Real Estate Investment Properties for Sale in Bishopville, MD

Looking for investment property in Bishopville, MD with high ROI ?

Explore a variety of short-term homes & houses in Bishopville, MD. Invest wisely with VRBO & Bishopville, MD 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 Bishopville, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
10651 PINEY ISLAND DRIVE Bishopville, MD Back on the market with a New Price! Discover a rare opportunity in Piney Island, a peacef...	4 beds \| 4 baths \| 2,877 sq.ft.	$795,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 3.2% Airbnb Rental Income: $1643 Traditional Rental Income: $3525 Airbnb ROI: 0.04% Traditional ROI: 3.2%
9401 FOOKS ROAD Bishopville, MD This is an extra special rare find - a totally renovated home on 1.32 Acres with Commercia...	3 beds \| 2 baths \| 1,248 sq.ft.	$499,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 3.19% Airbnb Rental Income: $1531 Traditional Rental Income: $2264 Airbnb ROI: 0.67% Traditional ROI: 3.19%
12264 DIXIE DRIVE Bishopville, MD Welcome to 12264 Dixie Drive! A rare and exceptional Riverfront property located on a spac...	3 beds \| 3 baths \| 2,090 sq.ft.	$1,095,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 1.74% Airbnb Rental Income: $1531 Traditional Rental Income: $3307 Airbnb ROI: -0.44% Traditional ROI: 1.74%
12331 SOUTHHAMPTON DR Bishopville, MD A Coastal Masterpiece with Unmatched Views! This one-of-a-kind custom residence-featured ...	5 beds \| 5 baths \| N/A	$1,590,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 1.73% Airbnb Rental Income: $3373 Traditional Rental Income: $5105 Airbnb ROI: 0.05% Traditional ROI: 1.73%
ROLLIE ROAD EAST, LOTS 29 & 30 Bishopville, MD Lot & Home Package by Bay to Beach Builders, award winning for their Amish Crafted Custom ...	3 beds \| 2 baths \| 2,459 sq.ft.	$1,079,150	Airbnb cash on cash: -0.15% Traditional cash on cash: 1.6% Airbnb Rental Income: $1531 Traditional Rental Income: $2848 Airbnb ROI: -0.15% Traditional ROI: 1.6%
12232 LOIS STREET Bishopville, MD Beautiful waterfront home in Holiday Harbor. End of street on canal with open water views....	4 beds \| 3 baths \| 2,192 sq.ft.	$949,900	Airbnb cash on cash: -0.12% Traditional cash on cash: 2.49% Airbnb Rental Income: $1643 Traditional Rental Income: $3489 Airbnb ROI: -0.12% Traditional ROI: 2.49%
12360 POINT VIEW ROAD Bishopville, MD This 3 Bedroom 2 Bath single-level home is canal front, with access to the open bay and th...	3 beds \| 2 baths \| 2,137 sq.ft.	$799,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 1.89% Airbnb Rental Income: $1531 Traditional Rental Income: $2657 Airbnb ROI: -0.22% Traditional ROI: 1.89%

Real Estate investment in Bishopville, MD

There are 7 properties for sale in the city of Bishopville . The median list price in Bishopville is $949,900 and the average price per square foot is $438. In September 2025, the average monthly cash on cash return in Bishopville is 2.00%. The average monthly rental income in Bishopville is $3,307.

Bishopville, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 7 investment properties available for sale in Bishopville.

In 2025, the best neighborhood to buy investment property is Bishopville.

The ROI for Short-Term is higher than the Long-Term in Bishopville with average rental income of $1,531.

Your search for investment property begins and ends here

Investment Property for Sale in Bishopville, MD

10651 PINEY ISLAND DRIVE

Bishopville, MD

4 beds | 4 baths | 2,877 sq.ft.

$795,000

Airbnb cash on cash: 0.04%

Traditional cash on cash: 3.2%

Airbnb Rental Income: $1643

Traditional Rental Income: $3525

Airbnb ROI: 0.04%

Traditional ROI: 3.2%

9401 FOOKS ROAD

Bishopville, MD

3 beds | 2 baths | 1,248 sq.ft.

$499,000

Airbnb cash on cash: 0.67%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $1531

Traditional Rental Income: $2264

Airbnb ROI: 0.67%

Traditional ROI: 3.19%

12264 DIXIE DRIVE

Bishopville, MD

3 beds | 3 baths | 2,090 sq.ft.

$1,095,000

Airbnb cash on cash: -0.44%

Traditional cash on cash: 1.74%

Airbnb Rental Income: $1531

Traditional Rental Income: $3307

Airbnb ROI: -0.44%

Traditional ROI: 1.74%

12331 SOUTHHAMPTON DR

Bishopville, MD

5 beds | 5 baths | N/A

$1,590,000

Airbnb cash on cash: 0.05%

Traditional cash on cash: 1.73%

Airbnb Rental Income: $3373

Traditional Rental Income: $5105

Airbnb ROI: 0.05%

Traditional ROI: 1.73%

ROLLIE ROAD EAST, LOTS 29 & 30

Bishopville, MD

3 beds | 2 baths | 2,459 sq.ft.

$1,079,150

Airbnb cash on cash: -0.15%

Traditional cash on cash: 1.6%

Airbnb Rental Income: $1531

Traditional Rental Income: $2848

Airbnb ROI: -0.15%

Traditional ROI: 1.6%

12232 LOIS STREET

Bishopville, MD

4 beds | 3 baths | 2,192 sq.ft.

$949,900

Airbnb cash on cash: -0.12%

Traditional cash on cash: 2.49%

Airbnb Rental Income: $1643

Traditional Rental Income: $3489

Airbnb ROI: -0.12%

Traditional ROI: 2.49%

12360 POINT VIEW ROAD

Bishopville, MD

3 beds | 2 baths | 2,137 sq.ft.

$799,000

Airbnb cash on cash: -0.22%

Traditional cash on cash: 1.89%

Airbnb Rental Income: $1531

Traditional Rental Income: $2657

Airbnb ROI: -0.22%

Traditional ROI: 1.89%

Real Estate investment in Bishopville, MD

Bishopville, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

How many investment properties are available for sale in Bishopville?

Which neighborhoods in Bishopville to invest in 2025?

Long-Term vs. Short-Term Rentals in Bishopville, Maryland: Which will earn the best returns?

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