Winchester, VA Homes

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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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  /33

  $1,550 - $1,750 per month

  Madison Village Apartments (Winchester)

  1 - 2 Beds

  110 Bulmer Loop, Winchester, VA 22602

  Our community is perfect for those who enjoy spending time outside living a healthy, lively lifestyle by using the walking trails, outdoor common areas, and dog park, as well as for those who appreciate a home that is a retreat from the business of everyday life. We are conveniently located a few short miles from Shenandoah University, I-81, Rt. 8 and Rt. 50 in Winchester, VA. Our apartments

  110 Bulmer Loop, Winchester, VA 22602
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  /43

  $310,000 Sold Sep 09, 2025

  • 1,299 Sq Ft
  • $239/SF
  • 80 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1982

  341 Opequon Ave, Winchester, VA 22601

  Welcome home to this charming 3-bedroom, 1.5-bath gem perfectly located for easy access to I-81, Route 50, and Route 7—ideal for commuters. SEE VIDEO attached :)Enjoy the convenience of a main-level laundry room and peace of mind with a new roof installed in 2018. Step outside to your fully fenced backyard, complete with a screened-in porch and storage shed, perfect for relaxing or extra

  Sheila Pack RE/MAX Roots

  341 Opequon Ave, Winchester, VA 22601
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  /19

  Est $436,765 Not Listed For Sale

  • 2 Beds
  • 4 Baths
  • 2,052 Sq Ft

  204 N Kent St, Winchester, VA 22601

  204 N Kent St, Winchester, VA 22601
• 

  

  

  /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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  /36

  $2,291 per month

  • 4 Beds
  • 3.5 Baths
  • 2,100 Sq Ft
  • Townhouse for Rent

  107 Boone Ct, Winchester, VA 22602

  1st 6 months special rent of $2291.This brand-new home is currently under construction and offers a complete, modern interior. Featuring 4 bedrooms, 3.5 baths, a 2-car garage, a 10' x 16' composite deck, and a fenced yard. The lower level includes a private bedroom with a full bath and walk-out access. The main level boasts luxury vinyl tile flooring throughout, a beautifully open floor

  Raj Patel Ikon Realty - Ashburn

  107 Boone Ct, Winchester, VA 22602
• 

  

  /34

  $265,000 Sold Sep 09, 2025

  • 960 Sq Ft
  • $276/SF
  • 90 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1989

  2301 Tower Ave, Winchester, VA 22601

  Welcome to this charming and cozy budget friendly home. With 3 bedrooms on the main level and a full basement below with tons of room for future expansion that walks out to a large off-street parking area this home is bursting with potential! The big ticket items are already there with newer high-end appliances, heat pump and central air, 200 amp service, etc this home is ready for your cosmetic

  Clint Pierpoint NextHome Realty Select

  2301 Tower Ave, Winchester, VA 22601
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  /66

  Est $569,403 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,930 Sq Ft

  3392 Back Mountain Rd, Winchester, VA 22602

  3392 Back Mountain Rd, 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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  /17

  $500 - $2,000 per month

  Brookfield Corporate Apartments

  1 - 2 Beds

  548 Brookfield Dr, Winchester, VA 22601

  We are excited to share that we are under new ownership and management, and we're eager to welcome new guests to our community.Located at 500 Brookfield Drive, Winchester, VA 22601, Brookfield Corporate Apartments offers spacious, fully furnished one and two-bedroom apartments. Each apartment is designed with your comfort in mind and comes equipped with linens, kitchenware, two TVs with

  548 Brookfield Dr, Winchester, VA 22601
• 

  

  /35

  $399,999 Sold Sep 08, 2025

  • 1,630 Sq Ft
  • $245/SF
  • 1 Day On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1900

  125 E Clifford St, Winchester, VA 22601

  Step into the past with this beautifully preserved home, believed to be built in the 1840s, located in the heart of downtown, complete with a historical plaque. Full of timeless charm, this 3-bedroom, 1-bath residence features original hand-hewn log beams, wide-plank wood floors, and authentic period details throughout. Enjoy a warm, inviting living space with exposed wood beams that highlight

  Leigh Phillips MarketPlace REALTY

  125 E Clifford St, Winchester, VA 22601
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  /5

  Est $139,184 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,508 Sq Ft

  197 Dairy Corner Place, Winchester, VA 22602

  197 Dairy Corner Place, Winchester, VA 22602
• 

  

  /35

  $499,900

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

  1420 Fishel Rd, Winchester, VA 22602

  Nestled away in the trees, this updated retreat on 2.67 acres offers the perfect blend of peace, privacy, and one-level living. Inside, you’ll find 3 bedrooms, 2 renovated baths, brand-new flooring, and fresh paint throughout. The bright eat-in kitchen with island and stainless appliances flows into a spacious sitting room, enclosed rear porch with A/C, and a covered front porch for year-round

  

  Katherine (Kat) Wetzel

  Century 21 Redwood Realty

  (540) 779-1383

  1420 Fishel Rd, Winchester, VA 22602
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  /48

  $1,800 per month

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft
  • Townhouse for Rent

  344 National Ave, Winchester, VA 22601

  Step into timeless charm with this delightful 1930's brick duplex, a true gem of the past blending seamlessly with modern living. Boasting wood floors and charming built-ins, this 3 bedroom, 2 full bath home exudes character from every corner. The unfinished basement offers endless possibilities, while the fourth-level attic is already floored and ready to be transformed or used for additional

  Jay Thomas Keller Williams Realty

  344 National Ave, Winchester, VA 22601
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  /36

  $465,000 Sold Sep 08, 2025

  • 1,784 Sq Ft
  • $261/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 1991

  119 Stonedown Ln, Winchester, VA 22603

  Welcome to 119 Stonedown Lane, a stunning renovated rancher that combines modern style with tranquil country living. Set on a private 2.61-acre lot, this 3-bedroom, 2-bathroom home offers the perfect balance of space, comfort, and convenience, just minutes from historic downtown Winchester and easy access to Interstate 81. Inside, you’ll be greeted by cathedral ceilings and a living area that

  Jon Fleming Weichert Realtors - Blue Ribbon

  119 Stonedown Ln, Winchester, VA 22603
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  /37

  Not Listed For Sale

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

  216 E Piccadilly St, Winchester, VA 22601

  216 E Piccadilly St, Winchester, VA 22601
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  /53

  $628,000

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

  320 Linden Dr, Winchester, VA 22601

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

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 274-0212

  320 Linden Dr, Winchester, VA 22601
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  /22

  $1,995 per month

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Condo for Rent

  446 N Loudoun St Unit 1, Winchester, VA 22601

  Live in this upscale turn of the Century 3 bed 1 bath charmer. Live in old town Winchester just 2 blocks off the Mall. Enjoy everything Old Town has to offer restaurants, shopping, entertainment, and more. This property boasts a modern upgraded kitchen with granite, soft close cabinets, high ceilings with recessed lighting, large kitchen sink, matching stainless Steel appliances and a shelved

  446 N Loudoun St Unit 1, Winchester, VA 22601
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  /46

  $379,900 Sold Sep 08, 2025

  • 1,942 Sq Ft
  • $196/SF
  • 5 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1988

  108 Meadowbrooke Place, Winchester, VA 22602

  We can't wait for you to make this charming home your own!Located in the established and inviting neighborhood of Greenwood Heights, this 4-bedroom, 2-bath home sits on a peaceful, well-maintained lot. Just minutes from Rt-7 and I-81, it offers an ideal location for commuters with convenient access to shopping, dining, and more.Step inside to a cozy living room that flows seamlessly

  Justin Mistretta Berkshire Hathaway HomeServices PenFed Realty

  108 Meadowbrooke Place, Winchester, VA 22602
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  /21

  Est $313,352 Not Listed For Sale

  • Studio
  • 539 Sq Ft

  3464 Papermill Rd, Winchester, VA 22602

  3464 Papermill Rd, Winchester, VA 22602
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  /12

  $54,900

  • Land
  • 0.73 Acre
  • $75,205 per Acre

  LOTS 7 & 8 Manor Dr, Winchester, VA 22602

  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 some space between neighbors. Lots 7 & 8 are being sold

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 565-5562

  LOTS 7 & 8 Manor Dr, Winchester, VA 22602
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  /9

  $2,300 per month

  • 3 Beds
  • 3.5 Baths
  • 2,233 Sq Ft
  • Townhouse for Rent

  102 Metcalf Terrace, Winchester, VA 22602

  Beautiful townhome with an open floor plan, featuring quartz countertops, LVT flooring, and a modern gray and white color palette. Enjoy a spacious deck that backs to trees, with numerous upgrades throughout! Excellent credit required; no pets, and No Smoking. Conveniently located near downtown Winchester.

  Steve DuBrueler Coldwell Banker Premier

  102 Metcalf Terrace, Winchester, VA 22602
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  /8

  $160,000 Sold Sep 08, 2025

  • Land
  • 0.36 Acre
  • $444,444 per Acre

  • 44 Days On Market

  2812 Saratoga Dr, Winchester, VA 22601

  A rare find and jewel of a lot! .36 acres in the perfect location on the south side of Winchester city limits. A short walk to Creekside Station with shopping and dining and the Kernstown Battlefield. Enjoy the quiet street with sidewalks and the bonus...water/sewer taps have been paid! Well maintained homes on either side make this a strong investment for a builder or create your custom

  Dave Spence RE/MAX Roots

  2812 Saratoga Dr, Winchester, VA 22601
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  /2

  Est $197,989 Not Listed For Sale

  • Studio

  128 Rappahannock Trail, Winchester, VA 22602

  128 Rappahannock Trail, Winchester, VA 22602
• 

  

  /23

  $795,600 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,102 Sq Ft

  111 Babbs Mountain Rd, Winchester, VA 22603

  Modern Elegance on 1.6 Acres – To Be Built!Experience contemporary living at its finest with this stunning 3-bedroom, 2.5-bathroom home, expertly designed by Fauver and Browning Homes. Nestled on 1.6 scenic acres just outside Winchester, this home offers breathtaking views of the rolling meadows leading to Apple Pie Ridge.Spanning 2,102 sq. ft., this home blends modern design with

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 329-8240

  111 Babbs Mountain Rd, Winchester, VA 22603
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  /133

  $1,700 per month

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

  342 Fairmont Ave Unit 5 FULLY FURNISHED RENTAL Retro Loves Company, Winchester, VA 22601

  COMPLETELY FURNISHED RENTALPerfect for traveling professionals or students.Furnished one bedroom located behind the beautiful Handley library. This quaint one bedroom apartment is on the 3rd floor of a historic home facing Fairmont Ave. It has terrific views and a spectacular view of fireworks on Apple Blossom, July 4th and New Years Eve. Beautiful details and wainscotting, built in

  342 Fairmont Ave Unit 5 FULLY FURNISHED RENTAL Retro Loves Company, Winchester, VA 22601
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  /58

  $575,000 Sold Sep 08, 2025

  • 3,386 Sq Ft
  • $170/SF
  • 84 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2016

  327 Lynnehaven Dr, Winchester, VA 22602

  Back to market! Previous buyers got cold feet! Their loss is your gain! Welcome to the community of Lynnehaven! This property is one of the few sought-after models offering three bedrooms plus a dedicated office all conveniently located on the main level. This beautifully maintained home, lovingly cared for by its original owner, features an open floor plan with gleaming hardwood floors

  Ryan Rice Keller Williams Capital Properties

  327 Lynnehaven Dr, Winchester, VA 22602
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  /3

  Not Listed For Sale

  2902 Valley Ave, Winchester, VA 22601

  2902 Valley Ave, Winchester, VA 22601
• 

  

  /44

  $496,129 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,195 Sq Ft

  117 Wagtail Ln, Winchester, VA 22603

  Embrace the Vera 30-F2 – Homesite 1031 at Hiatt Pointe—a two-car, front-load garage VILLA with three bedrooms, two full bathrooms, and one half bathroom will be ready IMMEDIATELY. Built for the way you live, this factory-framed floorplan makes room for moments big and small. Be welcomed by 9’ ceilings on both levels, oak main stairs, and expertly selected finishes that make this villa feel

  Shannon L Bray Pearson Smith Realty, LLC

  117 Wagtail Ln, Winchester, VA 22603
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  /32

  $2,200 per month

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft
  • House for Rent

  3290 Shawnee Dr, Winchester, VA 22602

  Conveniently located between I-81 and Route 11, this brick rambler offers the perfect blend of accessibility and comfort. Enjoy one-level living with a spacious living room and a cabinet-filled eat-in kitchen with a handy laundry closet. 3 sizeable bedrooms share one full bathroom and there is a half bath for added convenience. Enjoy outdoor living on the covered rear porch overlooking the

  Heloisa Amar Samson Properties

  3290 Shawnee Dr, Winchester, VA 22602
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  /9

  $110,000 Sold Sep 08, 2025

  • Land
  • 0.12 Acre
  • $916,667 per Acre

  • 309 Days On Market

  116-118 W Leicester St, Winchester, VA 22601

  Unique opportunity to own a piece of land in Historic Downtown Winchester. Located between Braddock and Washington Streets South of the Old Town Walking Mall. The property is within steps to Washington Street and the Apple Blossom Festival Parade route. The lots are located within the Historic District of Winchester. Two parcels are included in this listing. Previously, the lots were

  Kim Hurst MarketPlace REALTY

  116-118 W Leicester St, Winchester, VA 22601
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  /38

  Est $318,613 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,380 Sq Ft

  1172 Purcell Ln, Winchester, VA 22603

  1172 Purcell Ln, Winchester, VA 22603
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  /31

  $599,990 New Construction

  • 3 - 5 Beds
  • 2 - 4 Baths
  • 1,841+ Sq Ft

  Matisse Plan at Hiatt Pointe at Snowden Bridge - 55+ Single Family Homes Collection, Winchester, VA 22603

  Experience the epitome of modern living in the Matisse. This thoughtfully designed home offers main-level living at its finest, providing unparalleled comfort and flexibility to suit your unique lifestyle. The heart of the home is an open-concept haven, seamlessly blending a gourmet kitchen, dining room, and spacious family room. The kitchen, a chef's dream, features a functional island,

  

  Brookfield Residential

  Builder

  105 Wagtail Ln Unit 36578843, Winchester, VA 22603
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  /20

  $1,431 - $1,650 per month

  Preston Place - Tax Credit

  2 - 3 Beds

  124 Castlebridge Ct, Winchester, VA 22602

  Preston Place Apartments and Townhomes are a remarkable blend of style and value. Almost everything is nearby, from schools to shopping, restaurants, parks and interstate highways. Conveniently located on Airport Drive one-half mile from the Winchester Regional Airport. Dulles Airport is also less than thirty minutes away. It’s hard to find a more convenient location.

  124 Castlebridge Ct, Winchester, VA 22602
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  /42

  $435,000 Sold Sep 05, 2025

  • 2,543 Sq Ft
  • $171/SF
  • 7 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1994

  214 Cavalry Dr, Winchester, VA 22602

  Brick Front Colonial on a peaceful Cul-de-sac in the desirable Pioneer Heights. This spacious home offers 4 Bedrooms, 2.5 baths, and 2,543 finished sq. ft., 2 car garage, with covered deck and fully fenced rear yard. 2 HVAC Units replaced 4 years ago, roof was replaced 10 years ago, stainless frig & stove 5 years old. New luxury vinyl plank flooring on 2nd level, hardwood floors on main

  Cara Wilkins MarketPlace REALTY

  214 Cavalry Dr, Winchester, VA 22602
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  /36

  Est $509,494 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,479 Sq Ft

  1960 Siler Rd, Winchester, VA 22603

  1960 Siler Rd, Winchester, VA 22603
• 

  

  /23

  $374,990 New Construction

  • 3 Beds
  • 1.5 Baths
  • 1,752+ Sq Ft

  Northgate Plan at Hiatt Pointe at Snowden Bridge - 55+ Villas Collection, Winchester, VA 22603

  This stunning two-level villa boasts a modern open concept design that seamlessly connects living spaces for an inviting and spacious feel. The main level features a living room that opens effortlessly to the dining area, creating a perfect space for entertaining and family gatherings. The expansive rear kitchen includes an L-shaped layout with an eating bar and an island with additional bar

  

  Brookfield Residential

  Builder

  105 Wagtail Ln Unit 36578847, Winchester, VA 22603
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  /9

  $1,995 per month

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Townhouse for Rent

  446 N Loudoun St, Winchester, VA 22601

  Charming Victorian - Downtown Winchester LivingRecently renovated turn-of-the-century Victorian featuring:- Upgraded kitchen with granite countertops, pantry closet, & recessed lighting- Luxury vinyl plank flooring throughout- Modern tile bathroom with washer/dryer included- Central heat & air for year-round comfort- Single-floor living with convenient layout-

  Lawrence Lessin Homes By Owner, Inc.

  446 N Loudoun St, Winchester, VA 22601
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  /14

  $312,000 Sold Sep 05, 2025

  • 1,704 Sq Ft
  • $183/SF
  • 65 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1940

  10 Richards Ave, Winchester, VA 22601

  Back on the market with updated baths and brand-new flooring in the enclosed porch! Welcome to this charming classic home located in the City of Winchester. Built in 1940, this home offers timeless appeal and craftsmanship. Inside, you'll find 3 bedrooms, 1.5 baths, and a versatile fourth room—ideal for a home office, guest room, or creative space. The main level greets you with a welcoming

  Lindsey Richardson ERA Oakcrest Realty, Inc.

  10 Richards Ave, Winchester, VA 22601
• 

  /2

  Not Listed For Sale

  • Studio
  • 1,693 Sq Ft

  408 Diehl St, Winchester, VA 22601

  408 Diehl St, Winchester, VA 22601

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