Winchester, VA Homes

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  /21

  $425,000

  • 5 Beds
  • 2 Baths
  • 1,710 Sq Ft

  912 Opequon Ave, Winchester, VA 22601

  Welcome to 912 Opequon Ave- Spacious, Updated & Perfectly Located in Winchester !Opportunity meets versatility in this beautifully updated 5 bedrooms, 2 bath home nestled in one of Winchester most walkable and convenient neighborhoods! Whether you're a homeowner seeking flexible living space or an investor eyeing income potential, this property checks every box . Freshly painted interior

  max cortijo Fairfax Realty of Tysons

  912 Opequon Ave, Winchester, VA 22601
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  /34

  $2,500 per month

  • 4 Beds
  • 3 Baths
  • 2,105 Sq Ft
  • House for Rent

  301 Wood Ave, Winchester, VA 22601

  Welcome to this beautifully maintained home located in the heart of Winchester! Nestled on a quiet street, this residence offers both comfort and convenience—just minutes from Winchester Medical Center, Shenandoah University, and Old Town Winchester.Step inside to find a bright and inviting living space, complemented by hardwood floors and large windows that let in abundant natural

  Bailey Cooper RE/MAX Gateway

  301 Wood Ave, Winchester, VA 22601
• 

  

  

  /22

  $350,000 Sold Jul 21, 2025

  • 1,060 Sq Ft
  • $330/SF
  • 66 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  601 Fairview Ave, Winchester, VA 22601

  Fully Renovated Gem in the Heart of Winchester! Welcome to 601 Fairview Ave, where modern upgrades meet timeless charm! This beautifully remodeled 3-bedroom, 2-bathroom rambler offers the perfect blend of comfort and convenience in one of Winchester’s most desirable locations.Step inside to discover a brand-new kitchen featuring stylish finishes, sleek countertops, and modern

  Jorge Najarro Samson Properties

  601 Fairview Ave, Winchester, VA 22601
• 

  

  

  /39

  Est $370,332 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,747 Sq Ft

  417 Superior Ave, Winchester, VA 22601

  417 Superior Ave, Winchester, VA 22601
• 

  

  

  /40

  $465,000

  • 4 Beds
  • 2 Baths
  • 1,092 Sq Ft

  1709 Reaves St, Winchester, VA 22601

  Please take off shoes and give feedback. Step into this beautifully cared-for home featuring new roof (2023) New HVAC System (2024) new LVP floors throughout the basement 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. The finished basement boasts a

  Alexandra Brown Berkshire Hathaway HomeServices PenFed Realty

  1709 Reaves St, Winchester, VA 22601
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  /15

  $1,500 - $1,550 per month

  Woodstock Terrace

  2 Beds

  1016 Woodstock Ln, Winchester, VA 22601

  Fully furnished apartments! TV, Internet provided!

  1016 Woodstock Ln, Winchester, VA 22601
• 

  

  /39

  $370,000 Sold Jul 18, 2025

  • 1,050 Sq Ft
  • $352/SF
  • 4 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1968

  625 Butler Ave, Winchester, VA 22601

  This house has been remodeled and offers five bedrooms and 2.5 bathrooms. The open concept is evident in the easy-flowing floor plan. Beautiful kitchen quartz countertops, 42-inch cabinets and stainless steel appliances. Freshly painted, tastefully renovated bathrooms, new floors throughout, recess lighting, newer windows, driveway, and garage. Walkout basement with two big bedrooms and a

  Aracely Rivera First Decision Realty LLC

  625 Butler Ave, Winchester, VA 22601
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  /54

  Est $357,385 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,221 Sq Ft

  444 Imperial St, Winchester, VA 22601

  444 Imperial St, Winchester, VA 22601
• 

  

  /48

  $574,900

  • 4 Beds
  • 3.5 Baths
  • 2,602 Sq Ft

  1629 Pondview Dr, Winchester, VA 22601

  Discover tranquility and spacious living in this exceptional 4-bedroom, 3.5-bath home, with a main-level primary suite, ideally situated on one half of an acre backing to picturesque trees and wide-open fields. From the moment you step inside, you'll appreciate the meticulously maintained interior and inviting open floor plan. The living room features a cathedral ceiling and a cozy gas fireplace,

  Kerry & Ed Stinson Berkshire Hathaway HomeServices PenFed Realty

  1629 Pondview Dr, Winchester, VA 22601
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  /14

  $1,750 per month

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

  15 E Piccadilly St Unit 204, Winchester, VA 22601

  "The Monument Lofts" are industrial style loft on the downtown walking mall with masterful design and high-end finishes. Sealed cement floors, high vaulted ceilings, wide open kitchen/living combination, and access to quaint workout facility and storage room make this loft your desired spot for year or years depending on your stay in Winchester! Parking space, Water/Sewer, electronic locks(

  Dave Spence RE/MAX Roots

  15 E Piccadilly St Unit 204, Winchester, VA 22601
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  /48

  $260,000 Sold Jul 18, 2025

  • 1,340 Sq Ft
  • $194/SF
  • 34 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1930

  21 W Pall Mall St, Winchester, VA 22601

  "Bring Your Vision To W Pall Mall" This 4 bedroom, 1 full bath home is perfect if you're looking for a renovation! Right in the heart of Winchester City within walking distance to the Old Town Walking Mall where you can enjoy excellent food, shopping and more! The first floor has a great sized living room, dining room and kitchen. 4 bedrooms on the upper level, full bathroom, walk-up attic and an

  Matt Kilmer EXP Realty, LLC

  21 W Pall Mall St, Winchester, VA 22601
• 

  

  /10

  Est $262,248 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 858 Sq Ft

  420 Royal St, Winchester, VA 22601

  420 Royal St, Winchester, VA 22601
• 

  

  /32

  $499,900

  • 4 Beds
  • 4 Baths
  • 1,627 Sq Ft

  201 Parkway St, Winchester, VA 22601

  Freshly Renovated Charmer in Winchester!Welcome to 201 Parkway Street, a freshly updated home in the heart of Winchester! Previously tenant-occupied, this property has been thoughtfully refreshed and is ready for new owners. Recent Updates Include:Fresh interior paint throughoutRenovated kitchen and bathUpdated fixtures and finishesClean, move-in ready conditionThis home offers the perfect blend

  Cherish Green Coldwell Banker Elite

  201 Parkway St, Winchester, VA 22601
• 

  

  /19

  $1,500 per month

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

  926 Armistead St, Winchester, VA 22601

  926 Armistead St, Winchester, VA 22601
• 

  

  /37

  $399,500 Sold Jul 18, 2025

  • 2,052 Sq Ft
  • $195/SF
  • 22 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2022

  220 E Piccadilly St, Winchester, VA 22601

  Welcome to Piccadilly Circle, a newly built luxury home community located in the heart of Old Town Winchester, VA. A great location within walking distance of over 30 restaurants, 60 shops, and numerous historical sites and museums. Circle residents can also take advantage of nearby community playgrounds and parks. This home is move-in ready!On the main entry level, find Luxury Vinyl

  Jason Aikens RE/MAX Roots

  220 E Piccadilly St, Winchester, VA 22601
• 

  

  /14

  Est $356,822 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,970 Sq Ft

  3128 Papermill Rd, Winchester, VA 22601

  3128 Papermill Rd, Winchester, VA 22601
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  /26

  $499,900 Open Sat 11AM - 1PM

  • 6 Beds
  • 3 Baths
  • 3,900 Sq Ft

  811 Berryville Ave, Winchester, VA 22601

  DO YOU HAVE A LARGE FAMILY AND NEED YOUR OWN SPACE. HERE IS A 6 BEDROOMS 3 BATHROOMS WITH A IN-LAW SUITE. OVER 3900+ SQ. FT FINISHED. OFF STREET PARKING FOR 6 CARS. SHED AND STILL ROOM TO RELAX OUTBACK.

  Richard Kozlowski Long & Foster Real Estate, Inc.

  811 Berryville Ave, Winchester, VA 22601
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  /29

  $1,995 per month

  • 3 Beds
  • 2 Baths
  • 1,755 Sq Ft
  • House for Rent

  204A Bellview Ave, Winchester, VA 22601

  SPACIOUS CAPE COD WITH FENCED BACK YARD. In-town convenience. Near shopping and commuter routes. 3 bedrooms, 2 full baths. Beautiful hardwood floors. Formal living and dining rooms with large picture windows that let in lots of natural light. Eat-in kitchen. Main-level family room with built-in shelves. Full, unfinished basement for storage. Back yard with privacy fence. Outdoor spaces: 20x9

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  204A Bellview Ave, Winchester, VA 22601
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  /40

  $429,900 Sold Jul 17, 2025

  • 2,721 Sq Ft
  • $158/SF
  • 63 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1992

  1324 Ramseur Ln, Winchester, VA 22601

  Elegant Main-Level Condo in The Mews at MeadowbranchWelcome to effortless luxury living in one of Meadowbranch’s most sought-after communities! This stunning main-level condo combines the space and comfort of a single-family home with the convenience and ease of condo living. Bright, open, and beautifully finished, this rare gem in The Mews at Meadowbranch can be yours! Inside,

  Jeanne Mezzatesta Colony Realty

  1324 Ramseur Ln, Winchester, VA 22601
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  /68

  Est $382,893 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,902 Sq Ft

  3020 Papermill Rd, Winchester, VA 22601

  3020 Papermill Rd, Winchester, VA 22601
• 

  

  /17

  $429,855 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  HOMESITE 115 Monteith Dr, Winchester, VA 22601

  *OFFERING UP TO 15K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF PREFERRED LENDER AND TITLE. CONTACT CO LISTING AGENT/CONSULTANT FOR DETAILS* Beautiful open concept living 3 level town home built on concrete slab with a walk-out basement. Finished Rec Room - 13'1" x 11'1" with a door to the outside/backyard. The living room area is 15'3" x 17', open kitchen layout with an

  Brittany Newman DRB Group Realty, LLC

  HOMESITE 115 Monteith Dr, Winchester, VA 22601
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  /10

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • House for Rent

  316 Russelcroft Rd, Winchester, VA 22601

  Relax with the whole family at this peaceful place to stay.Discover your perfect family home-away-from-home! This charming 3-bed, 2-bath house offers stress-free living. Children will love the loft bed! Bikes, scooters, and a piano are available. Enjoy security and privacy in our pet-friendly, fenced-in backyard. Fully furnished for comfort and privacy. Located in a quiet, convenient

  316 Russelcroft Rd, Winchester, VA 22601
• 

  

  /36

  $430,000 Sold Jul 16, 2025

  • 1,830 Sq Ft
  • $235/SF
  • 4 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1998

  325 W Tevis St, Winchester, VA 22601

  Welcome to 325 Tevis St! This charming home is filled with natural light and offers a spacious layout perfect for modern living. The open-concept living and dining areas flow seamlessly, creating an inviting space for both everyday living and entertaining. The generous eat-in kitchen boasts ample cabinet space and is bathed in natural light. Step directly from the kitchen onto

  Danielle Carter Redfin Corporation

  325 W Tevis St, Winchester, VA 22601
• 

  

  /20

  Est $301,531 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 895 Sq Ft

  3113 Papermill Rd, Winchester, VA 22601

  3113 Papermill Rd, Winchester, VA 22601
• 

  

  /6

  $419,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  HOMESITE 114 Monteith Dr, Winchester, VA 22601

  *OFFERING UP TO 15K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF PREFERRED LENDER AND TITLE. CONTACT CO LISTING AGENT/CONSULTANT FOR DETAILS* Late Summer Delivery in Winchester featuring walking trails, lush landscaping multi sport court for basketball and pickleball a welcoming pavilion and tot lot. Bedford II, 3 level townhome features a partial stone front with 1 car

  Brittany Newman DRB Group Realty, LLC

  HOMESITE 114 Monteith Dr, Winchester, VA 22601
• 

  

  /18

  $1,750 per month

  • 2 Beds
  • 1 Bath
  • 1,516 Sq Ft
  • Townhouse for Rent

  303 Gray Ave, Winchester, VA 22601

  Goergeous and fully renovated townhome! Easy walking distance to the downtown Walking Mall. Completely renovated from top to bottom, this home is spacious, bright, and beautiful. The main level is open and airy, with a large living room, a dedicated dining area, and a huge, stunning kitchen. Two huge bedrooms upstairs! Washer and dryer in unit. Private offstreet parking. Background and credit

  Amanda White Nova Home Hunters Realty

  303 Gray Ave, Winchester, VA 22601
• 

  

  /29

  $252,000 Sold Jul 11, 2025

  • 1,024 Sq Ft
  • $246/SF
  • 3 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1992

  2635 Limestone Ct, Winchester, VA 22601

  Move right in with no worries! adorable townhome with granite counters plus Lots of news: April 2023 AC replaced inside and outside, Gas Furnace replaced 2022,Roof replaced 2023,Fence installed 2024, New carpet 2025, newer LVP on main level Appliances a couple years old. 2 bedrooms, 1.5 baths ready for a new owner. Winchester city location near bus routes. Looking for investment property this

  Deborah Matthews ERA Oakcrest Realty, Inc.

  2635 Limestone Ct, Winchester, VA 22601
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  /30

  Est $295,277 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 829 Sq Ft

  3105 Papermill Rd, Winchester, VA 22601

  3105 Papermill Rd, Winchester, VA 22601
• 

  

  /21

  $399,480 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,989 Sq Ft

  117 Boone Ct, Winchester, VA 22602

  Rossum Crossing is Winchester's newest and most popular townhome community, conveniently located near shopping and dining options.The St. Paul Townhome features three bedrooms, two and a half baths, and a one-car garage. The main floor boasts an open-concept floor plan, with a spacious family room that flows into a fully equipped kitchen. The kitchen includes an island, a pantry closet,

  Dick Bryan New Home Star Virginia, LLC

  117 Boone Ct, Winchester, VA 22602
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  /133

  $1,700 per month

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

  342 Fairmont Ave Unit 5 FULLY FURNISHED RENTAL Retro Loves Company, Winchester, VA 22601

  COMPLETELY FURNISHED RENTALPerfect for traveling professionals or students.Furnished one bedroom located behind the beautiful Handley library. This quaint one bedroom apartment is on the 3rd floor of a historic home facing Fairmont Ave. It has terrific views and a spectacular view of fireworks on Apple Blossom, July 4th and New Years Eve. Beautiful details and wainscotting, built in

  342 Fairmont Ave Unit 5 FULLY FURNISHED RENTAL Retro Loves Company, Winchester, VA 22601
• 

  

  /22

  $379,900 Sold Jul 10, 2025

  • 1,442 Sq Ft
  • $263/SF
  • 3 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2003

  1806 Kershaw Ln, Winchester, VA 22601

  Welcome to easy living at 1806 Kershaw Lane! This charming one-level home is perfectly situated in Winchester's desirable 55+ senior community of Willow Lawn Cottages, offering comfort, convenience, and a vibrant lifestyle. Step inside this meticulously maintained residence featuring two spacious bedrooms, two full bathrooms, hardwood floors & vaulted ceilings. The open and inviting floor plan

  Dan Whitacre Colony Realty

  1806 Kershaw Ln, Winchester, VA 22601
• 

  

  /37

  Est $338,346 Not Listed For Sale

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

  2905 First St, Winchester, VA 22601

  2905 First St, Winchester, VA 22601
• 

  

  /21

  $395,985 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,989 Sq Ft

  105 Boone Ct, Winchester, VA 22602

  Rossum Crossing is Winchester's newest and most popular townhome community, conveniently located near shopping and dining options.The St. Paul Townhome features three bedrooms, two and a half baths, and a one-car garage. The main floor boasts an open-concept floor plan, with a spacious family room that flows into a fully equipped kitchen. The kitchen includes an island, a pantry closet,

  Dick Bryan New Home Star Virginia, LLC

  105 Boone Ct, Winchester, VA 22602
• 

  

  /21

  $1,850 per month

  • 3 Beds
  • 1.5 Baths
  • 1,160 Sq Ft
  • House for Rent

  514 Joist Hite Place, Winchester, VA 22601

  Charming Brick Rancher for Rent – Prime Winchester Location!This 3-bedroom, 1.5-bath home offers comfort and convenience just minutes from Winchester’s vibrant Walking Mall. Enjoy a bright, open floor plan with hardwood floors throughout, a cozy living room with fireplace, and a kitchen featuring an island and breakfast bar. The spacious backyard includes a maintenance-free deck and storage

  Mona Botwick Samson Properties

  514 Joist Hite Place, Winchester, VA 22601
• 

  

  /50

  $465,000 Sold Jul 10, 2025

  • 2,371 Sq Ft
  • $196/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1967

  350 Lanny Dr, Winchester, VA 22601

  This beautifully remodeled 3-bedroom, 2-bathroom all-brick rancher is perfectly situated in the heart of Winchester, providing easy access to schools, downtown, Winchester Medical Center, shopping, dining, entertainment, and parks. With its thoughtful remodel, this home blends timeless charm with modern updates. The eat-in kitchen boasts stainless steel appliances (2023), making it perfect for

  Sheila Pack RE/MAX Roots

  350 Lanny Dr, Winchester, VA 22601
• 

  

  /24

  Est $328,095 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  2959 S Pleasant Valley Rd, Winchester, VA 22601

  2959 S Pleasant Valley Rd, Winchester, VA 22601
• 

  

  /44

  $420,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,324 Sq Ft

  567 York Ave, Winchester, VA 22601

  Step into contemporary comfort with this top-to-bottom revamped gem in the heart of Winchester! A welcoming front porch invites you inside to discover sleek matte-black fixtures, new floors, and clean white finishes throughout. The open floor plan effortlessly blends the living room—anchored by a modern built-in fireplace—with a chef-ready kitchen boasting fresh cabinetry, lighting, and stainless

  Mike Webber EXP Realty, LLC

  567 York Ave, Winchester, VA 22601
• 

  

  /25

  $1,700 per month

  • 2 Beds
  • 1 Bath
  • 1,250 Sq Ft
  • Condo for Rent

  21 N Braddock St Unit 4, Winchester, VA 22601

  Hardwood floors throughout historic property, large open rooms, 9' ceilings. 1 of 4 units total in building. Third Floor. No Pets/No Smoking. Large Kitchen features Stove, Microwave, Oven, Full size Fridge -AND a large walk-in pantry (6x10). Rear Entrance inlcludes small patio. Electronic keyed door entry, security cameras on premises. Laundry Room w/ Washer & Dryer in building.

  21 N Braddock St Unit 4, Winchester, VA 22601
• 

  /2

  $650,000 Sold Jul 10, 2025

  • 2,639 Sq Ft
  • $246/SF
  • 79 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1900

  19 E Boscawen St, Winchester, VA 22601

  Property located in the heart of Old Town Winchester. Property is both commercial, and residential, having units available on upper level. Great income property. Currently main level is being leased by restaurant. Upper level is divided into two separate units . Unit one has mudroom, laundry, kitchen, living area/with skylight, and 2 bedrooms. Unit two is an efficiency apartment. Property

  Jen Moore ERA Oakcrest Realty, Inc.

  19 E Boscawen St, Winchester, VA 22601
• 

  

  /40

  Est $288,150 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  2937 Grace St, Winchester, VA 22601

  2937 Grace St, Winchester, VA 22601

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