Real Estate Investment Properties for Sale in Shepherdstown, WV
Looking for investment property in Shepherdstown, WV with high ROI ?
Explore a variety of short-term homes & houses in Shepherdstown, WV. Invest wisely with VRBO & Shepherdstown, WV Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Shepherdstown, WV
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
50 Lamar LnSHEPHERDSTOWN, WVNEW LOWER PRICE! Seller is offering up to $10,000 towards Buyer's closing costs! This beau... |
4 beds | 3 baths | 2,200 sq.ft. |
$560,000 |
Airbnb cash on cash: N/A
|
20 Drennen CtSHEPHERDSTOWN, WVOverlooking Cress Creek Golf Club in Shepherdstown, this villa-style duplex offers a setti... |
3 beds | 3 baths | 2,295 sq.ft. |
$525,000 |
Airbnb cash on cash: 1.51%
|
49 Appomattox LnSHEPHERDSTOWN, WVStunning 5-bedroom, 3.5-bath Colonial tucked away on a private half-acre lot backing to ma... |
5 beds | 3 baths | 3,950 sq.ft. |
$579,900 |
Airbnb cash on cash: N/A
|
202 Old Martinsburg RdSHEPHERDSTOWN, WVIncome generating property! Fully rented with stable income. Great investment property o... |
5 beds | 2 baths | 1,920 sq.ft. |
$300,000 |
Airbnb cash on cash: N/A
|
65 Maddex Farm DrSHEPHERDSTOWN, WVAs soon as you enter this beautiful home you realize this is a well maintained one! Nice o... |
4 beds | 2 baths | 3,902 sq.ft. |
$515,000 |
Airbnb cash on cash: N/A
|
22 Fairmont AveSHEPHERDSTOWN, WVRare offering on Fairmont on one of Shepherdstownâs most desirable walkable streets. Her... |
4 beds | 3 baths | 2,628 sq.ft. |
$850,000 |
Airbnb cash on cash: N/A
|
45 Ryan CtSHEPHERDSTOWN, WVWelcome to 45 Ryan Court, where low-maintenance living meets the charm and character of hi... |
3 beds | 2 baths | 1,750 sq.ft. |
$310,000 |
Airbnb cash on cash: 3.89%
|
185 Shepherd LnSHEPHERDSTOWN, WVSet on 4.07 acres just minutes from downtown Shepherdstown, this spacious home offers room... |
4 beds | 2 baths | 2,176 sq.ft. |
$635,000 |
Airbnb cash on cash: N/A
|
105 Rabbits Rest LnSHEPHERDSTOWN, WV105 Rabbits Rest Ln, SHEPHERDSTOWN, WV 25443 | Single Family Residential |
3 beds | 2 baths | 2,500 sq.ft. |
$949,000 |
Airbnb cash on cash: 0.17%
|
Lot 2 Martinsburg PikeSHEPHERDSTOWN, WVLot 2 Martinsburg Pike, SHEPHERDSTOWN, WV 25443 | Other |
N/A beds | N/A baths | N/A |
$500,000 |
Airbnb cash on cash: -0.05%
|
Lot 3 Martinsburg PikeSHEPHERDSTOWN, WVLot 3 Martinsburg Pike, SHEPHERDSTOWN, WV 25443 | Other |
N/A beds | N/A baths | N/A |
$500,000 |
Airbnb cash on cash: -0.05%
|
8285 Martinsburg PikeSHEPHERDSTOWN, WV8285 Martinsburg Pike, SHEPHERDSTOWN, WV 25443 | Other |
N/A beds | N/A baths | N/A |
$650,000 |
Airbnb cash on cash: -0.39%
|
19 Cardinal DrSHEPHERDSTOWN, WV
|
3 beds | 1 baths | 1,352 sq.ft. |
$309,000 |
Airbnb cash on cash: 3.93%
|
157 LYON RIDGESHEPHERDSTOWN, WVWhy wait for new construction when you can move right into a nearly new home with upgrades... |
4 beds | 3 baths | 1,906 sq.ft. |
$410,000 |
Airbnb cash on cash: N/A
|
Lot #20 Shepherds Cove Swift River WaySHEPHERDSTOWN, WVLot #20 Shepherds Cove Swift River Way, SHEPHERDSTOWN, WV 25443 | Other |
N/A beds | N/A baths | N/A |
$209,000 |
Airbnb cash on cash: 0.89%
|
48 Field Crest CtSHEPHERDSTOWN, WVSELLER MOTIVATED! Don't lose the opportunity to own this AMAZING BREATHTAKING VIEWS! on a ... |
5 beds | 4 baths | 4,583 sq.ft. |
$687,000 |
Airbnb cash on cash: N/A
|
61 Hartzell DrSHEPHERDSTOWN, WVThis delightful semi detached home offers a perfect blend of comfort and style with an ass... |
3 beds | 2 baths | 2,239 sq.ft. |
$535,000 |
Airbnb cash on cash: 1.34%
|
Swift River Way, Lot 6SHEPHERDSTOWN, WVSwift River Way, Lot 6, SHEPHERDSTOWN, WV 25443 | Other |
N/A beds | N/A baths | N/A |
$215,000 |
Airbnb cash on cash: 0.82%
|
Lot #14 (North Hills) Briar Mountain DrSHEPHERDSTOWN, WVLot #14 (North Hills) Briar Mountain Dr, SHEPHERDSTOWN, WV 25443 | Other |
N/A beds | N/A baths | N/A |
$179,900 |
Airbnb cash on cash: 2.28%
|
122 Hensel DrSHEPHERDSTOWN, WVMain level living never looked so easy in this newly renovated and move-in ready contempor... |
3 beds | 2 baths | 1,901 sq.ft. |
$390,000 |
Airbnb cash on cash: 2.7%
|
561 Billmyer Mill RdSHEPHERDSTOWN, WVCharming Country Retreat nestled on a peaceful 1.63-acre private parcel along a quiet coun... |
3 beds | 2 baths | 2,611 sq.ft. |
$439,000 |
Airbnb cash on cash: 2.31%
|
7341 Martinsburg PikeSHEPHERDSTOWN, WV3 Bedroom 1 Bath home conveniently located in Shepherdstown. Convenient to shops, restaura... |
3 beds | 1 baths | 1,224 sq.ft. |
$171,950 |
Airbnb cash on cash: 7.87%
|
637 Persimmon LnSHEPHERDSTOWN, WV637 Persimmon Ln, SHEPHERDSTOWN, WV 25443 | Single Family Residential |
4 beds | 3 baths | 2,866 sq.ft. |
$575,000 |
Airbnb cash on cash: N/A
|
17 Old Prospect AveSHEPHERDSTOWN, WV17 Old Prospect Ave, SHEPHERDSTOWN, WV 25443 | Single Family Residential |
3 beds | 1 baths | 1,560 sq.ft. |
$425,000 |
Airbnb cash on cash: 2.34%
|
420 Starkeys LndgSHEPHERDSTOWN, WV420 Starkeys Lndg, SHEPHERDSTOWN, WV 25443 | Townhouse |
4 beds | 2 baths | 2,880 sq.ft. |
$344,999 |
Airbnb cash on cash: N/A
|
39 Swearingen WaySHEPHERDSTOWN, WVWelcome to this Sun-Drenched and Spacious Townhome with Brick Facade, Serene Wooded Views,... |
3 beds | 2 baths | 2,220 sq.ft. |
$324,000 |
Airbnb cash on cash: 3.36%
|
262 Canal WaySHEPHERDSTOWN, WVWelcome to 262 Canal Way, Shepherdstown, WV, where thoughtful upgrades and an exceptional ... |
4 beds | 2 baths | 4,530 sq.ft. |
$589,000 |
Airbnb cash on cash: N/A
|
Otter Run Pl Lot 3SHEPHERDSTOWN, WVOtter Run Pl Lot 3, SHEPHERDSTOWN, WV 25443 | Other |
N/A beds | N/A baths | N/A |
$722,400 |
Airbnb cash on cash: -0.51%
|
92 Fidlers WaySHEPHERDSTOWN, WV92 Fidlers Way, SHEPHERDSTOWN, WV 25443 | Single Family Residential |
3 beds | 3 baths | 3,500 sq.ft. |
$749,000 |
Airbnb cash on cash: 0.66%
|
7174 Martinsburg PikeSHEPHERDSTOWN, WV7174 Martinsburg Pike, SHEPHERDSTOWN, WV 25443 | Other |
N/A beds | N/A baths | N/A |
$800,000 |
Airbnb cash on cash: -0.62%
|
35 Oatfield CtSHEPHERDSTOWN, WV35 Oatfield Ct, SHEPHERDSTOWN, WV 25443 | Single Family Residential |
3 beds | 2 baths | 1,536 sq.ft. |
$374,900 |
Airbnb cash on cash: 2.73%
|
104 E German StSHEPHERDSTOWN, WV104 E German St, SHEPHERDSTOWN, WV 25443 | Multi Family |
5 beds | N/A baths | 4,416 sq.ft. |
$579,900 |
Airbnb cash on cash: 1.3%
|
7628 Martinsburg PikeSHEPHERDSTOWN, WV7628 Martinsburg Pike, SHEPHERDSTOWN, WV 25443 | Single Family Residential |
3 beds | 1 baths | 1,000 sq.ft. |
$285,000 |
Airbnb cash on cash: 4.23%
|
207 Sandpiper LnSHEPHERDSTOWN, WV207 Sandpiper Ln, SHEPHERDSTOWN, WV 25443 | Single Family Residential |
3 beds | 3 baths | 1,740 sq.ft. |
$400,000 |
Airbnb cash on cash: 2.51%
|
91 Marsh Hawk WaySHEPHERDSTOWN, WV91 Marsh Hawk Way, SHEPHERDSTOWN, WV 25443 | Single Family Residential |
4 beds | 2 baths | 2,684 sq.ft. |
$665,000 |
Airbnb cash on cash: N/A
|
7 Old Prospect AveSHEPHERDSTOWN, WV7 Old Prospect Ave, SHEPHERDSTOWN, WV 25443 | Single Family Residential |
4 beds | 2 baths | 2,146 sq.ft. |
$530,000 |
Airbnb cash on cash: N/A
|
277 Shveda WaySHEPHERDSTOWN, WV277 Shveda Way, SHEPHERDSTOWN, WV 25443 | Single Family Residential |
4 beds | 3 baths | 2,144 sq.ft. |
$649,900 |
Airbnb cash on cash: N/A
|
Real Estate investment in Shepherdstown, WV
There are 41 properties for sale in the city of Shepherdstown . The median list price in Shepherdstown is $639,617 and the average price per square foot is $253. In August 2026, the average monthly cash on cash return in Shepherdstown is 3.00%. The average monthly rental income in Shepherdstown is $1,870.