Shepherdstown, WV Homes

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  /23

  $449,900

  • Land
  • 7.85 Acres
  • $57,312 per Acre

  0 Ridge Rd Unit WVJF2020954, Shepherdstown, WV 25443

  Don't miss out on this rare opportunity to own nearly 8 UNRESTRICTED acres in Shepherdstown. Sweeping sunset views make this a perfect location to lay down roots and build your forever home.Build with confidence as major groundwork is already complete. Perc-approved for a 4-bedroom house with well already in place. Experience true flexibility to build your dream home with NO HOA. Although the

  James Smith Burch Real Estate Group, LLC

  0 Ridge Rd Unit WVJF2020954, Shepherdstown, WV 25443
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  /50

  $425,000 Sold Dec 12, 2025

  174 Byer Ln, Shepherdstown, WV 25443

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft
  • Built 1977

  Last Sold Summary

  • $204/SF
  • 35 Days On Market

  Last Listing Agent Chris Hoffmaster Berkshire Hathaway Homeservices Homesale Realty

  174 Byer Ln, Shepherdstown, WV 25443
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  /29

  Not Listed For Sale

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

  231 Lyon Ridge Rd, Shepherdstown, WV 25443

  231 Lyon Ridge Rd, Shepherdstown, WV 25443
• 

  

  /2

  $825,000

  • Land
  • 3.7 Acres
  • $222,973 per Acre

  8285 Martinsburg Pike, Shepherdstown, WV 25443

  PRIME LAND adjacent to Shepherd University, Domino's, and, across the street from WVU Medical PRIME LAND adjacent to Shepherd University, Domino's, and, across the street from WVU Medical Facility and ROC's convenience store! SENECA CROSSING NORTHSIDE apartment concept... 40 units have been approved for this site...five buildings of eight units each. Perfect site for much needed apartments. House

  Jacqueline Lewis Greentree Associates of Shepherdstown, Inc.

  8285 Martinsburg Pike, Shepherdstown, WV 25443
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  /59

  $460,000 Sold Apr 30, 2025

  451 Maddex Farm Dr, Shepherdstown, WV 25443

  • 4 Beds
  • 2.5 Baths
  • 2,935 Sq Ft
  • Built 2010

  Last Sold Summary

  • $157/SF
  • 21 Days On Market

  Current Estimated Value $456,803

  Last Listing Agent Adam Shively Samson Properties

  451 Maddex Farm Dr, Shepherdstown, WV 25443
• 

  

  /15

  Est $314,667 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,288 Sq Ft

  310 W German St, Shepherdstown, WV 25443

  310 W German St, Shepherdstown, WV 25443
• 

  

  /38

  $469,990 New Construction

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

  92 Open Gate Ln, Shepherdstown, WV 25443

  Move-in ready! Complete with main level bedroom, and finished basement rec room! 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 the main living spaces, included kitchen appliances, granite countertops and Espresso cabinets give the updated look you've

  D.R. Horton Builder

  92 Open Gate Ln, Shepherdstown, WV 25443
• 

  

  /10

  $120,000 Sold Mar 25, 2025

  0 Steamboat Run Rd Unit WVJF2016174, Shepherdstown, WV 25443

  • Land
  • 1.55 Acres
  • $77,419 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Terri Evans Keller Williams Realty

  0 Steamboat Run Rd Unit WVJF2016174, Shepherdstown, WV 25443
• 

  

  /60

  Est $449,787 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,924 Sq Ft

  15 Shaw Place, Shepherdstown, WV 25443

  15 Shaw Place, Shepherdstown, WV 25443
• 

  

  /28

  $439,990 Pending

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

  101 Open Gate Ln, Shepherdstown, WV 25443

  The beautiful Bristol floorplan offers a charming front porch with stone detail. As you enter the main level, the open-concept design offers great space for entertaining; 3 bedrooms (including a master suite) and 2 full baths. The kitchen is grounded by a spacious central island with seating. Off of the kitchen, there is a separate space for formal dining, all leading to a beautiful covered back

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

  101 Open Gate Ln, Shepherdstown, WV 25443
• 

  

  /34

  $197,000 Sold Aug 26, 2025

  111 Ray St, Shepherdstown, WV 25443

  • 2 Beds
  • 1 Bath
  • 786 Sq Ft
  • Built 1950

  Last Sold Summary

  • $251/SF
  • 68 Days On Market

  Current Estimated Value $195,530

  Last Listing Agent Liz McDonald Dandridge Realty Group, LLC

  111 Ray St, Shepherdstown, WV 25443
• 

  

  /53

  Est $413,060 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,290 Sq Ft

  527 Maddex Farm Dr, Shepherdstown, WV 25443

  527 Maddex Farm Dr, Shepherdstown, WV 25443
• 

  

  /18

  $562,000

  • Land
  • 5.3 Acres
  • $106,038 per Acre

  LOt 9 Shepherds Cove Swift River Way, Shepherdstown, WV 25443

  LAST RIVER FRONT lot available at Shepherds Cove 5.4 Acre beautiful wooded lot sited on a bluff overlooking the Potomac River. BEAUTIFUL UNOBSTRUCTED VIEWS UP AND DOWN THE RIVER. Located in the shadow of historic Shepherdstown ,Shepherds Cove is a unique community for those selective home buyers who prefer woods and natural topography as their view , and golf carts as their preferred means to go

  Carolyn Snyder Snyder Bailey & Associates

  LOt 9 Shepherds Cove Swift River Way, Shepherdstown, WV 25443
• 

  

  /34

  $482,490 Sold Mar 24, 2025

  261 Lyon Ridge Rd, Shepherdstown, WV 25443

  • 4 Beds
  • 2.5 Baths
  • 2,969 Sq Ft
  • Built 2024

  Last Sold Summary

  • $163/SF
  • 209 Days On Market

  Last Listing Agent Kathleen Cassidy D R Horton Realty of Virginia LLC

  261 Lyon Ridge Rd, Shepherdstown, WV 25443
• 

  

  /68

  Est $524,397 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,185 Sq Ft

  182 Maddex Square Dr, Shepherdstown, WV 25443

  182 Maddex Square Dr, Shepherdstown, WV 25443
• 

  

  /17

  $209,000

  • Land
  • 4.36 Acres
  • $47,936 per Acre

  Lot #20 Shepherds Cove Swift River Way, Shepherdstown, WV 25443

  Shepherds Cove Potomac River Waterfront Community, Shepherdstown WV Lot 20 is an exceptional opportunity READY TO BUILD, beautiful wooded lot with well installed, lot has been cleared for house construction, community septic. Peaceful, tranquil setting. Shepherd Cove is a small , resort-like community of 19 lots with only 4 remaining. These large private lots have marina privileges, and private

  Carolyn Snyder Snyder Bailey & Associates

  Lot #20 Shepherds Cove Swift River Way, Shepherdstown, WV 25443
• 

  

  /104

  $923,000 Sold Mar 05, 2025

  405 Spring Creek Ln, Shepherdstown, WV 25443

  • 3 Beds
  • 2.5 Baths
  • 3,102 Sq Ft
  • Built 1825

  Last Sold Summary

  • $298/SF
  • 7 Days On Market

  Current Estimated Value $926,124

  Last Listing Agent Morgan Boyer Hunt Country Sotheby's International Realty

  405 Spring Creek Ln, Shepherdstown, WV 25443
• 

  

  /19

  Est $252,699 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  15 Raven Way, Shepherdstown, WV 25443

  15 Raven Way, Shepherdstown, WV 25443
• 

  

  /29

  $179,500

  • Land
  • 0.66 Acre
  • $271,970 per Acre

  0 Reachcliff Dr Unit WVJF2019398, Shepherdstown, WV 25443

  Tucked within one of the Eastern Panhandle’s most sought-after communities, Lot 107 on Reachcliff Drive presents a once-in-a-generation opportunity to build your custom home in Fernbank—known for its natural beauty, welcoming neighbors, and golf course setting. This lot provides 89' of frontage along the 5th fairway. Positioned at the highest elevation in the neighborhood, this wooded lot offers

  Tracy Kable Real Broker, LLC

  0 Reachcliff Dr Unit WVJF2019398, Shepherdstown, WV 25443
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  /47

  $215,000 Sold Oct 31, 2025

  24 Cavaland Terrace, Shepherdstown, WV 25443

  • 2 Beds
  • 1.5 Baths
  • 1,408 Sq Ft
  • Built 1976

  Last Sold Summary

  • $153/SF
  • 7 Days On Market

  Last Listing Agent Cheryl Yates ERA Liberty Realty

  24 Cavaland Terrace, Shepherdstown, WV 25443
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  /50

  Est $245,879 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  392 Persimmon Ln, Shepherdstown, WV 25443

  392 Persimmon Ln, Shepherdstown, WV 25443
• 

  

  /37

  $339,000

  • 3 Beds
  • 2.5 Baths
  • 2,680 Sq Ft

  286 Starkeys Landing, Shepherdstown, WV 25443

  Welcome to 286 Starkeys Landing, a spacious 3-bedroom, 2.5-bath townhome quietly set within the established Starkeys Landing community of Shepherdstown, West Virginia. Offering just over 2,100 square feet of finished living space, this home blends warmth, comfort, and light in a way that feels immediately like home. The lower level opens through a bright two-story foyer where sunlight filters

  Carolyn Young Samson Properties

  286 Starkeys Landing, Shepherdstown, WV 25443
• 

  

  /143

  $1,050,000 Sold Mar 21, 2025

  256 Swift River Way, Shepherdstown, WV 25443

  • 4 Beds
  • 4.5 Baths
  • 4,000 Sq Ft
  • Built 2023

  Last Sold Summary

  • $262/SF
  • 120 Days On Market

  Current Estimated Value $1,036,151

  Last Listing Agent Jamie Lopez ERA Liberty Realty

  256 Swift River Way, Shepherdstown, WV 25443
• 

  

  /43

  Est $485,348 Not Listed For Sale

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

  841 Persimmon Ln, Shepherdstown, WV 25443

  841 Persimmon Ln, Shepherdstown, WV 25443
• 

  

  /42

  $482,500

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  4381 Engle Molers Rd, Shepherdstown, WV 25443

  Welcome to this beautifully maintained all-brick rancher situated on a picturesque one-acre lot surrounded by pastoral and mountain views. Offering two bedrooms and one full bath, this home provides comfortable single-level living in a peaceful rural setting while still being conveniently located.Step outside and discover the property’s standout feature—an impressive, recently built 30' x 48'

  Sarah Santacroce Coldwell Banker Premier

  4381 Engle Molers Rd, Shepherdstown, WV 25443
• 

  

  /39

  $325,000 Sold Oct 15, 2025

  53 Stonehouse Ln, Shepherdstown, WV 25443

  • 3 Beds
  • 2.5 Baths
  • 2,466 Sq Ft
  • Built 1986

  Last Sold Summary

  • $132/SF
  • 16 Days On Market

  Last Listing Agent Kara Burnett Samson Properties

  53 Stonehouse Ln, Shepherdstown, WV 25443
• 

  

  /78

  Est $792,884 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,794 Sq Ft

  484 Billmyer Mill Rd, Shepherdstown, WV 25443

  484 Billmyer Mill Rd, Shepherdstown, WV 25443
• 

  

  /36

  $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
• 

  

  /49

  $555,000 Sold Jan 02, 2026

  79 Leisure Way, Shepherdstown, WV 25443

  • 4 Beds
  • 3.5 Baths
  • 4,455 Sq Ft
  • Built 1997

  Last Sold Summary

  • $125/SF
  • 32 Days On Market

  Last Listing Agent Jacqueline Lewis Greentree Associates of Shepherdstown, Inc.

  79 Leisure Way, Shepherdstown, WV 25443
• 

  

  /74

  Est $544,482 Not Listed For Sale

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

  564 Steamboat Run Rd, Shepherdstown, WV 25443

  564 Steamboat Run Rd, Shepherdstown, WV 25443
• 

  

  /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
• 

  

  /36

  $351,000 Sold Apr 07, 2025

  129 Larkspur Ln, Shepherdstown, WV 25443

  • 3 Beds
  • 2 Baths
  • 1,556 Sq Ft
  • Built 1971

  Last Sold Summary

  • $226/SF
  • 107 Days On Market

  Current Estimated Value $349,877

  Last Listing Agent Mercedes Prohaska Coldwell Banker Premier

  129 Larkspur Ln, Shepherdstown, WV 25443
• 

  

  /106

  Est $614,037 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 4,184 Sq Ft

  977 Turner Rd, Shepherdstown, WV 25443

  977 Turner Rd, Shepherdstown, WV 25443
• 

  

  /4

  $143,500

  • Land
  • 2.2 Acres
  • $65,227 per Acre

  0 Steamboat Run Rd Unit WVJF2019860, Shepherdstown, WV 25443

  You are in luck! This is one of the last remaining building lots in desireable Steamboat Run. Building site would be high, with a winter view of the river. Seller waiting for buyer to see where they would site the house and then once under contract, a perc test can be ordered. Property corners have been marked and staked with orange survey tape. This all wooded lot will not last!

  Jacqueline Lewis Greentree Associates of Shepherdstown, Inc.

  0 Steamboat Run Rd Unit WVJF2019860, Shepherdstown, WV 25443
• 

  

  /43

  $580,000 Sold May 01, 2025

  71 Rolling Green Ct, Shepherdstown, WV 25443

  • 4 Beds
  • 2.5 Baths
  • 2,594 Sq Ft
  • Built 2019

  Last Sold Summary

  • $224/SF
  • 8 Days On Market

  Current Estimated Value $586,031

  Last Listing Agent Andrew Lowe Path Realty

  71 Rolling Green Ct, Shepherdstown, WV 25443
• 

  

  /96

  Est $955,632 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,427 Sq Ft

  1827 Terrapin Neck Rd, Shepherdstown, WV 25443

  1827 Terrapin Neck Rd, Shepherdstown, WV 25443
• 

  

  /26

  $438,990 New Construction

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

  Penwell Plan at Tollhouse Woods, Shepherdstown, WV 25443

  The Penwell is a two-story plan with 4 bedrooms and 2.5 bathrooms in 2,148 square feet. The main level features a chef-inspired kitchen with an oversized island and walk-in pantry, as well as a flex room that’s ideal for a formal dining room or home office. The kitchen opens onto a spacious living room, perfect for the entertainer. The owner’s suite on the second level offers a luxurious owner’s

  D.R. Horton Builder

  19 Tollhouse Way Unit 36203410, Shepherdstown, WV 25443
• 

  

  /88

  $1,750,000 Sold Jan 24, 2025

  4001 Engle Molers Rd, Shepherdstown, WV 25443

  • 4 Beds
  • 3.5 Baths
  • 4,464 Sq Ft
  • Built 1986

  Last Sold Summary

  • $392/SF
  • 117 Days On Market

  Current Estimated Value $1,547,189

  Last Listing Agent Carolyn Snyder Snyder Bailey & Associates

  4001 Engle Molers Rd, Shepherdstown, WV 25443
• 

  

  /34

  Est $617,955 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,805 Sq Ft

  40 Mossy Oak Ct, Shepherdstown, WV 25443

  40 Mossy Oak Ct, Shepherdstown, WV 25443
• 

  

  /78

  $590,000 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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