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
240 Randalia Rd CHESAPEAKE CITY, MD Welcome Home! This Is Your Opportunity To Have Your Own Picturesque Family Farm In The Bea...	3 beds \| 3 baths \| 2,480 sq.ft.	$899,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 2.04% Airbnb Rental Income: $2153 Traditional Rental Income: $2859 Airbnb ROI: 0.54% Traditional ROI: 2.04%
904 Biddle St CHESAPEAKE CITY, MD There's no place like home when you live along the Chesapeake & Delaware Canal, offering w...	3 beds \| 2 baths \| 2,464 sq.ft.	$824,904	Airbnb cash on cash: 0.23% Traditional cash on cash: 2.12% Airbnb Rental Income: $2153 Traditional Rental Income: $3056 Airbnb ROI: 0.23% Traditional ROI: 2.12%
330 Cecil St CHESAPEAKE CITY, MD 330 Cecil St, CHESAPEAKE CITY, MD 21915 \| Single Family Residential	3 beds \| 2 baths \| 1,960 sq.ft.	$549,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 2.2% Airbnb Rental Income: $2153 Traditional Rental Income: $2291 Airbnb ROI: 0.87% Traditional ROI: 2.2%
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: -2.02% Traditional cash on cash: -1.87% Airbnb Rental Income: $1686 Traditional Rental Income: $4117 Airbnb ROI: -2.02% Traditional ROI: -1.87%
344 Cayots Corner Rd CHESAPEAKE CITY, MD Welcome Home To Your 3 Bedroom Chesapeake City Rancher Located Just Outside Of Town, Peace...	3 beds \| 1 baths \| 760 sq.ft.	$259,000	Airbnb cash on cash: 4.5% Traditional cash on cash: 4.83% Airbnb Rental Income: $2153 Traditional Rental Income: $1688 Airbnb ROI: 4.5% Traditional ROI: 4.83%
8 Maryland Ave CHESAPEAKE CITY, MD For boaters who don't want the waterfront price tag...this is it! Just steps to the commun...	2 beds \| 2 baths \| 1,120 sq.ft.	$369,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 3.62% Airbnb Rental Income: $1626 Traditional Rental Income: $1960 Airbnb ROI: 1.33% Traditional ROI: 3.62%
320 Cecil St CHESAPEAKE CITY, MD This Folk Victorian home, featuring gingerbread trim and over 2000 sq ft., offers a versat...	3 beds \| 2 baths \| 2,263 sq.ft.	$350,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 3.87% Airbnb Rental Income: $2153 Traditional Rental Income: $1984 Airbnb ROI: 2.72% Traditional ROI: 3.87%
0 Cecil St CHESAPEAKE CITY, MD 0 Cecil St, CHESAPEAKE CITY, MD 21915 \| Other	N/A beds \| N/A baths \| N/A	$65,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.69% Airbnb Rental Income: $null Traditional Rental Income: $660 Airbnb ROI: N/A Traditional ROI: 6.69%
246 Biddle St CHESAPEAKE CITY, MD There's no place like home at 246 Biddle Street, a Victorian home full of Chesapeake City ...	4 beds \| 3 baths \| 3,280 sq.ft.	$699,999	Airbnb cash on cash: -0.17% Traditional cash on cash: 3.55% Airbnb Rental Income: $1686 Traditional Rental Income: $3649 Airbnb ROI: -0.17% Traditional ROI: 3.55%
Chestnut Springs Rd CHESAPEAKE CITY, MD Chestnut Springs Rd, CHESAPEAKE CITY, MD 21915 \| Other	N/A beds \| N/A baths \| N/A	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.57% Airbnb Rental Income: $null Traditional Rental Income: $659 Airbnb ROI: N/A Traditional ROI: -0.57%

Real Estate investment in Chesapeake-city, MD

There are 10 properties for sale in the city of Chesapeake City . The median list price in Chesapeake City is $399,794 and the average price per square foot is $235. In June 2026, the average monthly cash on cash return in Chesapeake City is 4.00%. The average monthly rental income in Chesapeake City is $1,972.

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

There are 10 investment properties available for sale in Chesapeake-city.

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

The ROI for Long-Term is higher than the Short-Term in Chesapeake-city with average rental income of $1,972.

Your search for investment property begins and ends here

Investment Property for Sale in Chesapeake City, MD

240 Randalia Rd

CHESAPEAKE CITY, MD

3 beds | 3 baths | 2,480 sq.ft.

$899,000

Airbnb cash on cash: 0.54%

Traditional cash on cash: 2.04%

Airbnb Rental Income: $2153

Traditional Rental Income: $2859

Airbnb ROI: 0.54%

Traditional ROI: 2.04%

904 Biddle St

CHESAPEAKE CITY, MD

3 beds | 2 baths | 2,464 sq.ft.

$824,904

Airbnb cash on cash: 0.23%

Traditional cash on cash: 2.12%

Airbnb Rental Income: $2153

Traditional Rental Income: $3056

Airbnb ROI: 0.23%

Traditional ROI: 2.12%

330 Cecil St

CHESAPEAKE CITY, MD

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

$549,000

Airbnb cash on cash: 0.87%

Traditional cash on cash: 2.2%

Airbnb Rental Income: $2153

Traditional Rental Income: $2291

Airbnb ROI: 0.87%

Traditional ROI: 2.2%

1455 Cayots Corner Rd

CHESAPEAKE CITY, MD

4 beds | 3 baths | 0 sq.ft.

$19,900,000

Airbnb cash on cash: -2.02%

Traditional cash on cash: -1.87%

Airbnb Rental Income: $1686

Traditional Rental Income: $4117

Airbnb ROI: -2.02%

Traditional ROI: -1.87%

344 Cayots Corner Rd

CHESAPEAKE CITY, MD

3 beds | 1 baths | 760 sq.ft.

$259,000

Airbnb cash on cash: 4.5%

Traditional cash on cash: 4.83%

Airbnb Rental Income: $2153

Traditional Rental Income: $1688

Airbnb ROI: 4.5%

Traditional ROI: 4.83%

8 Maryland Ave

CHESAPEAKE CITY, MD

2 beds | 2 baths | 1,120 sq.ft.

$369,000

Airbnb cash on cash: 1.33%

Traditional cash on cash: 3.62%

Airbnb Rental Income: $1626

Traditional Rental Income: $1960

Airbnb ROI: 1.33%

Traditional ROI: 3.62%

320 Cecil St

CHESAPEAKE CITY, MD

3 beds | 2 baths | 2,263 sq.ft.

$350,000

Airbnb cash on cash: 2.72%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $2153

Traditional Rental Income: $1984

Airbnb ROI: 2.72%

Traditional ROI: 3.87%

0 Cecil St

CHESAPEAKE CITY, MD

N/A beds | N/A baths | N/A

$65,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.69%

Airbnb Rental Income: $null

Traditional Rental Income: $660

Airbnb ROI: N/A