Winchester, VA Homes 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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  /42

  $349,000

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

  107 E Monmouth St, Winchester, VA 22601

  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 feel right at

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 590-5989

  107 E Monmouth St, Winchester, VA 22601
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  /45

  $500,000 Open Sun 12PM - 2PM

  • 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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  /104

  $869,500

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

  1517 Brookdale Ct, Winchester, VA 22601

  Welcome to this stunning and spacious brick Colonial, perfectly situated on one of the best lots in Morlyn Hills, nestled on a quiet cul-de-sac and overlooking a 45-acre protected wetland preserve. Impeccably maintained and offering over 6,500 + of finished square feet of elegant living space! This home features 4 bedrooms, 4.5 baths, and an impressive array of upgrades throughout.From the

  

  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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  /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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  /49

  $280,000

  • Land
  • 25 Acres
  • $11,129 per Acre

  Mockingbird Lane Lot Unit WP007A, Winchester, VA 22603

  Own a piece of the beautiful Siler Heights community in Cross Junction. Located just minutes northwest of Winchester near Lake Holiday. Access is secured via extensive road frontage on Mockingbird Lane. Features a fully functional hunting cabin wired for a generator hook up with a wood stove and propane used for heating and cooking. The cabin has an open layout and separate sleeping quarters in

  Chad Pangle

  Mockingbird Lane Lot Unit WP007A, Winchester, VA 22603
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  /50

  $345,000

  • Land
  • 40 Acres
  • $8,582 per Acre

  Mockingbird Lane Lot Unit WP008, Winchester, VA 22603

  Own a piece of the beautiful Siler Heights community in Cross Junction. Located just minutes northwest of Winchester near Lake Holiday. Access is secured via extensive road frontage on Mockingbird Lane. Features a fully functional hunting cabin with a wood stove and propane used for heating and cooking. The cabin has an open layout and separate sleeping quarters via a loft. Experience exciting

  Chad Pangle

  Mockingbird Lane Lot Unit WP008, Winchester, VA 22603
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  /26

  $245,000

  • Land
  • 23 Acres
  • $10,452 per Acre

  Mockingbird Lane Lot Unit WP007, Winchester, VA 22603

  Own a piece of the beautiful Siler Heights community in Cross Junction. Located just minutes northwest of Winchester near Lake Holiday. Access is secured via extensive road frontage on Mockingbird Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey and many small game species. There are potential building sites located throughout the

  Chad Pangle

  Mockingbird Lane Lot Unit WP007, Winchester, VA 22603
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  /31

  $125,000

  • Land
  • 23 Acres
  • $5,383 per Acre

  0 Bear Trail Unit LotWP001 22365692, Winchester, VA 22602

  Idyllic, mostly wooded mountaintop sanctuary made up of three parcels with many residential and recreational possibilities. It is located just a few miles west of Winchester above Shawneeland. The large parcel is part of the Great North Mountain Wilderness community. The soil work on one of the small parcels is approved for a two-bedroom septic system, and the owner has stated that at one time,

  Chad Pangle Whitetail Properties Real Estate

  0 Bear Trail Unit LotWP001 22365692, Winchester, VA 22602
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  /32

  $58,999

  • Land
  • 6 Acres
  • $10,137 per Acre

  0 Pack Horse Rd Unit LotWP00E 21685367, Winchester, VA 22603

  BRAND NEW gravel entrance, road to homesite, and survey!!!! Attractive OWNER FINANCING terms available!!! Enjoy rural living and fun on this building lot in the Valley Estates community. This land is located off of Pack Horse Road not far from the West Virginia state line. This prime wooded lot perked for a 3 bedroom septic system just recently. Access is secured via road frontage on Pack Horse

  Chad Pangle Whitetail Properties Real Estate

  0 Pack Horse Rd Unit LotWP00E 21685367, Winchester, VA 22603
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  /23

  $168,000

  • Land
  • 10 Acres
  • $16,800 per Acre

  0 Gough Rd Unit LotWP002 20612085, Winchester, VA 22602

  Enjoy rural living and fun on this building lot in the Long Ridge Estates community. This prime building lot is located off of Gough Road in the High View Manor area of the county. This parcel has a septic certification letter on record with the county health department for a four-bedroom septic system. Access is secured via a 50 ft deeded access easement, which has already been installed and

  Chad Pangle Whitetail Properties Real Estate

  0 Gough Rd Unit LotWP002 20612085, Winchester, VA 22602
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  $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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  /29

  $414,900

  • 3 Beds
  • 2.5 Baths
  • 1,962 Sq Ft

  117 Tye Ct, Winchester, VA 22602

  Modern, Move-In Ready Townhome with Premium UpgradesIdeally located just outside the bustle of Winchester with an easy commute to the DC Metro area, this 2023-built townhome offers the perfect balance of comfort, convenience, and style.Freshly and professionally painted throughout, the home features an open-concept main level with durable LVP flooring, granite countertops,

  Rick Cockrill Keller Williams Realty

  117 Tye Ct, Winchester, VA 22602
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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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  /23

  $369,900 Open Sun 12PM - 3PM

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

  116 Copeley Cir, Winchester, VA 22602

  Beautifully appointed garage townhome available now in Freedom Manor. Less than 3 years old and ideally located on one of the best lots in the neighborhood! Fantastic floor plan offering that highly desirable main level entry making this the home you want for easy living and minimal stairs. Just a few of the interior upgrades include warm luxury vinyl plank flooring spanning the entire main level

  Mike Casto Weichert, REALTORS

  116 Copeley Cir, 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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  /49

  $649,000

  • 4 Beds
  • 3 Baths
  • 3,591 Sq Ft

  101 Morgan St, Winchester, VA 22601

  Downtown Winchester - 2 blocks from the walking mall with in-law suite or lower level rental potential! From the moment you arrive, you’ll be drawn in by this home’s timeless symmetry, classic brick exterior, and welcoming front porch. Thoughtful landscaping and charming details set the stage for what’s inside. With 5 bedrooms and 3 full baths, there’s plenty of space for everyone. The

  Jeanne Mezzatesta Colony Realty

  101 Morgan St, Winchester, VA 22601
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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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  /28

  $410,000

  • 3 Beds
  • 2.5 Baths
  • 2,281 Sq Ft

  154 Solara Dr, Winchester, VA 22602

  Charming Townhome with Solar Savings in a Prime Location!Welcome to this beautifully updated townhome nestled in a highly sought-after neighborhood just minutes from Rt 7! This move-in ready home boasts paid-off solar panels, keeping your electric bills at an incredible $20/month on average—a rare and valuable find.Inside, you'll find fresh paint throughout, new luxury vinyl plank

  Kandi McKenzie Realty ONE Group Old Towne

  154 Solara Dr, Winchester, VA 22602
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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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  /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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  /47

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 1,865 Sq Ft

  336 Miller St, Winchester, VA 22601

  This beautiful cottage, nestled on the very sought after Miller St, supplies the utmost convenience for what Winchester has to offer. From walking distance to eateries and Old Town entertainment, a quick drive to supermarkets all around and Handley High School just one street away! Supplying 3 bedrooms 2 1/2 bathrooms across three levels you can appreciate the character of an older home with

  Julie Teets Long & Foster Real Estate, Inc.

  336 Miller St, 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

Showing Results 1 - 40, Page 1 of 8

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

Frequently Asked Questions

What is the average home price in Winchester, VA?

Homes for sale in Winchester, VA have an average home price of $465,277.

How many homes have sold over the last 12 months in Winchester, VA?

1,022 homes have sold in Winchester, VA over the last 12 months.

Is Winchester, VA a safe city?

In general, the safest neighborhoods in Winchester, VA with lower crime scores are Stephenson, Cross Junction and Clear Brook.

What are the most popular zip codes in Winchester, VA?

The most popular zip codes in Winchester, VA include 25414, 22630, 22602, 25428 and 25438.

What are the most popular neighborhoods in Winchester, VA?

The most popular neighborhoods in Winchester, VA with the most homes for sale are Stephenson, Cross Junction and Clear Brook.

How much do you need to make to afford a house in Winchester?

The median home price in Winchester is $417,250. If you put a 20% down payment of $83,400 and had a 30-year fixed mortgage with an interest rate of 6.77%, your estimated principal and interest payment would be $2,170 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $93K a year to afford the median home price in Winchester.

How are the schools in Winchester, VA?

Winchester, VA has highly rated public and private schools. Some of the best schools in Winchester based on Niche Grades are Mountain View Christian Academy, Sherando High School and James Wood High School. The neighborhoods in Winchester with the highest rated schools are Stephenson, Cross Junction and Clear Brook. Browse all the schools in Winchester, VA to learn more.

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 $405,000, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$405,000

Median Single Family Sale Price

$425,000

Median Townhouse Sale Price

$389,990

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

263

Last 12 months Home Sales

1,022

Months of Supply

3.10

Median List Price

$417,250

Median Change From 1st List Price

0%

Median Home Sale Price YoY Change

3%