Real Estate Investment Properties for Sale in Chesapeake Beach, MD

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3902 Bayview Dr CHESAPEAKE BEACH, MD Relax on the front porch and take in the Chesapeake Bay views from this spacious home in t...	3 beds \| 2 baths \| 2,336 sq.ft.	$565,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 3.3% Airbnb Rental Income: $1999 Traditional Rental Income: $2860 Airbnb ROI: 0.68% Traditional ROI: 3.3%
3709 29th St CHESAPEAKE BEACH, MD GREAT NEW PRICE AND VALUEWelcome to your Chesapeake Bay retreat-where comfort, style, ...	3 beds \| 2 baths \| 2,283 sq.ft.	$469,900	Airbnb cash on cash: 1.43% Traditional cash on cash: 4.48% Airbnb Rental Income: $1999 Traditional Rental Income: $2816 Airbnb ROI: 1.43% Traditional ROI: 4.48%
3545 CHRISTIANA Court CHESAPEAKE BEACH, MD One-Year Home Warranty Included at Settlement - If you're looking for a home that feels ca...	5 beds \| 3 baths \| 3,137 sq.ft.	$529,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.79% Airbnb Rental Income: $null Traditional Rental Income: $3449 Airbnb ROI: N/A Traditional ROI: 4.79%
3728 Chesapeake Beach Rd E CHESAPEAKE BEACH, MD Exciting opportunity to own this charming 2-bedroom, 1-bath rambler located just three blo...	2 beds \| 1 baths \| 1,364 sq.ft.	$279,000	Airbnb cash on cash: 4.01% Traditional cash on cash: 4.18% Airbnb Rental Income: $2167 Traditional Rental Income: $1662 Airbnb ROI: 4.01% Traditional ROI: 4.18%
3907 16th St CHESAPEAKE BEACH, MD 5 bedrooms, 3 full bathrooms, 4 car garage, 3 attics, no HOA, parking for RV's, boats, tra...	5 beds \| 3 baths \| 1,872 sq.ft.	$530,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.88% Airbnb Rental Income: $null Traditional Rental Income: $3325 Airbnb ROI: N/A Traditional ROI: 4.88%
3164 Dalrymple Rd CHESAPEAKE BEACH, MD 3164 Dalrymple Rd, CHESAPEAKE BEACH, MD 20732 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$90,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 4.6% Airbnb Rental Income: $615 Traditional Rental Income: $680 Airbnb ROI: 0.55% Traditional ROI: 4.6%
10th St CHESAPEAKE BEACH, MD 10th St, CHESAPEAKE BEACH, MD 20732 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$40,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 9.48% Airbnb Rental Income: $615 Traditional Rental Income: $680 Airbnb ROI: 2.48% Traditional ROI: 9.48%

Real Estate investment in Chesapeake-beach, MD

There are 22 properties for sale in the city of Chesapeake Beach . The median list price in Chesapeake Beach is $370,000 and the average price per square foot is $187. In February 2026, the average monthly cash on cash return in Chesapeake Beach is 5.00%. The average monthly rental income in Chesapeake Beach is $2,816.

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

There are 22 investment properties available for sale in Chesapeake-beach.

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

The ROI for Long-Term is higher than the Short-Term in Chesapeake-beach with average rental income of $2,816.

Your search for investment property begins and ends here

Investment Property for Sale in Chesapeake Beach, MD

3902 Bayview Dr

CHESAPEAKE BEACH, MD

3 beds | 2 baths | 2,336 sq.ft.

$565,000

Airbnb cash on cash: 0.68%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $1999

Traditional Rental Income: $2860

Airbnb ROI: 0.68%

Traditional ROI: 3.3%

3709 29th St

CHESAPEAKE BEACH, MD

3 beds | 2 baths | 2,283 sq.ft.

$469,900

Airbnb cash on cash: 1.43%

Traditional cash on cash: 4.48%

Airbnb Rental Income: $1999

Traditional Rental Income: $2816

Airbnb ROI: 1.43%

Traditional ROI: 4.48%

3545 CHRISTIANA Court

CHESAPEAKE BEACH, MD

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

$529,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.79%

Airbnb Rental Income: $null

Traditional Rental Income: $3449

Airbnb ROI: N/A

Traditional ROI: 4.79%

3728 Chesapeake Beach Rd E

CHESAPEAKE BEACH, MD

2 beds | 1 baths | 1,364 sq.ft.

$279,000

Airbnb cash on cash: 4.01%

Traditional cash on cash: 4.18%

Airbnb Rental Income: $2167

Traditional Rental Income: $1662

Airbnb ROI: 4.01%

Traditional ROI: 4.18%

3907 16th St

CHESAPEAKE BEACH, MD

5 beds | 3 baths | 1,872 sq.ft.

$530,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.88%

Airbnb Rental Income: $null

Traditional Rental Income: $3325

Airbnb ROI: N/A

Traditional ROI: 4.88%

3164 Dalrymple Rd

CHESAPEAKE BEACH, MD

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

$90,000

Airbnb cash on cash: 0.55%

Traditional cash on cash: 4.6%

Airbnb Rental Income: $615

Traditional Rental Income: $680

Airbnb ROI: 0.55%

Traditional ROI: 4.6%

10th St

CHESAPEAKE BEACH, MD

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

$40,000

Airbnb cash on cash: 2.48%

Traditional cash on cash: 9.48%

Airbnb Rental Income: $615

Traditional Rental Income: $680

Airbnb ROI: 2.48%

Traditional ROI: 9.48%

Real Estate investment in Chesapeake-beach, MD

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

How many investment properties are available for sale in Chesapeake-beach?

Which neighborhoods in Chesapeake-beach to invest in 2026?

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

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