Real Estate Investment Properties for Sale in Chesapeake City, MD

Looking for investment property in Chesapeake City, MD with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
321 Cecil St CHESAPEAKE CITY, MD Charming 3 bedroom home just two blocks from the C & D Canal and Michael Castle Trail. Bui...	3 beds \| 1 baths \| 3,792 sq.ft.	$320,000	Airbnb cash on cash: 5.34% Traditional cash on cash: 3.3% Airbnb Rental Income: $2885 Traditional Rental Income: $1601 Airbnb ROI: 5.34% Traditional ROI: 3.3%
534 Biddle St CHESAPEAKE CITY, MD Enjoy this million dollar view of the historic C&D Canal at an affordable price! Located i...	2 beds \| 1 baths \| 1,200 sq.ft.	$330,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 3.44% Airbnb Rental Income: $1388 Traditional Rental Income: $1756 Airbnb ROI: 0.9% Traditional ROI: 3.44%
330 Cecil St CHESAPEAKE CITY, MD 330 Cecil St, CHESAPEAKE CITY, MD 21915 \| Single Family Residential	3 beds \| 2 baths \| 1,960 sq.ft.	$619,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 1.72% Airbnb Rental Income: $2885 Traditional Rental Income: $2291 Airbnb ROI: 1.59% Traditional ROI: 1.72%
1455 Cayots Corner Rd CHESAPEAKE CITY, MD 1455 Cayots Corner Rd, CHESAPEAKE CITY, MD 21915 \| Single Family Residential	4 beds \| 3 baths \| 0 sq.ft.	$19,900,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.87% Airbnb Rental Income: $null Traditional Rental Income: $4117 Airbnb ROI: N/A Traditional ROI: -1.87%
614 Biddle St CHESAPEAKE CITY, MD 614 Biddle St, CHESAPEAKE CITY, MD 21915 \| Single Family Residential	3 beds \| 3 baths \| 2,310 sq.ft.	$649,500	Airbnb cash on cash: 1.42% Traditional cash on cash: 1.63% Airbnb Rental Income: $2885 Traditional Rental Income: $2345 Airbnb ROI: 1.42% Traditional ROI: 1.63%
Gour Rd CHESAPEAKE CITY, MD Gour Rd, CHESAPEAKE CITY, MD 21915 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$69,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.43% Airbnb Rental Income: $null Traditional Rental Income: $926 Airbnb ROI: N/A Traditional ROI: 9.43%
953 Court House Point Rd CHESAPEAKE CITY, MD 953 Court House Point Rd, CHESAPEAKE CITY, MD 21915 \| Single Family Residential	3 beds \| 2 baths \| 1,189 sq.ft.	$369,999	Airbnb cash on cash: 3.94% Traditional cash on cash: 2.32% Airbnb Rental Income: $2885 Traditional Rental Income: $1648 Airbnb ROI: 3.94% Traditional ROI: 2.32%
409 Biddle St CHESAPEAKE CITY, MD 409 Biddle St, CHESAPEAKE CITY, MD 21915 \| Townhouse	3 beds \| 1 baths \| 1,120 sq.ft.	$274,900	Airbnb cash on cash: 6.11% Traditional cash on cash: 2.55% Airbnb Rental Income: $2885 Traditional Rental Income: $1293 Airbnb ROI: 6.11% Traditional ROI: 2.55%

Real Estate investment in Chesapeake-city, MD

There are 9 properties for sale in the city of Chesapeake City . The median list price in Chesapeake City is $352,500 and the average price per square foot is $244. In February 2026, the average monthly cash on cash return in Chesapeake City is 2.00%. The average monthly rental income in Chesapeake City is $1,702.

Chesapeake-city, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 9 investment properties available for sale in Chesapeake-city.

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

The ROI for Short-Term is higher than the Long-Term in Chesapeake-city with average rental income of $2,885.

Your search for investment property begins and ends here

Investment Property for Sale in Chesapeake City, MD

321 Cecil St

CHESAPEAKE CITY, MD

3 beds | 1 baths | 3,792 sq.ft.

$320,000

Airbnb cash on cash: 5.34%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $2885

Traditional Rental Income: $1601

Airbnb ROI: 5.34%

Traditional ROI: 3.3%

534 Biddle St

CHESAPEAKE CITY, MD

2 beds | 1 baths | 1,200 sq.ft.

$330,000

Airbnb cash on cash: 0.9%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $1388

Traditional Rental Income: $1756

Airbnb ROI: 0.9%

Traditional ROI: 3.44%

330 Cecil St

CHESAPEAKE CITY, MD

3 beds | 2 baths | 1,960 sq.ft.

$619,000

Airbnb cash on cash: 1.59%

Traditional cash on cash: 1.72%

Airbnb Rental Income: $2885

Traditional Rental Income: $2291

Airbnb ROI: 1.59%

Traditional ROI: 1.72%

1455 Cayots Corner Rd

CHESAPEAKE CITY, MD

4 beds | 3 baths | 0 sq.ft.

$19,900,000

Airbnb cash on cash: N/A

Traditional cash on cash: -1.87%

Airbnb Rental Income: $null

Traditional Rental Income: $4117

Airbnb ROI: N/A

Traditional ROI: -1.87%

614 Biddle St

CHESAPEAKE CITY, MD

3 beds | 3 baths | 2,310 sq.ft.

$649,500

Airbnb cash on cash: 1.42%

Traditional cash on cash: 1.63%

Airbnb Rental Income: $2885

Traditional Rental Income: $2345

Airbnb ROI: 1.42%

Traditional ROI: 1.63%

Gour Rd

CHESAPEAKE CITY, MD

N/A beds | N/A baths | 0 sq.ft.

$69,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.43%

Airbnb Rental Income: $null

Traditional Rental Income: $926

Airbnb ROI: N/A

Traditional ROI: 9.43%

953 Court House Point Rd

CHESAPEAKE CITY, MD

3 beds | 2 baths | 1,189 sq.ft.

$369,999

Airbnb cash on cash: 3.94%

Traditional cash on cash: 2.32%

Airbnb Rental Income: $2885

Traditional Rental Income: $1648

Airbnb ROI: 3.94%

Traditional ROI: 2.32%

409 Biddle St

CHESAPEAKE CITY, MD

3 beds | 1 baths | 1,120 sq.ft.

$274,900

Airbnb cash on cash: 6.11%

Traditional cash on cash: 2.55%

Airbnb Rental Income: $2885

Traditional Rental Income: $1293

Airbnb ROI: 6.11%