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Winchester, VA - homes for sale
114 of 114 results displayed
- Coming Soon
$329,000Coming Soon-- beds -- baths419 Stone Meadow Ct, WINCHESTER, VA 22601
MLS# VAWI2010244Listed by: SAMSON PROPERTIES - New
$675,000Active3 beds 3 baths1,650 sq. ft.112 W Germain St, WINCHESTER, VA 22601
MLS# VAWI2010276Listed by: RE/MAX ROOTS - Coming Soon
$445,000Coming Soon3 beds 3 baths413 George St, WINCHESTER, VA 22601
MLS# VAWI2010236Listed by: PEARSON SMITH REALTY, LLC - New
$240,000Active3 beds 2 baths1,072 sq. ft.112 Star Fort Dr, WINCHESTER, VA 22601
MLS# VAFV2040626Listed by: LONG & FOSTER REAL ESTATE, INC. - Coming Soon
$619,900Coming Soon4 beds 3 baths329 Wood Ave, WINCHESTER, VA 22601
MLS# VAWI2010268Listed by: MARKETPLACE REALTY - Coming Soon
$320,000Coming Soon3 beds 1 baths2912 2nd St, WINCHESTER, VA 22601
MLS# VAWI2010242Listed by: PRESLEE REAL ESTATE - Coming Soon
$400,000Coming Soon5 beds 2 baths605 Dunlap St, WINCHESTER, VA 22601
MLS# VAWI2010260Listed by: SPRING HILL REAL ESTATE, LLC. - New
$585,000Active3 beds 3 baths3,000 sq. ft.308 Ridge Ave, WINCHESTER, VA 22601
MLS# VAWI2010158Listed by: COLONY REALTY - Coming Soon
$349,900Coming Soon3 beds 2 baths113 Christopher Dr, WINCHESTER, VA 22601
MLS# VAWI2010188Listed by: ERA OAKCREST REALTY, INC. - New
$360,000Active3 beds 3 baths1,600 sq. ft.16 S Pleasant Valley Rd, WINCHESTER, VA 22601
MLS# VAWI2010240Listed by: SAMSON PROPERTIES - New
$250,000Active3 beds 2 baths1,008 sq. ft.514 Cather Ave, WINCHESTER, VA 22601
MLS# VAWI2010238Listed by: EXP REALTY, LLC - Coming Soon
$525,000Coming Soon4 beds 2 baths823 Woodland Ave, WINCHESTER, VA 22601
MLS# VAWI2010234Listed by: COLDWELL BANKER REALTY - Coming Soon
$330,000Coming Soon4 beds 2 baths805 S Kent St, WINCHESTER, VA 22601
MLS# VAWI2010216Listed by: WEICHERT, REALTORS - New
$585,000Active4 beds 3 baths2,909 sq. ft.328 Sheridan Ave, WINCHESTER, VA 22601
MLS# VAWI2010174Listed by: DREAM REAL ESTATE - New
$385,000Active3 beds 2 baths1,450 sq. ft.540 Eagle Pl, WINCHESTER, VA 22601
MLS# VAWI2010212Listed by: NEXTHOME REALTY SELECT 
$399,000Active3 beds 2 baths1,999 sq. ft.520 N Braddock St, WINCHESTER, VA 22601
MLS# VAWI2010142Listed by: MARKETPLACE REALTY
$339,000Active3 beds 1 baths1,699 sq. ft.2956 Grace St, WINCHESTER, VA 22601
MLS# VAWI2010184Listed by: SAMSON PROPERTIES
$369,990Active3 beds 4 baths1,784 sq. ft.213 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2010200Listed by: DRB GROUP REALTY, LLC
$424,500Pending4 beds 3 baths1,805 sq. ft.21 W Pall Mall St, WINCHESTER, VA 22601
MLS# VAWI2010202Listed by: COMPASS
$349,900Pending4 beds 2 baths2,194 sq. ft.647 Battle Ave, WINCHESTER, VA 22601
MLS# VAWI2010146Listed by: EXP REALTY, LLC
$270,000Pending2 beds 2 baths1,024 sq. ft.2640 Limestone Ct, WINCHESTER, VA 22601
MLS# VAWI2010196Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
$295,000Active2 beds 2 baths864 sq. ft.704 Watson Ave, WINCHESTER, VA 22601
MLS# VAWI2010194Listed by: SAMSON PROPERTIES
$289,900Pending4 beds 3 baths1,530 sq. ft.2963 Sorrell Ct, WINCHESTER, VA 22601
MLS# VAWI2010192Listed by: RE/MAX REAL ESTATE CONNECTIONS
$429,000Active3 beds 3 baths1,528 sq. ft.209 Wood Ave, WINCHESTER, VA 22601
MLS# VAWI2010178Listed by: COLONY REALTY
$1,200,000Active6 beds 5 baths6,682 sq. ft.217 W Boscawen St, WINCHESTER, VA 22601
MLS# VAWI2010180Listed by: COLDWELL BANKER PREMIER
$389,990Active4 beds 3 baths1,536 sq. ft.317 Gray Ave, WINCHESTER, VA 22601
MLS# VAWI2008962Listed by: KELLER WILLIAMS REALTY
$625,000Pending3 beds 3 baths2,722 sq. ft.130 Morgan St, WINCHESTER, VA 22601
MLS# VAWI2010148Listed by: JIM BARB REALTY INC.
$280,000Active3 beds 2 baths1,020 sq. ft.320 Opequon Ave, WINCHESTER, VA 22601
MLS# VAWI2010088Listed by: RE/MAX ROOTS
$389,990Active3 beds 4 baths1,784 sq. ft.201 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2010156Listed by: DRB GROUP REALTY, LLC
$389,990Active3 beds 4 baths1,784 sq. ft.221 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2010162Listed by: DRB GROUP REALTY, LLC
$337,000Pending3 beds 2 baths1,280 sq. ft.19 W Germain St, WINCHESTER, VA 22601
MLS# VAWI2010060Listed by: MARKETPLACE REALTY
$759,000Pending6 beds 3 baths4,260 sq. ft.705 Treys Dr, WINCHESTER, VA 22601
MLS# VAWI2010152Listed by: ERA OAKCREST REALTY, INC.
$579,900Active4 beds 2 baths2,837 sq. ft.1317 Caroline St, WINCHESTER, VA 22601
MLS# VAWI2010126Listed by: COLONY REALTY
$399,900Active2 beds 2 baths1,405 sq. ft.1851 Melvor Ln, WINCHESTER, VA 22601
MLS# VAWI2010102Listed by: RE/MAX ROOTS
$399,000Active3 beds 3 baths2,338 sq. ft.3138 Eton Pl, WINCHESTER, VA 22601
MLS# VAWI2010130Listed by: REALTY FC
$360,000Active3 beds 2 baths1,260 sq. ft.101 Molden Dr, WINCHESTER, VA 22601
MLS# VAWI2009338Listed by: MARKETPLACE REALTY
$95,000Pending0.2 Acres816 Allen Dr, WINCHESTER, VA 22601
MLS# VAWI2009340Listed by: MARKETPLACE REALTY
$499,000Pending4 beds 3 baths2,068 sq. ft.2510 Windwood Dr, WINCHESTER, VA 22601
MLS# VAWI2010122Listed by: REALTY ONE GROUP OLD TOWNE
$215,000Active0.36 Acres506 Fairmont Ave, WINCHESTER, VA 22601
MLS# VAWI2010144Listed by: COLONY REALTY
$419,000Active4 beds 2 baths1,432 sq. ft.115 E Monmouth St, WINCHESTER, VA 22601
MLS# VAWI2010138Listed by: INMOBILIARIA DE LAS CASAS LLC
$649,999Active4 beds 3 baths3,157 sq. ft.153 Harvest Ridge Dr, WINCHESTER, VA 22601
MLS# VAFV2040020Listed by: HOMECOIN.COM
$314,900Active3 beds 1 baths1,086 sq. ft.126 S Euclid Ave, WINCHESTER, VA 22601
MLS# VAWI2010132Listed by: SAMSON PROPERTIES
$299,900Active3 beds 1 baths1,204 sq. ft.625 Watson Ave, WINCHESTER, VA 22601
MLS# VAWI2010098Listed by: RE/MAX ROOTS
$250,000Active2 beds 2 baths1,064 sq. ft.523 Monticello St, WINCHESTER, VA 22601
MLS# VAWI2010120Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
$275,000Active2 beds 1 baths720 sq. ft.719 Smithfield Ave, WINCHESTER, VA 22601
MLS# VAFV2039748Listed by: NEXTHOME REALTY SELECT
$269,000Pending2 beds 2 baths897 sq. ft.939 Woodland Ave, WINCHESTER, VA 22601
MLS# VAWI2010076Listed by: ROBERTS REALTY GROUP, LLC
$429,000Pending3 beds 2 baths2,648 sq. ft.1332 Ramseur Ln, WINCHESTER, VA 22601
MLS# VAWI2010104Listed by: RE/MAX ROOTS
$475,000Pending5 beds 3 baths2,890 sq. ft.411 Van Fossen St, WINCHESTER, VA 22601
MLS# VAWI2010068Listed by: MARKETPLACE REALTY
$675,000Pending5 beds 4 baths3,294 sq. ft.200 & 210 W Fairfax Ln, WINCHESTER, VA 22601
MLS# VAWI2010072Listed by: COLONY REALTY
$499,990Pending2 beds 2 baths1,850 sq. ft.411-302 N Loudoun St, WINCHESTER, VA 22601
MLS# VAWI2009780Listed by: REALTY ONE GROUP OLD TOWNE
$439,000Active4 beds 2 baths1,400 sq. ft.743 Berryville Ave, WINCHESTER, VA 22601
MLS# VAWI2010062Listed by: PEARSON SMITH REALTY, LLC- Open Sat, 1 to 3pm
$459,000Active6 beds 3 baths1,552 sq. ft.2250 Roosevelt Blvd, WINCHESTER, VA 22601
MLS# VAWI2010064Listed by: SAMSON PROPERTIES 
$335,000Pending2 beds 2 baths1,684 sq. ft.601 Hollingsworth Dr, WINCHESTER, VA 22601
MLS# VAWI2010058Listed by: COLDWELL BANKER PREMIER
$640,000Pending6 beds 4 baths3,192 sq. ft.162 Omps Dr, WINCHESTER, VA 22601
MLS# VAWI2010030Listed by: LONG & FOSTER REAL ESTATE, INC.
$409,900Pending3 beds 2 baths1,764 sq. ft.320 E Piccadilly St, WINCHESTER, VA 22601
MLS# VAWI2010018Listed by: COLONY REALTY
$310,000Pending3 beds 1 baths1,118 sq. ft.423 Shenandoah Pl, WINCHESTER, VA 22601
MLS# VAWI2010016Listed by: KELLER WILLIAMS REALTY/LEE BEAVER & ASSOC.
$245,000Pending2 beds 3 baths1,280 sq. ft.2967 Sorrell Ct, WINCHESTER, VA 22601
MLS# VAWI2010008Listed by: TRECK REALTY LLC
$474,900Pending4 beds 3 baths2,100 sq. ft.620 Crystal Ct, WINCHESTER, VA 22601
MLS# VAWI2010000Listed by: REALTY FC
$265,000Pending3 beds 2 baths1,144 sq. ft.106 W Southwerk St, WINCHESTER, VA 22601
MLS# VAWI2009996Listed by: ERA OAKCREST REALTY, INC.
$399,990Pending3 beds 4 baths1,784 sq. ft.234 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2009986Listed by: DRB GROUP REALTY, LLC
$1,100,000Active2.3 AcresPleasant Valley, WINCHESTER, VA 22601
MLS# VAFV2039602Listed by: COLDWELL BANKER PREMIER
$500,000Active4 beds 4 baths2,524 sq. ft.2643 Middle Rd, WINCHESTER, VA 22601
MLS# VAWI2009924Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
$549,900Pending4 beds 3 baths2,234 sq. ft.1917 Harvest Dr, WINCHESTER, VA 22601
MLS# VAWI2009976Listed by: SAMSON PROPERTIES
$379,990Active3 beds 4 baths1,784 sq. ft.218 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2009978Listed by: DRB GROUP REALTY, LLC- Open Sat, 12 to 3pm
$419,990Active4 beds 4 baths1,920 sq. ft.1813 Harvest Dr, WINCHESTER, VA 22601
MLS# VAWI2009964Listed by: D R HORTON REALTY OF VIRGINIA LLC 
$399,990Pending4 beds 4 baths1,920 sq. ft.1821 Harvest Dr, WINCHESTER, VA 22601
MLS# VAWI2009960Listed by: D R HORTON REALTY OF VIRGINIA LLC
$735,000Active4 beds 3 baths3,482 sq. ft.1419 Ramseur Ln, WINCHESTER, VA 22601
MLS# VAWI2009932Listed by: RE/MAX ROOTS
$449,000Active3 beds 3 baths1,904 sq. ft.25 W Southwerk St, WINCHESTER, VA 22601
MLS# VAWI2009902Listed by: COLONY REALTY
$889,000Pending5 beds 5 baths4,957 sq. ft.1540 Meadow Branch Ave, WINCHESTER, VA 22601
MLS# VAWI2009860Listed by: COLONY REALTY
$389,900Pending2 beds 2 baths1,550 sq. ft.1885 Rosser Ln, WINCHESTER, VA 22601
MLS# VAWI2009918Listed by: OLIVETREE PROPERTY GROUP
$349,900Pending3 beds 1 baths1,196 sq. ft.249 West Street St, WINCHESTER, VA 22601
MLS# VAWI2009908Listed by: LONG & FOSTER REAL ESTATE, INC.
$250,000Pending2 beds 2 baths780 sq. ft.2519 Hockman Ave, WINCHESTER, VA 22601
MLS# VAWI2009854Listed by: HOFFMAN REALTY
$650,000Active4 beds 4 baths3,474 sq. ft.132 Amherst St, WINCHESTER, VA 22601
MLS# VAWI2009872Listed by: COLONY REALTY
$80,000Active0.13 Acres520 Highland Ave, WINCHESTER, VA 22601
MLS# VAWI2009882Listed by: SAMSON PROPERTIES
$80,000Active0.08 Acres24 N Pleasant Valley Rd, WINCHESTER, VA 22601
MLS# VAWI2009884Listed by: SAMSON PROPERTIES
$465,000Active3 beds 3 baths2,293 sq. ft.3137 Eton Pl, WINCHESTER, VA 22601
MLS# VAWI2009840Listed by: ERA OAKCREST REALTY, INC.- Open Sat, 11:30am to 1:30pm
$479,900Active3 beds 3 baths1,992 sq. ft.703 S Loudoun St, WINCHESTER, VA 22601
MLS# VAWI2009838Listed by: SAMSON PROPERTIES 
$175,000Active0.37 Acres719 Kennedy Dr, WINCHESTER, VA 22601
MLS# VAWI2009810Listed by: COLONY REALTY
$550,000Active3 beds 2 baths1,974 sq. ft.832 Winder Ct, WINCHESTER, VA 22601
MLS# VAWI2009800Listed by: REALTY ONE GROUP OLD TOWNE
$320,000Pending4 beds 2 baths1,344 sq. ft.1610 S. Loudoun St, WINCHESTER, VA 22601
MLS# VAWI2009664Listed by: SAMSON PROPERTIES
$199,900Active0.16 Acres1415 Ramseur Ln, WINCHESTER, VA 22601
MLS# VAWI2009784Listed by: COLDWELL BANKER PREMIER
$419,900Pending3 beds 2 baths2,219 sq. ft.945 Allen Dr, WINCHESTER, VA 22601
MLS# VAWI2009776Listed by: REALTY ONE GROUP OLD TOWNE
$389,990Pending3 beds 4 baths1,784 sq. ft.214 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2009620Listed by: DRB GROUP REALTY, LLC
$347,500Pending3 beds 1 baths907 sq. ft.217 Myrtle Ave, WINCHESTER, VA 22601
MLS# VAWI2009772Listed by: REALTY ONE GROUP OLD TOWNE
$464,900Pending4 beds 3 baths1,960 sq. ft.418 Circle Dr, WINCHESTER, VA 22601
MLS# VAWI2009680Listed by: SAMSON PROPERTIES
$384,900Active2 beds 2 baths1,186 sq. ft.711 E Cork St, WINCHESTER, VA 22601
MLS# VAWI2009596Listed by: SPRING HILL REAL ESTATE, LLC.
$559,900Pending4 beds 3 baths2,644 sq. ft.436 Westside Station Dr, WINCHESTER, VA 22601
MLS# VAFV2038424Listed by: SAMSON PROPERTIES
$468,180Pending3 beds 3 baths2,805 sq. ft.407 Jefferson St, WINCHESTER, VA 22601
MLS# VAWI2009590Listed by: COLDWELL BANKER PREMIER
$409,990Active4 beds 4 baths1,920 sq. ft.1805 Harvest Dr, WINCHESTER, VA 22601
MLS# VAWI2009538Listed by: D R HORTON REALTY OF VIRGINIA LLC
$419,990Pending4 beds 4 baths1,939 sq. ft.1817 Harvest Dr, WINCHESTER, VA 22601
MLS# VAWI2009540Listed by: D R HORTON REALTY OF VIRGINIA LLC
$265,000Pending2 beds 1 baths882 sq. ft.204 Shenandoah Ave, WINCHESTER, VA 22601
MLS# VAWI2009534Listed by: KELLER WILLIAMS REALTY
$279,000Pending3 beds 1 baths907 sq. ft.208 Shenandoah Ave, WINCHESTER, VA 22601
MLS# VAWI2009462Listed by: COLONY REALTY
$330,000Pending3 beds 1 baths1,237 sq. ft.117 W Oates Ave, WINCHESTER, VA 22601
MLS# VAWI2009446Listed by: REALTY ONE GROUP OLD TOWNE
$430,000Active4 beds 2 baths2,100 sq. ft.17 E Leicester St, WINCHESTER, VA 22601
MLS# VAWI2009350Listed by: MARKETPLACE REALTY
$605,000Active7 beds -- baths4,396 sq. ft.540 Monticello St, WINCHESTER, VA 22601
MLS# VAWI2009974Listed by: MARKETPLACE REALTY
$371,990Pending3 beds 4 baths1,784 sq. ft.210 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2009246Listed by: DRB GROUP REALTY, LLC
$369,990Pending4 beds 4 baths1,784 sq. ft.206 Monteith Dr, WINCHESTER, VA 22601
MLS# VAWI2009244Listed by: DRB GROUP REALTY, LLC
$269,900Active2 beds 1 baths870 sq. ft.1125 Conway St, WINCHESTER, VA 22601
MLS# VAWI2009200Listed by: ERA OAKCREST REALTY, INC.
$414,900Active3 beds 3 baths1,251 sq. ft.709 Ross St, WINCHESTER, VA 22601
MLS# VAFV2037236Listed by: SAMSON PROPERTIES
$414,900Active3 beds 3 baths1,251 sq. ft.713 Ross St, WINCHESTER, VA 22601
MLS# VAFV2037240Listed by: SAMSON PROPERTIES
$300,000Pending3 beds 2 baths1,072 sq. ft.112 Star Fort Dr, WINCHESTER, VA 22601
MLS# VAFV2037188Listed by: LONG & FOSTER REAL ESTATE, INC.
$654,000Active6 beds 4 baths3,511 sq. ft.1400 Valley Ave, WINCHESTER, VA 22601
MLS# VAWI2009108Listed by: REAL BROKER LLC
$389,990Active3 beds 4 baths1,784 sq. ft.Tbb Monteith Dr #bedford Ii, WINCHESTER, VA 22601
MLS# VAWI2009636Listed by: DRB GROUP REALTY, LLC
$358,000Pending4 beds 2 baths1,534 sq. ft.323 Russelcroft Rd, WINCHESTER, VA 22601
MLS# VAWI2009662Listed by: SPRING HILL REAL ESTATE, LLC.
$225,000Pending3 beds 2 baths1,526 sq. ft.369 Charles St, WINCHESTER, VA 22601
MLS# VAWI2008716Listed by: ERA OAKCREST REALTY, INC.
$335,000Active3 beds 3 baths1,536 sq. ft.1004 S Cameron St, WINCHESTER, VA 22601
MLS# VAWI2007970Listed by: METAS REALTY GROUP, LLC
$884,000Active5 beds 5 baths4,438 sq. ft.769 Seldon Dr, WINCHESTER, VA 22601
MLS# VAWI2009972Listed by: KELLER WILLIAMS REALTY
$985,000Active7 beds 6 baths6,540 sq. ft.1020 Breckinridge Ln, WINCHESTER, VA 22601
MLS# VAWI2007912Listed by: RE/MAX ROOTS
$750,000Pending1.33 Acres903 N Loudoun St, WINCHESTER, VA 22601
MLS# VAWI2007862Listed by: COLDWELL BANKER ELITE
$4,000,000Pending27.2 AcresNorth Frederick Pike, WINCHESTER, VA 22601
MLS# VAWI2007698Listed by: COLDWELL BANKER PREMIER
$4,500,000Pending11.43 Acres801 Fairmont Ave, WINCHESTER, VA 22601
MLS# VAWI2007696Listed by: COLDWELL BANKER PREMIER
$1,850,000Active12 beds -- baths7,190 sq. ft.908 Cedar Creek Grade, WINCHESTER, VA 22601
MLS# VAWI2007202Listed by: LINK REALTY SERVICES LLC
$449,000Active0.09 Acres1 N Braddock St, WINCHESTER, VA 22601
MLS# VAWI2005956Listed by: COLDWELL BANKER PREMIER
$2,300,000Active3.51 Acres1721 Amherst St, WINCHESTER, VA 22601
MLS# VAWI2008980Listed by: OAKCREST COMMERCIAL REAL ESTATE
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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.