Winchester, VA 2-Story Homes for Sale

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  $825,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,127 Sq Ft

  106 Mate Ct, Winchester, VA 22602

  Welcome to 106 Mate Court, a beautifully custom-designed 2026 new construction home situated on a private 0.27-acre cul-de-sac lot in Winchester’s desirable Red Fox Run community. Backing to mature trees with scenic natural views, this stunning property offers the perfect blend of privacy, modern craftsmanship, thoughtful design, and peaceful living. Featuring over 3,100 square feet of total

  deborah longo Taylor Properties

  106 Mate Ct, Winchester, VA 22602
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  $389,000

  • 2 Beds
  • 2 Baths
  • 1,809 Sq Ft

  328 Longview Ave, Winchester, VA 22601

  This ranch home in Winchester City has been meticulously maintained. Beautiful hardwood floors. Dining room can be converted back to a third bedroom, simply install doors that are being stored in the basement. Basement is 75% finished and offers endless possibilities. The remaining 25% provides room for ample storage and/or a workshop. Note: toilet in workshop area is NOT functional. New HVAC

  Kelly Bauer Coldwell Banker Premier

  328 Longview Ave, Winchester, VA 22601
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  $380,000

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,848 Sq Ft

  108 Wild Rose Cir, Winchester, VA 22602

  Welcome home to this beautifully renovated 4-bedroom, 2 full-bath rancher situated on a spacious 0.23-acre lot in the heart of Winchester. Thoughtfully updated from top (New Roof) to bottom, this move-in-ready home offers the perfect blend of modern finishes and comfortable living. The main level has newly installed LVP flooring, 3 bedrooms, a full bath, and a wood-burning fireplace. The fully

  Jon Fleming Weichert Realtors - Blue Ribbon

  108 Wild Rose Cir, Winchester, VA 22602
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  /19

  $399,900

  New Construction $10K PRICE INCREASE

  • 3 Beds
  • 3 Baths
  • 1,914 Sq Ft

  107 Pinto Trail, Winchester, VA 22602

  5-27-26 I AM DONE AND READY! Split foyer low in community and flat lot with easy access out of subdivision. Other inventory of new homes in community208 Beaver Trail210 Beaver Trail212 Falcon Trail211 Inca Trail123 Killbuck Trail103 Tonto

  Jim Thomson Realty ONE Group Old Towne

  107 Pinto Trail, Winchester, VA 22602
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  $665,000

  $6K PRICE INCREASE

  • 5 Beds
  • 5.5 Baths
  • 4,755 Sq Ft

  220 Flanagan Dr, Winchester, VA 22602

  Welcome to this exquisite all-brick colonial, nestled on a desirable corner lot with effortless commuting access. Spanning over 4700 square feet. This elegant home features five generously sized bed rooms with five full and one half bathroom, including a luxurious first-floor primary suite. Gleaming Hardwood floors grace the entire first floor. The walk up basement offers two additional full

  Robert Mann Burch Real Estate Group, LLC

  220 Flanagan Dr, Winchester, VA 22602
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  $695,000

  New Construction $16K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  0 Tumble Leaf Ln, Winchester, VA 22602

  CARRINGTON HOMES AT FALL RIDGE ESTATES- 5 Acre Wooded LOTS WITH MOUNTAIN VIEWS. Choose from 7 different floorplans including our Main Level Living Evergreene model with standard 13' Family Rm Ceilings Model Home Open on Weekends from 11-5 at 156 Covey Lane Winchester Va

  Daniel Boris Pearson Smith Realty, LLC

  0 Tumble Leaf Ln, Winchester, VA 22602
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  $350,000

  New Construction $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft

  513 Pheasant Dr, Winchester, VA 22602

  Welcome to this newly built colonial in Wilde Acres situated on 1/4 acre lot nestled among the trees and surrounded by a wall made of native stone. Upon entry, enjoy the open living area and wood floors which make the space warm and comfortable. The galley kitchen offers ample counterspace and new stainless steel appliances. The convenient main level full bath also has hookup for stackable washer

  Ismael Carino MarketPlace REALTY

  513 Pheasant Dr, Winchester, VA 22602
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  $474,500

  Coming Soon

  • 3 Beds
  • 3.5 Baths
  • 2,650 Sq Ft

  121 Cherokee Trail, Winchester, VA 22602

  Lake and mountain views, a private in-ground pool, and an adjoining 1-acre lot — this beautifully updated Shawneeland home sits on .37 acres and conveys with an additional acre of record (Tax Map ID #49A031A13A), for approximately 1.37 acres of mountain privacy. Filled with natural light, the home features hardwood floors, fireplaces throughout, and a renovated kitchen with quartz countertops,

  Sebastian Langenberg Corcoran McEnearney

  121 Cherokee Trail, Winchester, VA 22602
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  /90

  $490,000

  $27K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 1,962 Sq Ft

  235 Peppermint Spring Ln, Winchester, VA 22603

  Discover Your Private Retreat: 235 Peppermint Spring LaneNestled in the serene landscape of Winchester, Virginia, 235 Peppermint Spring Lane offers a rare combination of spacious country living and modern convenience. This charming single-family home sits on a sprawling 6.67-acre lot, providing a peaceful sanctuary backing to conservation land just minutes from the vibrant energy of historic

  Andrew Hensley Samson Properties

  235 Peppermint Spring Ln, Winchester, VA 22603
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  $339,995

  $200K PRICE INCREASE

  • 3 Beds
  • 3 Baths
  • 1,310 Sq Ft

  593 N Kent St, Winchester, VA 22601

  This charming home, a short walk from historic Winchester, underwent a complete studs up renovation a few years ago. With all new insulation, roof, energy efficient double pane windows, and updated systems, it offers efficiency and ease. The open floor plan flows into a kitchen with a dedicated pantry closet. Three appropriately sized bedrooms include a master with its own bath. Plus, enjoy

  Lawrence Lessin Homes By Owner, Inc.

  593 N Kent St, Winchester, VA 22601
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  $1,025,000

  $175K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,497 Sq Ft

  466 Merrimans Ln, Winchester, VA 22601

  An extraordinary and rarely available offering within the city limits, 466 Merrimans Lane presents a stately brick residence set on an impressive 2.03 acre lot—an uncommon blend of privacy, space, and convenience in an in-town setting. This classic home features three generously sized bedrooms and three-and-a-half baths, with a traditional floor plan designed for both comfortable everyday living

  Laura White ERA Oakcrest Realty, Inc.

  466 Merrimans Ln, Winchester, VA 22601
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  $524,990

  New Construction $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,023 Sq Ft

  619 Farmington Blvd, Winchester, VA 22602

  Contact me to learn how you can receive up to $30,000 in builder-paid closing costs! The home is vacant, move-in ready, and includes pre-selected upgrades and a new-construction warranty. Welcome to this beautifully crafted new home by a respected local builder, offering over 2,000 square feet of thoughtfully designed living space in the desirable Sovereign Village community. The inviting

  Marisa Varley ERA Oakcrest Realty, Inc.

  619 Farmington Blvd, Winchester, VA 22602
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  $899,900

  New Construction $50K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 2,488 Sq Ft

  Lot 11 Keval Gyan Way, Winchester, VA 22603

  Model available to see! Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house (new PIN OAK model); it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle

  Jim Thomson Realty ONE Group Old Towne

  Lot 11 Keval Gyan Way, Winchester, VA 22603

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