Shepherdstown, WV Homes

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  /6

  $54,990 Under Contract

  • Land
  • 0.13 Acre
  • $423,000 per Acre

  110 College St, Shepherdstown, WV 25443

  Unique buildable lot only blooks to Shepherd University and downtown Shepherdstown. Quiet street located in the Historic Distric of Shepherdstown. Well established neighborhood. Possibility of 2 townhomes could be built on lot. Please contact the City of Shepherdstown to verify possibilities. Go and Show

  

  Robert Bir

  Samson Properties

  (304) 318-7028

  110 College St, Shepherdstown, WV 25443
• 

  Explore Shepherdstown

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  /21

  $2,650 per month

  • 4 Beds
  • 4 Baths
  • 3,302 Sq Ft
  • House for Rent

  72 Maddex Farm Dr, Shepherdstown, WV 25443

  Absolutely immaculate Victoria Model in the highly desired Maddex Farm community. Like new carpet through out, walls and ceilings were just freshly painted. Wood floors in foyer, vinyl in kitchens and baths, granite counters, new stainless appliances, partially finished walk-out basement with built in book cases, and half bath, Master suite with whirlpool tub/dual vanity/walk-in closet.

  Brad Lewis Greentree Associates of Shepherdstown, Inc.

  72 Maddex Farm Dr, Shepherdstown, WV 25443
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  /28

  $439,990 Sold Sep 18, 2025

  • 2,200 Sq Ft
  • $200/SF

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  17 Open Gate Ln, Shepherdstown, WV 25443

  Corner Lot! 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 Grove Park and just down the street from Downtown Shepherdstown!

  D.R. Horton

  17 Open Gate Ln, Shepherdstown, WV 25443
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  /39

  Est $418,787 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,940 Sq Ft

  16 Monument Ct, Shepherdstown, WV 25443

  16 Monument Ct, Shepherdstown, WV 25443
• 

  

  

  /35

  $399,900

  • 3 Beds
  • 3 Baths
  • 1,680 Sq Ft

  21 Rock Spring Ln, Shepherdstown, WV 25443

  This lovely 3 bedroom 3 bath Cape Cod sits just outside of Shepherdstown. There is a large driveway for ample parking, includes a new carport with rear storage for yard tools. Inside the home you have a spacious living room with laminate flooring and ceiling fan. The woodstove features a stone hearth and surround with built-in shelving. The living room opens to the large kitchen. Here you have a

  

  Matt Ridgeway

  RE/MAX Real Estate Group

  (304) 317-3087

  21 Rock Spring Ln, Shepherdstown, WV 25443
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  /54

  $452,500 Sold Sep 18, 2025

  • 2,236 Sq Ft
  • $202/SF
  • 69 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1978

  95 Devon Way, Shepherdstown, WV 25443

  This newly renovated home on almost an acre is situated in Chaplines Choice. The home features 3 bedrooms, 3 bathrooms, and a flex room in the basement that is perfect for a home office, gym or whatever you desire. As you approach the home you will love the exterior which includes new windows, vinyl siding, architectural shingle roof and exterior doors. Upon entering the front door, you will

  Nicole Bonner Pearson Smith Realty, LLC

  95 Devon Way, Shepherdstown, WV 25443
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  /23

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,698 Sq Ft

  169 Lyon Ridge Rd, Shepherdstown, WV 25443

  169 Lyon Ridge Rd, Shepherdstown, WV 25443
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  /54

  $699,900

  • 4 Beds
  • 4 Baths
  • 3,060 Sq Ft

  150 Morgana Dr, Shepherdstown, WV 25443

  This all-brick colonial is a true classic. It sits of over 3 and 1/2 acres of Jefferson County's finest land. Your large lot is surrounded with trees for tons of privacy. Once you clear the trees on your long driveway you will be taken away by this home's curb appeal. A beautiful concrete path leads you from the driveway, passed the manicured landscaping, to the lovely front porch. Can't you just

  

  Matt Ridgeway

  RE/MAX Real Estate Group

  (304) 898-1658

  150 Morgana Dr, Shepherdstown, WV 25443
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  /40

  $460,000 Sold Sep 18, 2025

  • 2,279 Sq Ft
  • $202/SF
  • 101 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1999

  325 Chandler Dr, Shepherdstown, WV 25443

  Welcome home to this beautiful 3 bedroom, 2.5 bath colonial, perfectly tucked away on 3 private acres just minutes from the charm of downtown Shepherdstown. This home offers the ideal blend of peace, privacy, and convenience. The main level features a bright and airy family room with expansive windows, seamlessly flowing into the inviting kitchen equipped with stainless steel appliances, a

  Liz Owings RE/MAX Roots

  325 Chandler Dr, Shepherdstown, WV 25443
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  /10

  Est $186,329 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 740 Sq Ft

  114 College St, Shepherdstown, WV 25443

  114 College St, Shepherdstown, WV 25443
• 

  

  /21

  $145,000

  • Land
  • 5 Acres
  • $29,000 per Acre

  Lot 61-A Scrabble Rd, Shepherdstown, WV 25443

  5 Acres of Prime Land – Shepherdstown, WV just over onto the Berkeley County border.Looking to build your dream home or invest in a peaceful getaway? This beautiful 5.002-acre lot—Lot 61-A of the Snook Subdivision—offers the perfect blend of seclusion and accessibility in scenic Berkeley County. Property Highlights:5.002 Acres nestled among mature trees and gently rolling

  

  Tara Lowe

  Samson Properties

  (304) 381-1363

  Lot 61-A Scrabble Rd, Shepherdstown, WV 25443
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  /83

  $545,000 Sold Sep 17, 2025

  • 4,774 Sq Ft
  • $114/SF
  • 3 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2005

  85 Butcher Ct, Shepherdstown, WV 25443

  Located in the established Maddex Farm subdivision in Shepherdstown, this thoughtfully renovated 4-bedroom, 3.5-bath colonial offers spacious living and quality upgrades just minutes from town. With a main-level primary suite, finished walkout basement, and beautifully landscaped fenced yard, this home is designed for both comfort and functionality.Inside, hardwood floors flow throughout

  Tracy Kable Real Broker, LLC

  85 Butcher Ct, Shepherdstown, WV 25443
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  /41

  Est $569,775 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,144 Sq Ft

  277 Shveda Way, Shepherdstown, WV 25443

  277 Shveda Way, Shepherdstown, WV 25443
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  /13

  $147,000

  • Land
  • 2.04 Acres
  • $72,059 per Acre

  0 Heather Ln, Shepherdstown, WV 25443

  Nestled along the Potomac River, This attractive 2 acre lot is located less than 300 yards from the Potomac River in and it has been PERC for a 3 bedroom.Steamboat Run, a beautiful park-like wooded community with river access, hiking trails,picnic area, and a 16 acre community meadow. The community is only 3 miles fromscenic Shepherdstown, WV, and Shepherd University. There is an

  

  Mercedes Prohaska

  Coldwell Banker Premier

  (304) 909-7618

  0 Heather Ln, Shepherdstown, WV 25443
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  /52

  $465,000 Sold Sep 17, 2025

  • 2,036 Sq Ft
  • $228/SF
  • 66 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1966

  23 Fairmont Ave, Shepherdstown, WV 25443

  Owned Solar Panels, EV Charger, New Water Heater, Easy One-Level Living with Expansive Basement in Historic Shepherdstown23 Fairmont Avenue is a solid all-brick ranch offering the simplicity of single-level living paired with the flexibility of a full, unfinished basement. Just minutes from downtown Shepherdstown, this home is perfect for buyers who value space, low maintenance, and

  Tara Lowe Samson Properties

  23 Fairmont Ave, Shepherdstown, WV 25443
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  /57

  Est $669,325 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,860 Sq Ft

  224 Shveda Way, Shepherdstown, WV 25443

  224 Shveda Way, Shepherdstown, WV 25443
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  /48

  $600,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 2,540 Sq Ft

  306 Tinsley Cir, Shepherdstown, WV 25443

  Welcome to 306 Tinsley Circle, a beautifully renovated home tucked away in one of Shepherdstown’s most desirable neighborhoods. The seller is relocating for work, offering you the rare opportunity to own a freshly updated property that combines modern elegance with timeless charm. Stunning Sunroom AdditionThe centerpiece of this home is the enormous sunroom, showcasing soaring

  

  Tara Lowe

  Samson Properties

  (304) 355-5207

  306 Tinsley Cir, Shepherdstown, WV 25443
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  /57

  $585,000 Sold Sep 12, 2025

  • 4,884 Sq Ft
  • $120/SF
  • 41 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2005

  164 Butcher Ct, Shepherdstown, WV 25443

  Welcome to 164 Butcher Court, a well-appointed and beautifully maintained 4-bedroom, 3.5-bath colonial offering nearly 5,000 square feet of finished living space, situated on a large .37-acre lot at the end of a quiet cul-de-sac with no through traffic in the peaceful Maddex Farms community of Shepherdstown. This spacious and meticulously cared for home combines thoughtful design, inviting

  Carolyn Young Samson Properties

  164 Butcher Ct, Shepherdstown, WV 25443
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  /56

  Est $765,164 Not Listed For Sale

  • 7 Beds
  • 2.5 Baths
  • 3,168 Sq Ft

  214 W German St, Shepherdstown, WV 25443

  214 W German St, Shepherdstown, WV 25443
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  /64

  $375,000 Under Contract

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

  501 Maddex Farm Dr, Shepherdstown, WV 25443

  Welcome to 501 Maddex Farm Drive—Shepherdstown charm meets modern convenience!This beautifully maintained 3-bedroom, 2.5-bath colonial is nestled in the heart of the highly desirable Maddex Farm neighborhood, just minutes from historic downtown Shepherdstown, Shepherd University, and the scenic C&O Canal.The home features an open-concept main level with abundant natural light, updated

  

  Tara Lowe

  Samson Properties

  (304) 459-2609

  501 Maddex Farm Dr, Shepherdstown, WV 25443
• 

  

  /70

  $625,000 Sold Sep 04, 2025

  • 3,626 Sq Ft
  • $172/SF
  • 111 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2001

  135 Deep Woods Trail, Shepherdstown, WV 25443

  Welcome home to this spacious and versatile 5-bedroom property, ideally nestled in a serene, partially wooded setting just minutes from historic Shepherdstown. Located in a quiet, smaller subdivision near Morgan’s Grove Park, this exceptional home offers the perfect blend of privacy, comfort, and convenience on an extraordinary 3.25 acre lot.The main level features a desirable primary

  Larry DeMarco Century 21 Modern Realty Results

  135 Deep Woods Trail, Shepherdstown, WV 25443
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  /31

  Est $574,838 Not Listed For Sale

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

  50 Lamar Ln, Shepherdstown, WV 25443

  50 Lamar Ln, Shepherdstown, WV 25443
• 

  

  /31

  $417,990 New Construction

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

  Deerfield Plan at Tollhouse Woods, Shepherdstown, WV 25443

  The Deerfield is a thoughtfully designed two-story house with four bedrooms and two-and-a-half baths. The kitchen features a walk-in pantry and island. That island includes a sink, making it perfect for food preparation, and has plenty of room for stools, so you can entertain. The kitchen looks out over the open-concept dining area and great room. All four bedroom are upstairs along with the

  

  D.R. Horton

  Builder

  19 Tollhouse Way Unit 36203408, Shepherdstown, WV 25443
• 

  

  /41

  $438,000 Sold Sep 02, 2025

  • 2,374 Sq Ft
  • $184/SF
  • 23 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2007

  132 Thatcher Ct, Shepherdstown, WV 25443

  ****$5,000.00 IN CLOSING COST **** Tucked into the desirable Maddex Farms community, this spacious 4-bedroom, 3.5-bath home offers room to grow and roam in an unbeatable location. Just minutes from downtown Shepherdstown and Shepherd University, you’ll love the walkability to dining, shopping, and local charm. The main level includes a bright and open morning room just off the large, updated

  Deb Crosley Keller Williams Realty

  132 Thatcher Ct, Shepherdstown, WV 25443
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  /34

  Est $353,092 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,796 Sq Ft

  262 Old Martinsburg Rd, Shepherdstown, WV 25443

  262 Old Martinsburg Rd, Shepherdstown, WV 25443
• 

  

  /48

  $259,900

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  46 Finch Ln, Shepherdstown, WV 25443

  Adorable Ranch style home set back to the trees and privacy in the rear of Mecklenburg Heights. This quiet community is one of the few affordable options in the Shepherdstown zip code. Home has newer HVAC, newer roof, upgraded kitchen, new LVP Floors, refurbished bathroom, and is freshly painted. The rear yard is a true private retreat oasis. Nice storage shed with electric could make a very

  Adam Shively Samson Properties

  46 Finch Ln, Shepherdstown, WV 25443
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  /34

  $197,000 Sold Aug 26, 2025

  • 786 Sq Ft
  • $251/SF
  • 68 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1950

  111 Ray St, Shepherdstown, WV 25443

  Imagine owning your own piece of Shepherdstown—charming, walkable, and full of character. Just blocks from Shepherd University and downtown, 111 Ray Street is both cozy and incredibly functional. This updated 2-bedroom cottage offers flexible living space and thoughtful design in a compact footprint.Inside, you’ll find durable luxury vinyl plank flooring, a welcoming living room, and a crisp

  Liz McDonald Dandridge Realty Group, LLC

  111 Ray St, Shepherdstown, WV 25443
• 

  

  /85

  Est $779,809 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,743 Sq Ft

  106 N Duke St, Shepherdstown, WV 25443

  106 N Duke St, Shepherdstown, WV 25443
• 

  

  /25

  $464,990 New Construction

  • 4 Beds
  • 3 Baths
  • 1,748 Sq Ft

  101 Open Gate Ln, Shepherdstown, WV 25443

  The beautiful Bristol floorplan offers a front porch-1-level living at its best, the open floor plan offers great entertaining space and 3 bedrooms and 2 full baths on this first level, the kitchen is a dream to cook your family meals huge kitchen island and separate dining area and if you want to take your meal outside then plan to do that on the beautiful covered back porch. The 2nd level

  

  D.R. Horton

  Builder

  101 Open Gate Ln, Shepherdstown, WV 25443
• 

  

  /53

  $476,200 Sold Aug 22, 2025

  • 3,722 Sq Ft
  • $128/SF
  • 27 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2006

  308 Maddex Dr, Shepherdstown, WV 25443

  Location is paramount! Nestled just a short stroll from downtown Shepherdstown and the esteemed Shepherd University, this exquisite four-bedroom, 2.5 bath home awaits your arrival. Take a leisurely walk into town, the local food store or to Shepherd University. With its inviting open floor plan, the expansive family room and charming morning room create a warm and welcoming atmosphere. The

  Suzanne Frund Samson Properties

  308 Maddex Dr, Shepherdstown, WV 25443
• 

  

  /39

  Est $375,910 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,530 Sq Ft

  8709 Shepherdstown Pike, Shepherdstown, WV 25443

  8709 Shepherdstown Pike, Shepherdstown, WV 25443
• 

  

  /28

  $399,990 New Construction

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

  36 Open Gate Ln, Shepherdstown, WV 25443

  Quick Move In on a Corner Lot! 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 Grove Park and just down the street from Downtown Shepherdstown!

  

  D.R. Horton

  Builder

  36 Open Gate Ln, Shepherdstown, WV 25443
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  /140

  $810,000 Sold Aug 15, 2025

  • 3,459 Sq Ft
  • $234/SF
  • 64 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1898

  213 W High St, Shepherdstown, WV 25443

  Welcome to 213 W High Street! This beautifully preserved 2-story residence rests on a DOUBLE, corner lot in the Historic District. The charming home showcases original architectural elements and offers the perfect balance of comfort, style, and history. Its plaster walls, wood floors and double-hung wood windows have been lovingly maintained. It exudes historical character as you enter through

  Errika Best Greentree Associates of Shepherdstown, Inc.

  213 W High St, Shepherdstown, WV 25443
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  /51

  Est $658,806 Not Listed For Sale

  • Studio
  • 3,513 Sq Ft

  305 W German St, Shepherdstown, WV 25443

  305 W German St, Shepherdstown, WV 25443
• 

  

  /59

  $599,900

  • 4 Beds
  • 3 Baths
  • 2,144 Sq Ft

  278 Chandler Dr, Shepherdstown, WV 25443

  Nestled on a private lot in the serene Oakleigh subdivision, this charming contemporary home offers a perfect blend of lifestyle and functionality. Set on three acres with several outbuildings, including a greenhouse, the expansive garden beds, babbling koi pond, and colorful foliage spread across the property are simply beautiful. The home features four spacious bedrooms and three full

  Adam Miller Coldwell Banker Premier

  278 Chandler Dr, Shepherdstown, WV 25443
• 

  

  /30

  $508,490 Sold Aug 11, 2025

  • 2,401 Sq Ft
  • $212/SF
  • 0 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2025

  43 Open Gate Ln, Shepherdstown, WV 25443

  Beautiful Rancher 4 bedroom and 3 full bath home on a corner home site in Shepherdstown WV, the home offers 3 bedrooms on the first level and 2 full baths and then walk up to a 2nd level that opens to a large finished area and includes a bedroom and full bath. This home offers a covered back porch for summer entertainment. Beautiful open floor plan with lots of windows for natural light and 2

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

  43 Open Gate Ln, Shepherdstown, WV 25443
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  /88

  Est $637,838 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,040 Sq Ft

  1899 Trough Rd, Shepherdstown, WV 25443

  1899 Trough Rd, Shepherdstown, WV 25443
• 

  

  /53

  $635,000

  • 5 Beds
  • 3.5 Baths
  • 4,850 Sq Ft

  27 Costen Cir, Shepherdstown, WV 25443

  From the moment you arrive the curb appeal makes an impression. In the beautiful neighborhood of Willow Springs Acres, this corner lot stretches across .93 acres, with fresh landscaping and raised decorative brick flower beds just waiting to showcase your favorite blooms. The fully fenced backyard is a private oasis where kids and pets can play freely, complete with a wooden play set and

  Andrew Woods EXP Realty

  27 Costen Cir, Shepherdstown, WV 25443
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  /44

  $620,000 Sold Aug 08, 2025

  • 2,938 Sq Ft
  • $211/SF
  • 87 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2013

  12 Briar Mountain Dr, Shepherdstown, WV 25443

  SELLERS HAVE AUTHORIZED A NEW PRICE! YOU HAVE TO SEE THIS HOME TO BELIEVE IT'S VALUE! Simply charming, three bedroom cape cod is perched into the hillside off a green at the neighboring Cress Creek Golf Course. Located in the sought-after North Hills at Cress Creek - where golf, swimming, dining, and the Potomac River lifestyle await, this home has it all! Hardwood floors stretch through the

  Adam Miller Coldwell Banker Premier

  12 Briar Mountain Dr, Shepherdstown, WV 25443
• 

  

  /40

  Est $1,346,500 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,584 Sq Ft

  1901 Trough Rd, Shepherdstown, WV 25443

  1901 Trough Rd, Shepherdstown, WV 25443

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