Winchester, VA Homes

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  /69

  $605,000

  • Studio
  • 4,396 Sq Ft

  540 Monticello St, Winchester, VA 22601

  Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location!Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers

  Laura King MarketPlace REALTY

  540 Monticello St, Winchester, VA 22601
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  /46

  $2,150 per month

  • 2 Beds
  • 2 Baths
  • 1,024 Sq Ft
  • Condo for Rent

  1310 Ramseur Ln, Winchester, VA 22601

  Price Reduced + Owners will consider furnishing for the right tenant!! This 2 bedroom, 2 bath condo has been upgraded with all new plank flooring, new SS appliances in the kitchen, a new counter, upgraded bathrooms, plus a new stack washer/dryer unit. Every room has 9' + ceilings with crown molding and the master bedroom has a nice walk-in closet for all your essentials! For extra storage,

  Cindy Butler Virginia Property Group, Inc.

  1310 Ramseur Ln, Winchester, VA 22601
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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 $391,275

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

  102 Berkshire Cir, Winchester, VA 22601
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  /39

  Est $436,263 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,560 Sq Ft

  421 Longview Ave, Winchester, VA 22601

  421 Longview Ave, Winchester, VA 22601
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  /98

  $419,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,325 Sq Ft

  1133 Tomahawk Trail, Winchester, VA 22602

  Nestled in the serene Shawneeland community, this exquisite chalet-style residence offers a perfect blend of rustic charm and modern comfort. Set against a backdrop of breathtaking mountain views and scenic vistas, this home is a sanctuary for those seeking tranquility and an exclusive lifestyle. As you approach the property, the warm cedar exterior invites you in, exuding a sense of timeless

  Sue Goodwin Long & Foster Real Estate, Inc.

  1133 Tomahawk Trail, Winchester, VA 22602
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  /19

  $1,850 per month

  • 3 Beds
  • 2.5 Baths
  • 1,488 Sq Ft
  • Townhouse for Rent

  127 Lighthouse Ln, Winchester, VA 22602

  Location, Location, Location!!! This 3 level townhome features 3 bedrooms, 2 1/2 baths, large eat-in country kitchen with pantry, living room, office and garage with auto-opener. All appliances included. There is a deck off the dining area. Primary bedroom has full bath and walk-in closet. Community amenities include fenced pool and mowing. Landlord pays the HOA Fee. Non smoking. No Pets. Renters

  Barbara Gaul Jim Barb Realty, Inc.

  127 Lighthouse Ln, Winchester, VA 22602
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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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  /38

  Est $447,831 Not Listed For Sale

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

  425 Longview Ave, Winchester, VA 22601

  425 Longview Ave, Winchester, VA 22601
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  /20

  $439,900 New Construction

  • 3 Beds
  • 3 Baths
  • 1,935 Sq Ft

  109 Glenridge Dr, Winchester, VA 22602

  New construction! Pictures are if similar model. Conveniently located just minutes from town, this home offers comfort and style. With 3 bedrooms and 3 full baths, you will find many features such as beautiful hardwood floors throughout the main level, primary bedroom with walk in closet and bath with walk in shower, crown molding, granite counter top, 2 car garage and so much more! Don't miss

  Pamela Russell CENTURY 21 New Millennium

  109 Glenridge Dr, Winchester, VA 22602
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  /31

  $1,950 per month

  • 3 Beds
  • 2.5 Baths
  • 1,220 Sq Ft
  • Townhouse for Rent

  290 Sage Cir, Winchester, VA 22603

  Welcome Home! This move-in ready end-unit townhome in Regents Crest sits on a desirable corner lot with a larger yard that backs to a wooded nature path and walking trail for extra privacy. Offering 3 bedrooms, 2.5 baths, and a 1-car garage, this bright and open home is designed for comfort and convenience. The entry level includes a welcoming foyer with a large coat closet, garage access, and an

  Rachel Olsen Keller Williams Realty

  290 Sage Cir, Winchester, VA 22603
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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 $587,485

  Last Listing Agent Sarah Reynolds Keller Williams Realty

  2532 Middle Rd, Winchester, VA 22601
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  /33

  Est $430,385 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,366 Sq Ft

  417 Circle Dr, Winchester, VA 22601

  417 Circle Dr, Winchester, VA 22601
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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 Corcoran McEnearney

  158.5 Acres Lot 3 Laurel Grove Rd, Winchester, VA 22602
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  /58

  $3,000 per month

  • 4 Beds
  • 3 Baths
  • 3,060 Sq Ft
  • House for Rent

  209 N Washington St, Winchester, VA 22601

  Live in the heart of historic Winchester! This beautifully maintained 1853 home on Washington Street offers more than just a place to live—it’s a lifestyle. With over 3,000 square feet of finished space, this one-of-a-kind rental blends timeless character with modern updates just blocks from the Old Town Walking Mall and steps from the Apple Blossom Parade Route. Inside, you’ll find 10-foot

  Chris Roszko Colony Realty

  209 N Washington 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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  /35

  Est $390,971 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,508 Sq Ft

  416 Superior Ave, Winchester, VA 22601

  416 Superior Ave, Winchester, VA 22601
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  /16

  $400,000

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

  123 Etnam St, Winchester, VA 22602

  Come see this beautiful home located just off of Rt 50 to the East side of Winchester, great location for commuters, 4br, 2.5 bath with lots of room and storage space. Fenced in backyard with nice 20x16 deck and 8x10 additional deck space off of that for great entertaining. Call agent for combo to visit this listing.

  Heather Sutphin Coldwell Banker Realty

  123 Etnam St, Winchester, VA 22602
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  /15

  $1,750 per month

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

  307 Willowbrook Ct, Winchester, VA 22602

  Located in the highly sought-after East End of Winchester, this exceptional all-brick end-unit townhome is just minutes from Rt. 7 and I-81, offering an unbeatable commuter location. Close to shopping and only a short drive to the charming downtown Winchester walking mall, this home is perfectly positioned for convenience and comfort.Meticulously maintained by the owners, this move-in ready

  Jeff Boppe Long & Foster Real Estate, Inc.

  307 Willowbrook Ct, Winchester, VA 22602
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  /43

  $420,000 Sold Nov 14, 2025

  2808 Saratoga Dr, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 2,018 Sq Ft
  • Built 2002

  Last Sold Summary

  • $208/SF
  • 24 Days On Market

  Last Listing Agent Dave Spence RE/MAX Roots

  2808 Saratoga Dr, Winchester, VA 22601
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  /36

  Est $513,341 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,600 Sq Ft

  2816 Baldwin St, Winchester, VA 22601

  2816 Baldwin St, Winchester, VA 22601
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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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  /27

  $2,100 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  210 E Boscawen St Unit 203, Winchester, VA 22601

  This one bedroom and one bath apartment overlooks the roof onto Vibrissa's beautiful courtyard and mural. You will have a front row seat to live music and super quick access to tons of Apple Blossom events! Easy to clean and maintain LVP flooring has been installed throughout. The kitchen features a beautiful island, tons of cabinet space, with plenty of drawers for easy organizing, and stainless

  Katie Landi Jordan Samson Properties

  210 E Boscawen St Unit 203, Winchester, VA 22601
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  /75

  $1,071,134 Sold Jul 31, 2025

  220 Anna Margaret Dr, Winchester, VA 22602

  • 4 Beds
  • 5 Baths
  • 5,000 Sq Ft
  • Built 2006

  Last Sold Summary

  • $214/SF
  • 1 Day On Market

  Current Estimated Value $1,044,705

  Last Listing Agent Bradley Comstock ERA Oakcrest Realty, Inc.

  220 Anna Margaret Dr, Winchester, VA 22602
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  /52

  Est $413,573 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,702 Sq Ft

  209 W Cedarmeade Ave, Winchester, VA 22601

  209 W Cedarmeade Ave, Winchester, VA 22601
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  /13

  $235,000

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  129 Brookland Terrace Unit 1, Winchester, VA 22602

  Great two bedroom ,two bath condo. Very convenient first floor entrance. Zero steps. Great commuter location off Rt. 7

  John Scully Colony Realty

  129 Brookland Terrace Unit 1, Winchester, VA 22602
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  /13

  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Condo for Rent

  5 Brookland Ct, Winchester, VA 22602

  Well maintained 2 bedroom 2 bath unit on 2nd floor. Gas fireplace and private balcony. Ready for move in. Landlord requires Minimum credit score of 700 and income of 3X the rent. Pets are welcome case by case. No prior evictions. Apply online using RentSpree link. All adults over 18 must apply $35 application fee per applicant.

  Hushai Mesfin Samson Properties

  5 Brookland Ct, Winchester, VA 22602
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  /58

  $445,000 Sold Dec 09, 2025

  125 Alliance Ct, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 2,176 Sq Ft
  • Built 2021

  Last Sold Summary

  • $205/SF
  • 6 Days On Market

  Last Listing Agent Rhonda Shade ERA Oakcrest Realty, Inc.

  125 Alliance Ct, Winchester, VA 22602
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  /53

  Est $477,055 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,518 Sq Ft

  102 Russelcroft Rd, Winchester, VA 22601

  102 Russelcroft Rd, Winchester, VA 22601
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  /37

  $629,990 New Construction

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

  111 Scented Rose 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

  D.R. Horton Builder

  111 Scented Rose Way, Winchester, VA 22602
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  /2

  $1,270 per month

  • 1 Bed
  • 1 Bath
  • 3,324 Sq Ft
  • Condo for Rent

  545 N Loudoun St Unit 6, Winchester, VA 22601

  Come check out this great 1 Bedroom upper apartment located in the heart of historic Winchester, VA. This cozy 1 bedroom, 1 bathroom unit offers comfortable living with the convenience of all utilities included. The apartment is pet friendly on a case-by-case basis, with an additional pet deposit and monthly pet fee. Utilities are included in Monthly Rent Total. A credit and background check are

  Robert Adams Weichert Realtors - Blue Ribbon

  545 N Loudoun St Unit 6, Winchester, VA 22601
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  /60

  $400,000 Sold Aug 26, 2025

  319 Beechcroft Rd, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 2,538 Sq Ft
  • Built 1961

  Last Sold Summary

  • $158/SF
  • 4 Days On Market

  Current Estimated Value $402,814

  Last Listing Agent Gidget Smallwood Coldwell Banker Premier

  319 Beechcroft Rd, Winchester, VA 22601
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  /27

  Est $332,425 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  2939 S Pleasant Valley Rd, Winchester, VA 22601

  2939 S Pleasant Valley Rd, Winchester, VA 22601
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  /34

  $399,000

  • 4 Beds
  • 1.5 Baths
  • 1,953 Sq Ft

  318 E Piccadilly St, Winchester, VA 22601

  This delightful brick Colonial, perfectly situated in the heart of downtown Winchester, combines classic architecture with modern updates and an unbeatable location close to every downtown amenity, including restaurants, schools, shopping, parks, and major commuter routes. The home welcomes you with a large foyer featuring newly refinished hardwood floors that extend throughout the entire

  Dan Whitacre Colony Realty

  318 E Piccadilly St, Winchester, VA 22601
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  /10

  $1,525 per month

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Condo for Rent

  3 Brookland Ct, Winchester, VA 22602

  Amy Emerson-Kerns Cambridge Premier Realty, LLC.

  3 Brookland Ct, Winchester, VA 22602
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  /28

  $310,000 Sold Feb 14, 2025

  634 Battle Ave, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 954 Sq Ft
  • Built 1961

  Last Sold Summary

  • $325/SF
  • 3 Days On Market

  Current Estimated Value $312,177

  Last Listing Agent Mike Webber EXP Realty, LLC

  634 Battle Ave, Winchester, VA 22601
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  /22

  Est $335,705 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  2935 S Pleasant Valley Rd, Winchester, VA 22601

  2935 S Pleasant Valley Rd, Winchester, VA 22601
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  /41

  $485,000

  • 4 Beds
  • 3.5 Baths
  • 3,884 Sq Ft

  700 Crow Dr, Winchester, VA 22602

  Motivated Sellers!!! willing to negotiate a reasonable offer. Welcome to 700 Crow Drive, situated in the beautiful Wilde Acres subdivision in Frederick County, VA. This lovingly cared for and well-maintained three-level colonial home offers four bedrooms and three and a half baths, showcasing both space and style throughout. Priced below the tax assessment, this home presents an incredible

  Deisi Hernandez Fairfax Realty Select

  700 Crow Dr, Winchester, VA 22602
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  /17

  $1,600 per month

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft
  • Townhouse for Rent

  108 Hunter Run Rd, Winchester, VA 22602

  Move In Ready! Immaculate fully renovated 2 bedroom 1.5 bath townhouse in excellent commuter's location. Easy access to route 7 and I-81, VA-37, US-522/US-50. Eat-in kitchen with new cabinets, new granite countertops and new SS appliances. Beautiful refinished hardwood floors in living room and bedrooms and new waterproof laminate in kitchen, half bath and laundry room. New updated Full bath has

  Melissa Gallo Pearson Smith Realty, LLC

  108 Hunter Run Rd, Winchester, VA 22602
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  /33

  $607,990 Sold Nov 05, 2025

  • 2,511 Sq Ft
  • $242/SF

  • 5 Beds
  • 3 Baths
  • Built 2025

  111 Mascouten St, Winchester, VA 22602

  The Hayden is a three-story plan with 6 bedrooms and 4 bathrooms in 3,205 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 level. The

  D.R. Horton

  111 Mascouten St, Winchester, VA 22602
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  /19

  Est $331,257 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  2927 S Pleasant Valley Rd, Winchester, VA 22601

  2927 S Pleasant Valley Rd, Winchester, VA 22601

Showing Results 441 - 480, Page 12 of 18