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
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: 0.19% Traditional cash on cash: 3.19% Airbnb Rental Income: $1261 Traditional Rental Income: $2264 Airbnb ROI: 0.19% Traditional ROI: 3.19%
ROLLIE ROAD E 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: -0.38% Traditional cash on cash: 1.6% Airbnb Rental Income: $1261 Traditional Rental Income: $2848 Airbnb ROI: -0.38% Traditional ROI: 1.6%
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: N/A Traditional cash on cash: 1.73% Airbnb Rental Income: $null Traditional Rental Income: $5105 Airbnb ROI: N/A Traditional ROI: 1.73%
13374 COVE LANDING RD Bishopville, MD Introducing 13374 Cove Landing Rd. - A Waterfront Gem with Endless Potential Nestled on ne...	4 beds \| 2 baths \| N/A	$580,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 3.35% Airbnb Rental Income: $2113 Traditional Rental Income: $2776 Airbnb ROI: 1.13% Traditional ROI: 3.35%
Investment Properties for Sale in Other Cities of Maryland
20117 LAUREL HILL Way Germantown , MD Nicely updated townhouse with lake views, kitchen with Granite tops, stainless steel appli...	2 beds \| 3 baths \| 2,066 sq.ft.	$399,900	Airbnb cash on cash: 0.53% Traditional cash on cash: 4.83% Airbnb Rental Income: $1455 Traditional Rental Income: $2635 Airbnb ROI: 0.53% Traditional ROI: 4.83%
3029 HUDSON Street Baltimore , MD Welcome to this beautifully reimagined Canton residence, where historic charm meets modern...	4 beds \| 3 baths \| 1,748 sq.ft.	$495,000	Airbnb cash on cash: 5.5% Traditional cash on cash: 3.56% Airbnb Rental Income: $4486 Traditional Rental Income: $2649 Airbnb ROI: 5.5% Traditional ROI: 3.56%
1518 E 28TH ST Baltimore , MD An amazing opportunity if you are looking to invest as an investor or as a first time home...	3 beds \| 2 baths \| N/A	$134,900	Airbnb cash on cash: 2.79% Traditional cash on cash: 11.89% Airbnb Rental Income: $1155 Traditional Rental Income: $1952 Airbnb ROI: 2.79% Traditional ROI: 11.89%
827 LIGHT Street Baltimore , MD With over $300,000 in upgrades, this home perfectly blends historic charm with modern luxu...	3 beds \| 4 baths \| 2,736 sq.ft.	$528,695	Airbnb cash on cash: -0.75% Traditional cash on cash: 2.96% Airbnb Rental Income: $1500 Traditional Rental Income: $2894 Airbnb ROI: -0.75% Traditional ROI: 2.96%
675 PRESIDENT Street unit: 2904 #2904 Baltimore , MD Elevated high above Harbor East, this impeccable two-story penthouse at The Vue offers an ...	4 beds \| 4 baths \| 5,071 sq.ft.	$2,695,000	Airbnb cash on cash: -1.57% Traditional cash on cash: -0.5% Airbnb Rental Income: $1948 Traditional Rental Income: $4106 Airbnb ROI: -1.57% Traditional ROI: -0.5%
1243 BATTERY Avenue Baltimore , MD Back on the Market! Motivated Seller - Bonus Offered with Full-Price Offer! Welcome to you...	2 beds \| 2 baths \| 1,730 sq.ft.	$300,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 3.76% Airbnb Rental Income: $1224 Traditional Rental Income: $2216 Airbnb ROI: -1.14% Traditional ROI: 3.76%
3916 CLOVERHILL Road Baltimore , MD Discover your charming retreat in the heart of Tuscany/Canterbury. This delightful 5-bedro...	5 beds \| 2 baths \| 2,016 sq.ft.	$530,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.56% Airbnb Rental Income: $null Traditional Rental Income: $2612 Airbnb ROI: N/A Traditional ROI: 2.56%
16 138TH Street unit: 106 #106 Ocean City , MD Expansive 4-Bedroom Condo with Ocean Views in Island Breeze - Rarely Available! Welcome to...	4 beds \| 3 baths \| 2,570 sq.ft.	$950,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 1.53% Airbnb Rental Income: $4007 Traditional Rental Income: $3157 Airbnb ROI: 1.52% Traditional ROI: 1.53%
32 EAST Street Annapolis , MD	3 beds \| 3 baths \| 2,100 sq.ft.	$1,200,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 0.14% Airbnb Rental Income: $2680 Traditional Rental Income: $2245 Airbnb ROI: -0.04% Traditional ROI: 0.14%
23 STONEHENGE CIR #8 PIKESVILLE , MD Discover the charm of this beautifully maintained 2-bedroom, 2-bathroom condo in Stevenson...	2 beds \| 2 baths \| N/A	$229,224	Airbnb cash on cash: 2.28% Traditional cash on cash: 6.04% Airbnb Rental Income: $1384 Traditional Rental Income: $1778 Airbnb ROI: 2.28% Traditional ROI: 6.04%
500 FAIRWAY Court Baltimore , MD Welcome to this timeless and completely remodeled split-level home located at 500 Fairway ...	3 beds \| 3 baths \| 1,706 sq.ft.	$514,990	Airbnb cash on cash: 2.13% Traditional cash on cash: 3.99% Airbnb Rental Income: $2608 Traditional Rental Income: $2878 Airbnb ROI: 2.13% Traditional ROI: 3.99%
2933 FAIT Avenue Baltimore , MD Enjoy City life in this fully remolded home in Canton. The open floor plan of the main lev...	3 beds \| 3 baths \| 1,152 sq.ft.	$449,999	Airbnb cash on cash: 3.23% Traditional cash on cash: 2.09% Airbnb Rental Income: $3308 Traditional Rental Income: $2089 Airbnb ROI: 3.23% Traditional ROI: 2.09%
1433 E FEDERAL Street Baltimore , MD Welcome to your next investment opportunity at 1433 E Federal Street! This fully renovated...	3 beds \| 3 baths \| N/A	$220,000	Airbnb cash on cash: 7.63% Traditional cash on cash: 9.11% Airbnb Rental Income: $2949 Traditional Rental Income: $2577 Airbnb ROI: 7.63% Traditional ROI: 9.11%
414 WATER Street unit: 2805 #2805 Baltimore , MD Discover the best of urban living in this high-rise condominium, ideally located in the he...	2 beds \| 1 baths \| 789 sq.ft.	$149,900	Airbnb cash on cash: 2.54% Traditional cash on cash: 9.47% Airbnb Rental Income: $1389 Traditional Rental Income: $1963 Airbnb ROI: 2.54% Traditional ROI: 9.47%
320 S HIGHLAND Avenue Baltimore , MD MULTI FAMILY OFFERING IN HIGHLANDTOWN WITH INCERDIBLE VIEWS OF DOWNTOWN & PATTERSON PARK W...	N/A beds \| N/A baths \| 3,340 sq.ft.	$1,150,000	Airbnb cash on cash: -1% Traditional cash on cash: -0.31% Airbnb Rental Income: $1379 Traditional Rental Income: $1703 Airbnb ROI: -1% Traditional ROI: -0.31%

Real Estate investment in Bishopville, MD

There are 4 properties for sale in the city of Bishopville . The median list price in Bishopville is $539,500 and the average price per square foot is $414. In November 2025, the average monthly cash on cash return in Bishopville is 3.00%. The average monthly rental income in Bishopville is $2,603.

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

There are 4 investment properties available for sale in Bishopville.

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

The ROI for Long-Term is higher than the Short-Term in Bishopville with average rental income of $2,603.

Your search for investment property begins and ends here

Investment Property for Sale in Bishopville, MD

9401 FOOKS Road

Bishopville, MD

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

$499,000

Airbnb cash on cash: 0.19%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $1261

Traditional Rental Income: $2264

Airbnb ROI: 0.19%

Traditional ROI: 3.19%

ROLLIE ROAD E LOTS 29 & 30

Bishopville, MD

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

$1,079,150

Airbnb cash on cash: -0.38%

Traditional cash on cash: 1.6%

Airbnb Rental Income: $1261

Traditional Rental Income: $2848

Airbnb ROI: -0.38%

Traditional ROI: 1.6%

12331 SOUTHHAMPTON DR

Bishopville, MD

5 beds | 5 baths | N/A

$1,590,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.73%

Airbnb Rental Income: $null

Traditional Rental Income: $5105

Airbnb ROI: N/A

Traditional ROI: 1.73%

13374 COVE LANDING RD

Bishopville, MD

4 beds | 2 baths | N/A

$580,000

Airbnb cash on cash: 1.13%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $2113

Traditional Rental Income: $2776

Airbnb ROI: 1.13%

Traditional ROI: 3.35%

Investment Properties for Sale in Other Cities of Maryland

Germantown , MD

2 beds | 3 baths | 2,066 sq.ft.

$399,900

Airbnb cash on cash: 0.53%

Traditional cash on cash: 4.83%

Airbnb Rental Income: $1455

Traditional Rental Income: $2635

Airbnb ROI: 0.53%

Traditional ROI: 4.83%

Baltimore , MD

4 beds | 3 baths | 1,748 sq.ft.

$495,000

Airbnb cash on cash: 5.5%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $4486

Traditional Rental Income: $2649

Airbnb ROI: 5.5%

Traditional ROI: 3.56%

Baltimore , MD

3 beds | 2 baths | N/A

$134,900

Airbnb cash on cash: 2.79%

Traditional cash on cash: 11.89%

Airbnb Rental Income: $1155

Traditional Rental Income: $1952

Airbnb ROI: 2.79%

Traditional ROI: 11.89%

Baltimore , MD

3 beds | 4 baths | 2,736 sq.ft.

$528,695

Airbnb cash on cash: -0.75%

Traditional cash on cash: 2.96%

Airbnb Rental Income: $1500

Traditional Rental Income: $2894

Airbnb ROI: -0.75%

Traditional ROI: 2.96%

Baltimore , MD

4 beds | 4 baths | 5,071 sq.ft.