Winchester, VA Homes for Sale under $500,000

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  $469,900 Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,698 Sq Ft

  312 W Cecil St, Winchester, VA 22601

  Coming Soon! Don’t miss your chance to live on sought-after W. Cecil in this charming, beautifully maintained historic home. Light-filled and inviting, this home welcomes you with a classic covered front porch and warm hardwood floors that set the tone for the character throughout. The cozy living room features a recently converted gas fireplace, lovely built-ins, and crown molding. This space

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 413-0699

  312 W Cecil St, Winchester, VA 22601
• Explore Winchester

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  /50

  $425,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  220 Chestnut Grove Rd, Winchester, VA 22603

  Experience the best of country living with this charming 2-Bedroom, 1-Bath Rancher nestled on 15 unrestricted acres in beautiful Frederick County, VA. Perfect as a full-time residence, weekend retreat, or potential farm, this property offers the peace and privacy of rural life while still being within easy reach of town conveniences.Step inside to find a cozy and move-in ready Home featuring

  

  Laura King

  MarketPlace REALTY

  (540) 351-9580

  220 Chestnut Grove Rd, Winchester, VA 22603
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  /88

  $435,000

  • Studio
  • 2,152 Sq Ft

  26 A Jackson Ave, Winchester, VA 22601

  Rare Opportunity: Turnkey Duplex in Winchester – Vacant, Updated, and Ready for Your Next Move! A rare and an exceptional opportunity to own a two-unit duplex in Winchester City— vacant and ready for your plans. Whether you’re an investor seeking strong cash flow or an owner-occupant looking to live in one unit and rent the other, this property offers flexibility, income potential, and low

  

  Melanie Lucero

  Real Broker, LLC

  (540) 386-1285

  26 A Jackson Ave, Winchester, VA 22601
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  /24

  $459,990 New Construction

  • 2 - 3 Beds
  • 1 Bath
  • 1,564+ Sq Ft

  Hemingway Plan at Hiatt Pointe at Snowden Bridge - 55+ Garden Homes Collection, Winchester, VA 22603

  Welcome to your ideal one-level villa- the Hemingway! This thoughtfully designed home centers around a spacious kitchen, perfect for both daily life and entertaining guests. The main level offers two generous bedrooms, including a primary suite featuring a large walk-in closet and a private en suite bathroom for ultimate comfort. Convenience is key with a laundry room located just off the 2-car

  Brookfield Residential Builder

  105 Wagtail Ln Unit 36578850, Winchester, VA 22603
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  /24

  $454,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,665 Sq Ft

  CABRAL Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

  The Cabral, a 1,657 square foot open concept two-story home, offers three bedrooms, two and a half bathrooms, a loft and a two-car garage. As you make your way from the front porch into the foyer you will find a convenient first-floor powder room and coat closet. Past the foyer is the large, open concept living room that flows nicely into the eat-in kitchen that overlooks the casual dining area

  D.R. Horton Builder

  137 Seminole Dr Unit 36203778, Winchester, VA 22602
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  /46

  $498,119 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,181 Sq Ft

  108 Keystone, Winchester, VA 22603

  Embrace the Vera 30-F2 – Homesite 1094 at Hiatt Pointe—a two-car, front-load garage villa with three bedrooms, two full bathrooms, and one half bathroom is ready for you to move in IMMEDIATELY. Built for the way you live, this factory-framed floorplan makes room for moments big and small. Be welcomed by 9’ ceilings on both levels, oak main stairs, and expertly selected finishes that make this

  Shannon L Bray Pearson Smith Realty, LLC

  108 Keystone, Winchester, VA 22603
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  /44

  $496,129 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,195 Sq Ft

  117 Wagtail Ln, Winchester, VA 22603

  Embrace the Vera 30-F2 – Homesite 1031 at Hiatt Pointe—a two-car, front-load garage VILLA with three bedrooms, two full bathrooms, and one half bathroom will be ready IMMEDIATELY. Built for the way you live, this factory-framed floorplan makes room for moments big and small. Be welcomed by 9’ ceilings on both levels, oak main stairs, and expertly selected finishes that make this villa feel

  Shannon L Bray Pearson Smith Realty, LLC

  117 Wagtail Ln, Winchester, VA 22603
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  /44

  $492,669 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,187 Sq Ft

  114 Keystone, Winchester, VA 22603

  Embrace the Vera 30-F2 – Homesite 1096 at Hiatt Pointe—a two-car, front-load garage VILLA HOME with three bedrooms, two full bathrooms, and one half bathroom will be ready IMMEDIATELY. Built for the way you live, this factory-framed floorplan makes room for moments big and small. Be welcomed by 9’ ceilings on both levels, oak main stairs, and expertly selected finishes that make this villa feel

  Shannon L Bray Pearson Smith Realty, LLC

  114 Keystone, Winchester, VA 22603
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  /49

  $481,290

  • 3 Beds
  • 2.5 Baths
  • 2,181 Sq Ft

  0 Magpie Ln Unit VAFV2037506, Winchester, VA 22603

  Explore new 55+ VILLA HOMES by Van Metre Homes at Hiatt Pointe (55+) in Winchester, VA. that will be ready for you to move in 2026. Embrace the Vera 30-F2 at Hiatt Pointe—a two-car, front-load garage villa with three bedrooms, two full bathrooms, and one half bathroom. Built for the way you live, this floorplan makes room for moments big and small with its natural flow and central kitchen. The

  Shannon L Bray Pearson Smith Realty, LLC

  0 Magpie Ln Unit VAFV2037506, Winchester, VA 22603
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  $449,900

  • 3 Beds
  • 2.5 Baths
  • 2,012 Sq Ft

  4403 Back Mountain Rd, Winchester, VA 22602

  Nestled on two private wooded acres, 4403 Back Mountain Road in Winchester, VA offers a peaceful country retreat with no HOA or restrictions. Built in 2001, this traditional Colonial-style home features approximately 2,012 square feet of comfortable finished living space, including three bedrooms and two and a half baths . The walk-out basement provides excellent storage and potential for future

  RoxAnn Grimes RE/MAX Roots

  4403 Back Mountain Rd, Winchester, VA 22602
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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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  /20

  $455,000

  • 6 Beds
  • 3 Baths
  • 1,552 Sq Ft

  2250 Roosevelt Blvd, Winchester, VA 22601

  Sellers are highly motivated and ready to make a deal!Beautifully Renovated Single-Family Home with a little Pool, Workshop, and Detached GaragesWelcome to this stunning fully renovated 4-bedroom, 3-bathroom single-family home that perfectly blends comfort, style, and functionality. Step inside to find an open-concept layout filled with natural light, ideal for both everyday living and

  Silvana Rojas Spring Hill Real Estate, LLC.

  2250 Roosevelt Blvd, Winchester, VA 22601
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  /55

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft

  113 Williamson Rd, Winchester, VA 22602

  Charming All-Brick Ranch just minutes from in Prime Winchester Location. Beautifully maintained all-brick ranch just minutes from Jim Barnett Park, Winchester Country Club, shopping, and everyday amenities. This well built home blends timeless craftmanship with modern comfort and offers the ease of low maintenance, energy efficient brick construction. Step inside to discover a spacious main level

  Avis Drummond Long & Foster Real Estate, Inc.

  113 Williamson Rd, Winchester, VA 22602
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  /42

  $449,900

  • 4 Beds
  • 1.5 Baths
  • 1,932 Sq Ft

  420 W Cork St, Winchester, VA 22601

  Discover the perfect blend of historic charm and modern convenience at 420 W Cork Street. This captivating four-level brick home offers 4 bedrooms and 1.5 baths, boasting beautiful hardwood floors, gorgeous trim and plenty of space for you and yours. The main level offers a spacious living room, dining room and kitchen. Upstairs you will find 4 sizable bedrooms and a full bath. The top level is a

  Dan Whitacre Colony Realty

  420 W Cork St, Winchester, VA 22601
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  /47

  $447,900

  • 3 Beds
  • 3.5 Baths
  • 2,686 Sq Ft

  106 Foxglove Dr, Winchester, VA 22602

  This home is back on the market through no fault of the seller. This spacious 3BD/3.5BA Colonial home combines modern upgrades with a versatile layout. The upper level includes three spacious bedrooms and a laundry room. The primary suite is huge and includes a large bump out area that offers a great space to relax, whether that's reading in your favorite chair or a morning yoga stretch.

  Matt Baer MarketPlace REALTY

  106 Foxglove Dr, Winchester, VA 22602
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  /47

  $467,000

  • 4 Beds
  • 3 Baths
  • 2,654 Sq Ft

  219 Milam Dr, Winchester, VA 22602

  Welcome to 219 Milam Drive, a spacious and updated all-brick rancher tucked in a quiet neighborhood just minutes from downtown Winchester, Route 7, and I-81. This four-bedroom, three-bath home offers over 2,700 square feet of finished living space, including a partially finished basement and additional storage or hobby rooms to suit your needs. Inside, you’ll find warm hardwood flooring, modern

  Kira Grubb Realty ONE Group Old Towne

  219 Milam Dr, Winchester, VA 22602
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  /32

  $474,500

  • 4 Beds
  • 4 Baths
  • 1,627 Sq Ft

  201 Parkway St, Winchester, VA 22601

  Freshly Renovated Charmer in Winchester! Welcome to 201 Parkway Street, a freshly updated home in the heart of Winchester! Previously tenant-occupied, this property has been thoughtfully refreshed and is ready for new owners. Recent Updates Include: Fresh interior paint throughout Renovated kitchen and bath Updated fixtures and finishes Clean, move-in ready condition This home offers the perfect

  Cherish Green Coldwell Banker Elite

  201 Parkway St, Winchester, VA 22601
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  /28

  $475,000

  • 6 Beds
  • 3 Baths
  • 2,736 Sq Ft

  386 Round Hill Rd, Winchester, VA 22602

  *** ATTENTION INVESTORS - OFFERED AT A NEW PRICE!! *** You will want to check out this fantastic opportunity - with a history of POSITIVE CASH FLOW these two ADJACENT PROPERTIES on a combined total of 1.91-acres in Winchester (just minutes from Valley Health Campus, shopping, restaurants and Rt. 37) may be what you are looking for! *** These two parcels are to be sold TOGETHER; they are not

  Bridget Aikens Colony Realty

  386 Round Hill Rd, Winchester, VA 22602
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  /23

  $449,900

  • 3 Beds
  • 2.5 Baths
  • 2,250 Sq Ft

  104 Primrose Place, Winchester, VA 22602

  Moe Gahche Long & Foster Real Estate, Inc.

  104 Primrose Place, Winchester, VA 22602
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  /27

  $499,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,168 Sq Ft

  109 Trellis View Ln, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Freeport floorplan is a thoughtfully designed villa blending style and functionality in a single-level open layout and finished loft. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen,

  D.R. Horton Builder

  109 Trellis View Ln, Winchester, VA 22602
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  $479,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,920 Sq Ft

  1829 Harvest Dr, Winchester, VA 22601

  1829 Harvest Drive is an attractive end unit new 3 level townhome with full brick front in Winchester, VA for December move-in. Our modern Adams II floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, white cabinets, and stainless-steel

  Brooks Sears D R Horton Realty of Virginia LLC

  1829 Harvest Dr, Winchester, VA 22601
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  /2

  $450,000 Coming Soon

  • 3 Beds
  • 3.5 Baths
  • 2,486 Sq Ft

  115 Alpine Meadow Rd, Winchester, VA 22602

  Ismael Carino MarketPlace REALTY

  115 Alpine Meadow Rd, Winchester, VA 22602
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  /16

  $450,000

  • Land
  • 77 Acres
  • $5,844 per Acre

  92 Bobcat Trail, Winchester, VA 22602

  Calling all hunters or just someone who wants seclusion! This property has amazing views and already has a structure perfect to finish your way! Perfect for getting away from it all or long hunting trips. No septic or power to structure yet. Gate to enter property. Property has 2 pink flags at the beginning of property and runs all the way to the power lines.

  Daryl Stout RE/MAX Real Estate Connections

  92 Bobcat Trail, Winchester, VA 22602
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  /51

  $419,900

  • 4 Beds
  • 2 Baths
  • 1,920 Sq Ft

  133 Cardinal Ln, Winchester, VA 22602

  Welcome to this well maintained and fully remodeled split foyer, tucked away in a private cul-de-sac setting. Located just minutes from route 7 and I-81, commuting will be a breeze. Brand new LVP flooring flow seamlessly across both levels, as does the neutral colors throughout. The spacious eat-in kitchen is the heart of the home-with white cabinetry, granite countertops, tile backsplash and

  Heloisa Amar Samson Properties

  133 Cardinal Ln, Winchester, VA 22602
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  $400,000

  • 4 Beds
  • 2.5 Baths
  • 2,636 Sq Ft

  100 Winns Cir, Winchester, VA 22602

  Welcome home to Winns Circle! This lovely home is well maintained and ideally located on a corner lot near all that Winchester has to offer. With an open first floor floorplan and lots of room for entertaining, from the large eat in kitchen, to the spacious living room and walkout decking, this home is has so many possibilities! Upstairs hosts four large rooms, ready for hobby spaces, bedrooms,

  Nicole Lewis Coldwell Banker Premier

  100 Winns Cir, Winchester, VA 22602
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  /42

  $419,000

  • 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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  /50

  $414,999

  • 3 Beds
  • 2 Baths
  • 2,131 Sq Ft

  204 Ridge Rd, Winchester, VA 22602

  Well maintained brick Rancher(upgraded vinyl clad tilt windows,newer architectural roof) on a full basement on the east side of Winchester featuring over 2100 sqft of finished living space that offers true hardwood flooring on the main level with 3 bedrooms and 1 full bath. Spacious living room that features a gas log fireplace that has a woodstove insert included. Basement is 90% finished with a

  James Amick RE/MAX Roots

  204 Ridge Rd, Winchester, VA 22602
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  /19

  $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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  $499,999

  • 5 Beds
  • 3 Baths
  • 2,080 Sq Ft

  419 Summit Ave, Winchester, VA 22601

  Welcome Home!This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and granite countertops in the kitchen, this home combines style and functionality. A new roof adds peace of mind, and the fully finished lower level provides additional living space for relaxation or entertainment.With 5

  Waqas Abbasi Lifestyle Realty, LLC.

  419 Summit Ave, Winchester, VA 22601
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  /36

  $410,000

  • 4 Beds
  • 3.5 Baths
  • 2,261 Sq Ft

  125 Cheshire Ct, Winchester, VA 22602

  Beautiful and well-maintained 4 bedroom, 3.5 bath townhouse at the end of a quiet cul-de-sac on the east side of Winchester. Conveniently located to Rt 7 and I-81 and historic downtown Winchester. The 3-level townhouse backs to a wooded tree area and has a fenced rear yard. New luxury vinyl floor installed in majority of the home. As you enter, you will be welcomed into a large foyer with

  Eric Kronenwetter RE/MAX Roots

  125 Cheshire Ct, Winchester, VA 22602
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  /43

  $490,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 4 Baths
  • 3,359 Sq Ft

  227 Miller St, Winchester, VA 22601

  Welcome to 227 Miller Street — a home that instantly feels inviting. The front porch sets the tone, offering a perfect spot for quiet mornings in the heart of downtown Winchester. Inside, the main level has an easy flow: a bright living room, a dining space ready for gatherings, and a sun-filled enclosed sunroom that naturally becomes a favorite place to slow down. The kitchen has all new

  Leah Marabella Realty ONE Group Old Towne

  227 Miller St, Winchester, VA 22601
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  /43

  $459,000

  • 3 Beds
  • 2 Baths
  • 2,648 Sq Ft

  1332 Ramseur Ln, Winchester, VA 22601

  Welcome home to a rare find in the Mews of Meadow Branch - this exceptional all-brick exterior condo offering 3 bedrooms and 2 full baths. Rich hardwood floors flow throughout the home. The primary bedroom includes a cozy fireplace perfect for relaxing evenings. Updated appliances, such as washer, dryer, refrigerator, stove and microwave. Enjoy the ease of your own private elevator within the

  James King RE/MAX Roots

  1332 Ramseur Ln, Winchester, VA 22601
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  $499,000

  • 4 Beds
  • 2.5 Baths
  • 1,959 Sq Ft

  129 Old Wagon Rd, Winchester, VA 22602

  *Sellers are offering $850 towards a home warranty of the buyer's choice* "Outstanding On Old Wagon" This 4 bedroom, 2 1/2 bath colonial style home sits in a cul-de-sac in the highly desirable Pioneer Heights Neighborhood. This home has had a ton of upgrades over the years! Gorgeous, updated custom kitchen with Frigidaire Gallery Appliances, custom built cabinets with pull out shelves, extra

  Matt Kilmer Samson Properties

  129 Old Wagon Rd, Winchester, VA 22602
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  /14

  $441,700

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

  421 Superior Ave, Winchester, VA 22601

  Renovated and move in ready! Let's start with the new mailbox, new 16' wide asphalt driveway, new 8'x13' concrete patio for you to enjoy watching the sun sets overlooking the large back yard., The carport even has bolts in ceiling for you to install a swing. Then inside, new heat pump and central a/c system, new appliances with fingerprint resistant stainless-steel exterior, stainless steel liner

  Leo Smith CENTURY 21 New Millennium

  421 Superior Ave, Winchester, VA 22601
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  /17

  $435,000

  • 5 Beds
  • 4 Baths
  • 2,014 Sq Ft

  122 Cherry Hill Cir, Winchester, VA 22602

  Nestled in the charming Green Acres subdivision, this delightful split-level home offers a perfect blend of comfort and functionality. With five spacious bedrooms and four full bathrooms, there's ample room for everyone to unwind and thrive. The heart of the home features a cozy fireplace, inviting you to gather with loved ones during chilly evenings. The fully finished basement, complete with

  Jen Moore ERA Oakcrest Realty, Inc.

  122 Cherry Hill Cir, Winchester, VA 22602
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  /20

  $449,900

  • Studio
  • 2,376 Sq Ft

  510 N Loudoun St, Winchester, VA 22601

  All brick 3 unit complex with off street parking and near Old Town Mall..2nd floor has 2BD/1BA with unfinished attic, main floor is 1BR/1BA (Both have rear balcony) and basement unit has access to storage area and includes1BD/1BA. All units have washer/dryer (Basement unit washer/dryer belongs to tenant). Owner/Agent and home inspection report available upon request.

  Dave Spence RE/MAX Roots

  510 N Loudoun St, Winchester, VA 22601
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  /49

  $489,970

  • 5 Beds
  • 3 Baths
  • 3,116 Sq Ft

  110 Carter Place, Winchester, VA 22602

  Contract fell through! Interest rates have gone down! Extensive Renovations: The home has been fully renovated in 2025, including updates to kitchen, bathrooms, flooring, and fresh paint throughout. Designed to accommodate two families comfortably, featuring large rooms that are flooded with natural light like the entire house. The lower level is equipped with wheelchair-accessible features,

  Rodrigo Cruz Long & Foster Real Estate, Inc.

  110 Carter Place, Winchester, VA 22602
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  /47

  $435,000

  • 3 Beds
  • 1.5 Baths
  • 1,952 Sq Ft

  164 Bethel Grange Rd, Winchester, VA 22603

  Beautiful brick ranch in a lovely, country rural setting with mountain views and only minutes to schools and town amenities. Sellers just installed new heat pump air conditioning and heat. 3 bedrooms, 1 1/2 baths with a shower stall in mud room downstairs. Country kitchen with adjoining carport. Large living room front window with nice view of Round Hill. Extra closets. 4 foot hallway with

  Cathy Durbin Crum Realty, Inc.

  164 Bethel Grange Rd, Winchester, VA 22603
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  /7

  $499,000

  • Land
  • 17.98 Acres
  • $27,753 per Acre

  Lot 13 Tavistock Dr, Winchester, VA 22602

  Beautiful 17.98 acre Lot, approved for 3 bedroom perk, Tavistock Estates, one of the last lots remaining! A gorgeous 7 minute drive from town through farmland and full of mountain views. Excellent neighborhood, road access is great, level lot among 'horse country' estates! Build your dream mini equestrian farm or just enjoy peace, quiet, and serenity with the genius of a quick commute into town!

  Gillian Greenfield Coldwell Banker Premier

  Lot 13 Tavistock Dr, Winchester, VA 22602
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  /2

  $500,000

  • Studio
  • 1,175 Sq Ft

  513 and 525 Monticello St, Winchester, VA 22601

  For Sale – 1.89 + Acres Redevelopment Site located just off Valley Avenue in southern Winchester. Property consists of 2 parcels and includes a single family detached rental and one unimproved lot. Lot is zoned MR and Improved parcel is zoned B-2. Property is ideally suited for multi-family development. All properties are leased. Call listing broker for additional information. Do not disturb

  Brett Haynes Oakcrest Commercial LLC.

  513 and 525 Monticello St, Winchester, VA 22601

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