Winchester County VA Homes for Sale

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  /5

  $295,000

  Coming Soon Sep 30

  • 3 Beds
  • 1 Bath
  • 913 Sq Ft

  405 Shenandoah Ave, Winchester, VA 22601

  Ideally situated just minutes from I-81 and a short drive to historic Old Town Winchester, this centrally located rambler offers both convenience and investment potential. Situated on a desirable corner lot, the property features a fenced yard and a storage shed for added functionality.The home has been recently refreshed with new paint and landscaping, providing excellent curb appeal and

  Heloisa Amar Samson Properties

  405 Shenandoah Ave, Winchester, VA 22601
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  /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
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  /32

  $399,900

  $29K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,419 Sq Ft

  118 1/2 E Cork St, Winchester, VA 22601

  Seeking the perfect blend of historic character and modern urban living? This exceptional Urban Lofts Condominium is just one and a half blocks from Old Town Winchester Walking Mall, offering easy access to restaurants, boutiques, entertainment, and vibrant downtown living. Originally built in the early 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural

  Janet Flaherty Keller Williams Realty

  118 1/2 E Cork St, Winchester, VA 22601
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  /31

  $265,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,734 Sq Ft

  11 W Germain St, Winchester, VA 22601

  BACK ON THE MARKET -NO FAULT OF THE SELLERS -Step inside this historic home in the heart of Winchester and discover a home that offers far more than you might expect. Generously sized rooms provide plenty of space to relax, or enjoy your favorite hobbies, while a light-filled sunroom creates the perfect spot for morning coffee, reading, plants, or simply slowing down and enjoying the

  Magnolia Halkowitz ERA Oakcrest Realty, Inc.

  11 W Germain St, Winchester, VA 22601
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  /46

  $329,000

  $31K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  307 1/2 E Piccadilly St, Winchester, VA 22601

  Welcome to 307 1/2 E Piccadilly Street, a charming detached home offering comfort, convenience, and character in the heart of Winchester. Ideally located just minutes from Old Town Winchester, the Walking Mall, local restaurants, shopping, parks, and commuter routes, this property places you close to downtown amenities while still offering the privacy and feel of a standalone home. Inside, you’ll

  Nate Crandell HoneyWay

  307 1/2 E Piccadilly St, Winchester, VA 22601
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  /30

  $385,000

  • 3 Beds
  • 1 Bath
  • 1,280 Sq Ft

  540 Bellview Ave, Winchester, VA 22601

  Attention investors! Charming rambler just minutes from historic Old Town Winchester with convenient access to I-81, making commuting simple and stress-free. This inviting home features beautiful hardwood floors, a spacious living room with a cozy fireplace, and a formal dining room perfect for hosting family and friends. The kitchen offers easy access to the backyard, creating a seamless flow

  Heloisa Amar Samson Properties

  540 Bellview Ave, Winchester, VA 22601
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  /37

  $349,900

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,219 Sq Ft

  1856 Melvor Ln, Winchester, VA 22601

  Low-maintenance, one-level living in Winchester! Located on a corner lot in an established 55+ community, 1856 Melvor Lane offers 2 bedrooms, 2 full baths, an open floor plan, and thoughtful updates throughout.Cathedral ceilings and natural light give the main living area an open, airy feel, while luxury vinyl plank flooring extends through most of the home. Fresh interior paint and

  Natasha Roberts Realty ONE Group Old Towne

  1856 Melvor Ln, Winchester, VA 22601
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  /21

  $262,000

  $7K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,280 Sq Ft

  321 N Kent St, Winchester, VA 22601

  Attention investors...24 month lease in place and new HVAC! Wonderful opportunity to own in downtown Winchester! Walking distance to the Old Town Mall restaurants, shopping, the library and more. Easy access to Rt. 7 and 81. The main level has a nice open floor plan, consisting of kitchen, dining and living areas. The main level also features a half bath and bonus room, perfect for an office or

  Amy Capitano MarketPlace REALTY

  321 N Kent St, Winchester, VA 22601
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  /96

  $459,999

  $30K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 1,887 Sq Ft

  419 Summit Ave, Winchester, VA 22601

  Welcome Home! This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and granite countertops in the kitchen, this home combines style and functionality. A new roof adds peace of mind, and the fully finished lower level provides additional living space for relaxation or entertainment. With 5 spacious

  Waqas Abbasi Lifestyle Realty, LLC.

  419 Summit Ave, Winchester, VA 22601
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  /22

  $269,000

  • Land
  • 42,253 Sq Ft
  • $277,320 per Acre

  823 Armistead St, Winchester, VA 22601

  *** Price shown is for lot only. Seller is willing to assist Buyer in building this beautiful home plandesigned by Seller customized for this lot and optimized for cost effective construction. Closingon the lot may occur upon issuance of the Building Permit in Buyer’s name by the City ofWinchester. ***This modern farmhouse style home includes 5,630 square feet of living space

  Janet Flaherty Keller Williams Realty

  823 Armistead St, Winchester, VA 22601
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  /59

  $519,900

  $55K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  660 Beehive Way, Winchester, VA 22601

  Enjoy city living in this spacious and light-filled home featuring 5 bedrooms and 3.5 baths. Fresh new carpeting has been installed on the upper level and in the family room, complemented by hardwood floors throughout the main living areas.The kitchen is equipped with stainless steel appliances, double ovens, and a center island—perfect for cooking and entertaining. Formal living and

  Traci Shoberg Samson Properties

  660 Beehive Way, Winchester, VA 22601
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  /23

  $424,990

  New Construction $5K PRICE INCREASE

  • 4 Beds
  • 3.5 Baths
  • 2,094 Sq Ft

  126 Swansong Place, Winchester, VA 22603

  BUILDER OFFERING BELOW MARKET RATE FINANCING ON THIS MOVE IN READY HOME!!Exceptional value for a 4‑bedroom END‑UNIT townhome is ready for move‑in! Brand‑new construction offers modern style and comfort with oak stairs with upgraded railings and durable LVP flooring throughout the main level. Backing to open space in the newest section of Snowden Bridge, this spacious home includes a flexible

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  126 Swansong Place, Winchester, VA 22603
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  /30

  $379,900

  • 2 Beds
  • 1.5 Baths
  • 1,186 Sq Ft

  711 E Cork St, Winchester, VA 22601

  This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door.

  Marco Novillo Spring Hill Real Estate, LLC.

  711 E Cork St, Winchester, VA 22601
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  /33

  $300,000

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,281 Sq Ft

  115 S Purcell Ave, Winchester, VA 22601

  Price Improvement!!! Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett Park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. New roof installed in 2018.

  Matthew Berry MarketPlace REALTY

  115 S Purcell Ave, Winchester, VA 22601
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  /33

  $447,000

  $3K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,540 Sq Ft

  310 Longview Ave, Winchester, VA 22601

  Discover a stunning blend of Colonial and Contemporary architecture in this exquisite 3-bedroom, 2.5-bathroom residence, built in 2024. Step inside to find luxurious vinyl plank flooring and plush carpeting that exude warmth and sophistication. The gourmet kitchen is a chef's dream, equipped with high-end appliances including a sleek wall oven, cooktop, and energy-efficient refrigerator, ensuring

  Dave Milburn Coldwell Banker Realty

  310 Longview Ave, Winchester, VA 22601
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  /31

  $309,999

  $49K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  608 Dunlap St, Winchester, VA 22601

  Charming 3-bedroom, 1-bath ranch-style home in a highly convenient Winchester location! This well-maintained home is in great condition and has been freshly painted, offering a clean, move-in ready feel. Featuring beautiful hardwood floors throughout and a fully fenced backyard—perfect for pets, entertaining, or relaxing evenings. Central heating and air conditioning for year-round comfort.

  Richard Butcher Coldwell Banker Premier

  608 Dunlap St, Winchester, VA 22601
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  /22

  $599,950

  $25K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,948 Sq Ft

  446 N Loudoun St, Winchester, VA 22601

  Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. The downstairs is a 3-bed/1-bath unit, and the upstairs is a 2-bed/1-bath unit. Separate utilities, with landlord covering water/sewer. Gross income: $44,640 annually, including shed rental. Quality tenants and off-street parking

  Lawrence Lessin Homes By Owner, Inc.

  446 N Loudoun St, Winchester, VA 22601
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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

  821,829,839, and 851 Fox Dr, Winchester, VA 22603
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  /35

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft

  112 W Germain St, Winchester, VA 22601

  100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025!This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic

  Amanda Magana RE/MAX Roots

  112 W Germain St, Winchester, VA 22601
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  /28

  $400,000

  $29K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,432 Sq Ft

  115 E Monmouth St, Winchester, VA 22601

  Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

  Mafe Zambrano Inmobiliaria De Las Casas LLC

  115 E Monmouth St, Winchester, VA 22601
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  /17

  $199,900

  $15K PRICE DROP

  • Land
  • 15,681 Sq Ft
  • $555,278 per Acre

  506 Fairmont Ave, Winchester, VA 22601

  NEW CITY LOT! This newly configured lot in the heart of downtown Winchester has been expanded and is ready for you to build your dream home. Featuring a width of approximately 100 feet, you have plenty of space to accommodate nearly any home of your choice. As a bonus, the driveway will be on the neighboring lot, which allows even more buildable space. Additionally, you do not have to worry about

  Dan Whitacre Colony Realty

  506 Fairmont Ave, Winchester, VA 22601
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  /9

  $689,000

  $611K PRICE DROP

  • Land
  • 64.91 Acres
  • $10,615 per Acre

  Lot 7 Cedar Creek Grade, Winchester, VA

  The seller has made a significant price adjustment to better align the property with current market conditions, creating an outstanding opportunity for buyers. With the new pricing, this property offers exceptional value and is positioned for serious consideration. If you've previously considered this property, now is the time to take another look. Rare opportunity to own 64+ scenic acres on the

  

  Lori Bales

  Keller Williams Realty

  Lot 7 Cedar Creek Grade, Winchester, VA
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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

  719 Kennedy Dr, Winchester, VA 22601
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  /63

  $480,000

  $109K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,974 Sq Ft

  832 Winder Ct, Winchester, VA 22601

  Listed below recent appraised value.All-brick rancher located in the sought-after Early’s Green at Meadow Branch community, offering 1,974 finished square feet with 9-foot ceilings and true one-level living. The open floor plan provides excellent flow and is ideal for both everyday living and entertaining.Recent interior updates include new hardwood flooring in the main living room,

  Barton Chasler Realty ONE Group Old Towne

  832 Winder Ct, Winchester, VA 22601
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  /2

  $199,900

  • Land
  • 6,969 Sq Ft
  • $1,249,375 per Acre

  1415 Ramseur Ln, Winchester, VA 22601

  Steve DuBrueler Coldwell Banker Premier

  1415 Ramseur Ln, Winchester, VA 22601
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  /38

  $449,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  1819 Reese Ct, Winchester, VA 22601

  1819 Reese Court is a move-in ready 3-level townhome with full brick front in Winchester, VA. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained oak stairs lead you to the main level with LVP flooring. The kitchen is equipped with beautiful quartz countertops, sasparilla cabinets, and stainless-steel appliances. The upper

  D.R. Horton Builder

  1819 Reese Ct, Winchester, VA 22601
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  /26

  $354,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,655 Sq Ft

  Adams Plan at Abrams Crossing at Meadow Branch, Winchester, VA 22601

  The Adams I townhome offers 1,889 sq. ft. of thoughtfully designed living space, featuring 4 bedrooms, 3.5 bathrooms, and a convenient 1-car front-load garage. The modern kitchen showcases quartz countertops, stainless steel appliances, a spacious island, recessed lighting, and upgraded cabinets. Enjoy the flexibility of a finished lower-level bonus space-perfect for a rec room, home office, or

  D.R. Horton Builder

  1831 Reese Ct Unit 37025140, Winchester, VA 22601
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  /10

  $399,000

  • Land
  • 3,920 Sq Ft
  • $4,433,333 per Acre

  1 N Braddock St, Winchester, VA 22601

  Make Offer! Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and

  Gillian Greenfield Coldwell Banker Premier

  1 N Braddock St, Winchester, VA 22601

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