Real Estate Investment Properties for Sale in Annapolis, MD

Looking for investment property in Annapolis, MD with high ROI ?

Explore a variety of short-term homes & houses in Annapolis, MD. Invest wisely with VRBO & Annapolis, 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 Annapolis, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
5 Park Pl #431 Annapolis, MD PLEASE TAKE A LOOK AT EVERY CONDO IN THE BUILDING SOLD IN THE LAST YEAR AND THEN MAKE AN A...	1 beds \| 1 baths \| 839 sq.ft.	$489,900	Airbnb cash on cash: -1.16% Traditional cash on cash: 0.14% Airbnb Rental Income: $1744 Traditional Rental Income: $1863 Airbnb ROI: -1.16% Traditional ROI: 0.14%
1915 Towne Centre Blvd #807 Annapolis, MD FRESH INTERIOR PAINT THROUGHOUT - A PRISTINE, NEUTRAL PALETTE READY FOR YOUR STYLE!! SELLE...	2 beds \| 2 baths \| 1,246 sq.ft.	$545,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 0.96% Airbnb Rental Income: $2338 Traditional Rental Income: $2694 Airbnb ROI: -0.88% Traditional ROI: 0.96%
1394 Stonecreek Rd Annapolis, MD Beautifully renovated and updated contemporary home close to all that Historic Annapolis h...	4 beds \| 3 baths \| 2,736 sq.ft.	$585,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 2.85% Airbnb Rental Income: $3104 Traditional Rental Income: $2779 Airbnb ROI: 2.15% Traditional ROI: 2.85%
474 Ruffian Ct Annapolis, MD Freshly updated Three Bath & Two Bath home featuring new flooring, fresh paint, stainless ...	3 beds \| 2 baths \| 1,232 sq.ft.	$374,950	Airbnb cash on cash: 3.94% Traditional cash on cash: 4.67% Airbnb Rental Income: $2680 Traditional Rental Income: $2303 Airbnb ROI: 3.94% Traditional ROI: 4.67%
1840 Kimberwicke Pl Annapolis, MD ..HUGH CUSTONM BUILT HOME ON 6 ACRES... IT HAS THE GAS HEAT , GAS FIREPLACE , HARDWOOD FL...	5 beds \| 2 baths \| 2,958 sq.ft.	$825,000	Airbnb cash on cash: 2.02% Traditional cash on cash: N/A Airbnb Rental Income: $3871 Traditional Rental Income: $0 Airbnb ROI: 2.02% Traditional ROI: N/A
606 Snow Goose Ln Annapolis, MD This home has it all. Gorgeous Brazilian hardwoods throughout! Gourmet kit w/top of the li...	4 beds \| 2 baths \| 2,004 sq.ft.	$565,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 4.6% Airbnb Rental Income: $3104 Traditional Rental Income: $3496 Airbnb ROI: 2.51% Traditional ROI: 4.6%
120 WATERLINE Court Annapolis, MD Welcome to 120 Waterline Court - a beautifully maintained end-unit residence offering exce...	3 beds \| 4 baths \| 2,016 sq.ft.	$559,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 2.86% Airbnb Rental Income: $2680 Traditional Rental Income: $2939 Airbnb ROI: 1.15% Traditional ROI: 2.86%
111 Clay St Annapolis, MD Major Price Adjustment!! Great opportunity in West Annapolis! Discover the charm of 111 Cl...	3 beds \| 1 baths \| 1,568 sq.ft.	$525,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 3.44% Airbnb Rental Income: $2680 Traditional Rental Income: $2678 Airbnb ROI: 2.15% Traditional ROI: 3.44%
2157 Scotts Crossing Ct #204 Annapolis, MD BRIGHT & CHEERFUL 2ND FLOOR 2 BR/2 FBA CONDO IN CONVENIENTLY LOCATED SCOTT'S CROSSING. NE...	2 beds \| 2 baths \| 1,111 sq.ft.	$349,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 3.38% Airbnb Rental Income: $2338 Traditional Rental Income: $2137 Airbnb ROI: 2.23% Traditional ROI: 3.38%
215 Chester Ave Annapolis, MD EXCITING PRICE IMPROVEMENT! SELLER HAS REDUCED THE PRICE-DON'T MISS THIS GREAT OPPORTUNITY...	4 beds \| 3 baths \| 3,421 sq.ft.	$1,799,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 0.35% Airbnb Rental Income: $3104 Traditional Rental Income: $3908 Airbnb ROI: -0.55% Traditional ROI: 0.35%
1071 Cedar Ridge Ct Annapolis, MD Nestled in the Cedar Ridge community, this contemporary end-of-row townhouse offers a perf...	3 beds \| 2 baths \| 1,320 sq.ft.	$395,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 3.61% Airbnb Rental Income: $2680 Traditional Rental Income: $2469 Airbnb ROI: 2.46% Traditional ROI: 3.61%
9 Shipwright St Annapolis, MD Waterfront on Spa Creek in Downtown Annapolis!!! Property features open floor plan, walls ...	3 beds \| 2 baths \| 2,621 sq.ft.	$3,495,000	Airbnb cash on cash: -1.15% Traditional cash on cash: -0.88% Airbnb Rental Income: $2680 Traditional Rental Income: $2939 Airbnb ROI: -1.15% Traditional ROI: -0.88%
1915 Towne Centre Blvd #1004 Annapolis, MD Time to Make a Lifestyle Change - Stunning & Fabulous at The GrandView! Welcome to The Fla...	2 beds \| 2 baths \| 1,794 sq.ft.	$975,000	Airbnb cash on cash: -1.77% Traditional cash on cash: -0.69% Airbnb Rental Income: $2338 Traditional Rental Income: $2737 Airbnb ROI: -1.77% Traditional ROI: -0.69%
8 ASHFORD CT Annapolis, MD Price Adjustment! Welcome to 8 Ashford Ct - Modern Living in the Heart of Annapolis! Now o...	2 beds \| 2 baths \| N/A	$399,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 2.97% Airbnb Rental Income: $2338 Traditional Rental Income: $2034 Airbnb ROI: 2.23% Traditional ROI: 2.97%
1984 Marconi Cir Annapolis, MD Perfect Heritage Harbour Location. Lovely end of row unit with additional daylight through...	2 beds \| 2 baths \| 1,434 sq.ft.	$489,900	Airbnb cash on cash: 1.31% Traditional cash on cash: 2.8% Airbnb Rental Income: $2338 Traditional Rental Income: $2445 Airbnb ROI: 1.31% Traditional ROI: 2.8%
1553 Star Pine Dr Annapolis, MD Welcome to your new home in Whispering Woods! This charming duplex offers practical living...	2 beds \| 1 baths \| 1,060 sq.ft.	$346,000	Airbnb cash on cash: 3.13% Traditional cash on cash: 4.38% Airbnb Rental Income: $2338 Traditional Rental Income: $2165 Airbnb ROI: 3.13% Traditional ROI: 4.38%
2900 Shipmaster Way #216 Annapolis, MD Welcome to Waterfront living at its finest! This exclusive second floor unit is a rare gem...	2 beds \| 2 baths \| 1,048 sq.ft.	$347,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 4.76% Airbnb Rental Income: $2338 Traditional Rental Income: $2221 Airbnb ROI: 3.34% Traditional ROI: 4.76%
7002 Channel Village Ct #101 Annapolis, MD *PRICE LOWEREDSELLER WILL ENTERTAIN ALL OFFERS*Resort Style Community on the Chesape...	2 beds \| 2 baths \| 1,319 sq.ft.	$525,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 1.08% Airbnb Rental Income: $2338 Traditional Rental Income: $2137 Airbnb ROI: 0.31% Traditional ROI: 1.08%
547 LEFTWICH LN #88 Annapolis, MD BIG PRICE IMPROVEMENT! COSMOPOLITAN ANNAPOLIS TOWNHOME BOASTING SKYLINE ROOFTOP DECK! ADM...	3 beds \| 3 baths \| N/A	$560,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 3.49% Airbnb Rental Income: $2680 Traditional Rental Income: $2973 Airbnb ROI: 1.71% Traditional ROI: 3.49%
161 E BAY VIEW DR Annapolis, MD Welcome home to this fantastic contemporary style where coastal charm meets modern connive...	4 beds \| 4 baths \| N/A	$949,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 2.13% Airbnb Rental Income: $3104 Traditional Rental Income: $3705 Airbnb ROI: 0.65% Traditional ROI: 2.13%
1002 Tyler Ave Annapolis, MD Location Location location!! Modern rancher style home located near everything Annapolis h...	5 beds \| 2 baths \| 1,920 sq.ft.	$580,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 3.33% Airbnb Rental Income: $3871 Traditional Rental Income: $2932 Airbnb ROI: 3.53% Traditional ROI: 3.33%
2704 Summerview Way #103 Annapolis, MD Peaceful living in this private, spacious condo. The living room features a wood-burning...	2 beds \| 2 baths \| 1,285 sq.ft.	$365,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 2.67% Airbnb Rental Income: $2338 Traditional Rental Income: $2082 Airbnb ROI: 1.72% Traditional ROI: 2.67%
1915 Towne Centre Blvd #402 Annapolis, MD CONTRACT ACCEPTED AND ACCEPTING BACK UP OFFERS This is it!!! Your chance to own your plac...	2 beds \| 2 baths \| 1,485 sq.ft.	$539,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 0.25% Airbnb Rental Income: $2338 Traditional Rental Income: $2529 Airbnb ROI: -1.27% Traditional ROI: 0.25%
932 Riversedge Cir Annapolis, MD Welcome to 932 Riversedge Circle - a beautifully updated, one-level end-unit Villa in desi...	2 beds \| 1 baths \| 912 sq.ft.	$379,990	Airbnb cash on cash: 2.81% Traditional cash on cash: 1.8% Airbnb Rental Income: $2338 Traditional Rental Income: $1398 Airbnb ROI: 2.81% Traditional ROI: 1.8%
304-G Hilltop Ln Annapolis, MD Welcome home! This beautiful 2-bedroom, 2-bath condo in Annapolis! This spacious unit offe...	2 beds \| 2 baths \| 1,072 sq.ft.	$285,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 3.12% Airbnb Rental Income: $2338 Traditional Rental Income: $2031 Airbnb ROI: 2.11% Traditional ROI: 3.12%
165 King George St Annapolis, MD There are so many option available for this property in the heart of Historic Annapolis. Y...	4 beds \| 3 baths \| 2,649 sq.ft.	$1,375,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 0.68% Airbnb Rental Income: $1884 Traditional Rental Income: $3263 Airbnb ROI: -0.79% Traditional ROI: 0.68%
1915 Towne Centre Blvd #707 Annapolis, MD Fantastic 2 Bedroom condo with great views of Annapolis Towne Centre from the balcony with...	2 beds \| 2 baths \| 1,246 sq.ft.	$535,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 0.82% Airbnb Rental Income: $2338 Traditional Rental Income: $2514 Airbnb ROI: -0.68% Traditional ROI: 0.82%
133 Lake View Dr Annapolis, MD 133 Lake View Dr, Annapolis, MD 21403 \| Single Family Residential	5 beds \| 5 baths \| 4,308 sq.ft.	$1,400,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 1.6% Airbnb Rental Income: $3871 Traditional Rental Income: $4883 Airbnb ROI: 0.18% Traditional ROI: 1.6%
1403 Corey Ln Annapolis, MD Tucked away at the end of a quiet, secluded street off No Cherry Grove (one of the prettie...	4 beds \| 2 baths \| 1,960 sq.ft.	$925,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 2.33% Airbnb Rental Income: $3104 Traditional Rental Income: $3883 Airbnb ROI: 0.61% Traditional ROI: 2.33%
709 Skippers Ln Annapolis, MD Welcome to 709 Skippers Lane, a rare and versatile Live/Work townhome in the soughtafter V...	3 beds \| 2 baths \| 3,016 sq.ft.	$649,999	Airbnb cash on cash: 0.73% Traditional cash on cash: 3.06% Airbnb Rental Income: $2680 Traditional Rental Income: $3458 Airbnb ROI: 0.73% Traditional ROI: 3.06%
2707 Judson Pl Annapolis, MD Welcome to 2707 Judson Place in Riva Woods. This inviting home sits on a private, fenced c...	3 beds \| 2 baths \| 2,156 sq.ft.	$590,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 3.7% Airbnb Rental Income: $2680 Traditional Rental Income: $3172 Airbnb ROI: 1.65% Traditional ROI: 3.7%
1 Tucker St Annapolis, MD 30K Price Improvement! Seller motivated! Incredible West Annapolis home that has been reno...	3 beds \| 2 baths \| 1,869 sq.ft.	$1,145,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 1.05% Airbnb Rental Income: $2680 Traditional Rental Income: $3155 Airbnb ROI: 0.01% Traditional ROI: 1.05%
328 Bulwark Aly Annapolis, MD Welcome to this beautifully maintained 3 level end unit garage townhome in the sought afte...	3 beds \| 2 baths \| 2,000 sq.ft.	$615,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 3.23% Airbnb Rental Income: $2680 Traditional Rental Income: $3200 Airbnb ROI: 1.22% Traditional ROI: 3.23%
106 Stilly Way Annapolis, MD This stunning home is move-in ready and boasts high-end upgrades throughout. It features a...	4 beds \| 4 baths \| 4,594 sq.ft.	$974,990	Airbnb cash on cash: 1.27% Traditional cash on cash: 3.79% Airbnb Rental Income: $3104 Traditional Rental Income: $4686 Airbnb ROI: 1.27% Traditional ROI: 3.79%
2052 Quaker Way #7 Annapolis, MD This charming condo in the heart of Annapolis offers the perfect blend of comfort and conv...	2 beds \| 2 baths \| 1,122 sq.ft.	$364,990	Airbnb cash on cash: 2.18% Traditional cash on cash: 3.28% Airbnb Rental Income: $2338 Traditional Rental Income: $2137 Airbnb ROI: 2.18% Traditional ROI: 3.28%
1955 Marconi Cir Annapolis, MD Heritage Harbour a 55 plus community. Welcome Home to 1955 Marconi Cir. This two bedroom t...	2 beds \| 2 baths \| 1,200 sq.ft.	$445,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 2.73% Airbnb Rental Income: $2338 Traditional Rental Income: $2217 Airbnb ROI: 1.64% Traditional ROI: 2.73%

Real Estate investment in Annapolis, MD

There are 195 properties for sale in the city of Annapolis . The median list price in Annapolis is $639,950 and the average price per square foot is $265. In January 2026, the average monthly cash on cash return in Annapolis is 1.00%. The average monthly rental income in Annapolis is $2,352.

Annapolis, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 195 investment properties available for sale in Annapolis.

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

The ROI for Short-Term is higher than the Long-Term in Annapolis with average rental income of $2,680.

Your search for investment property begins and ends here

Investment Property for Sale in Annapolis, MD

5 Park Pl #431

Annapolis, MD

1 beds | 1 baths | 839 sq.ft.

$489,900

Airbnb cash on cash: -1.16%

Traditional cash on cash: 0.14%

Airbnb Rental Income: $1744

Traditional Rental Income: $1863

Airbnb ROI: -1.16%

Traditional ROI: 0.14%

1915 Towne Centre Blvd #807

Annapolis, MD

2 beds | 2 baths | 1,246 sq.ft.

$545,000

Airbnb cash on cash: -0.88%

Traditional cash on cash: 0.96%

Airbnb Rental Income: $2338

Traditional Rental Income: $2694

Airbnb ROI: -0.88%

Traditional ROI: 0.96%

1394 Stonecreek Rd

Annapolis, MD

4 beds | 3 baths | 2,736 sq.ft.

$585,000

Airbnb cash on cash: 2.15%

Traditional cash on cash: 2.85%

Airbnb Rental Income: $3104

Traditional Rental Income: $2779

Airbnb ROI: 2.15%

Traditional ROI: 2.85%

474 Ruffian Ct

Annapolis, MD

3 beds | 2 baths | 1,232 sq.ft.

$374,950

Airbnb cash on cash: 3.94%

Traditional cash on cash: 4.67%

Airbnb Rental Income: $2680

Traditional Rental Income: $2303

Airbnb ROI: 3.94%

Traditional ROI: 4.67%

1840 Kimberwicke Pl

Annapolis, MD

5 beds | 2 baths | 2,958 sq.ft.

$825,000

Airbnb cash on cash: 2.02%

Traditional cash on cash: N/A

Airbnb Rental Income: $3871

Traditional Rental Income: $0

Airbnb ROI: 2.02%

Traditional ROI: N/A

606 Snow Goose Ln

Annapolis, MD

4 beds | 2 baths | 2,004 sq.ft.

$565,000

Airbnb cash on cash: 2.51%

Traditional cash on cash: 4.6%

Airbnb Rental Income: $3104

Traditional Rental Income: $3496

Airbnb ROI: 2.51%

Traditional ROI: 4.6%

120 WATERLINE Court

Annapolis, MD

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

$559,000

Airbnb cash on cash: 1.15%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $2680

Traditional Rental Income: $2939

Airbnb ROI: 1.15%

Traditional ROI: 2.86%

111 Clay St

Annapolis, MD

3 beds | 1 baths | 1,568 sq.ft.

$525,000

Airbnb cash on cash: 2.15%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $2680

Traditional Rental Income: $2678

Airbnb ROI: 2.15%