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
8229 BAYSIDE Road CHESAPEAKE BEACH, MD Back on the market due to shaky financing! Inspected and READY! Improved price too! Welcom...	4 beds \| 4 baths \| 2,700 sq.ft.	$777,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 2.73% Airbnb Rental Income: $2994 Traditional Rental Income: $3385 Airbnb ROI: 1.24% Traditional ROI: 2.73%
4011 27TH Street CHESAPEAKE BEACH, MD Everything you want in a true Chesapeake Bay waterfront property is right here. Nestled on...	5 beds \| 4 baths \| 3,100 sq.ft.	$1,300,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.69% Airbnb Rental Income: $null Traditional Rental Income: $4050 Airbnb ROI: N/A Traditional ROI: 1.69%
2425 HARRISON Court CHESAPEAKE BEACH, MD ASSUMABLE 2.25% VA LOAN AVAILABLE (Qualified Buyers - Inquire for Details) Welcome to one ...	4 beds \| 3 baths \| 3,570 sq.ft.	$679,990	Airbnb cash on cash: 1.57% Traditional cash on cash: 2.3% Airbnb Rental Income: $2994 Traditional Rental Income: $2765 Airbnb ROI: 1.57% Traditional ROI: 2.3%
2310 FOREST RIDGE Terrace #6 CHESAPEAKE BEACH, MD Enjoy coastal living in this spacious upper-level penthouse-style condo in the heart of Ch...	3 beds \| 3 baths \| 2,300 sq.ft.	$367,500	Airbnb cash on cash: 1.4% Traditional cash on cash: 6.53% Airbnb Rental Income: $2321 Traditional Rental Income: $3514 Airbnb ROI: 1.4% Traditional ROI: 6.53%
7902 DELORES Court CHESAPEAKE BEACH, MD Fantastic opportunity to own this beautifully maintained END UNIT townhome situated on arg...	4 beds \| 4 baths \| 2,688 sq.ft.	$499,990	Airbnb cash on cash: 2.73% Traditional cash on cash: 3.45% Airbnb Rental Income: $2994 Traditional Rental Income: $2643 Airbnb ROI: 2.73% Traditional ROI: 3.45%
6114 2ND Street CHESAPEAKE BEACH, MD Beautifully renovated split foyer offering fresh updates and move-in ready appeal! Major i...	3 beds \| 2 baths \| 1,716 sq.ft.	$410,000	Airbnb cash on cash: 3.13% Traditional cash on cash: 4.07% Airbnb Rental Income: $2672 Traditional Rental Income: $2398 Airbnb ROI: 3.13% Traditional ROI: 4.07%
3384 CANNONCADE Court CHESAPEAKE BEACH, MD Located in the desirable Chesapeake Village community, this beautiful Colonial-style home ...	5 beds \| 4 baths \| 4,422 sq.ft.	$687,500	Airbnb cash on cash: N/A Traditional cash on cash: 2.89% Airbnb Rental Income: $null Traditional Rental Income: $3277 Airbnb ROI: N/A Traditional ROI: 2.89%
2243 IVY Lane #8 CHESAPEAKE BEACH, MD NEW PRICE to Sell! Welcome to 2,600+ sq. ft. of comfortable living in Richfield Station. S...	3 beds \| 3 baths \| 2,641 sq.ft.	$375,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 3.1% Airbnb Rental Income: $2321 Traditional Rental Income: $2362 Airbnb ROI: 1.35% Traditional ROI: 3.1%
2811 GLASGOW Way CHESAPEAKE BEACH, MD Nestled on a spacious and private 1.28-acre cul-de-sac lot in the highly sought-after High...	3 beds \| 2 baths \| 1,716 sq.ft.	$474,990	Airbnb cash on cash: 1.88% Traditional cash on cash: 3.2% Airbnb Rental Income: $2321 Traditional Rental Income: $2329 Airbnb ROI: 1.88% Traditional ROI: 3.2%
6122 6TH Street CHESAPEAKE BEACH, MD Welcome to charming 6122 6th St, nestled within the Chesapeake Beach community. This home ...	2 beds \| 1 baths \| 719 sq.ft.	$289,900	Airbnb cash on cash: 2.49% Traditional cash on cash: 4.45% Airbnb Rental Income: $1744 Traditional Rental Income: $1801 Airbnb ROI: 2.49% Traditional ROI: 4.45%
8236 BAYSIDE Road CHESAPEAKE BEACH, MD Beach living at its best in the heart of Chesapeake Beach, with bay views right from your ...	4 beds \| 2 baths \| 2,857 sq.ft.	$575,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 3.64% Airbnb Rental Income: $2994 Traditional Rental Income: $3107 Airbnb ROI: 2.15% Traditional ROI: 3.64%
6231 8TH Street CHESAPEAKE BEACH, MD This property is being sold as-is and is perfect for investors, flippers, or buyers lookin...	3 beds \| 2 baths \| 2,597 sq.ft.	$190,000	Airbnb cash on cash: 5.96% Traditional cash on cash: 11.34% Airbnb Rental Income: $2321 Traditional Rental Income: $2716 Airbnb ROI: 5.96% Traditional ROI: 11.34%
8205 F Street CHESAPEAKE BEACH, MD Architecturally distinctive and thoughtfully designed, this exceptional Acorn Deck Home of...	3 beds \| 3 baths \| 2,757 sq.ft.	$479,900	Airbnb cash on cash: 1.53% Traditional cash on cash: 4.88% Airbnb Rental Income: $2321 Traditional Rental Income: $3250 Airbnb ROI: 1.53% Traditional ROI: 4.88%
6130 4TH Street CHESAPEAKE BEACH, MD This 3-bedroom, 1-bath home on 4th Street blends modern updates with coastal charm in a pr...	3 beds \| 1 baths \| 960 sq.ft.	$334,974	Airbnb cash on cash: 3.46% Traditional cash on cash: 3.99% Airbnb Rental Income: $2321 Traditional Rental Income: $1912 Airbnb ROI: 3.46% Traditional ROI: 3.99%
8314 BAYSIDE Road CHESAPEAKE BEACH, MD TO BE BUILT HOME in the sought-after Chesapeake Beach community. This exceptional NEW CONS...	4 beds \| 3 baths \| 1,802 sq.ft.	$699,999	Airbnb cash on cash: 2.22% Traditional cash on cash: 3.21% Airbnb Rental Income: $2994 Traditional Rental Income: $2954 Airbnb ROI: 2.22% Traditional ROI: 3.21%
8047 WINDWARD KEY Drive CHESAPEAKE BEACH, MD Nestled along the tranquil shores of Chesapeake Beach, this stunning four-bedroom, four-an...	4 beds \| 5 baths \| 2,632 sq.ft.	$849,900	Airbnb cash on cash: 0.4% Traditional cash on cash: 3.14% Airbnb Rental Income: $2994 Traditional Rental Income: $4475 Airbnb ROI: 0.4% Traditional ROI: 3.14%
8054 WINDWARD KEY DRIVE CHESAPEAKE BEACH, MD MAJOR PRICE IMPROVEMENT. Experience an elevated waterfront lifestyle in the coveted Windwa...	4 beds \| 5 baths \| 2,876 sq.ft.	$774,900	Airbnb cash on cash: 0.56% Traditional cash on cash: 3.91% Airbnb Rental Income: $2994 Traditional Rental Income: $4727 Airbnb ROI: 0.56% Traditional ROI: 3.91%
8076 WINDWARD KEY Drive CHESAPEAKE BEACH, MD COASTAL LUXURY MEETS EVERYDAY VACATION LIVING in Windward Key on the Chesapeake Bay. Exper...	4 beds \| 5 baths \| 2,950 sq.ft.	$775,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 4.37% Airbnb Rental Income: $2994 Traditional Rental Income: $4933 Airbnb ROI: 0.73% Traditional ROI: 4.37%
4013 SEAGATE SQ CHESAPEAKE BEACH, MD Welcome to 4013 Seagate Square, ideally situated in the heart of Chesapeake Beach-one of t...	3 beds \| 4 baths \| N/A	$485,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 3.27% Airbnb Rental Income: $2321 Traditional Rental Income: $2447 Airbnb ROI: 1.72% Traditional ROI: 3.27%
8048 WINDWARD KEY Drive CHESAPEAKE BEACH, MD Discover coastal living at its finest at 8048 Windward Key Dr, Chesapeake Beach! This "as-...	3 beds \| 5 baths \| 2,583 sq.ft.	$759,900	Airbnb cash on cash: -0.22% Traditional cash on cash: 3.43% Airbnb Rental Income: $2321 Traditional Rental Income: $4333 Airbnb ROI: -0.22% Traditional ROI: 3.43%
3713 & 3711 BAYVIEW DR CHESAPEAKE BEACH, MD Wake up to breathtaking sunrises and sweeping waterfront views in this charming coastal re...	2 beds \| 1 baths \| N/A	$865,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 0.34% Airbnb Rental Income: $1744 Traditional Rental Income: $1591 Airbnb ROI: -0.07% Traditional ROI: 0.34%
3606 27TH Street CHESAPEAKE BEACH, MD NEW PRICE - Location location location - Lovely Chesapeake Beach split foyer with en...	4 beds \| 3 baths \| 2,444 sq.ft.	$437,500	Airbnb cash on cash: 3.63% Traditional cash on cash: 5.52% Airbnb Rental Income: $2994 Traditional Rental Income: $3081 Airbnb ROI: 3.63% Traditional ROI: 5.52%
3325 COX Road CHESAPEAKE BEACH, MD This spacious QBH custom built Colonial offers over 5,000 square feet of living space with...	5 beds \| 5 baths \| 3,863 sq.ft.	$1,050,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.39% Airbnb Rental Income: $null Traditional Rental Income: $3141 Airbnb ROI: N/A Traditional ROI: 1.39%
2630 RICHFIELD Lane CHESAPEAKE BEACH, MD Welcome to 2630 Richfield Lane in Chesapeake Beach! This beautiful 4-bedroom, 2 full bath,...	4 beds \| 3 baths \| 2,276 sq.ft.	$619,900	Airbnb cash on cash: 2.07% Traditional cash on cash: 2.65% Airbnb Rental Income: $2994 Traditional Rental Income: $2643 Airbnb ROI: 2.07% Traditional ROI: 2.65%
7935 EAGLE VIEW Drive CHESAPEAKE BEACH, MD Beautiful home in the highly desirable Richfield Station community offering exceptional li...	2 beds \| 2 baths \| 1,895 sq.ft.	$550,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 3.74% Airbnb Rental Income: $1744 Traditional Rental Income: $2921 Airbnb ROI: 0.52% Traditional ROI: 3.74%

Real Estate investment in Chesapeake-beach, MD

There are 39 properties for sale in the city of Chesapeake Beach . The median list price in Chesapeake Beach is $474,916 and the average price per square foot is $199. In July 2026, the average monthly cash on cash return in Chesapeake Beach is 4.00%. The average monthly rental income in Chesapeake Beach is $2,921.

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

There are 39 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 $2,921.

Your search for investment property begins and ends here

Investment Property for Sale in Chesapeake Beach, MD

8229 BAYSIDE Road

CHESAPEAKE BEACH, MD

4 beds | 4 baths | 2,700 sq.ft.

$777,000

Airbnb cash on cash: 1.24%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $2994

Traditional Rental Income: $3385

Airbnb ROI: 1.24%

Traditional ROI: 2.73%

4011 27TH Street

CHESAPEAKE BEACH, MD

5 beds | 4 baths | 3,100 sq.ft.

$1,300,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.69%

Airbnb Rental Income: $null

Traditional Rental Income: $4050

Airbnb ROI: N/A

Traditional ROI: 1.69%

2425 HARRISON Court

CHESAPEAKE BEACH, MD

4 beds | 3 baths | 3,570 sq.ft.

$679,990

Airbnb cash on cash: 1.57%

Traditional cash on cash: 2.3%

Airbnb Rental Income: $2994

Traditional Rental Income: $2765

Airbnb ROI: 1.57%

Traditional ROI: 2.3%

2310 FOREST RIDGE Terrace #6

CHESAPEAKE BEACH, MD

3 beds | 3 baths | 2,300 sq.ft.

$367,500

Airbnb cash on cash: 1.4%

Traditional cash on cash: 6.53%

Airbnb Rental Income: $2321

Traditional Rental Income: $3514

Airbnb ROI: 1.4%

Traditional ROI: 6.53%

7902 DELORES Court

CHESAPEAKE BEACH, MD

4 beds | 4 baths | 2,688 sq.ft.

$499,990

Airbnb cash on cash: 2.73%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $2994

Traditional Rental Income: $2643

Airbnb ROI: 2.73%

Traditional ROI: 3.45%

6114 2ND Street

CHESAPEAKE BEACH, MD

3 beds | 2 baths | 1,716 sq.ft.

$410,000

Airbnb cash on cash: 3.13%

Traditional cash on cash: 4.07%

Airbnb Rental Income: $2672

Traditional Rental Income: $2398

Airbnb ROI: 3.13%

Traditional ROI: 4.07%

3384 CANNONCADE Court

CHESAPEAKE BEACH, MD

5 beds | 4 baths | 4,422 sq.ft.

$687,500

Airbnb cash on cash: N/A

Traditional cash on cash: 2.89%

Airbnb Rental Income: $null

Traditional Rental Income: $3277

Airbnb ROI: N/A

Traditional ROI: 2.89%

2243 IVY Lane #8

CHESAPEAKE BEACH, MD

3 beds | 3 baths | 2,641 sq.ft.

$375,000

Airbnb cash on cash: 1.35%

Traditional cash on cash: 3.1%

Airbnb Rental Income: $2321

Traditional Rental Income: $2362

Airbnb ROI: 1.35%