Shepherdstown, WV Homes

/48
$300,000

$25K PRICE DROP
- 3 Beds
- 4 Baths
- 1,750 Sq Ft
45 Ryan Ct, Shepherdstown, WV 25443

Welcome to 45 Ryan Court, where low-maintenance living meets the charm and character of historic Shepherdstown. Nestled in the desirable Maddex Farm community, this spacious three-level townhome offers approximately 1,900 square feet of comfortable living space with 3 bedrooms, 2 full baths, and 2 half baths.The inviting main level features a bright, open floor plan that seamlessly

Tara Lowe

Samson Properties

45 Ryan Ct, Shepherdstown, WV 25443
Explore Shepherdstown
/2
Starting at $840 Per Month
- 2 Beds
540 S Church St, Shepherdstown, WV 25443

Maple Green Apartments

540 S Church St, Shepherdstown, WV 25443
/30
$400,000

Sold Feb 10, 2026

8709 Shepherdstown Pike, Shepherdstown, WV 25443
- 2 Beds
- 2 Baths
- 1,530 Sq Ft
- Built 1920
Last Sold Summary
- 11% Below List Price
- $261/SF
- 47 Days On Market
Current Estimated Value $407,928

Last Listing Agent Nadine Kennedy Coldwell Banker Premier

8709 Shepherdstown Pike, Shepherdstown, WV 25443

/30
Not Listed For Sale

43 Open Gate Ln, Shepherdstown, WV 25443
- 4 Beds
- 3 Baths
- 2,401 Sq Ft
- Built 2025
43 Open Gate Ln, Shepherdstown, WV 25443

Last Sold Summary
- 0 Days On Market
Last Listing Agent Justin Wood D.R. Horton Realty of Virginia, LLC

/75
$795,000

Pending
- 4 Beds
- 3 Baths
- 4,500 Sq Ft
184 Heritage Dr, Shepherdstown, WV 25443

Welcome to 184 Heritage Drive, an impressive Shepherdstown residence where generous living spaces, quality craftsmanship, and exceptional amenities come together to create a home designed for comfortable living and effortless entertaining.From the moment you arrive, the beautiful front porch creates a warm and welcoming first impression—an inviting place to relax and enjoy the peaceful

Mercedes Prohaska

Coldwell Banker Premier

184 Heritage Dr, Shepherdstown, WV 25443
/33
$3,395 Per Month
- 4 Beds
- 3.5 Baths
- 5,075 Sq Ft
- House for Rent
29 Pathfinder Ct, Shepherdstown, WV 25443

Stunning, 4-Bedroom Luxury Home for Rent in Shepherdstown, WV!Spacious, upgraded, and available immediately! This 5,075-square-foot, four-bedroom, three-and-a-half-bath Colonial at 29 Pathfinder Court offers an impressive combination of comfort, style, and versatility. Situated on an attractive corner lot in Deerfield Village, the home features an open-concept layout, abundant natural

Ashley Crabill Coldwell Banker Premier

29 Pathfinder Ct, Shepherdstown, WV 25443
/54
$600,000

Sold Mar 23, 2026

150 Morgana Dr, Shepherdstown, WV 25443
- 4 Beds
- 4 Baths
- 3,060 Sq Ft
- Built 2002
Last Sold Summary
- $196/SF
- 243 Days On Market
Current Estimated Value $614,610

Last Listing Agent Matt Ridgeway RE/MAX Real Estate Group

150 Morgana Dr, Shepherdstown, WV 25443

/73
Est $623,545

Not Listed For Sale

72 Rolling Green Ct, Shepherdstown, WV 25443
- 6 Beds
- 4.5 Baths
- 4,416 Sq Ft
- Built 2007
72 Rolling Green Ct, Shepherdstown, WV 25443

Last Sold Summary
- 106 Days On Market
Last Listing Agent Adam Shively Samson Properties

/66
$670,000

$45K PRICE DROP
- 5 Beds
- 4.5 Baths
- 4,583 Sq Ft
48 Field Crest Ct, Shepherdstown, WV 25443

SELLER MOTIVATED! Don’t lose the opportunity to own this AMAZING BREATHTAKING VIEWS! on a property located in one of the nicest subdivisions in Jefferson County.Amazing views from all windows,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

Piedad Suarez

Spring Hill Real Estate, LLC.

48 Field Crest Ct, Shepherdstown, WV 25443
/10
$1,850 Per Month
- 4 Beds
- 2 Baths
- 1,431 Sq Ft
- House for Rent
334 W German St, Shepherdstown, WV 25443

Welcome to this charming rental located in Shepherdstown. The property offers 4 bedrooms and 2 full baths. There is a bedroom on the main level and three additional located upstairs. Walking distance to downtown Shepherdstown and Shepherd University. Off street parking. Pets allowed.

Brittany Lowe Burch Real Estate Group, LLC

334 W German St, Shepherdstown, WV 25443
/2
$110,000

Sold Jan 27, 2026

0 Comstock Dr Unit WVBE2042662, Shepherdstown, WV 25443
- Land
- 2.61 Acres
- $42,146 per Acre
Last Sold Summary
- 21% Below List Price
- 163 Days On Market
Last Listing Agent Eric Exline Roger Fairbourn Real Estate LLC

0 Comstock Dr Unit WVBE2042662, Shepherdstown, WV 25443

/53
Est $504,961

Not Listed For Sale

308 Maddex Dr, Shepherdstown, WV 25443
- 4 Beds
- 2.5 Baths
- 3,722 Sq Ft
- Built 2006
308 Maddex Dr, Shepherdstown, WV 25443

Last Sold Summary
- 27 Days On Market
Last Listing Agent Suzanne Frund Samson Properties

/21
$300,000
- Studio
- 1,920 Sq Ft
202 Old Martinsburg Rd, Shepherdstown, WV 25443

This 2-unit duplex just outside Shepherdstown offers incredible flexibility and income potential. Whether you're an investor seeking a strong rental opportunity or an owner-occupant looking to offset your mortgage, this property checks all the boxes. Live in one unit and rent the other, or maximize income by leasing both. Ideal for those with students attending Shepherd University, this property

Charlotte Sherman

Century 21 Modern Realty Results

202 Old Martinsburg Rd, Shepherdstown, WV 25443
/56
$548,250

Sold May 27, 2026

238 Comstock Dr, Shepherdstown, WV 25443
- 4 Beds
- 3 Baths
- 3,192 Sq Ft
- Built 2000
Last Sold Summary
- 10% Above List Price
- $172/SF
- 5 Days On Market
Current Estimated Value $540,770

Last Listing Agent Bill Dixon Dandridge Realty Group, LLC

238 Comstock Dr, Shepherdstown, WV 25443

/53
Est $639,842

Not Listed For Sale

130 N Tamarac Dr, Shepherdstown, WV 25443
- 3 Beds
- 2 Baths
- 1,654 Sq Ft
- Built 2023
130 N Tamarac Dr, Shepherdstown, WV 25443

Last Sold Summary
- 101 Days On Market
Last Listing Agent Travis Davis Burch Real Estate Group, LLC

/41
$324,000

$5K PRICE DROP Under Contract
- 3 Beds
- 4 Baths
- 2,220 Sq Ft
39 Swearingen Way, Shepherdstown, WV 25443

Welcome to this Convenient and Spacious Townhome with Brick Façade, Serene Wooded Views, 3 Bedrooms, 2 Full Bathrooms, and 2 Half Baths. Recent updates include Refinished Hardwood Floors, Newly Installed Redefined Pine Floors, recent New Deck Floor Boards, and an almost new HVAC System that was installed in 2024. Comcast cable and Xfinity are available. Enjoy the perfect blend of town and

Richard Kendall

Snyder Bailey & Associates

39 Swearingen Way, Shepherdstown, WV 25443
/41
$459,000

Sold Jun 24, 2026

205 W High St, Shepherdstown, WV 25443
- 3 Beds
- 1 Bath
- 1,386 Sq Ft
- Built 1790
Last Sold Summary
- 1% Below List Price
- $331/SF
- 4 Days On Market
Current Estimated Value $441,241

Last Listing Agent Errika Best Greentree Associates of Shepherdstown, Inc.

205 W High St, Shepherdstown, WV 25443

/76
Est $820,000

Not Listed For Sale

100 W New St, Shepherdstown, WV 25443
- 3 Beds
- 2.5 Baths
- 3,957 Sq Ft
- Built 1789
100 W New St, Shepherdstown, WV 25443

Last Sold Summary
- 10 Days On Market
Last Listing Agent Derek Eisenberg Continental Real Estate Group

/65
$589,000

$8K PRICE DROP
- 4 Beds
- 4 Baths
- 4,530 Sq Ft
262 Canal Way, Shepherdstown, WV 25443

Welcome to 262 Canal Way, Shepherdstown, WV, where thoughtful upgrades and an exceptional location come together in one beautiful home. Nestled in one of Shepherdstown's most desirable neighborhoods, this spacious residence offers the perfect blend of elegance, comfort, and functionality. Step inside to find beautiful hardwood floors flowing throughout the main living areas, creating a warm and

Tara Lowe

Samson Properties

262 Canal Way, Shepherdstown, WV 25443
/77
$570,000

Sold May 08, 2026

131 Butcher Ct, Shepherdstown, WV 25443
- 5 Beds
- 3.5 Baths
- 2,935 Sq Ft
- Built 2005
Last Sold Summary
- 4% Above List Price
- $194/SF
- 1 Day On Market
Current Estimated Value $560,617

Last Listing Agent Molly Marsh-Riley Marsh Realty

131 Butcher Ct, Shepherdstown, WV 25443

/57
Est $668,420

Not Listed For Sale

224 Shveda Way, Shepherdstown, WV 25443
- 4 Beds
- 4 Baths
- 2,860 Sq Ft
- Built 2018
224 Shveda Way, Shepherdstown, WV 25443

Last Sold Summary
- 52 Days On Market
Last Listing Agent Robert Krop Keller Williams Realty Centre

/56
$515,000

$10K PRICE DROP Under Contract
- 4 Beds
- 4 Baths
- 3,902 Sq Ft
65 Maddex Farm Dr, Shepherdstown, WV 25443

As soon as you enter this beautiful home you realize this is a well maintained one! Nice open stairway and two-story foyer to the second floor. Sparkling wood floors and laminate floors as well. First floor offers living room as well as a family room off the kitchen. Formal dining but breakfast room also and, counter seating in a beautifully laid out kitchen. Granite counters, gas stove, built in

Jacqueline Lewis Greentree Associates of Shepherdstown, Inc.

65 Maddex Farm Dr, Shepherdstown, WV 25443
/28
$389,990

Sold Oct 29, 2025

55 Open Gate Ln, Shepherdstown, WV 25443
- 3 Beds
- 2.5 Baths
- 2,200 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $177/SF
- 28 Days On Market
55 Open Gate Ln, Shepherdstown, WV 25443

/73
Est $358,607

Not Listed For Sale

796 Dam 4 Rd, Shepherdstown, WV 25443
- 3 Beds
- 2 Baths
- 2,200 Sq Ft
- Built 1900
796 Dam 4 Rd, Shepherdstown, WV 25443

Last Sold Summary
- 82 Days On Market
Last Listing Agent Sarah Combs Hoffman Realty

/50
$140,000

$10K PRICE INCREASE Under Contract
- Land
- 32,670 Sq Ft
- $186,667 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
/8
$370,000

Sold Jul 10, 2026

0 Lot 3a Ridge Rd, Shepherdstown, WV 25443
- Land
- 7.85 Acres
- $47,134 per Acre
Last Sold Summary
- 18% Below List Price
- 169 Days On Market
Last Listing Agent James Smith Burch Real Estate Group, LLC

0 Lot 3a Ridge Rd, Shepherdstown, WV 25443

/69
Est $569,080

Not Listed For Sale

97 Heritage Dr, Shepherdstown, WV 25443
- 4 Beds
- 3 Baths
- 2,239 Sq Ft
- Built 2018
97 Heritage Dr, Shepherdstown, WV 25443

Last Sold Summary
- 34 Days On Market
Last Listing Agent Gregory Graham ERA Liberty Realty

/2
$650,000
- Land
- 3.7 Acres
- $175,676 per Acre
8285 Martinsburg Pike, Shepherdstown, WV 25443

This TPRIME LAND adjacent to Shepherd University, Domino's, and, across the street from WVU Medical facility and ROC's convenience store has A MAJOR PRICE REDUCTION!!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 on the property is unlivable and there is approval to

Jacqueline Lewis Greentree Associates of Shepherdstown, Inc.

8285 Martinsburg Pike, Shepherdstown, WV 25443
/4
$160,000

Sold Nov 24, 2025

39 Nightingale Ln, Shepherdstown, WV 25443
- 3 Beds
- 1 Bath
- 1,656 Sq Ft
- Built 1975
Last Sold Summary
- $97/SF
- 65 Days On Market
Current Estimated Value $296,080

Last Listing Agent Jennifer Largent Compass West Realty, LLC

39 Nightingale Ln, Shepherdstown, WV 25443

/34
Est $367,789

Not Listed For Sale

262 Old Martinsburg Rd, Shepherdstown, WV 25443
- 3 Beds
- 2 Baths
- 1,796 Sq Ft
- Built 1968
262 Old Martinsburg Rd, Shepherdstown, WV 25443

Last Sold Summary
- 6 Days On Market
Last Listing Agent Sarah Santacroce Coldwell Banker Premier

/41
$369,900
- 3 Beds
- 2.5 Baths
- 1,536 Sq Ft
35 Oatfield Ct, Shepherdstown, WV 25443

Discover the charm of this beautifully renovated Cape Cod home nestled in the desirable Maddex Farm community. With a major renovation completed in 2026, this residence boasts an excellent condition and upgrades throughout. The upgraded countertops and luxury vinyl plank flooring add a touch of elegance, while the breakfast area invites casual dining. This home features three comfortable

Adam Shively Samson Properties

35 Oatfield Ct, Shepherdstown, WV 25443
/33
$475,000

Sold May 08, 2026

280 Leisure Way, Shepherdstown, WV 25443
- 4 Beds
- 2.5 Baths
- 2,184 Sq Ft
- Built 2000
Last Sold Summary
- $217/SF
- 53 Days On Market
Current Estimated Value $476,657

Last Listing Agent Meredith Smith Samson Properties

280 Leisure Way, Shepherdstown, WV 25443

/39
Est $674,872

Not Listed For Sale

101 N Princess St, Shepherdstown, WV 25443
- 3 Beds
- 2 Baths
- 2,350 Sq Ft
- Built 1793
101 N Princess St, Shepherdstown, WV 25443

Last Sold Summary
- 4 Days On Market
Last Listing Agent Dan Anderson Greentree Associates of Shepherdstown, Inc.

/36
$344,999

$13K PRICE DROP Under Contract
- 4 Beds
- 2.5 Baths
- 2,880 Sq Ft
420 Starkeys Landing, Shepherdstown, WV 25443

New Price Improvement! The premier, three-level, corner lot townhome located in the Colonial Hills neighborhood of 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

Andrew Lowe Path Realty

420 Starkeys Landing, Shepherdstown, WV 25443
/56
$350,000

Sold Dec 05, 2025

21 Rock Spring Ln, Shepherdstown, WV 25443
- 3 Beds
- 3 Baths
- 3,480 Sq Ft
- Built 1986
Last Sold Summary
- $101/SF
- 20 Days On Market
Current Estimated Value $378,129

Last Listing Agent Debbie Hugo Samson Properties

21 Rock Spring Ln, Shepherdstown, WV 25443

/44
Est $660,493

Not Listed For Sale

12 Briar Mountain Dr, Shepherdstown, WV 25443
- 3 Beds
- 3.5 Baths
- 2,938 Sq Ft
- Built 2013
12 Briar Mountain Dr, Shepherdstown, WV 25443

Last Sold Summary
- 87 Days On Market
Last Listing Agent Adam Miller Coldwell Banker Premier

/10
$159,000

Under Contract
- Land
- 2 Acres
- $79,500 per Acre
Lot 1 Sandpiper Ln, Shepherdstown, WV 25443

Discover the perfect setting for your future home on this beautiful 2-acre wooded lot in an established Shepherdstown-area community. Surrounded by mature trees and adjacent to community open space, the property offers a wonderful sense of privacy and a peaceful, natural setting. Enjoy the rare combination of generous acreage with the convenience of public water and sewer. Largely untouched and

Louise McDonald Dandridge Realty Group, LLC

Lot 1 Sandpiper Ln, Shepherdstown, WV 25443
/84
$300,000

Sold Oct 30, 2025

838 Billmyer Mill Rd, Shepherdstown, WV 25443
- 2 Beds
- 1 Bath
- 1,658 Sq Ft
- Built 1968
Last Sold Summary
- $181/SF
- 102 Days On Market
Current Estimated Value $297,479

Last Listing Agent Densil Nibert Nibert Realty & Auctions, LLC

838 Billmyer Mill Rd, Shepherdstown, WV 25443

/18
Est $377,066

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
- 4 Days On Market
Last Listing Agent Wendy Williams Greentree Associates of Shepherdstown, Inc.

/45
$400,000
- 3 Beds
- 3 Baths
- 1,740 Sq Ft
207 Sandpiper Ln, Shepherdstown, WV 25443

Welcome to 207 Sandpiper Lane, a beautifully maintained, like new, 3-bedroom, 3-full-bath home situated on nearly one acre in desirable Shepherdstown, West Virginia. Built in 2018, this inviting property offers a thoughtful layout with generous living space and a fully finished walkout lower level. The main level offers an open floor plan, hardwood floors in the main living areas, a spacious

Paul Warthen Real Estate Teams, LLC

207 Sandpiper Ln, Shepherdstown, WV 25443

Showing Results 1 - 40, Page 1 of 18

West Virginia Jefferson County

Home Prices in Shepherdstown, WV

The median home sale price in Shepherdstown, WV is $460,000, down 5% year-over-year. Homes in Shepherdstown sell in 52 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price $460,000	Median Single Family Sale Price $467,495
Median Townhouse Sale Price $307,500	Median 2 Bedroom Sale Price $300,000
Median 1 Bedroom Sale Price $200,000	Average Price Per Sq Ft $185
Number of Homes for Sale 19	Last 12 months Home Sales 137
Months of Supply 1.70	Median List Price $472,240
Median Change From 1st List Price 0%	Median Home Sale Price YoY Change -5%

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Shepherdstown, WV Homes

Real Estate & Homes

Home Prices in Shepherdstown, WV

Home Price Trends