Winchester County VA Homes for Sale

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  $295,000 Coming Soon

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  704 Watson Ave, Winchester, VA 22601

  Beautifully Maintained Bungalow in a Prime Location! This very well-kept home offers 2 bedrooms and 1 full bath on the main level, showcasing pride of ownership throughout. Ideally located just blocks from shopping, coffee shops, and all the conveniences the city has to offer, this property combines comfort with unbeatable accessibility. Enjoy a spacious eat-in kitchen with plenty of room for a

  

  Carlos Soares

  Samson Properties

  (540) 530-4023

  704 Watson Ave, Winchester, VA 22601
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  /2

  $349,900 Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,890 Sq Ft

  113 Christopher Dr, Winchester, VA 22601

  Meticulously maintained 3 bedroom, 1.5 bath home in a convenient in-town Winchester location! This home shows beautifully and features hardwood floors that add warmth and character throughout the main living areas. Spacious bedrooms and updates made over the years make this home functional and livable, while still providing an opportunity to personalize as desired. The partially finished basement

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 318-0527

  113 Christopher Dr, Winchester, VA 22601
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  /18

  $270,000

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

  2640 Limestone Ct, Winchester, VA 22601

  Discover this charming Colonial-style townhouse nestled in the desirable Limestone Court community. Built in 1994, this end-unit home offers a perfect blend of comfort and convenience. With 2 spacious bedrooms and 1.5 bathrooms, it's ideal for those seeking a cozy yet functional living space. The brick exterior exudes timeless appeal, while the efficient layout maximizes every square foot. Enjoy

  

  Ned Stock

  Berkshire Hathaway HomeServices PenFed Realty

  (540) 329-1991

  2640 Limestone Ct, Winchester, VA 22601
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  $1,300,000

  • Land
  • 64.91 Acres
  • $20,028 per Acre

  Lot 7 Cedar Creek Grade, Winchester, VA

  Rare opportunity to own 64+ scenic acres on the desirable west side of Winchester, VA. This preservation parcel offers one building right and features a beautiful mix of open land and partial woodland, providing both usability and privacy. Formerly an apple orchard, the property is well suited for a small farm, specialty crops, or vineyard, with potential for additional uses with an approved

  

  Lori Bales

  Keller Williams Realty

  (540) 974-1542

  Lot 7 Cedar Creek Grade, Winchester, VA
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  /65

  $389,990

  • 4 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  317 Gray Ave, Winchester, VA 22601

  Welcome to 317 Gray Ave in Winchester, Virginia. This charming Colonial blends historic character with extensive modern updates, creating the perfect balance of vintage appeal and contemporary comfort. The home features 4 bedrooms, 2 full bathrooms, and 1 half bathroom, along with a recently finished attic that offers flexible additional living space. The primary suite includes a beautifully

  

  Matthew Abregu

  Keller Williams Realty

  (540) 701-3590

  317 Gray Ave, Winchester, VA 22601
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  $250,000 Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  514 Cather Ave, Winchester, VA 22601

  Welcome to this beautifully maintained home where classic charm meets modern versatility! Built in 1948, this property offers warmth, character, and flexible living spaces designed to fit today’s lifestyle. Step inside to a spacious main level featuring a bright and inviting family room, a dedicated dining area, and an eat-in kitchen—perfect for everyday living and entertaining. This home offers

  

  Paula Keiper

  EXP Realty, LLC

  (540) 452-9510

  514 Cather Ave, Winchester, VA 22601
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  /2

  $175,000

  • Land
  • 0.37 Acre
  • $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

  (540) 709-9357

  719 Kennedy Dr, Winchester, VA 22601
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  /2

  $250,000

  • 2 Beds
  • 1.5 Baths
  • 1,064 Sq Ft

  523 Monticello St, Winchester, VA 22601

  Sold "As-IS" Nice investment or starter property. Needs a little updating. Hardwoods throughout upstairs and living room downstairs. This price includes 525 Monticello lot. Tax ID #330-02-19. If any questions call listing agent. Agent related to seller.

  

  Ned Stock

  Berkshire Hathaway HomeServices PenFed Realty

  (540) 305-3611

  523 Monticello St, Winchester, VA 22601
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  /22

  $949,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,546 Sq Ft

  0 Oak Ridge Ln Unit VAFV2039728, Winchester, VA 22602

  TO BE BUILT: Fauver and Browning Homes proudly presents The Tremont House—a masterfully designed modern residence that blurs the line between architecture and nature. Thoughtfully crafted to harmonize with its surroundings, this home offers a calm, refined living experience. Tucked at the end of a private cul-de-sac in desirable Fairway Estates, overlooking Winchester Country Club, the design

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 698-4119

  0 Oak Ridge Ln Unit VAFV2039728, Winchester, VA 22602
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  /47

  $289,900

  • 4 Beds
  • 2.5 Baths
  • 1,530 Sq Ft

  2963 Sorrell Ct, Winchester, VA 22601

  Location, location, location! Well-maintained 3-level townhome ideally situated for commuters with convenient access to Route 7 and I-81, and close proximity to shopping, dining, and schools. Ample parking available in both the front and rear of the home.This home features 4 bedrooms, 2 full baths, and 1 half bath with a convenient main-level entry. The kitchen was remodeled in 2020 and

  Renzo Falla RE/MAX Real Estate Connections

  2963 Sorrell Ct, 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

  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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  /31

  $369,990 New Construction

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

  213 Monteith Dr, Winchester, VA 22601

  MOVE-IN READY! 3 Level Condo with Deck and Gourmet Kitchen! Explore Winchester’s new luxury townhome community. This three level interior row 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

  213 Monteith Dr, Winchester, VA 22601
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  /37

  $430,000

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

  17 E Leicester St, Winchester, VA 22601

  LOWER INTEREST RATE FOR YOU.....Sellers are offering you 2 percent of sales price so you can buy down your interest rate with an initial 2/1 interest rate buydown OR use the 2% seller concession for your closing costs on this classic 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

  Roger Lamborne MarketPlace REALTY

  17 E Leicester St, Winchester, VA 22601
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  $389,990 New Construction

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

  221 Monteith Dr, Winchester, VA 22601

  END OF ROW Luxury 3 level/3-bedroom townhome with 1 car garage located in the heart of Winchester! MOVE-IN READY! Explore Winchester’s new luxury townhome community. This three level end unit 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

  DRB Homes Builder

  221 Monteith Dr, Winchester, VA 22601
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  $439,000

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  743 Berryville Ave, Winchester, VA 22601

  Welcome to 743 Berryville Ave in the heart of Downtown Winchester! This unique and versatile property offers exceptional space and flexibility with two fully equipped living areas on one lot.The main house features 4 bedrooms, 2 full bathrooms, 2 kitchens, and 2 laundry areas—ideal for multi-generational living or added convenience. Enjoy a spacious layout with plenty of room for everyone to

  Sineenat Sirimas Pearson Smith Realty, LLC

  743 Berryville Ave, Winchester, VA 22601
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  $585,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,909 Sq Ft

  328 Sheridan Ave, Winchester, VA 22601

  Timeless charm meets thoughtful updates in this beautifully maintained all-brick 1958 home, offering effortless one-level living with a warm retro vibe. Freshly painted throughout and enhanced with new quartz countertops, classic subway tile backsplash, updated sink and faucet, and stylish new lighting, this home blends character with modern comfort. The main level is inviting and functional,

  Mary Casselano Dream Real Estate

  328 Sheridan Ave, Winchester, VA 22601
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  /63

  $550,000

  • 3 Beds
  • 2 Baths
  • 1,974 Sq Ft

  832 Winder Ct, Winchester, VA 22601

  All-brick rancher located in the sought-after Early’s Green at Meadow Branch community, offering 1,974 finished square feet with 9-foot ceilings and true one-level living. The open floor plan provides excellent flow and is ideal for both everyday living and entertaining. Recent interior updates include new hardwood flooring in the main living room, and new carpet in all bedrooms. Tile flooring

  Barton Chasler Realty ONE Group Old Towne

  832 Winder Ct, Winchester, VA 22601
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  $424,500 Open Sun 2PM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 1,805 Sq Ft

  21 W Pall Mall St, Winchester, VA 22601

  Timeless soul with modern spirit. Step into a piece of Winchester history, reimagined for the way you live today. From the iconic front porch—perfect for your morning coffee or evening wind-down—to the private, fenced-in backyard, this home is designed for seamless indoor-outdoor living. Renovated top to bottom with classic features such as crown moulding, thick wood banisters, and columns

  Allyson Lenz Compass

  21 W Pall Mall St, Winchester, VA 22601
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  /46

  $449,000

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

  25 W Southwerk St, Winchester, VA 22601

  **OPEN HOUSE THIS SUNDAY, MARCH 29th, FROM 11-1pm!!**Welcome to this beautifully updated gem in the heart of Winchester! From the moment you arrive, the expansive front porch invites you to sit back and enjoy the charm of one of the city's most sought-after locations. Situated just moments from Handley High School, vibrant downtown shops, local restaurants, and scenic parks, this home offers

  Dan Whitacre Colony Realty

  25 W Southwerk St, Winchester, VA 22601
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  /55

  $585,000

  • 3 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  308 Ridge Ave, Winchester, VA 22601

  Charming all-brick ranch offering comfortable one-level living in a highly convenient location! This well-maintained home features 3 bedrooms and 2 baths on the main level, along with a spacious living room highlighted by a cozy fireplace. A formal dining room provides the perfect space for entertaining, while the kitchen offers ample workspace and connects conveniently to the main-level laundry

  John Scully Colony Realty

  308 Ridge Ave, Winchester, VA 22601
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  /28

  $419,000

  • 4 Beds
  • 2 Baths
  • 1,432 Sq Ft

  115 E Monmouth St, Winchester, VA 22601

  Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

  Mafe Zambrano Inmobiliaria De Las Casas LLC

  115 E Monmouth St, Winchester, VA 22601
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  /45

  $465,000

  • 3 Beds
  • 2.5 Baths
  • 2,293 Sq Ft

  3137 Eton Place, Winchester, VA 22601

  Welcome to The Lofts at Creekside! Better than new and absolutely breathtaking, this four-level interior townhome delivers style, space, and an unbeatable lifestyle—all within walking distance to top-rated restaurants, shopping, and the historic Kernstown Battlefield. Offering 3 bedrooms and 2.5 baths, the home features a chic upper-level loft that opens to a stunning private terrace, perfect for

  Laura White ERA Oakcrest Realty, Inc.

  3137 Eton Place, Winchester, VA 22601
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  $399,000

  • 3 Beds
  • 2.5 Baths
  • 2,338 Sq Ft

  3138 Eton Place, Winchester, VA 22601

  Beautiful, just like brand new, 3 bedroom 2.5 bath end unit townhome located in The Lofts at Creekside! Walking distance to local restaurants and shopping here in Creekside. Home features large kitchen island, stainless steel appliances, and luxury vinyl plank flooring, private balcony, surrounded by open floor plan which provides for great entertainment. Nice upgrades all throughout the house!

  Christopher Hild Realty FC, LLC

  3138 Eton Place, Winchester, VA 22601
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  $379,990 New Construction

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

  218 Monteith Dr, Winchester, VA 22601

  End of Row Townhome With All Three Finished Levels! This three level end of row townhome 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 level includes a private finished recreation room and

  DRB Homes Builder

  218 Monteith Dr, Winchester, VA 22601
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  $459,000

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

  2250 Roosevelt Blvd, Winchester, VA 22601

  Charming Cape Cod nestled in a quiet residential neighborhood, just minutes from Route 11 and I-81 for easy commuting. This light-filled home welcomes you with a bright living room featuring a stunning stone fireplace as its centerpiece. The cabinet-packed kitchen is the heart of the home and offers granite countertops and a bar-height peninsula that opens seamlessly to the living room . The main

  Heloisa Amar Samson Properties

  2250 Roosevelt Blvd, Winchester, VA 22601
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  /20

  $374,990 New Construction

  • 3 Beds
  • 4 Baths
  • 1,910 Sq Ft

  105 Boone Ct, Winchester, VA 22602

  Move in ready at Rossum Crossing townhome community, conveniently located near shopping and dining options. The St. Paul Townhome features three bedrooms, two full and two 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 pantry closet, and a breakfast nook.

  Dorelba Estrada New Home Star Virginia, LLC

  105 Boone Ct, Winchester, VA 22602
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  /63

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,999 Sq Ft

  520 N Braddock St, Winchester, VA 22601

  Welcome to this charming home in the heart of Winchester offering character, natural light, and a highly walkable location.This home features 3 bedrooms and 2 full bathrooms, with all bedrooms located on the upper level. At the top of the stairs you’ll find a spacious primary bedroom filled with natural light, creating a bright and inviting retreat. Large windows throughout the home allow

  Angela Duncan MarketPlace REALTY

  520 N Braddock St, Winchester, VA 22601
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  /55

  $474,900

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

  620 Crystal Ct, Winchester, VA 22601

  Rare Cul-de-Sac Gem in the Heart of Winchester! Now priced nearly $20,000 under appraisal value!! Discover the perfect blend of tranquility and city convenience at 620 Crystal Court. Situated in a sought-after, quiet cul-de-sac right in the center of Winchester, this stunning 4-bedroom, 2.5-bathroom residence has been thoughtfully updated and is ready for you to call home. Main Level Elegance &

  VAIBHAV AGARWAL Realty FC, LLC

  620 Crystal Ct, Winchester, VA 22601
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  /25

  $389,990 New Construction

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

  201 Monteith Dr, Winchester, VA 22601

  End Of Row Townhome With 1 Car Garage & Rear Deck! MOVE-IN READY! Explore Winchester’s new luxury townhome community. This three level end of row 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, range

  DRB Homes Builder

  201 Monteith Dr, Winchester, VA 22601
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  /17

  $389,990 New Construction

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

  TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601

  ***OFFERING UP TO $12K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*Featuring Bedford II in Valor Crossing! Open concept kitchen located next to the country kitchen and living room. Optional features include box bay rear window and 10' x 14' deck. Primary suite with large

  Brittany Newman DRB Group Realty, LLC

  TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601
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  $429,000

  • 3 Beds
  • 2.5 Baths
  • 1,528 Sq Ft

  209 Wood Ave, Winchester, VA 22601

  Welcome to this beautifully-updated brick rancher, a masterclass in blending timeless character with high-end, modern sophistication. From the moment you arrive, the covered front porch and classic silhouette command attention, offering undeniable curb appeal in one of Winchester’s most sought-after locations. Step inside to find a main level bathed in natural light, showcasing gleaming hardwood

  Dan Whitacre Colony Realty

  209 Wood Ave, Winchester, VA 22601
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  /21

  $389,990 New Construction

  • 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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  /12

  $80,000

  • Land
  • 0.13 Acre
  • $615,385 per Acre

  520 Highland Ave, Winchester, VA 22601

  Empty lot ready to build a home one. The lot is fully fenced with front and rear gates. The front of the lot meets the sidewalks and road of Highland Ave. The rear of the lot meets a gravel alley way that could give access to off street parking on this lot. Homes in the city are in demand, so don't miss this opportunity. Zoned HR-1Can only be used for single family dwellingsFront setback:

  Michael Sprague Samson Properties

  520 Highland Ave, Winchester, VA 22601
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  /11

  $80,000

  • Land
  • 0.08 Acre
  • $1,000,000 per Acre

  24 N Pleasant Valley Rd, Winchester, VA 22601

  Ready for building! Clear open lot that is ready for a home to be built. Winchester City is the fastest growing city in the state and homes are in high demand. Don't miss your opportunity. Property has road front access as well as a gravel alley in the rear that could be used for access to off street parking.Zoned MR - medium density residential districtCan only be used for single family

  Michael Sprague Samson Properties

  24 N Pleasant Valley Rd, Winchester, VA 22601
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  /2

  $339,000 Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,699 Sq Ft

  2956 Grace St, Winchester, VA 22601

  Welcome to 2956 Grace Street — a 3-bedroom, 1-bath ranch-style home offering comfortable single-level living in Winchester, where a simple, functional layout and everyday ease come together. Inside, the home opens to a light-filled living area with hardwood floors that add warmth and character, creating a comfortable place to gather or unwind at the end of the day. The kitchen offers workspace

  Carolyn Young Samson Properties

  2956 Grace St, Winchester, VA 22601
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  /67

  $375,000

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

  707 E Cork St, Winchester, VA 22601

  Make an offer! 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,

  Misty Weaver Samson Properties

  707 E Cork 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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  /97

  $1,200,000

  • 6 Beds
  • 5 Baths
  • 6,682 Sq Ft

  217 W Boscawen St, Winchester, VA 22601

  Historic Water Street Inn a magnificent legacy residence, profitable Bed & Breakfast, or sophisticated professional office opportunity! Located in Winchester's Historic District, two blocks from Old Town Walking Mall! Six large bedrooms and five full baths, this historically significant property is one of a kind, offering private garden spaces, romantic terraces, sunlight filled porches, and

  Gillian Greenfield Coldwell Banker Premier

  217 W Boscawen St, Winchester, VA 22601
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  /43

  $399,900

  • 2 Beds
  • 2 Baths
  • 1,405 Sq Ft

  1851 Melvor Ln, Winchester, VA 22601

  Extremely well-maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottages 55+ community. This main-level living home features an open floor plan, vaulted ceiling, solar tubes for natural light, and a cozy gas fireplace in the living room. The primary suite offers a private bath, while a bright Florida room provides additional space for relaxing or entertaining. Step outside to

  RoxAnn Grimes RE/MAX Roots

  1851 Melvor Ln, Winchester, VA 22601
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  /7

  $1,100,000

  • Land
  • 2.3 Acres
  • $478,261 per Acre

  0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601

  2.3 Acre Outparcel on Pleasant Valley Road for Sale Neighbors include Walmart, Ross, Target, Panera Bread, Olive Garden, Petco, and the list goes on! Zoned CM1, ideal for auto sales, offices, retail, and flex development. All utilities to site. Outstanding proximity to massive commercial and multifamily growth. VA's fastest growing City in it's fastest growing commercial district. Almost 500'

  Gillian Greenfield Coldwell Banker Premier

  0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601

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