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
32 EAST Street Annapolis, MD	3 beds \| 3 baths \| 2,100 sq.ft.	$1,200,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 0.14% Airbnb Rental Income: $2680 Traditional Rental Income: $2245 Airbnb ROI: -0.04% Traditional ROI: 0.14%
1915 TOWNE CENTRE Boulevard unit: 807 #807 Annapolis, MD PRICE IMPROVEMENT!! COSMOPOLITAN 2BR/2BA CONDO in the GRANDVIEW at TOWNE CENTRE! Condo com...	2 beds \| 2 baths \| 1,246 sq.ft.	$545,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 3.06% Airbnb Rental Income: $2338 Traditional Rental Income: $2694 Airbnb ROI: 1.22% Traditional ROI: 3.06%
66 FRANKLIN ST #20 Annapolis, MD Chic Street-Level Condo in the Heart of Annapolis. Welcome to this spacious 1-bedroom, 1.5...	1 beds \| 2 baths \| N/A	$750,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 1.09% Airbnb Rental Income: $1744 Traditional Rental Income: $2248 Airbnb ROI: -0.32% Traditional ROI: 1.09%
2026 GOV THOMAS BLADEN Way unit: 102 #102 Annapolis, MD This 3 bed / 2 bath condo has everything you need a cozy fireplace, spacious layout, and n...	3 beds \| 2 baths \| 1,317 sq.ft.	$379,999	Airbnb cash on cash: 2.19% Traditional cash on cash: 2.97% Airbnb Rental Income: $2680 Traditional Rental Income: $2320 Airbnb ROI: 2.19% Traditional ROI: 2.97%
5 PARK Place unit: 107 #107 Annapolis, MD Enjoy luxury condo living in this first-floor 2-bedroom, 2-bath home. Featuring gleaming h...	2 beds \| 2 baths \| 1,272 sq.ft.	$625,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 2.1% Airbnb Rental Income: $2338 Traditional Rental Income: $2551 Airbnb ROI: 0.74% Traditional ROI: 2.1%
201 BOWIE Avenue Annapolis, MD Beautifully Updated Annapolis Home Near Navy Stadium!! Welcome to 201 Bowie Ave, a turnkey...	4 beds \| 3 baths \| 1,709 sq.ft.	$584,900	Airbnb cash on cash: 2.28% Traditional cash on cash: 3.14% Airbnb Rental Income: $3104 Traditional Rental Income: $2866 Airbnb ROI: 2.28% Traditional ROI: 3.14%
52 PRIMROSE HILL Lane Annapolis, MD Welcome to 52 Primrose Hill Lane - the original model home in Craftmark's Primrose Hill co...	5 beds \| 5 baths \| 3,978 sq.ft.	$949,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 3.31% Airbnb Rental Income: $3871 Traditional Rental Income: $5022 Airbnb ROI: 1.06% Traditional ROI: 3.31%
1676 SAINT ALBANS SQ Annapolis, MD OFFER DEADLINE WEDNESDAY AT 10PM OCTOBER 22nd. Welcome to this stunning California-style e...	3 beds \| 4 baths \| N/A	$969,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 1.21% Airbnb Rental Income: $2680 Traditional Rental Income: $2881 Airbnb ROI: 0.29% Traditional ROI: 1.21%
27 DORSEY AVE Annapolis, MD Step into this beautifully renovated Annapolis charmer - completely updated from the groun...	2 beds \| 1 baths \| N/A	$349,900	Airbnb cash on cash: 3.01% Traditional cash on cash: 2.34% Airbnb Rental Income: $2338 Traditional Rental Income: $1538 Airbnb ROI: 3.01% Traditional ROI: 2.34%
3182 HARNESS CREEK Road Annapolis, MD Incredible value for this newly completed waterfront estate - now offered at $10,250,000. ...	4 beds \| 6 baths \| 5,375 sq.ft.	$10,250,000	Airbnb cash on cash: -0.9% Traditional cash on cash: -0.35% Airbnb Rental Income: $3104 Traditional Rental Income: $7639 Airbnb ROI: -0.9% Traditional ROI: -0.35%
215 CHESTER Avenue Annapolis, MD Embrace the Eastport lifestyle in this charming craftsman just steps from the water and do...	4 beds \| 4 baths \| 3,421 sq.ft.	$1,950,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 0.25% Airbnb Rental Income: $3104 Traditional Rental Income: $3908 Airbnb ROI: -0.59% Traditional ROI: 0.25%
103 NORMA Alley Annapolis, MD OPEN HOUSE Sunday 2-4PM Please join us to see this beautiful and updated townhome located ...	4 beds \| 5 baths \| 1,880 sq.ft.	$695,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 3.17% Airbnb Rental Income: $3104 Traditional Rental Income: $3727 Airbnb ROI: 1.12% Traditional ROI: 3.17%
66 FRANKLIN Street unit: 509 #509 Annapolis, MD Gorgeous, One-of-a-Kind Luxury Penthouse in Downtown Annapolis! Welcome to this stunning 3...	3 beds \| 4 baths \| 2,477 sq.ft.	$1,850,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 0.05% Airbnb Rental Income: $2680 Traditional Rental Income: $3393 Airbnb ROI: -0.73% Traditional ROI: 0.05%
1071 CEDAR RIDGE COURT Annapolis, MD Nestled in the Cedar Ridge community, this contemporary end-of-row townhouse offers a perf...	3 beds \| 3 baths \| 1,320 sq.ft.	$395,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 3.73% Airbnb Rental Income: $2680 Traditional Rental Income: $2469 Airbnb ROI: 2.58% Traditional ROI: 3.73%
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 \| N/A	$975,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 1.07% Airbnb Rental Income: $2338 Traditional Rental Income: $2737 Airbnb ROI: -0.01% Traditional ROI: 1.07%
633 BAYSTONE CT Annapolis, MD Price just reduced! Also for Rent for $3000/Mo. Welcome to easy living on the Broadneck P...	3 beds \| 2 baths \| N/A	$439,900	Airbnb cash on cash: 2.8% Traditional cash on cash: 4.43% Airbnb Rental Income: $2680 Traditional Rental Income: $2717 Airbnb ROI: 2.8% Traditional ROI: 4.43%
39 WINDWHISPER Lane Annapolis, MD RARE OPPORTUNITY TO BUY A WATERFRONT PROPERTY IN ANNAPOLIS AT THIS PRICE POINT! LOCATED ON...	3 beds \| 4 baths \| 3,193 sq.ft.	$685,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 2.96% Airbnb Rental Income: $2680 Traditional Rental Income: $3397 Airbnb ROI: 0.84% Traditional ROI: 2.96%
1909 ELEANOR Court Annapolis, MD Welcome to 1909 Eleanor Ct, a stunning colonial featuring five bedrooms and three and a ha...	5 beds \| 4 baths \| 4,790 sq.ft.	$975,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 2.16% Airbnb Rental Income: $3871 Traditional Rental Income: $3869 Airbnb ROI: 1.24% Traditional ROI: 2.16%
141 WEST ST #403 Annapolis, MD In the heart of Downtown Annapolis Art District, this Rare, LUXURY PENTHOUSE captures the ...	3 beds \| 3 baths \| N/A	$1,375,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 0.28% Airbnb Rental Income: $2680 Traditional Rental Income: $3160 Airbnb ROI: -0.59% Traditional ROI: 0.28%
1553 STAR PINE Drive Annapolis, MD Welcome to your new home in Whispering Woods! This charming duplex offers practical living...	2 beds \| 2 baths \| 1,060 sq.ft.	$346,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 4.37% Airbnb Rental Income: $2338 Traditional Rental Income: $2165 Airbnb ROI: 3.12% Traditional ROI: 4.37%
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 \| N/A	$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%
944 YACHTSMAN Way Annapolis, MD Buyer backed out last minute - their mistake is your opportunity!! It went quickly last ti...	2 beds \| 2 baths \| 1,354 sq.ft.	$445,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 3.56% Airbnb Rental Income: $2338 Traditional Rental Income: $2455 Airbnb ROI: 1.89% Traditional ROI: 3.56%
122 WATERLINE Court Annapolis, MD Elegant and refined, this home is the upscale Annapolis residence you've been dreaming of!...	4 beds \| 5 baths \| 2,450 sq.ft.	$615,000	Airbnb cash on cash: 1.83% Traditional cash on cash: 3.54% Airbnb Rental Income: $3104 Traditional Rental Income: $3381 Airbnb ROI: 1.83% Traditional ROI: 3.54%
547 LEFTWICH LN #88 Annapolis, MD PRiCE IMPROVEMENT! COSMOPOLITAN ANNAPOLIS TOWNHOME BOASTING SKYLINE ROOFTOP DECK! ADMIRAL...	3 beds \| 3 baths \| N/A	$575,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 3.37% Airbnb Rental Income: $2680 Traditional Rental Income: $2973 Airbnb ROI: 1.64% Traditional ROI: 3.37%
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: 1.76% Airbnb Rental Income: $3104 Traditional Rental Income: $3381 Airbnb ROI: 0.65% Traditional ROI: 1.76%
2900 SHIPMASTER Way unit: 211 #211 Annapolis, MD Welcome to your Annapolis retreat-Unit #211 is a bright and breezy 2-bedroom, 2-bath condo...	2 beds \| 2 baths \| 1,154 sq.ft.	$349,900	Airbnb cash on cash: 2.94% Traditional cash on cash: 4.17% Airbnb Rental Income: $2338 Traditional Rental Income: $2162 Airbnb ROI: 2.94% Traditional ROI: 4.17%
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.	$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%
2570 RIVA RD #3C Annapolis, MD Tidy ground-floor unit, close to restaurants, grocery stores, and businesses. Tons of plac...	1 beds \| 1 baths \| N/A	$245,000	Airbnb cash on cash: 3.22% Traditional cash on cash: 5.71% Airbnb Rental Income: $1744 Traditional Rental Income: $1840 Airbnb ROI: 3.22% Traditional ROI: 5.71%
1011 HYDE PARK DR Annapolis, MD This updated home offers 3 bedrooms and 2 full baths, with flexible living spaces througho...	3 beds \| 2 baths \| N/A	$575,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 2.39% Airbnb Rental Income: $2680 Traditional Rental Income: $2432 Airbnb ROI: 1.66% Traditional ROI: 2.39%
932 RIVERSEDGE CIR Annapolis, MD Welcome to 932 Riversedge Circle - a beautifully updated, one-level end-unit townhome in d...	2 beds \| 1 baths \| N/A	$399,000	Airbnb cash on cash: 2.63% Traditional cash on cash: 1.67% Airbnb Rental Income: $2338 Traditional Rental Income: $1398 Airbnb ROI: 2.63% Traditional ROI: 1.67%
5 PARK Place unit: 428 #428 Annapolis, MD Experience luxury and light in this rare 3-bedroom, 2.5-bath condo in the highly sought-af...	3 beds \| 3 baths \| 1,822 sq.ft.	$935,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 0.83% Airbnb Rental Income: $2680 Traditional Rental Income: $2797 Airbnb ROI: -0.04% Traditional ROI: 0.83%
304-G HILLTOP Lane 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.	$299,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 5.11% Airbnb Rental Income: $2338 Traditional Rental Income: $2116 Airbnb ROI: 3.84% Traditional ROI: 5.11%
25 DORSEY Avenue Annapolis, MD Modern Cape Cod style home located near everything Annapolis has to offer! It's just minut...	4 beds \| 3 baths \| 1,820 sq.ft.	$515,000	Airbnb cash on cash: 2.92% Traditional cash on cash: 6.74% Airbnb Rental Income: $3104 Traditional Rental Income: $4234 Airbnb ROI: 2.92% Traditional ROI: 6.74%
1411 STONECREEK RD Annapolis, MD Price Reduction to under $550K!! Open House Saturday 10/26/25 12-2 pm. Perfect single fami...	4 beds \| 4 baths \| N/A	$549,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 5.09% Airbnb Rental Income: $3104 Traditional Rental Income: $3771 Airbnb ROI: 2.41% Traditional ROI: 5.09%
1003 OLD BAY RIDGE Road Annapolis, MD You simply will not find a more detailed, custom-renovated home at this price point anywhe...	3 beds \| 4 baths \| 2,877 sq.ft.	$775,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 1.96% Airbnb Rental Income: $2680 Traditional Rental Income: $2896 Airbnb ROI: 0.78% Traditional ROI: 1.96%
948 YACHTSMAN WAY Annapolis, MD Open House cancelled New Price! $468,000 This lovely 3 bed, 2.5 bath Duplex is picture ...	3 beds \| 3 baths \| N/A	$468,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 3.85% Airbnb Rental Income: $2680 Traditional Rental Income: $2655 Airbnb ROI: 2.46% Traditional ROI: 3.85%
2707 JUDSON Place Annapolis, MD Welcome to 2707 Judson Place in Riva Woods. This inviting home sits on a private, fenced c...	3 beds \| 3 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 Street Annapolis, MD Incredible West Annapolis home that has been renovated from top to bottom with high end fi...	3 beds \| 3 baths \| 1,869 sq.ft.	$1,175,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 1% Airbnb Rental Income: $2680 Traditional Rental Income: $3155 Airbnb ROI: -0.02% Traditional ROI: 1%
198 CLAY Street Annapolis, MD Welcome to 198 Clay Street in the heart of Annapolis! This charming row home offers water ...	2 beds \| 2 baths \| 902 sq.ft.	$429,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 3.14% Airbnb Rental Income: $2338 Traditional Rental Income: $2021 Airbnb ROI: 2.49% Traditional ROI: 3.14%
919 BERWICK Drive Annapolis, MD Welcome to this exquisite home nestled conveniently close to downtown Annapolis and Eastpo...	4 beds \| 3 baths \| 2,292 sq.ft.	$799,900	Airbnb cash on cash: 1.18% Traditional cash on cash: 3.1% Airbnb Rental Income: $3104 Traditional Rental Income: $3829 Airbnb ROI: 1.18% Traditional ROI: 3.1%

Real Estate investment in Annapolis, MD

There are 232 properties for sale in the city of Annapolis . The median list price in Annapolis is $699,000 and the average price per square foot is $273. In November 2025, the average monthly cash on cash return in Annapolis is 2.00%. The average monthly rental income in Annapolis is $2,764.

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

There are 232 investment properties available for sale in Annapolis.

In 2025, 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 $2,764.

Your search for investment property begins and ends here

Investment Property for Sale in Annapolis, MD

32 EAST Street

Annapolis, MD

3 beds | 3 baths | 2,100 sq.ft.

$1,200,000

Airbnb cash on cash: -0.04%

Traditional cash on cash: 0.14%

Airbnb Rental Income: $2680

Traditional Rental Income: $2245

Airbnb ROI: -0.04%

Traditional ROI: 0.14%

1915 TOWNE CENTRE Boulevard unit: 807 #807

Annapolis, MD

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

$545,000

Airbnb cash on cash: 1.22%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $2338

Traditional Rental Income: $2694

Airbnb ROI: 1.22%

Traditional ROI: 3.06%

66 FRANKLIN ST #20

Annapolis, MD

1 beds | 2 baths | N/A

$750,000

Airbnb cash on cash: -0.32%

Traditional cash on cash: 1.09%

Airbnb Rental Income: $1744

Traditional Rental Income: $2248

Airbnb ROI: -0.32%

Traditional ROI: 1.09%

2026 GOV THOMAS BLADEN Way unit: 102 #102

Annapolis, MD

3 beds | 2 baths | 1,317 sq.ft.

$379,999

Airbnb cash on cash: 2.19%

Traditional cash on cash: 2.97%

Airbnb Rental Income: $2680

Traditional Rental Income: $2320

Airbnb ROI: 2.19%

Traditional ROI: 2.97%

5 PARK Place unit: 107 #107

Annapolis, MD

2 beds | 2 baths | 1,272 sq.ft.

$625,000

Airbnb cash on cash: 0.74%

Traditional cash on cash: 2.1%

Airbnb Rental Income: $2338

Traditional Rental Income: $2551

Airbnb ROI: 0.74%

Traditional ROI: 2.1%

201 BOWIE Avenue

Annapolis, MD

4 beds | 3 baths | 1,709 sq.ft.

$584,900

Airbnb cash on cash: 2.28%

Traditional cash on cash: 3.14%

Airbnb Rental Income: $3104

Traditional Rental Income: $2866

Airbnb ROI: 2.28%

Traditional ROI: 3.14%

52 PRIMROSE HILL Lane

Annapolis, MD

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

$949,000

Airbnb cash on cash: 1.06%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $3871

Traditional Rental Income: $5022

Airbnb ROI: 1.06%

Traditional ROI: 3.31%

1676 SAINT ALBANS SQ

Annapolis, MD

3 beds | 4 baths | N/A

$969,000

Airbnb cash on cash: 0.29%

Traditional cash on cash: 1.21%

Airbnb Rental Income: $2680

Traditional Rental Income: $2881

Airbnb ROI: 0.29%