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.

Single Family Homes for Sale in Annapolis, MD

Search for Single Family Residential for Sale in Annapolis, Maryland. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 43 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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%
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%
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%
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%
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%
143-A E LAKE DR Annapolis, MD Don't MISS this RARE OPPORTUNITY IN THE VERY POPULAR COMMUNITY OF BAY RIDGE. Make this Hom...	3 beds \| 3 baths \| N/A	$979,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 1.19% Airbnb Rental Income: $2680 Traditional Rental Income: $3106 Airbnb ROI: 0.03% Traditional ROI: 1.19%
179 GREEN ST Annapolis, MD Welcome to the heart of downtown Annapolis at 179 Green Street. This charming home blends ...	2 beds \| 2 baths \| N/A	$999,999	Airbnb cash on cash: -0.21% Traditional cash on cash: -0.04% Airbnb Rental Income: $2338 Traditional Rental Income: $1916 Airbnb ROI: -0.21% Traditional ROI: -0.04%
2706 JUDSON PL Annapolis, MD Welcome to 2706 Judson Place, an immaculate completely remodeled rancher nestled in the de...	4 beds \| 3 baths \| N/A	$569,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 4.23% Airbnb Rental Income: $3104 Traditional Rental Income: $3325 Airbnb ROI: 2.49% Traditional ROI: 4.23%
1106 MAINSAIL DR Annapolis, MD At last, the one you've been waiting for. A beautiful home in a waterfront community. Mo...	5 beds \| 3 baths \| N/A	$895,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 1.35% Airbnb Rental Income: $3871 Traditional Rental Income: $2863 Airbnb ROI: 1.56% Traditional ROI: 1.35%
3300 SHORE DR Annapolis, MD Stunning Waterfront Coastal Retreat on Oyster Creek with Breathtaking Sunsets! This except...	4 beds \| 4 baths \| N/A	$1,650,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 0.89% Airbnb Rental Income: $3104 Traditional Rental Income: $3874 Airbnb ROI: -0.07% Traditional ROI: 0.89%
553 CHOPTANK COVE CT Annapolis, MD Days on market reflects seller ability to show because of illness. English Tudor featuring...	5 beds \| 4 baths \| N/A	$1,050,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 1.63% Airbnb Rental Income: $3871 Traditional Rental Income: $3446 Airbnb ROI: 1.21% Traditional ROI: 1.63%
769 ROBINHOOD RD Annapolis, MD 769 Robinhood Road is one of the most desirable Waterfront properties in Sherwood Forest....	3 beds \| 2 baths \| N/A	$1,250,000	Airbnb cash on cash: -0.61% Traditional cash on cash: -0.01% Airbnb Rental Income: $2680 Traditional Rental Income: $2751 Airbnb ROI: -0.61% Traditional ROI: -0.01%
3365 ARUNDEL ON THE BAY Road Annapolis, MD New Price. Welcome Home!!! Beautiful Single Family Home, a peaceful retreat nestled in the...	3 beds \| 2 baths \| 1,232 sq.ft.	$515,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 3.3% Airbnb Rental Income: $2680 Traditional Rental Income: $2551 Airbnb ROI: 2.25% Traditional ROI: 3.3%
3130 STARBOARD DR Annapolis, MD Welcome to your dream home nestled in the sought after water privileged community of Ancho...	5 beds \| 3 baths \| N/A	$1,350,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 1.18% Airbnb Rental Income: $3871 Traditional Rental Income: $3607 Airbnb ROI: 0.73% Traditional ROI: 1.18%
1836 BURLEY LN Annapolis, MD With the ability to dock 5 boats on a beautifully protected cove on Burley Creek, with 10'...	3 beds \| 3 baths \| N/A	$1,695,000	Airbnb cash on cash: -0.61% Traditional cash on cash: -0.34% Airbnb Rental Income: $2680 Traditional Rental Income: $2471 Airbnb ROI: -0.61% Traditional ROI: -0.34%
1207 HAMPTON RD Annapolis, MD Welcome to this beautifully maintained four-bedroom, two-bath colonial in the highly sough...	4 beds \| 2 baths \| N/A	$575,000	Airbnb cash on cash: 2.47% Traditional cash on cash: 3.31% Airbnb Rental Income: $3104 Traditional Rental Income: $2850 Airbnb ROI: 2.47% Traditional ROI: 3.31%
167 PRINCE GEORGE ST Annapolis, MD OPEN HOUSE HAS BEEN MOVED TO SATURDAY JANUARY 24TH FROM 1-3 PM Situated on one of Historic...	2 beds \| 3 baths \| N/A	$875,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 0% Airbnb Rental Income: $2338 Traditional Rental Income: $1877 Airbnb ROI: -0.14% Traditional ROI: 0%
8 STEWART AVE Annapolis, MD Welcome to 8 Stewart Avenue, located on a rare double lot in the heart of downtown Murray ...	5 beds \| 5 baths \| N/A	$3,195,000	Airbnb cash on cash: -0.58% Traditional cash on cash: -0.49% Airbnb Rental Income: $3871 Traditional Rental Income: $3301 Airbnb ROI: -0.58% Traditional ROI: -0.49%
3029 SOLSTICE LN Annapolis, MD Welcome to 3029 Solstice Lane, located in the exclusive Riva Trace community of Annapolis,...	3 beds \| 2 baths \| N/A	$729,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 1% Airbnb Rental Income: $2680 Traditional Rental Income: $2123 Airbnb ROI: 0.89% Traditional ROI: 1%
1011 HANSON ST Annapolis, MD Freshly updated 4BR. 3BA home with a bright, open main level and great indoor/outdoor flow...	4 beds \| 3 baths \| N/A	$549,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 3.8% Airbnb Rental Income: $3104 Traditional Rental Income: $3122 Airbnb ROI: 2.39% Traditional ROI: 3.8%
4 BOXWOOD Road Annapolis, MD Located at the corner of Spa Road and Boxwood Drive, this property offers an excellent Ann...	3 beds \| 1 baths \| 1,152 sq.ft.	$389,900	Airbnb cash on cash: 3.26% Traditional cash on cash: 2.26% Airbnb Rental Income: $2680 Traditional Rental Income: $1680 Airbnb ROI: 3.26% Traditional ROI: 2.26%
148 JEFFERSON ST Annapolis, MD Perfectly positioned in Eastport, Annapolis, just moments from downtown, this brand-new ho...	5 beds \| 3 baths \| N/A	$925,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 2.05% Airbnb Rental Income: $3871 Traditional Rental Income: $3179 Airbnb ROI: 1.89% Traditional ROI: 2.05%
1029 SMITHVILLE ST Annapolis, MD This charming 5 bedroom, 2 bath Cape Cod is located in a community with quick and easy acc...	5 beds \| 2 baths \| N/A	$317,000	Airbnb cash on cash: 7.38% Traditional cash on cash: 6.71% Airbnb Rental Income: $3871 Traditional Rental Income: $2839 Airbnb ROI: 7.38% Traditional ROI: 6.71%
1406 BRETTON VIEW RD Annapolis, MD This beautifully maintained 3-bedroom, 3ÃÂ½-bath Colonial offers the perfect blend of cla...	3 beds \| 4 baths \| N/A	$699,900	Airbnb cash on cash: 1.08% Traditional cash on cash: 3% Airbnb Rental Income: $2680 Traditional Rental Income: $3295 Airbnb ROI: 1.08% Traditional ROI: 3%
25 LINCOLN PKWY Annapolis, MD Located just minutes from the shops, restaurants, and waterfront charm of downtown Annapol...	3 beds \| 2 baths \| N/A	$515,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 2.49% Airbnb Rental Income: $2680 Traditional Rental Income: $2295 Airbnb ROI: 1.97% Traditional ROI: 2.49%
103 ROSELAWN RD Annapolis, MD Discover the charm of this delightful ranch-style home nestled in the serene Primrose Acre...	3 beds \| 2 baths \| N/A	$380,000	Airbnb cash on cash: 3.62% Traditional cash on cash: 4.43% Airbnb Rental Income: $2680 Traditional Rental Income: $2334 Airbnb ROI: 3.62% Traditional ROI: 4.43%
1266 SEABRIGHT DR Annapolis, MD Welcome home to this three bedroom, two full bath split level home in sought after Cape St...	3 beds \| 2 baths \| N/A	$525,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 2.88% Airbnb Rental Income: $2680 Traditional Rental Income: $2421 Airbnb ROI: 2.11% Traditional ROI: 2.88%
1148 MERMAID DR Annapolis, MD Welcome to Atlantis on the Broadneck Peninsula! This beautifully maintained 4-bedroom, 3-...	4 beds \| 3 baths \| N/A	$597,000	Airbnb cash on cash: 2.13% Traditional cash on cash: 3.7% Airbnb Rental Income: $3104 Traditional Rental Income: $3276 Airbnb ROI: 2.13% Traditional ROI: 3.7%
46 Lafayette Ave Annapolis, MD 46 Lafayette Ave is a Murray Hill classic, a beautifully updated Craftsman four-square whe...	4 beds \| 2 baths \| 1,800 sq.ft.	$975,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 0.83% Airbnb Rental Income: $3104 Traditional Rental Income: $2740 Airbnb ROI: 0.46% Traditional ROI: 0.83%
730 Rosedale St Annapolis, MD 730 Rosedale St, Annapolis, MD 21401 \| Single Family Residential	3 beds \| 2 baths \| 1,280 sq.ft.	$595,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 1.46% Airbnb Rental Income: $2680 Traditional Rental Income: $2061 Airbnb ROI: 1.43% Traditional ROI: 1.46%
1407 Brenwoode Rd Annapolis, MD Welcome to 1407 Brenwoode Rd. This spacious 3-bedroom home (with potential 4th bedroom /bo...	3 beds \| 3 baths \| 2,390 sq.ft.	$575,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 2.65% Airbnb Rental Income: $2680 Traditional Rental Income: $2636 Airbnb ROI: 1.55% Traditional ROI: 2.65%

Your search for investment property begins and ends here

Single Family Homes 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%

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%

1014 WELLS Avenue

Annapolis, MD

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%

99 SUMMERFIELD Drive

Annapolis, MD

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%

163 PRINCE GEORGE ST

Annapolis, MD

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

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

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%

143-A E LAKE DR

Annapolis, MD

3 beds | 3 baths | N/A

$979,000

Airbnb cash on cash: 0.03%

Traditional cash on cash: 1.19%

Airbnb Rental Income: $2680

Traditional Rental Income: $3106

Airbnb ROI: 0.03%