Winchester County, VA Homes

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  /50

  $749,000 Pending

  • 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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  /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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  /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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  /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
• 

  

  /2

  $279,000 Coming Soon

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

  423 Highland Ave, Winchester, VA 22601

  Charming Winchester Home –Don't let this property slip away!This freshly updated home in the heart of Winchester offers incredible potential and versatility. Featuring off-street parking from the rear alley, a fresh coat of paint, and newly installed vinyl flooring downstairs, this property is move-in ready while leaving room for your personal touches.Highlights include:3

  

  Carlos Soares

  Samson Properties

  (540) 584-8746

  423 Highland Ave, 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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  /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
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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

  $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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  /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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  /30

  $380,000 Sold Sep 04, 2025

  • 1,431 Sq Ft
  • $266/SF
  • 31 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2004

  1826 Kershaw Ln, Winchester, VA 22601

  This charming one-level home is perfectly situated in one of Winchester's desirable 55+ senior communities, Willow Lawn Cottages. Great home....first time on the market,featuring two spacious bedrooms, two full bathrooms, hardwood floors & vaulted ceilings. The open and inviting floor plan will make your new home ideal for both daily living and entertaining. The large primary suite offers

  Jeff Webber Long & Foster Real Estate, Inc.

  1826 Kershaw Ln, 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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  /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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  /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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  /32

  $400,000 Sold Sep 02, 2025

  • 1,548 Sq Ft
  • $258/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  423 Crescent Dr, Winchester, VA 22601

  This charming one-level ranch is tucked away on a quiet cul-de-sac in the City of Winchester, just minutes from shopping, dining, and all the conveniences of town.Inside, updated hickory hardwood flooring flows throughout the home. The kitchen shines with updates, including new fixtures, quartzite countertops, and a fresh kitchen floor. The bathroom features an ADA-compliant shower, and

  Sharon Farinholt Realty ONE Group Old Towne

  423 Crescent Dr, Winchester, VA 22601
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  /17

  Est $281,035 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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  /43

  $549,900

  • 4 Beds
  • 3 Baths
  • 2,614 Sq Ft

  1729 Handley Ave, Winchester, VA 22601

  This immaculate 4-bedroom, 3-bath Cape Cod in sought-after Meadow Branch is move-in ready and full of thoughtful updates! From the welcoming foyer, the home flows seamlessly into a bright living room, spacious kitchen, and dedicated dining room. On the main level you'll also find two bedrooms and a full bath, perfect for guests or convenient one-level living.From the kitchen, step outside

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 698-5892

  1729 Handley Ave, Winchester, VA 22601
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  /19

  $1,400 per month

  • 2 Beds
  • 1 Bath
  • 8,508 Sq Ft
  • Condo for Rent

  113 W Boscawen St Unit 3, Winchester, VA 22601

  3rd floor walk-up apartment. In the middle of downtown Winchester is this 2 bedroom, 1 bath apartment featuring an abundancy of light with numerous windows, large rooms and hardwood floors. Primary bedroom has direct access to bathroom. Water, sewer and trash pick-up is provided in the monthly rent as is 1 parking space in the Braddock Street Parking Garage. Tenant is responsible for

  Barbara Gaul Jim Barb Realty, Inc.

  113 W Boscawen St Unit 3, Winchester, VA 22601
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  /14

  $338,955 Sold Aug 29, 2025

  • 1,442 Sq Ft
  • $235/SF

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  629 Laurelwood Cir, Winchester, VA 22601

  Fall Move-In Poplar Available at Laurelwood Commons!This home features 3 bedrooms, 2.5 baths, 1,442 sq. ft., upgraded kitchen with white cabinets, quartz counters, island, LVP throughout the main level & more! Plus, enjoy all closing costs paid with use of NVR Mortgage!*. Learn more!

  Ryan Homes

  629 Laurelwood Cir, 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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  /9

  $225,000

  • 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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  /73

  $2,079 - $2,707 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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  /2

  $150,000 Sold Aug 29, 2025

  • 1,678 Sq Ft
  • $89/SF
  • 1 Day On Market

  • 2 Beds
  • 2 Baths
  • Built 1910

  315 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.Property sold AS IS.Access from Jolley Lane and parking in rear of property.

  Sheila Pack RE/MAX Roots

  315 National Ave, Winchester, VA 22601
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  /49

  Est $413,968 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
• 

  

  /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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  /20

  $3,400 per month

  • 2 Beds
  • 2.5 Baths
  • 1,981 Sq Ft
  • Condo for Rent

  210 E Boscawen St Unit 204, Winchester, VA 22601

  This stunning apartment has nearly 2000 sq ft on one level. Just steps from all of the restaurants, night life and events in Old Town Winchester. The historic Winchester Star building has been renovated for luxury living that includes private parking, a rarity downtown. There are two large bedrooms, each with their own en-suite and walk-in closet, ample living and dining spaces, a separate

  Katie Landi Jordan Samson Properties

  210 E Boscawen St Unit 204, Winchester, VA 22601
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  /45

  $410,000 Sold Aug 29, 2025

  • 2,250 Sq Ft
  • $182/SF
  • 3 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2018

  149 Biscane Ct, Winchester, VA 22602

  149 Biscane Ct, where fresh design feels effortlessly like home.. This beautifully maintained 2018 townhome shows like new construction! This spacious, light-filled townhome offers three levels of privacy and is ideal for today’s lifestyle. Let me walk you through your new home! When you pull into the garage, the front facing one-car garage features epoxy floors and wall shelving, ideal

  Kara Koonce Weichert, REALTORS

  149 Biscane Ct, Winchester, VA 22602
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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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  /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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  /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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  /20

  $219,000 Sold Aug 29, 2025

  • 496 Sq Ft
  • $442/SF
  • 62 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1927

  537 Hillman Dr, Winchester, VA 22601

  Update! Mandy is having more work done and will soon be connected to the city sewer system!! TIRED OF DATING? Hi, my name is Amanda. Some friends call me Mandy - and some call me 537 Hillman Drive. I have been working really hard on myself lately, and I think I’m ready for a long-term relationship. I started by covering the basics, like new Luxury Vinyl Plank flooring, ceiling fans, light

  Kristin Crosby Samson Properties

  537 Hillman Dr, Winchester, VA 22601
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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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  $429,340 New Construction

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

  0 Homesite 114 Monteith Dr Unit 36422292, Winchester, VA 22601

  3 Level Townhome With Over 1,600 Finished sq. ft., 1 Car Garage & Rear Deck! Bedford II, 3 level townhome features a partial stone front with 1 car garage. This home features 3 Bedrooms and 3.5 Baths. It is fully finished top to bottom. The front door leads directly into the spacious lower level including 9 ft. ceilings, foyer with a double coat closet, access to the garage with a garage door

  

  DRB Homes

  Builder

  0 Homesite 114 Monteith Dr Unit 36422292, Winchester, VA 22601
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  /32

  $3,100 per month

  • 2 Beds
  • 2 Baths
  • 1,230 Sq Ft
  • Condo for Rent

  210 E Boscawen St Unit 202, Winchester, VA 22601

  This stunning apartment features 9 south facing windows for maximum natural light, just steps from all of the restaurants, night life and events in Old Town Winchester. The historic Winchester Star building has been renovated for luxury living that includes private parking, a rarity downtown. Two large bedrooms, each with their own en-suite and walk-in closet are set apart by the open space

  Katie Landi Jordan Samson Properties

  210 E Boscawen St Unit 202, Winchester, VA 22601
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  /44

  $420,000 Sold Aug 28, 2025

  • 1,324 Sq Ft
  • $317/SF
  • 12 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1945

  567 York Ave, Winchester, VA 22601

  Step into contemporary comfort with this top-to-bottom revamped gem in the heart of Winchester! A welcoming front porch invites you inside to discover sleek matte-black fixtures, new floors, and clean white finishes throughout. The open floor plan effortlessly blends the living room—anchored by a modern built-in fireplace—with a chef-ready kitchen boasting fresh cabinetry, lighting, and stainless

  Mike Webber EXP Realty, LLC

  567 York Ave, Winchester, VA 22601
• 

  

  /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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  /44

  $782,000 Pending

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

  939 Buckner Dr, Winchester, VA 22601

  Priced to se!!! 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

  Kiran K. Morzaria Parekh Redfin Corporation

  939 Buckner Dr, Winchester, VA 22601
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  /46

  $1,820 - $2,760 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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  /13

  $190,000 Sold Aug 28, 2025

  • Land
  • 5 Acres
  • $35,185 per Acre

  • 34 Days On Market

  LOT B 4661 Middle Rd, Winchester, VA 22602

  Prime level 5.4- acre lot approved for a 4-bedroom standard septic system and well. Gently rolling and surrounded by nature, it the perfect canvas for your custom built-home. Don't miss this rare opportunity to own a piece of the country side just minutes from downtown Winchester. Call listing Agent to see property.

  Maureen Cunningham Century 21 Redwood Realty

  LOT B 4661 Middle Rd, Winchester, VA 22602
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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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