Winchester, VA Homes for Sale

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  /17

  $339,000 Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,699 Sq Ft

  2956 Grace St, Winchester, VA 22601

  Welcome to 2956 Grace Street — a 3-bedroom, 1-bath ranch-style home offering comfortable single-level living in Winchester, where a simple, functional layout and everyday ease come together. Inside, the home opens to a light-filled living area with hardwood floors that add warmth and character, creating a comfortable place to gather or unwind at the end of the day. The kitchen offers workspace

  Carolyn Young Samson Properties

  2956 Grace St, Winchester, VA 22601
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  /67

  $375,000

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

  707 E Cork St, Winchester, VA 22601

  Make an offer! Don't let this location fool you - Plenty of parking on the side and back of the home and a large turn around space to exit onto Cork St easily! Centrally located colonial with gorgeous hardwood flooring and trim throughout! Step back in time, but enjoy all of the modern amenities with easy access to Jim Barnett Park just down the street, downtown walking mall and commuter roads,

  Misty Weaver Samson Properties

  707 E Cork St, Winchester, VA 22601
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  /37

  $430,000

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

  17 E Leicester St, Winchester, VA 22601

  LOWER INTEREST RATE FOR YOU.....Sellers are offering you 2 percent of sales price so you can buy down your interest rate with an initial 2/1 interest rate buydown OR use the 2% seller concession for your closing costs on this classic brick “American Foursquare” house in Winchester’s historic district. This very well maintained 1928 home was designed and built by “ole time” craftsmen who had an

  Roger Lamborne MarketPlace REALTY

  17 E Leicester St, Winchester, VA 22601
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  /2

  $400,000 Coming Soon

  • 5 Beds
  • 2 Baths
  • 1,011 Sq Ft

  605 Dunlap St, Winchester, VA 22601

  Perfectly home on a quiet lot embraced by mature, stately trees, this 5-bedroom, 2 full-bathroom home offers both seclusion and incredible proximity to Winchester's finest amenities, schools, shopping, and major commuter routes. This residence has been completely reimagined, blending the enduring strength, high-end modern finishes. The moment you enter, you are greeted by the seamless flow of

  Alexandra Brown Spring Hill Real Estate, LLC.

  605 Dunlap St, Winchester, VA 22601
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  /6

  $200,000

  • Land
  • 5 Acres
  • $40,000 per Acre

  Lot B Cather Ln, Winchester, VA 22602

  Looking for the perfect spot to build your dream home? This 5-acre parcel of pasture land offers stunning views and an unbeatable location just minutes from town. With a 4-bedroom alternative septic certification letter already in place and minimal covenants and restrictions, you’ll have the freedom to create the home and lifestyle you’ve been envisioning. Local builder recommendations available.

  Kaitlyn Behr Samson Properties

  Lot B Cather Ln, Winchester, VA 22602
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  /13

  $85,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  108 Dwayne Place Unit A135, Winchester, VA 22603

  Welcome to Regency Lakes a all age active and vibrant community, where you can find yourself in your dream home. We have a beautiful, well maintained 1995 3 bed, 2 bath home featuring 1512.00 sq ft of beautifully designed living space, New carpeting throughout, and new garden tub. Located Winchester, this property offers the perfect blend of modern amenities and timeless charm. Step inside to

  Kristina Kelly Regency Lakes

  108 Dwayne Place Unit A135, Winchester, VA 22603
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  /30

  $389,990 New Construction

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

  221 Monteith Dr, Winchester, VA 22601

  END OF ROW Luxury 3 level/3-bedroom townhome with 1 car garage located in the heart of Winchester! MOVE-IN READY! Explore Winchester’s new luxury townhome community. This three level end unit home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with an extended

  DRB Homes Builder

  221 Monteith Dr, Winchester, VA 22601
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  /11

  $4,000,000

  • Land
  • 19 Acres
  • $210,526 per Acre

  368 Victory Rd, Winchester, VA 22602

  19 Acres, Prime Commercial or FLEX Development Opportunity! Zoned B2, General Commercial. Major commuter corridor to Northern VA, adjacent to Airport Business Park, FBI Records Center, Navy Federal Credit Union headquarters, and new One Logistics Park. Also #1 commuter route to Northern VA! Excellent visibility, flat topo, and dual access on Victory Lane and Independence! Sale includes 14.06

  Gillian Greenfield Coldwell Banker Premier

  368 Victory Rd, Winchester, VA 22602
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  /56

  $439,000

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  743 Berryville Ave, Winchester, VA 22601

  Welcome to 743 Berryville Ave in the heart of Downtown Winchester! This unique and versatile property offers exceptional space and flexibility with two fully equipped living areas on one lot.The main house features 4 bedrooms, 2 full bathrooms, 2 kitchens, and 2 laundry areas—ideal for multi-generational living or added convenience. Enjoy a spacious layout with plenty of room for everyone to

  Sineenat Sirimas Pearson Smith Realty, LLC

  743 Berryville Ave, Winchester, VA 22601
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  /11

  $130,000

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  107 Lisa's Dr Unit A172, Winchester, VA 22603

  Welcome to Regency Lakes a vibrant all-age community, where you can find yourself in your dream home. We 1995 3 bed, 2 bath home, completely renovated in 2024 for sale featuring 1568.00 sq ft of beautifully designed living space. Located in/near Winchester, this property offers the perfect blend of modern amenities and timeless charm. Step inside to find everything has been completely renovated.

  Kristina Kelly Regency Lakes

  107 Lisa's Dr Unit A172, Winchester, VA 22603
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  /39

  $539,990 New Construction

  • 6 Beds
  • 4 Baths
  • 3,127 Sq Ft

  HAYDEN Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

  The Hayden is a two-story plan with 6 bedrooms and 3 bathrooms in over 3,100 total square feet. The main level features a flex room adjacent to the foyer, ideal for a formal dining room or home office. The gourmet kitchen has an oversized island for extra seating and a large pantry, and it opens to the dining area and a spacious living room. A bedroom with a full bathroom completes the main

  D.R. Horton Builder

  137 Seminole Dr Unit 36203781, Winchester, VA 22602
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  /51

  $369,900

  • 3 Beds
  • 2 Baths
  • 1,552 Sq Ft

  109 Huron Trail, Winchester, VA 22602

  Discover this inviting 3-bedroom, 2-bath tri‐level home, offering flexible living spaces and a unique layout designed for comfort and creativity. The main level features a bright kitchen and a welcoming living room, setting the tone for easy everyday living. The upper-level hosts three full bedrooms, including a comfortable primary suite with its own ensuite bath, along with a well‐appointed full

  LESLIE WEBB Long & Foster Real Estate, Inc.

  109 Huron Trail, Winchester, VA 22602
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  /36

  $529,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,415 Sq Ft

  ELM Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

  Introducing the Elm, a contemporary 2,415 square feet two-story home, featuring five bedrooms, three bathrooms, a loft, and a two-car garage. As you step into the distinct foyer you will appreciate the open concept floorplan. The spacious kitchen boasts an abundance of cabinetry and counter space, an ample walk-in pantry, a large island with room for seating and stainless-steel appliances. The

  D.R. Horton Builder

  137 Seminole Dr Unit 36203780, Winchester, VA 22602
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  /74

  $450,000

  • 3 Beds
  • 3 Baths
  • 2,860 Sq Ft

  320 Shawnee Trail, Winchester, VA 22602

  Welcome to your very own treehouse retreat surrounded by mature trees, mountain views, and exceptional privacy on 1.86 acres with a Private POOL! This property is designed for outdoor living, featuring a covered front porch, a large back deck with scenic views, and a beautifully crafted stone patio with a fire pit—perfect for entertaining or relaxing under the stars. The private pool area offers

  Stacey Mullins ERA Oakcrest Realty, Inc.

  320 Shawnee Trail, Winchester, VA 22602
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  /54

  $650,490 New Construction

  • 4 Beds
  • 3 Baths
  • 2,865 Sq Ft

  239 Hydrangea Way, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Clifton floorplan is a thoughtfully designed 1,865 sq. ft. ranch home, blending style and functionality in a single-level open layout.The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The kitchen opens to a large great room with two windows that let in

  Brooks Sears D R Horton Realty of Virginia LLC

  239 Hydrangea Way, Winchester, VA 22602
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  /58

  $585,000

  • 4 Beds
  • 2.5 Baths
  • 2,909 Sq Ft

  328 Sheridan Ave, Winchester, VA 22601

  Timeless charm meets thoughtful updates in this beautifully maintained all-brick 1958 home, offering effortless one-level living with a warm retro vibe. Freshly painted throughout and enhanced with new quartz countertops, classic subway tile backsplash, updated sink and faucet, and stylish new lighting, this home blends character with modern comfort. The main level is inviting and functional,

  Mary Casselano Dream Real Estate

  328 Sheridan Ave, Winchester, VA 22601
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  /54

  $653,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,865 Sq Ft

  234 Hydrangea Way, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Clifton floorplan is a thoughtfully designed 1,865 sq. ft. ranch home, blending style and functionality in a single-level open layout.The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The kitchen opens to a large great room with two windows that let in

  Brooks Sears D R Horton Realty of Virginia LLC

  234 Hydrangea Way, Winchester, VA 22602
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  /7

  $239,900

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  139 Little River Dr, Winchester, VA 22602

  Rebecca Sims Century 21 Redwood Realty

  139 Little River Dr, Winchester, VA 22602
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  /39

  $576,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,865 Sq Ft

  CLIFTON Plan at Willow Run, Winchester, VA 22601

  The Clifton by D.R. Horton is a stunning new construction, ranch home plan featuring 1,865 square feet of living space, 3 bedrooms, 2 bathrooms, and a 2-car garage. With a roomy and flexible floor plan, the Clifton is just as inviting as it is functional! Prepare to be enchanted by the spacious kitchen, equipped with brand-new stainless-steel appliances, sleek countertops, and cabinets that offer

  D.R. Horton Builder

  105 Trellis View Ln Unit 36406655, Winchester, VA 22601
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  /47

  $579,990 New Construction

  • 6 Beds
  • 4.5 Baths
  • 2,632 Sq Ft

  123 Wappinger Terrace, Winchester, VA 22602

  Quick Move-In Salem! This spacious 6 bedroom, 4.5 bath home offers 2,686 sq ft on the top two floors with a first-floor primary suite for easy main-level living. The open-concept design is perfect for entertaining, and the stone front elevation adds timeless curb appeal. Enjoy the added space of a finished recreation room with an additional bedroom—ideal for guests or a home office. Ask about

  D.R. Horton Builder

  123 Wappinger Terrace, Winchester, VA 22602
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  /6

  $20,000

  • Land
  • 0.46 Acre
  • $43,478 per Acre

  Lot 102 Bow Wood Trail, Winchester, VA 22602

  A Hidden Gem Waiting for YouNestled in the serene countryside of Winchester, Virginia, lies a great treed building lot on the lower side of Shawneeland. This picturesque piece of land offers the perfect blend of seclusion and convenience, making it an ideal location for building your dream home.Enjoy the tranquility and natural beauty of Shawneeland's private parks, perfect for relaxing

  Rick Guthrie Keller Williams Realty

  Lot 102 Bow Wood Trail, Winchester, VA 22602
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  /32

  $467,590 New Construction

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  125 Trellis View Ln, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Freeport floorplan is a thoughtfully designed villa blending style and functionality in a single-level open layout. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen, ideal for

  Brooks Sears D R Horton Realty of Virginia LLC

  125 Trellis View Ln, Winchester, VA 22602
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  /29

  $279,900

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  111 Genesee Trail, Winchester, VA 22602

  Remodeled rancher on 4 lots totaling 1.41 acres. Cute 2 bedroom 1 bath home freshly painted with new luxury vinyl planking throughout the entire house. Brand new bathroom with tub /shower. Open floor plan with bedrooms on each end of the house for privacy. 2 sheds that convey to store whatever your heart desires. Front deck to be stained as soon as weather permits. Come out and and enjoy all the

  Jacquelyn Rizzari MarketPlace REALTY

  111 Genesee Trail, Winchester, VA 22602
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  /51

  $1,595,000

  • Land
  • 158.44 Acres
  • $10,067 per Acre

  158.5 Acres Lot 3 Laurel Grove Rd, Winchester, VA 22602

  Incredible opportunity to own 158.443 acres of pristine, private land in an exclusive 3-lot, 440-acre subdivision. This is the most secluded parcel of the three, offering unmatched 360-degree panoramic views and a level of privacy that’s increasingly rare—yet just 15 minutes from town. Tucked away from the lights and sounds of civilization, this property provides a peaceful, off-the-beaten-path

  Nadeem Helfer Samson Properties

  158.5 Acres Lot 3 Laurel Grove Rd, Winchester, VA 22602
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  /83

  $653,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,909 Sq Ft

  232 Hydrangea Way, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Azalea floorplan is a thoughtfully designed 1,888 sq. ft. ranch home blending style and functionality in a single-level open layout. The moment you step inside the home, you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen,

  Brooks Sears D R Horton Realty of Virginia LLC

  232 Hydrangea Way, Winchester, VA 22602
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  /46

  $449,000

  • 3 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  25 W Southwerk St, Winchester, VA 22601

  Welcome to this beautifully updated gem in the heart of Winchester! From the moment you arrive, the expansive front porch invites you to sit back and enjoy the charm of one of the city's most sought-after locations. Situated just moments from Handley High School, vibrant downtown shops, local restaurants, and scenic parks, this home offers the perfect balance of neighborhood tranquility and

  Dan Whitacre Colony Realty

  25 W Southwerk St, Winchester, VA 22601
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  /33

  $576,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,865 Sq Ft

  55 Hydrangea Way, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Clifton floorplan is a thoughtfully designed 1,865 sq. ft. ranch home, blending style and functionality in a single-level open layout. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The kitchen opens to a large great room with two windows that let in

  Brooks Sears D R Horton Realty of Virginia LLC

  55 Hydrangea Way, Winchester, VA 22602
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  /48

  $649,900

  • 4 Beds
  • 3.5 Baths
  • 4,419 Sq Ft

  151 Darby Dr, Winchester, VA 22602

  Lovely contemporary home in the established Ravenwing subdivision, featuring a highly desirable main-level primary suite and a layout you’ll instantly fall in love with. The well-designed floor plan offers spacious second-floor bedrooms, a finished basement complete with a kitchenette, and a screened rear porch overlooking a fenced yard. Enjoy peaceful views of the picturesque common area and

  Dave Spence RE/MAX Roots

  151 Darby Dr, Winchester, VA 22602
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  /12

  $632,990 New Construction

  • 3 Beds
  • 2 Baths
  • 3,056 Sq Ft

  5 Williamson Rd, Winchester, VA 22602

  Welcome to Abrams Pointe, featuring new single-family homes in an established Winchester neighborhood, complete with wooded cul-de-sac homesites. The Drexel Floorplan is a spacious and versatile single-family home designed to suit a variety of lifestyles. With up to 3,213 finished square feet, the Drexel offers generous living space that can be customized to meet your needs. It features

  Dick Bryan New Home Star Virginia, LLC

  5 Williamson Rd, Winchester, VA 22602
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  /48

  $360,000

  • 3 Beds
  • 2.5 Baths
  • 1,852 Sq Ft

  135 Meade Dr, Winchester, VA 22602

  Welcome Home to 135 Meade Dr. This Winchester home is a great find, especially if you want to be close to everything. With its convenient location near Route 7 and I-81, this could be a great commuter home, and you are also just minutes from downtown Winchester, Shopping and Jim Barnett Park.This all‐brick ranch has 3 bedrooms and 2.5 bathrooms, with hardwood floors through most of the main

  Jarrett Sowder RE/MAX Roots

  135 Meade Dr, Winchester, VA 22602
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  /3

  $374,990 New Construction

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

  105 Bonnings Dr, Winchester, VA 22603

  Introducing the St. Paul, one of Maronda’s latest townhome designs.The St. Paul offers a range of 1,966 to 1,989 square feet of living space, including 3 to 4 bedrooms, 2.5 to 3.5 bathrooms, and a spacious 1-car garage. This new design offers plenty of personalization opportunities to fit your family’s unique needs.On the first floor of the home, you will find a spacious, open-concept floor plan.

  Maronda Homes Builder

  105 Bonnings Dr, Winchester, VA 22603
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  /7

  $200,000

  • Land
  • 5 Acres
  • $40,000 per Acre

  Lot A Cather Ln, Winchester, VA 22602

  Looking for the perfect spot to build your dream home? This 5-acre parcel of pasture land offers stunning views and an unbeatable location just minutes from town. With a 4-bedroom alternative septic certification letter already in place and minimal covenants and restrictions, you’ll have the freedom to create the home and lifestyle you’ve been envisioning. Local builder recommendations available.

  Kaitlyn Behr Samson Properties

  Lot A Cather Ln, Winchester, VA 22602
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  /21

  $384,900

  • 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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  /22

  $599,990 New Construction

  • 3 Beds
  • 1 Bath
  • 3,122 Sq Ft

  110 Lawford Way, Winchester, VA 22603

  Welcome home to the Rockwell, a versatile main-level living home designed for your lifestyle. The Rockwell's open-concept main floor seamlessly blends the kitchen, breakfast nook, and family room, creating a spacious and inviting atmosphere. The kitchen is a culinary enthusiast's dream, featuring a functional island with optional extension, ample storage, and a butler's pantry. The adjacent

  Brookfield Residential Builder

  110 Lawford Way, Winchester, VA 22603
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  /22

  $79,900

  • 3 Beds
  • 2 Baths
  • 1,118 Sq Ft

  107 Smith Dr, Winchester, VA 22603

  Resort-Style Living at Regency Lakes! Enjoy an amenity-rich community that also offers easy access to route 7 and many shopping and dining options nearby. The home features vinyl flooring in the main living areas and carpet in the bedrooms. A light and bright kitchen is the heart of the home, with plenty of storage and counterspace. A charming breakfast nook and laundry closet add convenience to

  Heloisa Amar Samson Properties

  107 Smith Dr, Winchester, VA 22603
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  /97

  $1,200,000

  • 6 Beds
  • 5 Baths
  • 6,682 Sq Ft

  217 W Boscawen St, Winchester, VA 22601

  Historic Water Street Inn a magnificent legacy residence, profitable Bed & Breakfast, or sophisticated professional office opportunity! Located in Winchester's Historic District, two blocks from Old Town Walking Mall! Six large bedrooms and five full baths, this historically significant property is one of a kind, offering private garden spaces, romantic terraces, sunlight filled porches, and

  Gillian Greenfield Coldwell Banker Premier

  217 W Boscawen St, Winchester, VA 22601
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  /22

  $332,900

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft

  105 Buckskin Trail, Winchester, VA 22602

  Nestled in the charming Shawneeland community, you will enjoy the mountain views in this delightful ranch-style home which offers a perfect blend of comfort and modern living. With a major renovation completed in 2026, this residence boasts a fresh and inviting atmosphere, ideal for creating lasting memories. The exterior features low-maintenance vinyl siding, complemented exterior lighting that

  Bruce Elsey Long & Foster Real Estate, Inc.

  105 Buckskin Trail, Winchester, VA 22602
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  /2

  $69,900

  • Land
  • 0.19 Acre
  • $367,895 per Acre

  Lot 84 Purcell Ln, Winchester, VA 22603

  Build Your Vision Near Winchester City LimitsPrime buildable lot offering the perfect balance of convenience and freedom. Located just minutes from Winchester City but still in county, shopping, the hospital, and Route 37, this property is ready for your project with public water and sewer hookups available. Freedom to Build: No HOA or restrictive covenants—ideal for a custom small home or a

  Jim Thomson Realty ONE Group Old Towne

  Lot 84 Purcell Ln, Winchester, VA 22603
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  /49

  $315,000

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft

  321 Copperfield Ln, Winchester, VA 22602

  Super cute 3 level townhome with a great design, two full baths one in the basement one in the upper level and a half on the main. Spacious and affordable!! 2 assigned parking spaces. Laminate flooring throughout. Spacious, light and bright!! Fenced backyard and deck. Freshly painted and NEW carpet, NEW stainless steel appliances!! Hurry to see today, it is vacant, quick closing possible!!

  Heather Mary Webb RE/MAX Allegiance

  321 Copperfield Ln, Winchester, VA 22602
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  /43

  $399,900

  • 2 Beds
  • 2 Baths
  • 1,405 Sq Ft

  1851 Melvor Ln, Winchester, VA 22601

  Extremely well-maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottages 55+ community. This main-level living home features an open floor plan, vaulted ceiling, solar tubes for natural light, and a cozy gas fireplace in the living room. The primary suite offers a private bath, while a bright Florida room provides additional space for relaxing or entertaining. Step outside to

  RoxAnn Grimes RE/MAX Roots

  1851 Melvor Ln, Winchester, VA 22601

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