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 42 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
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: 1.55% Traditional cash on cash: 2.73% Airbnb Rental Income: $3269 Traditional Rental Income: $3385 Airbnb ROI: 1.55% Traditional ROI: 2.73%
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.	$599,900	Airbnb cash on cash: 2.54% Traditional cash on cash: 3.7% Airbnb Rental Income: $3269 Traditional Rental Income: $3189 Airbnb ROI: 2.54% Traditional ROI: 3.7%
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%
7436 C St CHESAPEAKE BEACH, MD Vacation year round in Chesapeake Beach in this beautiful cottage by the Bay! Dust off you...	3 beds \| 2 baths \| 1,354 sq.ft.	$419,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 3.71% Airbnb Rental Income: $2672 Traditional Rental Income: $2179 Airbnb ROI: 3.35% Traditional ROI: 3.71%
2425 Harrison Ct CHESAPEAKE BEACH, MD ASSUMABLE 2.25% VA LOAN AVAILABLE (Qualified Buyers - Inquire for Details) Price Reduced a...	4 beds \| 2 baths \| 3,570 sq.ft.	$665,000	Airbnb cash on cash: 2% Traditional cash on cash: 2.37% Airbnb Rental Income: $3269 Traditional Rental Income: $2765 Airbnb ROI: 2% Traditional ROI: 2.37%
3804 16th St CHESAPEAKE BEACH, MD Beautifully tucked away on a private dead end road conveniently located just across the st...	4 beds \| 2 baths \| 2,176 sq.ft.	$585,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 2.71% Airbnb Rental Income: $3269 Traditional Rental Income: $2411 Airbnb ROI: 2.94% Traditional ROI: 2.71%
8256 D St CHESAPEAKE BEACH, MD Wonderful rambler located just 2 blocks from the Chesapeake Bay. View of the bay at front ...	2 beds \| 2 baths \| 900 sq.ft.	$380,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 2.96% Airbnb Rental Income: $2511 Traditional Rental Income: $1701 Airbnb ROI: 3.53% Traditional ROI: 2.96%
3611 Karen Dr CHESAPEAKE BEACH, MD This is your chance, imagine coming home to this gorgeous home located in the desired Lake...	4 beds \| 2 baths \| 2,706 sq.ft.	$659,900	Airbnb cash on cash: 2.26% Traditional cash on cash: 3.49% Airbnb Rental Income: $3269 Traditional Rental Income: $3293 Airbnb ROI: 2.26% Traditional ROI: 3.49%
5233 Breezy Point Rd CHESAPEAKE BEACH, MD Want views of the Chesapeake Bay, WALK to the BEACH and dock your boat!?! Here it is....A...	2 beds \| 1 baths \| 752 sq.ft.	$380,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 2.32% Airbnb Rental Income: $2511 Traditional Rental Income: $1437 Airbnb ROI: 3.63% Traditional ROI: 2.32%
3384 Cannoncade Ct CHESAPEAKE BEACH, MD Located in the desirable Chesapeake Village community, this beautiful Colonial-style home ...	4 beds \| 3 baths \| 4,422 sq.ft.	$649,500	Airbnb cash on cash: 1.9% Traditional cash on cash: 3.12% Airbnb Rental Income: $3269 Traditional Rental Income: $3277 Airbnb ROI: 1.9% Traditional ROI: 3.12%
2811 Glasgow Way CHESAPEAKE BEACH, MD Spacious and private 1.28-acre cul-de-sac lot in the highly sought-after Highlands communi...	3 beds \| 2 baths \| 1,716 sq.ft.	$465,000	Airbnb cash on cash: 2.62% Traditional cash on cash: 3.28% Airbnb Rental Income: $2672 Traditional Rental Income: $2329 Airbnb ROI: 2.62% Traditional ROI: 3.28%
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.	$478,900	Airbnb cash on cash: 2.73% Traditional cash on cash: 4.44% Airbnb Rental Income: $2672 Traditional Rental Income: $2805 Airbnb ROI: 2.73% Traditional ROI: 4.44%
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.	$1,299,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.15% Airbnb Rental Income: $null Traditional Rental Income: $3472 Airbnb ROI: N/A Traditional ROI: 1.15%
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.	$275,000	Airbnb cash on cash: 5.14% Traditional cash on cash: 4.74% Airbnb Rental Income: $2511 Traditional Rental Income: $1801 Airbnb ROI: 5.14% Traditional ROI: 4.74%
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: 7.58% Traditional cash on cash: 11.34% Airbnb Rental Income: $2672 Traditional Rental Income: $2716 Airbnb ROI: 7.58% Traditional ROI: 11.34%
3912 17th St CHESAPEAKE BEACH, MD Welcome Home to 3912 17th Street, Chesapeake Beach!! Nestled in the heart of Chesapeake Be...	4 beds \| 3 baths \| 4,386 sq.ft.	$899,901	Airbnb cash on cash: 1.14% Traditional cash on cash: 2.67% Airbnb Rental Income: $3269 Traditional Rental Income: $3813 Airbnb ROI: 1.14% Traditional ROI: 2.67%
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: 2.57% Traditional cash on cash: 3.21% Airbnb Rental Income: $3269 Traditional Rental Income: $2954 Airbnb ROI: 2.57% 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 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.	$579,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 2.5% Airbnb Rental Income: $2672 Traditional Rental Income: $2320 Airbnb ROI: 1.98% Traditional ROI: 2.5%
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: 3.07% Traditional cash on cash: 1.54% Airbnb Rental Income: $2511 Traditional Rental Income: $1372 Airbnb ROI: 3.07% Traditional ROI: 1.54%
3640 Estelle Ct CHESAPEAKE BEACH, MD 3640 Estelle Ct, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	5 beds \| 4 baths \| 6,659 sq.ft.	$989,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.26% Airbnb Rental Income: $null Traditional Rental Income: $3223 Airbnb ROI: N/A Traditional ROI: 1.26%
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.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.97% Airbnb Rental Income: $null Traditional Rental Income: $3752 Airbnb ROI: N/A Traditional ROI: 4.97%
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: 0.87% Traditional cash on cash: 0.45% Airbnb Rental Income: $2511 Traditional Rental Income: $1591 Airbnb ROI: 0.87% Traditional ROI: 0.45%
3606 27th St CHESAPEAKE BEACH, MD PRICED UNDER VALUE - OWNER READY TO GO - Location location location - Lovely Chesape...	4 beds \| 2 baths \| 2,444 sq.ft.	$399,900	Airbnb cash on cash: 4.67% Traditional cash on cash: 6.13% Airbnb Rental Income: $3269 Traditional Rental Income: $3081 Airbnb ROI: 4.67% Traditional ROI: 6.13%
4820 Sherwood Ave CHESAPEAKE BEACH, MD Opportunity to obtain a spacious home in a community with beach access. The Breezy Point C...	3 beds \| 2 baths \| 2,632 sq.ft.	$360,000	Airbnb cash on cash: 3.51% Traditional cash on cash: 3.71% Airbnb Rental Income: $2672 Traditional Rental Income: $2103 Airbnb ROI: 3.51% Traditional ROI: 3.71%
4010 Beach Dr CHESAPEAKE BEACH, MD 4010 Beach Dr, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	3 beds \| 2 baths \| 2,296 sq.ft.	$535,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 2.23% Airbnb Rental Income: $2672 Traditional Rental Income: $2270 Airbnb ROI: 1.76% Traditional ROI: 2.23%
8407 Wesley Stinnett Blvd CHESAPEAKE BEACH, MD 8407 Wesley Stinnett Blvd, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	7 beds \| 3 baths \| 4,278 sq.ft.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.23% Airbnb Rental Income: $null Traditional Rental Income: $2911 Airbnb ROI: N/A Traditional ROI: 2.23%
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.	$599,900	Airbnb cash on cash: 2.45% Traditional cash on cash: 3.12% Airbnb Rental Income: $3269 Traditional Rental Income: $2915 Airbnb ROI: 2.45% Traditional ROI: 3.12%
2295 Sansbury Dr CHESAPEAKE BEACH, MD Welcome to easy one-level living in the sought-after Richfield Station community! This wel...	3 beds \| 2 baths \| 2,719 sq.ft.	$489,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 2.73% Airbnb Rental Income: $2672 Traditional Rental Income: $2242 Airbnb ROI: 2.29% Traditional ROI: 2.73%
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.	$685,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.22% Airbnb Rental Income: $null Traditional Rental Income: $2872 Airbnb ROI: N/A Traditional ROI: 2.22%
2735 Braeburn Ln CHESAPEAKE BEACH, MD Fabulous opportunity to own this well-maintained 3-bedroom, 2-bath split foyer in the desi...	3 beds \| 2 baths \| 1,856 sq.ft.	$444,990	Airbnb cash on cash: 2.84% Traditional cash on cash: 3.14% Airbnb Rental Income: $2672 Traditional Rental Income: $2161 Airbnb ROI: 2.84% Traditional ROI: 3.14%
4416 Snowy Egret Ct CHESAPEAKE BEACH, MD 4416 Snowy Egret Ct, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	5 beds \| 3 baths \| 3,048 sq.ft.	$719,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.99% Airbnb Rental Income: $null Traditional Rental Income: $2840 Airbnb ROI: N/A Traditional ROI: 1.99%
3304 Burgess Rd CHESAPEAKE BEACH, MD 3304 Burgess Rd, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	2 beds \| 3 baths \| 1,352 sq.ft.	$225,000	Airbnb cash on cash: 6.43% Traditional cash on cash: 6.06% Airbnb Rental Income: $2511 Traditional Rental Income: $1826 Airbnb ROI: 6.43% Traditional ROI: 6.06%
3555 Christiana Ct CHESAPEAKE BEACH, MD 3555 Christiana Ct, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	5 beds \| 3 baths \| 3,837 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.64% Airbnb Rental Income: $null Traditional Rental Income: $2955 Airbnb ROI: N/A Traditional ROI: 2.64%
2643 Richfield Ln CHESAPEAKE BEACH, MD 2643 Richfield Ln, CHESAPEAKE BEACH, MD 20732 \| Single Family Residential	5 beds \| 3 baths \| 3,060 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.66% Airbnb Rental Income: $null Traditional Rental Income: $3004 Airbnb ROI: N/A Traditional ROI: 2.66%

Your search for investment property begins and ends here

Single Family Homes 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: 1.55%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $3269

Traditional Rental Income: $3385

Airbnb ROI: 1.55%

Traditional ROI: 2.73%

3955 Breezy Point Rd

CHESAPEAKE BEACH, MD

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

$599,900

Airbnb cash on cash: 2.54%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $3269

Traditional Rental Income: $3189

Airbnb ROI: 2.54%

Traditional ROI: 3.7%

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%

7436 C St

CHESAPEAKE BEACH, MD

3 beds | 2 baths | 1,354 sq.ft.

$419,000

Airbnb cash on cash: 3.35%

Traditional cash on cash: 3.71%

Airbnb Rental Income: $2672

Traditional Rental Income: $2179

Airbnb ROI: 3.35%

Traditional ROI: 3.71%

2425 Harrison Ct

CHESAPEAKE BEACH, MD

4 beds | 2 baths | 3,570 sq.ft.

$665,000

Airbnb cash on cash: 2%

Traditional cash on cash: 2.37%

Airbnb Rental Income: $3269

Traditional Rental Income: $2765

Airbnb ROI: 2%

Traditional ROI: 2.37%

3804 16th St

CHESAPEAKE BEACH, MD

4 beds | 2 baths | 2,176 sq.ft.

$585,000

Airbnb cash on cash: 2.94%

Traditional cash on cash: 2.71%

Airbnb Rental Income: $3269

Traditional Rental Income: $2411

Airbnb ROI: 2.94%

Traditional ROI: 2.71%

8256 D St

CHESAPEAKE BEACH, MD

2 beds | 2 baths | 900 sq.ft.

$380,000

Airbnb cash on cash: 3.53%

Traditional cash on cash: 2.96%

Airbnb Rental Income: $2511

Traditional Rental Income: $1701

Airbnb ROI: 3.53%

Traditional ROI: 2.96%

3611 Karen Dr

CHESAPEAKE BEACH, MD

4 beds | 2 baths | 2,706 sq.ft.

$659,900

Airbnb cash on cash: 2.26%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $3269

Traditional Rental Income: $3293

Airbnb ROI: 2.26%