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 Rd CHESAPEAKE BEACH, MD Back on the market due to shaky financing! Inspected and READY! Improved price too! Welcom...	4 beds \| 3 baths \| 2,700 sq.ft.	$777,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 2.73% Airbnb Rental Income: $3269 Traditional Rental Income: $3385 Airbnb ROI: 1.55% Traditional ROI: 2.73%
3955 Breezy Point Rd CHESAPEAKE BEACH, MD *Offer in hand. Please Submit all offers before 10am Wednesday December 6* If you are ...	4 beds \| 2 baths \| 2,464 sq.ft.	$599,900	Airbnb cash on cash: 2.54% Traditional cash on cash: 3.7% Airbnb Rental Income: $3269 Traditional Rental Income: $3189 Airbnb ROI: 2.54% Traditional ROI: 3.7%
5209 Larchmont Dr CHESAPEAKE BEACH, MD Rare waterfront/cliff front lot with wide open view of the Bay. Value in the land, there ...	N/A beds \| N/A baths \| N/A	$499,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 1.25% Airbnb Rental Income: $708 Traditional Rental Income: $1491 Airbnb ROI: -1.09% Traditional ROI: 1.25%
4011 27th St 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.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.92% Airbnb Rental Income: $null Traditional Rental Income: $4050 Airbnb ROI: N/A Traditional ROI: 1.92%
8501 Bayside Rd #606 CHESAPEAKE BEACH, MD Experience life on the Chesapeake Bay! This beautiful condo has stunning views from the M...	2 beds \| 2 baths \| 979 sq.ft.	$469,900	Airbnb cash on cash: 0.65% Traditional cash on cash: 1.51% Airbnb Rental Income: $2511 Traditional Rental Income: $2283 Airbnb ROI: 0.65% Traditional ROI: 1.51%
7436 C St CHESAPEAKE BEACH, MD Vacation year round in Chesapeake Beach in this beautiful cottage by the Bay! Dust off you...	3 beds \| 2 baths \| 1,354 sq.ft.	$419,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 3.71% Airbnb Rental Income: $2672 Traditional Rental Income: $2179 Airbnb ROI: 3.35% Traditional ROI: 3.71%
8400 F St CHESAPEAKE BEACH, MD This contemporary rancher marries rustic and contemporary design. You'll immediately fall ...	3 beds \| 2 baths \| 1,052 sq.ft.	$435,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 3.91% Airbnb Rental Income: $2672 Traditional Rental Income: $2298 Airbnb ROI: 3.27% Traditional ROI: 3.91%
2425 Harrison Ct CHESAPEAKE BEACH, MD ASSUMABLE 2.25% VA LOAN AVAILABLE (Qualified Buyers - Inquire for Details) Price Reduced a...	4 beds \| 2 baths \| 3,570 sq.ft.	$659,900	Airbnb cash on cash: 2.02% Traditional cash on cash: 2.4% Airbnb Rental Income: $3269 Traditional Rental Income: $2765 Airbnb ROI: 2.02% Traditional ROI: 2.4%
3804 16th St CHESAPEAKE BEACH, MD Beautifully tucked away on a private dead end road conveniently located just across the st...	4 beds \| 2 baths \| 2,176 sq.ft.	$585,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 2.71% Airbnb Rental Income: $3269 Traditional Rental Income: $2411 Airbnb ROI: 2.94% Traditional ROI: 2.71%
8256 D St CHESAPEAKE BEACH, MD Wonderful rambler located just 2 blocks from the Chesapeake Bay. View of the bay at front ...	2 beds \| 2 baths \| 900 sq.ft.	$380,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 2.96% Airbnb Rental Income: $2511 Traditional Rental Income: $1701 Airbnb ROI: 3.53% Traditional ROI: 2.96%
2336 Forest Ridge Ter #10 CHESAPEAKE BEACH, MD Enjoy the Chesapeake Beach lifestyle in this 2,600 sf penthouse condo in Northern Calvert!...	3 beds \| 2 baths \| 2,600 sq.ft.	$365,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 3.51% Airbnb Rental Income: $2672 Traditional Rental Income: $2426 Airbnb ROI: 2.38% Traditional ROI: 3.51%
7902 Delores Ct CHESAPEAKE BEACH, MD Fantastic opportunity to own this beautifully maintained END UNIT townhome situated on arg...	4 beds \| 3 baths \| 2,688 sq.ft.	$449,990	Airbnb cash on cash: 3.66% Traditional cash on cash: 4.65% Airbnb Rental Income: $3269 Traditional Rental Income: $2951 Airbnb ROI: 3.66% Traditional ROI: 4.65%
8541 Saint Andrews Dr CHESAPEAKE BEACH, MD Just Painted throughout * Good sized Rooms * Lots of storage and ADDITIONAL 2 car OVERSIZE...	4 beds \| 3 baths \| 2,530 sq.ft.	$590,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 3.73% Airbnb Rental Income: $3269 Traditional Rental Income: $3009 Airbnb ROI: 2.87% Traditional ROI: 3.73%
8418 Clear Spring Dr #1 CHESAPEAKE BEACH, MD Watch the sunlight SHINE through this end unit townhome in Richfield Station! 3 fully fini...	4 beds \| 3 baths \| 1,876 sq.ft.	$400,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 3.9% Airbnb Rental Income: $3269 Traditional Rental Income: $2517 Airbnb ROI: 3.95% Traditional ROI: 3.9%
7880 Ivy Ter #3 CHESAPEAKE BEACH, MD BEAUTIFULLY UPDATED IN RICHFIELD STATION!! Welcome to this beautifully updated 4-bedroom, ...	4 beds \| 3 baths \| 2,414 sq.ft.	$399,900	Airbnb cash on cash: 3.96% Traditional cash on cash: 4.46% Airbnb Rental Income: $3269 Traditional Rental Income: $2720 Airbnb ROI: 3.96% Traditional ROI: 4.46%
3611 Karen Dr CHESAPEAKE BEACH, MD This is your chance, imagine coming home to this gorgeous home located in the desired Lake...	4 beds \| 2 baths \| 2,706 sq.ft.	$639,900	Airbnb cash on cash: 2.36% Traditional cash on cash: 3.62% Airbnb Rental Income: $3269 Traditional Rental Income: $3293 Airbnb ROI: 2.36% Traditional ROI: 3.62%
5233 Breezy Point Rd CHESAPEAKE BEACH, MD Want views of the Chesapeake Bay, WALK to the BEACH and dock your boat!?! Here it is....A...	2 beds \| 1 baths \| 752 sq.ft.	$380,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 2.32% Airbnb Rental Income: $2511 Traditional Rental Income: $1437 Airbnb ROI: 3.63% Traditional ROI: 2.32%
2233 Ivy Ln #3 CHESAPEAKE BEACH, MD Welcome home to this gorgeous ground level entry condo located in Richfield Station. Open...	2 beds \| 2 baths \| 1,658 sq.ft.	$362,500	Airbnb cash on cash: 2.11% Traditional cash on cash: 2.31% Airbnb Rental Income: $2511 Traditional Rental Income: $1972 Airbnb ROI: 2.11% Traditional ROI: 2.31%
3384 Cannoncade Ct CHESAPEAKE BEACH, MD Located in the desirable Chesapeake Village community, this beautiful Colonial-style home ...	4 beds \| 3 baths \| 4,422 sq.ft.	$649,500	Airbnb cash on cash: 1.9% Traditional cash on cash: 3.12% Airbnb Rental Income: $3269 Traditional Rental Income: $3277 Airbnb ROI: 1.9% Traditional ROI: 3.12%
2243 Ivy Ln #8 CHESAPEAKE BEACH, MD NEW PRICE to Sell! Welcome to 2,600+ sq. ft. of comfortable living in Richfield Station. S...	3 beds \| 2 baths \| 2,641 sq.ft.	$375,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 3.1% Airbnb Rental Income: $2672 Traditional Rental Income: $2362 Airbnb ROI: 2.18% Traditional ROI: 3.1%
2811 Glasgow Way CHESAPEAKE BEACH, MD Spacious and private 1.28-acre cul-de-sac lot in the highly sought-after Highlands communi...	3 beds \| 2 baths \| 1,716 sq.ft.	$465,000	Airbnb cash on cash: 2.62% Traditional cash on cash: 3.28% Airbnb Rental Income: $2672 Traditional Rental Income: $2329 Airbnb ROI: 2.62% Traditional ROI: 3.28%
2221 Ivy Ln #G-9 CHESAPEAKE BEACH, MD Discover the epitome of Chesapeake Beach living at this captivating property nestled on Iv...	3 beds \| 2 baths \| 1,600 sq.ft.	$359,900	Airbnb cash on cash: 2.52% Traditional cash on cash: 2.35% Airbnb Rental Income: $2672 Traditional Rental Income: $1979 Airbnb ROI: 2.52% Traditional ROI: 2.35%
3932 Summer City Blvd CHESAPEAKE BEACH, MD REDUCED $5000!!! Bayview, Bayview, Bayview and the seller will contribute $10,000 towards...	3 beds \| 3 baths \| 1,978 sq.ft.	$469,900	Airbnb cash on cash: 2.8% Traditional cash on cash: 4.55% Airbnb Rental Income: $2672 Traditional Rental Income: $2805 Airbnb ROI: 2.8% Traditional ROI: 4.55%
4485 Bristol Dr CHESAPEAKE BEACH, MD Nestled within the Owen Soper Estates community of Chesapeake Beach, this almost-new, 2-ye...	6 beds \| 4 baths \| 6,037 sq.ft.	$1,299,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.15% Airbnb Rental Income: $null Traditional Rental Income: $3472 Airbnb ROI: N/A Traditional ROI: 1.15%
6231 8th St 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: 7.58% Traditional cash on cash: 11.34% Airbnb Rental Income: $2672 Traditional Rental Income: $2716 Airbnb ROI: 7.58% Traditional ROI: 11.34%
3912 17th St CHESAPEAKE BEACH, MD Welcome Home to 3912 17th Street, Chesapeake Beach!! Nestled in the heart of Chesapeake Be...	4 beds \| 3 baths \| 4,386 sq.ft.	$899,900	Airbnb cash on cash: 1.14% Traditional cash on cash: 2.67% Airbnb Rental Income: $3269 Traditional Rental Income: $3813 Airbnb ROI: 1.14% Traditional ROI: 2.67%
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: 1.43% Traditional cash on cash: 4.6% Airbnb Rental Income: $708 Traditional Rental Income: $680 Airbnb ROI: 1.43% Traditional ROI: 4.6%
4685 Camp Roosevelt Dr CHESAPEAKE BEACH, MD 4685 Camp Roosevelt Dr, CHESAPEAKE BEACH, MD 20732 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$136,900	Airbnb cash on cash: -0.08% Traditional cash on cash: 4.11% Airbnb Rental Income: $708 Traditional Rental Income: $952 Airbnb ROI: -0.08% Traditional ROI: 4.11%
4200 Chesapeake Ave CHESAPEAKE BEACH, MD 4200 Chesapeake Ave, CHESAPEAKE BEACH, MD 20732 \| Other	N/A beds \| N/A baths \| N/A	$55,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 8.58% Airbnb Rental Income: $708 Traditional Rental Income: $684 Airbnb ROI: 3.49% Traditional ROI: 8.58%
8314 Bayside Rd CHESAPEAKE BEACH, MD TO BE BUILT HOME in the sought-after Chesapeake Beach community. This exceptional NEW CONS...	4 beds \| 2 baths \| 1,802 sq.ft.	$699,999	Airbnb cash on cash: 2.57% Traditional cash on cash: 3.21% Airbnb Rental Income: $3269 Traditional Rental Income: $2954 Airbnb ROI: 2.57% Traditional ROI: 3.21%
6337 Dory Ct CHESAPEAKE BEACH, MD 6337 Dory Ct, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	6 beds \| 2 baths \| 2,080 sq.ft.	$390,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.22% Airbnb Rental Income: $null Traditional Rental Income: $2397 Airbnb ROI: N/A Traditional ROI: 4.22%

Real Estate investment in Chesapeake-beach, MD

There are 79 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 $204. In August 2026, the average monthly cash on cash return in Chesapeake Beach is 3.00%. The average monthly rental income in Chesapeake Beach is $2,442.

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

There are 79 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 $2,442.

Your search for investment property begins and ends here

Investment Property for Sale in Chesapeake Beach, MD

8229 Bayside Rd

CHESAPEAKE BEACH, MD

4 beds | 3 baths | 2,700 sq.ft.

$777,000

Airbnb cash on cash: 1.55%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $3269

Traditional Rental Income: $3385

Airbnb ROI: 1.55%

Traditional ROI: 2.73%

3955 Breezy Point Rd

CHESAPEAKE BEACH, MD

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

$599,900

Airbnb cash on cash: 2.54%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $3269

Traditional Rental Income: $3189

Airbnb ROI: 2.54%

Traditional ROI: 3.7%

5209 Larchmont Dr

CHESAPEAKE BEACH, MD

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

$499,000

Airbnb cash on cash: -1.09%

Traditional cash on cash: 1.25%

Airbnb Rental Income: $708

Traditional Rental Income: $1491

Airbnb ROI: -1.09%

Traditional ROI: 1.25%

4011 27th St

CHESAPEAKE BEACH, MD

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

$1,200,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.92%

Airbnb Rental Income: $null

Traditional Rental Income: $4050

Airbnb ROI: N/A

Traditional ROI: 1.92%

8501 Bayside Rd #606

CHESAPEAKE BEACH, MD

2 beds | 2 baths | 979 sq.ft.

$469,900

Airbnb cash on cash: 0.65%

Traditional cash on cash: 1.51%

Airbnb Rental Income: $2511

Traditional Rental Income: $2283

Airbnb ROI: 0.65%

Traditional ROI: 1.51%

7436 C St

CHESAPEAKE BEACH, MD

3 beds | 2 baths | 1,354 sq.ft.

$419,000

Airbnb cash on cash: 3.35%

Traditional cash on cash: 3.71%

Airbnb Rental Income: $2672

Traditional Rental Income: $2179

Airbnb ROI: 3.35%

Traditional ROI: 3.71%

8400 F St

CHESAPEAKE BEACH, MD

3 beds | 2 baths | 1,052 sq.ft.

$435,000

Airbnb cash on cash: 3.27%

Traditional cash on cash: 3.91%

Airbnb Rental Income: $2672

Traditional Rental Income: $2298

Airbnb ROI: 3.27%

Traditional ROI: 3.91%

2425 Harrison Ct

CHESAPEAKE BEACH, MD

4 beds | 2 baths | 3,570 sq.ft.

$659,900

Airbnb cash on cash: 2.02%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $3269

Traditional Rental Income: $2765

Airbnb ROI: 2.02%