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: 0.37% Traditional cash on cash: 2.73% Airbnb Rental Income: $2239 Traditional Rental Income: $3385 Airbnb ROI: 0.37% Traditional ROI: 2.73%
3392 SILVERTON Lane CHESAPEAKE BEACH, MD Beautifully updated 3-bedroom, 2.5-bath townhouse located in the heart of Chesapeake Beach...	3 beds \| 3 baths \| 1,480 sq.ft.	$380,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 4.46% Airbnb Rental Income: $1798 Traditional Rental Income: $2450 Airbnb ROI: 1.26% Traditional ROI: 4.46%
8499 SAINT ANDREWS Drive CHESAPEAKE BEACH, MD Beautifully customized home featuring a stunning kitchen with abundant custom cabinetry, s...	4 beds \| 5 baths \| 3,616 sq.ft.	$625,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 6.58% Airbnb Rental Income: $2239 Traditional Rental Income: $5065 Airbnb ROI: 0.77% Traditional ROI: 6.58%
8329 BAYSIDE RD CHESAPEAKE BEACH, MD **CHESAPEAKE BAY VIEWS* Welcome to this charming 2-bedroom, 1-bath bungalow nestled in...	2 beds \| 1 baths \| N/A	$349,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 2.25% Airbnb Rental Income: $1402 Traditional Rental Income: $1402 Airbnb ROI: 0.96% Traditional ROI: 2.25%
3741 PINEWOOD Court CHESAPEAKE BEACH, MD For those seeking privacy and tranquility, this residence presents an ideal opportunity. M...	4 beds \| 4 baths \| 2,613 sq.ft.	$690,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 2.88% Airbnb Rental Income: $2239 Traditional Rental Income: $3068 Airbnb ROI: 0.72% Traditional ROI: 2.88%
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: 0.98% Traditional cash on cash: 3.64% Airbnb Rental Income: $2239 Traditional Rental Income: $3107 Airbnb ROI: 0.98% Traditional ROI: 3.64%
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.	$349,966	Airbnb cash on cash: 1.95% Traditional cash on cash: 3.78% Airbnb Rental Income: $1798 Traditional Rental Income: $1912 Airbnb ROI: 1.95% Traditional ROI: 3.78%
3907 16TH Street 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%
6572 12TH Street CHESAPEAKE BEACH, MD This 5-bedroom, 3-bathroom home is ready for new owners! Located on a quiet cul-de-sac wit...	5 beds \| 3 baths \| 1,868 sq.ft.	$413,700	Airbnb cash on cash: N/A Traditional cash on cash: 4.27% Airbnb Rental Income: $null Traditional Rental Income: $2513 Airbnb ROI: N/A Traditional ROI: 4.27%
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: 1.26% Traditional cash on cash: 3.21% Airbnb Rental Income: $2239 Traditional Rental Income: $2954 Airbnb ROI: 1.26% Traditional ROI: 3.21%
6309 BROOKEVIEW CT CHESAPEAKE BEACH, MD This beautiful split level home with lots of space, a large back deck, breakfast nook/ din...	4 beds \| 2 baths \| N/A	$449,900	Airbnb cash on cash: 1.86% Traditional cash on cash: 4.26% Airbnb Rental Income: $2239 Traditional Rental Income: $2687 Airbnb ROI: 1.86% Traditional ROI: 4.26%
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: -0.39% Traditional cash on cash: 3.14% Airbnb Rental Income: $2239 Traditional Rental Income: $4475 Airbnb ROI: -0.39% Traditional ROI: 3.14%
8054 WINDWARD KEY DRIVE CHESAPEAKE BEACH, MD Experience an elevated waterfront lifestyle in the coveted Windward Key community, ideally...	4 beds \| 5 baths \| 2,876 sq.ft.	$899,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 3.24% Airbnb Rental Income: $2239 Traditional Rental Income: $4727 Airbnb ROI: -0.41% Traditional ROI: 3.24%
3436 HILL GAIL Drive CHESAPEAKE BEACH, MD *OPEN HOUSE THIS SUNDAY, MAY 17TH FROM 9-11AM* Come check out this beautifully maintai...	5 beds \| 4 baths \| 4,210 sq.ft.	$699,990	Airbnb cash on cash: N/A Traditional cash on cash: 3.85% Airbnb Rental Income: $null Traditional Rental Income: $3900 Airbnb ROI: N/A Traditional ROI: 3.85%
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.	$824,900	Airbnb cash on cash: -0.19% Traditional cash on cash: 4.05% Airbnb Rental Income: $2239 Traditional Rental Income: $4933 Airbnb ROI: -0.19% Traditional ROI: 4.05%
2183 IVY Lane #4 CHESAPEAKE BEACH, MD Welcome to 2183 Ivy Lane in Chesapeake Beach, MD, where comfort, convenience, and low-main...	3 beds \| 3 baths \| 1,650 sq.ft.	$350,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 5.12% Airbnb Rental Income: $1798 Traditional Rental Income: $2931 Airbnb ROI: 0.19% Traditional ROI: 5.12%
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	$479,900	Airbnb cash on cash: 0.78% Traditional cash on cash: 3.31% Airbnb Rental Income: $1798 Traditional Rental Income: $2447 Airbnb ROI: 0.78% Traditional ROI: 3.31%
3456 SILVERTON Lane CHESAPEAKE BEACH, MD Welcome to this beautifully maintained end-unit townhome in the sought-after Bayview Hills...	3 beds \| 3 baths \| 2,478 sq.ft.	$445,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 4.81% Airbnb Rental Income: $1798 Traditional Rental Income: $2984 Airbnb ROI: 0.79% Traditional ROI: 4.81%
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: -0.84% Traditional cash on cash: 3.43% Airbnb Rental Income: $1798 Traditional Rental Income: $4333 Airbnb ROI: -0.84% Traditional ROI: 3.43%
3570 PONDS WOOD Drive CHESAPEAKE BEACH, MD Welcome to this beautifully maintained 5-bedroom, 3.5-bath home situated on 3 private acre...	5 beds \| 4 baths \| 3,364 sq.ft.	$599,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.73% Airbnb Rental Income: $null Traditional Rental Income: $3752 Airbnb ROI: N/A Traditional ROI: 4.73%
4014 BAND SHELL Court CHESAPEAKE BEACH, MD When it comes to WATERFRONT VIEWS you are not going to find much better than this SPECTACU...	3 beds \| 2 baths \| 2,042 sq.ft.	$849,900	Airbnb cash on cash: -0.26% Traditional cash on cash: 1.62% Airbnb Rental Income: $1798 Traditional Rental Income: $2795 Airbnb ROI: -0.26% Traditional ROI: 1.62%
3713 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: -0.42% Traditional cash on cash: 0.34% Airbnb Rental Income: $1402 Traditional Rental Income: $1591 Airbnb ROI: -0.42% Traditional ROI: 0.34%
8125 MOFFAT Run CHESAPEAKE BEACH, MD If you've been searching for a great value in today's market, this could be the opportunit...	4 beds \| 3 baths \| 2,772 sq.ft.	$555,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 4.46% Airbnb Rental Income: $2239 Traditional Rental Income: $3437 Airbnb ROI: 1.07% Traditional ROI: 4.46%
8071 WINDWARD KEY Drive CHESAPEAKE BEACH, MD *OFFER DEADLINE is Monday, May 18, 2026, at 2:00 p.m.* Experience unparalleled WATERFR...	4 beds \| 5 baths \| 2,908 sq.ft.	$949,900	Airbnb cash on cash: -0.01% Traditional cash on cash: 3.39% Airbnb Rental Income: $2239 Traditional Rental Income: $4681 Airbnb ROI: -0.01% Traditional ROI: 3.39%

Real Estate investment in Chesapeake-beach, MD

There are 27 properties for sale in the city of Chesapeake Beach . The median list price in Chesapeake Beach is $599,000 and the average price per square foot is $247. In May 2026, the average monthly cash on cash return in Chesapeake Beach is 4.00%. The average monthly rental income in Chesapeake Beach is $3,068.

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

There are 27 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 $3,068.

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: 0.37%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $2239

Traditional Rental Income: $3385

Airbnb ROI: 0.37%

Traditional ROI: 2.73%

3392 SILVERTON Lane

CHESAPEAKE BEACH, MD

3 beds | 3 baths | 1,480 sq.ft.

$380,000

Airbnb cash on cash: 1.26%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $1798

Traditional Rental Income: $2450

Airbnb ROI: 1.26%

Traditional ROI: 4.46%

8499 SAINT ANDREWS Drive

CHESAPEAKE BEACH, MD

4 beds | 5 baths | 3,616 sq.ft.

$625,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 6.58%

Airbnb Rental Income: $2239

Traditional Rental Income: $5065

Airbnb ROI: 0.77%

Traditional ROI: 6.58%

8329 BAYSIDE RD

CHESAPEAKE BEACH, MD

2 beds | 1 baths | N/A

$349,000

Airbnb cash on cash: 0.96%

Traditional cash on cash: 2.25%

Airbnb Rental Income: $1402

Traditional Rental Income: $1402

Airbnb ROI: 0.96%

Traditional ROI: 2.25%

3741 PINEWOOD Court

CHESAPEAKE BEACH, MD

4 beds | 4 baths | 2,613 sq.ft.

$690,000

Airbnb cash on cash: 0.72%

Traditional cash on cash: 2.88%

Airbnb Rental Income: $2239

Traditional Rental Income: $3068

Airbnb ROI: 0.72%

Traditional ROI: 2.88%

8236 BAYSIDE Road

CHESAPEAKE BEACH, MD

4 beds | 2 baths | 2,857 sq.ft.

$575,000

Airbnb cash on cash: 0.98%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $2239

Traditional Rental Income: $3107

Airbnb ROI: 0.98%

Traditional ROI: 3.64%

6130 4TH Street

CHESAPEAKE BEACH, MD

3 beds | 1 baths | 960 sq.ft.

$349,966

Airbnb cash on cash: 1.95%

Traditional cash on cash: 3.78%

Airbnb Rental Income: $1798

Traditional Rental Income: $1912

Airbnb ROI: 1.95%

Traditional ROI: 3.78%

3907 16TH Street

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