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
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%
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	$475,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 1.36% Airbnb Rental Income: $891 Traditional Rental Income: $1491 Airbnb ROI: -0.75% Traditional ROI: 1.36%
2550 Woodland Pl CHESAPEAKE BEACH, MD Move right in to this gorgeous end unit w/ garage townhouse. Close to the boardwalk, beac...	3 beds \| 1 baths \| 1,806 sq.ft.	$405,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 1.78% Airbnb Rental Income: $2602 Traditional Rental Income: $1489 Airbnb ROI: 3.08% Traditional ROI: 1.78%
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%
8418 Clear Spring Dr #1 CHESAPEAKE BEACH, MD Watch the sunlight SHINE through this end unit townhome in Richfield Station! 3 fully fini...	4 beds \| 3 baths \| 1,876 sq.ft.	$395,000	Airbnb cash on cash: 3.13% Traditional cash on cash: 3.96% Airbnb Rental Income: $2877 Traditional Rental Income: $2517 Airbnb ROI: 3.13% Traditional ROI: 3.96%
8445 Clear Spring Dr CHESAPEAKE BEACH, MD Welcome to 8445 Clear Spring Drive, where updated living, a flexible floor plan, and a pea...	4 beds \| 3 baths \| 1,824 sq.ft.	$385,000	Airbnb cash on cash: 3.18% Traditional cash on cash: 3.8% Airbnb Rental Income: $2877 Traditional Rental Income: $2435 Airbnb ROI: 3.18% Traditional ROI: 3.8%
2233 Ivy Ln #3 CHESAPEAKE BEACH, MD Enjoy easy, low-maintenance living in this beautifully maintained GROUND LEVEL 2-bedroom, ...	2 beds \| 2 baths \| 1,658 sq.ft.	$360,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 2.1% Airbnb Rental Income: $2901 Traditional Rental Income: $1972 Airbnb ROI: 2.86% Traditional ROI: 2.1%
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%
2221 Ivy Ln #G-9 CHESAPEAKE BEACH, MD Nestled in the charming Richfield Station Village, this delightful Colonial townhouse offe...	3 beds \| 2 baths \| 1,600 sq.ft.	$359,900	Airbnb cash on cash: 2.12% Traditional cash on cash: 2.12% Airbnb Rental Income: $2602 Traditional Rental Income: $1979 Airbnb ROI: 2.12% Traditional ROI: 2.12%
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%
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: 3.17% Traditional cash on cash: 4.6% Airbnb Rental Income: $891 Traditional Rental Income: $680 Airbnb ROI: 3.17% 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.	$136,900	Airbnb cash on cash: 1.08% Traditional cash on cash: 4.11% Airbnb Rental Income: $891 Traditional Rental Income: $952 Airbnb ROI: 1.08% Traditional ROI: 4.11%
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: 6.23% Traditional cash on cash: 8.58% Airbnb Rental Income: $891 Traditional Rental Income: $684 Airbnb ROI: 6.23% Traditional ROI: 8.58%
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%
8054 Windward Key Dr CHESAPEAKE BEACH, MD MAJOR PRICE IMPROVEMENT. Experience an elevated waterfront lifestyle in the coveted Windwa...	4 beds \| 4 baths \| 2,876 sq.ft.	$774,900	Airbnb cash on cash: 0.42% Traditional cash on cash: 3.91% Airbnb Rental Income: $2877 Traditional Rental Income: $4727 Airbnb ROI: 0.42% Traditional ROI: 3.91%
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: 0.36% Traditional cash on cash: 1.53% Airbnb Rental Income: $891 Traditional Rental Income: $774 Airbnb ROI: 0.36% 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: 2.71% Traditional cash on cash: 5.02% Airbnb Rental Income: $891 Traditional Rental Income: $776 Airbnb ROI: 2.71% 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: 0.63% Traditional cash on cash: 1.92% Airbnb Rental Income: $891 Traditional Rental Income: $774 Airbnb ROI: 0.63% Traditional ROI: 1.92%
8076 Windward Key Dr CHESAPEAKE BEACH, MD COASTAL LUXURY MEETS EVERYDAY VACATION LIVING in Windward Key on the Chesapeake Bay. Exper...	4 beds \| 4 baths \| 2,950 sq.ft.	$749,900	Airbnb cash on cash: 0.65% Traditional cash on cash: 4.55% Airbnb Rental Income: $2877 Traditional Rental Income: $4933 Airbnb ROI: 0.65% Traditional ROI: 4.55%
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	$485,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 2.87% Airbnb Rental Income: $2602 Traditional Rental Income: $2447 Airbnb ROI: 1.84% Traditional ROI: 2.87%
8048 Windward Key Dr CHESAPEAKE BEACH, MD Discover coastal living at its finest at 8048 Windward Key Dr, Chesapeake Beach! This "as-...	3 beds \| 4 baths \| 2,583 sq.ft.	$759,900	Airbnb cash on cash: 0.11% Traditional cash on cash: 3.43% Airbnb Rental Income: $2602 Traditional Rental Income: $4333 Airbnb ROI: 0.11% Traditional ROI: 3.43%
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%

Real Estate investment in Chesapeake-beach, MD

There are 65 properties for sale in the city of Chesapeake Beach . The median list price in Chesapeake Beach is $474,916 and the average price per square foot is $200. In October 2026, the average monthly cash on cash return in Chesapeake Beach is 3.00%. The average monthly rental income in Chesapeake Beach is $2,447.

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

There are 65 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 $2,447.

Your search for investment property begins and ends here

Investment Property 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%

5209 Larchmont Dr

CHESAPEAKE BEACH, MD

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

$475,000

Airbnb cash on cash: -0.75%

Traditional cash on cash: 1.36%

Airbnb Rental Income: $891

Traditional Rental Income: $1491

Airbnb ROI: -0.75%

Traditional ROI: 1.36%

2550 Woodland Pl

CHESAPEAKE BEACH, MD

3 beds | 1 baths | 1,806 sq.ft.

$405,000

Airbnb cash on cash: 3.08%

Traditional cash on cash: 1.78%

Airbnb Rental Income: $2602

Traditional Rental Income: $1489

Airbnb ROI: 3.08%

Traditional ROI: 1.78%

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%