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.

Single Family Homes for Sale in Chesapeake Beach, MD

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

Showing 38 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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.	$565,000	Airbnb cash on cash: 2.13% Traditional cash on cash: 3.99% Airbnb Rental Income: $2877 Traditional Rental Income: $3189 Airbnb ROI: 2.13% Traditional ROI: 3.99%
6230 9th St CHESAPEAKE BEACH, MD If swimming, boating and fishing is your thing....this jewel is just blocks from the beaut...	3 beds \| 2 baths \| 2,512 sq.ft.	$514,900	Airbnb cash on cash: 2.39% Traditional cash on cash: 2.89% Airbnb Rental Income: $2602 Traditional Rental Income: $2222 Airbnb ROI: 2.39% Traditional ROI: 2.89%
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%
8320 Harrison Blvd CHESAPEAKE BEACH, MD RENOVATED FOR NEW OWNERS.Move right into this immaculate home with hardwood floors through...	4 beds \| 2 baths \| 2,676 sq.ft.	$624,900	Airbnb cash on cash: 1.99% Traditional cash on cash: 2.71% Airbnb Rental Income: $2877 Traditional Rental Income: $2628 Airbnb ROI: 1.99% Traditional ROI: 2.71%
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.	$519,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.68% Airbnb Rental Income: $null Traditional Rental Income: $3163 Airbnb ROI: N/A Traditional ROI: 4.68%
2425 Harrison Ct CHESAPEAKE BEACH, MD OPEN HOUSE SATURDAY, SEPTEMBER 5th, 1-3 pm ASSUMABLE 2.25% VA LOAN AVAILABLE (Qualified Bu...	4 beds \| 3 baths \| 3,570 sq.ft.	$634,900	Airbnb cash on cash: 1.59% Traditional cash on cash: 2.53% Airbnb Rental Income: $2877 Traditional Rental Income: $2765 Airbnb ROI: 1.59% Traditional ROI: 2.53%
3905 17th St CHESAPEAKE BEACH, MD Welcome to Chesapeake Beach - Easy one-level living, a huge detached garage, and the laid-...	3 beds \| 1 baths \| 1,164 sq.ft.	$365,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 4.44% Airbnb Rental Income: $2602 Traditional Rental Income: $2199 Airbnb ROI: 3.8% Traditional ROI: 4.44%
2811 Glasgow Way CHESAPEAKE BEACH, MD Recent updates include: New Luxury Vinyl Plank (LVP) Flooring - June 2026; New Hot Water H...	3 beds \| 2 baths \| 1,856 sq.ft.	$459,900	Airbnb cash on cash: 2.52% Traditional cash on cash: 3.33% Airbnb Rental Income: $2602 Traditional Rental Income: $2329 Airbnb ROI: 2.52% Traditional ROI: 3.33%
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.	$459,900	Airbnb cash on cash: 2.75% Traditional cash on cash: 4.66% Airbnb Rental Income: $2602 Traditional Rental Income: $2805 Airbnb ROI: 2.75% Traditional ROI: 4.66%
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.	$1,289,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.17% Airbnb Rental Income: $null Traditional Rental Income: $3472 Airbnb ROI: N/A Traditional ROI: 1.17%
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: 7.26% Traditional cash on cash: 11.34% Airbnb Rental Income: $2602 Traditional Rental Income: $2716 Airbnb ROI: 7.26% Traditional ROI: 11.34%
3912 17th St CHESAPEAKE BEACH, MD Welcome Home to 3912 17th Street, Chesapeake Beach!! THIS HOME IS SO SPACIOUS!!Nestled in ...	4 beds \| 3 baths \| 4,386 sq.ft.	$879,900	Airbnb cash on cash: 0.79% Traditional cash on cash: 2.75% Airbnb Rental Income: $2877 Traditional Rental Income: $3813 Airbnb ROI: 0.79% Traditional ROI: 2.75%
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: 2.07% Traditional cash on cash: 3.21% Airbnb Rental Income: $2877 Traditional Rental Income: $2954 Airbnb ROI: 2.07% 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%
3800 28th St CHESAPEAKE BEACH, MD ***Seller is Offering Closing Costs Assistance***Welcome to coastal living at its fine...	3 beds \| 2 baths \| 1,657 sq.ft.	$539,900	Airbnb cash on cash: 2.08% Traditional cash on cash: 2.76% Airbnb Rental Income: $2602 Traditional Rental Income: $2320 Airbnb ROI: 2.08% Traditional ROI: 2.76%
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.	$799,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 0.45% Airbnb Rental Income: $2901 Traditional Rental Income: $1591 Airbnb ROI: 1.3% Traditional ROI: 0.45%
4010 Beach Dr CHESAPEAKE BEACH, MD 4010 Beach Dr, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	3 beds \| 2 baths \| 2,296 sq.ft.	$515,000	Airbnb cash on cash: 1.79% Traditional cash on cash: 2.39% Airbnb Rental Income: $2602 Traditional Rental Income: $2270 Airbnb ROI: 1.79% Traditional ROI: 2.39%
2630 Richfield Ln CHESAPEAKE BEACH, MD Welcome to 2630 Richfield Lane in Chesapeake Beach! This beautiful 4-bedroom, 2 full bath,...	4 beds \| 2 baths \| 2,276 sq.ft.	$579,900	Airbnb cash on cash: 1.96% Traditional cash on cash: 3.27% Airbnb Rental Income: $2877 Traditional Rental Income: $2915 Airbnb ROI: 1.96% Traditional ROI: 3.27%
3671 Middle Ground Ct CHESAPEAKE BEACH, MD 3671 Middle Ground Ct, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	5 beds \| 3 baths \| 3,819 sq.ft.	$670,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.32% Airbnb Rental Income: $null Traditional Rental Income: $2872 Airbnb ROI: N/A Traditional ROI: 2.32%
3555 Christiana Ct CHESAPEAKE BEACH, MD Looking for true privacy with NO HOA, then look no further to this quaint Colonial nested ...	5 beds \| 3 baths \| 3,837 sq.ft.	$635,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.84% Airbnb Rental Income: $null Traditional Rental Income: $2955 Airbnb ROI: N/A Traditional ROI: 2.84%
6114 4th St CHESAPEAKE BEACH, MD Welcome to your turn-key coastal sanctuary! This 3-bedroom, 2-bathroom home in the heart o...	3 beds \| 2 baths \| 1,876 sq.ft.	$439,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 3.38% Airbnb Rental Income: $2602 Traditional Rental Income: $2199 Airbnb ROI: 2.84% Traditional ROI: 3.38%
4325 Willows Rd CHESAPEAKE BEACH, MD Welcome home to this spacious colonial in the sought-after, water-privileged community of ...	4 beds \| 4 baths \| 3,240 sq.ft.	$574,700	Airbnb cash on cash: 1.93% Traditional cash on cash: 7.07% Airbnb Rental Income: $2877 Traditional Rental Income: $4970 Airbnb ROI: 1.93% Traditional ROI: 7.07%
4215 Calvert Dr CHESAPEAKE BEACH, MD Adorable 3 bd 1 ba in Holiday Beach. Short walk to a private community beach. The Living r...	3 beds \| 1 baths \| 920 sq.ft.	$369,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 3.67% Airbnb Rental Income: $2602 Traditional Rental Income: $1948 Airbnb ROI: 3.76% Traditional ROI: 3.67%
6417 Brookeside Ct CHESAPEAKE BEACH, MD Welcome to 6417 Brookeside Court! This 3-bedroom, 2-bath home offers plenty of space, rece...	3 beds \| 1 baths \| 1,840 sq.ft.	$414,900	Airbnb cash on cash: 2.95% Traditional cash on cash: 2.84% Airbnb Rental Income: $2602 Traditional Rental Income: $1938 Airbnb ROI: 2.95% Traditional ROI: 2.84%
8138 Bayview Hills Dr CHESAPEAKE BEACH, MD 8138 Bayview Hills Dr, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	4 beds \| 3 baths \| 2,368 sq.ft.	$525,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 3.22% Airbnb Rental Income: $2877 Traditional Rental Income: $2733 Airbnb ROI: 2.15% Traditional ROI: 3.22%
3309 Recker Rd CHESAPEAKE BEACH, MD 3309 Recker Rd, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	3 beds \| 2 baths \| 1,856 sq.ft.	$375,000	Airbnb cash on cash: 3.28% Traditional cash on cash: 3.22% Airbnb Rental Income: $2602 Traditional Rental Income: $1960 Airbnb ROI: 3.28% Traditional ROI: 3.22%
8308 Legacy Cir CHESAPEAKE BEACH, MD 8308 Legacy Cir, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	4 beds \| 3 baths \| 3,298 sq.ft.	$715,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 1.77% Airbnb Rental Income: $2877 Traditional Rental Income: $2718 Airbnb ROI: 1.01% Traditional ROI: 1.77%
4884 Ridge Rd CHESAPEAKE BEACH, MD 4884 Ridge Rd, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	3 beds \| 1 baths \| 1,200 sq.ft.	$350,000	Airbnb cash on cash: 3.66% Traditional cash on cash: 2.38% Airbnb Rental Income: $2602 Traditional Rental Income: $1558 Airbnb ROI: 3.66% Traditional ROI: 2.38%
4883 Ridge Rd CHESAPEAKE BEACH, MD 4883 Ridge Rd, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	3 beds \| 3 baths \| 2,425 sq.ft.	$400,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 4.9% Airbnb Rental Income: $2602 Traditional Rental Income: $2710 Airbnb ROI: 2.95% Traditional ROI: 4.9%
4006 Chesapeake Ave CHESAPEAKE BEACH, MD 4006 Chesapeake Ave, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	4 beds \| 3 baths \| 1,785 sq.ft.	$499,000	Airbnb cash on cash: 2.45% Traditional cash on cash: 3.04% Airbnb Rental Income: $2877 Traditional Rental Income: $2483 Airbnb ROI: 2.45% Traditional ROI: 3.04%
7513 I St CHESAPEAKE BEACH, MD 7513 I St, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	3 beds \| 2 baths \| 1,830 sq.ft.	$489,900	Airbnb cash on cash: 2.04% Traditional cash on cash: 2.36% Airbnb Rental Income: $2602 Traditional Rental Income: $2130 Airbnb ROI: 2.04% Traditional ROI: 2.36%
4525 Camp Roosevelt Dr CHESAPEAKE BEACH, MD 4525 Camp Roosevelt Dr, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	5 beds \| 5 baths \| 7,627 sq.ft.	$2,795,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.38% Airbnb Rental Income: $null Traditional Rental Income: $4521 Airbnb ROI: N/A Traditional ROI: -0.38%
8560 St Andrews Dr CHESAPEAKE BEACH, MD 8560 St Andrews Dr, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	3 beds \| 1 baths \| 1,056 sq.ft.	$365,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 2.44% Airbnb Rental Income: $2602 Traditional Rental Income: $1641 Airbnb ROI: 3.42% Traditional ROI: 2.44%
5900 Shirl Ct CHESAPEAKE BEACH, MD 5900 Shirl Ct, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	4 beds \| 3 baths \| 2,851 sq.ft.	$775,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 1.69% Airbnb Rental Income: $2877 Traditional Rental Income: $2829 Airbnb ROI: 0.83% Traditional ROI: 1.69%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chesapeake Beach, MD

3955 Breezy Point Rd

CHESAPEAKE BEACH, MD

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

$565,000

Airbnb cash on cash: 2.13%

Traditional cash on cash: 3.99%

Airbnb Rental Income: $2877

Traditional Rental Income: $3189

Airbnb ROI: 2.13%

Traditional ROI: 3.99%

6230 9th St

CHESAPEAKE BEACH, MD

3 beds | 2 baths | 2,512 sq.ft.

$514,900

Airbnb cash on cash: 2.39%

Traditional cash on cash: 2.89%

Airbnb Rental Income: $2602

Traditional Rental Income: $2222

Airbnb ROI: 2.39%

Traditional ROI: 2.89%

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%

8320 Harrison Blvd

CHESAPEAKE BEACH, MD

4 beds | 2 baths | 2,676 sq.ft.

$624,900

Airbnb cash on cash: 1.99%

Traditional cash on cash: 2.71%

Airbnb Rental Income: $2877

Traditional Rental Income: $2628

Airbnb ROI: 1.99%

Traditional ROI: 2.71%

3693 Brookeside Dr

CHESAPEAKE BEACH, MD

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

$519,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.68%

Airbnb Rental Income: $null

Traditional Rental Income: $3163

Airbnb ROI: N/A

Traditional ROI: 4.68%

2425 Harrison Ct

CHESAPEAKE BEACH, MD

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

$634,900

Airbnb cash on cash: 1.59%

Traditional cash on cash: 2.53%

Airbnb Rental Income: $2877

Traditional Rental Income: $2765

Airbnb ROI: 1.59%

Traditional ROI: 2.53%

3905 17th St

CHESAPEAKE BEACH, MD

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

$365,000

Airbnb cash on cash: 3.8%

Traditional cash on cash: 4.44%

Airbnb Rental Income: $2602

Traditional Rental Income: $2199

Airbnb ROI: 3.8%

Traditional ROI: 4.44%

2811 Glasgow Way

CHESAPEAKE BEACH, MD

3 beds | 2 baths | 1,856 sq.ft.

$459,900

Airbnb cash on cash: 2.52%

Traditional cash on cash: 3.33%

Airbnb Rental Income: $2602

Traditional Rental Income: $2329

Airbnb ROI: 2.52%