Shepherdstown, WV Homes

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  /119

  $975,000 Sold Jul 01, 2025

  • 5,778 Sq Ft
  • $169/SF
  • 74 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1974

  115 Windward Ln, Shepherdstown, WV 25443

  PRICE REDUCTION! BACK ON THE MARKET, NO FAULT OF THE SELLERS. Home Inspection report is available. This is a rare one of a kind property that will not come around often, located in the much sought after Shepherdstown area! This property is directly across the street from Cress Creek, a private golf course, and approximately 1.5 miles from the quaint Shepherdstown downtown area and Shepherd

  Tracy Palmer Samson Properties

  115 Windward Ln, Shepherdstown, WV 25443
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  /28

  Est $323,918 Not Listed For Sale

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

  274 Starkeys Landing, Shepherdstown, WV 25443

  274 Starkeys Landing, Shepherdstown, WV 25443
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  /32

  $350,000

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft

  302 Starkeys Landing, Shepherdstown, WV 25443

  Updated end unit town home located in the Colonial Hills community of Shepherdstown. All three levels are finished and were upgraded with bump outs. Walk in at the lower level to an over-sized family room with full egress window, half bath, laundry room and entry to the attached one car garage. The main level features a dining/sunroom off the eat-in kitchen that leads out to a 16 x 15 deck with

  Gregorio Garcia Samson Properties

  302 Starkeys Landing, Shepherdstown, WV 25443
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  /41

  $360,500 Sold Jun 30, 2025

  • 2,076 Sq Ft
  • $174/SF
  • 24 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1996

  38 Wheat Ct, Shepherdstown, WV 25443

  $40k PRICE REDUCTION! This picturesque rancher is set on a quiet cul-de-sac in the Maddex Farm community with an ideal location that has all of Shepherdstown within its reach. The brick-front home is nestled into a beautifully landscaped lot that backs to trees and borders the Shepherd University Wellness Center, along with a pedestrian path that allows access to all the conveniences that

  Adam Miller Coldwell Banker Premier

  38 Wheat Ct, Shepherdstown, WV 25443
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  /32

  Est $323,387 Not Listed For Sale

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

  338 Starkeys Landing, Shepherdstown, WV 25443

  338 Starkeys Landing, Shepherdstown, WV 25443
• 

  

  /62

  $499,900

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

  1337 Cedar Ln, Shepherdstown, WV 25443

  Motivated Seller: Welcome to this custom log home on three acres, located near the Jefferson County line. Offering rustic charm with modern updates, this property features three bedrooms, two full bathrooms, a full unfinished basement, and an attached one-car garage.The wraparound porch includes both open and screened-in sections, perfect for outdoor relaxation or entertaining. Inside,

  Lesley Lopez ERA Liberty Realty

  1337 Cedar Ln, Shepherdstown, WV 25443
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  /70

  $485,000 Sold Jun 30, 2025

  • 2,772 Sq Ft
  • $175/SF
  • 13 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2007

  44 Folks Point, Shepherdstown, WV 25443

  Safe end of the Cul-De-Sac location minutes and walkable to Morgan's Grove Park and the NEW Shepherdstown Library and just a short bike or drive to downtown Shepherdstown and Shepherd University, this Colonial Hills Home is just perfect in so many ways. Home has fresh carpet installed May 2025, newer appliances, gleaming hardwood floors, an incredible plant loving sunroom, stone fireplace, and

  Adam Shively Samson Properties

  44 Folks Point, Shepherdstown, WV 25443
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  /54

  Est $408,602 Not Listed For Sale

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

  565 Maddex Farm Dr, Shepherdstown, WV 25443

  565 Maddex Farm Dr, Shepherdstown, WV 25443
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  /54

  $479,900

  • 4 Beds
  • 3.5 Baths
  • 3,482 Sq Ft

  160 Staley Dr, Shepherdstown, WV 25443

  Check out this oversized colonial with a walk out finished basement in Shepherdstown zip code on 2 acres! This home boasts over 3,000 sq ft of finished space, offering 4 bedrooms, 3.5 bathrooms, and lots more. The main level offers dining, living, and kitchen along with formal living room/office space, a half bath and mudroom! The kitchen opens up to your expansive back deck overlooking your

  Jordan Butts Burch Real Estate Group, LLC

  160 Staley Dr, Shepherdstown, WV 25443
• 

  

  /40

  $420,000 Sold Jun 30, 2025

  • 3,054 Sq Ft
  • $138/SF
  • 36 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2010

  424 Maddex Farm Dr, Shepherdstown, WV 25443

  Welcome to this amazing home in the highly desirable Maddex Farm! Conveniently located near restaurants and shopping, as well as being a short distance from downtown Historic Shepherdstown and Shepherd University campus. This spacious 4 bedroom, 2 full bath and 2 half bath home boasts an open floor plan design on the main level featuring a morning room off the kitchen, a large family room,

  Brad Lewis Greentree Associates of Shepherdstown, Inc.

  424 Maddex Farm Dr, Shepherdstown, WV 25443
• 

  

  /40

  Est $519,932 Not Listed For Sale

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

  119 Thatcher Ct, Shepherdstown, WV 25443

  119 Thatcher Ct, Shepherdstown, WV 25443
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  /13

  $124,900

  • Land
  • 0.57 Acre
  • $219,123 per Acre

  0 N Tamarac Dr Unit WVJF2019108, Shepherdstown, WV 25443

  One of a kind lot in Cress Creek/Fernbank in Shepherdstown, WV. Rare opportunity in this beautiful, meticulously maintained golf course community, and one the few lots available in Jefferson County where you can select your own builder. This highly sought-after neighborhood provides opportunity to join the Cress Creek Country Club where you have convenient access to the 18-hole golf course,

  Brian Masemer RE/MAX Real Estate Group

  0 N Tamarac Dr Unit WVJF2019108, Shepherdstown, WV 25443
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  /83

  $1,325,000 Sold Jun 27, 2025

  • 7,800 Sq Ft
  • $170/SF
  • 11 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1908

  126 E German St, Shepherdstown, WV 25443

  You are looking at one of the most iconic buildings in Historic Downtown Shepherdstown. Formerly known as Tony's Pizza and Stonewalls Underground Pub, the business shuttered in 2015. The owner has done extensive exterior and interior restoration and has decided now is the time to put the property on the market. This is your time to invest in this thriving downtown environment. Entering the

  Adam Shively Samson Properties

  126 E German St, Shepherdstown, WV 25443
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  /36

  Est $544,245 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,430 Sq Ft

  174 Canal Way, Shepherdstown, WV 25443

  174 Canal Way, Shepherdstown, WV 25443
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  /47

  $950,000

  • 3 Beds
  • 2.5 Baths
  • 3,232 Sq Ft

  1212 River Rd, Shepherdstown, WV 25443

  Welcome to the Bonnymeed Farm, a circa 1883, historically accurate, 3 bedroom, 2 and a half bath, 3,232 square feet, brick colonial on 11.7 unrestricted acres. This home has been lovingly cared for by the same owners since 1995. They are ready to move on to greener pastures and leave the rest of the finishing touches to you. Two zone propane heat and air, propane hot water, 3 working

  Brad Lewis Greentree Associates of Shepherdstown, Inc.

  1212 River Rd, Shepherdstown, WV 25443
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  /33

  $399,990 Sold Jun 23, 2025

  • 1,698 Sq Ft
  • $236/SF
  • 0 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2025

  117 Open Gate Ln, Shepherdstown, WV 25443

  Quick Move In! Main Level Primary Bedroom! Private This inviting Neuville floor plan offers the perfect blend of style & functionality, all on a single level for your comfort & convenience. Relax & enjoy the charming front porch, accentuated with tasteful stone accents. This spacious home boasts 4 bedrooms & 2 full bathrooms, providing ample space for family living. The open floor is designed

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

  117 Open Gate Ln, Shepherdstown, WV 25443
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  /78

  Est $434,093 Not Listed For Sale

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

  145 Canal Way, Shepherdstown, WV 25443

  145 Canal Way, Shepherdstown, WV 25443
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  /36

  $375,000

  • 4 Beds
  • 2.5 Baths
  • 2,880 Sq Ft

  420 Starkeys Landing, Shepherdstown, WV 25443

  Elegant Three-Level Townhome in Historic Shepherdstown, WV! Welcome to this beautifully renovated, move-in ready townhome, ideally located across from Morgan’s Grove Park and just minutes from downtown Shepherdstown’s shops, dining, and cultural charm. Offering almost 2,900 finished square feet across three thoughtfully designed levels, this 4-bedroom, 2.5-bath home blends modern luxury with

  Andrew Lowe Path Realty

  420 Starkeys Landing, Shepherdstown, WV 25443
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  /101

  $940,000 Sold Jun 20, 2025

  • 4,411 Sq Ft
  • $213/SF
  • 18 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2012

  1058 Marsh Hawk Way, Shepherdstown, WV 25443

  **HUGE PRICE IMPROVEMENT** Tucked at the end of Marsh Hawk Way, you will find a one-of-a-kind custom Cape Cod offering peace, privacy, and stunning pastoral views on 5.27 acres. Built in 2012 with meticulous attention to detail, this 4-bedroom, 4-bathroom, 4,400+ sq ft home is a true retreat for those seeking both luxury and country charm.From the moment you enter the long driveway,

  Colleen Lopez Samson Properties

  1058 Marsh Hawk Way, Shepherdstown, WV 25443
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  /38

  Est $496,790 Not Listed For Sale

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

  157 Canal Way, Shepherdstown, WV 25443

  157 Canal Way, Shepherdstown, WV 25443
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  /36

  $439,900 Open Sat 10AM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,746 Sq Ft

  168 Ella Dr, Shepherdstown, WV 25443

  Equestrian Paradise in the Sought-After Shepherdstown Area! Tucked away in a private river-access community just minutes from Shepherd University, this horse-ready haven offers the lifestyle you’ve been dreaming of. Whether you're an equestrian enthusiast or simply craving wide open spaces, this property is designed for both you and your animals.Bring your horses home and say goodbye to

  Jill Bevins Samson Properties

  168 Ella Dr, Shepherdstown, WV 25443
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  /26

  $600,000 Sold Jun 20, 2025

  • 2,589 Sq Ft
  • $232/SF
  • 74 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2001

  75 Juniper Cir, Shepherdstown, WV 25443

  Rare opportunity to find an all brick home situated on a quiet cul de sac in the Fernbank neighborhood! This all brick two story colonial features a master suite on the first floor...if desired...with a 2nd master suite on the second floor! The room downstairs would also make a great FR! Open floor plan, bright and airy, beautiful wood floors, Fr off kitchen highlighted by gas fireplace.

  Jacqueline Lewis Greentree Associates of Shepherdstown, Inc.

  75 Juniper Cir, Shepherdstown, WV 25443
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  /64

  Est $483,263 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,426 Sq Ft

  420 Maddex Dr, Shepherdstown, WV 25443

  420 Maddex Dr, Shepherdstown, WV 25443
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  /29

  $299,900

  • 4 Beds
  • 2.5 Baths
  • 2,220 Sq Ft

  115 Swearingen Way, Shepherdstown, WV 25443

  Interior town home, 3BR, 2 1/2 bath, with over 2,220 finished square feet in the highly desired community of Colonial Hills Subdivision. 3 levels: Main level with foyer, half bath, laundry, rec room with sliding glass door to rear yard, potential 4th bedroom and a 1 car garage. Second level consists of a large living room, eat-in kitchen and sunroom/breakfast room. Third level consists of the

  Brad Lewis Greentree Associates of Shepherdstown, Inc.

  115 Swearingen Way, Shepherdstown, WV 25443
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  /60

  $549,000 Sold Jun 13, 2025

  • 1,878 Sq Ft
  • $292/SF
  • 17 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1975

  1473 Steamboat Run Rd, Shepherdstown, WV 25443

  This is your chance to own a riverfront property in one of the most sought after areas of the Eastern Panhandle! Only a short drive from the quaint town of Shepherdstown, this property offers 3.46ac of mature wooded trees and views of the Potomac River glistening from your back deck. The tri-level home offers three bedrooms, 2 1/2 baths and a large vaulted ceiling family room where you can

  Tracy Palmer Samson Properties

  1473 Steamboat Run Rd, Shepherdstown, WV 25443
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  /31

  Est $484,853 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,376 Sq Ft

  100 Monument Ct, Shepherdstown, WV 25443

  100 Monument Ct, Shepherdstown, WV 25443
• 

  

  /63

  $1,199,999

  • 5 Beds
  • 3.5 Baths
  • 3,147 Sq Ft

  1132 Terrapin Neck Rd, Shepherdstown, WV 25443

  Welcome home to West Virginia’s oldest town full of immeasurable history, arts, charm, and uniqueness! This is your chance to escape all the hustle and bustle to discover this exceptional timber frame retreat-style property located in historic Shepherdstown! With almost 3,200 square feet of meticulously crafted living space, the "Felsig Platz" residence retreat is a custom-built timber frame

  Andrew Lowe Path Realty

  1132 Terrapin Neck Rd, Shepherdstown, WV 25443
• 

  

  /22

  $329,900 Sold Jun 13, 2025

  • 1,400 Sq Ft
  • $236/SF
  • 65 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1975

  92 Perth Way, Shepherdstown, WV 25443

  Price Improvement! Now available! Charming, one-level living in an established neighborhood and conveniently located to all things Shepherdstown! Offering three bedrooms and two baths, this ranch-style home has been updated and upgraded featuring new appliances, fixtures, countertops, flooring, primary bedroom deck, and a rear privacy fence. As you enter the home, take notice of the natural

  Andrew Lowe Path Realty

  92 Perth Way, Shepherdstown, WV 25443
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  /89

  Est $907,743 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,959 Sq Ft

  304 Reachcliff Dr, Shepherdstown, WV 25443

  304 Reachcliff Dr, Shepherdstown, WV 25443
• 

  

  /117

  $949,000

  • 5 Beds
  • 4 Baths
  • 4,540 Sq Ft

  301 E German St, Shepherdstown, WV 25443

  This Charming home has multiple possibilities depending on the potential new owners’ current needs or desires. The entire property adds up to five bedrooms, four full baths, and three full kitchens, plus a coveted brick driveway parking as well as a two-car detached garage. The last two owners keep the entire property as one family property. The new owner can mix and match configurations as

  Elizabeth Sager Samson Properties

  301 E German St, Shepherdstown, WV 25443
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  /61

  $350,000 Sold Jun 13, 2025

  • 2,567 Sq Ft
  • $136/SF
  • 182 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1979

  18 Woodcock Ave, Shepherdstown, WV 25443

  One owner split-level home in Mecklenburg Heights on a corner park-like lot, surrounded by trees. Through the double door entry, you will find a large foyer that connects you to the rest of the home. On the main level, you have a large living room with fireplace and dining area, eat-in kitchen and two additional exterior doors which lead to a fully fenced-in backyard. As you head up a few

  Bill Dixon Dandridge Realty Group, LLC

  18 Woodcock Ave, Shepherdstown, WV 25443
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  /55

  Est $740,335 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,744 Sq Ft

  64 Reachcliff Cir, Shepherdstown, WV 25443

  64 Reachcliff Cir, Shepherdstown, WV 25443
• 

  /2

  $139,900

  • Land
  • 2.61 Acres
  • $53,602 per Acre

  0 Comstock Dr Unit WVBE2042662, Shepherdstown, WV 25443

  Build your dream home on this beautiful lot in the desirable riverfront community of Potomac River Farms. Recently perc’d for a class 2 septic system, this property offers a quiet country setting with a Shepherdstown address while being conveniently located in Berkeley County. Perfect for those who enjoy water recreation, the community river access is just around the curve at the end of the

  Eric Exline Roger Fairbourn Real Estate LLC

  0 Comstock Dr Unit WVBE2042662, Shepherdstown, WV 25443
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  /76

  $898,750 Sold Jun 06, 2025

  • 2,629 Sq Ft
  • $342/SF
  • 9 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1780

  6531 Engle Molers Rd, Shepherdstown, WV 25443

  Step back in time and experience the charm and character of this 1780 log farmhouse—an exceptional home for those who appreciate antique craftsmanship and the stories of the past. Originally owned by George Morgan, a Revolutionary War soldier who fought alongside Gen. Washington at Piscataway in 1776, this home stood as a silent witness to generations of history. By the early 1800s, the property

  Tracy Kable Real Broker, LLC

  6531 Engle Molers Rd, Shepherdstown, WV 25443
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  /69

  Est $733,464 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,304 Sq Ft

  76 Red Blossom Cir, Shepherdstown, WV 25443

  76 Red Blossom Cir, Shepherdstown, WV 25443
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  /76

  $980,000

  • 4 Beds
  • 4 Baths
  • 3,600 Sq Ft

  50 Valentine Ct, Shepherdstown, WV 25443

  This is the one you’ve been waiting for, situated on 6.13 acres of peaceful land at the end of a quiet cul-de-sac. This stunning property offers breathtaking views of Maryland Heights, surrounded by lush woodlands, an abundance of wildlife, and 100 ft of community riverfront access. A custom-built home that combines the serenity of a country retreat with the luxury and convenience of modern

  Christina McAfee-Pierson Samson Properties

  50 Valentine Ct, Shepherdstown, WV 25443
• 

  

  /53

  $425,000 Sold Jun 04, 2025

  • 2,289 Sq Ft
  • $186/SF
  • 2 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2013

  25 Folks Point, Shepherdstown, WV 25443

  ***HIGHEST AND BEST DEADLINE MONDAY, APRIL 21st @ 9AM***This beautifully maintained 3-bedroom colonial in sought-after Colonial Hills offers modern updates and an unbeatable location. Built in 2013, this brick and vinyl-sided home sits on a landscaped quarter-acre lot in a cul-de-sac. The fenced backyard features a composite deck and a newly added cement patio off the walkout basement—perfect for

  Tracy Kable Real Broker, LLC

  25 Folks Point, Shepherdstown, WV 25443
• 

  

  /57

  Est $377,983 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,716 Sq Ft

  32 Rye Ct, Shepherdstown, WV 25443

  32 Rye Ct, Shepherdstown, WV 25443
• 

  

  /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.

  Jacqueline Lewis Greentree Associates of Shepherdstown, Inc.

  Lot 2 Martinsburg Pike, Shepherdstown, WV 25443
• 

  

  /70

  $537,400 Sold Jun 03, 2025

  • 1,734 Sq Ft
  • $310/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  1201 Morgan Grove Rd, Shepherdstown, WV 25443

  Welcome to Historic Shepherdstown, WV. Welcome home to this custom-built Cape Cod style home located just outside of Shepherdstown, WV. Situated on a little over 2 acres located just a little over a mile outside of town. Enjoy the feeling of being “away from it all” while still being close to town. This is a custom built, cedar sided home that has only ever been lived in by the original owner.

  Aaron Sholley Samson Properties

  1201 Morgan Grove Rd, Shepherdstown, WV 25443

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