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Homes for Sale near The Independent School of Winchester

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  • /30

    $285,000

    • 3 Beds
    • 1 Bath
    • 1,176 Sq Ft

    1116 Opequon Ave, Winchester, VA 22601

    Discover this charming and well maintained home at 1116 Opequon Avenue, offering an excellent opportunity as a starter home or investment property. Located just minutes from Old Town Winchester, this home provides convenience, comfort, and value for under 300K. The main level features hardwood floors throughout the living spaces, three bedrooms, and a full bathroom. The full basement offers great

    Agent Photo

    Bradley Comstock

    ERA Oakcrest Realty, Inc.

    (540) 413-0030

    1116 Opequon Ave, Winchester, VA 22601
  • /29

    $295,000

    • 3 Beds
    • 1 Bath
    • 1,325 Sq Ft

    312 Shawnee Ave, Winchester, VA 22601

    Within walking distance to Historic Downtown Winchester! Public record square footage was found to be inaccurate - listing square footage has been adjusted and price adjusted accordingly. This home is convenient to everything happening in Winchester and also a very easy location for commuters. Nestled in the charming Shawnee Heights neighborhood, this delightful cottage-style home offers a

    Agent Photo

    Lori Bales

    Keller Williams Realty

    (540) 209-9771

    312 Shawnee Ave, Winchester, VA 22601
  • /39

    $274,000

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    423 Highland Ave, Winchester, VA 22601

    Charming Winchester Home – Don’t Let This One Slip Away! Welcome to this beautifully refreshed home in the heart of Winchester, offering exceptional value, versatility, and convenience. Thoughtfully updated throughout, this property is move-in ready while still leaving room to make it your own. Enjoy ample off-street parking for up to 8 cars with rear access from West Lane, fresh renovations,

    Agent Photo

    Carlos Soares

    Samson Properties

    (540) 924-3305

    423 Highland Ave, Winchester, VA 22601
  • /88

    $445,000

    • Studio
    • 2,152 Sq Ft

    26 A Jackson Ave, Winchester, VA 22601

    Rare Opportunity: Turnkey Duplex in Winchester – Vacant, Updated, and Ready for Your Next Move! A rare and an exceptional opportunity to own a two-unit duplex in Winchester City— vacant and ready for your plans. Whether you’re an investor seeking strong cash flow or an owner-occupant looking to live in one unit and rent the other, this property offers flexibility, income potential, and low

    Agent Photo

    Melanie Lucero

    Real Broker, LLC

    (540) 386-1285

    26 A Jackson Ave, Winchester, VA 22601
  • /55

    $659,000

    • 5 Beds
    • 2.5 Baths
    • 3,420 Sq Ft

    501 Jefferson St, Winchester, VA 22601

    Welcome Home!If you’ve been searching for an updated home in a prime location, this is it! This stunning 5BR/3BA property has been completely renovated from top to bottom—and it shows. Step inside to an open floor plan where natural light fills the gorgeous kitchen, featuring quartz countertops, stainless steel appliances, and plenty of space to gather. The adjoining family room opens to a

    Agent Photo

    Jeanne Mezzatesta

    Colony Realty

    (540) 306-5775

    501 Jefferson St, Winchester, VA 22601
  • /13

    $300,000

    • 3 Beds
    • 2 Baths
    • 1,072 Sq Ft

    112 Star Fort Dr, Winchester, VA 22601

    Unlock the Potential! 3BR/2BA Fixer-Upper in Winchester/Frederick County. Nestled in a quiet Cul De Sac in Frederick County, this 3-bedroom, 2-bath home is bursting with potential and ready for a visionary buyer to bring it back to life. Whether you're looking to renovate and resell or transform this into a charming personal residence, the canvas is yours to create something

    Agent Photo

    Kimberly Schroeder

    Long & Foster Real Estate, Inc.

    (540) 502-3981

    112 Star Fort Dr, Winchester, VA 22601
  • /2

    $365,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 1,780 Sq Ft

    127 Shirley St, Winchester, VA 22601

    Comfortable living at this split-foyer home located in the heart of the City of Winchester. On the main level, you’ll find three bedrooms and a full bath. The lower level features a fourth bedroom plus a second full bath — ideal for guests, or a home office. Location is a standout. You’re just minutes from downtown dining, shopping, and community events, and enjoy easy access to schools, parks,

    Agent Photo

    Bradley Comstock

    ERA Oakcrest Realty, Inc.

    (540) 802-5087

    127 Shirley St, Winchester, VA 22601
  • /41

    $345,000

    • 3 Beds
    • 2 Baths
    • 1,066 Sq Ft

    105 W Oates Ave, Winchester, VA 22601

    This beautifully updated and lovingly maintained home is located in the much loved heart of Winchester. Gleaming hardwood floors welcome you as soon as you enter and that is only the beginning! This sweet home is light filled and happy. Spacious living and dining areas with new recessed lights. The kitchen shines as well with updated lighting, new quartz countertops, sink, coffee bar and

    Agent Photo

    Layne Jensen

    CENTURY 21 New Millennium

    (540) 787-2080

    105 W Oates Ave, Winchester, VA 22601
  • /28

    $389,990 New Construction

    • 3 Beds
    • 3.5 Baths
    • 1,658 Sq Ft

    205 Monteith Dr, Winchester, VA 22601

    OPEN HOUSE: Saturday - Sunday 1pm - 3pm 3 level/3 bedroom townhome with a chef’s kitchen and 1 car garage located in the heart of Winchester! MOVE-IN READY! The Bedford II 3 level interior row townhome that backs to TREES with a stone water table on the front and side of the home along with a box bay window and a 1 car garage featuring 3 Bedrooms and 3.5 Baths and 1,658 square feet with 10 x 14

    DRB Homes Builder
    205 Monteith Dr, Winchester, VA 22601
  • /30

    $411,896 New Construction

    • 3 Beds
    • 3.5 Baths
    • 1,658 Sq Ft

    214 Monteith Dr, Winchester, VA 22601

    OPEN HOUSE: Saturday - Sunday 1pm - 3pm 3 Level Townhome with 3 bedrooms! Come and see Winchester's BRAND NEW LUXURY TOWNHOME COMMUNITY. Step into modern living with this stunning 3-level townhome offering 3 bedrooms and 3.5 baths. Designed for comfort and style, this home features box bay windows in both the front and rear, filling every floor with natural light. Enjoy the convenience of an

    DRB Homes Builder
    214 Monteith Dr, Winchester, VA 22601
  • /24

    $389,990 New Construction

    • 3 Beds
    • 3.5 Baths
    • 1,658 Sq Ft

    210 Monteith Dr, Winchester, VA 22601

    OPEN HOUSE: Saturday - Sunday 1pm - 3pm Beautiful open concept living 3 level townhome with Lower Level Walkout! The Bedford II 3 level interior town home with a box bay window with 1 car garage featuring 3 Bedrooms and 3.5 Baths and 1,658 square feet. It is fully finished top to bottom. The front door with the electronic Ring door camera leads directly into the spacious lower-level recreation

    DRB Homes Builder
    210 Monteith Dr, Winchester, VA 22601
  • /23

    $422,539 New Construction

    • 3 Beds
    • 3.5 Baths
    • 1,658 Sq Ft

    201 Monteith Dr, Winchester, VA 22601

    OPEN HOUSE: Saturday - Sunday 1pm - 3pm End Of Row Townhome With 1 Car Garage & Rear Deck! MOVE-IN READY! The Bedford II 3 level with 1 car garage featuring 3 Bedrooms and 3.5 Baths and 1,658 square feet. The front door with the electronic Smart Home Technology package leads directly into the spacious lower-level recreation room with 9 ft. ceilings. The foyer with luxury vinyl plank, a double

    DRB Homes Builder
    201 Monteith Dr, Winchester, VA 22601
  • /26

    $389,990 New Construction

    • 3 Beds
    • 3.5 Baths
    • 1,630 Sq Ft

    Bedford II Plan at Village at Valor Crossing - Townhomes, Winchester, VA 22601

    OPEN HOUSE: Saturday - Sunday 1pm - 3pm Covered front porch leads into the foyer. Attached 1 car garage or optional flex room or study. Open concept kitchen located next to the country kitchen and living room. Box bay rear window and 10' x 14' Trex deck. Owner’s suite with large walk-in closet, dual vanity, and oversized seated shower in owner’s bath. Fireplace option available in select homes.

    DRB Homes Builder
    0 Tbd Weems Ln Unit 36470375, Winchester, VA 22601
  • /41

    $77,700

    • Land
    • 6.09 Acres
    • $12,759 per Acre

    440 Iris Ln, Winchester, VA 22602

    Owner Financing Available! (see details below)Enjoy breathtaking, unrivaled views of the Shenandoah Valley below from this ridgetop property on Little North Mountain.Property Overview:Address: 440 Iris Lane, Winchester, VA 22602Size: 6.09 AcresKey Features:Gorgeous Sunset Valley ViewsTwo Lots in One Build on Both or Split Off!Extensive Road

    Robert Scott AcreTown.com

    440 Iris Ln, Winchester, VA 22602
  • /43

    $564,900 Open Sat 1PM - 3PM

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

    687 Woodland Ave, Winchester, VA 22601

    Experience refined living in this stunning two-level brick residence, designed with an open-concept layout that seamlessly blends sophistication and comfort. The home features 4 spacious bedrooms, each with a private full bathroom.The kitchen boasts granite countertops and elegant finishes, flowing effortlessly into the dining and living areas — perfect for entertaining or relaxing by the gas

    Mauricio Argandona Fairfax Realty Select

    687 Woodland Ave, Winchester, VA 22601
  • /34

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 1,978 Sq Ft

    236 Miller St, Winchester, VA 22601

    Charming 3 Bedroom, 2.5 Bath Colonial just blocks from Old Town Winchester, offering easy access to dining, entertainment, and shopping! Enjoy outdoor living on the spacious covered front porch or in the fenced backyard. The landscaping features beautiful lilac and rose bushes. The eat-in kitchen features granite countertops, a tile backsplash, hardwood floors, and newer stainless steel

    Sheila Pack RE/MAX Roots

    236 Miller St, Winchester, VA 22601
  • /95

    $660,000

    • 4 Beds
    • 3.5 Baths
    • 4,101 Sq Ft

    608 Kernstown Ct, Winchester, VA 22601

    Discover the charm and serenity of suburban living at 608 Kernstown Court, nestled in the storied landscape of Winchester, Virginia. This picturesque address offers an ideal blend of history, convenience, and modern comfort, an inviting sanctuary for families, professionals, or anyone seeking a peaceful yet well connected lifestyle.This desirable property features a beautifully appointed

    Aaron Richert Realty FC, LLC

    608 Kernstown Ct, Winchester, VA 22601
  • /116

    $599,900

    • 3 Beds
    • 1.5 Baths
    • 2,874 Sq Ft

    510 S Washington St, Winchester, VA 22601

    Welcome to a piece of Winchester History. This historic Colonial Revival residence, built of enduring brick construction, offers an opportunity of owning a significant piece of the city's heritage. Situated on a .20 city acre lot, this property is ideally positioned directly on the route of the Shenandoah Apple Blossom Festival Parade, offering unparalleled viewing opportunities.With winter

    Laurie Webber Century 21 Modern Realty Results

    510 S Washington St, Winchester, VA 22601
  • /25

    $625,000

    • 5 Beds
    • 4 Baths
    • 3,550 Sq Ft

    681 Hillman Dr, Winchester, VA 22601

    This beautiful home is only 2 years young! Main floor bedroom + full bath! Thoughtfully designed and meticulously maintained, this property blends comfort, style, and functionality across every level. The attached 2-car garage provides convenience and additional storage. Designer finishes, a spacious custom shower, and elegant details that create a spa-like experience. The finished basement

    Sarah Reynolds Keller Williams Realty

    681 Hillman Dr, Winchester, VA 22601
  • /48

    $550,000

    • 3 Beds
    • 1.5 Baths
    • 2,177 Sq Ft

    216 Fairmont Ave, Winchester, VA 22601

    Classy colonial on the stately Fairmont Avenue with million dollar homes nearby, walking mall in close proximity with a plethora of boutique shops and eateries. The 2000 square feet is designed for comfort and coziness accented by 9ft ceilings, sunlit formal rooms, a well appointed kitchen, spacious bedrooms, adorable loft on 3rd level for a playroom/den/office, and the best part is entering your

    Dave Spence RE/MAX Roots

    216 Fairmont Ave, Winchester, VA 22601
  • /46

    $599,900

    • 3 Beds
    • 2 Baths
    • 1,946 Sq Ft

    289 Westview Dr, Winchester, VA 22603

    Welcome to your private contemporary retreat at 289 Westview Drive in Winchester, VA! This truly exceptional property offers the ultimate escape, situated on over 13 magnificent acres with gorgeous mature trees, stunning views, and unparalleled peace and quiet. Step inside the sun-filled main level, featuring an open layout that seamlessly connects the living room, dining room, and kitchen.

    Dan Whitacre Colony Realty

    289 Westview Dr, Winchester, VA 22603
  • /115

    $499,999

    • 5 Beds
    • 3 Baths
    • 2,080 Sq Ft

    419 Summit Ave, Winchester, VA 22601

    Welcome Home!This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and granite countertops in the kitchen, this home combines style and functionality. A new roof adds peace of mind, and the fully finished lower level provides additional living space for relaxation or entertainment.With 5

    Waqas Abbasi Lifestyle Realty, LLC.

    419 Summit Ave, Winchester, VA 22601
  • /46

    $499,400

    • 3 Beds
    • 4 Baths
    • 3,359 Sq Ft

    227 Miller St, Winchester, VA 22601

    Charming Downtown Winchester Home with Four Finished Levels. Welcome to 227 Miller Street, where timeless character and abundant living space come together in the heart of downtown Winchester. This inviting 3-bedroom, 4-bathroom home offers four fully finished levels that radiate warmth, comfort, and a true sense of home. Step onto the spacious covered front porch, a perfect spot to enjoy your

    Leah Marabella Realty ONE Group Old Towne

    227 Miller St, Winchester, VA 22601
  • /50

    $555,000

    • 4 Beds
    • 4.5 Baths
    • 3,076 Sq Ft

    107 Okeefe Dr, Winchester, VA 22602

    Carpeting has been replaced with rich hardwood flooring on main level. 2020 New HVAC & Roof & Hot Water Heater & Foyer Pladian Window. This amazing home features a newly renovated kitchen (2023) that you will fall in love with. Talk about gourmet, It's a chef's dream come true featuring a gas cooking range, Silestone counters, a coffee bar, (featuring a butcher block), a huge island, built in

    Cynthia Butler Samson Properties

    107 Okeefe Dr, Winchester, VA 22602
  • /42

    $479,900

    • 4 Beds
    • 1.5 Baths
    • 1,932 Sq Ft

    420 W Cork St, Winchester, VA 22601

    Discover the perfect blend of historic charm and modern convenience at 420 W Cork Street. This captivating four-level brick home offers 4 bedrooms and 1.5 baths, boasting beautiful hardwood floors, gorgeous trim and plenty of space for you and yours. The main level offers a spacious living room, dining room and kitchen. Upstairs you will find 4 sizable bedrooms and a full bath. The top level is a

    Dan Whitacre Colony Realty

    420 W Cork St, Winchester, VA 22601
  • /94

    $545,000

    • 4 Beds
    • 3.5 Baths
    • 2,976 Sq Ft

    2812 Ridgetop Ct, Winchester, VA 22601

    HUGE PRICE IMPROVEMENT! Welcome to this beautiful "picture perfect" brick front 4-bedroom, 3.5-bath home in the desirable Rolling Hills community of Winchester, VA. Perfectly located at the end of a cul-de-sac in an established (and sought after) neighborhood, this one-owner property has been meticulously maintained and is ready for its next chapter.Inside, you’ll find a spacious and inviting

    Sara Duncan RE/MAX Distinctive Real Estate

    2812 Ridgetop Ct, Winchester, VA 22601
  • /42

    $479,900

    • 3 Beds
    • 2.5 Baths
    • 1,976 Sq Ft

    703 National Ave, Winchester, VA 22601

    Fully renovated in 2025, this 3-bedroom, 2.5-bath home is ideally located within Winchester city limits—just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment, as well as Jim Barnett Park for outdoor recreation. Thoughtful updates and fresh landscaping enhance its curb appeal. Inside, you’ll find brand-new bathrooms with updated lighting, vanities,

    Jennifer Sacco RE/MAX Roots

    703 National Ave, Winchester, VA 22601
  • /17

    $389,990 Open Sun 1PM - 3PM

    • 3 Beds
    • 3.5 Baths
    • 1,658 Sq Ft

    TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601

    ***OFFERING UP TO $7K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** CONTACT SALES CONSULTANT FOR DETAILS* Featuring Bedford II in Valor Crossing! Open concept kitchen located next to the country kitchen and living room. Optional features include box bay rear window and 10' x 14' deck. Primary suite with large walk-in closet, dual vanity, and oversized

    Brittany Newman DRB Group Realty, LLC

    TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601
  • /32

    $474,500

    • 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 throughout Renovated kitchen and bath Updated fixtures and finishes Clean, move-in ready condition This home offers the perfect

    Cherish Green Coldwell Banker Elite

    201 Parkway St, Winchester, VA 22601
  • /28

    $475,000

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

    386 Round Hill Rd, Winchester, VA 22602

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

    Bridget Aikens Colony Realty

    386 Round Hill Rd, Winchester, VA 22602
  • /72

    $494,900 Open Sun 12PM - 3PM

    • 5 Beds
    • 3.5 Baths
    • 3,330 Sq Ft

    118 Russelcroft Rd, Winchester, VA 22601

    Tina Jacobin Main Street Realty

    118 Russelcroft Rd, Winchester, VA 22601
  • /21

    $389,880 Open Sun 12PM - 4PM

    • 3 Beds
    • 4 Baths
    • 1,989 Sq Ft

    117 Boone Ct, Winchester, VA 22602

    Immediate Move-in at Rossum Crossing! Winchester's newest and most popular townhome community, conveniently located near shopping and dining options. The St. Paul Townhome features three bedrooms, two and a half baths, and a one-car garage. The main floor boasts an open-concept floor plan, with a spacious family room that flows into a fully equipped kitchen. The kitchen includes an island, a

    Dorelba Estrada New Home Star Virginia, LLC

    117 Boone Ct, Winchester, VA 22602
  • /6

    $225,000

    • Land
    • 15 Acres
    • $15,000 per Acre

    0 N Frederick Pike Unit VAFV2038096, Winchester, VA 22603

    Just 7 miles/minutes from Winchester Medical Center and 10 miles from downtown Winchester, this 15-acre parcel offers privacy and convenience in one. The land features rolling hills, unlogged mature hardwood forest, and mountain views, with a gravel driveway crossing a private bridge into a secluded, untouched setting. Zoned residential, agricultural, and potentially commercial, it’s ideal for

    Kristina Towns Weichert Realtors - Blue Ribbon

    0 N Frederick Pike Unit VAFV2038096, Winchester, VA 22603
  • /51

    $1,115,000

    • 7 Beds
    • 4.5 Baths
    • 4,180 Sq Ft

    207 Westview Dr, Winchester, VA 22603

    Welcome to 207 Westview Drive, a secluded sanctuary nestled on just over six wooded acres in the heart of the Shenandoah Valley—mere minutes from the charm of Historic Old Town Winchester. With over 6,600 square feet of beautifully finished living space, this one-of-a-kind property offers the perfect blend of luxury, comfort, and natural beauty. Tucked deep into the trees, yet close to shops,

    Carolyn Young Samson Properties

    207 Westview Dr, Winchester, VA 22603
  • /3

    $3,200,000

    • Land
    • 8.65 Acres
    • $369,942 per Acre

    0 0 Northwestern Pike, Winchester, VA 22602

    Prime opportunity on 13.05 acres in an unbeatable high-visibility location along Route 50 in Winchester, VA. Positioned directly across from major retailers and conveniences—including Walmart, Sheetz, Tractor Supply, Applebee’s, Dunkin’, Bojangles, and the Winchester Medical Center campus—this property offers exceptional exposure and accessibility. Zoned for multiple development possibilities,

    Sarah Reynolds Keller Williams Realty

    0 0 Northwestern Pike, Winchester, VA 22602
  • /2

    $84,900

    • Land
    • 3 Acres
    • $28,300 per Acre

    0 White Pine Ln, Back Creek, VA 22602

    Discover the perfect canvas for your dream home on this expansive 3-acre parcel of land. Nestled in a serene setting, this property offers ample space for your vision, whether it's a cozy retreat or a sustainable homestead. Enjoy the freedom to design your ideal outdoor living spaces, gardens, or recreational areas, all while being surrounded by nature's beauty. With no restrictive association

    Sharon Daniels Coldwell Banker Premier

    0 White Pine Ln, Back Creek, VA 22602
  • /26

    $299,990

    • 3 Beds
    • 1 Bath
    • 1,205 Sq Ft

    627 Watson Ave, Winchester, VA 22601

    CLASSIC CHARM MEETS CONTEMPORARY COMFORT IN THIS FANTASTIC DUPLEX UNIT! This charming Winchester duplex unit seamlessly blends timeless character with modern conveniences, offering the perfect balance of historic flair and contemporary living. Nestled just minutes from the vibrant heart of downtown Winchester, this inviting property combines an unbeatable location with a thoughtfully-updated

    Kristin Crosby Samson Properties

    627 Watson Ave, Winchester, VA 22601
  • /19

    $325,000

    • 4 Beds
    • 1.5 Baths
    • 1,659 Sq Ft

    728 Green St, Winchester, VA 22601

    This spacious rancher is ideal for someone looking to add their personal touch on a home! With some updates needed, the canvas is ready for you to add some fresh paint and new flooring to bring new life into this home! It does feature a charming brick fireplace, oversized living room, formal dining area, and spacious bedrooms. You'll also notice upgrades to the kitchen along with a newer roof.

    Gavin Washington Weichert Realtors - Blue Ribbon

    728 Green St, Winchester, VA 22601
  • /42

    $849,990 Open Sun 2PM - 4PM

    • 5 Beds
    • 4.5 Baths
    • 5,254 Sq Ft

    1504 Brookdale Ct, Winchester, VA 22601

    This home generates income from solar energy sales averaging over $2k a year! The Solar panels and system are OWNED by the homeowner NOT leased. There are no monthly fees or payments for the system. System is “Grandfathered” with a licensing agreement that allows homeowner to sell excess electricity produced. Lower your energy costs and receive cash earnings! Recent updates over $40k in this

    Julie Shiley Coldwell Banker Realty

    1504 Brookdale Ct, Winchester, VA 22601
  • /16

    $279,900

    • 3 Beds
    • 1.5 Baths
    • 1,332 Sq Ft

    2901 Sorrell Ct, Winchester, VA 22601

    *Investor Opportunity, current tenants have a lease until May of 2027* Welcome to your new home! This beautifully maintained 3 -bedroom, 1.5 bath townhome offers comfort, convenience, and style in a great location. On the main level you will find a spacious kitchen with ample cabinetry and a breakfast area, the living room offers plenty of natural light, off the living room is a convenient half

    Amber Jenkins Century 21 Redwood Realty

    2901 Sorrell Ct, Winchester, VA 22601

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