Winchester, VA Homes

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  /25

  $279,999 Under Contract

  • 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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  /46

  $1,655 - $2,755 per month

  Stuart Hill

  1 - 3 Beds

  1981 Randolph Place, Winchester, VA 22601

  Nestled in the picturesque Shenandoah Valley in historic Winchester, Virginia, Stuart Hill Apartments combines convenience, a quality lifestyle, and warm, personalized service. Ideally situated just minutes from Historic Downtown Winchester, local shopping and dining, Shenandoah University, and the top-rated Winchester Medical Center, our community offers unparalleled access to everything you

  1981 Randolph Place, Winchester, VA 22601
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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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  /49

  Est $633,401 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,722 Sq Ft

  117 Thompson Ct, Winchester, VA 22602

  117 Thompson Ct, Winchester, VA 22602
• 

  

  

  /21

  $156,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,093 Sq Ft

  154 Ashton Dr, Winchester, VA 22603

  NOTE: THIS PROPERTY IS UNAVAILABLE TO SEE BEFORE THE AUCTION. THE HIGH BIDDER WILL BE ALLOWED A HOME INSPECTION CONTINGENCY AND INSPECTION OF THE PROPERTY WITH RIGHT TO VOID THE CONTRACT IF NOT SATISFIED.****See Documents for Purchase Contract and Disclosure Documents****This Winchester home is one of a portfolio of 12 investment properties being sold at auction online ending on

  Alex Sharp

  Thornton River. LLC

  (540) 660-7206

  154 Ashton Dr, Winchester, VA 22603
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  /24

  $1,900 per month

  • 3 Beds
  • 1 Bath
  • 1,073 Sq Ft
  • House for Rent

  2325 Wilson Blvd, Winchester, VA 22601

  This well-maintained rancher in Winchester city limits is ready for immediate occupancy.This home features three bedrooms, one bathroom, a new kitchen countertop and sink, a new range hood, and new windows. It also has fresh paint throughout, a partially finished basement, and a large fenced backyard.We do not allow pets. A background check, references, and a one-month security

  Chuck Dondero Tetra Corporation

  2325 Wilson Blvd, Winchester, VA 22601
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  /80

  $685,000 Sold Sep 12, 2025

  • 2,333 Sq Ft
  • $294/SF
  • 9 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1994

  1153 Merrimans Ln, Winchester, VA 22602

  **HIGEST & BEST DUE BY SUNDAY, AUGUST 17, 5:00 P.M.** Welcome to this one-owner Cape Cod on sought-after Merrimans Lane, just steps from Roscommons. Thoughtfully designed and custom built, this home offers timeless style and comfortable living.Step inside to find gleaming hardwood floors, a well-appointed kitchen with a sunny breakfast area, and a lovely sunroom with direct access to the

  Traci Shoberg RE/MAX Roots

  1153 Merrimans Ln, Winchester, VA 22602
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  /36

  Est $440,082 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,522 Sq Ft

  151 Doonbeg Ct, Winchester, VA 22602

  151 Doonbeg Ct, Winchester, VA 22602
• 

  

  /42

  $344,900 Pending

  • 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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  /36

  $1,195 - $1,695 per month

  Fay Street Apartments

  1 - 3 Beds

  121 Fay St, Winchester, VA 22602

  NEW MANAGEMENT, NEW LOOK! Live on your own terms with Fay Street Apartments. Find thecomfort and convenience you crave among our one- and two-bedroom apartments, and three-bedroom townhomes, on our well-kept premises, and in the nearby, quaint town ofWinchester, VA. Our community opens doors to a myriad of opportunitieswill youreach out and seize them all?Start an exciting

  121 Fay St, Winchester, VA 22602
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  /40

  $699,900 Sold Sep 12, 2025

  • 2,342 Sq Ft
  • $299/SF
  • 64 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  200 Sweetbriar Ln, Winchester, VA 22603

  Welcome to your dream escape! This custom-built cabin on 7.02 acres in Winchester, VA offers the perfect blend of peace, privacy, and high-end living. Whether you're seeking a serene getaway or a functional farmette, this property has it all — with a mix of open pasture and woods, it’s ideal for animals, gardening, or simply soaking in nature.Step inside to find gleaming hardwood floors

  Lori Hoffman Realty ONE Group Old Towne

  200 Sweetbriar Ln, Winchester, VA 22603
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  /17

  Est $281,468 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 734 Sq Ft

  228 Weems Ln, Winchester, VA 22601

  228 Weems Ln, Winchester, VA 22601
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  /28

  $389,900

  • 4 Beds
  • 3 Baths
  • 1,888 Sq Ft

  408 Valley Mill Rd, Winchester, VA 22602

  Spacious Split Foyer Home in Winchester, VAConveniently located for both commuters and locals, this 2,128 sq. ft. split foyer home offers easy access to Route 7 and I-81, and is just minutes from FoodMaxx, Martin’s, and a variety of restaurants and fast-food options.Inside, you’ll find 4 comfortable bedrooms plus an additional lower-level room that can serve as a home office, gym,

  

  Carlos Soares

  Samson Properties

  (540) 583-4549

  408 Valley Mill Rd, Winchester, VA 22602
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  /33

  $1,850 per month

  • 3 Beds
  • 1 Bath
  • 1,098 Sq Ft
  • House for Rent

  1508 S Loudoun St, Winchester, VA 22601

  Property has been completely updated and is cute as can be with hardwood floors, updated kitchen, stylish black and white bath, 2 main level bedrooms with a nicely Finished Attic space perfect for 3rd bedroom, studio, or office. Attic is accessed through door in living room. Kitchen is modern looking with bar area, pendant lighting, and white cabinetry and offers easy access to side patio area

  Angela Duncan MarketPlace REALTY

  1508 S Loudoun St, Winchester, VA 22601
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  /55

  $500,000 Sold Sep 12, 2025

  • 3,612 Sq Ft
  • $138/SF
  • 155 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 2006

  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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  /83

  Est $922,676 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 4,632 Sq Ft

  420 N Hayfield Rd, Winchester, VA 22603

  420 N Hayfield Rd, Winchester, VA 22603
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  /47

  $315,000 Open Sat 1PM - 3PM

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft

  2964 Grace St, Winchester, VA 22601

  OPEN Sat 9/20 Wonderful Light filled 2 story Mid-Century Bungalow Updated for Modern Living while Maintaining its Original Charm and Style. An inviting Front Porch with Fabulous Wood Floors runs the length of the front of the home. Enter and Enjoy Beautiful Laminate Plank Floors and Arched Doorways and Recessed Lighting throughout the Main Floor. The Eat In Kitchen maintains it’s Cottage Core

  

  Jane Norton

  United Real Estate

  (540) 701-5940

  2964 Grace St, Winchester, VA 22601
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  /26

  $1,695 - $1,795 per month

  Fort Collier Terrace

  1 - 3 Beds

  900-1024 N Braddock St, Winchester, VA 22601

  Welcome to Fort Collier Terrace, an inviting community you'll love being part of. Our apartments in Winchester, VA, come in one, two, and three-bedroom layouts that range from 800 to 1,000 square feet. Aside from the generous living quarters, you'll find everything you need to feel right at home.Located near N Cameron Street and Martinsburg Pike, you're a stone's throw away from the top dining,

  900-1024 N Braddock St, Winchester, VA 22601
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  /21

  $539,000 Sold Sep 10, 2025

  • 2,443 Sq Ft
  • $221/SF
  • 5 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2004

  124 Van Gogh Terrace, Winchester, VA 22602

  Spacious colonial in Sovereign Village offering 4 bedrooms, 3.5 baths, and over 2,400 sq ft of living space on nearly a half acre lot. The main level features Luxury Vinyl Plank flooring throughout, a formal dining room with crown molding and wainscotting, and a Kitchen that opens to the Living room. Upper level includes a HUGE primary suite with private bath, PLUS and additional bedroom with a

  Phyllis Guthrie Keller Williams Realty

  124 Van Gogh Terrace, Winchester, VA 22602
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  /3

  Est $223,000 Not Listed For Sale

  403 Panther Dr, Winchester, VA 22602

  403 Panther 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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  /38

  $2,195 per month

  • 4 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • House for Rent

  224 Lake Sever Dr, Winchester, VA 22603

  This Split Foyer has been completely renovated. All new flooring ,finishes and freshly painted throughout. Located on cul-de-sac.Great commuter location, easy access to Route 7. Home features 4 bedrooms (2 up, 2 down) 2 full baths (1 up, 1 down). Kitchen/dining combo. Family/Rec room in basement. Deck on rear of home with large rear yard.

  Steve DuBrueler Coldwell Banker Premier

  224 Lake Sever Dr, Winchester, VA 22603
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  /50

  $750,000 Sold Sep 10, 2025

  • 5,802 Sq Ft
  • $129/SF
  • 4 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2001

  1205 Caroline St, Winchester, VA 22601

  **Do Not Miss This One!** Don’t miss this rare opportunity in the heart of Winchester! Offered for the first time since it was custom built in 2001, this stunning all-brick ranch sits on a beautifully landscaped and private 0.94-acre lot that feels like your own personal park complete with a stand of walnut trees. With nearly 3,000 square feet of thoughtfully designed space on the main level,

  Jim Shebest Coldwell Banker Realty

  1205 Caroline St, Winchester, VA 22601
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  /36

  Not Listed For Sale

  • Studio
  • 3,790 Sq Ft

  912 S Braddock St, Winchester, VA 22601

  912 S Braddock St, Winchester, VA 22601
• 

  

  /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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  /22

  $1,450 - $1,790 per month

  Blue Ridge Apartments

  2 - 4 Beds

  2260 Wilson Blvd, Winchester, VA 22601

  Discover the perfect blend of comfort and convenience at Blue Ridge Apartments in Winchester, VA. Our recently updated homes feature a variety of floor plans. Nestled in a pet-friendly community, you're just minutes away from Winchester's scenic spots, historic downtown, Apple Blossom Mall, and major employers. With easy access to I-81 and Route 7, the best of Winchester is always within reach.

  2260 Wilson Blvd, Winchester, VA 22601
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  /70

  $789,000 Sold Sep 10, 2025

  • 3,178 Sq Ft
  • $248/SF
  • 15 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2000

  850 Dicks Hollow Rd, Winchester, VA 22603

  If you’ve been searching for the perfect balance of privacy and convenience, look no further. This beautiful brick home is nestled on 6 scenic acres—complete with a pond and wooded backdrop—yet located just 15 minutes from downtown Winchester. A charming front porch welcomes you to sit and enjoy your morning coffee while taking in the peaceful surroundings and beautifully landscaped

  Rhonda Shade ERA Oakcrest Realty, Inc.

  850 Dicks Hollow Rd, Winchester, VA 22603
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  /49

  Est $416,014 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  110 W Monmouth St, Winchester, VA 22601

  110 W Monmouth 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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  /25

  $2,700 per month

  • 3 Beds
  • 2.5 Baths
  • 1,657 Sq Ft
  • House for Rent

  106 Manasquan Way, Winchester, VA 22602

  Welcome to 106 Manasquan Way — a beautiful, Brand NEW 3-bedroom, 2.5-bath single-family home located in the highly sought-after Retreat at Winding Creek community in Winchester, VA! Be the first to enjoy this thoughtfully designed home offering an open-concept layout, abundant natural light, and modern finishes throughout.The main level features a spacious living area, dining space, and a

  Sadaf Alhooie Keller Williams Realty

  106 Manasquan Way, Winchester, VA 22602
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  /27

  $333,000 Sold Sep 10, 2025

  • 1,024 Sq Ft
  • $325/SF
  • 78 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1955

  509 W Cork St, Winchester, VA 22601

  Location, Location, Location! Nestled in the heart of Winchester on the sought-after west side, this recently renovated 3-bedroom, 1-bath home offers modern comforts with a touch of classic charm. Step inside to discover a brand-new kitchen featuring gleaming white cabinets and exquisite granite countertops, perfect for culinary enthusiasts. The updated bathroom boasts a stylish tiled tub,

  Dan Whitacre Colony Realty

  509 W Cork St, Winchester, VA 22601
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  /66

  Not Listed For Sale

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

  703 S Loudoun St, Winchester, VA 22601

  703 S Loudoun St, Winchester, VA 22601
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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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  /11

  $1,050 - $1,300 per month

  North Winchester Apartments

  1 - 2 Beds

  800 Thomas Ct, Winchester, VA 22601

  Now Leasing: 1 & 2 Bedroom Apartments Available Now! In-unit washer and dryerWater and garbage includedEnjoy a serene, peaceful settingDon't miss out—these are first come, first serve!

  800 Thomas Ct, Winchester, VA 22601
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  /38

  $355,000 Sold Sep 09, 2025

  • 2,668 Sq Ft
  • $133/SF
  • 10 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1977

  109 Arrowhead Trail, Winchester, VA 22602

  Have you been waiting for the perfect home in Shawneeland? Look no further. This fantastic split-foyer has been recently renovated and is ready for you! Upgrades include a brand new asphalt shingle roof, new vinyl plank flooring throughout, fresh paint, and a total overhaul of the laundry room. The home boasts three spacious bedrooms, a large family room, an enormous basement rec room, and two

  Kristin Crosby Samson Properties

  109 Arrowhead Trail, Winchester, VA 22602
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  /2

  Est $298,793 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  127 S Euclid Ave, Winchester, VA 22601

  127 S Euclid Ave, 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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  /17

  $1,600 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Townhouse for Rent

  202 Banbury Terrace, Winchester, VA 22601

  2 bedrooms one bath in the desirable community of Huntington Meadows Conveniently located close to route seven and interstate 81 and a mile From historic downtown, Winchester. Gorgeous all wood floors throughout. Fresh interior paint new deck new HVAC new hot water heater. Pets case by case Owner is requesting strong credit and income $42 app fee

  Carolyn Waymack Crum Realty, Inc.

  202 Banbury Terrace, Winchester, VA 22601
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  /39

  $734,807 Sold Sep 09, 2025

  • 3,567 Sq Ft
  • $206/SF
  • 26 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2025

  103 Wagtail Ln, Winchester, VA 22603

  Step into the Sierra 39-F2 – Homesite 1025 at Hiatt Pointe (55+)—a two-car, front-load garage SINGLE FAMILY home with four bedrooms and three full bathrooms will be ready IMMEDIATELY.. Designed for ease and everyday function, this factory-framed floorplan is as innovative as it stylish! Enter through the inviting front porch and be immediately welcomed by 9’ ceilings on both levels, oak main

  Shannon L Bray Pearson Smith Realty, LLC

  103 Wagtail Ln, Winchester, VA 22603
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  /72

  Est $878,189 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,340 Sq Ft

  2101 Cedar Grove Rd, Winchester, VA 22603

  2101 Cedar Grove Rd, Winchester, VA 22603

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