Shepherdstown, WV Homes

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  /45

  $487,000 Sold Mar 04, 2025

  • 4,046 Sq Ft
  • $120/SF
  • 37 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2006

  262 Maddex Farm Dr, Shepherdstown, WV 25443

  Home features 5 bedrooms and 3.5 baths with finished basement. Owner added square footage with bump outs and large sun room. The kitchen provides an open concept to informal living areas and private office. Expansive deck off the kitchen provides for great days in the warmer seasons or take the steps down to the concrete patio for the fire pit in the cooler seasons. The finished basement

  Jay Deeds Keller Williams Realty Advantage

  262 Maddex Farm Dr, Shepherdstown, WV 25443
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  /89

  Est $685,214 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,698 Sq Ft

  32 Juniper Dr, Shepherdstown, WV 25443

  32 Juniper Dr, Shepherdstown, WV 25443
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  /11

  $899,000 New Construction

  • 3 Beds
  • 3 Baths
  • 2,334 Sq Ft

  2 Winebrenner Rd, Shepherdstown, WV 25443

  Exceptional custom Cape Cod home is to be built on a scenic, level lot just outside Shepherdstown. It is filled with the kind of quality details that will elevate your living experience. Enter from the covered porch and find a secondary bedroom, bathroom, and a study with double glass doors to your left. The great room ahead features a fireplace and soaring cathedral ceilings, creating a warm and

  Louise McDonald Dandridge Realty Group, LLC

  2 Winebrenner Rd, Shepherdstown, WV 25443
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  /68

  $839,000 Sold Feb 28, 2025

  • 3,293 Sq Ft
  • $255/SF
  • 108 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2005

  200 Summit Crest Ln, Shepherdstown, WV 25443

  Back to active at no fault of sellers This home has for over 6500 square feet. With over 3200 finished sq. ft. this home is an absolute stunning beauty. This ranch style home is set on a 3-acre estate in desirable Shepherdstown, WV. It features 4 bedrooms, 4.5 bathrooms, and a spacious kitchen with a charming breakfast area. The formal dining and living rooms are complemented by a

  Jennifer Fortson Charis Realty Group

  200 Summit Crest Ln, Shepherdstown, WV 25443
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  /32

  Est $578,001 Not Listed For Sale

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

  131 N Tamarac Dr, Shepherdstown, WV 25443

  131 N Tamarac Dr, Shepherdstown, WV 25443
• 

  

  /39

  $622,222 Pending

  • 6 Beds
  • 4.5 Baths
  • 3,300 Sq Ft

  927 Persimmon Ln, Shepherdstown, WV 25443

  NEW PRICE $622,222 | Nestled in the tranquil setting of Shepherdstown, this beautiful Colonial home offers a serene retreat with tons of amenities! Boasting 6 bedrooms and 4.5 bathrooms, it sits on nearly 4 acres of picturesque land. The partially fenced property includes a charming chicken coop, as well as other livestock included areas, perfect for fulfilling your farm dreams. Enjoy leisurely

  Brianna Goetting Pearson Smith Realty, LLC

  927 Persimmon Ln, Shepherdstown, WV 25443
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  /46

  $484,990 Sold Feb 27, 2025

  • 2,914 Sq Ft
  • $166/SF
  • 68 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2024

  245 Lyon Ridge Rd, Shepherdstown, WV 25443

  Quick Move In! Available now in Tollhouse Woods, Shepherdstown's newest community located just a mile from the downtown area and university. This 2 Story single family home marries features and affordability and comes with everything included. 4 Bedrooms, LVP floors in the main living spaces, included kitchen appliances, granite countertops and white cabinets give the updated look you've always

  Kathleen Cassidy D R Horton Realty of Virginia LLC

  245 Lyon Ridge Rd, Shepherdstown, WV 25443
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  /57

  Est $843,299 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,674 Sq Ft

  260 S Tamarac Dr, Shepherdstown, WV 25443

  260 S Tamarac Dr, Shepherdstown, WV 25443
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  /35

  $649,999 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,231 Sq Ft

  21 Steamboat Run Rd, Shepherdstown, WV 25443

  Ready for October 6th 2025 delivery!! Rare opportunity to own a new home with river access in Steamboat Run!! 1.55 +/- acres of level ground. Underground Utilities for your new home. Your home will fit in perfectly and will include the following: 4 bedrooms with 2.5 baths for the ranch craftsman style home. Quality construction with nicely upgraded full kitchen appliance package, granite or

  Rick Boswell Gain Realty

  21 Steamboat Run Rd, Shepherdstown, WV 25443
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  /2

  $45,000 Sold Feb 26, 2025

  • Land
  • 0.48 Acre
  • $93,750 per Acre

  • 186 Days On Market

  0 Mockingbird Ln, Shepherdstown, WV 25443

  .48 Acre lot in Mecklenburg Heights. Close to town. Mockingbird Lane is scheduled to be paved in the fall. Lot is at the end of Mockingbird Lane. Public water access. Septic system install needed.

  Scott Wachtel Path Realty

  0 Mockingbird Ln, Shepherdstown, WV 25443
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  /43

  Est $438,032 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,838 Sq Ft

  341 S Hills Dr, Shepherdstown, WV 25443

  341 S Hills Dr, Shepherdstown, WV 25443
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  /104

  $1,200,000 Pending

  • 5 Beds
  • 2.5 Baths
  • 4,390 Sq Ft

  211 E High St, Shepherdstown, WV 25443

  The Abraham Shepherd Home – A Rare Blend of History, Elegance & Modern ComfortBuilt in 1759, the Abraham Shepherd Home is one of the oldest and most iconic residences in West Virginia. Tucked into the heart of Shepherdstown—West Virginia’s oldest town—this distinguished property offers a seamless blend of historic grandeur and thoughtful modern updates, including rare off-street parking—a

  Meghan Pachas Realty ONE Group Old Towne

  211 E High St, Shepherdstown, WV 25443
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  /42

  $316,000 Sold Feb 20, 2025

  • 2,220 Sq Ft
  • $142/SF
  • 81 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2008

  31 Swearingen Way, Shepherdstown, WV 25443

  $10K PRICE REDUCTION! This brick-front end-unit townhouse is located just outside Historic Shepherdstown in the Colonial Hills community. Featuring three finished levels, the home boasts an open floor plan highlighted by LVP flooring, stainless steel appliances, Corian countertops, and custom plantation shutters. Enjoy outdoor privacy on the rear deck, which overlooks a serene treeline.The

  Liz McDonald Dandridge Realty Group, LLC

  31 Swearingen Way, Shepherdstown, WV 25443
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  /60

  Est $691,103 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,276 Sq Ft

  291 S Hills Dr, Shepherdstown, WV 25443

  291 S Hills Dr, Shepherdstown, WV 25443
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  /7

  $89,900 Pending

  • Land
  • 1.27 Acres
  • $70,787 per Acre

  4004 Scrabble Rd, Shepherdstown, WV 25443

  Build Your Dream Home on 1.27 Acres with Well & Septic Already in Place!Located between historic Shepherdstown and the growing Martinsburg/Spring Mills area, this 1.27-acre lot offers the perfect blend of privacy and convenience. The property is mostly cleared, level, and ready for your custom home. With a well and septic system already installed, much of the prep work is done—saving you

  Chris Ross Samson Properties

  4004 Scrabble Rd, Shepherdstown, WV 25443
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  /65

  $300,000 Sold Feb 10, 2025

  • 2,196 Sq Ft
  • $137/SF
  • 1 Day On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2007

  322 Starkeys Landing, Shepherdstown, WV 25443

  Spacious Three-Story Townhouse with Garage Near Shepherd University! Seller is offering $1,500 toward Buyer's closing costs!This beautifully maintained townhouse offers three finished levels of comfortable living in the sought-after Colonial Hills community, just outside historic Shepherdstown. With an open floor plan, nine-foot ceilings, and bump-outs on every level, this home feels

  Christine Reeder Long & Foster Real Estate, Inc.

  322 Starkeys Landing, Shepherdstown, WV 25443
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  /14

  Est $674,022 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,962 Sq Ft

  451 S Hills Dr, Shepherdstown, WV 25443

  451 S Hills Dr, Shepherdstown, WV 25443
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  /52

  $435,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 4,000 Sq Ft

  467 Maddex Farm Dr, Shepherdstown, WV 25443

  Enjoy all the amenities of a college town, great restaurants and nearby shopping. Shepherdstown College has a Wellness center, with pool and aquatics. Memberships available to Shepherdstown residents. Meanwhile enjoy the quiet Maddex Farm neighborhood with a large well lived in home enjoyed by a large family. Fenced yard for your pets and back yard cook outs. ** Possible VA Assumable loan

  Jeanne Cooper Century 21 Redwood Realty

  467 Maddex Farm Dr, Shepherdstown, WV 25443
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  /32

  $445,500 Sold Jan 29, 2025

  • 2,969 Sq Ft
  • $150/SF
  • 208 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2024

  297 Lyon Ridge Rd, Shepherdstown, WV 25443

  Quick Move In! Available now in Tollhouse Woods, Shepherdstown's newest community located just a mile from the downtown area and universtity. This 2 Story single family home marries features and affordability and comes with everything included. 4 Bedrooms, LVP floors in the main living spaces, included kitchen appliances, granite countertops and white cabinets give the updated look you've always

  Kathleen Cassidy D R Horton Realty of Virginia LLC

  297 Lyon Ridge Rd, Shepherdstown, WV 25443
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  /54

  Est $695,339 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,711 Sq Ft

  168 Meadow Ridge Dr, Shepherdstown, WV 25443

  168 Meadow Ridge Dr, Shepherdstown, WV 25443
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  /31

  $454,990 Pending

  • 4 Beds
  • 2 Baths
  • 2,969 Sq Ft

  166 Riderwood Way, Shepherdstown, WV 25443

  IMMEDIATE Move In! Backs to open space! Walk out Basement w/ finished Rec Room! Located in Downtown Shepherdstown! This property and sits on a flat and spacious homesite, one of the largest in the community! This 2 Story single family home marries features and affordability and comes with everything included. 4 Bedrooms, LVP floors in the main living spaces, included kitchen appliances, granite

  Justin K Wood D.R. Horton Realty of Virginia, LLC

  166 Riderwood Way, Shepherdstown, WV 25443
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  /43

  $339,000 Sold Jan 28, 2025

  • 1,998 Sq Ft
  • $170/SF
  • 12 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1973

  67 Wildflower Ln, Shepherdstown, WV 25443

  Well-maintained split foyer in the desirable river access community of Steamboat Run. This wonderful layout includes two primary bedroom options and two large living spaces to enjoy. The home is set on an acre of land in a tranquil neighborhood that provides river access and picnic grounds, providing a great balance of privacy and community. The home features three bedrooms, plus space for an

  Adam Miller Coldwell Banker Premier

  67 Wildflower Ln, Shepherdstown, WV 25443
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  /36

  Est $321,363 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,235 Sq Ft

  224 Spring Warbler Way, Shepherdstown, WV 25443

  224 Spring Warbler Way, Shepherdstown, WV 25443
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  /28

  $502,490 Pending

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

  165 Riderwood Way, Shepherdstown, WV 25443

  Spacious Corner Lot! Complete with main level bedroom, and finished basement rec room! One of the best lots in the neighborhood, this corner lot property sits on a spacious and very usable walkout homesite. Only a stone's throw away from Morgan's Grove Park Entrance. This 2 Story single family home marries features and affordability and comes with everything included. 5 Bedrooms, LVP floors in

  Justin K Wood D.R. Horton Realty of Virginia, LLC

  165 Riderwood Way, Shepherdstown, WV 25443
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  /88

  $1,750,000 Sold Jan 24, 2025

  • 4,464 Sq Ft
  • $392/SF
  • 117 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1986

  4001 Engle Molers Rd, Shepherdstown, WV 25443

  This stunning Mid-Century Modern home, built in 1986, is sited on 100-acres near historic Shepherdstown, WV, offering unparalleled privacy and a deep connection to nature. Designed by a famous architect, James Wilner, the house features elegant details throughout its 4,464 square feet of interior living space, including 3 spacious downstairs bedrooms, 1 upstairs bedroom, and 3.5 bathrooms. The

  Carolyn Snyder Snyder Bailey & Associates

  4001 Engle Molers Rd, Shepherdstown, WV 25443
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  /92

  Est $567,845 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,663 Sq Ft

  57 Heritage Dr, Shepherdstown, WV 25443

  57 Heritage Dr, Shepherdstown, WV 25443
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  /39

  $399,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,466 Sq Ft

  53 Stonehouse Ln, Shepherdstown, WV 25443

  Welcome to your private retreat in Shepherdstown! Nestled on 2 acres with surrounding area being newly declared protected parkland. This contemporary home is filled with character and architectural charm. The layout features a main-level bedroom and an inviting design that blends beautifully with its natural surroundings. NEW ROOF & NEW SKYLIGHTS in last couple of years. Wildlife and privacy

  Kara Burnett Samson Properties

  53 Stonehouse Ln, Shepherdstown, WV 25443
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  /33

  $419,490 Sold Jan 22, 2025

  • 1,906 Sq Ft
  • $220/SF
  • 75 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2024

  238 Lyon Ridge Rd, Shepherdstown, WV 25443

  Quick Move In! Corner Lot! Located in our Tollhouse Woods community on the edge of Downtown Shepherdstown! This 2 Story single family home marries features and affordability and comes with everything included. 4 Bedrooms, LVP floors in the main living spaces, included kitchen appliances, granite countertops and white cabinets give the updated look you've always wanted. Located next to Morgan's

  Kathleen Cassidy D R Horton Realty of Virginia LLC

  238 Lyon Ridge Rd, Shepherdstown, WV 25443
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  /43

  Est $346,375 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,576 Sq Ft

  8008 Shepherdstown Pike, Shepherdstown, WV 25443

  8008 Shepherdstown Pike, Shepherdstown, WV 25443
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  /32

  $375,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  59 Shade Ln, Shepherdstown, WV 25443

  ***OPEN HOUSE*** Saturday, August 30th from 12-2pm ***OPEN HOUSE*** Enjoy the best of country living in this charming and spacious rancher, perfectly situated on 2.17 acres of scenic land. Featuring 3 bedrooms and 2 full baths, this freshly painted home offers a bright, welcoming atmosphere. The 2-car garage and unfinished basement provide ample storage and room to customize to your needs. Recent

  Ronald Wolfe Charis Realty Group

  59 Shade Ln, Shepherdstown, WV 25443
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  /36

  $310,000 Sold Jan 17, 2025

  • Land
  • 6.1 Acres
  • $50,820 per Acre

  0 Steamboat Run Rd Unit WVJF2015442, Shepherdstown, WV 25443

  Imagine waking up on vacation every day in your home on 800 feet of Potomac River waterfront! These two lots at a bend in the river just north of Shepherdstown, WV, are situated in the sought-after Steamboat Run neighborhood. The sellers planned, perc'ed, and permitted a gorgeously designed dream home on stilts. Life happened, and they are no longer able to build. Their loss is your gain! Use

  Liz McDonald Dandridge Realty Group, LLC

  0 Steamboat Run Rd Unit WVJF2015442, Shepherdstown, WV 25443
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  /43

  Est $602,860 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,972 Sq Ft

  7766 Shepherdstown Pike, Shepherdstown, WV 25443

  7766 Shepherdstown Pike, Shepherdstown, WV 25443
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  /62

  $725,000 Under Contract

  • 4 Beds
  • 4.5 Baths
  • 4,910 Sq Ft

  22 Reachcliff Cir, Shepherdstown, WV 25443

  Welcome home to 22 Reachcliff Circle—a meticulously maintained 4-bedroom, 4.5-bath home in the sought-after Fernbank at Cress Creek community in historic Shepherdstown. Situated just minutes from downtown Shepherdstown and Shepherd University, this location offers the perfect balance of peaceful living with easy access to dining, shopping, and cultural experiences.From the moment you step

  Sara Duncan RE/MAX Distinctive Real Estate

  22 Reachcliff Cir, Shepherdstown, WV 25443
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  /62

  $500,000 Sold Jan 17, 2025

  • 2,465 Sq Ft
  • $203/SF
  • 75 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1974

  157 Steamboat Run Rd, Shepherdstown, WV 25443

  Welcome to 157 Steamboat Run Road. Minutes from historic downtown Shepherdstown. Make your memories and be a part of Steamboat Run Community. Home has been occupied by the original owners. This property includes 2 lots that were combined into one. Grab your kayak or canoe and enjoy the river access in the common area. This beautiful 4 bedrooms 2 and 1/2 bath Cushwa brick home has hardwood

  Marika Milburn Greentree Associates of Shepherdstown, Inc.

  157 Steamboat Run Rd, Shepherdstown, WV 25443
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  /70

  Est $384,184 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,508 Sq Ft

  365 Big Oak Dr, Shepherdstown, WV 25443

  365 Big Oak Dr, Shepherdstown, WV 25443
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  /84

  $339,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,658 Sq Ft

  838 Billmyer Mill Rd, Shepherdstown, WV 25443

  MUST SEE! Enjoy country living sitting on the large front porch of this brick raised rancher overlooking beautiful farmland near historic Shepherdstown and Shepherd University. Home features two (2) bedrooms, kitchen, living room, dining room w/exit to a large tiered deck, full bathroom, breezeway w/laundry, plus a large partially finished basement w/woodstore, storage and 2 car attached garage.

  Densil Nibert Nibert Realty & Auctions, LLC

  838 Billmyer Mill Rd, Shepherdstown, WV 25443
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  /12

  $165,000 Sold Jan 10, 2025

  • Land
  • 2.74 Acres
  • $60,219 per Acre

  • 1 Day On Market

  318 Comstock Dr, Shepherdstown, WV 25443

  The property at 318 Comstock Drive in Shepherdstown, WV, is a 2.74-acre piece of land located in the Potomac River Farms subdivision. It is within walking distance of community access to the Potomac River and about 10 minutes from Shepherdstown's downtown area, known for its dining and shopping options. The property features a 12x36 horse barn with electric previously used for two horses, a

  Eric Rodia Gain Realty

  318 Comstock Dr, Shepherdstown, WV 25443
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  /47

  Est $469,321 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  129 Morgan Grove Rd, Shepherdstown, WV 25443

  129 Morgan Grove Rd, Shepherdstown, WV 25443
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  /53

  $649,900 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,654 Sq Ft

  130 N Tamarac Dr, Shepherdstown, WV 25443

  Custom built 3 bedroom 2 full bath Craftsman style home in 2023 with single floor living in mind with zero steps and thresholds throughout home.. The attention to detail in this house is 2nd to none. So if your looking for a home straight out of a magazine that you don't have to lift a finger on then look no further. As this house will catch your eye from the time you drive up and and keep

  Travis Davis Pearson Smith Realty, LLC

  130 N Tamarac Dr, Shepherdstown, WV 25443
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  /65

  $749,000 Sold Jan 08, 2025

  • 5,768 Sq Ft
  • $130/SF
  • 16 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2016

  116 Horner Farm Ln, Shepherdstown, WV 25443

  Multiple offers received. Please present highest and best by 12/09/2024 at 5:00. Wrapped in a bow and ready for you to enjoy for the holidays! This remarkable 5 bedroom, 4.5 bathroom home rests on a large, corner lot with a fenced-in backyard and finished basement! It truly offers everything on your wishlist with an abundance of space and upgrades throughout. Upon entering the home, you will

  Errika Best Greentree Associates of Shepherdstown, Inc.

  116 Horner Farm Ln, Shepherdstown, WV 25443

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