor has an open-concept floorplan with a spacious family room that leads to a fully equipped kitchen. The kitchen has an island, pantry closet, and breakfast nook. This level also has a powder room. You can

  Dick Bryan New Home Star Virginia, LLC

  103 Marlow Ct, Winchester, VA 22602
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  /58

  $3,500 per month

  • 4 Beds
  • 3 Baths
  • 3,060 Sq Ft
  • House for Rent

  209 N Washington St, Winchester, VA 22601

  Live in the heart of historic Winchester! This beautifully maintained 1853 home on Washington Street offers more than just a place to live—it’s a lifestyle. With over 3,000 square feet of finished space, this one-of-a-kind rental blends timeless character with modern updates just blocks from the Old Town Walking Mall and steps from the Apple Blossom Parade Route.Inside, you’ll find

  Chris Roszko Colony Realty

  209 N Washington St, Winchester, VA 22601
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  /64

  $508,500 Sold Jul 09, 2025

  • 1,830 Sq Ft
  • $278/SF
  • 3 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1972

  1104 Milroy Ct, Winchester, VA 22601

  Step into this beautifully cared-for home featuring gleaming hardwood floors throughout and a spacious, inviting layout. The large kitchen offers plenty of room for meal prep and flows effortlessly into the dining and living rooms — perfect for family gatherings and entertaining.Enjoy the convenience of a sizable laundry room equipped with a front-loading washer and dryer. The finished

  Hailey Mooney Real Broker, LLC

  1104 Milroy Ct, Winchester, VA 22601
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  /31

  Est $276,464 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft

  2964 Grace St, Winchester, VA 22601

  2964 Grace St, Winchester, VA 22601
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  /45

  $409,750 Under Contract

  • 3 Beds
  • 3.5 Baths
  • 2,250 Sq Ft

  149 Biscane Ct, Winchester, VA 22602

  149 Biscane Ct, where fresh design feels effortlessly like home.. This beautifully maintained 2018 townhome shows like new construction! This spacious, light-filled townhome offers three levels of privacy and is ideal for today’s lifestyle. Let me walk you through your new home! When you pull into the garage, the front facing one-car garage features epoxy floors and wall shelving, ideal

  Kara Koonce Weichert, REALTORS

  149 Biscane Ct, Winchester, VA 22602
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  /18

  $1,825 per month

  • 2 Beds
  • 1 Bath
  • 1,113 Sq Ft
  • House for Rent

  513 Battle Ave, Winchester, VA 22601

  Adorable two bedroom one bath home that maintains the charm of its era while being fully move-in ready and within walking distance to Old Town Winchester! Central AC/Heating and cieling fans. Non-Smoking. Original and newly refinished hardwood floors, fully renovated full bath, updated kitchen with charming original cabinetry. New washer and dryer in unit. Located on a generous level lot in

  513 Battle Ave, Winchester, VA 22601
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  /29

  $350,000 Sold Jul 09, 2025

  • 1,200 Sq Ft
  • $292/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  1109 Opequon Ave, Winchester, VA 22601

  This delightful single-level home sits in the heart of vibrant Winchester City. Meticulously updated and maintained, it features an updated kitchen boasting stainless steel appliances (all less than five years old), tasteful subway tile backsplash and classic quartz countertops. Offering three bedrooms, two FULL bathrooms, a living room AND a den, the design and layout can meet all of your

  Stephanie Ryall Realty ONE Group Old Towne

  1109 Opequon Ave, Winchester, VA 22601
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  /26

  Est $301,891 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  2952 Grace St, Winchester, VA 22601

  2952 Grace St, Winchester, VA 22601
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  /45

  $475,000 Under Contract

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

  2620 Stonegate Dr, Winchester, VA 22601

  Contemporary 5-Bedroom Rancher - Prime Winchester LocationDiscover one of Winchester's most coveted addresses – where urban convenience meets serene privacy in this meticulously maintained contemporary rancher. This exceptional 5-bedroom, 3-full-bath home sits on a premium lot backing to Frederick Douglass Elementary School and beautiful parkland, offering privacy with breathtaking sunrise

  Anthony Adamovich Key Move Properties, LLC.

  2620 Stonegate Dr, Winchester, VA 22601
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  /25

  $3,000 per month

  • 4 Beds
  • 3 Baths
  • 2,312 Sq Ft
  • House for Rent

  609 Quartzite Cir, Winchester, VA 22601

  Welcome to 609 Quartzite Circle – a beautifully maintained single-family home available for rent for the first time! This spacious residence features all brand-new appliances, making it move-in ready and perfect for comfortable living. Located in a NO HOA community, you'll enjoy the freedom and privacy that comes with it.The home boasts generously sized rooms, a large backyard ideal for

  Collin Santa Ana Move4Free Realty, LLC

  609 Quartzite Cir, Winchester, VA 22601
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  /57

  $424,000 Sold Jul 08, 2025

  • 1,720 Sq Ft
  • $247/SF
  • 17 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1928

  803 Berryville Ave, Winchester, VA 22601

  Your search ends here...This charming 4 bedroom home is an exquisitely restored 1928 American Four Square, just minutes from Winchester’s Historic District and a commuter’s dream with easy access to Leesburg, Tysons Corner, and the DC Metro area.**This timeless beauty has been *renovated from top to bottom*, blending historic charm with modern luxury. Step through the generous foyer and

  Tanya Spotts Long & Foster Real Estate, Inc.

  803 Berryville Ave, Winchester, VA 22601
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  /25

  Est $380,667 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,147 Sq Ft

  2921 Second St, Winchester, VA 22601

  2921 Second St, Winchester, VA 22601
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  /37

  $450,000 Under Contract

  • 3 Beds
  • 2 Baths

  2824 Broadview St, Winchester, VA 22601

  Welcome to this stunningly new built 3-bedroom beautiful home located in the heart of Winchester. Enjoy the unbeatable convenience of being just moments from shopping Centers, playgrounds, theatres, and more.Step inside to experience the fresh scent of new construction and move-in-ready living, complete with brand new-flooring, modern appliances, and a thoughtfully designed layout perfect for

  Elizabeth Flood Keller Williams Realty

  2824 Broadview St, Winchester, VA 22601
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  /20

  $1,483 - $1,865 per month

  Peppertree VA

  1 - 3 Beds

  221 Peppertree Ln, Winchester, VA 22601

  Tastefully designed 1, 2 and 3 bedroom floor plans and richly landscaped surroundings make for a welcome sight to call your home. Located in the heart of Winchester, Peppertree offers the conveniences of city living in a park-like setting. Peppertree is in close proximity to shopping, restaurants, schools and Winchester Medical Center.

  221 Peppertree Ln, Winchester, VA 22601
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  /19

  $226,000 Sold Jul 03, 2025

  • 1,277 Sq Ft
  • $177/SF
  • 6 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1936

  521 1/2 N Loudoun St, Winchester, VA 22601

  Opportunity knocks in the heart of Winchester! This all-brick charmer sits just steps from downtown and is ready for its next chapter. With a classic front porch, a garage, and timeless architectural details, this home offers the perfect canvas for a full renovation. Whether you're an investor, contractor, or visionary buyer, this is your chance to bring a historic gem back to life in a prime

  Barton Chasler Realty ONE Group Old Towne

  521 1/2 N Loudoun St, Winchester, VA 22601
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  /22

  Est $289,741 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 954 Sq Ft

  313 Summit Ave, Winchester, VA 22601

  313 Summit Ave, Winchester, VA 22601
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  /20

  $499,900

  • Studio
  • 2,376 Sq Ft

  510 N Loudoun St, Winchester, VA 22601

  All brick 3 unit complex with off street parking and near Old Town Mall..2nd floor has 2BD/1BA with unfinished attic, main floor is 1BR/1BA (Both have rear balcony) and basement unit has access to storage area and includes1BD/1BA. All units have washer/dryer (Basement unit washer/dryer belongs to tenant). Owner/Agent and home inspection report available upon request.

  Dave Spence RE/MAX Roots

  510 N Loudoun St, Winchester, VA 22601
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  /16

  $1,599 per month

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Townhouse for Rent

  321 N Pleasant Valley Rd, Winchester, VA 22601

  Welcome to this solid brick 3-bedroom, 1-bath townhome ideally located just minutes from the heart of downtown! Featuring a spacious and sunlit living area, this home offers classic charm with hardwood floors, updated fixtures, and a functional layout perfect for both relaxing and entertaining. The kitchen includes ample cabinet space and opens to a cozy dining area. Upstairs, you'll find three

  Amy Emerson-Kerns Cambridge Premier Realty, LLC.

  321 N Pleasant Valley Rd, Winchester, VA 22601
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  /39

  $365,000 Sold Jul 03, 2025

  • 1,833 Sq Ft
  • $199/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1964

  320 Russellcroft Rd, Winchester, VA 22601

  Lovingly maintained by the same owner for over 50 years, this charming ranch-style home is a true gem! From the moment you arrive, the care and attention to detail are clear — from the circular driveway and manicured lawn to the discreet bin enclosure that keeps trash cans out of sight. Enjoy the ease of main-level living with 3 spacious bedrooms and 2 full baths, including a private ensuite off

  Jeanne Mezzatesta Colony Realty

  320 Russellcroft Rd, Winchester, VA 22601
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  /29

  Est $309,585 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,250 Sq Ft

  2917 First St, Winchester, VA 22601

  2917 First St, Winchester, VA 22601
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  /13

  $349,999 Open Sat 11AM - 3PM

  • 5 Beds
  • 2 Baths
  • 1,584 Sq Ft

  505 Green St, Winchester, VA 22601

  Charming 3-Level Split Home in the Heart of Winchester!This split level home could be your forever home! Surrounded by parks, top-rated schools, and everyday amenities. Quick access to Route 7 and Interstate 81 commuting is breeze! Upstairs, you’ll find three generously sized bedrooms and a full bathroom, offering a peaceful seperate area. The main level boasts a warm and

  Julissa Rodriguez Vaze Realty

  505 Green St, Winchester, VA 22601
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  /9

  $1,800 - $2,600 per month

  Apartment for Rent

  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

  210 S Cameron St, Winchester, VA 22601
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  /48

  $685,000 Sold Jul 03, 2025

  • 4,270 Sq Ft
  • $160/SF
  • 3 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1900

  503 S Washington St, Winchester, VA 22601

  Discover unparalleled charm and historic elegance in this circa 1900 Victorian residence, ideally situated in Winchester's downtown Historic District and on the Apple Blossom parade route. Stunning 5-bedroom,4.5 bathroom home, boasting approximately 4270 sq ft of living space, invites you to experience the grandeur of a bygone era. Off-street parking.Key features include:Historic Charm:

  John Schroth Colony Realty

  503 S Washington St, Winchester, VA 22601
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  /31

  Est $266,848 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 850 Sq Ft

  2944 Second St, Winchester, VA 22601

  2944 Second St, Winchester, VA 22601
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  /12

  $90,000

  • 2 Beds
  • 1 Bath
  • 882 Sq Ft

  222 Liberty Ave, Winchester, VA 22601

  **OFFER DEADLINE OF 2PM ON 8/1**Investor, builder, or renovation enthusiast—this is the opportunity you’ve been waiting for!This 2-bedroom, 1-bath home is a true fixer-upper with serious potential. Whether you’re looking to take on a full gut renovation or tear it down and start from scratch, this property is a blank canvas ready for your vision. With 882 square feet of interior

  Chris Craddock EXP Realty, LLC

  222 Liberty Ave, Winchester, VA 22601
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  /8

  $2,800 per month

  • 4 Beds
  • 3.5 Baths
  • 2,300 Sq Ft
  • House for Rent

  437 W Leicester St, Winchester, VA 22601

  The front porch on this house is the best part of the home. Use it for sitting out on and enjoying the beautiful weather. There is also a back porch in case you need need more privacy. This house has a remodeled 3rd floor Guest Suite. The house has hardwoods throughout and was completely remodeled in 2011 years ago and comes with a gourmet kitchen with cherry cabinets. It comes with 2

  Brandon Pifer Pifer Realty, LLC

  437 W Leicester St, Winchester, VA 22601
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  /30

  $537,000 Sold Jul 03, 2025

  • 2,154 Sq Ft
  • $249/SF
  • 14 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1995

  1412 Magruder Ct, Winchester, VA 22601

  This peaceful property is within minutes of the Old Town Walking Mall, the arts of Shenandoah University , Winchester Little Theater, Museum of the Shenandoah Valley, Winchester Medical Center and shopping.Spacious living room/dining room with gas fireplace joins a sunroom opening to deck surrounded by lush landscaping. The kitchen features an inviting light filled breakfast area

  Kathryn Hallett Long & Foster Real Estate, Inc.

  1412 Magruder Ct, Winchester, VA 22601
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  /28

  Est $287,214 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 975 Sq Ft

  2916 First St, Winchester, VA 22601

  2916 First St, Winchester, VA 22601
• 

  

  /31

  $425,000

  • Studio
  • 1,298 Sq Ft

  815 Woodland Ave, Winchester, VA 22601

  TWO HOMES FOR THE PRICE OF ONE! Welcome to a unique investment or multi-generational living opportunity with two separate homes on one property!Front House (815 Woodland Ave): On-street parking - 1400 Fin Sq FtThis charming 1920s Craftsman-style Cape Cod offers 3 bedrooms and 1 full bathroom, featuring a welcoming large front porch, original hardwood floors, updated electrical systems,

  RoxAnn Grimes RE/MAX Roots

  815 Woodland Ave, Winchester, VA 22601
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  /20

  $1,800 per month

  CEDAR HILL APARTMENTS

  2 - 3 Beds

  2250 Sofia Way, Winchester, VA 22601

  Cedar Hill Apartments offers well-appointed accommodations located in a convenient and relaxing environment. Only minutes away from Route 37, Route 11, and Jubal Early Drive, Cedar Hill apartments offers its tenants easy access to the Winchester Medical Center, Shenandoah University, loads of shopping and restaurants. Interior features include vaulted ceilings, gas fireplace, wood vanity

  2250 Sofia Way, Winchester, VA 22601
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  /57

  $630,000 Sold Jul 03, 2025

  • 2,774 Sq Ft
  • $227/SF
  • 28 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1865

  716 S Washington St, Winchester, VA 22601

  Well-maintained and full of charm, this 2,774 sq ft, 4-bedroom, 3.5-bath home sits on a 1/3-acre lot in the heart of Old Town Winchester—just one block from Handley High School and a short distance to the vibrant Winchester Walking Mall. Built over 150 years ago, this home features original pine floors, a formal living and dining room, a grand marble-tiled foyer, and a dedicated office with

  Lisa Alberti Roberts Realty Group, LLC

  716 S Washington St, Winchester, VA 22601
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  /19

  Est $317,593 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,472 Sq Ft

  2928 First St, Winchester, VA 22601

  2928 First St, Winchester, VA 22601
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  /33

  $299,000

  • 4 Beds
  • 2 Baths
  • 2,058 Sq Ft

  566 N Loudoun St, Winchester, VA 22601

  Welcome to 566 N Loudoun Street, a spacious 4-bedroom, 2-full-bath home offering a fantastic blend of historic appeal and modern potential in Winchester, VA. This property boasts classic hardwood floors throughout and valuable off-street parking, a significant benefit in this area. Enjoy the outdoors with a large covered front porch perfect for relaxing, and a private patio in the rear, all

  Dan Whitacre Colony Realty

  566 N Loudoun St, Winchester, VA 22601
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  /30

  $2,500 per month

  • 4 Beds
  • 2.5 Baths
  • 1,648 Sq Ft
  • House for Rent

  735 Berryville Ave, Winchester, VA 22601

  Welcome to this charming 4-bedroom 2.5 bath home located on the East side of Winchester! Inside, this meticulously maintained home welcomes you in and exudes modern elegance with Open foyer, Gleaming hardwood floors, and Spacious Living spaces, ideal for Entertaining. Sip your morning coffee in the sunny Main level Open Living room or outdoors on the Back patio. At the heart of the home is the

  Rachel Olsen Keller Williams Realty

  735 Berryville Ave, Winchester, VA 22601
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  /54

  $550,000 Sold Jul 02, 2025

  • 2,551 Sq Ft
  • $216/SF
  • 28 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1927

  529 N Braddock St, Winchester, VA 22601

  Priced below appraised value!Welcome home to this charming, light filled Dutch Colonial in the heart of downtown Winchester. With four livable levels, this three bedroom, 2 bath home has been lovingly updated and renovated over the years embracing the charm of a bygone era and offering modern conveniences. Updates include the addition of a dual zone heat pump system (2019) providing cooling

  Dana Cloud Realty ONE Group Old Towne

  529 N Braddock St, Winchester, VA 22601
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  /8

  Est $232,690 Not Listed For Sale

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

  521 Monticello St, Winchester, VA 22601

  521 Monticello St, Winchester, VA 22601
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  /34

  $350,000

  • 3 Beds
  • 2.5 Baths
  • 2,436 Sq Ft

  216 Monticello Square, Winchester, VA 22602

  Step into this beautifully designed 3-level townhome that offers both space and sophistication. With 3 bedrooms, 2.5 baths, and a 1-car garage, this home balances comfort and functionality perfectly. Interior Highlights:An upgraded kitchen featuring modern appliances, stylish cabinetry, and ample counter space—ideal for cooking and entertaining.Not one, but two spacious living areas

  LESLIE WEBB Long & Foster Real Estate, Inc.

  216 Monticello Square, Winchester, VA 22602
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  /14

  $1,550 per month

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft
  • Townhouse for Rent

  30 E Pall Mall St, Winchester, VA 22601

  Charming Rental Home in the Heart of Winchester, VAWelcome to 30 E Pall Mall St, Winchester, VA 22601! This beautifully maintained property offers the perfect blend of modern conveniences and historic charm. Nestled in a prime location, this home is just minutes from downtown Winchester's vibrant restaurants, shops, and entertainment.This home offers plenty of natural light, a

  tiffany pollard Coldwell Banker Elite

  30 E Pall Mall St, Winchester, VA 22601
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  /3

  $271,000 Sold Jul 01, 2025

  • 1,197 Sq Ft
  • $226/SF
  • 23 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1965

  421 Superior Ave, Winchester, VA 22601

  This home is part of an Estate and is being sold as is. Needs a little TLC. Great starter home.Perfectly situated just minutes from shopping, restaurants, and I-81, this property offers convenience without sacrificing its quaint charm. Don't miss out on this genuinely affordable opportunity. Give me a call today to make it yours!

  Cathy Caniford Crossroads, Realtors

  421 Superior Ave, Winchester, VA 22601
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  /71

  Est $375,423 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,600 Sq Ft

  517 Armour Dale, Winchester, VA 22601

  517 Armour Dale, Winchester, VA 22601

Showing Results 121 - 160, Page 4 of 18