Winchester County VA Homes for Sale

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  $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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  /17

  $359,900

  • 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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  $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
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  $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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  $505,000 Coming Soon

  • 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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  /43

  $489,900 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft

  703 S Loudoun St, Winchester, VA 22601

  Location? Check. Beautiful federal-style architecture? Check. A separate dwelling unit? Check. Endless possibilities? Check!!! This amazing property, located within the Historic Winchester District, presents a one-of-a-kind opportunity to own a piece of history - all just minutes from the Old Town mall. The front of the main home dates back to 1856! You will surely fall in love with the wood

  Kristin Crosby Samson Properties

  703 S Loudoun St, Winchester, VA 22601
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  /2

  $300,000 Coming Soon

  • 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
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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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  /16

  $150,000

  • 1 Bed
  • 1 Bath
  • 585 Sq Ft

  528 Fremont St, Winchester, VA 22601

  OPPORTUNITY is knocking! This small and simple house could become an investment property, starter home, downsizing home, or single level living home for someone. With a smaller footprint, renovations would be minimal but have a huge impact. A major hidden benefit while living in town is the off street parking with a large driveway behind the home. OWNER FINANCING AVAILABLE.

  Michael Sprague Samson Properties

  528 Fremont St, Winchester, VA 22601
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  /12

  $549,900 Open House 2/07

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

  435 Mikey Ct, Winchester, VA 22601

  Welcome to 435 Mikey Court, a beautifully appointed home tucked within the highly desirable Village at Harvest Ridge, a premier 55+ community offering comfort, quality, and ease of living. Designed for effortless main-level living, this home features a well-thought-out open floorplan that connects the living, dining, and kitchen spaces, creating a warm and inviting atmosphere with generous room

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 530-3150

  435 Mikey Ct, Winchester, VA 22601
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  $589,000

  • 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, new carpet in all bedrooms, and fresh interior

  Barton Chasler Realty ONE Group Old Towne

  832 Winder Ct, Winchester, VA 22601
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  $429,900

  • 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
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  $439,990 New Construction

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

  1805 Harvest Dr, Winchester, VA 22601

  1805 Harvest Drive is an attractive new 3 level townhome with full brick front in Winchester, VA for February 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 appliances. The

  D.R. Horton Builder

  1805 Harvest Dr, Winchester, VA 22601
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  $449,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,939 Sq Ft

  1817 Harvest Dr, Winchester, VA 22601

  1817 Harvest Drive is an attractive new 3 level townhome with full brick front in Winchester, VA for February 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 appliances. The

  D.R. Horton Builder

  1817 Harvest Dr, Winchester, VA 22601
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  $429,990 New Construction

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

  1822 Blythe Way, Winchester, VA 22601

  1822 Blythe Way is an attractive new 3 level end townhome with full brick front in Winchester, VA for February 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, white cabinets, and stainless-steel

  D.R. Horton Builder

  1822 Blythe Way, Winchester, VA 22601
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  $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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  $320,000

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft

  1610 S Loudoun St, Winchester, VA 22601

  Welcome to this charming Cape Cod located in the heart of Winchester. Centrally situated just minutes from Old Town Winchester and Shenandoah University, this home offers both convenience and character.Step inside to a spacious living room featuring a cozy fireplace, which flows seamlessly into the kitchen and continues on to the dining room, creating an inviting layout for everyday living

  Heloisa Amar Samson Properties

  1610 S Loudoun St, Winchester, VA 22601
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  $249,000

  • Land
  • 0.36 Acre
  • $691,667 per Acre

  1001 Whittier Ave, Winchester, VA 22601

  If you want to build in the city limits, this is it! Located in an established neighborhood across from Whittier Park. Minutes to restaurants, shops, breweries, walking mall and more! Call today!

  Amy Mininberg Samson Properties

  1001 Whittier Ave, Winchester, VA 22601
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  /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
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  $374,990 New Construction

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

  226 Monteith Dr, Winchester, VA 22601

  Open House Saturday 1/24/26 from 11am until 4pm! 3 Level Townhome with Deck! Ready to move-in luxury 3 level/3-bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the lower level available! MOVE-IN READY! Explore Winchester’s new luxury townhome community. This three level home features three bedrooms, three and a half baths, and bright

  DRB Homes Builder

  226 Monteith Dr, Winchester, VA 22601
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  $389,990 Open Sun 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

  Holly Horne Poole New Home Star Virginia, LLC

  117 Boone Ct, Winchester, VA 22602
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  $440,000 Open Sat 1PM - 4PM

  • 4 Beds
  • 2 Baths
  • 2,408 Sq Ft

  519 Whitacre St, Winchester, VA 22601

  Ideally located within one of Winchester’s most desirable neighborhoods, Whittier Acres, and next to Winchester Medical Center, this spacious split-level home offers exceptional convenience paired with a rare sense of privacy in a quiet, established setting. Backing to mature trees, the backyard is a peaceful retreat where birds visit regularly and an established butterfly garden awaits its

  Katie Landi Jordan Samson Properties

  519 Whitacre St, Winchester, VA 22601
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  $379,990 New Construction

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

  217 Monteith Dr, Winchester, VA 22601

  3 Level Townhome with Box Bay Window! Ready to move-in Luxury 3 level/3-bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the basement available! 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

  DRB Homes Builder

  217 Monteith Dr, Winchester, VA 22601
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  $399,990 Open House 2/07

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

  214 Monteith Dr, Winchester, VA 22601

  END UNIT Luxury 3 level/3 bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the basement available!***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*MOVE-IN READY! Explore Winchester’s new luxury

  Brittany Newman DRB Group Realty, LLC

  214 Monteith Dr, Winchester, VA 22601
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  $360,000

  • Studio
  • 1,249 Sq Ft

  45 and 45 1/2 Race St, Winchester, VA 22601

  Investors Dream - $36,000 rental income, low maintenance, long term tenants in place. This is a great starter property for those looking to build a real estate portfolio or add to an existing one. Both apartments were completely rehabbed last year - new wiring and plumbing, new appliances, including washer and dryer, new carpet and vinyl plank flooring installed and fenced backyards. Situated

  Teri Domanski Corcoran McEnearney

  45 and 45 1/2 Race St, Winchester, VA 22601
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  /21

  $384,990 Open Mon 12PM - 4PM

  • 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
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  /16

  $465,000

  • 4 Beds
  • 2.5 Baths
  • 1,634 Sq Ft

  21 W Pall Mall St, Winchester, VA 22601

  This inviting Winchester home offers a comfortable blend of character, functionality, and everyday convenience. The welcoming front porch creates a warm first impression and provides an ideal place to relax, unwind, or enjoy time outdoors. The fenced-in backyard offers added privacy and flexibility, making it well suited for entertaining, gardening, or simply enjoying open-air living. A private

  Sarah Reynolds Keller Williams Realty

  21 W Pall Mall St, Winchester, VA 22601
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  $479,900 Open Sat 1PM - 4PM

  • 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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  $569,900

  • 3 Beds
  • 2 Baths
  • 2,154 Sq Ft

  1412 Magruder Ct, Winchester, VA 22601

  Finally, an all-brick, very well-maintained home in The Downs of Meadow Branch. Just shut the door and go on vacation or away for the winter- the downs mows your lawn, cuts your grass, and shovels the snow.

  John Schroth Colony Realty

  1412 Magruder Ct, Winchester, VA 22601
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  $476,500

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

  407 Jefferson St, Winchester, VA 22601

  ON SALE! 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! Perhaps a

  Gillian Greenfield Coldwell Banker Premier

  407 Jefferson St, Winchester, VA 22601
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  $850,000

  • 4 Beds
  • 4 Baths
  • 4,417 Sq Ft

  1006 Armistead St, Winchester, VA 22601

  Grand Elegance with Endless Potential – Spacious 3-Sided Brick Colonial with Soaring Ceilings and Room to Grow! Set on an elevated lot with commanding curb appeal, this stately all-brick-front Colonial welcomes you with timeless architecture and a wide front and back lawn. This spacious 4-bedroom, 2.5-bath home is full of opportunity for buyers ready to make it their own. Priced below tax value,

  Chris Craddock EXP Realty, LLC

  1006 Armistead St, Winchester, VA 22601
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  $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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  /40

  $365,000

  • 4 Beds
  • 2 Baths
  • 1,534 Sq Ft

  323 Russelcroft Rd, Winchester, VA 22601

  Looking for a home in amazing shape for your buyers? You've found it. 2108sf total living space. Beautiful cared for by the homeowners. 3 bedrooms 2 full baths detached home.Beautiful Detached home with 3 bedrooms and 2 full baths + bonus room on the basement isfull finished with a family room. Looking for a home in amazing shape for your buyers? You've found it. 2108sf total living

  Alexandra Brown Spring Hill Real Estate, LLC.

  323 Russelcroft Rd, Winchester, VA 22601
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  /2

  $415,000 Coming Soon

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

  307 Fox Dr, Winchester, VA 22601

  Exceptional, spacious one level home close to the Medical Center, shopping and downtown. The generously sized living room has lots of built in shelving and a wood burning fireplace. with a mantle and hearth. Sliding doors in the living room provide access to the lovely patio and fenced rear yard. The home has an attic with pull down stairs and plenty of storage area in the attic. There is also an

  Darcy Amburn Colony Realty

  307 Fox 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 $7K 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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  /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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  /22

  $295,000

  • 3 Beds
  • 1.5 Baths
  • 1,152 Sq Ft

  534 N Kent St, Winchester, VA 22601

  Just minutes from the downtown walking mall, this single family home offers three bedrooms, stainless steel appliances and granite countertops, a great yard, off street parking, and a front porch. The home comes with an electric car charger usable for all brands.

  Katie Landi Jordan Samson Properties

  534 N Kent St, Winchester, VA 22601
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  /45

  $469,900

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

  312 W Cecil St, Winchester, VA 22601

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

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 302-5771

  312 W Cecil St, Winchester, VA 22601
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  /24

  $600,000

  • 5 Beds
  • 4 Baths
  • 3,550 Sq Ft

  681 Hillman Dr, Winchester, VA 22601

  No HOA and only two years young, this beautifully designed and meticulously maintained home offers the perfect blend of comfort, style, and modern functionality. A rare main-level bedroom with a full bath provides flexibility and convenience for guests or multi-generational living. Throughout the home, designer finishes and elegant details elevate every space, including a spa-inspired bathroom

  Sarah Reynolds Keller Williams Realty

  681 Hillman Dr, 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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