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: -0.27% Traditional cash on cash: 2.73% Airbnb Rental Income: $1688 Traditional Rental Income: $3385 Airbnb ROI: -0.27% 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: -1.45% Traditional cash on cash: 1.25% Airbnb Rental Income: $507 Traditional Rental Income: $1491 Airbnb ROI: -1.45% Traditional ROI: 1.25%
8501 BAYSIDE Road #702 CHESAPEAKE BEACH, MD Horizons On The Bay is a gated seaside community, with too many amenities to list! Relax a...	1 beds \| 2 baths \| 862 sq.ft.	$349,000	Airbnb cash on cash: -1.87% Traditional cash on cash: 2.35% Airbnb Rental Income: $1140 Traditional Rental Income: $2144 Airbnb ROI: -1.87% Traditional ROI: 2.35%
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: -0.01% Traditional cash on cash: 6.58% Airbnb Rental Income: $1688 Traditional Rental Income: $5065 Airbnb ROI: -0.01% 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: 0.91% Traditional cash on cash: 2.25% Airbnb Rental Income: $1381 Traditional Rental Income: $1402 Airbnb ROI: 0.91% Traditional ROI: 2.25%
3908 Old Bayside Rd CHESAPEAKE BEACH, MD This welcoming home is located in a sought-after neighborhood in Chesapeake Beach! Itâs...	3 beds \| 1 baths \| 1,164 sq.ft.	$439,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 2.7% Airbnb Rental Income: $1720 Traditional Rental Income: $1852 Airbnb ROI: 1.22% Traditional ROI: 2.7%
3728 CHESAPEAKE BEACH Road E CHESAPEAKE BEACH, MD Don't miss out on this fantastic chance to acquire a delightful 2-bedroom, 1-bath rambler ...	2 beds \| 1 baths \| 1,364 sq.ft.	$260,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 4.55% Airbnb Rental Income: $1381 Traditional Rental Income: $1662 Airbnb ROI: 1.7% Traditional ROI: 4.55%
8236 BAYSIDE Road CHESAPEAKE BEACH, MD Beach living at its best in the heart of Chesapeake Beach! Embrace the coastal lifestyle i...	4 beds \| 2 baths \| 2,857 sq.ft.	$575,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 3.64% Airbnb Rental Income: $1688 Traditional Rental Income: $3107 Airbnb ROI: 0.12% 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.	$349,975	Airbnb cash on cash: 1.75% Traditional cash on cash: 3.78% Airbnb Rental Income: $1720 Traditional Rental Income: $1912 Airbnb ROI: 1.75% 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%
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: -0.47% Traditional cash on cash: 4.6% Airbnb Rental Income: $507 Traditional Rental Income: $680 Airbnb ROI: -0.47% 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: -1.42% Traditional cash on cash: 3.59% Airbnb Rental Income: $507 Traditional Rental Income: $952 Airbnb ROI: -1.42% 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: 0.47% Traditional cash on cash: 8.58% Airbnb Rental Income: $507 Traditional Rental Income: $684 Airbnb ROI: 0.47% Traditional ROI: 8.58%
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: 0.55% Traditional cash on cash: 3.21% Airbnb Rental Income: $1688 Traditional Rental Income: $2954 Airbnb ROI: 0.55% 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: 0.77% Traditional cash on cash: 4.26% Airbnb Rental Income: $1688 Traditional Rental Income: $2687 Airbnb ROI: 0.77% 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: -0.97% Traditional cash on cash: 3.14% Airbnb Rental Income: $1688 Traditional Rental Income: $4475 Airbnb ROI: -0.97% 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: -0.95% Traditional cash on cash: 3.24% Airbnb Rental Income: $1688 Traditional Rental Income: $4727 Airbnb ROI: -0.95% Traditional ROI: 3.24%
5130 Rosemary Dr CHESAPEAKE BEACH, MD 5130 Rosemary Dr, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	2 beds \| 1 baths \| 828 sq.ft.	$374,950	Airbnb cash on cash: 0.32% Traditional cash on cash: 1.49% Airbnb Rental Income: $1381 Traditional Rental Income: $1372 Airbnb ROI: 0.32% Traditional ROI: 1.49%
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: -1.33% Traditional cash on cash: 1.53% Airbnb Rental Income: $507 Traditional Rental Income: $774 Airbnb ROI: -1.33% 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: -0.61% Traditional cash on cash: 5.02% Airbnb Rental Income: $507 Traditional Rental Income: $776 Airbnb ROI: -0.61% 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: -1.25% Traditional cash on cash: 1.92% Airbnb Rental Income: $507 Traditional Rental Income: $774 Airbnb ROI: -1.25% Traditional ROI: 1.92%
3436 HILL GAIL Drive CHESAPEAKE BEACH, MD This beautifully maintained home is located in the highly sought-after Chesapeake Village ...	5 beds \| 4 baths \| 4,210 sq.ft.	$719,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.72% Airbnb Rental Income: $null Traditional Rental Income: $3900 Airbnb ROI: N/A Traditional ROI: 3.72%
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: -0.79% Traditional cash on cash: 4.05% Airbnb Rental Income: $1688 Traditional Rental Income: $4933 Airbnb ROI: -0.79% Traditional ROI: 4.05%
2183 IVY Lane #4 CHESAPEAKE BEACH, MD Welcome to 2183 Ivy Lane in Chesapeake Beach, MD-an exceptional opportunity to own a beaut...	3 beds \| 3 baths \| 1,650 sq.ft.	$350,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 5.12% Airbnb Rental Income: $1720 Traditional Rental Income: $2931 Airbnb ROI: -0.01% Traditional ROI: 5.12%
3640 Estelle Ct CHESAPEAKE BEACH, MD 3640 Estelle Ct, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	5 beds \| 4 baths \| 6,659 sq.ft.	$1,125,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.86% Airbnb Rental Income: $null Traditional Rental Income: $3223 Airbnb ROI: N/A Traditional ROI: 0.86%
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: 0.64% Traditional cash on cash: 3.31% Airbnb Rental Income: $1720 Traditional Rental Income: $2447 Airbnb ROI: 0.64% Traditional ROI: 3.31%

Real Estate investment in Chesapeake-beach, MD

There are 45 properties for sale in the city of Chesapeake Beach . The median list price in Chesapeake Beach is $449,900 and the average price per square foot is $218. 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 $2,709.

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

There are 45 investment properties available for sale in Chesapeake-beach.

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

The ROI for Short-Term is higher than the Long-Term in Chesapeake-beach with average rental income of $1,688.

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: -0.27%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $1688

Traditional Rental Income: $3385

Airbnb ROI: -0.27%

Traditional ROI: 2.73%

5209 Larchmont Dr

CHESAPEAKE BEACH, MD

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

$499,000

Airbnb cash on cash: -1.45%

Traditional cash on cash: 1.25%

Airbnb Rental Income: $507

Traditional Rental Income: $1491

Airbnb ROI: -1.45%

Traditional ROI: 1.25%

8501 BAYSIDE Road #702

CHESAPEAKE BEACH, MD

1 beds | 2 baths | 862 sq.ft.

$349,000

Airbnb cash on cash: -1.87%

Traditional cash on cash: 2.35%

Airbnb Rental Income: $1140

Traditional Rental Income: $2144

Airbnb ROI: -1.87%

Traditional ROI: 2.35%

8499 SAINT ANDREWS Drive

CHESAPEAKE BEACH, MD

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

$625,000

Airbnb cash on cash: -0.01%

Traditional cash on cash: 6.58%

Airbnb Rental Income: $1688

Traditional Rental Income: $5065

Airbnb ROI: -0.01%

Traditional ROI: 6.58%

8329 BAYSIDE RD

CHESAPEAKE BEACH, MD

2 beds | 1 baths | N/A

$349,000

Airbnb cash on cash: 0.91%

Traditional cash on cash: 2.25%

Airbnb Rental Income: $1381

Traditional Rental Income: $1402

Airbnb ROI: 0.91%

Traditional ROI: 2.25%

3908 Old Bayside Rd

CHESAPEAKE BEACH, MD

3 beds | 1 baths | 1,164 sq.ft.

$439,000

Airbnb cash on cash: 1.22%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $1720

Traditional Rental Income: $1852

Airbnb ROI: 1.22%

Traditional ROI: 2.7%

3728 CHESAPEAKE BEACH Road E

CHESAPEAKE BEACH, MD

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

$260,000

Airbnb cash on cash: 1.7%

Traditional cash on cash: 4.55%

Airbnb Rental Income: $1381

Traditional Rental Income: $1662

Airbnb ROI: 1.7%

Traditional ROI: 4.55%

8236 BAYSIDE Road

CHESAPEAKE BEACH, MD

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

$575,000

Airbnb cash on cash: 0.12%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $1688

Traditional Rental Income: $3107

Airbnb ROI: 0.12%