Winchester County VA Homes for Sale

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  /5

  $263,900

  • 3 Beds
  • 2 Baths
  • 1,682 Sq Ft

  21 E Germain St, Winchester, VA 22601

  Charming 3-Bedroom Home in Historic Winchester, Virginia Discover this beautifully located 3-bedroom, 2-full bath home nestled in the heart of Historic Winchester. This residence boasts an exceptional location, just a short stroll away from the Old Town Mall, allowing you to enjoy local shops and dining. Positioned along the scenic Apple Blossom parade route, this home is perfect for anyone

  

  Corey Morgan

  CENTURY 21 Envision

  (540) 802-5749

  21 E Germain St, Winchester, VA 22601
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  /29

  $295,000

  • 3 Beds
  • 1 Bath
  • 1,325 Sq Ft

  312 Shawnee Ave, Winchester, VA 22601

  Within walking distance to Historic Downtown Winchester! Public record square footage was found to be inaccurate - listing square footage has been adjusted and price adjusted accordingly. This home is convenient to everything happening in Winchester and also a very easy location for commuters. Nestled in the charming Shawnee Heights neighborhood, this delightful cottage-style home offers a

  

  Lori Bales

  Keller Williams Realty

  (540) 209-9771

  312 Shawnee Ave, Winchester, VA 22601
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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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  /36

  $365,000

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft

  127 Shirley St, Winchester, VA 22601

  Comfortable living at this split-foyer home located in the heart of the City of Winchester. On the main level, you’ll find three bedrooms and a full bath. The lower level features a fourth bedroom plus a second full bath — ideal for guests, or a home office. Location is a standout. You’re just minutes from downtown dining, shopping, and community events, and enjoy easy access to schools, parks,

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 802-5087

  127 Shirley St, Winchester, VA 22601
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  /25

  $379,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft

  230 Monteith Dr, Winchester, VA 22601

  OPEN HOUSE: Saturday - Sunday 1pm - 3pm 3 Level Home with Deck! MOVE-IN READY! Explore Winchester’s new luxury townhome community. This three level home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. The main level includes a private finished recreation room and possible 4th bedroom with its own

  DRB Homes Builder

  230 Monteith Dr, Winchester, VA 22601
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  /26

  $369,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft

  222 Monteith Dr, Winchester, VA 22601

  OPEN HOUSE: Saturday - Sunday 1pm - 3pm 3 Level Condo with Box Bay Windows! Explore Winchester’s new luxury townhome community. This three level home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with an extended island that seats four at counter height. The first

  DRB Homes Builder

  222 Monteith Dr, Winchester, VA 22601
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  /26

  $389,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft

  Bedford II Plan at Village at Valor Crossing - Townhomes, Winchester, VA 22601

  OPEN HOUSE: Saturday - Sunday 1pm - 3pm Covered front porch leads into the foyer. Attached 1 car garage or optional flex room or study. Open concept kitchen located next to the country kitchen and living room. Box bay rear window and 10' x 14' Trex deck. Owner’s suite with large walk-in closet, dual vanity, and oversized seated shower in owner’s bath. Fireplace option available in select homes.

  DRB Homes Builder

  0 Tbd Weems Ln Unit 36470375, Winchester, VA 22601
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  /24

  $389,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft

  210 Monteith Dr, Winchester, VA 22601

  OPEN HOUSE: Saturday - Sunday 1pm - 3pm Beautiful open concept living 3 level townhome with Lower Level Walkout! The Bedford II 3 level interior town home with a box bay window with 1 car garage featuring 3 Bedrooms and 3.5 Baths and 1,784 square feet. It is fully finished top to bottom. The front door with the electronic Ring door camera leads directly into the spacious lower-level recreation

  DRB Homes Builder

  210 Monteith Dr, Winchester, VA 22601
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  /30

  $379,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft

  209 Monteith Dr, Winchester, VA 22601

  OPEN HOUSE: Saturday - Sunday 1pm - 3pm 3 Level Condo with Deck! Explore Winchester’s new luxury townhome community. This three level home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. The main level includes a private finished recreation room and possible 4th bedroom with its own full bath and

  DRB Homes Builder

  209 Monteith Dr, Winchester, VA 22601
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  /67

  $399,999

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  707 E Cork St, Winchester, VA 22601

  Don't let this location fool you - Plenty of parking on the side and back of the home and a large turn around space to exit onto Cork St easily! Centrally located colonial with gorgeous hardwood flooring and trim throughout! Step back in time, but enjoy all of the modern amenities with easy access to Jim Barnett Park just down the street, downtown walking mall and commuter roads, and even views

  Misty Weaver Samson Properties

  707 E Cork St, Winchester, VA 22601
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  /35

  $430,000

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  17 E Leicester St, Winchester, VA 22601

  Classic 2100 square foot brick “American Foursquare” house in Winchester’s historic district. This very well maintained 1928 home was designed and built by “ole time” craftsmen who had an appreciation for solid, quality construction. What better way to spend wonderful lazy evenings or morning coffee than on the expansive 23-foot long front porch with a ceiling fan. This 4 bedroom, 2 bath home is

  Roger Lamborne MarketPlace REALTY

  17 E Leicester St, Winchester, VA 22601
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  /47

  $519,900

  • 3 Beds
  • 1.5 Baths
  • 2,177 Sq Ft

  216 Fairmont Ave, Winchester, VA 22601

  Classy colonial on the stately Fairmont Avenue with million dollar homes nearby, walking mall in close proximity with a plethora of boutique shops and eateries. The 2000 square feet is designed for comfort and coziness accented by 9ft ceilings, sunlit formal rooms, a well appointed kitchen, spacious bedrooms, adorable loft on 3rd level for a playroom/den/office, and the best part is entering your

  Dave Spence RE/MAX Roots

  216 Fairmont Ave, Winchester, VA 22601
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  /72

  $699,900

  • 4 Beds
  • 3.5 Baths
  • 3,475 Sq Ft

  132 Amherst St, Winchester, VA 22601

  Price Improvement to make this Yours! Step back in time with this Beautifully preserved VICTORIAN Brick Home Built in 1880, a true piece of Winchester's history. This is a Registered Historic Property that showcases original architectural details, high ceilings, ornate trim, and original wood floors that reflect the artistry of a bygone era. A Well Designed Addition has allowed for generous space

  Jodi Costello ERA Oakcrest Realty, Inc.

  132 Amherst St, Winchester, VA 22601
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  /43

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,580 Sq Ft

  420 Russelcroft Rd, Winchester, VA 22601

  Welcome to 420 Russelcroft Road — the house that practically checks all your boxes *and* puts a smile on your face while doing it. With 1,580 square feet of comfortable living space, this 3-bedroom, 2-bath beauty has all the right vibes. The hardwood floors throughout most of the home give it a touch of class (and make cleaning a breeze), while the carpeted bedrooms give you that perfect excuse

  Brian Yoder Realty ONE Group Old Towne

  420 Russelcroft Rd, Winchester, VA 22601
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  /35

  $479,990 New Construction

  • 4 Beds
  • 3 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 January 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

  D.R. Horton Builder

  1829 Harvest Dr, Winchester, VA 22601
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  /17

  $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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  /35

  $290,000

  • 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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  /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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  /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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  /21

  $384,900

  • 2 Beds
  • 1.5 Baths
  • 1,186 Sq Ft

  711 E Cork St, Winchester, VA 22601

  This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door.

  Marco Novillo Spring Hill Real Estate, LLC.

  711 E Cork St, Winchester, VA 22601
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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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  /21

  $389,880 Open Sat 12PM - 4PM

  • 3 Beds
  • 4 Baths
  • 1,989 Sq Ft

  117 Boone Ct, Winchester, VA 22602

  Immediate Move-in at Rossum Crossing! Winchester's newest and most popular townhome community, conveniently located near shopping and dining options. The St. Paul Townhome features three bedrooms, two and a half baths, and a one-car garage. The main floor boasts an open-concept floor plan, with a spacious family room that flows into a fully equipped kitchen. The kitchen includes an island, a

  Dorelba Estrada New Home Star Virginia, LLC

  117 Boone Ct, Winchester, VA 22602
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  /11

  $409,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,060 Sq Ft

  TBB Monteith Dr Unit DEEP CREEK II, Winchester, VA 22601

  ***OFFERING UP TO $7K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*The only amenity-filled community within Winchester City! Discover modern living in this 3-4-bedroom, 2-3.5-bath home designed for comfort, style, and functionality. The open-concept main level features an

  Brittany Newman DRB Group Realty, LLC

  TBB Monteith Dr Unit DEEP CREEK II, Winchester, VA 22601
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  /115

  $479,999

  • 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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  /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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  /10

  $370,000

  • 4 Beds
  • 3 Baths
  • 1,868 Sq Ft

  126 N Euclid Ave, Winchester, VA 22601

  Discover this charming brick home that offers a perfect blend of classic character and modern convenience. This detached home features 4 spacious bedrooms and 3 full bathrooms, providing ample space for relaxation and privacy. The inviting living area boasts a cozy fireplace, ideal for creating warm memories during chilly evenings and on this level, you'll also have 2 bedrooms and a full bath.

  Marta Bingham Real Broker, LLC

  126 N Euclid Ave, Winchester, VA 22601
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  /16

  $279,900

  • 3 Beds
  • 1.5 Baths
  • 1,332 Sq Ft

  2901 Sorrell Ct, Winchester, VA 22601

  *Investor Opportunity, current tenants have a lease until May of 2027* Welcome to your new home! This beautifully maintained 3 -bedroom, 1.5 bath townhome offers comfort, convenience, and style in a great location. On the main level you will find a spacious kitchen with ample cabinetry and a breakfast area, the living room offers plenty of natural light, off the living room is a convenient half

  Amber Jenkins Century 21 Redwood Realty

  2901 Sorrell Ct, Winchester, VA 22601
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  /2

  $476,500 Coming Soon

  • 3 Beds
  • 3 Baths
  • 2,568 Sq Ft

  407 Jefferson St, Winchester, VA 22601

  COMING SOON! Your PERFECT TURN KEY classic colonial, fully UPDATED, and PHENOMENALLY LOCATED! Stroll to the restaurants in Old Town, enjoy the activities at Handley, or walk to the trails at MSV! NEW, NEW, NEW! New roof, HVAC, privacy fencing, custom paint and built-in cabinetry, plus new stainless steel appliances, including washer/dryer. GET CREATIVE in your FINISHED lower level walk-out!

  Gillian Greenfield Coldwell Banker Premier

  407 Jefferson St, Winchester, VA 22601
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  /13

  $349,999

  • 5 Beds
  • 2 Baths
  • 1,584 Sq Ft

  505 Green St, Winchester, VA 22601

  BACK ON THE MARKET DUE TO BUYER FINANCING AND NON PERFORMANCE. Charming 3-Level Split Home in the Heart of Winchester! This split level home could be your forever home! Surrounded by parks, top-rated schools, and everyday amenities. Quick access to Route 7 and Interstate 81 commuting is breeze! Upstairs, you’ll find three generously sized bedrooms and a full bathroom, offering a peaceful seperate

  Julissa Rodriguez Vaze Realty

  505 Green St, Winchester, VA 22601
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  /143

  $899,000

  • 5 Beds
  • 4.5 Baths
  • 4,438 Sq Ft

  769 Seldon Dr, Winchester, VA 22601

  Welcome to 769 Seldon Drive—an elegant brick-front colonial situated on nearly half an acre in one of Winchester’s most desirable neighborhoods. Offering over 4,500 finished square feet, this spacious 5-bedroom, 4.5-bath home is designed for comfort, flexibility, and multi-generational living. The main level features a generously sized primary suite with a walk-in closet and en-suite bath, along

  Amanda Slate Keller Williams Realty

  769 Seldon Dr, Winchester, VA 22601
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  /32

  $448,950

  • 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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  /10

  $549,900

  • Land
  • 0.09 Acre
  • $6,110,000 per Acre

  1 N Braddock St, Winchester, VA 22601

  Make Offer! Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and

  Gillian Greenfield Coldwell Banker Premier

  1 N Braddock St, Winchester, VA 22601
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  /14

  $1,499,000

  • Land
  • 2 Acres
  • $749,500 per Acre

  1625 Amherst St, Winchester, VA 22601

  Introducing a fantastic development opportunity! This parcel features 2 flat acres of commercial land in a prime location. Located on a major thoroughfare into downtown Winchester and a half mile from Winchester Medical Center, this lot is ideal for your commercial venture. The lot offers excellent road frontage and good topography. Ideal for medical/dental office, office space, restaurant, or

  Dan Whitacre Colony Realty

  1625 Amherst St, Winchester, VA 22601
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  /43

  $564,900

  • 4 Beds
  • 4 Baths
  • 2,489 Sq Ft

  687 Woodland Ave, Winchester, VA 22601

  Experience refined living in this stunning two-level brick residence, designed with an open-concept layout that seamlessly blends sophistication and comfort. The home features 4 spacious bedrooms, each with a private full bathroom.The kitchen boasts granite countertops and elegant finishes, flowing effortlessly into the dining and living areas — perfect for entertaining or relaxing by the gas

  Mauricio Argandona Fairfax Realty Select

  687 Woodland Ave, Winchester, VA 22601
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  /27

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,419 Sq Ft

  309 W Tevis St, Winchester, VA 22601

  Discover this Charming One-Level Rambler Featuring an Attached Two-Car Garage and a Thoughtful Layout Designed for Comfortable Living. Enjoy Spacious Bedrooms, Walk-In Closets, and a Warm Gas Fireplace that Anchors the Inviting Living Area. The Home Offers a Spacious Eat-In Kitchen, Providing Ample Room for Cooking, Dining, and Daily Gatherings. Step Outside to a Screened-In Deck, Perfect for

  Matthew Altizer ANR Realty, LLC

  309 W Tevis St, Winchester, VA 22601
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  /52

  $399,990 New Construction

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

  1814 Blythe Way, Winchester, VA 22601

  1814 Blythe Way is an attractive new 3 level townhome with full brick front in Winchester, VA for January move-in. Our modern Adams floorplan features a 1-car garage, and along with 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, Stone Grey cabinets, and stainless-steel

  D.R. Horton Builder

  1814 Blythe Way, Winchester, VA 22601
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  /56

  $1,899,000

  • Studio
  • 7,190 Sq Ft

  908 Cedar Creek Grade, Winchester, VA 22601

  In town location for this completely remodeled multi unit property. This property contains 4 homes and 2 apartments that have been completely refinished. The main home is currently lived in by the owner and is attached to a indoor swimming pool. The other 3 homes and 2 apartments are leased and are bringing over$10,500 monthly. If you choose rent the main house income would be much higher. .

  Meridee Powars Link Realty Services LLC

  908 Cedar Creek Grade, Winchester, VA 22601
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  /72

  $494,900

  • 5 Beds
  • 3.5 Baths
  • 3,330 Sq Ft

  118 Russelcroft Rd, Winchester, VA 22601

  Tina Jacobin Main Street Realty

  118 Russelcroft Rd, Winchester, VA 22601
• 

  

  /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
• 

  

  /3

  $2,300,000

  • Land
  • 3.51 Acres
  • $655,271 per Acre

  1721 Amherst St, Winchester, VA 22601

  3.51 AC of premier commercial land. Directly across the street from the main hospital campus on one of Winchester's main commercial corridors. Ideal for banks, medical offices, retail or restaurants.

  Marie DiLorenzo Oakcrest Commercial LLC.

  1721 Amherst St, Winchester, VA 22601

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