Winchester County VA Houses for Sale

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  $245,000 Open Sat 10AM - 12PM

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  423 Highland Ave, Winchester, VA 22601

  Charming Winchester Home – Priced to sell fast! Don't let this property slip away!This freshly updated home in the heart of Winchester offers incredible potential and versatility. Featuring off-street parking from the rear alley, a fresh coat of paint, and newly installed vinyl flooring downstairs, this property is move-in ready while leaving room for your personal

  

  Carlos Soares

  Samson Properties

  (540) 584-8746

  423 Highland Ave, Winchester, VA 22601
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  $344,900

  • 3 Beds
  • 1.5 Baths
  • 1,178 Sq Ft

  107 E Monmouth St, Winchester, VA 22601

  Price Reduction!! Charming Historic Home in Downtown Winchester – Move-In Ready!If you love timeless craftsmanship—think original wood floors, custom built-ins, and vintage doors—but still want the ease of modern living, this beautifully updated downtown Winchester home is calling your name!From the moment you step onto the inviting covered porch and through the front door, you’ll

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 619-5037

  107 E Monmouth St, Winchester, VA 22601
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  $869,500

  • 4 Beds
  • 4.5 Baths
  • 6,368 Sq Ft

  1517 Brookdale Ct, Winchester, VA 22601

  A rare opportunity to own the largest model in the Morlyn Hills neighborhood--more than 6500 square feet when including the fully finished basement. Situated on a premier lot and in immaculate, move-in-ready condition, this home is competitively priced and an exceptional value. This home features 4 bedrooms, 4.5 baths, and an impressive array of upgrades throughout.From the moment you enter

  

  Brock Harris

  Samson Properties

  (540) 596-5570

  1517 Brookdale Ct, Winchester, VA 22601
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  $690,000

  • 4 Beds
  • 2.5 Baths
  • 3,108 Sq Ft

  1950 Melvor Ln, Winchester, VA 22601

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  Kim Kroner

  Washington Dulles Real Estate Group

  (540) 453-8579

  1950 Melvor Ln, Winchester, VA 22601
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  $633,000

  • 4 Beds
  • 3 Baths
  • 3,959 Sq Ft

  320 Linden Dr, Winchester, VA 22601

  *2-1 Buydown being offered. Contact Agent for Details!* Experience generational refined living in this stunning luxury home just minutes from Winchester Medical Center. Designed for both elegance and comfort, this residence boasts exquisite crown moldings, rich wood floors, wainscoting, and cathedral ceilings throughout. The main level offers one-level living with an entry-level bedroom, a

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 274-0212

  320 Linden Dr, Winchester, VA 22601
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  $549,900 Coming Soon

  • 4 Beds
  • 3 Baths
  • 2,614 Sq Ft

  1729 Handley Ave, Winchester, VA 22601

  This immaculate 4-bedroom, 3-bath Cape Cod in sought-after Meadow Branch is move-in ready and full of thoughtful updates! From the welcoming foyer, the home flows seamlessly into a bright living room, spacious kitchen, and dedicated dining room. On the main level you'll also find two bedrooms and a full bath, perfect for guests or convenient one-level living.From the kitchen, step outside

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 698-5892

  1729 Handley Ave, Winchester, VA 22601
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  $515,000 Coming Soon

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft

  580 N Braddock St, Winchester, VA 22601

  Step into the charm of 1920s architecture seamlessly blended with today’s comforts. This beautifully restored 4-bedroom, 2.5-bath home offers over 2,200 sq ft of finished living space across three levels.Inside, you’ll find a bright, open main level with wide-plank flooring, a cozy family room with stacked stone gas fireplace, and a gourmet kitchen featuring a massive island, stainless

  Payton Polychrones Samson Properties

  580 N Braddock St, Winchester, VA 22601
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  $595,000

  • 4 Beds
  • 3.5 Baths
  • 2,976 Sq Ft

  2812 Ridgetop Ct, Winchester, VA 22601

  Welcome to this beautiful "picture perfect" brick front 4-bedroom, 3.5-bath home in the desirable Rolling Hills community of Winchester, VA. Perfectly located at the end of a cul-de-sac in an established (and sought after) neighborhood, this one-owner property has been meticulously maintained and is ready for its next chapter.Inside, you’ll find a spacious and inviting layout that includes a

  Sara Duncan RE/MAX Distinctive Real Estate

  2812 Ridgetop Ct, Winchester, VA 22601
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  $574,900

  • 3 Beds
  • 3 Baths
  • 2,726 Sq Ft

  2723 Windwood Dr, Winchester, VA 22601

  Premier Single-Level Living on a Private Cul-de-Sac! Nestled at the end of a quiet, prestigious cul-de-sac, this exquisite one-level ranch home presents a rare opportunity to acquire a property where meticulous maintenance meets masterful design. Shielded from through-traffic and enveloped by landscaped gardens. The home offers an immediate sense of arrival and tranquil privacy. A Grand and

  LESLIE WEBB Long & Foster Real Estate, Inc.

  2723 Windwood Dr, Winchester, VA 22601
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  $550,000

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

  121 N Washington St, Winchester, VA 22601

  A MUST SEE INSIDE!!!! This 2.5 story historic gem offers 3-4 beds, 2.5 baths and gourmet kitchen with brand new state of art appliances includes wine fridge, drawer style microwave, and pot filler. Formal living/dining room(s). Extras include den, office(s), nooks, and 3rd floor bonus room (perfect for kid's getaway). Laundry hook-ups on both main level and 2nd level. This home has been

  M. Kelly Walker RE/MAX Roots

  121 N Washington St, Winchester, VA 22601
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  $479,900

  • 3 Beds
  • 2.5 Baths
  • 1,976 Sq Ft

  703 National Ave, Winchester, VA 22601

  Fully renovated in 2025, this 3-bedroom, 2.5-bath home is ideally located within Winchester city limits—just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment, as well as Jim Barnett Park for outdoor recreation. Thoughtful updates and fresh landscaping enhance its curb appeal. Inside, you’ll find brand-new bathrooms with updated lighting, vanities,

  Jennifer Sacco RE/MAX Roots

  703 National Ave, Winchester, VA 22601
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  $650,000

  • 4 Beds
  • 2.5 Baths
  • 3,232 Sq Ft

  107 Roszel Rd, Winchester, VA 22601

  Spacious 4-bedroom, 2.5-bath home located in a desirable neighborhood just minutes from downtown. The main level features a family room, large eat-in kitchen with fireplace and bay window looking over the rear yard. The lower level features a game room with fireplace and opens onto the rear deck overlooking the pool. Upstairs offers four bedrooms, including a private owner’s suite. Outdoor

  John Scully Colony Realty

  107 Roszel Rd, Winchester, VA 22601
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  $450,000

  • 5 Beds
  • 3 Baths
  • 2,680 Sq Ft

  25 E Hart St, Winchester, VA 22601

  Welcome to 25 E Hart Street! Nestled in the heart of downtown Winchester, this beautifully updated 5-bedroom, 3-bath home is the perfect mix of charm, space, and convenience. Step inside to a bright, spacious living room where a wood-burning fireplace provides the perfect spot to relax and unwind. The updated kitchen is a dream with quartz countertops, stainless steel appliances, crisp white

  Liz Owings RE/MAX Roots

  25 E Hart St, Winchester, VA 22601
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  $699,999

  • 4 Beds
  • 5 Baths
  • 5,903 Sq Ft

  2530 Goldenfield Ln, Winchester, VA 22601

  Gorgeous home in the sought after Harvest Ridge neighborhood. Make this immaculately kept and updated home yours. Walk through the front door and be welcomed by a grand staircase. Follow it to the dining room or sitting room. Enjoy preparing a meal in the gourmet kitchen which is perfect for family meals or entertaining. Upstairs features 4 spacious bedrooms, including a master suite and 3

  Dave Spence RE/MAX Roots

  2530 Goldenfield Ln, Winchester, VA 22601
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  $419,900 Open Sun 1PM - 3PM

  • 5 Beds
  • 2 Baths
  • 2,363 Sq Ft

  707 S Braddock St, Winchester, VA 22601

  Welcome to this charming, fully remodeled home located in the heart of Winchester.Experience the timeless appeal of Old Winchester charm, just minutes from the vibrant walking mall, shops, restaurants, and the famous Apple Blossom Parade route. This beautifully remodeled home features LVP flooring throughout and a light-filled open floor plan that seamlessly blends historic character with

  Heloisa Amar Samson Properties

  707 S Braddock St, Winchester, VA 22601
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  $450,000

  • 4 Beds
  • 2 Baths
  • 1,092 Sq Ft

  1709 Reaves St, Winchester, VA 22601

  Please take off shoes and give feedback. Step into this beautifully cared-for home featuring new roof (2023) New HVAC System (2024) new LVP floors throughout the basement a spacious, inviting layout. The large kitchen offers plenty of room for meal prep and flows effortlessly into the dining and living rooms — perfect for family gatherings and entertaining. The finished basement boasts a

  Alexandra Brown Berkshire Hathaway HomeServices PenFed Realty

  1709 Reaves St, Winchester, VA 22601
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  $495,000

  • 4 Beds
  • 4 Baths
  • 1,627 Sq Ft

  201 Parkway St, Winchester, VA 22601

  Freshly Renovated Charmer in Winchester!Welcome to 201 Parkway Street, a freshly updated home in the heart of Winchester! Previously tenant-occupied, this property has been thoughtfully refreshed and is ready for new owners. Recent Updates Include:Fresh interior paint throughoutRenovated kitchen and bathUpdated fixtures and finishesClean, move-in

  Cherish Green Coldwell Banker Elite

  201 Parkway St, Winchester, VA 22601
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  $479,900

  • 6 Beds
  • 3 Baths
  • 3,900 Sq Ft

  811 Berryville Ave, Winchester, VA 22601

  PRICE REDUCED .....DO YOU HAVE A LARGE FAMILY AND NEED YOUR OWN SPACE. HERE IS A 6 BEDROOMS 3 BATHROOMS WITH A IN-LAW SUITE. OVER 3900+ SQ. FT FINISHED. OFF STREET PARKING FOR 6 CARS. SHED AND STILL ROOM TO RELAX OUTBACK.

  Richard Kozlowski Long & Foster Real Estate, Inc.

  811 Berryville Ave, Winchester, VA 22601
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  $289,900

  • 2 Beds
  • 2 Baths
  • 897 Sq Ft

  939 Woodland Ave, Winchester, VA 22601

  If you're looking to Downsize or Just Starting Out, Come Checkout this 1–2-bedroom 2 full bath home on 3 Levels Updated Kitchen with Stainless Steel Appliances, a Living room Dining room or Main level Bedroom with a Full bath attached. 2nd Level has a Bedroom Full bathroom and a loft area. Theres a unfinished Basement. Outside has a detach one car garage or Workshop with a Large Fenced Yard

  Richard Kozlowski Long & Foster Real Estate, Inc.

  939 Woodland Ave, Winchester, VA 22601
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  $275,000

  • 4 Beds
  • 2 Baths
  • 2,056 Sq Ft

  425 Beechcroft Rd, Winchester, VA 22601

  Here is your chance to get a home in Winchester City (John Handley school district) for an affordable price! This spacious brick rancher has what you call " good bones " and would be great for an rental investment or for a family looking to fix up themselves! There are 4 BR 2BA -and 2056 sq. ft on just over a quarter acre lot - You will absolutely love the built in bookshelves room, the

  michele bouve hoffman Pearson Smith Realty, LLC

  425 Beechcroft Rd, Winchester, VA 22601
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  $220,000

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft

  376 Charles St, Winchester, VA 22601

  Welcome home to laid-back charm in Winchester, VA! This inviting 3-bedroom, 1-bath home offers character, comfort, and plenty of breathing room to make your own. Inside, rich hardwood floors add warmth and continuity from the living room through the main level, while oversized windows flood the spacious bedrooms with natural light. The kitchen has plenty of cabinet space and a layout that

  Chris Craddock EXP Realty, LLC

  376 Charles St, Winchester, VA 22601
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  $349,900

  • 3 Beds
  • 2 Baths
  • 1,529 Sq Ft

  966 Woodstock Ln, Winchester, VA 22601

  Beautiful 3-bedroom, 2-bath split-foyer home in the heart of Winchester City! The main level features hardwood floors, an open kitchen/dining/living layout, and an eat-in kitchen with stainless steel appliances and upgraded countertops. The upper-level bath includes a tiled floor, vanity, and tub surround. The finished basement offers a spacious family room with a brick hearth, third bedroom,

  Anselm Tamasang Weichert Realtors - Blue Ribbon

  966 Woodstock Ln, Winchester, VA 22601
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  $369,900

  • 3 Beds
  • 2 Baths
  • 1,293 Sq Ft

  301 Liberty Ave, Winchester, VA 22601

  Welcome to 301 Liberty Ave, FALL IN LOVE with this charming all brick colonial residence situated in the heart of downtown Winchester. Just blocks away from the scenic walking mall you’ll discover an array of quaint shops, restaurants and the renowned Apple Blossom Parade route. This meticulously fully remodeled home boasts three spacious bedrooms and two luxurious bathrooms and is ready for a

  John Ashton Equity Realty

  301 Liberty Ave, Winchester, VA 22601
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  $299,900

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  20 E Hart St, Winchester, VA 22601

  This is a completely restored Winchester classic within walking distance to the downtown area and Handley High school. Located at the end of street. Home improvements include new HVAC, plumbing, electric and appliances. Interior pictures will follow as soon as painting has been completed.

  Meridee Powars Link Realty Services LLC

  20 E Hart St, Winchester, VA 22601
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  $375,000

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

  3 N Purcell Ave, Winchester, VA 22601

  This charming 4-bedroom bungalow, beautifully renovated in 2015, offers a perfect blend of modern comfort and classic appeal. Step inside to discover hardwood floors and crown moldings that enhance the inviting atmosphere. The country-style kitchen features ample table space, ideal for gatherings. With two full bathrooms and an entry-level bedroom, convenience is at your fingertips. Outside,

  mary kakouras On The Market Properties

  3 N Purcell Ave, Winchester, VA 22601
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  $325,000

  • 4 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  118 E Monmouth St, Winchester, VA 22601

  Charming Remodeled Colonial in Historic Old Town WinchesterYou’ll fall in love with this beautifully updated Colonial located in the heart of Winchester’s Historic District. Just steps from the Downtown Pedestrian Mall, Handley High School, and local shops and restaurants, this home blends timeless character with modern convenience.• 4 Bedrooms 1.5 Bathrooms• Restored original

  Scott Dawson Oakcrest Commercial LLC.

  118 E Monmouth St, Winchester, VA 22601
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  $349,900 Open Sat 12PM - 2PM

  • 3 Beds
  • 1 Bath
  • 1,192 Sq Ft

  316 Virginia Ave, Winchester, VA 22601

  Well maintained Colonial offering timeless character and modern potential in the heart of Winchester. This 3-bedroom, 1 1/2 bath home features beautiful hardwood floors, a spacious living area, formal dining room, and a well-sized kitchen with ample pantry storage. Finished basement with lots of space and also huge attic space with room for storage or play room. 15 Year old roof, new

  Berta Vasquez Samson Properties

  316 Virginia Ave, Winchester, VA 22601
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  $300,000

  • 3 Beds
  • 1 Bath
  • 1,710 Sq Ft

  428 Imperial St, Winchester, VA 22601

  Enjoy the ease of one-level living in the heart of Winchester City thats ready for your personal touches! Ideally located just minutes from shopping, dining, and local conveniences, this charming all-brick rancher with a full walk-up basement offers both comfort and functionality. The kitchen features space for a dining table, while the inviting living room boasts a cozy fireplace with a lovely

  Leah Clowser RE/MAX Roots

  428 Imperial St, Winchester, VA 22601
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  $349,990

  • 3 Beds
  • 2 Baths
  • 2,302 Sq Ft

  1005 Pennsylvania Ave, Winchester, VA 22601

  A classic brick ranch in Winchester, VA, has three bedrooms and two full bathrooms. The basement includes a separate entrance, a laundry area, a full bathroom, and an additional bonus room. Recent updates include: finished basement, new HVAC system, complete renovations of both bathrooms, new hardwood flooring, and an updated kitchen with new cabinets and countertops. No HOA restrictions.

  Nathalie Acosta Spring Hill Real Estate, LLC.

  1005 Pennsylvania Ave, Winchester, VA 22601
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  $370,000

  • 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 Berkshire Hathaway HomeServices PenFed Realty

  323 Russelcroft Rd, Winchester, VA 22601
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  $349,999

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

  505 Green St, Winchester, VA 22601

  Charming 3-Level Split Home in the Heart of Winchester!This split level home could be your forever home! Surrounded by parks, top-rated schools, and everyday amenities. Quick access to Route 7 and Interstate 81 commuting is breeze! Upstairs, you’ll find three generously sized bedrooms and a full bathroom, offering a peaceful seperate area. The main level boasts a warm and

  Julissa Rodriguez Vaze Realty

  505 Green St, Winchester, VA 22601
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  $515,000

  • 3 Beds
  • 2.5 Baths
  • 1,984 Sq Ft

  2623 Middle Rd, Winchester, VA 22601

  Welcome home to 2623 Middle Rd! Now with a Virtual Tour of this beautiful home! Located near all that Winchester has to offer, Middle Rd is a lovely private oasis to come home to. With a myriad of upgrades including a gorgeous screened in back porch, this home offers many conveniences, a spacious layout and bedrooms, and plenty of room for entertainment, hobbies, and whatever you can dream of.

  Nicole Lewis Coldwell Banker Premier

  2623 Middle Rd, Winchester, VA 22601
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  $925,000

  • 4 Beds
  • 4.5 Baths
  • 6,566 Sq Ft

  1509 Stone House Ct, Winchester, VA 22601

  Perched on the edge of the walking trail with fall views of the lake, and host to a private oasis in the back yard, you'll find 1509 Stone House Court, one of the largest homes in Morlyn Hills. The current owners added the pool, extensive hardscaping, retainer walls, privacy fence, and a composite deck with angled stairs to the pool area. Marble floors welcome you to a light filled foyer that

  Natalie Langford ERA Oakcrest Realty, Inc.

  1509 Stone House Ct, Winchester, VA 22601
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  $659,000

  • 4 Beds
  • 2.5 Baths
  • 3,512 Sq Ft

  2321 Stoneridge Rd, Winchester, VA 22601

  Must see colonial in Harvest Ridge on just over 0 .4 acre in the city of Winchester. The open foyer invites you into this spacious home boasting over 3500 sq.ft. plus a full walk-out basement, ready to finish for additional square footage. Large living and dining rooms with hardwood, den or office. Large kitchen features granite counters, stainless steel appliances, and a breakfast area that

  John Schroth Colony Realty

  2321 Stoneridge Rd, Winchester, VA 22601
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  $365,000

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

  1004 S Cameron St, Winchester, VA 22601

  PRICE REDUCED***Renovated Home in Winchester neighborhood.*** You’ll enter the house and find a spacious living room. As you continue walking, you’ll be led to the fully renovated kitchen. The kitchen features stainless steel appliances, including a new refrigerator, stove, microwave, dishwasher, new cabinets, and a granite countertop. The laundry room, located conveniently on the main level,

  Patricia Salgado Metas Realty Group, LLC

  1004 S Cameron St, Winchester, VA 22601
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  $950,000

  • 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,

  Amanda Slate Keller Williams Realty

  769 Seldon Dr, Winchester, VA 22601
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  $550,000

  • 4 Beds
  • 2.5 Baths
  • 1,798 Sq Ft

  720 S Kent St, Winchester, VA 22601

  Welcome to the beautifully preserved American Foursquare where music legend Patsy Cline once lived with her mother—and later, with her husband, Charlie Dick. Built in 1931, this four-bedroom, one-and-a-half-bath home blends timeless character with thoughtful updates, all wrapped in the charm of one of Winchester’s most historic neighborhoods.Inside, you’ll find nearly 1,800 square feet of

  Krissy Cruse Pearson Smith Realty, LLC

  720 S Kent St, Winchester, VA 22601
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  $359,900

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  553 Highland Ave, Winchester, VA 22601

  Completely remodeled! Come enjoy ALL new everything, new electric, new windows, luxury floors, freshlypainted walls and brand-new custom kitchen and bathrooms, and all new plumbing and electricthroughout, nothing has been left untouched! New Mini Split HVAC system. Large living room opens into a gorgeous wrap aroundpeninsula kitchen with brand new Samsung appliances, granite

  Lawrence Lessin Homes By Owner, Inc.

  553 Highland Ave, Winchester, VA 22601
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  $860,000

  • 5 Beds
  • 4.5 Baths
  • 5,254 Sq Ft

  1504 Brookdale Ct, Winchester, VA 22601

  MOTIVATED SELLER! Over 5,250 sq ft in this stunning 5BR/3.5BA Home in Prime Meadow Branch Area!Elegant 2-story foyer with sweeping staircase, coffered ceilings, and extended-height windows. Family room features floor-to-ceiling stone fireplace, open to gourmet kitchen with quartz countertops, stainless steel appliances, cooktop, and wall oven. Main level office with French doors, formal

  Julie Shiley Coldwell Banker Realty

  1504 Brookdale Ct, Winchester, VA 22601
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  $265,000

  • 4 Beds
  • 1 Bath
  • 1,732 Sq Ft

  1006 S Cameron St, Winchester, VA 22601

  Don't miss out on this opportunity to own this 5 bedroom/1 bath home. Hardwood flooring throughout. Large, covered front porch and rear deck. Less than a mile from downtown Winchester & the Handley Library. Close to schools. Off-street parking and a spacious backyard. Access to alley from backyard and off-street parking.

  Sheila Pack RE/MAX Roots

  1006 S Cameron St, Winchester, VA 22601

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