Shepherdstown, WV Homes

• 

  

  

  /20

  $949,000

  • 3 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  105 Rabbits Rest Ln, Shepherdstown, WV 25443

  Price Improvement! Experience the perfect blend of privacy, luxury, and country living at this stunning Lindal Cedar Home nestled on 10.08 unrestricted acres in sought-after Shepherdstown. This exceptional property offers a rare opportunity for those seeking space to spread out while remaining conveniently located near Historic Shepherdstown, Harpers Ferry, Charles Town, and MARC train stations

  Jennifer Fortson Charis Realty Group

  105 Rabbits Rest Ln, 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

  Current Estimated Value $348,817

  Last Listing Agent Kara Burnett Samson Properties

  53 Stonehouse Ln, Shepherdstown, WV 25443
• 

  

  

  /60

  Est $433,575

  Not Listed For Sale

  15 Shaw Place, Shepherdstown, WV 25443

  • 4 Beds
  • 2.5 Baths
  • 2,924 Sq Ft
  • Built 2010

  15 Shaw Place, Shepherdstown, WV 25443

  Last Sold Summary

  • 6 Days On Market
• 

  

  

  /84

  $789,000

  Pending

  • 4 Beds
  • 3 Baths
  • 3,710 Sq Ft

  266 Shepherd Ln, Shepherdstown, WV 25443

  Nestled in the serene Ledge Lowe Estates, this charming Cape Cod home offers a perfect blend of comfort and style. With 4 spacious bedrooms, Study, Flex Room for crafting, or homeschooling, and enclosed back porch as well as 3 full bathrooms, this residence is designed for both relaxation and entertaining. Step inside to discover warm wood floors and a traditional floor plan that invites you to

  Paula Miller Coldwell Banker Premier

  266 Shepherd Ln, Shepherdstown, WV 25443
• 

  

  

  /64

  $845,000

  Sold Jun 03, 2026

  86 Battista Way, Shepherdstown, WV 25443

  • 4 Beds
  • 4.5 Baths
  • 4,884 Sq Ft
  • Built 2018

  Last Sold Summary

  • 1% Below List Price
  • $173/SF
  • 6 Days On Market

  Current Estimated Value $819,060

  Last Listing Agent Adam Miller Coldwell Banker Premier

  86 Battista Way, Shepherdstown, WV 25443
• 

  

  /59

  Est $449,774

  Not Listed For Sale

  451 Maddex Farm Dr, Shepherdstown, WV 25443

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

  451 Maddex Farm Dr, Shepherdstown, WV 25443

  Last Sold Summary

  • 21 Days On Market
• 

  

  /69

  $600,000

  • 4 Beds
  • 3 Baths
  • 2,878 Sq Ft

  89 Morgan Grove Rd, Shepherdstown, WV 25443

  Absolutely gorgeous 4-bedroom, 3-bathroom, home with approximately 2878 total finished square feet, sitting on 6.01 UNRESTRICTED, PRIVATE ACRES in Shepherdstown. This property is in a great location, only 2.5 miles from Shepherd University and about 5 minutes from downtown Shepherdstown. Updates include: a NEW ROOF, NEW HVAC, new hot water heater, new siding, fresh paint from top to bottom, new

  Sheldon Everhart Freedom Real Estate Group, LLC.

  89 Morgan Grove Rd, 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

  Current Estimated Value $563,438

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

  79 Leisure Way, Shepherdstown, WV 25443
• 

  

  /53

  Est $393,685

  Not Listed For Sale

  527 Maddex Farm Dr, Shepherdstown, WV 25443

  • 3 Beds
  • 2.5 Baths
  • 2,290 Sq Ft
  • Built 2010

  527 Maddex Farm Dr, Shepherdstown, WV 25443

  Last Sold Summary

  • 34 Days On Market
• 

  

  /9

  $99,900

  Pending

  • Land
  • 18,730 Sq Ft
  • $232,326 per Acre

  0 Maddex Dr, Shepherdstown, WV 25443

  Residential building lot opportunity here! Corner lot to Maddex Drive, Martinsburg Pike and Hensel Drive. Directly across from the Shepherdstown Fire Department and Maddex Professional Court. .4382 acre lot. Can not operate any commercial establishment on the premises herein conveyed where gasoline or gasoline products or food or beverages are sold at either wholesale or retail, and that they

  Brad Lewis Greentree Associates of Shepherdstown, Inc.

  0 Maddex Dr, Shepherdstown, WV 25443
• 

  

  /44

  $490,000

  Sold May 08, 2026

  347 Maddex Dr, Shepherdstown, WV 25443

  • 4 Beds
  • 3.5 Baths
  • 3,684 Sq Ft
  • Built 2007

  Last Sold Summary

  • 4% Below List Price
  • $133/SF
  • 36 Days On Market

  Current Estimated Value $498,265

  Last Listing Agent Brittany Newman Dream Driven Properties, LLC

  347 Maddex Dr, Shepherdstown, WV 25443
• 

  

  /36

  Est $311,492

  Not Listed For Sale

  127 Swearingen Way, Shepherdstown, WV 25443

  • 4 Beds
  • 3 Baths
  • 1,980 Sq Ft
  • Built 2007

  127 Swearingen Way, Shepherdstown, WV 25443

  Last Sold Summary

  • 6 Days On Market
• 

  

  /17

  $560,000

  Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,907 Sq Ft

  183 Fairmont Ave, Shepherdstown, WV 25443

  Welcome to 183 Fairmont Avenue, a charming home ideally located in the heart of historic Shepherdstown. This classic residence offers approximately 1,900 square feet of living space with three bedrooms and one-and-a-half baths, blending timeless character with everyday functionality. Situated on a spacious corner lot, the property provides a generous yard with room for gardening, outdoor

  Brant Lowe Path Realty

  183 Fairmont Ave, Shepherdstown, WV 25443
• 

  /2

  $460,000

  Sold May 20, 2026

  41 Weese Point, Shepherdstown, WV 25443

  • 4 Beds
  • 2.5 Baths
  • 2,902 Sq Ft
  • Built 2009

  Last Sold Summary

  • $159/SF
  • 4 Days On Market

  Current Estimated Value $462,213

  Last Listing Agent Stacey Lee Samson Properties

  41 Weese Point, Shepherdstown, WV 25443
• 

  

  /28

  Est $318,775

  Not Listed For Sale

  123 Swearingen Way, Shepherdstown, WV 25443

  • 4 Beds
  • 4 Baths
  • 2,380 Sq Ft
  • Built 2007

  123 Swearingen Way, Shepherdstown, WV 25443

  Last Sold Summary

  • 23 Days On Market
• 

  

  /41

  $420,000

  • 3 Beds
  • 2.5 Baths
  • 1,754 Sq Ft

  122 Hensel Dr, Shepherdstown, WV 25443

  Main level living never looked so easy in this newly renovated and move-in ready contemporary home in the desirable Maddex Farm community with its connecting pathways to the town and University. Brand new architectural shingle roof, freshly painted with hardwood floors, and new carpet in the bedrooms and luxury vinyl tile in the bathrooms - this home has been renovated on all levels, inside and

  Adam Miller Coldwell Banker Premier

  122 Hensel Dr, Shepherdstown, WV 25443
• 

  /2

  $390,000

  Sold Apr 02, 2026

  203 W New St, Shepherdstown, WV 25443

  • 2 Beds
  • 1.5 Baths
  • 1,194 Sq Ft
  • Built 1930

  Last Sold Summary

  • 1% Below List Price
  • $327/SF
  • 3 Days On Market

  Current Estimated Value $380,676

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

  203 W New St, Shepherdstown, WV 25443
• 

  

  /68

  Est $523,980

  Not Listed For Sale

  182 Maddex Square Dr, Shepherdstown, WV 25443

  • 5 Beds
  • 3.5 Baths
  • 4,185 Sq Ft
  • Built 2004

  182 Maddex Square Dr, Shepherdstown, WV 25443

  Last Sold Summary

  • 41 Days On Market
• 

  

  /60

  $635,000

  $15K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,176 Sq Ft

  185 Shepherd Ln, Shepherdstown, WV 25443

  Set on 4.07 acres just minutes from downtown Shepherdstown, this spacious home offers room to spread out, a peaceful setting, and the opportunity to make it your own. A covered front porch leads into a well-designed main level with formal living and dining rooms featuring hardwood floors, a comfortable family room with built-in shelving and a wood-burning fireplace that is currently capped, a

  Liz McDonald Dandridge Realty Group, LLC

  185 Shepherd Ln, Shepherdstown, WV 25443
• 

  /2

  $557,500

  Sold Jun 18, 2026

  286 Falling Spring Rd, Shepherdstown, WV 25443

  • 4 Beds
  • 3 Baths
  • 3,502 Sq Ft
  • Built 1990

  Last Sold Summary

  • 4% Above List Price
  • $159/SF
  • 5 Days On Market

  Current Estimated Value $534,755

  Last Listing Agent Jim Hafer Berkshire Hathaway Homeservices Homesale Realty

  286 Falling Spring Rd, Shepherdstown, WV 25443
• 

  

  /19

  Est $238,145

  Not Listed For Sale

  15 Raven Way, Shepherdstown, WV 25443

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Built 1980

  15 Raven Way, Shepherdstown, WV 25443

  Last Sold Summary

  • 42 Days On Market
• 

  

  /5

  $659,999

  New Construction Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,282 Sq Ft

  0 Beasley Dr, Shepherdstown, WV 25443

  TO BE BUILT - 3 bedroom, 2 and 1/2 bathrooms on over 4 acres. This beautiful homesite is located in historic Shepherdstown. The front entrance has a 46' covered porch with with columns and double doors that open to a spacious foyer. Let the kitchen be the focal point of this open concept with a 7' kitchen island with prep sink and eating bar. Enormous 11'x5' pantry with window. The kitchen

  Scott Wachtel Path Realty

  0 Beasley Dr, Shepherdstown, WV 25443
• 

  

  /78

  $565,000

  Sold May 01, 2026

  55 Hidden Valley Cir, Shepherdstown, WV 25443

  • 4 Beds
  • 3.5 Baths
  • 4,128 Sq Ft
  • Built 1994

  Last Sold Summary

  • $137/SF
  • 163 Days On Market

  Current Estimated Value $576,836

  Last Listing Agent Nicholas Palkovic Touchstone Realty, LLC

  55 Hidden Valley Cir, Shepherdstown, WV 25443
• 

  

  /79

  Est $321,832

  Not Listed For Sale

  242 Meadowlark Ln, Shepherdstown, WV 25443

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1972

  242 Meadowlark Ln, Shepherdstown, WV 25443

  Last Sold Summary

  • 88 Days On Market
• 

  

  /3

  $500,000

  • Land
  • 29,185 Sq Ft
  • $746,269 per Acre

  Lot 2 Martinsburg Pike, Shepherdstown, WV 25443

  Platted as Seneca Crossing. DRIVE THROUGH WINDOWS ALLOWED! Bring on the fast food, coffee shop, bakery, etc. This parcel was part of a 4.44 parcel that was sold to WVU Medical Center which is adjacent. ROCS's convenience store is also adjacent. Dominos' is across the road. A 40 unit apartment complex has been approved for across the road as well! This pad will be available for mixed use. Also,

  Jacqueline Lewis Greentree Associates of Shepherdstown, Inc.

  Lot 2 Martinsburg Pike, Shepherdstown, WV 25443
• 

  

  /13

  $124,000

  Sold Nov 21, 2025

  0 N Tamarac Dr Unit WVJF2019108, Shepherdstown, WV 25443

  • Land
  • 24,829 Sq Ft
  • $217,544 per Acre

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Brian Masemer RE/MAX Real Estate Group

  0 N Tamarac Dr Unit WVJF2019108, Shepherdstown, WV 25443
• 

  

  /70

  Est $551,272

  Not Listed For Sale

  232 Southpaw Ln, Shepherdstown, WV 25443

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

  232 Southpaw Ln, Shepherdstown, WV 25443

  Last Sold Summary

  • 80 Days On Market
• 

  

  /17

  $183,000

  • Land
  • 3.39 Acres
  • $53,982 per Acre

  Lot #5 Shepherds Cove Swift River Way, Shepherdstown, WV 25443

  Shepherds Cove Potomac River Waterfront Community, Shepherdstown WV Home Sites in a small , resort-like community. Hurry the last 4 lots available in a community of 19 lots. Large private lots with marina privileges,. Enjoy the beauty of nature in the wooded setting. Hiking trails and Biking paths boating, fishing, swimming, kayak and canoe. Marina with individual dock space may be available ,

  Carolyn Snyder Snyder Bailey & Associates

  Lot #5 Shepherds Cove Swift River Way, Shepherdstown, WV 25443
• 

  /2

  $492,500

  Sold Jan 30, 2026

  103 E New St, Shepherdstown, WV 25443

  • 3 Beds
  • 2.5 Baths
  • 2,244 Sq Ft
  • Built 1800

  Last Sold Summary

  • $219/SF
  • 29 Days On Market

  Current Estimated Value $497,201

  Last Listing Agent Tara Lowe Samson Properties

  103 E New St, Shepherdstown, WV 25443
• 

  

  /50

  Est $261,019

  Not Listed For Sale

  392 Persimmon Ln, Shepherdstown, WV 25443

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1985

  392 Persimmon Ln, Shepherdstown, WV 25443

  Last Sold Summary

  • 10 Days On Market
• 

  

  /65

  $599,900

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,745 Sq Ft

  63 Hackberry Cir, Shepherdstown, WV 25443

  Nestled in the serene and well-cared for neighborhood of Fernbank, which is adjacent to The Club at Cress Creek golf course, this charming colonial home offers a perfect blend of comfort, nature, and privacy within a golf course community. This property has been well maintained and loved. It is in move-in ready condition, while affording opportunities to update and personalize the property, if

  Susan Reichel Coldwell Banker Premier

  63 Hackberry Cir, Shepherdstown, WV 25443
• 

  

  /62

  $450,000

  Sold Dec 05, 2025

  1337 Cedar Ln, Shepherdstown, WV 25443

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft
  • Built 1990

  Last Sold Summary

  • $238/SF
  • 58 Days On Market

  Current Estimated Value $466,104

  Last Listing Agent Lesley Lopez ERA Liberty Realty

  1337 Cedar Ln, Shepherdstown, WV 25443
• 

  

  /43

  Est $518,999

  Not Listed For Sale

  841 Persimmon Ln, Shepherdstown, WV 25443

  • 4 Beds
  • 3 Baths
  • 2,466 Sq Ft
  • Built 1990

  841 Persimmon Ln, Shepherdstown, WV 25443

  Last Sold Summary

  • 43 Days On Market
• 

  

  /64

  $575,000

  • 4 Beds
  • 3.5 Baths
  • 2,866 Sq Ft

  637 Persimmon Ln, Shepherdstown, WV 25443

  Move In Ready, 4 bed, 3.5 bath Farmette on 2.25 Unrestricted acres in Shepherdstown. This home has many updates including a NEW ROOF, 2 New HVAC Units, New Hot Water Heater, New bathrooms with custom tile and quartz tops, New LVP flooring, fresh paint from top to bottom, New hardware and fixtures. The brand new kitchen features stainless steel appliances and quartz counter tops. Other features

  Sheldon Everhart Freedom Real Estate Group, LLC.

  637 Persimmon Ln, Shepherdstown, WV 25443
• 

  

  /5

  $120,000

  Sold May 27, 2026

  0 Morgan Grove Road 2 35 Acres, Shepherdstown, WV 25443

  • Land
  • 2.35 Acres
  • $51,064 per Acre

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Heidi Johnston Keller Williams Realty Advantage

  0 Morgan Grove Road 2 35 Acres, Shepherdstown, WV 25443
• 

  

  /78

  Est $782,136

  Not Listed For Sale

  484 Billmyer Mill Rd, Shepherdstown, WV 25443

  • 4 Beds
  • 2 Baths
  • 2,794 Sq Ft
  • Built 1860

  484 Billmyer Mill Rd, Shepherdstown, WV 25443

  Last Sold Summary

  • 182 Days On Market
• 

  

  /67

  $309,000

  $20K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,352 Sq Ft

  19 Cardinal Dr, Shepherdstown, WV 25443

  Bill Cafferky Snyder Bailey & Associates

  19 Cardinal Dr, Shepherdstown, WV 25443
• 

  

  /38

  $329,000

  Sold May 06, 2026

  43 Ryan Ct, Shepherdstown, WV 25443

  • 3 Beds
  • 3.5 Baths
  • 1,835 Sq Ft
  • Built 1992

  Last Sold Summary

  • $179/SF
  • 18 Days On Market

  Current Estimated Value $327,504

  Last Listing Agent Adam Miller Coldwell Banker Premier

  43 Ryan Ct, Shepherdstown, WV 25443
• 

  

  /96

  Est $945,912

  Not Listed For Sale

  1827 Terrapin Neck Rd, Shepherdstown, WV 25443

  • 3 Beds
  • 2.5 Baths
  • 3,427 Sq Ft
  • Built 1995

  1827 Terrapin Neck Rd, Shepherdstown, WV 25443

  Last Sold Summary

  • 6 Days On Market
• 

  

  /82

  $599,000

  $26K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,950 Sq Ft

  49 Appomattox Ln, Shepherdstown, WV 25443

  Stunning 5-bedroom, 3.5-bath Colonial tucked away on a private half-acre lot backing to mature trees in the sought-after Willow Springs Acres community of Shepherdstown, WV. Offering spacious living across three finished levels, this home combines timeless style, functional design, and peaceful outdoor living. Step inside to a dramatic 2-story foyer flanked by a private home office and elegant

  Liz McDonald Dandridge Realty Group, LLC

  49 Appomattox Ln, Shepherdstown, WV 25443

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