Winchester, VA Homes

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  $589,990 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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  /13

  $2,100 per month

  • 3 Beds
  • 2 Baths
  • 1,823 Sq Ft
  • House for Rent

  1701 Brandon Dr, Winchester, VA 22601

  Great home in fantastic location., Walking distance to Handley. Nice fenced rear yard, great deck. Laundry on first level. Quartz counter top. Two Fireplaces not operational. Large finished room in basement. LOT of storage and shelving in unfinished portion of basement. Great building under deck for mowers and outside storage. Extremely convenient quiet street. Pets on case by case basis. All

  Jeff Webber Long & Foster Real Estate, Inc.

  1701 Brandon Dr, Winchester, VA 22601
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  /30

  $340,000 Sold Aug 12, 2025

  223 Monticello Square, Winchester, VA 22602

  • 3 Beds
  • 2.5 Baths
  • 1,784 Sq Ft
  • Built 2011

  Last Sold Summary

  • $191/SF
  • 15 Days On Market

  Current Estimated Value $343,605

  Last Listing Agent Minhkhoa Tran Fairfax Realty Premier

  223 Monticello Square, Winchester, VA 22602
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  /22

  Est $291,696 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 954 Sq Ft

  313 Summit Ave, Winchester, VA 22601

  313 Summit Ave, Winchester, VA 22601
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  $235,000

  • Land
  • 0.36 Acre
  • $652,778 per Acre

  506 Fairmont Ave, Winchester, VA 22601

  Introducing a newly configured Winchester City lot ready for you to build your dream home! The heavy lifting has already been done. The current owner worked with the neighbors and the City to widen the lot to accommodate a sizable home. With a width of approximately 100 feet you will have plenty of space to spread out. Located on a storied street in downtown Winchester, you will enjoy the perks

  Dan Whitacre Colony Realty

  506 Fairmont Ave, Winchester, VA 22601
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  /8

  $1,595 per month

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Townhouse for Rent

  202 E Whitlock Ave, Winchester, VA 22601

  Experience the charm of this beautifully renovated end-of-row townhouse in the heart of the City of Winchester, available for lease starting November 19, 2025. This residence, originally built in 1956, will undergo a major renovation, ensuring modern luxury meets classic elegance. With three spacious bedrooms and a full bath, this home is designed for comfort and style. The partially finished

  Brandon Pifer Pifer Realty, LLC

  202 E Whitlock Ave, Winchester, VA 22601
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  /26

  $207,500 Sold Jun 11, 2025

  308 Wardensville Grade, Winchester, VA 22602

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1998

  Last Sold Summary

  • $180/SF
  • 83 Days On Market

  Current Estimated Value $264,701

  Last Listing Agent Leah Marabella Realty ONE Group Old Towne

  308 Wardensville Grade, Winchester, VA 22602
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  /29

  Est $304,251 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,250 Sq Ft

  2917 First St, Winchester, VA 22601

  2917 First St, Winchester, VA 22601
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  /24

  $539,990 New Construction

  • 3 Beds
  • 3 Baths
  • 2,050 Sq Ft

  113 Sunflower Way, Winchester, VA 22603

  Brand new main level living Hemingway is Ready for you to call home! At the heart of the home, the gourmet kitchen shines with stainless steel appliances, quartz countertops, and upgraded cabinetry. The kitchen flows seamlessly into the dining and family rooms, where additional windows create a bright, inviting atmosphere—perfect for entertaining. Just beyond, a rear screened porch offers the

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  113 Sunflower Way, Winchester, VA 22603
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  $2,250 per month

  • 3 Beds
  • 3.5 Baths
  • 2,151 Sq Ft
  • Townhouse for Rent

  109 Sequoia Dr, Winchester, VA 22602

  Beautifully appointed town home in the sought after Fieldstone neighborhood. Tons of upgrades including granite counters, 42" cabinets, hardwood floors, fireplace in family room and large rear deck. Freshly painted and new carpet installed! This end unit features a fantastic open floor plan with gourmet kitchen and large center island.

  Rebecca Sims Century 21 Redwood Realty

  109 Sequoia Dr, Winchester, VA 22602
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  /20

  $305,000 Sold Oct 08, 2025

  102 Zephyr Ln, Winchester, VA 22602

  • 3 Beds
  • 1.5 Baths
  • 1,634 Sq Ft
  • Built 2004

  Last Sold Summary

  • $187/SF
  • 95 Days On Market

  Current Estimated Value $306,678

  Last Listing Agent Kandi McKenzie Realty ONE Group Old Towne

  102 Zephyr Ln, Winchester, VA 22602
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  /31

  Est $278,892 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 850 Sq Ft

  2944 Second St, Winchester, VA 22601

  2944 Second St, Winchester, VA 22601
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  /13

  $374,990 New Construction

  • 3 Beds
  • 1.5 Baths
  • 1,752 Sq Ft

  123 Castaway Place, 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

  123 Castaway Place, Winchester, VA 22603
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  /16

  $1,500 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Townhouse for Rent

  2 E Germain St, Winchester, VA 22601

  Location! Walking distance from downtown walking mall and public transportation. 2 bedroom 1 bath apartment with hardwood flooring throughout living room and bedrooms. Property features a front porch, wash/dryer hookup and off street parking. Yard maintenance is included in rent. Requirements to qualify: 1) Minium annual household income $67K, 2) Good credit, and 3) Good landlord reference. $47

  Courtney Spaid Crum Realty, Inc.

  2 E Germain St, Winchester, VA 22601
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  /26

  $229,500 Sold Jan 22, 2025

  128 Little River Dr, Winchester, VA 22602

  • 2 Beds
  • 1.5 Baths
  • 1,580 Sq Ft
  • Built 1989

  Last Sold Summary

  • $145/SF
  • 4 Days On Market

  Current Estimated Value $242,313

  Last Listing Agent Sheila Pack RE/MAX Roots

  128 Little River Dr, Winchester, VA 22602
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  /19

  Est $326,803 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,472 Sq Ft

  2928 First St, Winchester, VA 22601

  2928 First St, Winchester, VA 22601
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  $799,900 New Construction

  • 3 Beds
  • 2.5 Baths

  6 Dicks Hollow Rd, Winchester, VA 22603

  Great Opportunity on this Brand-New Ranch Home Sitting on 2.82 Acres, Convent to Shopping and Commuter Routes to Winchester, Martinsburg and Northern Virginia. Open Concept with Split Bedroom Design. Front Board and Batten siding for a unique look. Large Primary Suite with spacious walk-in closet and 6' Shower. Main Level Private Office. Chief's Kitchen with Quarts Countertops, Island, Stainless

  Brett Sowder RE/MAX Roots

  6 Dicks Hollow Rd, Winchester, VA 22603
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  /24

  $2,295 per month

  • 3 Beds
  • 2 Baths
  • 1,397 Sq Ft
  • House for Rent

  108 Senseny Glen Dr, Winchester, VA 22602

  3-bedroom, 2-bath brick-front rancher with a 2 car garage, covered front porch, rear deck, partially fenced rear yard and storage shed. The living room features a gas fireplace. Located near Jim Barnett Park and just minutes from downtown Winchester as well as shopping and schools. No smoking or vaping is allowed on the property. A small pet may be considered - restrictions apply as to number,

  Barbara Gaul Jim Barb Realty, Inc.

  108 Senseny Glen Dr, Winchester, VA 22602
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  /34

  $585,000 Sold Aug 07, 2025

  720 Beehive Way, Winchester, VA 22601

  • 4 Beds
  • 3.5 Baths
  • 2,571 Sq Ft
  • Built 2006

  Last Sold Summary

  • $228/SF
  • 53 Days On Market

  Current Estimated Value $591,567

  Last Listing Agent Amy Emerson-Kerns Cambridge Premier Realty, LLC.

  720 Beehive Way, Winchester, VA 22601
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  /8

  Est $239,936 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,064 Sq Ft

  521 Monticello St, Winchester, VA 22601

  521 Monticello St, Winchester, VA 22601
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  $1,550,000

  • Land
  • 128.56 Acres
  • $12,057 per Acre

  Lot 1 (128.556 Acres Laurel Grove Rd, Winchester, VA 22602

  Welcome to a truly rare offering — a first-time release of an extraordinary 128+ acre estate parcel, perfectly suited for the discerning buyer seeking privacy, natural beauty, and limitless potential. This is one of only three exclusive lots masterfully curated from a 439-acre legacy estate, designed with elegance, intention, and long-term value in mind.Tucked behind private, impeccably

  Nadeem Helfer Corcoran McEnearney

  Lot 1 (128.556 Acres Laurel Grove Rd, Winchester, VA 22602
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  /13

  $1,395 per month

  • 1 Bed
  • 1 Bath
  • 3,267 Sq Ft
  • House for Rent

  515 N Loudoun St Unit 1, Winchester, VA 22601

  LANDLORD PAYS UTILITIES - INCLUDING HEAT! MAIN-LEVEL APARTMENT. Old-fashioned charmer near downtown Winchester. Spacious 1-BR apartment with exposed brick, hardwood floors, 10+ foot ceilings, pocket doors. Kitchen with shelves, pantry, new LVP floor. Walk-in closet. Landlord pays heat, electricity, water & sewer, city trash pickup, lawn care. Pets case-by-case. Cats considered. No dogs. No

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  515 N Loudoun St Unit 1, Winchester, VA 22601
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  /3

  $175,000 Sold Mar 12, 2025

  Lot 13 Liza Kates Ln, Winchester, VA 22603

  • Land
  • 11.27 Acres
  • $15,528 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 1,136 Days On Market

  Last Listing Agent Jim Thomson Realty ONE Group Old Towne

  Lot 13 Liza Kates Ln, Winchester, VA 22603
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  /22

  Est $246,172 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 765 Sq Ft

  514 Armour Dale, Winchester, VA 22601

  514 Armour Dale, Winchester, VA 22601
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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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  $2,195 per month

  • 3 Beds
  • 2.5 Baths
  • 1,200 Sq Ft
  • Townhouse for Rent

  104 Reign Way, Winchester, VA 22603

  Discover this spacious three-level townhome built by Ryan Homes in 2018, now available for long-term lease. This well-maintained home offers three bedrooms with walk-in closets, two full baths, and one half-bath. The open floor plan includes a large kitchen with an island, a dining area, and a comfortable living room. The entry-level bonus room provides flexible use as storage, an office, or

  Kalyan Karki Pearson Smith Realty, LLC

  104 Reign Way, Winchester, VA 22603
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  /44

  $405,000 Sold Mar 04, 2025

  102 Berkshire Cir, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 872 Sq Ft
  • Built 1994

  Last Sold Summary

  • $464/SF
  • 0 Days On Market

  Current Estimated Value $391,293

  Last Listing Agent Sherry Santmyer Hunt Country Sotheby's International Realty

  102 Berkshire Cir, Winchester, VA 22601
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  /71

  Est $339,917 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,600 Sq Ft

  517 Armour Dale, Winchester, VA 22601

  517 Armour Dale, Winchester, VA 22601
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  /65

  $799,900

  • 4 Beds
  • 3.5 Baths
  • 5,040 Sq Ft

  2411 Hunting Ridge Rd, Winchester, VA 22603

  This is the one you've been waiting for! Welcome to 2411 Hunting Ridge Rd. This large and private classic colonial is ready for you. With over 5000 sq ft and more than 5 acres of property, this beautiful home has it all. The winding tree-lined (and paved!) driveway invites you in. Enter into the welcoming two story foyer, which is flanked by lovely formal dining and sitting rooms. Exploring

  Amanda White Nova Home Hunters Realty

  2411 Hunting Ridge Rd, Winchester, VA 22603
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  /12

  $1,300 per month

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft
  • Townhouse for Rent

  2918 Packer St, Winchester, VA 22601

  2 bedroom, 1 1⁄2 bath, 2 story townhouse with two paved parking spots on a dead end street. Lawn service is included in the rent. Painted interior, large eat-in kitchen with range and refrigerator, laundry with full size washer/dryer. EBB heat and 2 wall unit a/c's. No Smokers and No Pets. Tenant is responsible for all utilities and is required to obtain renters insurance. Good credit without any

  Barbara Gaul Jim Barb Realty, Inc.

  2918 Packer St, Winchester, VA 22601
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  /23

  $145,000 Sold Nov 05, 2025

  0 Gough Rd Unit VAFV2033030, Winchester, VA 22602

  • Land
  • 10 Acres
  • $14,500 per Acre

  Last Sold Summary

  • 126 Days On Market

  Last Listing Agent Chad Pangle Whitetail Properties Real Estate, LLC

  0 Gough Rd Unit VAFV2033030, Winchester, VA 22602
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  /46

  Est $521,925 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,568 Sq Ft

  605 Kernstown Ct, Winchester, VA 22601

  605 Kernstown Ct, Winchester, VA 22601
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  /2

  $359,900 Coming Soon

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  2952 Grace St, Winchester, VA 22601

  Charming one level, 3-bedroom, 1 full bath home conveniently located in the heart of Winchester. Recently remodeled with new flooring throughout, updated bathroom, and modern fixtures. Thoughtful updates make this home move-in ready and ideal for easy, single-level living. Close to shopping, dining, and commuter routes.

  Carolina Mosquera Weichert, REALTORS

  2952 Grace St, Winchester, VA 22601
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  /40

  $2,900 per month

  • 5 Beds
  • 3 Baths
  • House for Rent

  220 Munsee Cir, Winchester, VA 22602

  Discover an exquisite opportunity to lease a brand-new contemporary residence in the prestigious Abrams Pointe community, available from November 4, 2025. This stunning 5-bedroom, 4-bathroom home boasts an open floor plan that seamlessly integrates the living, dining, and kitchen areas, perfect for entertaining. The gourmet kitchen features a spacious island, ENERGY STAR appliances, and a

  Sridevi Miriyala Maram Realty, LLC

  220 Munsee Cir, Winchester, VA 22602
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  /26

  $565,000 Sold May 21, 2025

  2532 Middle Rd, Winchester, VA 22601

  • 4 Beds
  • 3 Baths
  • 2,108 Sq Ft
  • Built 2022

  Last Sold Summary

  • $268/SF

  Current Estimated Value $588,617

  Last Listing Agent Sarah Reynolds Keller Williams Realty

  2532 Middle Rd, Winchester, VA 22601
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  /38

  Est $511,581 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,312 Sq Ft

  3022 Saratoga Dr, Winchester, VA 22601

  3022 Saratoga Dr, Winchester, VA 22601
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  /35

  $279,000

  • 2 Beds
  • 1 Bath
  • 1,176 Sq Ft

  239 Chestnut St, Winchester, VA 22601

  ******Price Reduction******239 Chestnut Street is a charming rancher in the heart of Winchester. 2 bedrooms, 1 bath, a large rear deck, eat in kitchen, laundry room could be converted into a third bedroom. Building in the back yard could be used as storage or a 1 car garage. This is a solid starter or downsizing home convenient to shopping,schools and parks. A little TLC will go a long way

  William Wertz Wildhawks Realty LLC

  239 Chestnut St, Winchester, VA 22601
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  /11

  $1,700 per month

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Condo for Rent

  302 N Kent St, Winchester, VA 22601

  Experience the charm of this beautifully renovated 3-bedroom, 2-bathroom Colonial apartment, set to unveil in 2025. Nestled in a serene environment, this unit boasts a timeless brick exterior and a thoughtfully designed layout that exudes warmth and comfort. Enjoy the convenience of in-unit washer and dryer hookups, ensuring effortless laundry days. The property offers an exclusive lifestyle with

  Brandon Pifer Pifer Realty, LLC

  302 N Kent St, Winchester, VA 22601
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  /59

  $640,000 Sold Nov 24, 2025

  150 Harvest Ridge Dr, Winchester, VA 22601

  • 4 Beds
  • 3 Baths
  • 4,385 Sq Ft
  • Built 2005

  Last Sold Summary

  • $146/SF
  • 54 Days On Market

  Last Listing Agent Bridget Aikens Colony Realty

  150 Harvest Ridge Dr, Winchester, VA 22601
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  /5

  Est $428,714 Not Listed For Sale

  329 Longview Ave, Winchester, VA 22601

  329 Longview Ave, Winchester, VA 22601

Showing Results 401 - 440, Page 11 of 18