Winchester, VA Homes for Sale under $500,000

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  /37

  $425,000

  $5K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,806 Sq Ft

  133 Woodrow Rd, Winchester, VA 22602

  Set on the east side of Winchester in Carlisle Heights, this inviting 3 bedroom, 3 full bath split foyer offers style, function, and a commuter-friendly location just minutes from Route 7. Inside, you’ll find a bright, open feel with easy-care flooring flowing through the main living spaces and bedrooms. The kitchen has been tastefully refreshed with crisp white cabinets, stainless steel

  Kevin Pringle Samson Properties

  133 Woodrow Rd, Winchester, VA 22602
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  /15

  $435,000

  • 5 Beds
  • 4 Baths
  • 2,014 Sq Ft

  122 Cherry Hill Cir, Winchester, VA 22602

  Nestled in the charming Green Acres subdivision, this delightful split-level home offers a perfect blend of comfort and functionality. With five spacious bedrooms and four full bathrooms, there's ample room for everyone to unwind and thrive. The heart of the home features a cozy fireplace, inviting you to gather with loved ones during chilly evenings. The fully finished basement, complete with

  Jen Moore ERA Oakcrest Realty, Inc.

  122 Cherry Hill Cir, Winchester, VA 22602
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  /39

  $421,000

  • 3 Beds
  • 2.5 Baths
  • 2,277 Sq Ft

  422 S Loudoun St, Winchester, VA 22601

  Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the charm of yesteryear this home offers the conveniences of modern living. Traditionally appointed, the main level of the home provides the perfect separation of spaces with a large formal living room, dining room, gourmet kitchen, additional full bath and main level

  Dana Cloud Realty ONE Group Old Towne

  422 S Loudoun St, Winchester, VA 22601
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  /20

  $474,990

  New Construction

  • 2 Beds
  • 1 Bath
  • 1,564 Sq Ft

  110 Carnation Way, Winchester, VA 22603

  Welcome to your ideal one-level villa- the Hemingway! This thoughtfully designed home centers around a spacious kitchen, perfect for both daily life and entertaining guests. The main level offers two generous bedrooms, including a primary suite featuring a large walk-in closet and a private en suite bathroom for ultimate comfort. Convenience is key with a laundry room located just off the 2-car

  Brookfield Residential Builder

  110 Carnation Way, Winchester, VA 22603
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  /17

  $409,900

  New Construction $10K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,660 Sq Ft

  123 Killbuck Trail, Winchester, VA 22602

  Current Shawneeland Inventory208 Beaver Trail210 Beaver Trail212 Falcon Trail211 Inca Trail103 Tonto Trail123 Killbuck TrailPremium Finishes: Enjoy a builder-upgraded interior featuring gleaming hardwood floors throughout the entire home (including all bedrooms) and elegant tile in all bathrooms.Gourmet Kitchen: Equipped with upgraded cabinetry, sleek granite

  Jim Thomson Realty ONE Group Old Towne

  123 Killbuck Trail, Winchester, VA 22602
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  /26

  $419,990

  New Construction

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

  126 Swansong Place, Winchester, VA 22603

  Exceptional value for a 4‐bedroom END‐UNIT townhome—almost ready for summer 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 entry‐level bedroom with full bath, a bright open‐concept main

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  126 Swansong Place, Winchester, VA 22603
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  /55

  $424,999

  $25K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,850 Sq Ft

  1105 Henry Dr, Winchester, VA 22602

  Home offers nearly 3000 sqft of finished living space that has Luxury Vinyl flooring through out both levels (absolutely no carpet) that features 4 bedrooms and 2.5 baths situated on over a 1/2 acre (.61) of ground. Upon entering you will find an open floor plan that encompasses a large living room and dining room with canned lighting then pours into the large eat in kitchen (new appliances) that

  James Amick RE/MAX Roots

  1105 Henry Dr, Winchester, VA 22602
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  /72

  $469,000

  Open Sat 11AM - 1PM $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,703 Sq Ft

  231 Bentley Ave, Winchester, VA 22602

  Easy main-level living with bonus space when you need it—this one just works. A beautiful, covered front porch welcomes you into a foyer that opens to a comfortable living room centered around a gas fireplace with built-ins, creating a space that feels both open and inviting. Toward the rear of the home, the dining area is filled with natural light from well-placed windows. The kitchen is

  Natalie Langford ERA Oakcrest Realty, Inc.

  231 Bentley Ave, Winchester, VA 22602
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  /10

  $468,900

  Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,770 Sq Ft

  121 Travis Ct, Winchester, VA 22602

  Beautifully updated colonial in an established neighborhood just minutes from Winchester shopping, dining, and commuter routes! This spacious home features a newly remodeled kitchen with quartz countertops, freshly painted cabinetry, newer appliances, and plenty of space for cooking and gathering. Fresh paint throughout, refinished hardwood floors, and brand-new carpet give the home a bright,

  Donna Anderson Samson Properties

  121 Travis Ct, Winchester, VA 22602
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  /55

  $469,900

  $20K PRICE DROP

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

  620 Crystal Ct, Winchester, VA 22601

  Back and better than EVER! New Sales Price!! Rare Cul-de-Sac Gem in the Heart of Winchester! Now priced nearly $20,000 under appraisal value!! Discover the perfect blend of tranquility and city convenience at 620 Crystal Court. Situated in a sought-after, quiet cul-de-sac right in the center of Winchester, this stunning 4-bedroom, 2.5-bathroom residence has been thoughtfully updated and is ready

  VAIBHAV AGARWAL Realty FC, LLC

  620 Crystal Ct, Winchester, VA 22601
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  /22

  $402,855

  New Construction Open Sat 12PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 2,000 Sq Ft

  114 Nepal Ct, Winchester, VA 22602

  Welcome to Maronda Homes newest townhome community! Winchester Ridge is conveniently located near shopping and dining options. The St. Paul Townhome features FOUR bedrooms, THREE 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, and a

  Holly Horne Poole New Home Star Virginia, LLC

  114 Nepal Ct, Winchester, VA 22602
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  /24

  $402,435

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,012 Sq Ft

  116 Shuoner Ct, Winchester, VA 22602

  June 2026 Delivery – St. Paul G4 BR | 3.5 BA | 1-Car Garage | Finished Lower Level | Larger Deck Beautiful wooded homesites available!Offering up to 2,012 sq. ft. of modern, open-concept living — customize your home the way you like, or keep everything as-is at this price, including a 4th bedroom. Home Highlights Open-concept main level – perfect for entertaining Quartz countertops

  Jimmy Thomas New Home Star Virginia, LLC

  116 Shuoner Ct, Winchester, VA 22602
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  /39

  $484,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,906 Sq Ft

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

  The Deerfield is a thoughtfully designed home with four bedrooms and two-and-a-half baths. The kitchen features a walk-in pantry and a breakfast island, which includes a sink, making it perfect for food preparation, and has plenty of room for stools, so you can entertain. The kitchen looks out over the open-concept dining area and great room. All four bedroom are upstairs along with the Laundry

  D.R. Horton Builder

  137 Seminole Dr Unit 36203782, Winchester, VA 22602
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  /38

  $409,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 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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  /35

  $459,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,905 Sq Ft

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

  The Adams II townhome features 1,905 sq. ft. of stylish and flexible living space, including 4 bedrooms, 3.5 bathrooms, and a 1-car rear-load garage. The gourmet kitchen is equipped with quartz countertops, stainless steel appliances, recessed lighting, a generous island, and sleek Duraform cabinetry. The lower-level bonus room offers endless possibilities—use it as a rec room, home office, or an

  D.R. Horton Builder

  1831 Reese Ct Unit 37025141, Winchester, VA 22601
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  /83

  $457,750

  Open Sat 12PM - 2:30PM

  • 3 Beds
  • 3 Baths
  • 2,327 Sq Ft

  131 Country Club Cir, Winchester, VA 22602

  Welcome to 131 Country Club Circle, a beautifully appointed all-brick masonry residence offering timeless construction and exceptional living space. This impressive home showcases tall ceilings and real hardwood flooring throughout the main level, creating a warm yet refined atmosphere. The thoughtfully designed layout includes a sunroom on the main level, ideal as a home office or flex space,

  Alexi Faraco Smart Realty, LLC

  131 Country Club Cir, Winchester, VA 22602
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  /28

  $420,000

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  775 Pack Horse Rd, Winchester, VA 22603

  Completely remodeled and move-in ready, this charming property at 775 Pack Horse Road in Frederick County, VA offers the perfect blend of modern updates and peaceful country living. Situated on a picturesque setting, the home has been thoughtfully renovated throughout, featuring updated finishes, refreshed interiors, and attention to detail in every room. Enjoy the convenience of a detached

  Amanda Slate Keller Williams Realty

  775 Pack Horse Rd, Winchester, VA 22603
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  /53

  $499,900

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,800 Sq Ft

  105 Amberfield Ct, Winchester, VA 22602

  Move in Ready!!! Low $150/month HOA fee. Nestled in the serene enclave of Abram's Chase and located within minutes of Historic downtown Winchester, the hospital, restaurants and shopping. This exquisite Craftsman-style home features 2 bedrooms, a private study and 2 full bathrooms. It is designed for those seeking a refined lifestyle in a vibrant senior community, with an age requirement of 55

  Cynthia Butler Samson Properties

  105 Amberfield Ct, Winchester, VA 22602
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  /3

  $482,990

  New Construction $17K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,216 Sq Ft

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

  The Glendale is a new construction home plan featuring 2,216 square feet of living space, 4 bedrooms, 3.5 baths and a 2-car garage. The Glendale gives you the features you’re looking for at the price you want! You’ll immediately feel at home as you enter into the spacious family room. This living space flows nicely into the eat-in kitchen which highlights a peninsula island overlooking the family

  D.R. Horton Builder

  137 Seminole Dr Unit 39403232, Winchester, VA 22602
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  /44

  $425,000

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  823 Woodland Ave, Winchester, VA 22601

  Charming on the outside, modern on the inside Located in a charming, very quiet neighborhood, this home offers the perfect blend of timeless character and a fully modern renovation. Featuring 3 beautifully updated levels, the home showcases new Bruce hardwood flooring throughout with no transitions, creating a seamless, elegant flow and easy mobility. Every detail has been thoughtfully upgraded

  Lenora Zaccur Coldwell Banker Realty

  823 Woodland Ave, Winchester, VA 22601
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  /17

  $475,000

  • Land
  • 89.87 Acres
  • $5,285 per Acre

  0 0 Unit VAFV2041652, Winchester, VA 22602

  Approximately 90-acre wooded parcel offering abundant space for recreation, hunting, and enjoying nature, with Little Brush Creek bordering the property. This private retreat features approximately 2,500 feet of creek frontage and has been recently surveyed. The property is accessed by frontage on Shockyeville Road or established easement and offers a peaceful, remote setting while still being

  Brandi Marcum Pearson Smith Realty, LLC

  0 0 Unit VAFV2041652, Winchester, VA 22602
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  /22

  $419,999

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,000 Sq Ft

  HOMESITE 226 Shouner Ct, Winchester, VA 22602

  **END UNIT** 110 SHUONER Ct – Model Home | Summer 2026 Delivery AvailableSt. Paul TBB | 4 BR | 3.5 BA | 1-Car Garage | Finished Lower Level + Larger Deck Beautiful wooded homesites available!Offering up to 2,000 sq. ft. of modern, open-concept living — customize your home the way you like, or keep everything as-is at this price, including a 4th bedroom. Home Highlights Open-concept main

  Jimmy Thomas New Home Star Virginia, LLC

  HOMESITE 226 Shouner Ct, Winchester, VA 22602
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  /35

  $409,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,920 Sq Ft

  1805 Harvest Dr, Winchester, VA 22601

  1805 Harvest Drive is an attractive new 3 level townhome with full brick front in Winchester, VA for April move-in. Our modern Adams II floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, white cabinets, and stainless-steel appliances. The

  D.R. Horton Builder

  1805 Harvest Dr, Winchester, VA 22601
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  /27

  $404,990

  New Construction

  • 3 Beds
  • 1.5 Baths
  • 2,433 Sq Ft

  410 Granite Ridge Dr, Winchester, VA 22603

  This stunning two-level villa boasts a modern open concept design that seamlessly connects living spaces for an inviting and spacious feel. The main level features a living room that opens effortlessly to the dining area, creating a perfect space for entertaining and family gatherings. The expansive rear kitchen includes an L-shaped layout with an eating bar and an island with additional bar

  Brookfield Residential Builder

  410 Granite Ridge Dr, Winchester, VA 22603

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