Winchester, VA Houses for Sale

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  /46

  $425,000

  • 3 Beds
  • 3 Baths
  • 1,806 Sq Ft

  133 Woodrow Rd, Winchester, VA 22602

  Welcome home to this charming split foyer in Carlisle Heights, ideally located on the east side of Winchester—just off Route 7 for an easy commute!Step inside to a light-filled interior featuring low-maintenance flooring throughout the main living areas and bedrooms, offering both comfort and practicality. The spacious, updated kitchen showcases white cabinetry, stainless steel

  

  Angie Ordonez

  NextHome Realty Select

  (540) 384-4063

  133 Woodrow Rd, Winchester, VA 22602
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• 

  

  

  /104

  $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 (Winchester city appraisal is above $900K) and an exceptional value This home features 4 bedrooms, 4.5 baths, and an impressive array of upgrades

  

  Brock Harris

  Samson Properties

  (540) 596-5570

  1517 Brookdale Ct, Winchester, VA 22601
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  /25

  $285,000

  • 2 Beds
  • 1 Bath
  • 856 Sq Ft

  621 Panther Dr, Winchester, VA 22602

  Wilde Acres offers peaceful country living just 15–20 minutes from Winchester City. The property spans three lots, for a total of approximately .75 acres, and features multiple outbuildings with power and heat. It's ideal for outdoor enthusiasts, nature lovers, and gardeners. The various outdoor spaces provide perfect areas for a workshop, recreation room, or extensive storage. This

  

  Lori Bales

  Keller Williams Realty

  (540) 779-1824

  621 Panther Dr, Winchester, VA 22602
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  /83

  $649,900

  • 4 Beds
  • 3.5 Baths
  • 2,923 Sq Ft

  114 Nassau Dr, Winchester, VA 22602

  Discover Your Dream Home on Nassau Drive! Welcome to this stunning Colonial home, nestled on a beautifully landscaped, lot within the highly sought-after Fieldstone community. Conveniently located just off Route 7, this spacious property offers the perfect blend of commuter-friendly access and the privacy and tranquility of a large, fully fenced backyard. This impressive home features four

  

  Brock Harris

  Samson Properties

  (540) 781-1173

  114 Nassau Dr, Winchester, VA 22602
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  /39

  $450,000 Coming Soon

  • 4 Beds
  • 3 Baths
  • 3,190 Sq Ft

  102 Shockey Cir, Winchester, VA 22602

  What a fantastic opportunity for 1-level living in a very desirable neighborhood within 3 minutes to downtown Winchester. This beautiful, all-brick home is located in Fairway Estates, also adjacent to the Winchester Country Club and golf course. It’s been very well-maintained of the years - move in ready and also happy to receive your updated touches. The full, large basement offers a guest

  

  Lori Bales

  Keller Williams Realty

  (540) 215-8959

  102 Shockey Cir, Winchester, VA 22602
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  /2

  $695,000 Coming Soon

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

  1950 Melvor Ln, Winchester, VA 22601

  Coming Soon Offered to Investor - Currently Rented NO DRIVEBY SHOWINGS

  

  Kim Kroner

  Washington Dulles Real Estate Group

  (540) 453-8579

  1950 Melvor Ln, Winchester, VA 22601
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  /45

  $500,000

  • 4 Beds
  • 3 Baths
  • 1,881 Sq Ft

  331 Ridge Ave, Winchester, VA 22601

  Assessed at $491K and only asking $500K. One level living on a beautiful corner lot in Whittier Acres - a very desirable neighborhood in Winchester City! Take advantage of the convenience of everything Winchester in this location - Winchester Medical Center, Downtown Winchester, the Museum of the Shenandoah Valley, and all of the popular restaurants. With 3 bedrooms and 2 bathrooms on the

  

  Lori Bales

  Keller Williams Realty

  (540) 253-4577

  331 Ridge Ave, Winchester, VA 22601
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  /45

  $490,000

  • 4 Beds
  • 3 Baths
  • 2,466 Sq Ft

  106 Poe Dr, Winchester, VA 22602

  Welcome to This Lovely Richmond American Homes, Pearl Model. A Beautiful Single Family Home Located On An Oversized Corner Lot. 4 Bedroom, 3 Full Bathrooms. Gourmet Kitchen Boasts Quartz Counters, Stainless Steel Appliances, A Grand Island For Quick Bites, And An Spacious, Open Concept Main Level. This Home Offers A Main Level Bedroom With A Full Bathroom and An Upstairs Bonus Room/ Loft.

  

  Adrian Blakeney

  EXP Realty, LLC

  (540) 805-8133

  106 Poe Dr, Winchester, VA 22602
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  /48

  $324,900

  • 4 Beds
  • 3 Baths
  • 2,606 Sq Ft

  128 Fox Dr, Winchester, VA 22601

  Welcome to 128 Fox Dr — a spacious, move-in ready home nestled in the heart of Winchester, offering three levels spanning over 2,600 square feet of flexible living space, with 4 bedrooms, 3 bathrooms, and unbeatable convenience! This Cape Cod-style home features a thoughtful layout with at least one bedroom and a full bathroom on every level. Step into the main level to discover hardwood floors

  

  MJ Frazier

  Real Broker, LLC

  (540) 513-5877

  128 Fox Dr, Winchester, VA 22601
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  /67

  $615,000

  • 4 Beds
  • 4 Baths
  • 2,760 Sq Ft

  162 Darby Dr, Winchester, VA 22602

  Nestled in the sought-after Ravenwing community, this stunning colonial home offers a perfect blend of comfort and style. Built in 2002, this well-maintained residence boasts nearly 3,000 finished square feet of thoughtfully designed living space, ideal for creating lasting memories. Step inside to discover a warm and inviting atmosphere, highlighted by a fully finished basement that provides

  Michael Elias Century 21 Redwood Realty

  162 Darby Dr, Winchester, VA 22602
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  /53

  $799,900

  • 5 Beds
  • 3.5 Baths
  • 3,928 Sq Ft

  977 W Parkins Mill Rd, Winchester, VA 22602

  Welcome to your dream retreat—set on 5 private acres just outside Winchester, this fully renovated home offers the perfect blend of luxury and land. With 5 spacious bedrooms and 3.5 beautifully updated bathrooms, this property is designed for comfort, functionality, and style.From the chef’s kitchen to the expansive living areas, every detail has been thoughtfully upgraded. Whether you're hosting

  Nicole Renzetti EXP Realty, LLC

  977 W Parkins Mill Rd, Winchester, VA 22602
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  /56

  $639,900

  • 3 Beds
  • 2.5 Baths
  • 1,968 Sq Ft

  281 Light Rd, Winchester, VA 22603

  Please note that this weekend's open house has been moved to Sunday, 5/18 - 12-2pm. Serene Ranch-Style Retreat on Over 8 Acres in Frederick County, VAWelcome to your private oasis in the heart of Frederick County! Nestled on over 8 partially wooded acres along peaceful Light Road, this beautifully maintained ranch-style home (with a heated in-ground swimming pool and several out-buildings)

  Jennifer Watt Century 21 Redwood Realty

  281 Light Rd, Winchester, VA 22603
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  /20

  $454,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,657 Sq Ft

  111 Yurok Ct, Winchester, VA 22602

  The Cabral offers 1,657 square feet of thoughtfully designed living space, featuring 3 spacious bedrooms, 2.5 bathrooms, and a versatile loft area on the bedroom level—perfect for a home office, playroom, or additional lounge space. Enjoy the convenience of a 2-car garage and modern finishes throughout. This home is move-in ready and comes with added perks including a washer and dryer,

  Brooks Sears D R Horton Realty of Virginia LLC

  111 Yurok Ct, Winchester, VA 22602
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  /86

  $685,000

  • 4 Beds
  • 3 Baths
  • 3,442 Sq Ft

  121 Sweetbriar Ln, Winchester, VA 22603

  "Private haven Rancher" on 13 plus acres with 4 Bedrooms and 3 full baths. Hardwood floors throughout home. See-thru Fireplace between Dining room and Living room. Recent upgraded kitchen with new flooring ,counter tops and fresh paint. Owners' Suite has bathroom w/whirlpool tub, separate shower, double sinks and French door access to the rear deck. Finished basement with full bath, bedroom,

  Andrew Hensley Samson Properties

  121 Sweetbriar Ln, Winchester, VA 22603
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  /72

  $695,000

  • 5 Beds
  • 4 Baths
  • 4,387 Sq Ft

  3949 N Frederick Pike, Winchester, VA 22603

  You will feel the peace and harmony the moment you come up the drive, this is your new home place. Almost 4 unrestricted acres for you to spread your wings. The sweet spots here will truly tug at your heart, the hammock area for lazy day reading, the fire pit with the most incredible mountain views in the fall and winter months, The four wheeler trails begging for fun and memories!! The

  Kristen Kerns Roberts Realty Group, LLC

  3949 N Frederick Pike, Winchester, VA 22603
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  /52

  $564,900

  • 4 Beds
  • 2.5 Baths
  • 2,192 Sq Ft

  109 Murphy Ct, Winchester, VA 22602

  Charming Brick 4-Bedroom Rancher in Sought-After Sovereign Village – Winchester, VAWelcome to your new home in the desirable Sovereign Village neighborhood! This beautifully maintained detached ranch-style home is nestled on a large cul-de-sac lot, offering privacy, space, and comfort both inside and out.Featuring 4 spacious bedrooms, 2 full baths, and 1 half bath, this home boasts a

  Kathrin Donovan Keller Williams Realty

  109 Murphy Ct, Winchester, VA 22602
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  /79

  $675,000

  • 4 Beds
  • 2.5 Baths
  • 2,833 Sq Ft

  283 Huntersridge Rd, Winchester, VA 22602

  The One You've Been Waiting For: 283 Huntersridge Rd – Luxury, Space, Pool & NO HOA!Stop your search! Tucked away in sought-after Oakdale Crossing, this remarkable 4-bedroom, 2.5-bathroom Colonial delivers pure luxury – all without the burden of an HOA! This isn't just a house; it's the home you've been dreaming of, packed with features that defy its price point.Imagine cooking in

  George Hockaday-Bey All Service Real Estate

  283 Huntersridge Rd, Winchester, VA 22602
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  /50

  $499,900

  • 4 Beds
  • 2.5 Baths
  • 2,884 Sq Ft

  119 Artillery Rd, Winchester, VA 22602

  Multiple offers received, seller will review offers Monday evening 6PM.Warm and Welcoming 4-Bedroom Home with Scenic Backyard and Modern UpgradesNestled on a cul de sac with mature trees and tranquil pastoral views, this lovingly maintained 4-bedroom, 2.5-bathroom home blends modern convenience with timeless comfort. Located just minutes from Route 7 and I-81, it offers easy

  Steve Bingham Realty ONE Group Capital

  119 Artillery Rd, Winchester, VA 22602
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  /78

  $689,900

  • 5 Beds
  • 4 Baths
  • 4,037 Sq Ft

  114 Renee Ln, Winchester, VA 22602

  Welcome to 114 Renee Lane – Where Elegance Meets Everyday ComfortThis beautifully appointed home offers the perfect blend of space, sophistication, and modern convenience. Boasting 5 bedrooms and 4 full bathrooms, including a main-level bedroom and full bath ideal for guests or multi-generational living, this residence is designed to accommodate today’s lifestyles.Step inside to

  Laura White ERA Oakcrest Realty, Inc.

  114 Renee Ln, Winchester, VA 22602
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  /41

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft

  327 Bryarly Rd, Winchester, VA 22603

  Charming Countryside Cape Cod on a Meticulously Maintained 1.25 acres! Welcome to 327 Bryarly Drive, Winchester, VA 22603 – a beautifully updated Cape Cod-style home nestled on a serene and private 1.25 Acre lot. Originally built in 1941, this residence exudes countryside charm and character, while offering numerous modern upgrades.Step inside to discover 3 spacious bedrooms and 2 full baths,

  Lisa Behr Coldwell Banker Premier

  327 Bryarly Rd, Winchester, VA 22603
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  /56

  $625,000

  • 4 Beds
  • 3.5 Baths
  • 2,581 Sq Ft

  1080 Old Bethel Church Rd, Winchester, VA 22603

  Turnkey Homestead on 5+ Acres | Updated 4BR Home with Farm InfrastructureWelcome to this versatile and well-maintained property located in the pastoral countryside of Frederick County, VA. Situated on 5.07 acres, this 4-bedroom, 3.5-bath home offers modern updates, flexible living spaces, and a fully functional homestead setup—ideal for those seeking rural charm with commuter

  Samantha Armel EXP Realty, LLC

  1080 Old Bethel Church Rd, Winchester, VA 22603
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  /49

  $499,870

  • 5 Beds
  • 3 Baths
  • 3,116 Sq Ft

  110 Carter Place, Winchester, VA 22602

  Extensive Renovations: The home has been fully renovated in 2025, including updates to kitchen, bathrooms, flooring, and fresh paint throughout. Designed to accommodate two families comfortably, featuring large rooms that are flooded with natural light like the entire house. The lower level is equipped with wheelchair-accessible features, enhancing mobility and convenience. Ideal for

  Rodrigo Cruz Long & Foster Real Estate, Inc.

  110 Carter Place, Winchester, VA 22602
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  /48

  $574,900

  • 4 Beds
  • 3.5 Baths
  • 2,602 Sq Ft

  1629 Pondview Dr, Winchester, VA 22601

  Discover tranquility and spacious living in this exceptional 4-bedroom, 3.5-bath home, with a main-level primary suite, ideally situated on one half of an acre backing to picturesque trees and wide-open fields. From the moment you step inside, you'll appreciate the meticulously maintained interior and inviting open floor plan. The living room features a cathedral ceiling and a cozy gas fireplace,

  Kerry & Ed Stinson Berkshire Hathaway HomeServices PenFed Realty

  1629 Pondview Dr, Winchester, VA 22601
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  /32

  $499,900

  • 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 ready conditionThis home offers the perfect blend

  Cherish Green Coldwell Banker Elite

  201 Parkway St, Winchester, VA 22601
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  /26

  $499,900

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

  811 Berryville Ave, Winchester, VA 22601

  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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  /43

  $559,000

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

  1420 Fishel Rd, Winchester, VA 22602

  Tucked away on over 2.5 wooded acres, this beautifully updated home offers the ease of one-level living with exceptional space and privacy. Inside, you’ll find 3 bedrooms, 2 updated full baths, brand-new luxury vinyl plank flooring, and fresh paint throughout. The light-filled eat-in kitchen features an island and stainless steel appliances, opening to a spacious layout that includes a large

  Katherine (Kat) Wetzel Century 21 Redwood Realty

  1420 Fishel Rd, Winchester, VA 22602
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  /40

  $530,000

  • 5 Beds
  • 3 Baths
  • 2,489 Sq Ft

  116 Lenore Ln, Winchester, VA 22602

  Stunning home in the heart of Raven Oaks, this residence is a testament to both beauty and functionality. Thoughtful upgrades and features enhance the overall appeal and convenience of this beautiful home. The kitchen, the heart of this home, has been upgraded to perfection, there is also a bedroom and one full bathroom on the main level too and a gourmet kitchen with a large center island. On

  Michael Putnam RE/MAX Executives

  116 Lenore Ln, Winchester, VA 22602
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  /28

  $499,000

  • 6 Beds
  • 3 Baths
  • 2,736 Sq Ft

  386 Round Hill Rd, Winchester, VA 22602

  ATTENTION INVESTORS!! *** You will want to check out this fantastic opportunity - with a history of POSITIVE CASH FLOW these two ADJACENT PROPERTIES on a combined total of 1.91-acres in Winchester, just minutes from Valley Health Campus, shopping, restaurants and Rt. 37, may be what you are looking for! *** These two parcels are to be sold TOGETHER; they are not offered separately, and all for

  Bridget Aikens Colony Realty

  386 Round Hill Rd, Winchester, VA 22602
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  /53

  $490,000

  • 4 Beds
  • 2 Baths
  • 2,012 Sq Ft

  669 Dicks Hollow Rd, Winchester, VA 22603

  Welcome to this spacious farmhouse on FIVE acres! NEW TWO ZONE HEAT AND AC BEING INSTALLED ON TUESDAY THE 17TH! NEW hot water heater! NEWER windows throughout. Metal roof - large detached two car garage with large work area. Pole barn and garden shed! Apple trees, peach tree - 15 minutes to town! All windows are newer as well. WOOD FLOORS! LARGE wrap around deck! Hiking trails on

  Barbera Clausen EXP Realty, LLC

  669 Dicks Hollow Rd, Winchester, VA 22603
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  /56

  $569,900

  • 4 Beds
  • 3 Baths
  • 3,998 Sq Ft

  419 Westside Station Dr, Winchester, VA 22601

  “Classic and Contemporary” - Welcome to this beautifully maintained contemporary home nestled in one of Winchester's most hidden but premium neighborhoods. Offering nearly 4,000 square feet of finished living space across three thoughtfully designed levels, this 4-bedroom, 3-bath residence combines stylish updates with unique architectural details. Step inside to discover a warm and inviting

  Mark Francis ICON Real Estate, LLC

  419 Westside Station Dr, Winchester, VA 22601
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  /57

  $530,000

  • 5 Beds
  • 3.5 Baths
  • 2,854 Sq Ft

  105 Fairfield Dr, Winchester, VA 22602

  Welcome to this generously sized 5-bedroom, 3.5-bathroom home located in the sought-after Oakdale Crossing community of Winchester, VA. This property offers a fantastic opportunity to personalize and update to your taste.Inside, you’ll find a bright, flowing floor plan featuring a large living room, formal dining area, and a spacious kitchen with plenty of cabinetry. The upstairs layout includes

  Ruby Miller Samson Properties

  105 Fairfield Dr, Winchester, VA 22602
• 

  

  /40

  $559,000

  • 4 Beds
  • 3.5 Baths
  • 2,884 Sq Ft

  111 Sovereign Ct, Winchester, VA 22602

  Welcome home to this beautifully designed 4-bedroom, 3.5-bathroom residence in the charming community of Freedom Manor! This home offers the perfect blend of style, comfort, and energy efficiency, all in a prime location near shopping and conveniences.Step inside to find an inviting eat-in kitchen featuring sleek quartz countertops, a spacious island, and a gas range—perfect for cooking and

  Natalie Dalecky ERA Oakcrest Realty, Inc.

  111 Sovereign Ct, Winchester, VA 22602
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  /41

  $540,000

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  129 Jalapa Trail, Winchester, VA 22602

  Brand new everything, Roof, appliances, water treatment , bathrooms, deck, Sunroom, flooring Motivated Seller The perfect retreat for everyone, Welcome to your dream home in the heart of the Virginia Mountains , yet only 7 miles to the new Medical Center in Winchester. The property has access to the community lake, picnic grounds, play ground and loads of nature trails for hiking and nature

  Leslie Woods-Hulse Century 21 Redwood Realty

  129 Jalapa Trail, Winchester, VA 22602
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  /36

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,328 Sq Ft

  224 Lauck Dr, Winchester, VA 22603

  Custom Home in Historic Star Fort: Timeless Charm Meets modern Comfort for Discerning Buyers.This impeccably designed 3-bedroom, 2.5-bath home is a harmonious blend of classic elegance and contemporary convenience. Boasting cherry wood flooring throughout the main living areas, high-quality tile in the kitchen and bathrooms, and carpeted bedrooms, this home is as stylish as it is practical. Be

  Gidget Smallwood Coldwell Banker Premier

  224 Lauck Dr, Winchester, VA 22603
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  /61

  $579,000

  • 4 Beds
  • 2.5 Baths
  • 3,263 Sq Ft

  1380 Magruder Ct, Winchester, VA 22601

  PRICE REDUCTION!!!Rare opportunity in a most desirable location...walk to the Museum of the Shenandoah Valley and Winchester Medical Center!! Close to Old Town Winchester and other shopping. Well maintained colonial style home in highly sought after Downs at Meadow Branch community. Bright and airy with lots of natural light, 4 bedroom, 2.5 baths with incredibly large primary suite. Several

  Stuart Wolk ERA Oakcrest Realty, Inc.

  1380 Magruder Ct, Winchester, VA 22601
• 

  

  /51

  $574,900

  • 4 Beds
  • 2.5 Baths
  • 3,036 Sq Ft

  3336 Hunting Ridge Rd, Winchester, VA 22603

  IMPROVED PRICE! Come home to this beautifully designed POOL HOUSE featuring 4-bedrooms, 3-baths, just in time for summer! This modern home is perfect for those who appreciate privacy and natural beauty, while situated on a gorgeous 5-acre lot. With spacious living areas, sleek finishes, and an open floor plan, this home is the epitome of contemporary modern living.The well-lit kitchen is a true

  Karl Achstetter Keller Williams Realty

  3336 Hunting Ridge Rd, Winchester, VA 22603
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  /55

  $539,900

  • 6 Beds
  • 4.5 Baths
  • 3,612 Sq Ft

  531 Washout Ln, Winchester, VA 22603

  BONUS BONUS BONUS The Seller is very motivated and is offering $15,000.00 towards repairs and also offering 3% towards closing cost. The garage has been converted into a private living area. Great for the out of town family that need their privacy or the young adult that may want their independence or maybe you would like to have a private living area for your in-laws. So no matter the reason

  Janet Broyles CENTURY 21 New Millennium

  531 Washout Ln, Winchester, VA 22603
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  /26

  $535,000

  • 3 Beds
  • 3 Baths
  • 1,809 Sq Ft

  257 Jefferson St, Winchester, VA 22601

  Jonathan Minerick Homecoin.com

  257 Jefferson St, Winchester, VA 22601
• 

  

  /43

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  1000 Hickory Trail, Winchester, VA 22602

  Hickory Trail... WHAT A FIND!!! This home shows nicely and simply needs a little TLC, whether an investor, a DIY Enthusiast, or whatever your goals may be, this home has so many possibilities without a ton of work, so much so, there's simply not enough space to list them all! Inside you'll find spacious living, high ceilings in the living room and dine in kitchen, sizeable bedrooms and lovely

  Nicole Lewis Coldwell Banker Premier

  1000 Hickory Trail, Winchester, VA 22602
• 

  

  /40

  $465,000

  • 3 Beds
  • 2 Baths
  • 2,934 Sq Ft

  474 Cedar Grove Rd, Winchester, VA 22603

  This beautifully maintained 3-bedroom, 2-bathroom ranch offers the perfect blend of style, space, and serenity. Situated on a spacious 1.23-acre lot, this home features an inviting open floor plan with luxury vinyl plank (LVP) flooring throughout the main living areas. The kitchen boasts elegant quartz countertops, a stylish backsplash, and plenty of cabinet space for the home chef. Soaring

  Jena Magnanelli MarketPlace REALTY

  474 Cedar Grove Rd, Winchester, VA 22603

Showing Results 1 - 40, Page 1 of 5

Why Live in Winchester

Winchester, located in the Shenandoah Valley, is a rapidly growing town known for its apple-themed events and historic downtown. The area attracts residents from neighboring Loudoun County and Washington D.C. due to its more affordable housing and small-town atmosphere. Winchester's economy is driven by health care, retail, and manufacturing, with Valley Health being a major employer. Commuters often use Interstate 81 and U.S. Route 50 for the 75-mile trip to Northern Virginia and D.C., while Winchester Transit provides local bus services. The Dulles International Airport is 50 miles away. The town experiences humid summers and mild winters, with occasional minor flooding due to heavy rainfall. Housing options include historic homes with Craftsman or Colonial Revival designs, typically priced between $400,000 and $600,000. Winchester City Public Schools are highly rated, and Shenandoah University offers strong liberal arts and performing arts programs. The Shenandoah Apple Blossom Festival is a major annual event, drawing 250,000 visitors for parades and festivities. Residents enjoy shopping at the Apple Blossom Mall and Old Town Winchester, as well as local farmers markets. Outdoor attractions include Jim Barnett Park, the Museum of the Shenandoah Valley, and nearby Shenandoah River State Park. Historical sites such as George Washington's Office and the Patsy Cline Historic House add to Winchester's rich heritage. Winchester remains a popular choice for those seeking a blend of affordability, history, and community.

Learn more about living in Winchester

Home Trends in Winchester, VA

On average, homes in Winchester, VA sell after 41 days on the market compared to the national average of 50 days. The median sale price for homes in Winchester, VA over the last 12 months is $404,375, up 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$404,375

Median Single Family Sale Price

$425,000

Median Townhouse Sale Price

$391,426

Median 2 Bedroom Sale Price

$245,000

Median 1 Bedroom Sale Price

$225,000

Average Price Per Sq Ft

$208

Number of Homes for Sale

247

Last 12 months Home Sales

1,008

Months of Supply

2.90

Median List Price

$415,000

Median Change From 1st List Price

0%

Median Home Sale Price YoY Change

2%