Winchester County VA Homes for Sale

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  $70,000

  • Land
  • 30,492 Sq Ft
  • $100,000 per Acre

  548 Fremont St, Winchester, VA 22601

  Build-ready lot in Winchester — a true blank canvas with water and sewer hookups already in place. Minutes to Old Town and I-81. Bring your builder and your vision!

  RoxAnn Grimes RE/MAX Roots

  548 Fremont St, Winchester, VA 22601
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  $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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  $300,000

  • 2 Beds
  • 1 Bath
  • 1,097 Sq Ft

  310 Bellview Ave, Winchester, VA 22601

  Classic Winchester charm awaits at 310 Bellview Avenue! This inviting Cape Cod combines character, convenience, and plenty of opportunity to make the space your own. Inside, you’ll find hardwood floors, comfortable living areas, two main-level bedrooms, a full bathroom, and an additional half bath upstairs. A full basement offers extra storage and future possibilities, while the detached one-car

  Cindy Greenya Keller Williams Realty

  310 Bellview Ave, Winchester, VA 22601
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  $364,900

  • 3 Beds
  • 3 Baths
  • 2,064 Sq Ft

  802 Appleseed Ct, Winchester, VA 22601

  NO HOA-City of Winchester on cul-de-sac with a spacious yard that feels like a private oasis.Charming and inviting townhome offering an unusual and versatile four-level floor plan with wonderful indoor and outdoor living spaces! The main level features a welcoming living room with a beautiful bay window, fireplace and built-in shelving, along with a dining room accented by crown molding and chair

  Darcy Amburn Colony Realty

  802 Appleseed Ct, Winchester, VA 22601
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  /19

  $395,990

  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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  /17

  $396,190

  New Construction

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

  660 Arden Ct, Winchester, VA 22601

  660 Arden Court is an attractive new 3 level townhome with brick backing to trees 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, white cabinets, and stainless-steel appliances.

  D.R. Horton Builder

  660 Arden Ct, Winchester, VA 22601
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  /19

  $393,495

  New Construction

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

  652 Arden Ct, Winchester, VA 22601

  652 Arden Court is an attractive new 3 level townhome with brick backing to trees 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, white cabinets, and stainless-steel appliances.

  D.R. Horton Builder

  652 Arden Ct, Winchester, VA 22601
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  /51

  $499,900

  • 3 Beds
  • 3 Baths
  • 1,564 Sq Ft

  510 S Cameron St, Winchester, VA 22601

  Step into a piece of Winchester history, thoughtfully restored and completely renovated in 2025 while preserving the character and craftsmanship that make this historic home so special.Originally built in 1865, this downtown Winchester property has been extensively updated from top to bottom, blending modern comfort with carefully preserved historic details. The kitchen was returned to

  

  Brock Harris

  Samson Properties

  510 S Cameron St, Winchester, VA 22601
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  /26

  $325,000

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  2817 Papermill Rd, Winchester, VA 22601

  Welcome to 2817 Papermill Road, a beautifully maintained home that reflects true pride of ownership from the moment you arrive. Situated on an impressive approximately 0.35-acre lot, this property offers a wonderful combination of space, comfort, and convenience all while being just minutes from everything Winchester has to offer. The home has been thoughtfully cared for and kept in excellent

  Kevin Rodriguez Weichert, REALTORS

  2817 Papermill Rd, Winchester, VA 22601
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  $629,000

  • 4 Beds
  • 2.5 Baths
  • 2,810 Sq Ft

  507 S Stewart St, Winchester, VA 22601

  If you've been waiting for a home that offers both character and modern convenience, this one deserves a close look. This all-brick, charming Cape Cod is located on a beautiful tree-lined street in the heart of Winchester with more space & versatility than meets the eye. Cross the threshold into the large, welcoming foyer and let your gaze take it all in...Large living room, large dining room,

  Angela Duncan MarketPlace REALTY

  507 S Stewart St, Winchester, VA 22601
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  $471,000

  • 3 Beds
  • 2.5 Baths
  • 2,260 Sq Ft

  421 Longview Ave, Winchester, VA 22601

  A must see property! This is a beautifull well kept colonial house with 3 bedrooms, 2 full bath and 1 half bath. The basement is unfinish but is ready to be build. As you enter the main level, you will see a nice welcoming livingroom, diningroom and beautiful granite countertops in the kitchen, with stainless steel appliances and high effitiency washer and dryer to the side. From the kitchen you

  Valentin Bonilla Samson Properties

  421 Longview Ave, Winchester, VA 22601
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  /57

  $599,990

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,386 Sq Ft

  112 Worsham Terrace, Winchester, VA 22602

  Situated on a desirable cul-de-sac homesite backing to community open space, this thoughtfully designed home offers the perfect blend of comfort and functionality. The main level features a spacious owner's suite, formal dining room, laundry room, powder room, and an open-concept kitchen overlooking the living and dining areas. The kitchen includes quartz countertops, an island with seating,

  Victoria Clark D R Horton Realty of Virginia LLC

  112 Worsham Terrace, Winchester, VA 22602
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  $748,900

  • 5 Beds
  • 3 Baths
  • 5,430 Sq Ft

  416 Briarmont Dr, Winchester, VA 22601

  Classic all-brick home in a highly desirable Winchester location! Well maintained and thoughtfully designed, this five bedroom, three full bath home offers timeless character, spacious living areas and exceptional convenience. The main level features a gracious living room with fireplace, cozy den with fireplace and bookshelves and a primary bedroom on the main level. Four additional bedrooms

  John Schroth Colony Realty

  416 Briarmont Dr, Winchester, VA 22601
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  $735,000

  • 3 Beds
  • 2.5 Baths
  • 2,572 Sq Ft

  1748 Handley Ave, Winchester, VA 22601

  Exceptional space, thoughtful updates, and tremendous future potential come together in this impressive home! With a brand-new HVAC system, freshly painted interior and exterior, a freshly painted deck, and beautifully refreshed hardwood floors in the living room, much of the work has already been done for the next owner. Seller has obtained a recent professional appraisal; contact listing agent

  Barbara Smith RE/MAX Real Estate Connections

  1748 Handley Ave, Winchester, VA 22601
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  $299,500

  • 3 Beds
  • 1.5 Baths
  • 1,138 Sq Ft

  621 Watson Ave, Winchester, VA 22601

  Fresh, stylish, and move-in ready! Welcome to 621 Watson Avenue, a beautifully refreshed 3-bedroom, 1.5-bath duplex offering a wonderful blend of classic character and modern updates. Step inside to find freshly painted walls and beautiful hardwood floors that create a bright, inviting atmosphere throughout the main living areas.The updated kitchen features new cabinetry and stainless steel

  Caleb Fowler Samson Properties

  621 Watson Ave, Winchester, VA 22601
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  /39

  $384,990

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  HOMESITE 126 Monteith Dr, Winchester, VA 22601

  The most affordable townhomes in Winchester City! END OF ROW Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home backing to trees for added privacy and peaceful views. Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room ***OFFERING UP TO $5K IN

  DRB Homes Builder

  HOMESITE 126 Monteith Dr, Winchester, VA 22601
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  $325,000

  • 4 Beds
  • 2 Baths
  • 1,592 Sq Ft

  805 S Kent St, Winchester, VA 22601

  Welcome home! This beautifully maintained two-level home offers 4 bedrooms and 2 full bathrooms in the heart of Winchester. Warm and inviting, the home features a comfortable, functional layout with classic charm and thoughtful updates throughout. Pride of ownership is evident in every detail, both inside and out. Enjoy spacious living areas, a fully fenced yard perfect for relaxing or

  Carolina Mosquera Weichert, REALTORS

  805 S Kent St, Winchester, VA 22601
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  $450,000

  • 4 Beds
  • 2 Baths
  • 2,493 Sq Ft

  501 Fox Dr, Winchester, VA 22601

  Welcome to this beautifully updated 4 bedroom, 2 full bath home in the heart of Winchester City! This move in-ready property offers fresh paint throughout, newly installed laminate flooring, new carpet in the bedrooms and new ceiling fans, and a fully finished basement providing additional living space. The kitchen features a new dishwasher, while recent updates include a new dryer, toilet, and

  Jacob Schuttinger Coldwell Banker Premier

  501 Fox Dr, Winchester, VA 22601
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  /30

  $409,000

  • 4 Beds
  • 1 Bath
  • 1,768 Sq Ft

  322 E Piccadilly St, Winchester, VA 22601

  Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless character meets modern sophistication in one of Winchester’s most convenient and walkable locations. The large covered front porch immediately sets the tone—an inviting space for morning coffee or relaxed evening

  LESLIE WEBB Long & Foster Real Estate, Inc.

  322 E Piccadilly St, Winchester, VA 22601
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  /93

  $355,000

  • 2 Beds
  • 2 Baths
  • 1,234 Sq Ft

  1847 Melvor Ln, Winchester, VA 22601

  Come see what makes Willow Lawn, a 55+ community, such a desirable place to call home! This inviting one owner Winchester home offers a comfortable blend of charm, functionality, and everyday convenience. The Floorplan is open and contemporary. The Great Room has Cathedral Ceilings and is very spacious. The grounds are taken care of by the community so life is easy. One level living w/ newer

  Lisette Turner Century 21 Redwood Realty

  1847 Melvor Ln, Winchester, VA 22601
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  /40

  $359,000

  • 3 Beds
  • 1.5 Baths
  • 1,710 Sq Ft

  812 Appleseed Ct, Winchester, VA 22601

  Nestled on a quiet cul-de-sac surrounded by mature trees in the highly desirable Orchard Hills Subdivision with no HOA fees or restrictions, this traditional all-brick home features 3 bedrooms, 1.5 bathrooms, a 2-car driveway, and three beautifully finished levels of move-in-ready living space. From the tree-lined sidewalks and charming street lighting, you are welcomed onto a main level boasting

  Feletia Sharples Realty FC, LLC

  812 Appleseed Ct, Winchester, VA 22601
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  /19

  $393,190

  New Construction

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

  644 Arden Ct, Winchester, VA 22601

  644 Arden Court is an attractive new 3 level townhome with brick backing to trees 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, white cabinets, and stainless-steel appliances.

  D.R. Horton Builder

  644 Arden Ct, Winchester, VA 22601
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  /63

  $699,000

  • 7 Beds
  • 5 Baths
  • 4,736 Sq Ft

  2700 Loyalty Ct, Winchester, VA 22601

  Welcome to 2700 Loyalty Court—a beautifully maintained showcase home offering nearly 5,000 square feet of unmatched versatility in one of Winchester City’s most coveted locations. Commanding a prime corner lot on a peaceful cul-de-sac, this residence immediately captivates with its timeless stone-and-vinyl exterior, inviting covered front porch, and unmistakable curb appeal. Step inside to a

  Dan Whitacre Colony Realty

  2700 Loyalty Ct, Winchester, VA 22601
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  /33

  $429,000

  • 3 Beds
  • 2 Baths
  • 1,544 Sq Ft

  1412 S Loudoun St, Winchester, VA 22601

  Awesome Interior Photo's Coming Soon! Step inside this tastefully renovated brick ranch and feel instantly at home. Offering three comfortable bedrooms and two full baths, this property blends classic charm with thoughtful updates throughout. The main level features a bright, welcoming layout perfect for everyday living, while the lower level opens the door to exceptional flexibility — complete

  LESLIE WEBB Long & Foster Real Estate, Inc.

  1412 S Loudoun St, Winchester, VA 22601
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  /2

  $350,000

  • 3 Beds
  • 1.5 Baths
  • 1,507 Sq Ft

  1048 Woodland Ave, Winchester, VA 22601

  Nestled in a charming neighborhood, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 1954, this brick beauty exudes timeless appeal while providing modern living spaces that cater to today's lifestyle. With 1,507 square feet of thoughtfully designed space, this residence features three cozy bedrooms and one and a half bathrooms, making it an ideal

  Shane Bowman RE/MAX Roots

  1048 Woodland Ave, Winchester, VA 22601
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  /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
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  /39

  $369,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,578 Sq Ft

  1414 S Braddock St, Winchester, VA 22601

  PRICE REDUCED $10,000. Come Check out this charming Cape Cod home in Winchester City, built in 1950 and beautifully renovated in 2026, offers a perfect blend of classic character and modern convenience. With 2 spacious bedrooms and 2 full bathrooms, including a luxurious walk-in shower, this residence is designed for comfort. The heart of the home features a bright kitchen equipped with stainless

  Richard Kozlowski Long & Foster Real Estate, Inc.

  1414 S Braddock St, Winchester, VA 22601
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  /51

  $420,000

  • 4 Beds
  • 3.5 Baths
  • 2,004 Sq Ft

  109 Marlow Ct, Winchester, VA 22602

  Don't miss this nearly new townhouse in Rossum Crossing! With 4 bedrooms, 3.5 bathrooms, over 2,000 square feet of finished space, and a one-car garage, this home offers plenty of room and a great layout for everyday living. The lower level features a private bedroom with its own full bathroom, including a tiled walk-in shower, along with direct access to the rear yard. Upstairs, you'll find a

  Crystal Dudurich ERA Liberty Realty

  109 Marlow Ct, Winchester, VA 22602
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  /25

  $250,000

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  1125 Conway St, Winchester, VA 22601

  Welcome to 1125 Conway Ave, a charming bungalow in Winchester City that's move-in ready and full of character! This cozy 2-bedroom, 1-bath home features beautiful hardwood floors and numerous recent updates, including a new roof, fresh interior paint, kitchen remodel, hallway and bathroom flooring, and a new stainless steel refrigerator. The deck has also been restored, providing a great spot to

  Curtis Siever NextHome Realty Select

  1125 Conway St, Winchester, VA 22601
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  /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
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  /52

  $369,990

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  229 Monteith Dr, Winchester, VA 22601

  The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room. ***OFFERING UP TO $5K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED

  Brittany Newman DRB Group Realty, LLC

  229 Monteith Dr, Winchester, VA 22601
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  /40

  $359,990

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  237 Monteith Dr, Winchester, VA 22601

  The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home backing to trees for added privacy and peaceful views. Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room***OFFERING UP TO $5K IN CLOSING

  Brittany Newman DRB Group Realty, LLC

  237 Monteith Dr, Winchester, VA 22601
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  $499,999

  • 4 Beds
  • 3.5 Baths
  • 2,524 Sq Ft

  2643 Middle Rd, Winchester, VA 22601

  Location, Location, Location! NO HOA!!! Priced below assessed value! Hardwood floors on the main level. Formal living and dining room leads to the Family room with stone fireplace, breakfast nook and kitchen. Step out on to the deck to enjoy the views. Large fenced level backyard. Large Primary suite with sitting room and luxury bath. Good sized bedrooms, one with an attached bath. Lower level

  Lorraine Arora Berkshire Hathaway HomeServices PenFed Realty

  2643 Middle Rd, Winchester, VA 22601
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  $530,000

  • 5 Beds
  • 3.5 Baths
  • 2,417 Sq Ft

  1605 Fort Braddock Ct, Winchester, VA 22601

  Fort Braddock Heights (Winchester City) - Detached Two-Level Home with Five (5) Bedrooms + Three (3) Full Bathrooms + One (1) Half Bathroom *Approx. 2,417 Finished Square Feet Across Two (2) Levels *Built 1992 *0.23 Acre Lot (Approx. 10,019 Square Feet) *One (1) Car Attached Front-Loading Garage + Paved Driveway *Second Garage Bay Converted to Oversized Main Level Laundry and Storage with Bonus

  Timothy Kotlowski Long & Foster Real Estate, Inc.

  1605 Fort Braddock Ct, Winchester, VA 22601
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  $750,000

  • Studio
  • 3,484 Sq Ft

  224 Sharp St, Winchester, VA 22601

  Rare Historical Winchester Investment Opportunity – Three Properties in One LocationAn outstanding investment opportunity awaits in the heart of Winchester City. This unique portfolio comprises three properties positioned along the same street, offering exceptional potential for developers, investors, or those seeking a landmark project for multi-unit rentals or commercial development. Both

  Stacey Rowe Real Broker LLC

  224 Sharp St, Winchester, VA 22601
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  /97

  $1,100,000

  • 6 Beds
  • 6 Baths
  • 6,789 Sq Ft

  1030 Breckinridge Ln, Winchester, VA 22601

  Welcome to this inviting, beautifully maintained 6-bedroom, 4-full-bathroom, 2-half-bathroom all-brick home in the desirable Meadow Branch subdivision in Winchester, Virginia. Offering over 6,000 square feet of finished living space, this impressive residence combines generous room sizes, timeless construction, exceptional storage, and comfortable living spaces designed for both everyday life and

  Joleen Haymaker Samson Properties

  1030 Breckinridge Ln, Winchester, VA 22601
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  /29

  $369,999

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

  2919 S Pleasant Valley Rd, Winchester, VA 22601

  Home Warranty for the Buyer + Bonus for the Buyer’s Agent with a Ratified Contract in September! 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

  Patricia Rivas Plata Keller Williams Realty Dulles

  2919 S Pleasant Valley Rd, Winchester, VA 22601
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  /39

  $425,000

  $9K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,277 Sq Ft

  422 S Loudoun St, Winchester, VA 22601

  PRICED BELOW RECENT APPRAISED VALUE. Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the charm of yesteryear this home offers the conveniences of modern living. Traditionally appointed, the main level of the home provides the perfect separation of spaces with a large formal living room, dining room, gourmet kitchen,

  Dana Cloud Realty ONE Group Old Towne

  422 S Loudoun St, Winchester, VA 22601
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  /8

  $289,900

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

  2640 Limestone Ct, Winchester, VA 22601

  Nestled in the charming City of Winchester, this exquisite end-of-row townhouse has undergone a remarkable transformation, with major renovations completed in 2026 that elevate it to a new standard of luxury living. The timeless Colonial architectural style, complemented by a classic brick exterior, exudes elegance and warmth, inviting you to experience a lifestyle of comfort and sophistication.

  Meridee Powars Link Realty Services LLC

  2640 Limestone Ct, Winchester, VA 22601
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  /73

  $615,000

  • 5 Beds
  • 3.5 Baths
  • 3,626 Sq Ft

  922 Wayne Dr, Winchester, VA 22601

  Welcome home to this beautifully updated brick-front residence in the City of Winchester, where a thoughtful floor plan, generous living spaces with 9' ceilings on the main and upper levels, and meaningful improvements come together across three finished levels.The main level is designed for connection and comfort, beginning with a two-story foyer that opens into an airy, open-concept layout.

  Katrina Smith Samson Properties

  922 Wayne Dr, Winchester, VA 22601

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