Winchester, VA Homes

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  /46

  $899,000

  • 4 Beds
  • 2.5 Baths
  • 2,859 Sq Ft

  247 Mcguire Rd, Winchester, VA 22603

  Tucked away on a private 2.7-acre wooded lot, this stunning all-brick colonial was fully renovated from top to bottom last year. Inside, 3/4" solid ash, 5"wide herringbone flooring flows throughout, accented by designer lighting, crown molding, and elegant chair rail trim. The chef’s kitchen is a true showstopper—featuring a massive island, striking white and gold appliances, and custom finishes.

  

  Lori Bales

  Keller Williams Realty

  (540) 701-5541

  247 Mcguire Rd, Winchester, VA 22603
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  Explore Winchester

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  /12

  $2,350 per month

  • 3 Beds
  • 2.5 Baths
  • 2,106 Sq Ft
  • Townhouse for Rent

  125 Brockham Ct, Winchester, VA 22602

  This home has ample space and an open layout. The kitchen features granite countertops, a large peninsula with a breakfast bar, double ovens, and a stainless steel refrigerator with French doors. The living room features a gas fireplace. The home features a master bedroom with a walk-in closet and en suite bathroom with a whirlpool tub, and two additional bedrooms. The ground floor features a

  

  Diego Gonzales

  Inmobiliaria De Las Casas LLC

  (540) 501-7067

  125 Brockham Ct, Winchester, VA 22602
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  /33

  $277,000 Sold Sep 17, 2025

  • 2,058 Sq Ft
  • $135/SF
  • 15 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1910

  566 N Loudoun St, Winchester, VA 22601

  Welcome to 566 N Loudoun Street, a spacious 4-bedroom, 2-full-bath home offering a fantastic blend of historic appeal and modern potential in Winchester, VA. This property boasts classic hardwood floors throughout and valuable off-street parking, a significant benefit in this area. Enjoy the outdoors with a large covered front porch perfect for relaxing, and a private patio in the rear, all

  Dan Whitacre Colony Realty

  566 N Loudoun St, Winchester, VA 22601
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  /39

  Est $402,924 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 1,344 Sq Ft

  1613 Whittier Ave, Winchester, VA 22601

  1613 Whittier Ave, Winchester, VA 22601
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  /46

  $415,000 Under Contract

  • 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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  /11

  $1,700 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  44 S Loudoun St Unit 12, Winchester, VA 22601

  Discover the pinnacle of urban living in this charming 1-bedroom, 1-bathroom apartment located in the heart of the historic Winchester downtown walking mall. This comfortably spacious apartment merges the charm of its historic surroundings with the convenience of modern amenities, creating an exceptional rental choice. Perfectly positioned on the bustling Winchester walking mall, the apartment is

  

  Brock Harris

  Samson Properties

  (540) 584-1912

  44 S Loudoun St Unit 12, Winchester, VA 22601
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  /61

  $615,000 Sold Sep 17, 2025

  • 3,262 Sq Ft
  • $189/SF
  • 3 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2004

  215 Darby Dr, Winchester, VA 22602

  Nestled on a cul-de-sac in a very desirable neighborhood with prime location near Winchester Country Club & Jim Barnett Park, this well-loved and meticulously cared-for 4-bedroom, 2 full and 2 half-bath home offers exceptional space and comfort across three finished levels. The inviting front porch sets the tone for warmth and relaxation and offers an inviting welcome home. Inside, the spacious

  Laura White ERA Oakcrest Realty, Inc.

  215 Darby Dr, Winchester, VA 22602
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  /34

  Est $366,974 Not Listed For Sale

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

  105 Price Dr, Winchester, VA 22602

  105 Price Dr, Winchester, VA 22602
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  /49

  $422,000

  • 4 Beds
  • 3.5 Baths
  • 2,783 Sq Ft

  500 Quail Dr, Winchester, VA 22602

  500 Quail Dr, Winchester, VA – Beautifully Maintained 4 BR Home in Scenic VirginiaNestled in one of the most picturesque areas of Virginia, this spacious 4-bedroom, 3.5-bathroom home offers the perfect blend of charm, comfort, and convenience. Located just minutes from Interstate 81, you’ll enjoy easy access to commuting routes while still savoring the peace and beauty of your

  

  Dunia Woodward

  Impact Real Estate, LLC

  (540) 274-2342

  500 Quail Dr, Winchester, VA 22602
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  /12

  $2,400 per month

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  21 S Stewart St Unit 4, Winchester, VA 22601

  Charming Remodeled 2-Bedroom Apartment Near Old Town Winchester!Enjoy the perfect mix of comfort and convenience in this beautifully remodeled 2 bedroom, 2 bathroom apartment located just steps from historic Old Town Winchester. This spacious unit features modern updates, in-unit laundry, and a fully fenced private yard—ideal for relaxing or entertaining. You'll also love the generous storage

  

  Frank Armstrong, IV

  Colony Realty

  (540) 781-1596

  21 S Stewart St Unit 4, Winchester, VA 22601
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  /34

  $355,000 Sold Sep 17, 2025

  • 1,530 Sq Ft
  • $232/SF
  • 72 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1971

  12 Montague Cir, Winchester, VA 22601

  Welcome to 12 Montague Circle — a recently updated 3-bedroom, 1.5-bath home tucked away in a quiet cul-de-sac in downtown Winchester. Enjoy the best of both worlds with a peaceful, private setting and immediate access to restaurants, shops, grocery stores, and all the charm the city has to offer. This recently renovated gem features a new roof and HVAC system, durable and modern LVP flooring, and

  Jon Fleming Weichert Realtors - Blue Ribbon

  12 Montague Cir, Winchester, VA 22601
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  /17

  Est $283,682 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,944 Sq Ft

  410 Emily Ln, Winchester, VA 22602

  410 Emily Ln, Winchester, VA 22602
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  /40

  $365,000

  • 4 Beds
  • 2.5 Baths
  • 2,124 Sq Ft

  306 Mountain Falls Blvd, Winchester, VA 22602

  Welcome to 306 Mountain Falls Blvd – Your Peaceful Mountain Retreat Awaits!Nestled in the scenic beauty of the Mountain Falls Park community, this charming home offers the perfect blend of privacy, comfort, and modern living. Set on a spacious lot surrounded by trees and nature, you'll enjoy the serenity of country living with the convenience of being just a short drive to downtown Winchester

  

  Dunia Woodward

  Impact Real Estate, LLC

  (540) 730-1769

  306 Mountain Falls Blvd, Winchester, VA 22602
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  /8

  $1,150 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  2259 Papermill Rd Unit 4, Winchester, VA 22601

  This lower level apartment is an end unit. 1 bedroom,1 bath apartment is in a great location close to shopping and restaurants. NO Smoking, NO pets, NO Vaping. $30 application fee to cover credit and background check. Landlord is looking for around 700 credit score.

  

  Frank Armstrong, IV

  Colony Realty

  (540) 701-4871

  2259 Papermill Rd Unit 4, Winchester, VA 22601
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  /74

  $540,000 Sold Sep 16, 2025

  • 3,360 Sq Ft
  • $161/SF
  • 4 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2009

  292 Fortress Dr, Winchester, VA 22603

  Welcome to 292 Fortress Drive, where pride of ownership shines throughout! This stunning home has been beautifully updated and shows in perfect condition. The newly finished basement adds incredible value, featuring a 5th bedroom and full bath—ideal for guests, extended family, or a private office. The main level offers a modern kitchen with granite countertops, stylish cabinetry, and plenty of

  Deborah Matthews ERA Oakcrest Realty, Inc.

  292 Fortress Dr, Winchester, VA 22603
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  /37

  Est $429,898 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,052 Sq Ft

  222 E Piccadilly St, Winchester, VA 22601

  222 E Piccadilly St, Winchester, VA 22601
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  /12

  $279,900

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  2718 Welltown Rd, Winchester, VA 22603

  Beautiful and buildable lots on Welltown Road. Build your dream house and an extended family suite/ guest house. Build two, live in one, sell one! There are so many option on this unrestricted parcel. The mobile home on the property has electric, well and septic. The mobile home is not where the value is and is a tear down. The second parcel has been perc previously and is suitable for

  

  Tracey Scott

  Path Realty

  (540) 453-8745

  2718 Welltown Rd, Winchester, VA 22603
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  /74

  $1,700 - $2,400 per month

  The Local

  1 - 4 Beds

  230 Spring St, Winchester, VA 22601

  Modern designs, elegant finishes, and the most desirable amenities await you at the areas newest apartment home living destination, the Local. Our Winchester apartments come in one, two, three, and four-bedroom floorplans, each featuring spacious and adaptable layouts. Various interior extras adorn them including an open floorplan concept, walk-in closets, in-unit washers/dryers, and more. As a

  230 Spring St, Winchester, VA 22601
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  /36

  $385,000 Sold Sep 16, 2025

  • 1,664 Sq Ft
  • $231/SF
  • 37 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1998

  111 Old Dominion Dr, Winchester, VA 22603

  JUST REDUCED!!!Welcome to 111 Old Dominion Dr — a beautifully maintained colonial nestled in a desirable Winchester neighborhood. This 3-bedroom, 2.5-bath detached home offers 1,664 square feet of bright, open living space featuring crown molding, recessed lighting, and modern finishes throughout (roof was changed in 2021, AC changed in 2021, water heater in 2021). The updated kitchen boasts

  Carolina Mosquera Weichert, REALTORS

  111 Old Dominion Dr, Winchester, VA 22603
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  /14

  Not Listed For Sale

  0 Susquehanna Trail, Winchester, VA 22602

  0 Susquehanna Trail, Winchester, VA 22602
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  /9

  $225,000

  • Land
  • 5.99 Acres
  • $37,563 per Acre

  Lot 3 Cedar Creek Grade, Winchester, VA

  Beautiful lot in a small neighborhood on the very desirable west side of Winchester off Cedar Creek Grade! Lot is already perked for an alternative septic system. This opportunity doesn’t come along often! Rolling hills with beautiful surroundings and views. The location is less than 10 minutes to grocery stores, downtown Winchester, or Winchester Medical Center. It’s also located within 2

  

  Lori Bales

  Keller Williams Realty

  (540) 974-1542

  Lot 3 Cedar Creek Grade, Winchester, VA
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  /5

  $1,050 per month

  • 1 Bath
  • 2,314 Sq Ft
  • Condo for Rent

  424 N Loudoun St Unit 3, Winchester, VA 22601

  Furnished efficiency NOW available! 3 month minimum rental. No smoking and no animals please. Water/sewer/trash included. Electric allowance of $100/mo, VAR or NVAR application is fine w/ $50 app fee paid by cash or money order or you may apply online thru website.

  Mandie Gladwell OliveTree Property Group, LLC

  424 N Loudoun St Unit 3, Winchester, VA 22601
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  /70

  $661,000 Sold Sep 16, 2025

  • 4,395 Sq Ft
  • $150/SF
  • 144 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2018

  113 Pangborne Ct, Winchester, VA 22602

  Back on the market at no fault of the seller and priced to sell! With nearly 4,400 finished square feet, this home can accommodate the needs of any buyer. Sitting on a quiet cul de sac on the desirable east side of Winchester, the location is ideal for commuters to NOVA as well as provides easy access to I-81. The spacious main floor offers a living room, formal dining room, study, family room,

  Stephanie Ryall Realty ONE Group Old Towne

  113 Pangborne Ct, Winchester, VA 22602
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  /20

  Est $446,543 Not Listed For Sale

  • 2 Beds
  • 4 Baths
  • 2,160 Sq Ft

  206 N Kent St, Winchester, VA 22601

  206 N Kent St, Winchester, VA 22601
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  /57

  $449,900

  • 4 Beds
  • 3.5 Baths
  • 1,676 Sq Ft

  125 Alliance Ct, Winchester, VA 22602

  Welcome to this beautifully maintained home in the highly desirable Freedom Manor subdivision in Winchester, VA—ideally located just minutes from shopping, dining, and everyday conveniences. Offering a perfect blend of comfort, functionality, and location, this property is ready to impress.The main level features durable and stylish luxury vinyl plank (LVP) flooring throughout. The living

  

  Rhonda Shade

  ERA Oakcrest Realty, Inc.

  (540) 619-5307

  125 Alliance Ct, Winchester, VA 22602
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  /70

  $2,116 - $2,690 per month

  The Lofts at Jubal Square

  1 - 3 Beds

  1864 Old Jube Square, Winchester, VA 22601

  Weve got it all at the Lofts at Jubal Square, the newest addition to the charming andhistoric Winchester cityscape. We offer a total commitment to better living, boasting largeapartments with loft and garage options, as well as amenities ideal for all those seeking anexceptional apartment lifestyle. Discover the Lofts at Jubal Square and discover what itmeans to live the good life.

  1864 Old Jube Square, Winchester, VA 22601
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  /36

  $400,000 Sold Sep 15, 2025

  • 1,664 Sq Ft
  • $240/SF
  • 42 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2001

  100 Candlewick Dr, Winchester, VA 22602

  “Cottage on Candlewick” - Welcome to easy, one-level living in the highly sought-after Cross Creek Village, a 55+ community designed for comfort, convenience, and connection. This beautifully maintained 2-bedroom, 2-bath home offers over 1,600 square feet of thoughtfully designed living space—all on one level for maximum accessibility.Perfectly situated near the front of the neighborhood

  Mark Francis ICON Real Estate, LLC

  100 Candlewick Dr, Winchester, VA 22602
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  /43

  Est $641,775 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,729 Sq Ft

  405 Lynnehaven Dr, Winchester, VA 22602

  405 Lynnehaven Dr, Winchester, VA 22602
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  /54

  $489,000

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

  101 Delaware Trail, Winchester, VA 22602

  Huge Price Adjustment! Motivated Sellers. Price Reduced! Be in before the leaves start to change! You must see this home to believe it. Fabulous remodel using the finest materials. Winchester VA. Outdoor activities are everywhere you turn at this completely renovated home in Winchester. Hiking, swimming, biking, and kayaking are all close by. As you sit on the beautiful deck, you can listen to

  

  Kimberly Pace

  EXP Realty, LLC

  (540) 240-9877

  101 Delaware Trail, Winchester, VA 22602
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  /15

  $1,100 per month

  • 2 Beds
  • 1.5 Baths
  • 1,106 Sq Ft
  • Townhouse for Rent

  512 Allston Cir, Winchester, VA 22601

  NO PETS. Two-bedroom 1.5 half bath townhouse, located minutes from restaurants and shopping. Requirements to qualify: 1) Minimum annual household income $49k, 2) Good credit, 3) Good landlord reference. $47 application fee per applicant over 18yrs old.

  Courtney Spaid Crum Realty, Inc.

  512 Allston Cir, Winchester, VA 22601
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  /52

  $585,000 Sold Sep 15, 2025

  • 2,268 Sq Ft
  • $258/SF
  • 28 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1968

  224 Vine Ln, Winchester, VA 22602

  Welcome to 224 Vine Lane – A Rare Gem in Winchester!Situated on a beautifully landscaped lot with fantastic curb appeal, this updated Cape Cod offers timeless charm, spacious living, and exciting potential with an additional building lot included in the sale!Step inside to discover large, light-filled rooms, a functional layout, and tasteful updates throughout. The main level boasts

  Tracie Clawson ERA Oakcrest Realty, Inc.

  224 Vine Ln, Winchester, VA 22602
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  /6

  Not Listed For Sale

  • Studio
  • 1,710 Sq Ft

  13 E North Ave, Winchester, VA 22601

  13 E North Ave, Winchester, VA 22601
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  /99

  $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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  /22

  $1,749 - $2,489 per month

  Meadow Branch Luxury Apartments

  1 - 3 Beds

  424 Ridgewood Ln, Winchester, VA 22601

  Welcome to Meadow Branch, where luxury and convenience are standard. Our community offers beautiful 1,2 and 3 bedroom apartment homes. Community means convenience and at Meadow Branch, everything you need is nearby. We are conveniently located adjacent to Winchester Medical Center and 2 miles from Old Town Winchester.

  424 Ridgewood Ln, Winchester, VA 22601
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  /2

  $176,000 Sold Sep 12, 2025

  • 1,536 Sq Ft
  • $115/SF
  • 6 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1910

  311 National Ave, Winchester, VA 22601

  Colonial with separate lower and upper living units located blocks from downtown Winchester & the local library. Upper level is a 1 Bed/1 Bath with living room & kitchen and laundry hook-ups. Lower level is a 1 Bed/1 Bath with living room & kitchen and no laundry hook-ups. AS IS property.Access property through Jolley Lane (rear of property) parking in back. DO not disturb tenant

  Sheila Pack RE/MAX Roots

  311 National Ave, Winchester, VA 22601
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  /60

  Est $413,422 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,300 Sq Ft

  152 Solara Dr, Winchester, VA 22602

  152 Solara Dr, Winchester, VA 22602
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  /10

  $58,900

  • Land
  • 0.69 Acre
  • $85,362 per Acre

  Lots 4 & 5 Glen Ridge Rd, Winchester, VA 22602

  Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for someone who wants to be in a community, but still have

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 402-9785

  Lots 4 & 5 Glen Ridge Rd, Winchester, VA 22602
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  /21

  $2,000 per month

  • 3 Beds
  • 2 Baths
  • 1,826 Sq Ft
  • House for Rent

  200 Canyon Rd, Winchester, VA 22602

  A commuters dream easy access to RT 7 and I 81 Enjoy the comfort and convenience of all on one level living Fresh interior paint , newer carpet in bedrooms Spacious kitchen w eat in area Easy access to back yard w deck for cookouts and relaxing Living room w lots of natural light Primary bedroom w walk in closet en suite bath w double vanities Owner is requesting

  Carolyn Waymack Crum Realty, Inc.

  200 Canyon Rd, Winchester, VA 22602
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  /48

  $500,000 Sold Sep 12, 2025

  • 2,285 Sq Ft
  • $219/SF
  • 5 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1946

  257 Jefferson St, Winchester, VA 22601

  Charming Craftsman in West Whitlock Avenue – Walk to John Handley!Welcome to 257 Jefferson Street, a beautifully maintained 3-bedroom, 1 full and 2 half bath Craftsman-style home located in the highly desirable West Whitlock Avenue subdivision. This 2,285 sq ft gem offers timeless charm, modern updates, and a prime location within walking distance to the prestigious John Handley High

  Kathrin Donovan Keller Williams Realty

  257 Jefferson St, Winchester, VA 22601
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  /27

  Est $382,907 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  427 Washout Ln, Winchester, VA 22603

  427 Washout Ln, Winchester, VA 22603

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