Shepherdstown, WV Homes

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  /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 $566,767

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

  79 Leisure Way, Shepherdstown, WV 25443
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  /106

  Est $620,910 Not Listed For Sale

  977 Turner Rd, Shepherdstown, WV 25443

  • 5 Beds
  • 4 Baths
  • 4,184 Sq Ft
  • Built 1980

  977 Turner Rd, Shepherdstown, WV 25443

  Last Sold Summary

  • 38% Below List Price
  • $238/SF
  • 195 Days On Market

  Last Sold Price $995,000

  Last Listing Agent Elizabeth Sager Samson Properties
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  /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
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  /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
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  /96

  Est $950,892 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

  • 14% Below List Price
  • $321/SF
  • 6 Days On Market

  Last Sold Price $1,100,000

  Last Listing Agent Terry Walker Coldwell Banker Premier
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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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  /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 $585,919

  Last Listing Agent Andrew Lowe Path Realty

  71 Rolling Green Ct, Shepherdstown, WV 25443
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  /34

  Est $604,628 Not Listed For Sale

  40 Mossy Oak Ct, Shepherdstown, WV 25443

  • 4 Beds
  • 2.5 Baths
  • 3,805 Sq Ft
  • Built 2006

  40 Mossy Oak Ct, Shepherdstown, WV 25443

  Last Sold Summary

  • 1% Above List Price
  • $158/SF
  • 32 Days On Market

  Last Sold Price $600,000

  Last Listing Agent Mercedes Prohaska Coldwell Banker Premier
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  /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
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  /13

  $124,000 Sold Nov 21, 2025

  0 N Tamarac Dr Unit WVJF2019108, Shepherdstown, WV 25443

  • Land
  • 0.57 Acre
  • $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
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  /41

  Est $634,912 Not Listed For Sale

  60 Pathfinder Ct, Shepherdstown, WV 25443

  • 5 Beds
  • 4.5 Baths
  • 5,204 Sq Ft
  • Built 2005

  60 Pathfinder Ct, Shepherdstown, WV 25443

  Last Sold Summary

  • 9% Above List Price
  • $111/SF
  • 5 Days On Market

  Last Sold Price $580,000

  Last Listing Agent Joy Lewis Greentree Associates of Shepherdstown, Inc.
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  /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
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  /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 $514,810

  Last Listing Agent Tara Lowe Samson Properties

  103 E New St, Shepherdstown, WV 25443
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  /28

  Est $335,967 Not Listed For Sale

  274 Starkeys Landing, Shepherdstown, WV 25443

  • 3 Beds
  • 4 Baths
  • 2,180 Sq Ft
  • Built 2007

  274 Starkeys Landing, Shepherdstown, WV 25443

  Last Sold Summary

  • 10% Above List Price
  • $140/SF
  • 3 Days On Market

  Last Sold Price $305,000

  Last Listing Agent Joy Lewis Greentree Associates of Shepherdstown, Inc.
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  /15

  $395,000

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

  203 W New St, Shepherdstown, WV 25443

  The phrase " less is more " certainly applies here. Enjoy less maintenance and upkeep in this " move in condition '' with abundant light. in town cottage All of Shepherdstown's sought after amenities are within easy reach. Airports, train and commuter routes are a breeze to access. If US history is an interest, Antietam, Harpers Ferry and Gettysburg national parks will certainly occupy your time.

  Dan Anderson Greentree Associates of Shepherdstown, Inc.

  203 W New St, Shepherdstown, WV 25443
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  /45

  $487,000 Sold Mar 04, 2025

  262 Maddex Farm Dr, Shepherdstown, WV 25443

  • 5 Beds
  • 3.5 Baths
  • 4,046 Sq Ft
  • Built 2006

  Last Sold Summary

  • $120/SF
  • 37 Days On Market

  Current Estimated Value $507,526

  Last Listing Agent Jay Deeds Keller Williams Realty Advantage

  262 Maddex Farm Dr, Shepherdstown, WV 25443
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  /65

  Est $309,520 Not Listed For Sale

  322 Starkeys Landing, Shepherdstown, WV 25443

  • 3 Beds
  • 2.5 Baths
  • 2,196 Sq Ft
  • Built 2007

  322 Starkeys Landing, Shepherdstown, WV 25443

  Last Sold Summary

  • 3% Above List Price
  • $137/SF
  • 1 Day On Market

  Last Sold Price $300,000

  Last Listing Agent Christine Reeder Long & Foster
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  /42

  $975,000

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

  105 Rabbits Rest Ln, Shepherdstown, WV 25443

  **** Update*****This home comes with unique financing opportunities! The seller is willing to offer partial owner financing, creating additional flexibility for well-qualified buyers. Plus, our preferred lender offers special financing solutions designed to help buyers explore more accessible loan programs. Ask for details Lindal Cedar Home on 10.08 Acres of Peace & BeautyTucked away on

  Jennifer Fortson Charis Realty Group

  105 Rabbits Rest Ln, Shepherdstown, WV 25443
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  /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 $449,899

  Last Listing Agent Lesley Lopez ERA Liberty Realty

  1337 Cedar Ln, Shepherdstown, WV 25443
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  /32

  Est $328,282 Not Listed For Sale

  338 Starkeys Landing, Shepherdstown, WV 25443

  • 3 Beds
  • 2.5 Baths
  • 2,196 Sq Ft
  • Built 2007

  338 Starkeys Landing, Shepherdstown, WV 25443

  Last Sold Summary

  • 6% Above List Price
  • $141/SF

  Last Sold Price $310,000

  Last Listing Agent Marcy Deck Dandridge Realty Group, LLC
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  /26

  $395,990 New Construction

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

  18 Riderwood Way, Shepherdstown, WV 25443

  Quick Move In! Back to Trees! 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

  D.R. Horton Builder

  18 Riderwood Way, Shepherdstown, WV 25443
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  /52

  $465,000 Sold Sep 17, 2025

  23 Fairmont Ave, Shepherdstown, WV 25443

  • 4 Beds
  • 2 Baths
  • 2,036 Sq Ft
  • Built 1966

  Last Sold Summary

  • $228/SF
  • 66 Days On Market

  Current Estimated Value $475,514

  Last Listing Agent Tara Lowe Samson Properties

  23 Fairmont Ave, Shepherdstown, WV 25443
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  /36

  Est $308,521 Not Listed For Sale

  384 Starkeys Landing, Shepherdstown, WV 25443

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

  384 Starkeys Landing, Shepherdstown, WV 25443

  Last Sold Summary

  • 4% Below List Price
  • $144/SF
  • 58 Days On Market

  Last Sold Price $320,000

  Last Listing Agent Richard Kendall Snyder Bailey & Associates
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  /73

  $1,600,000

  • Studio
  • 3,692 Sq Ft

  1585 Gardners Ln, Shepherdstown, WV 25443

  1585 Gardners Lane: Circa 1850 Farmhouse converted into 6 apartments, 2 cottages and 1 duplex totaling 10 units on 13.2 acres with huge bank barn and fencing/pasture for horses. 100% occupancy, great rental history over past 20 years of ownership. Roughly $11k per month totaling a potential yearly income of $132,910 (2025). Current owner operated and managed these units as short term rentals on

  Brad Lewis Greentree Associates of Shepherdstown, Inc.

  1585 Gardners Ln, Shepherdstown, WV 25443
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  /52

  $438,000 Sold Sep 16, 2025

  467 Maddex Farm Dr, Shepherdstown, WV 25443

  • 4 Beds
  • 2.5 Baths
  • 4,000 Sq Ft
  • Built 2011

  Last Sold Summary

  • $110/SF
  • 19 Days On Market

  Current Estimated Value $443,904

  Last Listing Agent Jeanne Cooper Century 21 Redwood Realty

  467 Maddex Farm Dr, Shepherdstown, WV 25443
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  /54

  Est $399,963 Not Listed For Sale

  565 Maddex Farm Dr, Shepherdstown, WV 25443

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft
  • Built 2009

  565 Maddex Farm Dr, Shepherdstown, WV 25443

  Last Sold Summary

  • 4% Above List Price
  • $193/SF
  • 32 Days On Market

  Last Sold Price $385,000

  Last Listing Agent Adam Shively Samson Properties
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  /31

  $449,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,340 Sq Ft

  108 Open Gate Ln, Shepherdstown, WV 25443

  Quick Move In! 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 countertops and White

  D.R. Horton Builder

  108 Open Gate Ln, Shepherdstown, WV 25443
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  /57

  $585,000 Sold Sep 12, 2025

  164 Butcher Ct, Shepherdstown, WV 25443

  • 4 Beds
  • 3.5 Baths
  • 4,884 Sq Ft
  • Built 2005

  Last Sold Summary

  • $120/SF
  • 41 Days On Market

  Current Estimated Value $588,817

  Last Listing Agent Carolyn Young Samson Properties

  164 Butcher Ct, Shepherdstown, WV 25443
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  /40

  Est $529,596 Not Listed For Sale

  119 Thatcher Ct, Shepherdstown, WV 25443

  • 4 Beds
  • 3.5 Baths
  • 4,344 Sq Ft
  • Built 2006

  119 Thatcher Ct, Shepherdstown, WV 25443

  Last Sold Summary

  • 3% Above List Price
  • $119/SF
  • 17 Days On Market

  Last Sold Price $515,000

  Last Listing Agent Gavin Washington Weichert Corporate
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  /9

  $99,900

  • Land
  • 0.43 Acre
  • $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
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  /64

  $375,000 Sold Sep 30, 2025

  501 Maddex Farm Dr, Shepherdstown, WV 25443

  • 3 Beds
  • 2.5 Baths
  • 1,903 Sq Ft
  • Built 2015

  Last Sold Summary

  • $197/SF
  • 48 Days On Market

  Current Estimated Value $378,864

  Last Listing Agent Tara Lowe Samson Properties

  501 Maddex Farm Dr, Shepherdstown, WV 25443
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  /78

  Est $437,053 Not Listed For Sale

  145 Canal Way, Shepherdstown, WV 25443

  • 4 Beds
  • 2.5 Baths
  • 2,716 Sq Ft
  • Built 2007

  145 Canal Way, Shepherdstown, WV 25443

  Last Sold Summary

  • 4% Above List Price
  • $155/SF
  • 2 Days On Market

  Last Sold Price $420,000

  Last Listing Agent Tara Lowe Samson Properties
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  /71

  $715,000

  • 5 Beds
  • 4.5 Baths
  • 4,583 Sq Ft

  48 Field Crest Ct, Shepherdstown, WV 25443

  Property located in one of the nicest subdivisions in Jefferson County.Home over 5,600 finished square feet, kitchen with updated stainless appliances, breakfast area adjacent to living room. Beautiful wood floors throughout most of the house. Basement has a bedroom and full bath, large rec room, gym area and plenty of storage. Amazing views from all windows, rear deck off the living room

  Piedad Suarez Spring Hill Real Estate, LLC.

  48 Field Crest Ct, Shepherdstown, WV 25443
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  /49

  $575,000 Sold Jul 25, 2025

  1075 Willowdale Dr, Shepherdstown, WV 25443

  • 3 Beds
  • 3.5 Baths
  • 2,916 Sq Ft
  • Built 1982

  Last Sold Summary

  • $197/SF
  • 55 Days On Market

  Current Estimated Value $595,733

  Last Listing Agent Susan Reichel Coldwell Banker Premier

  1075 Willowdale Dr, Shepherdstown, WV 25443
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  /38

  Est $509,182 Not Listed For Sale

  157 Canal Way, Shepherdstown, WV 25443

  • 4 Beds
  • 3.5 Baths
  • 4,337 Sq Ft
  • Built 2007

  157 Canal Way, Shepherdstown, WV 25443

  Last Sold Summary

  • 2% Above List Price
  • $115/SF
  • 3 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Kathy Colville Century 21 Redwood Realty
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  /3

  $500,000

  • Land
  • 0.67 Acre
  • $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
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  /26

  $600,000 Sold Jun 20, 2025

  75 Juniper Cir, Shepherdstown, WV 25443

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft
  • Built 2001

  Last Sold Summary

  • $232/SF
  • 74 Days On Market

  Current Estimated Value $613,753

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

  75 Juniper Cir, Shepherdstown, WV 25443
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  /67

  Est $465,811 Not Listed For Sale

  116 Butcher Ct, Shepherdstown, WV 25443

  • 4 Beds
  • 3.5 Baths
  • 3,866 Sq Ft
  • Built 2005

  116 Butcher Ct, Shepherdstown, WV 25443

  Last Sold Summary

  • 3% Below List Price
  • $124/SF
  • 30 Days On Market

  Last Sold Price $480,000

  Last Listing Agent Garrett Norman Samson Properties
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  /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 , Private access to

  Carolyn Snyder Snyder Bailey & Associates

  Lot #5 Shepherds Cove Swift River Way, Shepherdstown, WV 25443
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  /51

  $580,000 Sold Nov 07, 2025

  328 Comstock Dr, Shepherdstown, WV 25443

  • 4 Beds
  • 2.5 Baths
  • 2,235 Sq Ft
  • Built 2025

  Last Sold Summary

  • $260/SF
  • 33 Days On Market

  Last Listing Agent Rick Boswell Gain Realty

  328 Comstock Dr, Shepherdstown, WV 25443

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