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.

Woodlawn Investment Property for Sale in Chesapeake Beach, MD

Search for Woodlawn Investment Property for Sale in Chesapeake Beach, Maryland. Browse all of Mashvisor’s Woodlawn Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 30 Woodlawn Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
8501 BAYSIDE Road unit: 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.	$355,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 0.95% Airbnb Rental Income: $1687 Traditional Rental Income: $1472 Airbnb ROI: 0.19% Traditional ROI: 0.95%
3632 BROOKESIDE Drive CHESAPEAKE BEACH, MD Great price for this 4-Level home with a total of 2,855 sf -- including 447 sf of unfinish...	3 beds \| 2 baths \| 2,408 sq.ft.	$449,990	Airbnb cash on cash: 1.27% Traditional cash on cash: 3.67% Airbnb Rental Income: $1999 Traditional Rental Income: $2489 Airbnb ROI: 1.27% Traditional ROI: 3.67%
3609 DORY BROOKS Road CHESAPEAKE BEACH, MD Welcome to 3609 Dory Books Rd! This charming rambler offers 3 bedrooms, kitchen, 1 full an...	4 beds \| 3 baths \| 2,016 sq.ft.	$399,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 6.13% Airbnb Rental Income: $1650 Traditional Rental Income: $3060 Airbnb ROI: 1.12% Traditional ROI: 6.13%
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.	$599,900	Airbnb cash on cash: 0.02% Traditional cash on cash: 3.45% Airbnb Rental Income: $1650 Traditional Rental Income: $3107 Airbnb ROI: 0.02% Traditional ROI: 3.45%
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.	$220,000	Airbnb cash on cash: 3.75% Traditional cash on cash: 9.7% Airbnb Rental Income: $1999 Traditional Rental Income: $2716 Airbnb ROI: 3.75% Traditional ROI: 9.7%
2425 WOODLAND Court CHESAPEAKE BEACH, MD Welcome to Northern Calvert County's Richfield Station! This approximately 3,200 sq ft hom...	4 beds \| 4 baths \| 3,180 sq.ft.	$649,999	Airbnb cash on cash: -0.07% Traditional cash on cash: 4.25% Airbnb Rental Income: $1650 Traditional Rental Income: $3807 Airbnb ROI: -0.07% Traditional ROI: 4.25%
8074 WINDWARD KEY Drive CHESAPEAKE BEACH, MD Welcome to 8074 Windward Key Drive - a stunning four-level coastal townhome offering sweep...	4 beds \| 5 baths \| 3,049 sq.ft.	$850,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 3.71% Airbnb Rental Income: $1650 Traditional Rental Income: $4774 Airbnb ROI: -0.82% Traditional ROI: 3.71%
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.	$423,700	Airbnb cash on cash: N/A Traditional cash on cash: 4.15% Airbnb Rental Income: $null Traditional Rental Income: $2513 Airbnb ROI: N/A Traditional ROI: 4.15%
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: 0.51% Traditional cash on cash: 3.21% Airbnb Rental Income: $1650 Traditional Rental Income: $2954 Airbnb ROI: 0.51% Traditional ROI: 3.21%
3617 30TH Street CHESAPEAKE BEACH, MD NEW ROOF INSTALLED!! NEW EXTERIOR PAINT!! This well-maintained home offers bright, open li...	4 beds \| 2 baths \| 1,850 sq.ft.	$439,900	Airbnb cash on cash: 0.83% Traditional cash on cash: 5.99% Airbnb Rental Income: $1650 Traditional Rental Income: $3312 Airbnb ROI: 0.83% Traditional ROI: 5.99%
3800 28TH Street CHESAPEAKE BEACH, MD Step into the charm and potential of this Chesapeake Beach gem! This 3-bedroom, 1.5-bath h...	3 beds \| 2 baths \| 1,657 sq.ft.	$324,900	Airbnb cash on cash: 2.44% Traditional cash on cash: 5.2% Airbnb Rental Income: $1999 Traditional Rental Income: $2320 Airbnb ROI: 2.44% Traditional ROI: 5.2%
8223 C Street CHESAPEAKE BEACH, MD Imagine waking up to the sound of gentle waves and stepping outside with your morning coff...	4 beds \| 2 baths \| 1,600 sq.ft.	$725,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 2.12% Airbnb Rental Income: $1650 Traditional Rental Income: $2782 Airbnb ROI: -0.24% Traditional ROI: 2.12%
7005 NAPA Drive CHESAPEAKE BEACH, MD Welcome to 7005 Napa Drive in Chesapeake Beach, Maryland, a beautiful and modern 4-bedroom...	4 beds \| 4 baths \| 4,018 sq.ft.	$780,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 2.42% Airbnb Rental Income: $1650 Traditional Rental Income: $3312 Airbnb ROI: -0.5% Traditional ROI: 2.42%
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: 0.7% Traditional cash on cash: 5.74% Airbnb Rental Income: $1650 Traditional Rental Income: $3312 Airbnb ROI: 0.7% Traditional ROI: 5.74%
8501 BAYSIDE Road unit: 605 CHESAPEAKE BEACH, MD Stunning Chesapeake Bay panoramic water views from this luxury condominium. Features two b...	2 beds \| 2 baths \| 984 sq.ft.	$450,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 0.7% Airbnb Rental Income: $2167 Traditional Rental Income: $1886 Airbnb ROI: 0.07% Traditional ROI: 0.7%
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.	$869,900	Airbnb cash on cash: -1.01% Traditional cash on cash: 1.61% Airbnb Rental Income: $1650 Traditional Rental Income: $3312 Airbnb ROI: -1.01% Traditional ROI: 1.61%
3238 RECTOR LOOKOUT CHESAPEAKE BEACH, MD Welcome to 3238 Rector Lookout in the sought-after community of Chesapeake Beach, MD 20732...	3 beds \| 4 baths \| 3,058 sq.ft.	$630,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 1.89% Airbnb Rental Income: $1999 Traditional Rental Income: $2295 Airbnb ROI: 0.5% Traditional ROI: 1.89%
3221 SMITHS RETREAT CHESAPEAKE BEACH, MD Tucked away on a quiet cul-de-sac in sought-after Chesapeake Beach, this home offers a com...	4 beds \| 4 baths \| 3,300 sq.ft.	$735,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 2.87% Airbnb Rental Income: $1650 Traditional Rental Income: $3312 Airbnb ROI: -0.24% Traditional ROI: 2.87%
3339 CANNONCADE Court unit: 29 CHESAPEAKE BEACH, MD Welcome to 3339 Cannoncade Ct., a beautifully updated multigenerational Colonial home tuck...	5 beds \| 4 baths \| 4,660 sq.ft.	$730,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.97% Airbnb Rental Income: $null Traditional Rental Income: $4148 Airbnb ROI: N/A Traditional ROI: 3.97%

Your search for investment property begins and ends here

Woodlawn Investment Property for Sale in Chesapeake Beach, MD

8501 BAYSIDE Road unit: 702

CHESAPEAKE BEACH, MD

1 beds | 2 baths | 862 sq.ft.

$355,000

Airbnb cash on cash: 0.19%

Traditional cash on cash: 0.95%

Airbnb Rental Income: $1687

Traditional Rental Income: $1472

Airbnb ROI: 0.19%

Traditional ROI: 0.95%

3632 BROOKESIDE Drive

CHESAPEAKE BEACH, MD

3 beds | 2 baths | 2,408 sq.ft.

$449,990

Airbnb cash on cash: 1.27%

Traditional cash on cash: 3.67%

Airbnb Rental Income: $1999

Traditional Rental Income: $2489

Airbnb ROI: 1.27%

Traditional ROI: 3.67%

3609 DORY BROOKS Road

CHESAPEAKE BEACH, MD

4 beds | 3 baths | 2,016 sq.ft.

$399,000

Airbnb cash on cash: 1.12%

Traditional cash on cash: 6.13%

Airbnb Rental Income: $1650

Traditional Rental Income: $3060

Airbnb ROI: 1.12%

Traditional ROI: 6.13%

8236 BAYSIDE Road

CHESAPEAKE BEACH, MD

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

$599,900

Airbnb cash on cash: 0.02%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $1650

Traditional Rental Income: $3107

Airbnb ROI: 0.02%

Traditional ROI: 3.45%

6231 8TH Street

CHESAPEAKE BEACH, MD

3 beds | 2 baths | 2,597 sq.ft.

$220,000

Airbnb cash on cash: 3.75%

Traditional cash on cash: 9.7%

Airbnb Rental Income: $1999

Traditional Rental Income: $2716

Airbnb ROI: 3.75%

Traditional ROI: 9.7%

2425 WOODLAND Court

CHESAPEAKE BEACH, MD

4 beds | 4 baths | 3,180 sq.ft.

$649,999

Airbnb cash on cash: -0.07%

Traditional cash on cash: 4.25%

Airbnb Rental Income: $1650

Traditional Rental Income: $3807

Airbnb ROI: -0.07%

Traditional ROI: 4.25%

8074 WINDWARD KEY Drive

CHESAPEAKE BEACH, MD

4 beds | 5 baths | 3,049 sq.ft.

$850,000

Airbnb cash on cash: -0.82%

Traditional cash on cash: 3.71%

Airbnb Rental Income: $1650

Traditional Rental Income: $4774

Airbnb ROI: -0.82%

Traditional ROI: 3.71%

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