Winchester County VA Homes for Sale

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  /23

  $320,000

  • 3 Beds
  • 1 Bath
  • 1,134 Sq Ft

  27 Jackson Ave, Winchester, VA 22601

  Completely renovated and move-in ready, this charming 3 bedroom, 1 bath home is ideally located just minutes from downtown Winchester's shops, dining, and entertainment. Inside, you'll find beautiful hardwood floors throughout and a brand new kitchen and fully renovated bathroom. Major updates to the home include a new roof, new windows, new HVAC system, new hot water heater and new electric all

  

  Mikiala Whitacre

  ERA Oakcrest Realty, Inc.

  (540) 590-5591

  27 Jackson Ave, Winchester, VA 22601
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  /9

  $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
• 

  

  /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
• 

  

  

  /27

  $369,990 New Construction

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

  206 Monteith Dr, Winchester, VA 22601

  OPEN HOUSE: Friday - Sunday 1pm - 3pm MOVE-IN READY! 3 Level Townhome With Over 1,700 Finished Square Feet! The Bedford II 3 level townhome with a box bay window with 1 car garage. It is fully finished top to bottom. The front door with the electronic Ring door camera leads directly into the spacious lower level recreation room. The foyer with luxury vinyl plank, a double coat closet, door access

  DRB Homes Builder

  206 Monteith Dr, Winchester, VA 22601
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  /30

  $399,990 New Construction

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

  214 Monteith Dr, Winchester, VA 22601

  OPEN HOUSE: Saturday - Sunday 1pm - 3pm 3 Level Townhome with 3 bedrooms! Come and see Winchester's BRAND NEW LUXURY TOWNHOME COMMUNITY. Step into modern living with this stunning 3-level townhome offering 3 bedrooms and 3.5 baths. Designed for comfort and style, this home features box bay windows in both the front and rear, filling every floor with natural light. Enjoy the convenience of an

  DRB Homes Builder

  214 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

  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

  $371,990 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
• 

  /2

  $469,900 Coming Soon

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

  1025 S Loudoun St, Winchester, VA 22601

  Prepare to be wowed by this stunning renovation in downtown Winchester! This charming Colonial has been fully remodeled and is ready for new owners. No detail was spared—original features were thoughtfully preserved to maintain the home’s historic charm, while modern conveniences were added throughout for everyday living. The original hardwood floors were refinished and run throughout the house,

  Heloisa Amar Samson Properties

  1025 S Loudoun St, 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
• 

  

  /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
• 

  

  /45

  $449,000 Coming Soon

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

  25 W Southwerk St, Winchester, VA 22601

  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 the perfect balance of neighborhood tranquility and

  Dan Whitacre Colony Realty

  25 W Southwerk St, Winchester, VA 22601
• 

  

  /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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  /115

  $469,999

  • 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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  /42

  $474,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 3 Baths
  • 2,805 Sq Ft

  407 Jefferson St, Winchester, VA 22601

  A TURN KEY classic colonial, fully UPDATED, and WALKABLE to downtown! *3 LEVELS totalling 2568 SF* Stroll to the restaurants in Old Town, enjoy the activities at Handley, or walk to the trails at MSV! NEW roof, HVAC, privacy fencing, custom paint and built-in cabinetry, plus new stainless steel appliances, including washer/dryer. Get creative in the FINISHED LOWER LEVEL with walk-out! Perhaps a

  Gillian Greenfield Coldwell Banker Premier

  407 Jefferson St, Winchester, VA 22601
• 

  

  /10

  $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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  /20

  $389,900

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  1885 Rosser Ln, Winchester, VA 22601

  Welcome to 1885 Rosser Lane. Located in one of Winchester's sought after 55+ retirement communities, Willow Lawn Cottages. This cute and cozy 2 bedroom 2 full bath home features spacious one level living with vaulted ceilings, den/office, sunroom, gas fireplace, separate laundry room, walk in closets, 1 car garage and more.

  Misty Miller OliveTree Property Group, LLC

  1885 Rosser Ln, Winchester, VA 22601
• 

  

  /3

  $409,990 New Construction

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

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

  Attached 1-car garage or flex option. Open concept kitchen with optional island opens to country kitchen, sun room, and living room. Alternative main level option available. Optional choices available include a study and a fireplace. Owner’s suite with a generous walk-in closet, dual vanity, and seated shower.

  DRB Homes Builder

  0 Tbd Weems Ln Unit 38608305, Winchester, VA 22601
• 

  

  /42

  $415,000

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  307 Fox Dr, Winchester, VA 22601

  Ready for occupancy and fast settlement! Exceptional, spacious one-level home ideally located near the Medical Center, the Museum of the Shenandoah Valley, shopping, and downtown. This well-maintained property features newly refinished hardwood floors. The generously sized living room offers extensive built-in shelving and a wood-burning fireplace with mantle and hearth. Sliding glass doors open

  Darcy Amburn Colony Realty

  307 Fox Dr, Winchester, VA 22601
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  /37

  $386,500

  • 3 Beds
  • 1.5 Baths
  • 1,416 Sq Ft

  31 W Whitlock Ave, Winchester, VA 22601

  Charming Home Near Handley High School – Move-In Ready! Welcome to this beautifully updated home in a fantastic downtown location—just a short walk to shops, restaurants, and all that the vibrant city center has to offer. This property features a converted garage that now serves as a versatile studio space, perfect for a home office, art studio, or guest suite. Enjoy a spacious, fenced-in

  Meridee Powars Link Realty Services LLC

  31 W Whitlock Ave, Winchester, VA 22601
• 

  

  /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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  /15

  $279,999 Coming Soon

  • 2 Beds
  • 1.5 Baths
  • 954 Sq Ft

  407 van Fossen St, Winchester, VA 22601

  Welcome to this charming 2-bedroom, 1.5-bath home in Winchester! Featuring a recently replaced roof (2024) and double-hung windows, this home combines character and functionality. The main floor offers a bedroom with half bath, perfect for guests or home office use, while upstairs boasts a large bedroom with full bath. Enjoy cozy evenings by the brick wood-burning fireplace and the beautiful

  Michele Gibson Samson Properties

  407 van Fossen St, Winchester, VA 22601
• 

  

  /17

  $349,900

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  2952 Grace St, Winchester, VA 22601

  Charming one level, 3-bedroom, 1 full bath home conveniently located in the heart of Winchester. Recently remodeled with new flooring throughout, updated bathroom, and modern fixtures. Thoughtful updates make this home move-in ready and ideal for easy, single-level living. Close to shopping, dining, and commuter routes.

  Carolina Mosquera Weichert, REALTORS

  2952 Grace St, Winchester, VA 22601
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  /33

  $589,000 Open Sat 11AM - 1PM

  • 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, new carpet in all bedrooms, and fresh interior

  Barton Chasler Realty ONE Group Old Towne

  832 Winder Ct, Winchester, VA 22601
• 

  /2

  $290,000 Open Sun 12PM - 2PM

  • 2 Beds
  • 1 Bath
  • 817 Sq Ft

  580 York Ave, Winchester, VA 22601

  Charming and completely updated! This beautiful home features a brand-new kitchen with new appliances, an updated bathroom, newly installed HVAC system, and a new water heater. Truly move-in ready and waiting for its next owner!

  Yoselin Mejia The Vasquez Group LLC

  580 York Ave, Winchester, VA 22601
• 

  

  /59

  $889,000 Coming Soon

  • 5 Beds
  • 4.5 Baths
  • 4,957 Sq Ft

  1540 Meadow Branch Ave, Winchester, VA 22601

  An exceptional offering of luxury living in the City of Winchester, this stately brick residence presents 4,958 square feet or refined, custom-designed living space. The home features 5 generously sized bedrooms and 4.5 beautifully appointed bathrooms, thoughtfully crafted for both elegant entertaining and everyday comfort. Rich architectural details and custom finishes are showcased throughout,

  John Schroth Colony Realty

  1540 Meadow Branch Ave, Winchester, VA 22601
• 

  /2

  $300,000

  • 3 Beds
  • 1 Bath
  • 1,789 Sq Ft

  501 Battle Ave, Winchester, VA 22601

  Unwind on the covered front porch of this charming stone Cape Cod, ideally located on a spacious corner lot with sidewalks and a large, fenced backyard. Inside, the inviting living room features hardwood floors and a brick gas-log fireplace—perfect for cozy evenings. Hardwood flooring continues throughout the home, complemented by a convenient kitchen and dining combination. Two bedrooms are

  Susan Caulfield Pearson Smith Realty, LLC

  501 Battle Ave, Winchester, VA 22601
• 

  /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
• 

  

  /52

  $374,900

  • 3 Beds
  • 1 Bath
  • 907 Sq Ft

  217 Myrtle Ave, Winchester, VA 22601

  Newly renovated and move-in ready! Everything is brand new in this super cute ranch home with a craftsman-style feel. Located in the City of Winchester in Northwestern Hills, schedule your appointment to see this stunning 3 BR 1 BA home with detached garage. New vinyl siding, roof, heat pump, GE appliances, cabinets, granite countertops, undercabinet lighting, flooring, landscaping, doors,

  Pamela Foltz Realty ONE Group Old Towne

  217 Myrtle Ave, 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
• 

  

  /10

  $499,000

  • Land
  • 0.09 Acre
  • $5,544,444 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
• 

  

  /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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  /44

  $505,000 Open Sat 11AM - 1PM

  • 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
• 

  /2

  $199,900

  • Land
  • 0.16 Acre
  • $1,249,375 per Acre

  1415 Ramseur Ln, Winchester, VA 22601

  Steve DuBrueler Coldwell Banker Premier

  1415 Ramseur Ln, Winchester, VA 22601
• 

  

  /60

  $420,000 Open House 2/21

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

  139 Biscane Ct, Winchester, VA 22602

  Beautifully upgraded 2018 townhome packed with style, comfort, and smart-home features! Step into a bright living room with built-in surround sound—perfect for movie nights and entertaining. The kitchen and laundry were refreshed in 2023 with a new refrigerator, dishwasher, washer & dryer, plus a water softener system and elegant hardwood stairs with an upgraded upper level foyer.Out back,

  Roberto Cardoza Orellana Pearson Smith Realty, LLC

  139 Biscane Ct, Winchester, VA 22602
• 

  

  /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. . Update, main house is now rented and income is over $15,000 per month. This property is also improved with large block garage and a separate 4 car garage with over 18' ceilings. Perfect for the automotive enthusiast or you can continue to

  Meridee Powars Link Realty Services LLC

  908 Cedar Creek Grade, Winchester, VA 22601
• 

  

  /21

  $384,990 Open Wed 12PM - 3PM

  • 3 Beds
  • 4 Baths
  • 1,989 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 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 pantry closet, and a breakfast nook. This

  Holly Horne Poole New Home Star Virginia, LLC

  105 Boone Ct, Winchester, VA 22602
• 

  

  /47

  $310,000

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft

  712 Frederick Ave, Winchester, VA 22601

  Charming Cape Cod in a highly desirable Winchester location! This sweet home offers a rare bonus—plenty of off-street parking from the alley plus a one-car garage (24x20), making everyday living (and entertaining) a breeze. INTERIOR: You’ll find a main-level primary bedroom along with cozy living spaces including a separate dining area, inviting living room, and a warm, comfortable den. Upstairs

  Jennifer Avery Crum Realty, Inc.

  712 Frederick Ave, Winchester, VA 22601
• 

  

  /34

  $429,900 Open Sat 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,219 Sq Ft

  945 Allen Dr, Winchester, VA 22601

  945 Allen Drive sits on a rare extra-wide double lot and showcases an in-ground swimming pool designed for both fun and relaxation. The pool features a brand-new liner, solar-powered heater to help keep the water comfortably warm, a sun shelf for lounging in shallow water, and a diving board for classic summer fun. The backyard is fully enclosed with a 6-foot vinyl privacy fence, creating a

  Barton Chasler Realty ONE Group Old Towne

  945 Allen Dr, Winchester, VA 22601
• 

  

  /47

  $479,900

  • 4 Beds
  • 2.5 Baths
  • 1,960 Sq Ft

  418 Circle Dr, Winchester, VA 22601

  New construction without the wait! This two-year-young home is like new and ready for its next owners. Enjoy a spacious open floor plan featuring LVP flooring throughout the main level, a modern kitchen with stainless steel appliances and a large center island. The main level also offers a private home office and a convenient half bath. Upstairs, retreat to a spacious primary suite complete with

  Heloisa Amar Samson Properties

  418 Circle Dr, Winchester, VA 22601

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