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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
32 SCOTT Drive SHEPHERDSTOWN, WV Shepherdstown on a Half Acre and NO HOA! Close to downtown Shepherdstown and Shepherd Univ...	3 beds \| 3 baths \| 1,920 sq.ft.	$289,900	Airbnb cash on cash: 1.14% Traditional cash on cash: 5.64% Airbnb Rental Income: $1221 Traditional Rental Income: $2057 Airbnb ROI: 1.14% Traditional ROI: 5.64%
4781 Scrabble Rd SHEPHERDSTOWN, WV *PRICED BELOW CURRENT APPRAISAL* The George Washington Hollida House \| 4781 Scrabble R...	5 beds \| 2 baths \| 2,721 sq.ft.	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.07% Airbnb Rental Income: $null Traditional Rental Income: $2647 Airbnb ROI: N/A Traditional ROI: 2.07%
44 N TAMARAC Drive SHEPHERDSTOWN, WV Terrific floor plan for the buyers that need a bedroom on the first floor! Lots of nice la...	3 beds \| 3 baths \| 2,975 sq.ft.	$625,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 2.51% Airbnb Rental Income: $1221 Traditional Rental Income: $2482 Airbnb ROI: -0.33% Traditional ROI: 2.51%
115 SWEARINGEN Way SHEPHERDSTOWN, WV Interior town home, 3BR, 2 1/2 bath, with over 2,220 finished square feet in the highly de...	4 beds \| 3 baths \| 2,220 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.44% Airbnb Rental Income: $null Traditional Rental Income: $2411 Airbnb ROI: N/A Traditional ROI: 6.44%
12 MISTLETOE Lane SHEPHERDSTOWN, WV April 2026 delivery!! Home with 2 + / - acres situated in the new community of Hallmark Gl...	4 beds \| 6 baths \| 4,066 sq.ft.	$999,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.86% Airbnb Rental Income: $null Traditional Rental Income: $5207 Airbnb ROI: N/A Traditional ROI: 3.86%
5 JINGLE BELLS Court SHEPHERDSTOWN, WV May / June 2026 delivery!!! Home with 2 + / - acres situated in the new community of Hallm...	4 beds \| 4 baths \| 2,709 sq.ft.	$799,999	Airbnb cash on cash: N/A Traditional cash on cash: 1.06% Airbnb Rental Income: $null Traditional Rental Income: $2117 Airbnb ROI: N/A Traditional ROI: 1.06%
150 Morgana Dr SHEPHERDSTOWN, WV 150 Morgana Dr, SHEPHERDSTOWN, WV 25443 \| Single Family Residential	4 beds \| 4 baths \| 3,060 sq.ft.	$649,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.83% Airbnb Rental Income: $null Traditional Rental Income: $2200 Airbnb ROI: N/A Traditional ROI: 1.83%
19 MISTLETOE Lane SHEPHERDSTOWN, WV May/June 2026 delivery!! Home with 2 + / - acres situated in the new community of Hallmark...	5 beds \| 6 baths \| 4,114 sq.ft.	$949,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.7% Airbnb Rental Income: $null Traditional Rental Income: $5698 Airbnb ROI: N/A Traditional ROI: 4.7%
17 MISTLETOE Lane SHEPHERDSTOWN, WV New 19 home Community in Shepherdstown!! Welcome to Hallmark Glen! March 2026 delivery on ...	5 beds \| 5 baths \| 4,328 sq.ft.	$1,199,999	Airbnb cash on cash: N/A Traditional cash on cash: 1.8% Airbnb Rental Income: $null Traditional Rental Income: $3912 Airbnb ROI: N/A Traditional ROI: 1.8%
9 MISTLETOE Lane SHEPHERDSTOWN, WV Delivery late February or early March 2026!!! Timeless Colonial Charm Meets Modern Comfort...	4 beds \| 6 baths \| 4,016 sq.ft.	$899,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.46% Airbnb Rental Income: $null Traditional Rental Income: $5207 Airbnb ROI: N/A Traditional ROI: 4.46%
157 Lyon Rdg SHEPHERDSTOWN, WV 157 Lyon Rdg, SHEPHERDSTOWN, WV 25443 \| Single Family Residential	4 beds \| 2 baths \| 1,906 sq.ft.	$429,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.17% Airbnb Rental Income: $null Traditional Rental Income: $2484 Airbnb ROI: N/A Traditional ROI: 4.17%
49 S Tamarac Dr SHEPHERDSTOWN, WV 49 S Tamarac Dr, SHEPHERDSTOWN, WV 25443 \| Single Family Residential	3 beds \| 3 baths \| 1,832 sq.ft.	$600,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 1.14% Airbnb Rental Income: $1221 Traditional Rental Income: $1612 Airbnb ROI: -0.26% Traditional ROI: 1.14%
Unnumbered Lot Ledge-Lowe Off Shepherd Ln SHEPHERDSTOWN, WV Unnumbered Lot Ledge-Lowe Off Shepherd Ln, SHEPHERDSTOWN, WV 25443 \| Other	N/A beds \| N/A baths \| N/A	$140,000	Airbnb cash on cash: 3.65% Traditional cash on cash: 0.21% Airbnb Rental Income: $1204 Traditional Rental Income: $353 Airbnb ROI: 3.65% Traditional ROI: 0.21%
Lot #20 Shepherds Cove Swift River Way SHEPHERDSTOWN, WV Lot #20 Shepherds Cove Swift River Way, SHEPHERDSTOWN, WV 25443 \| Other	N/A beds \| N/A baths \| N/A	$209,000	Airbnb cash on cash: 0.92% Traditional cash on cash: -1.41% Airbnb Rental Income: $1204 Traditional Rental Income: $353 Airbnb ROI: 0.92% Traditional ROI: -1.41%

Real Estate investment in Shepherdstown, WV

There are 33 properties for sale in the city of Shepherdstown . The median list price in Shepherdstown is $500,000 and the average price per square foot is $176. In February 2026, the average monthly cash on cash return in Shepherdstown is 2.00%. The average monthly rental income in Shepherdstown is $1,921.

Shepherdstown, WV Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 33 investment properties available for sale in Shepherdstown.

In 2026, the best neighborhood to buy investment property is SHEPHERDSTOWN.

The ROI for Short-Term is higher than the Long-Term in Shepherdstown with average rental income of $1,221.

Your search for investment property begins and ends here

Investment Property for Sale in Shepherdstown, WV

32 SCOTT Drive

SHEPHERDSTOWN, WV

3 beds | 3 baths | 1,920 sq.ft.

$289,900

Airbnb cash on cash: 1.14%

Traditional cash on cash: 5.64%

Airbnb Rental Income: $1221

Traditional Rental Income: $2057

Airbnb ROI: 1.14%

Traditional ROI: 5.64%

4781 Scrabble Rd

SHEPHERDSTOWN, WV

5 beds | 2 baths | 2,721 sq.ft.

$695,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.07%

Airbnb Rental Income: $null

Traditional Rental Income: $2647

Airbnb ROI: N/A

Traditional ROI: 2.07%

44 N TAMARAC Drive

SHEPHERDSTOWN, WV

3 beds | 3 baths | 2,975 sq.ft.

$625,000

Airbnb cash on cash: -0.33%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $1221

Traditional Rental Income: $2482

Airbnb ROI: -0.33%

Traditional ROI: 2.51%

115 SWEARINGEN Way

SHEPHERDSTOWN, WV

4 beds | 3 baths | 2,220 sq.ft.

$299,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.44%

Airbnb Rental Income: $null

Traditional Rental Income: $2411

Airbnb ROI: N/A

Traditional ROI: 6.44%

12 MISTLETOE Lane

SHEPHERDSTOWN, WV

4 beds | 6 baths | 4,066 sq.ft.

$999,999

Airbnb cash on cash: N/A

Traditional cash on cash: 3.86%

Airbnb Rental Income: $null

Traditional Rental Income: $5207

Airbnb ROI: N/A

Traditional ROI: 3.86%

5 JINGLE BELLS Court

SHEPHERDSTOWN, WV

4 beds | 4 baths | 2,709 sq.ft.

$799,999

Airbnb cash on cash: N/A

Traditional cash on cash: 1.06%

Airbnb Rental Income: $null

Traditional Rental Income: $2117

Airbnb ROI: N/A

Traditional ROI: 1.06%

150 Morgana Dr

SHEPHERDSTOWN, WV

4 beds | 4 baths | 3,060 sq.ft.

$649,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.83%

Airbnb Rental Income: $null

Traditional Rental Income: $2200

Airbnb ROI: N/A

Traditional ROI: 1.83%

19 MISTLETOE Lane

SHEPHERDSTOWN, WV

5 beds | 6 baths | 4,114 sq.ft.

$949,999

Airbnb cash on cash: N/A

Traditional cash on cash: 4.7%

Airbnb Rental Income: $null

Traditional Rental Income: $5698

Airbnb ROI: N/A