Shepherdstown, WV Homes

/30
$512,490 New Construction
- 5 Beds
- 3 Baths
- 2,511 Sq Ft
126 Riderwood Way, Shepherdstown, WV 25443

Private Back to Trees Homesite! Walkout Basement and Finished Rec Room! Sits on nearly a 1/3 acre homesite with great views! Complete with a main level bedroom and full bath, great for guests. This 2 Story single family home marries features and affordability and comes with everything included. 5 Bedrooms a 2nd floor loft, LVP floors in the main living spaces, included kitchen appliances, granite

D.R. Horton Builder

126 Riderwood Way, Shepherdstown, WV 25443
/76
$860,000 Sold Jul 21, 2025

100 W New St, Shepherdstown, WV 25443
- 3 Beds
- 2.5 Baths
- 3,957 Sq Ft
- Built 1789
Last Sold Summary
- $217/SF
- 10 Days On Market
Current Estimated Value $745,000

Last Listing Agent Derek Eisenberg Continental Real Estate Group

100 W New St, Shepherdstown, WV 25443

/18
Est $387,481 Not Listed For Sale

306 W German St, Shepherdstown, WV 25443
- 1 Bed
- 1.5 Baths
- 1,552 Sq Ft
- Built 1840
306 W German St, Shepherdstown, WV 25443

Last Sold Summary
- 14% Above List Price
- $219/SF
- 4 Days On Market
Last Sold Price $340,000

Last Listing Agent Wendy Williams Greentree Associates of Shepherdstown, Inc.

/5
$659,999 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
/73
$310,000 Sold Mar 12, 2025

796 Dam 4 Rd, Shepherdstown, WV 25443
- 3 Beds
- 2 Baths
- 2,200 Sq Ft
- Built 1900
Last Sold Summary
- $141/SF
- 82 Days On Market
Current Estimated Value $346,153

Last Listing Agent Sarah Combs Hoffman Realty

796 Dam 4 Rd, Shepherdstown, WV 25443

/36
Not Listed For Sale

0 Steamboat Run Rd Unit WVJF2015442, Shepherdstown, WV 25443
0 Steamboat Run Rd Unit WVJF2015442, Shepherdstown, WV 25443

Last Sold Summary
Last Sold Price $310,000

Last Listing Agent Liz McDonald Dandridge Realty Group, LLC

/8
$497,990 New Construction
- 4 Beds
- 3 Baths
- 2,401 Sq Ft
BRISTOL Plan at Tollhouse Woods, Shepherdstown, WV 25443

Our brand-new ranch plan with a loft: The Bristol! This style home offers prime main level living. On the 2nd floor there is a spacious loft area with a bedroom and full bath. In total there are 4 bedrooms, 3 full baths and a generous 2 car garage. This designer kitchen is equipped with stainless steel appliances, multi cycle dishwasher, disposal, range and microwave with Aristokraft kitchen

D.R. Horton Builder

19 Tollhouse Way Unit 36203411, Shepherdstown, WV 25443
/40
$420,000 Sold Jun 30, 2025

424 Maddex Farm Dr, Shepherdstown, WV 25443
- 4 Beds
- 4 Baths
- 3,054 Sq Ft
- Built 2010
Last Sold Summary
- $138/SF
- 36 Days On Market
Current Estimated Value $437,778

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

424 Maddex Farm Dr, Shepherdstown, WV 25443

/19
Not Listed For Sale

42 Mole Ct, Shepherdstown, WV 25443
- 4 Beds
- 3.5 Baths
- 2,982 Sq Ft
42 Mole Ct, Shepherdstown, WV 25443

Last Sold Summary
- $224/SF
- 24 Days On Market
Last Sold Price $666,779

Last Listing Agent Kevin Coomler ERA Liberty Realty

/42
$515,000 Under Contract
- 3 Beds
- 2.5 Baths
- 2,006 Sq Ft
104 Stonehouse Ln, Shepherdstown, WV 25443

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 and a spacious primary suite with a large

Kara Burnett Samson Properties

104 Stonehouse Ln, Shepherdstown, WV 25443
/38
$469,990 Sold Jan 21, 2026

92 Open Gate Ln, Shepherdstown, WV 25443
- 5 Beds
- 3 Baths
- 2,511 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $187/SF
- 35 Days On Market
D.R. Horton Tollhouse Woods

92 Open Gate Ln, Shepherdstown, WV 25443

/29
Not Listed For Sale

231 Lyon Ridge Rd, Shepherdstown, WV 25443
- 4 Beds
- 2.5 Baths
- 2,969 Sq Ft
- Built 2024
231 Lyon Ridge Rd, Shepherdstown, WV 25443

Last Sold Summary
- $155/SF
- 11 Days On Market
Last Sold Price $459,990

Last Listing Agent Kathleen Cassidy DRH Realty Capital, LLC.

/50
$130,000
- Land
- 0.75 Acre
- $173,333 per Acre
LOT 9 Briar Mountain Dr, Shepherdstown, WV 25443

Lot 9, Briar Mountain Drive, North Hills at Cress Creek is one of the last remaining lots available in the sought after Shepherdstown's Premier 18 hole private golf course community. The cul-de-sac lot with access to water and sewer is waiting for your custom home to be built. This beautiful lot which borders a working farm preserved by a conservation easement offers peaceful privacy. Whether you

Dianne Maselli Coldwell Banker Premier

LOT 9 Briar Mountain Dr, Shepherdstown, WV 25443
/50
$425,000 Sold Dec 12, 2025

174 Byer Ln, Shepherdstown, WV 25443
- 3 Beds
- 2 Baths
- 2,080 Sq Ft
- Built 1977
Last Sold Summary
- $204/SF
- 35 Days On Market
Current Estimated Value $425,116

Last Listing Agent Chris Hoffmaster Berkshire Hathaway Homeservices Homesale Realty

174 Byer Ln, Shepherdstown, WV 25443

/15
Est $319,667 Not Listed For Sale

310 W German St, Shepherdstown, WV 25443
- 1 Bed
- 1 Bath
- 1,288 Sq Ft
- Built 1800
310 W German St, Shepherdstown, WV 25443

Last Sold Summary
- 16% Above List Price
- $214/SF
- 165 Days On Market
Last Sold Price $275,000

Last Listing Agent Wendy Williams Greentree Associates of Shepherdstown, Inc.

/22
$315,000
- 3 Beds
- 1.5 Baths
- 1,380 Sq Ft
136 Woodcock Ave, Shepherdstown, WV 25443

Welcome to 136 Woodcock Ave — a spacious 3-bedroom, 1.5-bath rancher set on nearly half an acre in the established Mecklenburg Heights community. Offering comfortable one-level living and a wide, gently wooded lot, this home blends everyday ease with the quiet charm of a well-loved neighborhood just minutes from historic Shepherdstown. Step inside to a bright living room that sets a warm,

Carolyn Young Samson Properties

136 Woodcock Ave, Shepherdstown, WV 25443
/59
$460,000 Sold Apr 30, 2025

451 Maddex Farm Dr, Shepherdstown, WV 25443
- 4 Beds
- 2.5 Baths
- 2,935 Sq Ft
- Built 2010
Last Sold Summary
- $157/SF
- 21 Days On Market
Current Estimated Value $460,029

Last Listing Agent Adam Shively Samson Properties

451 Maddex Farm Dr, Shepherdstown, WV 25443

/60
Est $422,547 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
- 5% Below List Price
- $152/SF
- 6 Days On Market
Last Sold Price $445,000

Last Listing Agent Morgan Boyer Hunt Country Sotheby's International Realty

/23
$449,900
- Land
- 7.85 Acres
- $57,312 per Acre
0 Ridge Rd Unit WVJF2020954, Shepherdstown, WV 25443

Don't miss out on this rare opportunity to own nearly 8 UNRESTRICTED acres in Shepherdstown. Sweeping sunset views make this a perfect location to lay down roots and build your forever home.Build with confidence as major groundwork is already complete. Perc-approved for a 4-bedroom house with well already in place. Experience true flexibility to build your dream home with NO HOA. Although the

James Smith Burch Real Estate Group, LLC

0 Ridge Rd Unit WVJF2020954, Shepherdstown, WV 25443
/10
$120,000 Sold Mar 25, 2025

0 Steamboat Run Rd Unit WVJF2016174, Shepherdstown, WV 25443
- Land
- 1.55 Acres
- $77,419 per Acre
Last Sold Summary
- 0 Days On Market
Last Listing Agent Terri Evans Keller Williams Realty

0 Steamboat Run Rd Unit WVJF2016174, Shepherdstown, WV 25443

/53
Est $407,337 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
- 2% Above List Price
- $175/SF
- 34 Days On Market
Last Sold Price $399,900

Last Listing Agent Adam Shively Samson Properties

/2
$825,000
- Land
- 3.7 Acres
- $222,973 per Acre
8285 Martinsburg Pike, Shepherdstown, WV 25443

PRIME LAND adjacent to Shepherd University, Domino's, and, across the street from WVU Medical PRIME LAND adjacent to Shepherd University, Domino's, and, across the street from WVU Medical Facility and ROC's convenience store! SENECA CROSSING NORTHSIDE apartment concept... 40 units have been approved for this site...five buildings of eight units each. Perfect site for much needed apartments. House

Jacqueline Lewis Greentree Associates of Shepherdstown, Inc.

8285 Martinsburg Pike, Shepherdstown, WV 25443
/34
$197,000 Sold Aug 26, 2025

111 Ray St, Shepherdstown, WV 25443
- 2 Beds
- 1 Bath
- 786 Sq Ft
- Built 1950
Last Sold Summary
- $251/SF
- 68 Days On Market
Current Estimated Value $198,709

Last Listing Agent Liz McDonald Dandridge Realty Group, LLC

111 Ray St, Shepherdstown, WV 25443

/68
Est $509,443 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
- 12% Above List Price
- $109/SF
- 41 Days On Market
Last Sold Price $455,000

Last Listing Agent Lisa Kingsbury Charis Realty Group

/33
$475,000
- 4 Beds
- 2.5 Baths
- 2,184 Sq Ft
280 Leisure Way, Shepherdstown, WV 25443

Perfectly positioned on over 2 acres just outside Shepherdstown, this 4-bedroom Colonial is located in a sought-after community with river access. The main level offers warm hardwood floors, a welcoming family room with fireplace, and a beautifully updated kitchen featuring new quartz countertops and an expansive pantry with cabinetry for exceptional storage. A light-filled sunroom provides the

Meredith Smith Samson Properties

280 Leisure Way, Shepherdstown, WV 25443
/34
$482,490 Sold Mar 24, 2025

261 Lyon Ridge Rd, Shepherdstown, WV 25443
- 4 Beds
- 2.5 Baths
- 2,969 Sq Ft
- Built 2024
Last Sold Summary
- $163/SF
- 209 Days On Market
Last Listing Agent Kathleen Cassidy D R Horton Realty of Virginia LLC

261 Lyon Ridge Rd, Shepherdstown, WV 25443

/19
Est $235,841 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
- 3% Above List Price
- $216/SF
- 42 Days On Market
Last Sold Price $228,000

Last Listing Agent Sarah Santacroce Coldwell Banker Premier

/53
$319,000 Under Contract
- 3 Beds
- 2 Baths
- 1,338 Sq Ft
224 Spring Warbler Way, Shepherdstown, WV 25443

***Due to strong interest and multiple offers received, the seller is requesting highest and best by 5:00 PM Monday. All offers will be reviewed promptly thereafter, thank you!***Welcome to this charming 3-bedroom, 2-bath home ideally located just minutes from downtown Shepherdstown. Situated on a prime, level 1-acre lot backing to mature trees, this property offers the perfect blend of

Kayla Skurski Century 21 Redwood Realty

224 Spring Warbler Way, Shepherdstown, WV 25443
/104
$923,000 Sold Mar 05, 2025

405 Spring Creek Ln, Shepherdstown, WV 25443
- 3 Beds
- 2.5 Baths
- 3,102 Sq Ft
- Built 1825
Last Sold Summary
- $298/SF
- 7 Days On Market
Current Estimated Value $934,553

Last Listing Agent Morgan Boyer Hunt Country Sotheby's International Realty

405 Spring Creek Ln, Shepherdstown, WV 25443

/50
Est $248,224 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% Above List Price
- $195/SF
- 10 Days On Market
Last Sold Price $225,000

Last Listing Agent Densil Nibert Nibert Realty & Auctions, LLC

/18
$562,000
- Land
- 5.3 Acres
- $106,038 per Acre
LOt 9 Shepherds Cove Swift River Way, Shepherdstown, WV 25443

LAST RIVER FRONT lot available at Shepherds Cove 5.4 Acre beautiful wooded lot sited on a bluff overlooking the Potomac River. BEAUTIFUL UNOBSTRUCTED VIEWS UP AND DOWN THE RIVER. Located in the shadow of historic Shepherdstown ,Shepherds Cove is a unique community for those selective home buyers who prefer woods and natural topography as their view , and golf carts as their preferred means to go

Carolyn Snyder Snyder Bailey & Associates

LOt 9 Shepherds Cove Swift River Way, Shepherdstown, WV 25443
/47
$215,000 Sold Oct 31, 2025

24 Cavaland Terrace, Shepherdstown, WV 25443
- 2 Beds
- 1.5 Baths
- 1,408 Sq Ft
- Built 1976
Last Sold Summary
- $153/SF
- 7 Days On Market
Current Estimated Value $217,183

Last Listing Agent Cheryl Yates ERA Liberty Realty

24 Cavaland Terrace, Shepherdstown, WV 25443

/43
Est $515,237 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
- 14% Above List Price
- $182/SF
- 43 Days On Market
Last Sold Price $450,000

Last Listing Agent Jordan Butts Burch Real Estate Group, LLC

/17
$209,000
- Land
- 4.36 Acres
- $47,936 per Acre
Lot #20 Shepherds Cove Swift River Way, Shepherdstown, WV 25443

Shepherds Cove Potomac River Waterfront Community, Shepherdstown WV Lot 20 is an exceptional opportunity READY TO BUILD, beautiful wooded lot with well installed, lot has been cleared for house construction, community septic. Peaceful, tranquil setting. Shepherd Cove is a small , resort-like community of 19 lots with only 4 remaining. These large private lots have marina privileges, and private

Carolyn Snyder Snyder Bailey & Associates

Lot #20 Shepherds Cove Swift River Way, Shepherdstown, WV 25443
/143
$1,050,000 Sold Mar 21, 2025

256 Swift River Way, Shepherdstown, WV 25443
- 4 Beds
- 4.5 Baths
- 4,000 Sq Ft
- Built 2023
Last Sold Summary
- $262/SF
- 120 Days On Market
Current Estimated Value $1,051,608

Last Listing Agent Jamie Lopez ERA Liberty Realty

256 Swift River Way, Shepherdstown, WV 25443

/78
Est $723,260 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
- 15% Below List Price
- $304/SF
- 182 Days On Market
Last Sold Price $850,000

Last Listing Agent Tara Lowe Samson Properties

/29
$179,500
- Land
- 0.66 Acre
- $271,970 per Acre
0 Reachcliff Dr Unit WVJF2019398, Shepherdstown, WV 25443

Tucked within one of the Eastern Panhandle’s most sought-after communities, Lot 107 on Reachcliff Drive presents a once-in-a-generation opportunity to build your custom home in Fernbank—known for its natural beauty, welcoming neighbors, and golf course setting. This lot provides 89' of frontage along the 5th fairway. Positioned at the highest elevation in the neighborhood, this wooded lot offers

Tracy Kable Real Broker, LLC

0 Reachcliff Dr Unit WVJF2019398, 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 $342,789

Last Listing Agent Kara Burnett Samson Properties

53 Stonehouse Ln, Shepherdstown, WV 25443

/74
Est $541,381 Not Listed For Sale

564 Steamboat Run Rd, Shepherdstown, WV 25443
- 4 Beds
- 3 Baths
- 4,108 Sq Ft
- Built 1974
564 Steamboat Run Rd, Shepherdstown, WV 25443

Last Sold Summary
- 13% Above List Price
- $117/SF
- 4 Days On Market
Last Sold Price $480,000

Last Listing Agent Tara Lowe Samson Properties

/37
$324,000 Under Contract
- 3 Beds
- 2.5 Baths
- 2,680 Sq Ft
286 Starkeys Landing, Shepherdstown, WV 25443

Welcome to 286 Starkeys Landing, a spacious 3-bedroom, 2.5-bath townhome quietly set within the established Starkeys Landing community of Shepherdstown, West Virginia. Offering just over 2,100 square feet of finished living space, this home blends warmth, comfort, and light in a way that feels immediately like home. The lower level opens through a bright two-story foyer where sunlight filters

Carolyn Young Samson Properties

286 Starkeys Landing, Shepherdstown, WV 25443

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West Virginia Jefferson County Shepherdstown

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