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
1090 BROADVIEW DR Annapolis, MD Welcome home to this cozy four bedroom, two full bath split foyer in sought after Cape St ...	4 beds \| 2 baths \| N/A	$550,000	Airbnb cash on cash: 2.63% Traditional cash on cash: 3.36% Airbnb Rental Income: $3104 Traditional Rental Income: $2771 Airbnb ROI: 2.63% Traditional ROI: 3.36%
1915 TOWNE CENTRE Boulevard unit: 513 Annapolis, MD This exceptional 5th-floor condo offers a one-of-a-kind, unique floor plan with breathtaki...	2 beds \| 2 baths \| 1,485 sq.ft.	$549,000	Airbnb cash on cash: -1.35% Traditional cash on cash: 0.76% Airbnb Rental Income: $2338 Traditional Rental Income: $2844 Airbnb ROI: -1.35% Traditional ROI: 0.76%
190 DUKE OF GLOUCESTER Street Annapolis, MD Historic charm and everyday comfort come together beautifully in this spacious Victorian i...	4 beds \| 5 baths \| 3,393 sq.ft.	$1,500,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 1.88% Airbnb Rental Income: $3104 Traditional Rental Income: $5080 Airbnb ROI: -0.04% Traditional ROI: 1.88%
52 PRIMROSE HILL Lane Annapolis, MD Modern accents meet classic Georgian design in a downtown Annapolis private enclave of cus...	5 beds \| 5 baths \| 3,978 sq.ft.	$924,900	Airbnb cash on cash: 1.01% Traditional cash on cash: 3.31% Airbnb Rental Income: $3871 Traditional Rental Income: $5022 Airbnb ROI: 1.01% Traditional ROI: 3.31%
3280 ARUNDEL ON THE BAY Road Annapolis, MD Significant Price Improvement!! A rare opportunity! Priced to sell, won't last long. Welco...	5 beds \| 5 baths \| 3,144 sq.ft.	$850,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 4.21% Airbnb Rental Income: $3871 Traditional Rental Income: $4883 Airbnb ROI: 1.88% Traditional ROI: 4.21%
1109 BOUCHER Avenue Annapolis, MD Greet neighbors from the front porch or entertain them on the private, fenced rear patio. ...	4 beds \| 5 baths \| 3,779 sq.ft.	$1,529,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 1.47% Airbnb Rental Income: $3104 Traditional Rental Income: $4864 Airbnb ROI: -0.27% Traditional ROI: 1.47%
1576 SAINT MARGARETS Road Annapolis, MD Welcome to 1576 St. Margaret's Road, a meticulously rebuilt rancher set on a peaceful 1.89...	4 beds \| 2 baths \| 1,792 sq.ft.	$690,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 2.44% Airbnb Rental Income: $3104 Traditional Rental Income: $2950 Airbnb ROI: 1.58% Traditional ROI: 2.44%
930 ASTERN Way unit: 304 Annapolis, MD Welcome to 930 Astern Way - a spacious and beautifully updated 1-bedroom, 1 1/2-bath condo...	1 beds \| 2 baths \| 1,152 sq.ft.	$275,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 2.13% Airbnb Rental Income: $1744 Traditional Rental Income: $2070 Airbnb ROI: -0.97% Traditional ROI: 2.13%
1014 WELLS Avenue Annapolis, MD Welcome Home to Eastport. Walk to the Eastport Shopping center for breakfast or to downtow...	4 beds \| 2 baths \| 880 sq.ft.	$430,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 3.24% Airbnb Rental Income: $3104 Traditional Rental Income: $2363 Airbnb ROI: 3.33% Traditional ROI: 3.24%
1915 TOWNE CENTRE Boulevard unit: 403 Annapolis, MD Welcome to the highly sought-after "Davenport" corner unit in the prestigious GrandView co...	2 beds \| 2 baths \| 1,602 sq.ft.	$695,000	Airbnb cash on cash: -1.63% Traditional cash on cash: -0.15% Airbnb Rental Income: $2338 Traditional Rental Income: $2724 Airbnb ROI: -1.63% Traditional ROI: -0.15%
99 SUMMERFIELD Drive Annapolis, MD Coming soon! Hardwood throughout, updates to the kitchens and bathrooms, fully finished ba...	4 beds \| 3 baths \| 1,980 sq.ft.	$524,900	Airbnb cash on cash: 2.72% Traditional cash on cash: 3.83% Airbnb Rental Income: $3104 Traditional Rental Income: $2939 Airbnb ROI: 2.72% Traditional ROI: 3.83%
310 GIDDINGS Avenue Annapolis, MD Welcome to 310 Giddings Avenue, a stunningly re-imagined Craftsman-style home on an expans...	3 beds \| 3 baths \| 3,218 sq.ft.	$1,750,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 0.42% Airbnb Rental Income: $2680 Traditional Rental Income: $3351 Airbnb ROI: -0.39% Traditional ROI: 0.42%
141 WEST Street unit: 201 Annapolis, MD Welcome to 141 West a boutique building styled after one of Manhattan's most iconic neighb...	1 beds \| 1 baths \| 612 sq.ft.	$482,500	Airbnb cash on cash: -0.56% Traditional cash on cash: 1.49% Airbnb Rental Income: $1744 Traditional Rental Income: $2190 Airbnb ROI: -0.56% Traditional ROI: 1.49%
7002 CHANNEL VILLAGE Court unit: 101 Annapolis, MD MOTIVATED SELLER!!!! This is a fabulous unit, and Welcome to Chesapeake Harbour! This beau...	2 beds \| 2 baths \| 1,319 sq.ft.	$525,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 0.8% Airbnb Rental Income: $2338 Traditional Rental Income: $2002 Airbnb ROI: 0.31% Traditional ROI: 0.8%
163 PRINCE GEORGE ST Annapolis, MD Located on one of the most charming and desirable streets in Historic Annapolis, this beau...	3 beds \| 3 baths \| N/A	$1,425,000	Airbnb cash on cash: -0.6% Traditional cash on cash: -0.14% Airbnb Rental Income: $2680 Traditional Rental Income: $2654 Airbnb ROI: -0.6% Traditional ROI: -0.14%
1002 TYLER Avenue Annapolis, MD Location Location location!! Modern rancher style home located near everything Annapolis h...	5 beds \| 2 baths \| 1,920 sq.ft.	$565,000	Airbnb cash on cash: 3.65% Traditional cash on cash: 3.45% Airbnb Rental Income: $3871 Traditional Rental Income: $2932 Airbnb ROI: 3.65% Traditional ROI: 3.45%
1223 MADISON Street Annapolis, MD Fully updated 4-bedroom, 2-bath home in the heart of Eastport offering modern finishes, fl...	4 beds \| 2 baths \| 1,488 sq.ft.	$609,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 2.81% Airbnb Rental Income: $3104 Traditional Rental Income: $2812 Airbnb ROI: 2.08% Traditional ROI: 2.81%
316 BURNSIDE ST #203 Annapolis, MD Welcome to the sought-after Newport Condominiums in Eastport, where coastal charm meets wa...	1 beds \| 1 baths \| N/A	$482,000	Airbnb cash on cash: -0.18% Traditional cash on cash: -0.02% Airbnb Rental Income: $1744 Traditional Rental Income: $1337 Airbnb ROI: -0.18% Traditional ROI: -0.02%
605 ADMIRAL DR #301 Annapolis, MD HURRY! This location is EVERTHING! Ready for a low-maintenance lifestyle? Experience effor...	2 beds \| 2 baths \| N/A	$395,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 1.95% Airbnb Rental Income: $2338 Traditional Rental Income: $2019 Airbnb ROI: 1.25% Traditional ROI: 1.95%
3 ELLIOTT Road Annapolis, MD 3 Elliott Road offers a fantastic opportunity to own a well-maintained two-unit duplex wit...	4 beds \| 2 baths \| 2,928 sq.ft.	$745,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 2.64% Airbnb Rental Income: $3104 Traditional Rental Income: $3030 Airbnb ROI: 1.73% Traditional ROI: 2.64%
165 KING GEORGE Street Annapolis, MD There are so many option available for this property in the heart of Historic Annapolis. Y...	N/A beds \| N/A 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%
2114 CHESAPEAKE HARBOUR Drive E unit: 202 Annapolis, MD WATCH THE SUNSETS & ENJOY THE BREATHTAKING MARINA VIEWS FROM THIS BEAUTIFUL 3 BEDROOM, 3 F...	3 beds \| 3 baths \| 1,748 sq.ft.	$725,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 0.51% Airbnb Rental Income: $2680 Traditional Rental Income: $2904 Airbnb ROI: -0.76% Traditional ROI: 0.51%
2568 GLEN Cove Annapolis, MD OPEN HOUSE SUNDAY 3/8 11-1. Tucked away at the end of a quiet cul-de-sac, this two-level h...	3 beds \| 3 baths \| 1,512 sq.ft.	$499,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 3.24% Airbnb Rental Income: $2680 Traditional Rental Income: $2765 Airbnb ROI: 1.7% Traditional ROI: 3.24%
220 WEST Street Annapolis, MD Welcome to 220 West Street in Annapolis, Maryland. A rare, fully gut-renovated detached pr...	3 beds \| 2 baths \| 1,540 sq.ft.	$924,900	Airbnb cash on cash: 0.6% Traditional cash on cash: 0.57% Airbnb Rental Income: $2680 Traditional Rental Income: $2023 Airbnb ROI: 0.6% Traditional ROI: 0.57%
79 WINDWHISPER Lane Annapolis, MD Motivated Sellers!! Price Just Improved!! Rare Opportunity in an Amazing Annapolis Neighbo...	4 beds \| 4 baths \| 2,560 sq.ft.	$629,999	Airbnb cash on cash: 1.89% Traditional cash on cash: 3.56% Airbnb Rental Income: $3104 Traditional Rental Income: $3378 Airbnb ROI: 1.89% Traditional ROI: 3.56%
400 JEFFERSON Street Annapolis, MD Nestled in the heart of historic Eastport Annapolis, this coastal craftsman has been exten...	4 beds \| 3 baths \| 3,640 sq.ft.	$1,990,000	Airbnb cash on cash: -0.84% Traditional cash on cash: -0.29% Airbnb Rental Income: $3104 Traditional Rental Income: $3405 Airbnb ROI: -0.84% Traditional ROI: -0.29%
709 SKIPPERS Lane Annapolis, MD Welcome to 709 Skippers Lane, a rare and versatile Live/Work townhome in the soughtafter V...	3 beds \| 4 baths \| 3,016 sq.ft.	$637,500	Airbnb cash on cash: 0.76% Traditional cash on cash: 3.14% Airbnb Rental Income: $2680 Traditional Rental Income: $3458 Airbnb ROI: 0.76% Traditional ROI: 3.14%

Real Estate investment in Annapolis, MD

There are 215 properties for sale in the city of Annapolis . The median list price in Annapolis is $617,425 and the average price per square foot is $287. In April 2026, the average monthly cash on cash return in Annapolis is 1.00%. The average monthly rental income in Annapolis is $2,446.

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

There are 215 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

1090 BROADVIEW DR

Annapolis, MD

4 beds | 2 baths | N/A

$550,000

Airbnb cash on cash: 2.63%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $3104

Traditional Rental Income: $2771

Airbnb ROI: 2.63%

Traditional ROI: 3.36%

1915 TOWNE CENTRE Boulevard unit: 513

Annapolis, MD

2 beds | 2 baths | 1,485 sq.ft.

$549,000

Airbnb cash on cash: -1.35%

Traditional cash on cash: 0.76%

Airbnb Rental Income: $2338

Traditional Rental Income: $2844

Airbnb ROI: -1.35%

Traditional ROI: 0.76%

190 DUKE OF GLOUCESTER Street

Annapolis, MD

4 beds | 5 baths | 3,393 sq.ft.

$1,500,000

Airbnb cash on cash: -0.04%

Traditional cash on cash: 1.88%

Airbnb Rental Income: $3104

Traditional Rental Income: $5080

Airbnb ROI: -0.04%

Traditional ROI: 1.88%

52 PRIMROSE HILL Lane

Annapolis, MD

5 beds | 5 baths | 3,978 sq.ft.

$924,900

Airbnb cash on cash: 1.01%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $3871

Traditional Rental Income: $5022

Airbnb ROI: 1.01%

Traditional ROI: 3.31%

3280 ARUNDEL ON THE BAY Road

Annapolis, MD

5 beds | 5 baths | 3,144 sq.ft.

$850,000

Airbnb cash on cash: 1.88%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $3871

Traditional Rental Income: $4883

Airbnb ROI: 1.88%

Traditional ROI: 4.21%

1109 BOUCHER Avenue

Annapolis, MD

4 beds | 5 baths | 3,779 sq.ft.

$1,529,000

Airbnb cash on cash: -0.27%

Traditional cash on cash: 1.47%

Airbnb Rental Income: $3104

Traditional Rental Income: $4864

Airbnb ROI: -0.27%

Traditional ROI: 1.47%

1576 SAINT MARGARETS Road

Annapolis, MD

4 beds | 2 baths | 1,792 sq.ft.

$690,000

Airbnb cash on cash: 1.58%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $3104

Traditional Rental Income: $2950

Airbnb ROI: 1.58%

Traditional ROI: 2.44%

930 ASTERN Way unit: 304

Annapolis, MD

1 beds | 2 baths | 1,152 sq.ft.

$275,000

Airbnb cash on cash: -0.97%

Traditional cash on cash: 2.13%

Airbnb Rental Income: $1744

Traditional Rental Income: $2070

Airbnb ROI: -0.97%