Winchester, VA Homes

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  $1,250,000 Under Contract

  • Studio
  • 8,616 Sq Ft

  202 S Washington St, Winchester, VA 22601

  Back on the market due to NO fault of the Seller! Currently a single family home with a private “guest apartment”, but zoned multi-family with the potential for up to 4 units and potentially $4000.00+ in monthly rental income! Fantastic opportunity! The private guest suite currently has 2 bedrooms. The 3rd floor also has an additional 2 bedrooms, full bathroom and could laundry room that

  

  Lori Bales

  Keller Williams Realty

  (540) 917-5619

  202 S Washington St, Winchester, VA 22601
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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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  /36

  $375,000 Sold Aug 07, 2025

  • 1,800 Sq Ft
  • $208/SF
  • 4 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1900

  511 S Kent St, Winchester, VA 22601

  Live in downtown in this recently renovated turn of the century charmer. A short walk to the historic walking mall with all of its activities and amenities. Enjoy the original high main floor ceilings, spacious living/family room, open floor plan with the original staircase. The 2022 renovations included all new kitchen with closet pantry, bathrooms, electrical, HVAC (and service ducts),

  Lawrence Lessin Homes By Owner, Inc.

  511 S Kent St, Winchester, VA 22601
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  /43

  Est $434,835 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,190 Sq Ft

  512 Lanny Dr, Winchester, VA 22601

  512 Lanny Dr, Winchester, VA 22601
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  /50

  $749,000 Open Sun 1PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 5,802 Sq Ft

  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

  (540) 802-5378

  1205 Caroline St, Winchester, VA 22601
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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

  $585,999 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,571 Sq Ft

  720 Beehive Way, Winchester, VA 22601

  Welcome to Your Dream Home!Step into this beautifully updated 4-bedroom, 3.5-bath Colonial, ideally situated in one of the most sought-after neighborhoods off Cedar Creek Grade. With spacious living areas, thoughtful updates, and timeless charm, this home offers the perfect blend of comfort and style.At the heart of the home is a stunning open-concept kitchen, complete with brand-new

  Amy Emerson-Kerns Cambridge Premier Realty, LLC.

  720 Beehive Way, Winchester, VA 22601
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  /37

  Est $427,003 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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  /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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  /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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  /47

  $525,000 Sold Aug 01, 2025

  • 1,865 Sq Ft
  • $282/SF
  • 42 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1941

  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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  /20

  Est $445,348 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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  /8

  $690,000

  • 4 Beds
  • 2.5 Baths
  • 3,108 Sq Ft

  1950 Melvor Ln, Winchester, VA 22601

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  Kim Kroner

  Washington Dulles Real Estate Group

  (540) 453-8579

  1950 Melvor Ln, Winchester, VA 22601
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  /13

  $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 area’s 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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  /68

  $635,000 Sold Aug 01, 2025

  • 2,639 Sq Ft
  • $241/SF
  • 22 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2009

  800 Kennedy Dr, Winchester, VA 22601

  Welcome to 800 Kennedy Drive, a spacious Colonial by Richmond American Homes located in the desirable Rolling Hills Estates. This home offers three finished levels with a smart, open layout—perfect for everyday living and entertaining. The main level flows seamlessly from room to room, featuring beautiful hardwood floors and fresh new carpet throughout. The large family room, featuring a stone

  Cindy Greenya Keller Williams Realty

  800 Kennedy Dr, Winchester, VA 22601
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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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  /53

  $633,000

  • 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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  /23

  $1,995 per month

  • 3 Beds
  • 2.5 Baths
  • 1,752 Sq Ft
  • Townhouse for Rent

  2056 Cidermill Ln, Winchester, VA 22601

  Charming 3 bed/2.5 bath townhouse in desirable Orchard Hill. As you enter the house, you will be met with a beautifully updated eat-in kitchen that boasts granite counter tops, two pantries, and a lovely bay window overlooking the front yard. Continue down the hall to your formal dining room which could also be a great place to set up a home office! At the end of the hall, you will enter a cozy

  Rebecca Sims Century 21 Redwood Realty

  2056 Cidermill Ln, Winchester, VA 22601
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  /71

  $1,025,000 Sold Aug 01, 2025

  • 6,517 Sq Ft
  • $157/SF
  • 36 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 1863

  331 N Braddock St, Winchester, VA 22601

  This circa 1863 Italianate home is located in the heart of Winchester's historic district within a short walk to Handley Library and downtown. The home has been elegantly restored, blending timeless charm with modern comforts. The interior is restored to its original grandeur with high ceilings, hardwood floors, decorative moldings, and fireplaces in every room. Fully updated gourmet kitchen with

  John Schroth Colony Realty

  331 N Braddock St, Winchester, VA 22601
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  /17

  Est $269,581 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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  /9

  $225,000 Under Contract

  • Land
  • 6 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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  /22

  $1,799 - $2,231 per month

  Meadow Branch Luxury Apartments

  1 - 2 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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  /49

  $649,000 Sold Jul 31, 2025

  • 3,591 Sq Ft
  • $181/SF
  • 9 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1956

  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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  /36

  Not Listed For Sale

  • Studio
  • 3,790 Sq Ft

  912 S Braddock St, Winchester, VA 22601

  912 S Braddock St, Winchester, VA 22601
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  /8

  $225,000 Under Contract

  • Land
  • 6 Acres
  • $40,761 per Acre

  Lot 6 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 6 Cedar Creek Grade, Winchester, VA
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  /10

  $1,399 per month

  • 2 Beds
  • 1 Bath
  • 6,578 Sq Ft
  • Townhouse for Rent

  209 E Whitlock Ave, Winchester, VA 22601

  Charming Renovated Townhome in the Heart of Downtown Winchester!This beautifully updated 2-bedroom, 1-bath townhome offers the perfect blend of historic charm and modern convenience. Featuring a fresh renovation throughout, the home boasts a stylish kitchen with new appliances, updated cabinetry, and a bright, open living space. Upstairs, you'll find two spacious bedrooms and a modern full

  Amy Emerson-Kerns Cambridge Premier Realty, LLC.

  209 E Whitlock Ave, Winchester, VA 22601
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  /24

  $242,500 Sold Jul 30, 2025

  • 1,080 Sq Ft
  • $225/SF
  • 19 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1986

  208 Kimberly Way, Winchester, VA 22601

  Just Listed in Winchester, VA!A beautifully maintained 2-bedroom, 2.5-bath townhome. Offering 1,080 square feet of comfortable living space. This property combines small-town charm with functional features that make everyday living a breeze. Inside, a bright and airy living room and kitchen welcomes you with large windows and an exit door to the deck that allow natural light to pour in,

  Janet Smith NextHome Realty Select

  208 Kimberly Way, Winchester, VA 22601
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  /49

  Est $413,147 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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  /42

  $344,900

  • 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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  /46

  $1,775 - $2,355 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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  /32

  $390,000 Sold Jul 30, 2025

  • 2,124 Sq Ft
  • $184/SF
  • 27 Days On Market

  • Studio
  • Built 1930

  619 S Cameron St, Winchester, VA 22601

  **Attention Investors** Located on Historic Cameron Street just 5 blocks from from the Winchester Walking Mall with all of its restaurants, shops, and entertainment, this quaint 1930's home has been converted to two income producing apartments. Both apartments are currently leased on a month to month basis with tenants that would be interested in staying on. Each unit is one bedroom and one

  Jim Shebest Coldwell Banker Realty

  619 S Cameron 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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  /44

  $850,000

  • 5 Beds
  • 4.5 Baths
  • 6,122 Sq Ft

  939 Buckner Dr, Winchester, VA 22601

  Listed well below market value, this stunning all-brick home in the sought-after Meadow Branch community was built in 2000 and has undergone extensive renovations in 2023 and 2024. The main-level bedroom includes a spacious, newly updated ensuite featuring an oversized marble-tiled shower, dual vanities, and a custom walk-in closet designed by ClosetsByDesign. The beautifully reimagined kitchen

  Kiran K. Morzaria Parekh Redfin Corporation

  939 Buckner Dr, Winchester, VA 22601
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  /26

  $1,950 per month

  • 3 Beds
  • 1.5 Baths
  • 980 Sq Ft
  • House for Rent

  1309 Commerce St, Winchester, VA 22601

  This charming 3-bedroom, 1.5-bathroom home in the heart of Winchester offers comfort, character, and a prime location. Inside, you’ll find freshly painted walls, hardwood floors, new windows, a brand-new HVAC system, and updated electrical throughout. The home also features a basement with plenty of storage space and a washer and dryer for added convenience. The layout is both functional and

  James King RE/MAX Roots

  1309 Commerce St, Winchester, VA 22601
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  /45

  $515,000 Sold Jul 29, 2025

  • 1,881 Sq Ft
  • $274/SF
  • 15 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1965

  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

  331 Ridge Ave, Winchester, VA 22601
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  /19

  Est $439,568 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
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  /2

  $399,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,394+ Sq Ft

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

  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' 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
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  /50

  $1,785 - $3,144 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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  /18

  $330,000 Sold Jul 28, 2025

  • 1,202 Sq Ft
  • $275/SF
  • 0 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1830

  411 N Loudoun St Unit 104, Winchester, VA 22601

  Just minutes from the walking mall and the charming shops and restaurants of downtown Winchester, this fantastic two-story condo offers the perfect blend of historic character and modern comfort.Step inside to find beautiful hardwood floors and stylish finishes throughout. The fully equipped kitchen features rich dark cabinetry, granite countertops, gas cooking, and a spacious peninsula that

  Lori Bales Keller Williams Realty

  411 N Loudoun St Unit 104, Winchester, VA 22601
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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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