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: 1.24% Traditional cash on cash: 2.73% Airbnb Rental Income: $2994 Traditional Rental Income: $3385 Airbnb ROI: 1.24% Traditional ROI: 2.73%
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: -1.43% Traditional cash on cash: 1.25% Airbnb Rental Income: $516 Traditional Rental Income: $1491 Airbnb ROI: -1.43% 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.	$1,300,000	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%
3693 Brookeside Dr CHESAPEAKE BEACH, MD Well maintained Colonial home on corner lot w/front porch and a spacious two car garage; ...	5 beds \| 3 baths \| 2,600 sq.ft.	$539,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.46% Airbnb Rental Income: $null Traditional Rental Income: $3163 Airbnb ROI: N/A Traditional ROI: 4.46%
2425 Harrison Ct CHESAPEAKE BEACH, MD ASSUMABLE 2.25% VA LOAN AVAILABLE (Qualified Buyers - Inquire for Details) Welcome to one ...	4 beds \| 2 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 Ter #6 CHESAPEAKE BEACH, MD Enjoy coastal living in this spacious upper-level penthouse-style condo in the heart of Ch...	3 beds \| 2 baths \| 2,300 sq.ft.	$375,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 6.38% Airbnb Rental Income: $2321 Traditional Rental Income: $3514 Airbnb ROI: 1.35% Traditional ROI: 6.38%
8499 Saint Andrews Dr CHESAPEAKE BEACH, MD Beautifully customized home featuring a stunning kitchen with abundant custom cabinetry, s...	4 beds \| 3 baths \| 2,913 sq.ft.	$605,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 6.83% Airbnb Rental Income: $2994 Traditional Rental Income: $5065 Airbnb ROI: 1.94% Traditional ROI: 6.83%
6114 2nd St 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: 2.37% Traditional cash on cash: 4.07% Airbnb Rental Income: $2321 Traditional Rental Income: $2398 Airbnb ROI: 2.37% Traditional ROI: 4.07%
3384 Cannoncade Ct CHESAPEAKE BEACH, MD Located in the desirable Chesapeake Village community, this beautiful Colonial-style home ...	5 beds \| 3 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 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: 1.35% Traditional cash on cash: 3.1% Airbnb Rental Income: $2321 Traditional Rental Income: $2362 Airbnb ROI: 1.35% Traditional ROI: 3.1%
6122 6th St 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 Rd 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 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: 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 St 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 St 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%
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: -0.39% Traditional cash on cash: 4.6% Airbnb Rental Income: $516 Traditional Rental Income: $680 Airbnb ROI: -0.39% 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.	$149,999	Airbnb cash on cash: -1.37% Traditional cash on cash: 3.59% Airbnb Rental Income: $516 Traditional Rental Income: $952 Airbnb ROI: -1.37% Traditional ROI: 3.59%
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: 0.61% Traditional cash on cash: 8.58% Airbnb Rental Income: $516 Traditional Rental Income: $684 Airbnb ROI: 0.61% 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: 2.22% 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 Dr CHESAPEAKE BEACH, MD Nestled along the tranquil shores of Chesapeake Beach, this stunning four-bedroom, four-an...	4 beds \| 4 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 Dr CHESAPEAKE BEACH, MD Experience an elevated waterfront lifestyle in the coveted Windward Key community, ideally...	4 beds \| 4 baths \| 2,876 sq.ft.	$849,900	Airbnb cash on cash: 0.42% Traditional cash on cash: 3.48% Airbnb Rental Income: $2994 Traditional Rental Income: $4727 Airbnb ROI: 0.42% Traditional ROI: 3.48%
5130 Rosemary Dr CHESAPEAKE BEACH, MD 5130 Rosemary Dr, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	2 beds \| 1 baths \| 828 sq.ft.	$369,950	Airbnb cash on cash: 1.23% Traditional cash on cash: 1.54% Airbnb Rental Income: $1744 Traditional Rental Income: $1372 Airbnb ROI: 1.23% Traditional ROI: 1.54%
Lot 30 A, Block 6, 18th St CHESAPEAKE BEACH, MD Lot 30 A, Block 6, 18th St, CHESAPEAKE BEACH, MD 20732 \| Other	N/A beds \| N/A baths \| N/A	$199,000	Airbnb cash on cash: -1.29% Traditional cash on cash: 1.53% Airbnb Rental Income: $516 Traditional Rental Income: $774 Airbnb ROI: -1.29% Traditional ROI: 1.53%
Lot 22R Block 7, 18th St CHESAPEAKE BEACH, MD Lot 22R Block 7, 18th St, CHESAPEAKE BEACH, MD 20732 \| Other	N/A beds \| N/A baths \| N/A	$99,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 5.02% Airbnb Rental Income: $516 Traditional Rental Income: $776 Airbnb ROI: -0.53% Traditional ROI: 5.02%
Lot 22R Block 8, 18th St CHESAPEAKE BEACH, MD Lot 22R Block 8, 18th St, CHESAPEAKE BEACH, MD 20732 \| Other	N/A beds \| N/A baths \| N/A	$179,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 1.92% Airbnb Rental Income: $516 Traditional Rental Income: $774 Airbnb ROI: -1.21% Traditional ROI: 1.92%
8076 Windward Key Dr CHESAPEAKE BEACH, MD COASTAL LUXURY MEETS EVERYDAY VACATION LIVING in Windward Key on the Chesapeake Bay. Exper...	4 beds \| 4 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%
3640 Estelle Ct CHESAPEAKE BEACH, MD 3640 Estelle Ct, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	5 beds \| 4 baths \| 6,659 sq.ft.	$1,099,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.93% Airbnb Rental Income: $null Traditional Rental Income: $3223 Airbnb ROI: N/A Traditional ROI: 0.93%
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	$500,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 3.14% Airbnb Rental Income: $2321 Traditional Rental Income: $2447 Airbnb ROI: 1.64% Traditional ROI: 3.14%
8048 Windward Key Dr CHESAPEAKE BEACH, MD Discover coastal living at its finest at 8048 Windward Key Dr, Chesapeake Beach! This "as-...	3 beds \| 4 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%
3570 Ponds Wood Dr CHESAPEAKE BEACH, MD Welcome to this beautifully maintained 5-bedroom, 3.5-bath home situated on 3 private acre...	5 beds \| 3 baths \| 3,364 sq.ft.	$589,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.83% Airbnb Rental Income: $null Traditional Rental Income: $3752 Airbnb ROI: N/A Traditional ROI: 4.83%
3535 Cox Rd CHESAPEAKE BEACH, MD 3535 Cox Rd, CHESAPEAKE BEACH, MD 20732 \| Other	N/A beds \| N/A baths \| N/A	$121,250	Airbnb cash on cash: -0.8% Traditional cash on cash: 3.88% Airbnb Rental Income: $516 Traditional Rental Income: $788 Airbnb ROI: -0.8% Traditional ROI: 3.88%
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 \| 869 sq.ft.	$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%

Real Estate investment in Chesapeake-beach, MD

There are 53 properties for sale in the city of Chesapeake Beach . The median list price in Chesapeake Beach is $469,757 and the average price per square foot is $201. In June 2026, the average monthly cash on cash return in Chesapeake Beach is 4.00%. The average monthly rental income in Chesapeake Beach is $2,759.

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

There are 53 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 $2,759.

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: 1.24%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $2994

Traditional Rental Income: $3385

Airbnb ROI: 1.24%

Traditional ROI: 2.73%

5209 Larchmont Dr

CHESAPEAKE BEACH, MD

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

$499,000

Airbnb cash on cash: -1.43%

Traditional cash on cash: 1.25%

Airbnb Rental Income: $516

Traditional Rental Income: $1491

Airbnb ROI: -1.43%

Traditional ROI: 1.25%

4011 27th St

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%

3693 Brookeside Dr

CHESAPEAKE BEACH, MD

5 beds | 3 baths | 2,600 sq.ft.

$539,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.46%

Airbnb Rental Income: $null

Traditional Rental Income: $3163

Airbnb ROI: N/A

Traditional ROI: 4.46%

2425 Harrison Ct

CHESAPEAKE BEACH, MD

4 beds | 2 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 Ter #6

CHESAPEAKE BEACH, MD

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

$375,000

Airbnb cash on cash: 1.35%

Traditional cash on cash: 6.38%

Airbnb Rental Income: $2321

Traditional Rental Income: $3514

Airbnb ROI: 1.35%

Traditional ROI: 6.38%

8499 Saint Andrews Dr

CHESAPEAKE BEACH, MD

4 beds | 3 baths | 2,913 sq.ft.

$605,000

Airbnb cash on cash: 1.94%

Traditional cash on cash: 6.83%

Airbnb Rental Income: $2994

Traditional Rental Income: $5065

Airbnb ROI: 1.94%

Traditional ROI: 6.83%

6114 2nd St

CHESAPEAKE BEACH, MD

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

$410,000

Airbnb cash on cash: 2.37%

Traditional cash on cash: 4.07%

Airbnb Rental Income: $2321

Traditional Rental Income: $2398

Airbnb ROI: 2.37%