Shepherdstown, WV Homes

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  $520,000 Under Contract

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

  103 E New St, Shepherdstown, WV 25443

  Historic Downtown Charm Meets Modern ComfortWelcome to 103 E New St — a distinctive historic home in the heart of Shepherdstown, West Virginia, just steps from cafes, shops, Shepherd University, and the C&O Canal National Historical Park. This thoughtfully updated 3-bedroom, 2.5-bath residence blends the warmth of original character with modern conveniences. Step inside to find rich original

  

  Tara Lowe

  Samson Properties

  (304) 632-6952

  103 E New St, Shepherdstown, WV 25443
• Explore Shepherdstown

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  /2

  $1,995 per month

  • 3 Beds
  • 2 Baths
  • 1,755 Sq Ft
  • House for Rent

  3351 Kearneysville Pike, Shepherdstown, WV 25443

  3351 Kearneysville Pike, Shepherdstown, WV 25443
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  /3

  $339,000 Sold Nov 24, 2025

  • 1,400 Sq Ft
  • $242/SF
  • 8 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1960

  71 Cherry Ln, Shepherdstown, WV 25443

  Welcome to this delightful all-brick ranch-style home in Shepherdstown. Upon entering, you'll be greeted by charming hardwood floors and a striking brick fireplace. The spacious, updated windows fill the interior with an abundance of natural light. Adjacent to the living and dining areas is the kitchen, making it easy to host and entertain your guests. Down the hallway, you'll discover three cozy

  Brittany Lowe Burch Real Estate Group, LLC

  71 Cherry Ln, Shepherdstown, WV 25443
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  /10

  Est $192,601 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 740 Sq Ft

  114 College St, Shepherdstown, WV 25443

  114 College St, Shepherdstown, WV 25443
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  /39

  $309,000

  • 3 Beds
  • 4 Baths
  • 2,720 Sq Ft

  51 Swearingen Way, Shepherdstown, WV 25443

  Welcome to this Sun-Drenched and Spacious Townhome with Serene Wooded Views, 3 bedrooms, 2 full bathrooms, 2 half baths, and durable, stylish flooring. Enjoy Peace of Mind with Recent Updates. The deck was freshly painted, and a new heat pump (2019), disposal and microwave were recently installed. Comcast cable and Xfinity are available. Enjoy the perfect blend of town and country! This home is

  

  Richard Kendall

  Snyder Bailey & Associates

  (304) 971-4952

  51 Swearingen Way, Shepherdstown, WV 25443
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  /23

  $1,400 per month

  • 2 Beds
  • 1 Bath
  • 875 Sq Ft
  • House for Rent

  130 E German St Unit 201, Shepherdstown, WV 25443

  Offering a rare and unique opportunity to rent one of the nicest 2 bedroom apartments in down town Historic Shepherdstown. A great place for the adult working professional. 130 East German, Suite 201: 2 BR, 1 BA, totally restored and like new, wood floors, exposed brick living room walls, like new stainless electric range, range hood, & fridge, large master bedroom with dual closets, smaller

  Brad Lewis Greentree Associates of Shepherdstown, Inc.

  130 E German St Unit 201, Shepherdstown, WV 25443
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  /13

  $124,000 Sold Nov 21, 2025

  • Land
  • 0.57 Acre
  • $217,544 per Acre

  • 67 Days On Market

  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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  /41

  Est $555,062 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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  /54

  $649,900

  • 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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  /17

  $2,500 per month

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft
  • House for Rent

  215 Maddex Square Dr, Shepherdstown, WV 25443

  Presenting another quality 4 BR, 2 1/2 bath rental home in the highly desired Maddex Farm community. Hardwood floors throughout most of first level, new stainless appliances, gas fireplace in the large living room, breakfast room off kitchen, master suite with tray ceiling, walk-in closets, and deluxe bath with soaking tub and shower. Nice rear deck with partially fenced in back yard. Full,

  Brad Lewis Greentree Associates of Shepherdstown, Inc.

  215 Maddex Square Dr, Shepherdstown, WV 25443
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  /54

  $459,900 Sold Nov 21, 2025

  • 3,482 Sq Ft
  • $132/SF
  • 53 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2003

  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
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  /57

  Est $660,387 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

  $249,900 Pending

  • 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 nice

  Adam Shively Samson Properties

  46 Finch Ln, Shepherdstown, WV 25443
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  /7

  $950 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  114 S Princess St Unit 3, Shepherdstown, WV 25443

  Second floor, one bedroom, one bath apartment with galley kitchen and separate living room. Walk to Shepherd University or many other downtown destinations. Building main entrance secured with key pad entry.

  Val Nicole Clark Realty FC, LLC

  114 S Princess St Unit 3, Shepherdstown, WV 25443
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  /54

  $713,000 Sold Nov 21, 2025

  • 2,717 Sq Ft
  • $262/SF
  • 35 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2025

  114 Southpaw Ln, Shepherdstown, WV 25443

  Ready Now!!! 3.57 +/- acre lot with no HOA. Located in a convenient yet rural setting and an ideal commuter location. Your new quality built home will fit perfectly and includes the following - 4 bedrooms with 3.5 baths ranch farm house style home. Quality construction nicely upgraded with full kitchen appliance package, quartz counters, luxury vinyl plank flooring, carpet, soft close cabinets,

  Rick Boswell Gain Realty

  114 Southpaw Ln, Shepherdstown, WV 25443
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  /56

  Est $753,395 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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  /60

  $499,000

  • 4 Beds
  • 2 Baths
  • 2,048 Sq Ft

  207 W High St, Shepherdstown, WV 25443

  Welcome to 207 W High Street located in beautiful and historic Shepherdstown, West Virginia. With Shepherdstown being established in 1762 and one of the oldest towns in West Virginia, this 1790 built home plays a strong role in the community and holds historical significance. The Shepherdstown Historic District was established and added to the National Register of Historic Places in 1973, with a

  Dana Ashlock Samson Properties

  207 W High St, Shepherdstown, WV 25443
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  /10

  $1,050 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  114 S Princess St Unit 1, Shepherdstown, WV 25443

  Ground level apartment with separate entrance in the heart of Shepherdstown, WV. Walk to Shepherd University or many other downtown destinations. This unit features high ceilings and lots of charm. One bedroom, one bath with eat-in kitchen and separate living room. Key pad entry at main entrance.

  Val Nicole Clark Realty FC, LLC

  114 S Princess St Unit 1, Shepherdstown, WV 25443
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  /36

  $242,564 Sold Nov 17, 2025

  • 2,679 Sq Ft
  • $91/SF
  • 9 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1980

  603 Persimmon Ln, Shepherdstown, WV 25443

  Located on 1.5 secluded acres in the desirable Shepherdstown area of Jefferson County, this spacious 4 bedroom, 2.5 bath home offers approximately 2,679 sq. ft. of living space. The kitchen features natural wood cabinets, hard surface countertops, stainless steel appliances, and a farmhouse style sink. Adjacent to the kitchen area is a sunroom with abundant windows, providing plenty of natural

  David Ottey Samson Properties

  603 Persimmon Ln, Shepherdstown, WV 25443
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  /31

  Est $536,129 Not Listed For Sale

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

  50 Lamar Ln, Shepherdstown, WV 25443

  50 Lamar Ln, Shepherdstown, WV 25443
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  /70

  $574,900

  • 4 Beds
  • 2 Baths
  • 3,582 Sq Ft

  7765 Martinsburg Pike, Shepherdstown, WV 25443

  Experience the charm of this immaculately preserved 1912 stone house, set on over 2 acres in close proximity to historic Shepherdstown. This spacious 4-bedroom, 2-bathroom home features tall ceilings, hardwood floors, and a wide center hall on the main level. You'll also find two large bedrooms, a study, a cozy living room, a full bath, and a convenient laundry area. At the back of the home, the

  Bill Dixon Dandridge Realty Group, LLC

  7765 Martinsburg Pike, Shepherdstown, WV 25443
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  /9

  $900 per month

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • Condo for Rent

  114 S Princess St Unit 5, Shepherdstown, WV 25443

  Cute third floor, one bedroom, one bath apartment with separate living room. Walk to Shepherd University or many other downtown destinations. Building main entrance secured with key pad entry.

  Val Nicole Clark Realty FC, LLC

  114 S Princess St Unit 5, Shepherdstown, WV 25443
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  /42

  $562,000 Sold Nov 17, 2025

  • 2,437 Sq Ft
  • $231/SF
  • 33 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2015

  50 Hartzell Dr, Shepherdstown, WV 25443

  This one-owner, semi-detached home offers timeless appeal with the ease of one-level living and a spacious open floor plan. Beautifully upgraded throughout, the home features 3 bedrooms, 3 full baths, and a versatile upper loft—perfect for guests or a private home office. The main level includes a convenient laundry room, a bright and airy living area, and seamless access to the outdoors. Enjoy

  Paula Miller Coldwell Banker Premier

  50 Hartzell Dr, Shepherdstown, WV 25443
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  /69

  Est $558,824 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,239 Sq Ft

  97 Heritage Dr, Shepherdstown, WV 25443

  97 Heritage Dr, Shepherdstown, WV 25443
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  /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
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  /14

  $2,400 per month

  • 4 Beds
  • 2.5 Baths
  • 3,241 Sq Ft
  • House for Rent

  24 Butcher Ct, Shepherdstown, WV 25443

  Maddex neighborhood of Shepherdstown, this home is a spacious, light filled open design, two story 4 bdrm, 2 1/2 bath, double car attached garage. The location, within two min. drive of historic Shepherdstown, a short walk to the University, cultural events and surrounding recreation areas galore. This sought after location, plenty of large high windows all around, mature trees, landscaping and a

  Gregorio Garcia Samson Properties

  24 Butcher Ct, Shepherdstown, WV 25443
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  /29

  $390,000 Sold Nov 14, 2025

  • 2,136 Sq Ft
  • $183/SF
  • 3 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1975

  155 Meadowlark Ln, Shepherdstown, WV 25443

  Welcome home to this beautifully updated property in the charming town of Shepherdstown, WV. Boasting over 2,100 square feet of living space, this spacious residence features 4 generous bedrooms and 2.5 bathrooms, offering ample room for both relaxation and entertainment. The home has been completely renovated with modern finishes, including new windows, stainless appliances, granite countertops,

  Andrew Lowe Path Realty

  155 Meadowlark Ln, Shepherdstown, WV 25443
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  /34

  Est $347,664 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
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  /46

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,006 Sq Ft

  104 Stonehouse Ln, Shepherdstown, WV 25443

  New Listing in Shepherdstown, West Virginia!Welcome home to this charming rancher nestled on 1.8 acres in beautiful Shepherdstown. Enjoy the ease of one-level living with the added potential of a full, walk-out basement—perfect for future expansion or storage. Inside, you’ll find all NEW gorgeous LVP flooring, new carpets in bedrooms, Upgraded kitchen & new appliances, a cozy fireplace area

  Kara Burnett Samson Properties

  104 Stonehouse Ln, Shepherdstown, WV 25443
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  /21

  $2,500 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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  /86

  $965,000 Sold Nov 12, 2025

  • 3,600 Sq Ft
  • $268/SF
  • 19 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2011

  50 Valentine Ct, Shepherdstown, WV 25443

  If you want peace and quiet, seclusion, and yet be only 3 miles from Shepherdstown then this is a must see. A well maintained Custom built 4 bedroom 3700 sqft home on 6+ acres just minutes from Historic Shepherdstown and the POTOMAC RIVER. This one has everything you are looking for, starting with the wrap-around covered porch to enjoy your morning coffee while watching the sunrise to finishing

  James Amick RE/MAX Roots

  50 Valentine Ct, Shepherdstown, WV 25443
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  /85

  Est $761,250 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
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  /49

  $585,000

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

  79 Leisure Way, Shepherdstown, WV 25443

  COMING SOON! Heads up on this over 4400 sq.ft. two story with a finished basement! Freshly painted throughout, almost all new carpeting and vinyl; and beautifully refinished hardwood floors. Few things left for your finishing touches. Celestory windows in great room with high ceilings beckon you in PLUS an eat-in kitchen and formal dining area or use as an office space. Lower level student or

  Jacqueline Lewis Greentree Associates of Shepherdstown, Inc.

  79 Leisure Way, Shepherdstown, WV 25443
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  /51

  $580,000 Sold Nov 07, 2025

  • 2,235 Sq Ft
  • $260/SF
  • 33 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2025

  328 Comstock Dr, Shepherdstown, WV 25443

  READY NOW ! 2.74-acres located in the Potomac River Farms subdivision. It is within walking distance of community access to the Potomac River and about 10 minutes from Shepherdstown's downtown area, known for its dining and shopping options. The property also features a 12x36 horse barn with electric previously used for two horses.Home Features:Craftsman-style ranch home offers

  Rick Boswell Gain Realty

  328 Comstock Dr, Shepherdstown, WV 25443
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  /51

  Est $704,788 Not Listed For Sale

  • Studio
  • 3,513 Sq Ft

  305 W German St, Shepherdstown, WV 25443

  305 W German St, Shepherdstown, WV 25443
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  /129

  $569,900

  • 4 Beds
  • 3 Baths
  • 2,460 Sq Ft

  79 Chandler Dr, Shepherdstown, WV 25443

  Beautifully Renovated Retreat on 3 Acres in Oakleigh Acres – A Rare Shepherdstown Find with four bedrooms and 3 bathrooms! Welcome to your dream home—a fully renovated, move-in-ready gem tucked away on three-level acres in the highly sought-after Oakleigh Acres community of Shepherdstown, WV. This property delivers the perfect fusion of sleek modern style and serene country living, just minutes

  Lynn Ober Real Estate Innovations

  79 Chandler Dr, Shepherdstown, WV 25443
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  /84

  $610,000 Sold Nov 07, 2025

  • 4,597 Sq Ft
  • $133/SF
  • 61 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1994

  211 Heritage Dr, Shepherdstown, WV 25443

  This stunning mostly all brick Colonial offers over 4,000 finished square feet of living space. Nestled on 1.41 acres and backing to trees for added privacy, located in a quiet cul-de-sac, the home boasts extensive landscaping, a paved driveway, and a 2-car garage. Relax or entertain on the large back deck, perfect for gatherings with friends and family. Inside, you'll find 4 generously sized

  Brandi Marcum Pearson Smith Realty, LLC

  211 Heritage Dr, Shepherdstown, WV 25443
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  /88

  Est $642,475 Not Listed For Sale

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

  1899 Trough Rd, Shepherdstown, WV 25443

  1899 Trough Rd, Shepherdstown, WV 25443
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  /62

  $550,000

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

  185 Shepherd Ln, Shepherdstown, WV 25443

  Welcome to 185 Shepherd Lane, a charming and spacious home just minutes from downtown Shepherdstown, WV. Situated on 2.5076 acres in a peaceful, established neighborhood with large lots, this 4-bedroom, 2.5-bath home offers both comfort and opportunity. A covered front porch welcomes you into the main level, which features a formal living room and dining room (both with beautiful hardwood floors)

  Liz McDonald Dandridge Realty Group, LLC

  185 Shepherd Ln, Shepherdstown, WV 25443
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  /47

  $215,000 Sold Oct 31, 2025

  • 1,408 Sq Ft
  • $153/SF
  • 7 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1976

  24 Cavaland Terrace, Shepherdstown, WV 25443

  Final and Best offer deadline is Tuesday, 10/7 by 9 a.m. Step into opportunity with this charming townhome just outside the historic town of Shepherdstown! Offering 2 bedrooms, 1.5 baths, and 1,408 square feet of living space, this property is ready for your personal touch and updates to make it shine. Built in 1976, the home features a spacious living room and a kitchen/dining combo. A partial

  Cheryl Yates ERA Liberty Realty

  24 Cavaland Terrace, Shepherdstown, WV 25443

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