Winchester, VA Homes for Sale under $400,000

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  /35

  $329,999

  $7K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 1,320 Sq Ft

  124 Worsham Terrace, Winchester, VA 22602

  Welcome to this beautifully maintained townhouse that offers the perfect blend of comfort, style, and convenience. Boasting an attractive full brick-front exterior with classic black shutters, this home offers timeless curb appeal and a welcoming first impression. The private driveway, attached one-car garage, and well-maintained landscaping add both functionality and charm.The main

  

  David Peña

  Corcoran McEnearney

  124 Worsham Terrace, Winchester, VA 22602
• Explore Winchester

• 

  

  

  /27

  $359,900

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft

  601 Gray Ave, Winchester, VA 22601

  Welcome to Gray Avenue! This beautifully updated 3-bedroom, 2-bath home offers over 1,700 square feet of stylish living space, blending timeless charm with modern finishes throughout.Rich hardwood floors flow throughout the home, creating warmth and character from the moment you step inside. The sun-filled living room feels bright and inviting, highlighted by a custom light fixture and a

  

  Walther Vasquez Johnson

  Samson Properties

  601 Gray Ave, Winchester, VA 22601
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  /44

  $350,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,230 Sq Ft

  117 E Pall Mall St, Winchester, VA 22601

  ** Price improvement!** Welcome home to 117 E Pall Mall St! Ideally located within a mile of Shenandoah University and historic downtown Winchester! This 3 bedroom, 2.5 bath has lots of updates and upgrades! Updated kitchen and baths, stainless steel appliances, & a fenced in backyard! 2023 - Roof, siding, & electrical panel (and all breakers), updated kitchen and all baths, 2024 - repaired sump

  

  Becky Wallace

  Pearson Smith Realty, LLC

  117 E Pall Mall St, Winchester, VA 22601
• 

  

  

  /3

  $339,000

  $11K PRICE DROP

  • Studio
  • 1,654 Sq Ft

  211, 213-215 E Clifford St, Winchester, VA 22601

  Exceptional investment opportunity in the heart of Winchester! This unique offering includes three income-producing rental units for one price: one duplex and one single-family home located at 211, 213, and 215 E. Clifford Street. The duplex features two separate 2-bedroom, 1-bath units, while the single-family home also offers 2 bedrooms and 1 full bath.The properties are deeded

  

  Rhonda Shade

  ERA Oakcrest Realty, Inc.

  211, 213-215 E Clifford St, Winchester, VA 22601
• 

  

  /2

  $195,000

  • 3 Beds
  • 1 Bath
  • 932 Sq Ft

  150 Cedar Grove Rd, Winchester, VA 22603

  This property is being sold strictly as-is, where-is. The mobile home on the property is believed to date back to the 1960s and is in need of significant renovation. Previous occupants began updating the home but did not complete the work. The property also features a garage-style building with a work bay and office space equipped with air conditioning, offering excellent potential for storage,

  

  Frank Armstrong, IV

  Colony Realty

  150 Cedar Grove Rd, Winchester, VA 22603
• 

  /2

  $175,000

  • Land
  • 16,117 Sq Ft
  • $472,973 per Acre

  719 Kennedy Dr, Winchester, VA 22601

  Vacant Lot in Rolling HillsOne of the last opportunities to own a vacant lot in the desirable Rolling Hills community. This property offers the perfect setting to build your new home or presents an excellent opportunity for a long-term investment. Enjoy a well-established neighborhood with limited remaining buildable lots. Buyer to verify zoning, utilities, and intended use. Water and Sewer

  

  Frank Armstrong, IV

  Colony Realty

  719 Kennedy Dr, Winchester, VA 22601
• 

  

  /17

  $125,000

  • 1 Bed
  • 1 Bath
  • 624 Sq Ft

  415 Puma Trail, Winchester, VA 22602

  Ranch cabin-style home nestled in the woods on a private 1⁄2-acre lot. Featuring 1-bedroom, additional room but not technically a bedroom, and 1 full bath, this property offers endless potential as a full-time residence, weekend retreat, or investment opportunity. Enjoy the tranquility of the wooded surroundings while remaining conveniently located just 25 minutes from Winchester. The home is

  

  Ken Evans

  RE/MAX Real Estate Connections

  415 Puma Trail, Winchester, VA 22602
• 

  

  /37

  $359,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  700 Green St, Winchester, VA 22601

  You've been dreaming of main-level living, and this is IT! Check all your boxes:3 bedrooms2 full bathroomsOpen-concept family roomBeautifully updated kitchenSpacious kitchen islandPrimary suite with private bath, walk-in shower, and walk-in closetCharming front porch - perfect for morning coffee��� Roof replaced 2018Private back deckFenced

  

  Jeanne Mezzatesta

  Colony Realty

  700 Green St, Winchester, VA 22601
• 

  

  /40

  $370,000

  • 4 Beds
  • 1.5 Baths
  • 1,588 Sq Ft

  1008 S Cameron St, Winchester, VA 22601

  Live just minutes from historic Old Town Winchester, where charming boutiques, local restaurants, and picturesque streets are all close at hand. This beautifully maintained two-story home seamlessly blends the timeless character of the 1930s with the modern updates today’s buyers appreciate.A classic covered front porch welcomes you home and offers the perfect place to enjoy your morning

  Nikola Tadie Redfin Corporation

  1008 S Cameron St, Winchester, VA 22601
• 

  

  /14

  $104,500

  • Land
  • 5.5 Acres
  • $19,000 per Acre

  0 Hodges Ln Unit LotWP013, Winchester, VA 22603

  Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home, including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

  Chad Pangle Whitetail Properties Real Estate

  0 Hodges Ln Unit LotWP013, Winchester, VA 22603
• 

  

  /20

  $154,650

  • Land
  • 12.9 Acres
  • $11,988 per Acre

  0 Hodges Ln Unit LotWP011, Winchester, VA 22603

  Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home, including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

  Chad Pangle Whitetail Properties Real Estate

  0 Hodges Ln Unit LotWP011, Winchester, VA 22603
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  /21

  $210,000

  • Land
  • 5 Acres
  • $42,000 per Acre

  0 Off of Mount Olive Rd Unit LotWP00B, Winchester, VA 22603

  Prime building lot conveniently located less than 10 minutes west of Winchester, with immediate access to US-50 - Northwestern Pike. Part of what was once the well-known Rotz Farm and is now part of the brand-new Ridgeview Glen community. This land is ideally positioned between scenic Flint Ridge and flowing Hogue Creek. This tract features a 4-bedroom septic certification letter, which is

  Chad Pangle Whitetail Properties Real Estate

  0 Off of Mount Olive Rd Unit LotWP00B, Winchester, VA 22603
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  /28

  $350,000

  • Land
  • 19.58 Acres
  • $17,875 per Acre

  Off of Dominion Rd Unit LotWP001, Winchester, VA 22603

  Open ground that is prime for investment, livestock, or to build your future home. Fully unrestricted, this property sits along the Virginia/West Virginia border but calls Virginia home. Accessed via a 50-foot-wide right of way from Dominion Road, a home site could be tucked back into the field, giving you privacy and mountain views. Along the front portion of the property is a patch of timber

  Drew Baggarly Whitetail Properties Real Estate

  Off of Dominion Rd Unit LotWP001, Winchester, VA 22603
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  /23

  $127,750

  • Land
  • 8.11 Acres
  • $15,752 per Acre

  0 Wolf Spring Trail Unit LotWP001, Winchester, VA 22602

  Rare opportunity to own three adjoining fully wooded parcels in the quiet and peaceful Shawneeland community. Numerous residential and recreational possibilities exist with ownership of these tracts. Located just a few miles west of Winchester in the Rosenberger area of the county. Access is secured via extensive road frontage on paved Wolf Spring Trail. Utilities are close by, making for easy

  Chad Pangle Whitetail Properties Real Estate

  0 Wolf Spring Trail Unit LotWP001, Winchester, VA 22602
• 

  

  /19

  $141,500

  • Land
  • 11.1 Acres
  • $12,748 per Acre

  0 Hodges Ln Unit LotWP014, Winchester, VA 22603

  Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home, including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

  Chad Pangle Whitetail Properties Real Estate

  0 Hodges Ln Unit LotWP014, Winchester, VA 22603
• 

  

  /23

  $349,990

  New Construction

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

  Northgate Plan at Hiatt Pointe at Snowden Bridge - 55+ Villas Collection, 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

  105 Wagtail Ln Unit 36578847, Winchester, VA 22603
• 

  

  /21

  $399,990

  New Construction $5K PRICE DROP

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

  134 Swansong Place, Winchester, VA 22603

  The three-level Skyline model masterfully combines a traditional exterior with a contemporary, open-concept floor plan. On the main level, you’ll find an expansive living room, bathed in natural light from numerous windows, flows effortlessly into the dining area and kitchen. The kitchen is designed with an L-shaped countertop and an island that borders the dining room. A cozy nook serves as a

  Brookfield Residential Builder

  134 Swansong Place, Winchester, VA 22603
• 

  

  /29

  $369,999

  Open Sat 12PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,387 Sq Ft

  2919 S Pleasant Valley Rd, Winchester, VA 22601

  Welcome to this adorable and beautifully refreshed Cape Cod, ideally located on a quiet street in Winchester City with no HOA! This move-in-ready home offers a comfortable and versatile floor plan, featuring a primary suite on the main level, plus two spacious bedrooms and a second full bathroom upstairs.Enjoy the peace of mind that comes with numerous recent updates and renovations completed

  Patricia Rivas Plata Keller Williams Realty Dulles

  2919 S Pleasant Valley Rd, Winchester, VA 22601
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  /22

  $269,000

  • Land
  • 42,253 Sq Ft
  • $277,320 per Acre

  823 Armistead St, Winchester, VA 22601

  *** Price shown is for lot only. Seller is willing to assist Buyer in building this beautiful home plandesigned by Seller customized for this lot and optimized for cost effective construction. Closingon the lot may occur upon issuance of the Building Permit in Buyer’s name by the City ofWinchester. ***This modern farmhouse style home includes 5,630 square feet of living space

  Janet Flaherty Keller Williams Realty

  823 Armistead St, Winchester, VA 22601
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  /48

  $389,999

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

  709 Dicks Hollow Rd, Winchester, VA 22603

  Exceptional value meets impeccable quality! From the bright, welcoming entryway to the beautifully crafted living spaces, every detail of this home speaks to superior craftsmanship. Perfect for discerning buyers seeking a flawless blend of style and convenience, this property presents a rare window of opportunity. Schedule your showing today and secure this incredible home before it’s gone!

  Fehiber Rosario NBI Realty, LLC

  709 Dicks Hollow Rd, Winchester, VA 22603
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  /2

  $215,000

  • Land
  • 26,571 Sq Ft
  • $352,459 per Acre

  40 Huntersridge Rd, Winchester, VA 22602

  A rare offering in the established Oakdale Crossing Community. This 0.61 acre-lot boasts a flat topography, tucked on a quiet cul-de-sac, and framed with large lush trees. Enjoy the perfect blend of seclusion and proximity with a short drive to the Winchester Country Club, Jim Barnett Park, Major shopping & dining, and the downtown walking mall. + prime location for commuters with easy access to

  Jocelyn Tweedie Hunt Country Sotheby's International Realty

  40 Huntersridge Rd, Winchester, VA 22602
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  /82

  $325,000

  $45K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,036 Sq Ft

  2431 Cedar Creek Grade, Winchester, VA 22602

  This is a unique opportunity to purchase a piece of history. The Glass Mill (Glass/Rinker/Cooper Mill) is available. The Mill was constructed during the years 1812-1815. At the base, the structure has stone walls that are 3' thick, tapering to about half that at the gable ends. The Mill has a "mechanics level", the lower level with dirt floor and water source when the Grist wheel was in place.

  Edward Beightol Cedar Creek Real Estate

  2431 Cedar Creek Grade, Winchester, VA 22602
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  /17

  $240,000

  • 2 Beds
  • 1 Bath
  • 997 Sq Ft

  187 Valley Mill Rd, Winchester, VA 22602

  Great investment opportunity for this centrally located rambler! Just minutes from Route 7 and I-81, this property offers convenient access to shopping, restaurants, and everyday amenities.The current tenant is under lease through 11/13/26, providing immediate rental income for an investor. With some sweat equity and a few updates, there is potential to increase the rental income

  Heloisa Amar Samson Properties

  187 Valley Mill Rd, Winchester, VA 22602
• 

  

  /14

  $104,500

  • Land
  • 5.5 Acres
  • $19,000 per Acre

  0 Hodges Lot 13 Ln, Winchester, VA 22603

  Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Hodges Lot 13 Ln, Winchester, VA 22603
• 

  

  /19

  $385,490

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  648 Arden Ct, Winchester, VA 22601

  648 Arden Court is an attractive new 3 level townhome backing to trees with brick in Winchester's premier Meadow Branch community for September move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, grey cabinets, and stainless-steel appliances.

  D.R. Horton Builder

  648 Arden Ct, Winchester, VA 22601
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  /38

  $370,000

  • 3 Beds
  • 2.5 Baths
  • 1,772 Sq Ft

  100 Stribling Way, Winchester, VA 22602

  Welcome to this bright and inviting end-unit townhome in Winchester! Additional windows fill the home with natural light, while the open layout creates an easy flow between the kitchen and living spaces, perfect for everyday living and entertaining. The kitchen features stainless steel appliances, and upstairs you’ll enjoy the convenience of laundry on the bedroom level. The walk-in level

  Raven Staub Samson Properties

  100 Stribling Way, Winchester, VA 22602
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  /41

  $400,000

  $25K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,952 Sq Ft

  206 Dogwood Rd, Winchester, VA 22602

  ...NEW PRICE....Welcome to 206 Dogwood Rd. Well maintained 5 Bedroom 2 Bath Cape Cod in a quiet neighborhood conveniently located a short distance from the downtown area. HVAC has just been installed..The house is on your own septic system. Sunroom with a laundry was added in 2007. An additional lot is included with this house.....Lot number #55-B-3-2-63 Lot 63 making the total area 1 acre. The

  William Wertz Wildhawks Realty LLC

  206 Dogwood Rd, Winchester, VA 22602
• 

  

  /15

  $110,000

  • Land
  • 6.42 Acres
  • $17,134 per Acre

  0 Pack Horse Road Lot C Unit VAFV2042708, Winchester, VA 22603

  The rural America many people desire is available on state maintained Pack Horse Road. There are 3 lots being sold separately and this 6.42 lot C is wooded, has septic already installed, has a Frederick County cert letter (see documents from health department however buyer should do due diligence). Unrestricted and so think about the possibilities for a homestead, simple get away to enjoy quiet

  Dave Spence RE/MAX Roots

  0 Pack Horse Road Lot C Unit VAFV2042708, Winchester, VA 22603
• 

  

  /22

  $399,999

  New Construction

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

  118 Nepal Ct, Winchester, VA 22602

  | Summer 2026 Delivery AvailableSt. Paul TBB | 4 BR | 3.5 BA | 1-Car Garage | Finished Lower Level + Larger DeckBeautiful wooded homesites available!Offering up to 2,000 sq. ft. of modern, open-concept livingHome HighlightsOpen-concept main level – perfect for entertainingGranite countertopsStainless steel appliancesLuxury vinyl plank flooringUpper

  Jimmy Thomas New Home Star Virginia, LLC

  118 Nepal Ct, Winchester, VA 22602
• 

  

  /19

  $389,160

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  171 Sioux Loop, Winchester, VA 22602

  This Adams interior unit features 4 bedrooms, 3.5 baths, and a 1-car garage. With a total of 1,889 sq. ft., there is plenty of space to entertain and live comfortably. Enjoy 9' ceilings and luxury vinyl plank flooring on the main level. The kitchen features gray cabinets with quartz countertops along with stainless steel appliances by Whirlpool. Relax on your 8'x14' rear deck and take advantage

  D.R. Horton Builder

  171 Sioux Loop, Winchester, VA 22602
• 

  

  /32

  $279,000

  • 2 Beds
  • 1.5 Baths
  • 1,590 Sq Ft

  261 Waterford Ln, Winchester, VA 22602

  Move-in ready and well maintained! This charming 2-bedroom, 1.5-bath townhome offers comfortable living with a spacious main-level living area, eat-in kitchen, and convenient laundry. The partially finished basement adds a large family room and plenty of storage, with walk-out access to a shaded patio and large, private fenced backyard. Relax on the back deck surrounded by mature trees, offering

  Liz Rutherford ERA Oakcrest Realty, Inc.

  261 Waterford Ln, Winchester, VA 22602
• 

  

  /23

  $349,990

  • 3 Beds
  • 2 Baths
  • 1,024 Sq Ft

  182 Mason St, Winchester, VA 22602

  Welcome to this adorable 3-bedroom, 2-full-bath cottage rancher home located on the East side of Winchester with NO HOA! Offering approximately 1,024 finished square feet on a generous .30-acre level lot, this property presents an excellent opportunity for both homeowners and investors.The home features an oversized two-car detached garage, providing plenty of room for vehicles, storage,

  Samantha Young Young & Associates

  182 Mason St, Winchester, VA 22602
• 

  

  /5

  $295,000

  Coming Soon Sep 12

  • 3 Beds
  • 1 Bath
  • 913 Sq Ft

  405 Shenandoah Ave, Winchester, VA 22601

  Ideally situated just minutes from I-81 and a short drive to historic Old Town Winchester, this centrally located rambler offers both convenience and investment potential. Situated on a desirable corner lot, the property features a fenced yard and a storage shed for added functionality.The home has been recently refreshed with new paint and landscaping, providing excellent curb appeal and

  Heloisa Amar Samson Properties

  405 Shenandoah Ave, Winchester, VA 22601
• 

  

  /30

  $400,000

  • 3 Beds
  • 2.5 Baths
  • 2,330 Sq Ft

  3135 Eton Place, Winchester, VA 22601

  Lofts at Creekside is one of the newest walkable communities in the city of Winchester with proximity to the upscale Creekside Station. Offering eateries, clothing stores, and professional services allows you to start or end your day at a plethora of local store fronts only steps from your home. Being only 2 years young allows the comfort of practically a new home in impeccable condition. Two car

  Dave Spence RE/MAX Roots

  3135 Eton Place, Winchester, VA 22601
• 

  

  /25

  $324,900

  New Construction

  • 2 Beds
  • 2.5 Baths
  • 1,152 Sq Ft

  212 Falcon Trail, Winchester, VA 22602

  House completed.1/3 Acre – No Carpet!This affordable 2-bed, 2.5-bath home offers high-end finishes and incredible growth potential.Premium Finishes: Hardwood floors throughout (including all bedrooms), tile in all baths, and granite kitchen countertops.Open Layout: Bright family room and a spacious kitchen/dining area perfect for entertaining.Owner’s Suite: Large master

  Jim Thomson Realty ONE Group Old Towne

  212 Falcon Trail, Winchester, VA 22602
• 

  

  /9

  $308,000

  • 2 Beds
  • 2 Baths
  • 800 Sq Ft

  2519 Hockman Ave, Winchester, VA 22601

  This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detached home offers a unique opportunity for investors seeking to capitalize on a revitalized property in a desirable location. With two spacious bedrooms and two full bathrooms, the layout is perfect for modern living. The full

  Meridee Powars Link Realty Services LLC

  2519 Hockman Ave, Winchester, VA 22601
• 

  

  /44

  $319,900

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  12 N Purcell Ave, Winchester, VA 22601

  Welcome to 12 N Purcell Ave, a classic white bungalow offering standout curb appeal, a well-kept lawn and landscaping, and an unbeatable central location. Relax on the covered front porch before stepping inside to a bright and inviting main level featuring rich hardwood floors and a spacious eat-in kitchen with plentiful cabinet space. Two sizable bedrooms and a full bath round out the main floor

  Dan Whitacre Colony Realty

  12 N Purcell Ave, Winchester, VA 22601
• 

  

  /31

  $379,900

  $19K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,909 Sq Ft

  527 Grouse Dr, Winchester, VA 22602

  Welcome to 527 Grouse Drive—almost new construction offering the perfect blend of modern finishes, functional living space, and peaceful mountain surroundings. This beautifully updated split foyer home features 3 bedrooms, 2.5 bathrooms, and over 1,900 finished square feet situated on a spacious lot.Open-concept layout filled with natural light, fresh paint throughout, updated light fixtures,

  Amanda Magana RE/MAX Roots

  527 Grouse Dr, Winchester, VA 22602
• 

  /2

  $385,000

  Coming Soon Sep 23

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  108 Williamson Rd, Winchester, VA 22602

  Coming soon in Winchester! Welcome to this beautifully maintained 3-bedroom, 2-bath brick rambler in a convenient location. This move-in-ready home offers comfortable one-level living and features an updated kitchen with quartz countertops and stainless steel appliances, updated bathrooms, attractive flooring throughout, and a detached side-entry garage. The current owner has carefully maintained

  Nathalie Acosta Spring Hill Real Estate, LLC.

  108 Williamson Rd, Winchester, VA 22602
• 

  

  /52

  $399,000

  $26K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,799 Sq Ft

  437 Beechcroft Rd, Winchester, VA 22601

  PRICE REDUCED! BRICK BEAUTY ON A CORNER LOT WITH AN ATTACHED CARPORT AND A FULL BASEMENT. This remodeled and freshly painted 2-bedroom, 2-bath rancher with newly refinished hardwood floors is move-in ready. In-town convenience with nearby shopping, restaurants and services. A short drive to commuter routes 81, 37 and 50, downtown and Winchester Medical Center. Perfect for those who are downsizing

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  437 Beechcroft Rd, Winchester, VA 22601

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