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
66 FRANKLIN ST #20 Annapolis, MD Stylish Street-Level Condo in the Heart of Annapolis. Welcome to this spacious 1-bedroom, ...	1 beds \| 2 baths \| N/A	$725,000	Airbnb cash on cash: -2.71% Traditional cash on cash: -0.43% Airbnb Rental Income: $1077 Traditional Rental Income: $2248 Airbnb ROI: -2.71% Traditional ROI: -0.43%
1231 VAN BUREN Drive Annapolis, MD OPEN HOUSE 5/2&5/3 11-1 Welcome to Colony Hills, one of Eastport's most coveted neighb...	3 beds \| 2 baths \| 1,694 sq.ft.	$635,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 1.61% Airbnb Rental Income: $1648 Traditional Rental Income: $2175 Airbnb ROI: -0.06% Traditional ROI: 1.61%
7 SILVERWOOD Circle #3 Annapolis, MD Annapolis Living Without the Hassle - Renovated, Move-In Ready, and Priced to Move Renovat...	2 beds \| 2 baths \| N/A	$269,990	Airbnb cash on cash: -1.73% Traditional cash on cash: 3.4% Airbnb Rental Income: $1082 Traditional Rental Income: $2020 Airbnb ROI: -1.73% Traditional ROI: 3.4%
1107 BRASHEARS Street Annapolis, MD Discover the perfect blend of Annapolis charm and contemporary luxury at 1107 Brashears St...	5 beds \| 2 baths \| 1,800 sq.ft.	$825,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 1.43% Airbnb Rental Income: $1643 Traditional Rental Income: $2541 Airbnb ROI: -0.35% Traditional ROI: 1.43%
1915 TOWNE CENTRE Boulevard #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: -3.39% Traditional cash on cash: 0.76% Airbnb Rental Income: $1082 Traditional Rental Income: $2844 Airbnb ROI: -3.39% Traditional ROI: 0.76%
349 EPPING WAY Annapolis, MD Priced to sell. Exceptional Value for over 3,292 finished sq ft. tucked among the trees in...	4 beds \| 3 baths \| N/A	$975,000	Airbnb cash on cash: -0.55% Traditional cash on cash: -1.39% Airbnb Rental Income: $2057 Traditional Rental Income: $763 Airbnb ROI: -0.55% Traditional ROI: -1.39%
3280 ARUNDEL ON THE BAY Road Annapolis, MD Welcome to this beautifully maintained 5 bed, 4.5 bath, colonial home situated on almost a...	5 beds \| 5 baths \| 3,144 sq.ft.	$824,900	Airbnb cash on cash: -0.45% Traditional cash on cash: 4.37% Airbnb Rental Income: $1643 Traditional Rental Income: $4883 Airbnb ROI: -0.45% Traditional ROI: 4.37%
1109 BOUCHER Avenue Annapolis, MD Living the Eastport lifestyle - This is what upscale, modern urban living is all about! It...	4 beds \| 5 baths \| 3,779 sq.ft.	$1,345,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 1.8% Airbnb Rental Income: $2057 Traditional Rental Income: $4864 Airbnb ROI: -0.87% Traditional ROI: 1.8%
1254 WASHINGTON DR Annapolis, MD Rare waterfront redevelopment opportunity in Annapolis. The existing structure is a comple...	5 beds \| 5 baths \| N/A	$1,000,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 3.33% Airbnb Rental Income: $1643 Traditional Rental Income: $5132 Airbnb ROI: -0.92% Traditional ROI: 3.33%
314 KINGSBERRY DR Annapolis, MD It's all about the land at this St. Margaret's Farm location with approximately 150 ft of ...	3 beds \| 3 baths \| N/A	$1,400,000	Airbnb cash on cash: -1.58% Traditional cash on cash: -0.26% Airbnb Rental Income: $1648 Traditional Rental Income: $2896 Airbnb ROI: -1.58% Traditional ROI: -0.26%
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.	$419,900	Airbnb cash on cash: 1.21% Traditional cash on cash: 3.34% Airbnb Rental Income: $2057 Traditional Rental Income: $2363 Airbnb ROI: 1.21% Traditional ROI: 3.34%
1915 TOWNE CENTRE Boulevard #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: -3.25% Traditional cash on cash: -0.15% Airbnb Rental Income: $1082 Traditional Rental Income: $2724 Airbnb ROI: -3.25% Traditional ROI: -0.15%
5 PARK PLACE #527 Annapolis, MD Nestled in the prestigious Park Place community, this exquisite mid-rise condominium build...	2 beds \| 2 baths \| N/A	$654,900	Airbnb cash on cash: -1.04% Traditional cash on cash: 1.31% Airbnb Rental Income: $1082 Traditional Rental Income: $2151 Airbnb ROI: -1.04% Traditional ROI: 1.31%
141 WEST Street #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: -1.79% Traditional cash on cash: 1.49% Airbnb Rental Income: $1077 Traditional Rental Income: $2190 Airbnb ROI: -1.79% Traditional ROI: 1.49%
1117 PRIMROSE CT #301 Annapolis, MD Located in the community of The Landing at Spa Creek, 1117 Primrose Ct #301 gives condo li...	2 beds \| 1 baths \| N/A	$269,000	Airbnb cash on cash: -1.47% Traditional cash on cash: 1.53% Airbnb Rental Income: $1082 Traditional Rental Income: $1473 Airbnb ROI: -1.47% Traditional ROI: 1.53%
3320 ARUNDEL ON THE BAY RD Annapolis, MD Welcome to 3320 Arundel on the Bay Road-where relaxed coastal living meets thoughtful desi...	3 beds \| 4 baths \| N/A	$625,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 3.53% Airbnb Rental Income: $1648 Traditional Rental Income: $3299 Airbnb ROI: -0.1% Traditional ROI: 3.53%
43 SHAW ST #G Annapolis, MD Welcome to 43 Shaw Street! A quaint 8-unit building located on a sleepy street in Downtown...	2 beds \| 2 baths \| N/A	$700,000	Airbnb cash on cash: -2.17% Traditional cash on cash: 0.21% Airbnb Rental Income: $1082 Traditional Rental Income: $2262 Airbnb ROI: -2.17% Traditional ROI: 0.21%
1561 RITCHIE Lane Annapolis, MD Welcome to Your Annapolis Dream Lifestyle! Fall in love with this sun-drenched, beautifull...	3 beds \| 3 baths \| 2,322 sq.ft.	$575,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 3.42% Airbnb Rental Income: $1648 Traditional Rental Income: $3145 Airbnb ROI: -0.24% Traditional ROI: 3.42%
1000 GOMOLJAK Lane Annapolis, MD Looking for a secluded Mountaintop home tucked away on 3.89 acres within 15 minutes from d...	4 beds \| 4 baths \| 3,620 sq.ft.	$919,990	Airbnb cash on cash: -0.25% Traditional cash on cash: 1.64% Airbnb Rental Income: $2057 Traditional Rental Income: $3142 Airbnb ROI: -0.25% Traditional ROI: 1.64%
4 SOUTHGATE Avenue Annapolis, MD An exceptional offering on Southgate Avenue in Murray Hill, this stately American Four Squ...	5 beds \| 5 baths \| 4,015 sq.ft.	$3,500,000	Airbnb cash on cash: -1.18% Traditional cash on cash: 0.15% Airbnb Rental Income: $1643 Traditional Rental Income: $5504 Airbnb ROI: -1.18% Traditional ROI: 0.15%
494 FAWNS WALK Annapolis, MD 2,748 Total Square feet! Welcome to 494 Fawns Walk... a home that truly unfolds as you mo...	3 beds \| 3 baths \| N/A	$535,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 3.07% Airbnb Rental Income: $1648 Traditional Rental Income: $2559 Airbnb ROI: 0.32% Traditional ROI: 3.07%
2607 COMPASS Drive Annapolis, MD Completely updated and impressively spacious, this beautifully maintained villa offers ove...	2 beds \| 3 baths \| 1,906 sq.ft.	$550,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 2.13% Airbnb Rental Income: $1082 Traditional Rental Income: $2368 Airbnb ROI: -1.09% Traditional ROI: 2.13%
207 1ST ST Annapolis, MD UPDATE: Open House this Saturday from 11-2pm. Seller is offering Seller help of $10,000 f...	4 beds \| 2 baths \| N/A	$484,900	Airbnb cash on cash: 1.18% Traditional cash on cash: 3.39% Airbnb Rental Income: $2057 Traditional Rental Income: $2528 Airbnb ROI: 1.18% Traditional ROI: 3.39%
404 PEACH Court Annapolis, MD Welcome to Walnut Ridge! This beautiful 3-level colonial townhouse boasts over 2,000 squar...	4 beds \| 4 baths \| 2,061 sq.ft.	$459,900	Airbnb cash on cash: 1.21% Traditional cash on cash: 5.05% Airbnb Rental Income: $2057 Traditional Rental Income: $3180 Airbnb ROI: 1.21% Traditional ROI: 5.05%
163 PRINCE GEORGE ST Annapolis, MD Exceptional new pricing creates a compelling offering in the heart of Historic Annapolis. ...	3 beds \| 3 baths \| N/A	$1,325,000	Airbnb cash on cash: -1.27% Traditional cash on cash: -0.07% Airbnb Rental Income: $1648 Traditional Rental Income: $2654 Airbnb ROI: -1.27% Traditional ROI: -0.07%
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: 0.13% Traditional cash on cash: 3.45% Airbnb Rental Income: $1643 Traditional Rental Income: $2932 Airbnb ROI: 0.13% Traditional ROI: 3.45%
2666 PEMAQUID Court Annapolis, MD Welcome to refined, effortless living in the highly sought-after 55+ community of Heritage...	2 beds \| 2 baths \| 1,464 sq.ft.	$719,900	Airbnb cash on cash: -1.13% Traditional cash on cash: 1.21% Airbnb Rental Income: $1082 Traditional Rental Income: $2287 Airbnb ROI: -1.13% Traditional ROI: 1.21%
152 JEFFERSON Street Annapolis, MD SAVINGS OPPORTUNITY! DON'T FORGET TO ASK US ABOUT THE SELLER 2-1 RATE BUYDOWN! RENOVATED E...	4 beds \| 4 baths \| 2,282 sq.ft.	$850,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 3.33% Airbnb Rental Income: $2057 Traditional Rental Income: $3862 Airbnb ROI: 0.38% Traditional ROI: 3.33%
203 VICTOR Parkway #H Annapolis, MD Welcome to Fairwinds of Annapolis, this delightful 2nd floor 2-bedroom, 2-bathroom garden ...	2 beds \| 2 baths \| 956 sq.ft.	$249,000	Airbnb cash on cash: -1.33% Traditional cash on cash: 3.65% Airbnb Rental Income: $1082 Traditional Rental Income: $1885 Airbnb ROI: -1.33% Traditional ROI: 3.65%
316 BURNSIDE ST #203 Annapolis, MD Just Reduced to 474k. Welcome to the sought-after Newport Condominiums in Eastport, where ...	1 beds \| 1 baths \| N/A	$474,000	Airbnb cash on cash: -1.42% Traditional cash on cash: -0.01% Airbnb Rental Income: $1077 Traditional Rental Income: $1337 Airbnb ROI: -1.42% Traditional ROI: -0.01%
1915 TOWNE CENTRE Boulevard #915 Annapolis, MD Now priced at $729,900-reduced from $749,900-and including a $5,000 seller credit toward c...	2 beds \| 2 baths \| 1,616 sq.ft.	$729,900	Airbnb cash on cash: -3.22% Traditional cash on cash: -0.28% Airbnb Rental Income: $1082 Traditional Rental Income: $2710 Airbnb ROI: -3.22% Traditional ROI: -0.28%
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.	$699,900	Airbnb cash on cash: 0.56% Traditional cash on cash: 2.87% Airbnb Rental Income: $2057 Traditional Rental Income: $3030 Airbnb ROI: 0.56% Traditional ROI: 2.87%
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: -1.21% Traditional cash on cash: 0.68% Airbnb Rental Income: $1245 Traditional Rental Income: $3263 Airbnb ROI: -1.21% Traditional ROI: 0.68%
2568 GLEN Cove Annapolis, MD READ THIS!! NEXT WEEK: New Carpet to be installed upstairs as well as wallpaper removal an...	3 beds \| 3 baths \| 1,512 sq.ft.	$499,000	Airbnb cash on cash: -0.15% Traditional cash on cash: 3.24% Airbnb Rental Income: $1648 Traditional Rental Income: $2765 Airbnb ROI: -0.15% 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: -0.4% Traditional cash on cash: 0.57% Airbnb Rental Income: $1648 Traditional Rental Income: $2023 Airbnb ROI: -0.4% 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.	$612,999	Airbnb cash on cash: 0.45% Traditional cash on cash: 3.68% Airbnb Rental Income: $2057 Traditional Rental Income: $3378 Airbnb ROI: 0.45% Traditional ROI: 3.68%
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: -1.31% Traditional cash on cash: -0.29% Airbnb Rental Income: $2057 Traditional Rental Income: $3405 Airbnb ROI: -1.31% Traditional ROI: -0.29%

Real Estate investment in Annapolis, MD

There are 203 properties for sale in the city of Annapolis . The median list price in Annapolis is $665,000 and the average price per square foot is $284. In May 2026, the average monthly cash on cash return in Annapolis is 1.00%. The average monthly rental income in Annapolis is $2,415.

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

There are 203 investment properties available for sale in Annapolis.

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

The ROI for Long-Term is higher than the Short-Term in Annapolis with average rental income of $2,415.

Your search for investment property begins and ends here

Investment Property for Sale in Annapolis, MD

66 FRANKLIN ST #20

Annapolis, MD

1 beds | 2 baths | N/A

$725,000

Airbnb cash on cash: -2.71%

Traditional cash on cash: -0.43%

Airbnb Rental Income: $1077

Traditional Rental Income: $2248

Airbnb ROI: -2.71%

Traditional ROI: -0.43%

1231 VAN BUREN Drive

Annapolis, MD

3 beds | 2 baths | 1,694 sq.ft.

$635,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: 1.61%

Airbnb Rental Income: $1648

Traditional Rental Income: $2175

Airbnb ROI: -0.06%

Traditional ROI: 1.61%

7 SILVERWOOD Circle #3

Annapolis, MD

2 beds | 2 baths | N/A

$269,990

Airbnb cash on cash: -1.73%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $1082

Traditional Rental Income: $2020

Airbnb ROI: -1.73%

Traditional ROI: 3.4%

1107 BRASHEARS Street

Annapolis, MD

5 beds | 2 baths | 1,800 sq.ft.

$825,000

Airbnb cash on cash: -0.35%

Traditional cash on cash: 1.43%

Airbnb Rental Income: $1643

Traditional Rental Income: $2541

Airbnb ROI: -0.35%

Traditional ROI: 1.43%

1915 TOWNE CENTRE Boulevard #513

Annapolis, MD

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

$549,000

Airbnb cash on cash: -3.39%

Traditional cash on cash: 0.76%

Airbnb Rental Income: $1082

Traditional Rental Income: $2844

Airbnb ROI: -3.39%

Traditional ROI: 0.76%

349 EPPING WAY

Annapolis, MD

4 beds | 3 baths | N/A

$975,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: -1.39%

Airbnb Rental Income: $2057

Traditional Rental Income: $763

Airbnb ROI: -0.55%

Traditional ROI: -1.39%

3280 ARUNDEL ON THE BAY Road

Annapolis, MD

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

$824,900

Airbnb cash on cash: -0.45%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $1643

Traditional Rental Income: $4883

Airbnb ROI: -0.45%

Traditional ROI: 4.37%

1109 BOUCHER Avenue

Annapolis, MD

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

$1,345,000

Airbnb cash on cash: -0.87%

Traditional cash on cash: 1.8%

Airbnb Rental Income: $2057

Traditional Rental Income: $4864

Airbnb ROI: -0.87%