Shepherdstown, WV Homes

/66
$687,000

$28K PRICE DROP
- 5 Beds
- 4.5 Baths
- 4,583 Sq Ft
48 Field Crest Ct, Shepherdstown, WV 25443

NEWLY PRICE ADJUSTED- 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.

Piedad Suarez

Spring Hill Real Estate, LLC.

48 Field Crest Ct, Shepherdstown, WV 25443
Explore Shepherdstown
/24
$2,600 Per Month
- 4 Beds
- 2 Baths
- 1,938 Sq Ft
- House for Rent
164 Ashley Dr, Shepherdstown, WV 25443

146 Ashley Drive is available for rent with lease beginning September 1, 2026! Nestled in a quiet neighborhood, with large shady trees, this home is located on the edge of Shepherdstown. Boasting 4 bedrooms and 2 baths, this single family home sits on a FLAT almost a half acre with an attached garage and fully fenced rear yard. The home has almost 2000 sq feet of finished area with a washer and

Amie Cardello Path Realty

164 Ashley Dr, 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 $405,433

Last Listing Agent Nadine Kennedy Coldwell Banker Premier

8709 Shepherdstown Pike, Shepherdstown, WV 25443

/33
Not Listed For Sale

117 Open Gate Ln, Shepherdstown, WV 25443
- 4 Beds
- 2 Baths
- 1,698 Sq Ft
- Built 2025
117 Open Gate Ln, Shepherdstown, WV 25443

Last Sold Summary
- 0 Days On Market

/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
/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
/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 $611,534

Last Listing Agent Matt Ridgeway RE/MAX Real Estate Group

150 Morgana Dr, Shepherdstown, WV 25443

/83
Est $1,322,974

Not Listed For Sale

126 E German St, Shepherdstown, WV 25443
- 4 Beds
- 5 Baths
- 7,800 Sq Ft
- Built 1908
126 E German St, Shepherdstown, WV 25443

Last Sold Summary
- 11 Days On Market

/41
$329,000
- 3 Beds
- 4 Baths
- 2,220 Sq Ft
39 Swearingen Way, Shepherdstown, WV 25443

Welcome to this Sun-Drenched 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
/31
$3,395 Per Month
- 4 Beds
- 3.5 Baths
- 5,075 Sq Ft
- House for Rent
29 Pathfinder Ct, Shepherdstown, WV 25443

Welcome to this exceptional rental home situated on a desirablecorner lot, offering luxury, comfort, and space throughout. Thisbeautifully maintained property features numerous upgrades, afinished basement, and an open-concept floor plan designed forboth everyday living and entertaining. The gourmet-style layoutflows seamlessly into expansive living and dining areas,

Ashley Crabill Coldwell Banker Premier

29 Pathfinder Ct, 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

/70
Est $506,427

Not Listed For Sale

44 Folks Point, Shepherdstown, WV 25443
- 4 Beds
- 3.5 Baths
- 2,772 Sq Ft
- Built 2007
44 Folks Point, Shepherdstown, WV 25443

Last Sold Summary
- 13 Days On Market

/65
$597,000
- 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
/18
$1,695 Per Month
- 2 Beds
- 1 Bath
- 600 Sq Ft
- Condo for Rent
107 E Back Aly, Shepherdstown, WV 25443

Downtown Shepherdstown across from Shepherd University - 2 bedroom, 1 bath apartment on 2nd floor - rear of building. Updated including granite countertops, Stainless Steel appliances and a washer/dryer in the unit. 1 reserved parking space on site. Pets allowed on a case by case basis. $500 pet deposit. Available immediately. Owner is a licensed real estate agent.

Brian Masemer RE/MAX Real Estate Group

107 E Back Aly, 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 $503,423

Last Listing Agent Bill Dixon Dandridge Realty Group, LLC

238 Comstock Dr, Shepherdstown, WV 25443

/26
Est $612,073

Not Listed For Sale

75 Juniper Cir, Shepherdstown, WV 25443
- 4 Beds
- 3.5 Baths
- 2,589 Sq Ft
- Built 2001
75 Juniper Cir, Shepherdstown, WV 25443

Last Sold Summary
- 74 Days On Market

/98
$1,100,000

Open Sat 11AM - 2PM Pending
- 5 Beds
- 4.5 Baths
- 4,623 Sq Ft
4992 Scrabble Rd, Shepherdstown, WV 25443

Nestled on a sprawling 9.72-acre lot, this exquisite Cape Cod residence offers a harmonious blend of luxury and comfort, perfect for those seeking an exclusive lifestyle. The gourmet kitchen is a culinary enthusiast's dream, featuring upgraded countertops, a spacious island, and high-end appliances, including a double wall oven and a cooktop. The inviting breakfast area and traditional dining

Robert Bir

Samson Properties

4992 Scrabble Rd, Shepherdstown, WV 25443
/37
$1,900 Per Month
- 3 Beds
- 2.5 Baths
- 1,424 Sq Ft
- Townhouse for Rent
27 Ryan Ct, Shepherdstown, WV 25443

Lovely townhome for rent in the heart of Shepherdstown! Freshly painted and featuring a new deck, this place is move-in ready. Located in the highly sought after Maddex Farm subdivision, you'll be within walking distance to local grocery and convenience stores, and just down the road from the shops and restaurants in the historic downtown area. Enjoy both comfort and convenience with this one!

Gavin Washington Weichert Realtors - Blue Ribbon

27 Ryan Ct, 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 $420,966

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

205 W High St, Shepherdstown, WV 25443

/119
Est $931,082

Not Listed For Sale

115 Windward Ln, Shepherdstown, WV 25443
- 5 Beds
- 5 Baths
- 5,778 Sq Ft
- Built 1974
115 Windward Ln, Shepherdstown, WV 25443

Last Sold Summary
- 74 Days On Market

/48
$325,000
- 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 connects the

Tara Lowe

Samson Properties

45 Ryan Ct, Shepherdstown, WV 25443
/30
$508,490

Sold Aug 11, 2025

43 Open Gate Ln, Shepherdstown, WV 25443
- 4 Beds
- 3 Baths
- 2,401 Sq Ft
- Built 2025
Last Sold Summary
- $212/SF
- 0 Days On Market
Last Listing Agent Justin Wood D.R. Horton Realty of Virginia, LLC

43 Open Gate Ln, Shepherdstown, WV 25443

/41
Est $364,822

Not Listed For Sale

38 Wheat Ct, Shepherdstown, WV 25443
- 3 Beds
- 2.5 Baths
- 2,076 Sq Ft
- Built 1996
38 Wheat Ct, Shepherdstown, WV 25443

Last Sold Summary
- 24 Days On Market

/56
$515,000

Open Sun 1PM - 3PM $10K PRICE DROP
- 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
/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 $569,711

Last Listing Agent Molly Marsh-Riley Marsh Realty

131 Butcher Ct, Shepherdstown, WV 25443

/101
Est $968,719

Not Listed For Sale

1058 Marsh Hawk Way, Shepherdstown, WV 25443
- 4 Beds
- 4 Baths
- 4,411 Sq Ft
- Built 2012
1058 Marsh Hawk Way, Shepherdstown, WV 25443

Last Sold Summary
- 18 Days On Market

/50
$140,000

$10K PRICE INCREASE
- 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
/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

/40
Est $456,811

Not Listed For Sale

424 Maddex Farm Dr, Shepherdstown, WV 25443
- 4 Beds
- 4 Baths
- 3,054 Sq Ft
- Built 2010
424 Maddex Farm Dr, Shepherdstown, WV 25443

Last Sold Summary
- 36 Days On Market

/8
$392,000

$58K PRICE DROP Under Contract
- Land
- 7.85 Acres
- $49,936 per Acre
0 Lot 3a Ridge Rd, 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 Lot 3a Ridge Rd, Shepherdstown, WV 25443
/73
$590,000

Sold Aug 05, 2025

72 Rolling Green Ct, Shepherdstown, WV 25443
- 6 Beds
- 4.5 Baths
- 4,416 Sq Ft
- Built 2007
Last Sold Summary
- $134/SF
- 106 Days On Market
Current Estimated Value $621,134

Last Listing Agent Adam Shively Samson Properties

72 Rolling Green Ct, Shepherdstown, WV 25443

/57
Est $660,437

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

/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
/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 $473,574

Last Listing Agent Meredith Smith Samson Properties

280 Leisure Way, Shepherdstown, WV 25443

/73
Est $348,920

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

/36
$348,000

$10K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,880 Sq Ft
420 Starkeys Landing, Shepherdstown, WV 25443

Price Improvement! Premier, three-level, corner lot townhome located 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,

Andrew Lowe Path Realty

420 Starkeys Landing, Shepherdstown, WV 25443
/68
$600,000

Sold Jul 11, 2025

60 Reachcliff Dr, Shepherdstown, WV 25443
- 3 Beds
- 3 Baths
- 2,861 Sq Ft
- Built 2006
Last Sold Summary
- $210/SF
- 9 Days On Market
Current Estimated Value $617,948

Last Listing Agent Tara Lowe Samson Properties

60 Reachcliff Dr, Shepherdstown, WV 25443

/69
Est $543,835

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

/102
$850,000

$30K PRICE DROP
- 4 Beds
- 3 Baths
- 2,628 Sq Ft
22 Fairmont Ave, Shepherdstown, WV 25443

Just two blocks from the vibrant Shepherdstown Historic District and set along the quiet tree-lined street of Fairmont Avenue, this charming brick colonial offers a rare and compelling balance: immediate access to the character, walkability, and charm of historic Shepherdstown—while enjoying the flexibility and ease of living just outside the district’s formal guidelines. Beyond the main

Morgan Boyer Hunt Country Sotheby's International Realty

22 Fairmont Ave, 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 $375,305

Last Listing Agent Debbie Hugo Samson Properties

21 Rock Spring Ln, Shepherdstown, WV 25443

Showing Results 1 - 40, Page 1 of 18

West Virginia Jefferson County Shepherdstown

Home Prices in Shepherdstown, WV

The median home sale price in Shepherdstown, WV is $465,000, down 3% year-over-year. Homes in Shepherdstown sell in 55 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price $465,000	Median Single Family Sale Price $469,990
Median Townhouse Sale Price $338,500	Median 2 Bedroom Sale Price $293,750
Median 1 Bedroom Sale Price $200,000	Average Price Per Sq Ft $185
Number of Homes for Sale 19	Last 12 months Home Sales 144
Months of Supply 1.60	Median List Price $475,000
Median Change From 1st List Price 0%	Median Home Sale Price YoY Change -3%

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Shepherdstown, WV Homes

Real Estate & Homes

Home Prices in Shepherdstown, WV

Home Price Trends