Shepherdstown, WV Homes

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  $130,000

  • Land
  • 2.07 Acres
  • $62,802 per Acre

  Unnumbered Lot Ledge Shepherd Ln, Shepherdstown, WV 25443

  Scenic 2.07-Acre Residential Raw Land Homesite in Shepherdstown Discover the perfect blend of privacy, location, and opportunity with this 2.07-acre residential vacant lot tucked just off Shepherd Lane in Shepherdstown, West Virginia. Set within an established neighborhood of well-spaced homes, this rolling, wooded parcel offers an ideal setting for a custom home surrounded by nature while

  

  Tara Lowe

  Samson Properties

  (304) 396-1522

  Unnumbered Lot Ledge Shepherd Ln, Shepherdstown, WV 25443
• Explore Shepherdstown

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  $2,200 per month

  • 2 Beds
  • 1.5 Baths
  • 1,080 Sq Ft
  • House for Rent

  6860 Engle Molers Rd, Shepherdstown, WV 25443

  This cozy, furnished 2 bedroom rental is just minutes from downtown Shepherdstown. The main level of the property features a large 2 car garage. Keep your cars and yourself out of the weather. Upstairs you have a spacious living room. Built-ins add lots of charm and storage. The kitchen features stainless steel appliances. You have a nice dining space with access to the large deck. What a

  

  Matt Ridgeway

  RE/MAX Real Estate Group

  (304) 648-4432

  6860 Engle Molers Rd, Shepherdstown, WV 25443
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  $565,000 Sold Mar 18, 2025

  232 Southpaw Ln, Shepherdstown, WV 25443

  • 3 Beds
  • 2 Baths
  • 2,029 Sq Ft
  • Built 2004

  Last Sold Summary

  • $278/SF
  • 80 Days On Market

  Current Estimated Value $566,491

  Last Listing Agent Errika Best Greentree Associates of Shepherdstown, Inc.

  232 Southpaw Ln, Shepherdstown, WV 25443
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  Not Listed For Sale

  245 Lyon Ridge Rd, Shepherdstown, WV 25443

  • 5 Beds
  • 3 Baths
  • 2,914 Sq Ft
  • Built 2024

  245 Lyon Ridge Rd, Shepherdstown, WV 25443

  Last Sold Summary

  • $166/SF
  • 68 Days On Market

  Last Sold Price $484,990

  Last Listing Agent Kathleen Cassidy DRH Realty Capital, LLC.
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  $649,900 Under Contract

  • 4 Beds
  • 4 Baths
  • 3,060 Sq Ft

  150 Morgana Dr, Shepherdstown, WV 25443

  This all-brick colonial is a true classic. It sits of over 3 and 1/2 acres of Jefferson County's finest land. Your large lot is surrounded with trees for tons of privacy. Once you clear the trees on your long driveway you will be taken away by this home's curb appeal. A beautiful concrete path leads you from the driveway, passed the manicured landscaping, to the lovely front porch. Can't you just

  

  Matt Ridgeway

  RE/MAX Real Estate Group

  (304) 898-1658

  150 Morgana Dr, Shepherdstown, WV 25443
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  $1,780 per month

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Condo for Rent

  340 W German St Unit 340 W German, Shepherdstown, WV 25443

  This spacious 3 bedroom, 2 1/2 bath duplex has beautiful SPC flooring throughout, and ceramic tile flooring in the upstairs bathrooms. It features a washer and dryer, central heating and A/C, electric oven, dishwasher, and fridge. The Master Bedroom has an expansive walk-in closet and full bath. The other two bedrooms have large closets, and share a full bathroom upstairs, while the half-bath is

  340 W German St Unit 340 W German, Shepherdstown, WV 25443
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  $400,000 Sold Feb 10, 2026

  8709 Shepherdstown Pike, Shepherdstown, WV 25443

  • 2 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1920

  Last Sold Summary

  • 11% Below List Price
  • $261/SF
  • 47 Days On Market

  Current Estimated Value $445,001

  Last Listing Agent Nadine Kennedy Coldwell Banker Premier

  8709 Shepherdstown Pike, Shepherdstown, WV 25443
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  Est $319,032 Not Listed For Sale

  31 Swearingen Way, Shepherdstown, WV 25443

  • 3 Beds
  • 2.5 Baths
  • 2,220 Sq Ft
  • Built 2008

  31 Swearingen Way, Shepherdstown, WV 25443

  Last Sold Summary

  • 1% Above List Price
  • $142/SF
  • 81 Days On Market

  Last Sold Price $316,000

  Last Listing Agent Liz McDonald Dandridge Realty Group, LLC
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  $425,000

  • 4 Beds
  • 2 Baths
  • 2,048 Sq Ft

  207 W High St, Shepherdstown, WV 25443

  Welcome to 207 W High Street located in beautiful and historic Shepherdstown, West Virginia. With Shepherdstown being established in 1762 and one of the oldest towns in West Virginia, this 1790 built home plays a strong role in the community and holds historical significance. The Shepherdstown Historic District was established and added to the National Register of Historic Places in 1973, with a

  Dana Ashlock Samson Properties

  207 W High St, Shepherdstown, WV 25443
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  $1,900 per month

  • 4 Beds
  • 2.5 Baths
  • 1,600 Sq Ft
  • House for Rent

  115 Swearingen Way, Shepherdstown, WV 25443

  3 BR, 2 1/2 bath interior townhouse in Colonial Hills Subdivision close to town and across from Morgan's Grove Park. Tall ceilings, open floor plan, clean and ready to occupy. All electric heat and air, master bedroom suite with walk in closet, breakfast room off kitchen, carpet through out LR, FR and BR, vinyl in kitchen and baths, separate laundry in lower level, and 1 car garage. Potential for

  Brad Lewis Greentree Associates of Shepherdstown, Inc.

  115 Swearingen Way, Shepherdstown, WV 25443
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  $110,000 Sold Jan 27, 2026

  0 Comstock Dr Unit WVBE2042662, Shepherdstown, WV 25443

  • Land
  • 2.61 Acres
  • $42,146 per Acre

  Last Sold Summary

  • 21% Below List Price
  • 163 Days On Market

  Last Listing Agent Eric Exline Roger Fairbourn Real Estate LLC

  0 Comstock Dr Unit WVBE2042662, Shepherdstown, WV 25443
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  Est $853,366 Not Listed For Sale

  200 Summit Crest Ln, Shepherdstown, WV 25443

  • 4 Beds
  • 4.5 Baths
  • 3,293 Sq Ft
  • Built 2005

  200 Summit Crest Ln, Shepherdstown, WV 25443

  Last Sold Summary

  • 2% Above List Price
  • $255/SF
  • 108 Days On Market

  Last Sold Price $839,000

  Last Listing Agent Jennifer Fortson Charis Realty Group
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  /31

  $417,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,906 Sq Ft

  Deerfield Plan at Tollhouse Woods, Shepherdstown, WV 25443

  The Deerfield is a thoughtfully designed two-story house with four bedrooms and two-and-a-half baths. The kitchen features a walk-in pantry and island. That island includes a sink, making it perfect for food preparation, and has plenty of room for stools, so you can entertain. The kitchen looks out over the open-concept dining area and great room. All four bedroom are upstairs along with the

  D.R. Horton Builder

  19 Tollhouse Way Unit 36203408, Shepherdstown, WV 25443
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  $800 per month

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

  114 S Princess St Unit 5, Shepherdstown, WV 25443

  Cute third floor, one bedroom, one bath apartment with separate living room. Walk to Shepherd University or many other downtown destinations. Building main entrance secured with key pad entry.

  Val Nicole Clark Realty FC, LLC

  114 S Princess St Unit 5, Shepherdstown, WV 25443
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  $395,000 Sold Apr 09, 2025

  99 Wildflower Ln, Shepherdstown, WV 25443

  • 4 Beds
  • 2 Baths
  • 1,670 Sq Ft
  • Built 1974

  Last Sold Summary

  • $237/SF
  • 57 Days On Market

  Last Listing Agent BRADEN MILLER ERA Oakcrest Realty, Inc.

  99 Wildflower Ln, Shepherdstown, WV 25443
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  Est $196,338 Not Listed For Sale

  114 College St, Shepherdstown, WV 25443

  • 1 Bed
  • 1 Bath
  • 740 Sq Ft
  • Built 1900

  114 College St, Shepherdstown, WV 25443

  Last Sold Summary

  • 15% Above List Price
  • $230/SF
  • 3 Days On Market

  Last Sold Price $170,000

  Last Listing Agent Wendy Williams Greentree Associates of Shepherdstown, Inc.
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  $574,900 Under Contract

  • 4 Beds
  • 2 Baths
  • 3,582 Sq Ft

  7765 Martinsburg Pike, Shepherdstown, WV 25443

  Experience the charm of this immaculately preserved 1912 stone house, set on over 2 acres in close proximity to historic Shepherdstown. This spacious 4-bedroom, 2-bathroom home features tall ceilings, hardwood floors, and a wide center hall on the main level. You'll also find two large bedrooms, a study, a cozy living room, a full bath, and a convenient laundry area. At the back of the home, the

  Bill Dixon Dandridge Realty Group, LLC

  7765 Martinsburg Pike, Shepherdstown, WV 25443
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  $508,490 Sold Aug 11, 2025

  43 Open Gate Ln, Shepherdstown, WV 25443

  • 4 Beds
  • 3 Baths
  • 2,401 Sq Ft
  • Built 2025

  Last Sold Summary

  • $212/SF
  • 0 Days On Market

  Last Listing Agent Justin Wood D.R. Horton Realty of Virginia, LLC

  43 Open Gate Ln, Shepherdstown, WV 25443
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  Est $565,590 Not Listed For Sale

  277 Shveda Way, Shepherdstown, WV 25443

  • 4 Beds
  • 3 Baths
  • 2,144 Sq Ft
  • Built 2018

  277 Shveda Way, Shepherdstown, WV 25443

  Last Sold Summary

  • 17% Above List Price
  • $226/SF
  • 84 Days On Market

  Last Sold Price $485,000

  Last Listing Agent Anthony Herbert Roberts Realty Group, LLC
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  $649,900 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,345 Sq Ft

  63 Hackberry Cir, Shepherdstown, WV 25443

  Nestled just minutes from the heart of historic Shepherdstown, this home offers the charm of small town living with unbeatable convenience. Known for its vibrant arts scene, cozy cafes, local boutiques and one of the oldest universities in the country, Shepherdstown has a warmth and culture all its own. Home to Shepherd University; a vibrant campus with many events including theatre events, art

  Laurel Murray Samson Properties

  63 Hackberry Cir, Shepherdstown, WV 25443
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  $975,000 Sold Jul 01, 2025

  115 Windward Ln, Shepherdstown, WV 25443

  • 5 Beds
  • 5 Baths
  • 5,778 Sq Ft
  • Built 1974

  Last Sold Summary

  • $169/SF
  • 74 Days On Market

  Current Estimated Value $989,239

  Last Listing Agent Tracy Palmer Samson Properties

  115 Windward Ln, Shepherdstown, WV 25443
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  Est $644,971 Not Listed For Sale

  224 Shveda Way, Shepherdstown, WV 25443

  • 4 Beds
  • 4 Baths
  • 2,860 Sq Ft
  • Built 2018

  224 Shveda Way, Shepherdstown, WV 25443

  Last Sold Summary

  • 3% Above List Price
  • $219/SF
  • 52 Days On Market

  Last Sold Price $625,000

  Last Listing Agent Robert Krop Keller Williams Realty Centre
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  $589,000 Under Contract

  • 6 Beds
  • 4.5 Baths
  • 4,829 Sq Ft

  23 Green Meadow Cir, Shepherdstown, WV 25443

  Located in sought-after Shepherdstown, this stunning colonial with striking stone accents truly has it all. Tucked away on a quiet cul-de-sac, the spacious, move-in-ready home offers 6 bedrooms and 4 full baths on a generous 3⁄4-acre lot. A side-load two-car garage and inviting covered front porch set the tone before you even step inside. The interior shines with gleaming hardwood floors, a

  Michael Oates Exit Success Realty

  23 Green Meadow Cir, Shepherdstown, WV 25443
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  $389,990 Sold Oct 29, 2025

  55 Open Gate Ln, Shepherdstown, WV 25443

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $177/SF
  • 28 Days On Market

  D.R. Horton Tollhouse Woods

  55 Open Gate Ln, Shepherdstown, WV 25443
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  Est $756,439 Not Listed For Sale

  214 W German St, Shepherdstown, WV 25443

  • 7 Beds
  • 2.5 Baths
  • 3,168 Sq Ft
  • Built 1776

  214 W German St, Shepherdstown, WV 25443

  Last Sold Summary

  • 4% Below List Price
  • $248/SF
  • 5 Days On Market

  Last Sold Price $785,000

  Last Listing Agent Dan Anderson Greentree Associates of Shepherdstown, Inc.
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  $497,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,511 Sq Ft

  Hayden Plan at Tollhouse Woods, Shepherdstown, WV 25443

  The floorplan you love now with a basement! The Hayden is a two-story plan with 5 bedrooms and 3 bathrooms in 2,511 square feet. The main level features a flex room adjacent to the foyer, ideal for a formal dining room or home office. The gourmet kitchen has an oversized island for extra seating and a large pantry, and it opens to the dining area and a spacious living room. A bedroom with a full

  D.R. Horton Builder

  19 Tollhouse Way Unit 36203407, Shepherdstown, WV 25443
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  $160,000 Sold Nov 24, 2025

  39 Nightingale Ln, Shepherdstown, WV 25443

  • 3 Beds
  • 1 Bath
  • 1,656 Sq Ft
  • Built 1975

  Last Sold Summary

  • $97/SF
  • 65 Days On Market

  Current Estimated Value $202,168

  Last Listing Agent Jennifer Largent Compass West Realty, LLC

  39 Nightingale Ln, Shepherdstown, WV 25443
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  Est $538,235 Not Listed For Sale

  97 Heritage Dr, Shepherdstown, WV 25443

  • 4 Beds
  • 3 Baths
  • 2,239 Sq Ft
  • Built 2018

  97 Heritage Dr, Shepherdstown, WV 25443

  Last Sold Summary

  • 2% Below List Price
  • $245/SF
  • 34 Days On Market

  Last Sold Price $549,000

  Last Listing Agent Gregory Graham ERA Liberty Realty
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  $509,900

  • 4 Beds
  • 3.5 Baths
  • 3,684 Sq Ft

  347 Maddex Dr, Shepherdstown, WV 25443

  347 Maddex Drive is the one you have been waiting for. Loved by only 1 owner since it's 2007 build. This beautiful brick front home welcomes you with the quaint sitting area near the front stoop. Hardwood flooring that was refinished a few years ago on almost the entire main level greeting you as soon as you open the front door. BRAND NEW CARPET on the entire upstairs and living room. Freshly

  Brittany Newman Dream Driven Properties, LLC

  347 Maddex Dr, Shepherdstown, WV 25443
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  $590,000 Sold Aug 05, 2025

  72 Rolling Green Ct, Shepherdstown, WV 25443

  • 6 Beds
  • 4.5 Baths
  • 4,416 Sq Ft
  • Built 2007

  Last Sold Summary

  • $134/SF
  • 106 Days On Market

  Current Estimated Value $615,302

  Last Listing Agent Adam Shively Samson Properties

  72 Rolling Green Ct, Shepherdstown, WV 25443
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  Est $360,326 Not Listed For Sale

  262 Old Martinsburg Rd, Shepherdstown, WV 25443

  • 3 Beds
  • 2 Baths
  • 1,796 Sq Ft
  • Built 1968

  262 Old Martinsburg Rd, Shepherdstown, WV 25443

  Last Sold Summary

  • 8% Above List Price
  • $187/SF
  • 6 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Sarah Santacroce Coldwell Banker Premier
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  /78

  $580,000 Under Contract

  • 4 Beds
  • 3.5 Baths
  • 4,128 Sq Ft

  55 Hidden Valley Cir, Shepherdstown, WV 25443

  What a home and property! Nearly one-and-a-half park-like acres in Shepherdstown set the stage for this stately colonial-style home. A fenced rear yard is great for two-legged and four-legged friends and a mixture of mature trees and open spaces in all directions provides a magical and private sensation. Despite this far, far away feeling, modern conveniences are readily at hand. Comcast Xfinity

  Nicholas Palkovic Touchstone Realty, LLC

  55 Hidden Valley Cir, Shepherdstown, WV 25443
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  $600,000 Sold Jul 11, 2025

  60 Reachcliff Dr, Shepherdstown, WV 25443

  • 3 Beds
  • 3 Baths
  • 2,861 Sq Ft
  • Built 2006

  Last Sold Summary

  • $210/SF
  • 9 Days On Market

  Current Estimated Value $610,121

  Last Listing Agent Tara Lowe Samson Properties

  60 Reachcliff Dr, Shepherdstown, WV 25443
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  /85

  Est $699,298 Not Listed For Sale

  106 N Duke St, Shepherdstown, WV 25443

  • 4 Beds
  • 2.5 Baths
  • 2,743 Sq Ft
  • Built 1928

  106 N Duke St, Shepherdstown, WV 25443

  Last Sold Summary

  • 4% Below List Price
  • $266/SF
  • 24 Days On Market

  Last Sold Price $730,000

  Last Listing Agent Mercedes Prohaska Coldwell Banker Premier
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  /54

  $710,000

  • 4 Beds
  • 4.5 Baths
  • 5,497 Sq Ft

  60 Horner Farm Ln, Shepherdstown, WV 25443

  Come tour this fantastic move-in ready home located in Shepherdstown, WV. Boasting 4 bedrooms and 4.5 baths, this property sits on a corner lot with a partially fenced backyard and a new Trex deck. Numerous upgrades include a new upstairs A/C unit, fresh paint throughout all three floors, new basement carpeting, new washer and dryer, and professional landscaping. The main level features hardwood

  Brandon Darr Samson Properties

  60 Horner Farm Ln, Shepherdstown, WV 25443
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  $350,000 Sold Dec 05, 2025

  21 Rock Spring Ln, Shepherdstown, WV 25443

  • 3 Beds
  • 3 Baths
  • 3,480 Sq Ft
  • Built 1986

  Last Sold Summary

  • $101/SF
  • 20 Days On Market

  Current Estimated Value $354,676

  Last Listing Agent Debbie Hugo Samson Properties

  21 Rock Spring Ln, Shepherdstown, WV 25443
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  Est $638,621 Not Listed For Sale

  1899 Trough Rd, Shepherdstown, WV 25443

  • 4 Beds
  • 3 Baths
  • 3,040 Sq Ft
  • Built 1989

  1899 Trough Rd, Shepherdstown, WV 25443

  Last Sold Summary

  • 14% Above List Price
  • $184/SF
  • 48 Days On Market

  Last Sold Price $560,000

  Last Listing Agent Lisa Gill ERA Oakcrest Realty, Inc.
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  $524,900

  • 3 Beds
  • 3 Baths
  • 2,446 Sq Ft

  200 Meadow Ridge Dr, Shepherdstown, WV 25443

  PRICE IMPROVEMENT...A MID WINTER OPPORTUNITY! In Cress Creek’s coveted golf community, opportunities like this almost never appear. Only three double villas were ever built here — and the last one sold nearly a decade ago. Now, one of these rare homes is finally available, perfectly positioned on a beautiful .344‐acre lot with sweeping golf course views. Inside, sunlight fills the

  Paula Miller Coldwell Banker Premier

  200 Meadow Ridge Dr, Shepherdstown, WV 25443
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  $300,000 Sold Oct 30, 2025

  838 Billmyer Mill Rd, Shepherdstown, WV 25443

  • 2 Beds
  • 1 Bath
  • 1,658 Sq Ft
  • Built 1968

  Last Sold Summary

  • $181/SF
  • 102 Days On Market

  Current Estimated Value $320,740

  Last Listing Agent Densil Nibert Nibert Realty & Auctions, LLC

  838 Billmyer Mill Rd, Shepherdstown, WV 25443
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  Est $661,779 Not Listed For Sale

  101 N Princess St, Shepherdstown, WV 25443

  • 3 Beds
  • 2 Baths
  • 2,350 Sq Ft
  • Built 1793

  101 N Princess St, Shepherdstown, WV 25443

  Last Sold Summary

  • 12% Below List Price
  • $319/SF
  • 4 Days On Market

  Last Sold Price $750,000

  Last Listing Agent Dan Anderson Greentree Associates of Shepherdstown, Inc.

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