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 56 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
1 Shipwright Hbr Annapolis, MD Reduced & priced below 3/10/2018 appraisal! One of the finest homes on Spa Creek located o...	3 beds \| 3 baths \| 3,108 sq.ft.	$5,898,000	Airbnb cash on cash: -1.01% Traditional cash on cash: -0.85% Airbnb Rental Income: $2680 Traditional Rental Income: $2942 Airbnb ROI: -1.01% Traditional ROI: -0.85%
819 Janice Dr Annapolis, MD Beautiful Colonial-Under Construction*9 ft ceilings & Hardwood flrs- Main level 2 Story ...	4 beds \| 3 baths \| 4,043 sq.ft.	$1,195,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 0.28% Airbnb Rental Income: $3104 Traditional Rental Income: $2722 Airbnb ROI: -0.01% Traditional ROI: 0.28%
113 Bay Dr Annapolis, MD Stunning Chesapeake Bay views in desirable Bay Ridge neighborhood. Water view home, open f...	3 beds \| 2 baths \| 2,286 sq.ft.	$3,300,000	Airbnb cash on cash: -0.76% Traditional cash on cash: -0.66% Airbnb Rental Income: $2680 Traditional Rental Income: $2358 Airbnb ROI: -0.76% Traditional ROI: -0.66%
1873 LUCE CREEK DR Annapolis, MD OPEN SATURDAY AND SUNDAY, FEB 28/MAR 1, 12:00-2:00! This one is a gem! Welcome to this abs...	5 beds \| 3 baths \| N/A	$815,000	Airbnb cash on cash: 2.14% Traditional cash on cash: N/A Airbnb Rental Income: $3871 Traditional Rental Income: $0 Airbnb ROI: 2.14% Traditional ROI: N/A
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: -0.89% Airbnb Rental Income: $2680 Traditional Rental Income: $2887 Airbnb ROI: -1.15% Traditional ROI: -0.89%
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.	$570,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 3.41% Airbnb Rental Income: $3871 Traditional Rental Income: $2932 Airbnb ROI: 3.61% Traditional ROI: 3.41%
4 Shiley St Annapolis, MD Here's the West Annapolis unicorn property that you've been waiting for! A VERY RARE TRIPL...	5 beds \| 5 baths \| 5,312 sq.ft.	$3,285,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 0.06% Airbnb Rental Income: $3871 Traditional Rental Income: $4522 Airbnb ROI: -0.43% Traditional ROI: 0.06%
13 German St Annapolis, MD This charming fully renovated 3 level single family colonial home is located in sought aft...	5 beds \| 3 baths \| 2,590 sq.ft.	$1,170,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 1.53% Airbnb Rental Income: $3871 Traditional Rental Income: $3724 Airbnb ROI: 0.94% Traditional ROI: 1.53%
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%
703 Glendon Ave Annapolis, MD A brand-new home for the brand-new you. You've worked hard to get here-now you deserve a h...	5 beds \| 4 baths \| 4,116 sq.ft.	$2,750,000	Airbnb cash on cash: -0.21% Traditional cash on cash: -0.04% Airbnb Rental Income: $3871 Traditional Rental Income: $3468 Airbnb ROI: -0.21% Traditional ROI: -0.04%
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: 1.2% Traditional cash on cash: 1.62% Airbnb Rental Income: $3871 Traditional Rental Income: $3446 Airbnb ROI: 1.2% Traditional ROI: 1.62%
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%
2762 BON HAVEN Lane Annapolis, MD Welcome to this lovely, affordable waterfront ranch home and Chalet house w/wrap-around de...	4 beds \| 2 baths \| 1,809 sq.ft.	$1,150,000	Airbnb cash on cash: 0.1% Traditional cash on cash: -0.04% Airbnb Rental Income: $3104 Traditional Rental Income: $2251 Airbnb ROI: 0.1% Traditional ROI: -0.04%
856 St Edmonds Pl Annapolis, MD 856 St Edmonds Pl, Arnold, MD 21401 \| Single Family Residential	5 beds \| 4 baths \| 6,412 sq.ft.	$2,795,000	Airbnb cash on cash: -1% Traditional cash on cash: -0.88% Airbnb Rental Income: $3871 Traditional Rental Income: $3347 Airbnb ROI: -1% Traditional ROI: -0.88%
1707 Ritchie Hwy Annapolis, MD 1707 Ritchie Hwy, Arnold, MD 21409 \| Single Family Residential	5 beds \| 4 baths \| 4,796 sq.ft.	$1,325,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 0.49% Airbnb Rental Income: $3871 Traditional Rental Income: $3267 Airbnb ROI: 0.31% Traditional ROI: 0.49%
Admiral Plan Annapolis, MD	4 beds \| 4 baths \| 4,483 sq.ft.	$1,079,990	Airbnb cash on cash: 0.21% Traditional cash on cash: 0.93% Airbnb Rental Income: $3104 Traditional Rental Income: $3120 Airbnb ROI: 0.21% Traditional ROI: 0.93%
Fitzgerald Plan Annapolis, MD	4 beds \| 3 baths \| 4,336 sq.ft.	$1,064,990	Airbnb cash on cash: 0.24% Traditional cash on cash: 0.57% Airbnb Rental Income: $3104 Traditional Rental Income: $2723 Airbnb ROI: 0.24% Traditional ROI: 0.57%
411 Ridgely Ave Annapolis, MD 411 Ridgely Ave, Annapolis, MD 21401 \| Single Family Residential	4 beds \| 4 baths \| 5,950 sq.ft.	$3,950,000	Airbnb cash on cash: -1.46% Traditional cash on cash: -1.25% Airbnb Rental Income: $3104 Traditional Rental Income: $3143 Airbnb ROI: -1.46% Traditional ROI: -1.25%
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: 2.19% Traditional cash on cash: 3.22% Airbnb Rental Income: $2680 Traditional Rental Income: $2551 Airbnb ROI: 2.19% Traditional ROI: 3.22%
120 Chesapeake Ave Annapolis, MD 120 Chesapeake Ave, Annapolis, MD 21403 \| Single Family Residential	2 beds \| 2 baths \| 2,130 sq.ft.	$1,449,000	Airbnb cash on cash: -0.85% Traditional cash on cash: -0.66% Airbnb Rental Income: $2338 Traditional Rental Income: $2016 Airbnb ROI: -0.85% Traditional ROI: -0.66%
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: 2.33% Traditional cash on cash: 3.14% Airbnb Rental Income: $3104 Traditional Rental Income: $2850 Airbnb ROI: 2.33% Traditional ROI: 3.14%
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%
1930 SEVERN GROVE RD Annapolis, MD This inviting 3-bedroom, 2 full bath rancher will feel like home the moment you step insid...	3 beds \| 2 baths \| N/A	$530,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 2.87% Airbnb Rental Income: $2680 Traditional Rental Income: $2520 Airbnb ROI: 1.91% Traditional ROI: 2.87%
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: 1.81% Traditional cash on cash: N/A Airbnb Rental Income: $3871 Traditional Rental Income: $0 Airbnb ROI: 1.81% Traditional ROI: N/A
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: N/A Airbnb Rental Income: $3871 Traditional Rental Income: $0 Airbnb ROI: 7.38% Traditional ROI: N/A
1107 CRESTVIEW DR Annapolis, MD Located in the highly sought-after Cape St. Claire neighborhood - where life unfolds again...	4 beds \| 2 baths \| N/A	$565,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 3.16% Airbnb Rental Income: $3104 Traditional Rental Income: $2764 Airbnb ROI: 2.46% Traditional ROI: 3.16%
100 Carroll Dr Annapolis, MD 100 Carroll Dr, Annapolis, MD 21403 \| Single Family Residential	4 beds \| 2 baths \| 1,935 sq.ft.	$649,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 1.37% Airbnb Rental Income: $3104 Traditional Rental Income: $2348 Airbnb ROI: 1.45% Traditional ROI: 1.37%
1041 Skyview Dr Annapolis, MD 1041 Skyview Dr, Annapolis, MD 21409 \| Single Family Residential	4 beds \| 3 baths \| 1,960 sq.ft.	$584,900	Airbnb cash on cash: 2.14% Traditional cash on cash: 2.41% Airbnb Rental Income: $3104 Traditional Rental Income: $2550 Airbnb ROI: 2.14% Traditional ROI: 2.41%
2568 Forest Knl Annapolis, MD 2568 Forest Knl, Annapolis, MD 21401 \| Single Family Residential	3 beds \| 2 baths \| 1,798 sq.ft.	$699,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 0.7% Airbnb Rental Income: $2680 Traditional Rental Income: $2105 Airbnb ROI: 0.61% Traditional ROI: 0.7%
1349 Yorktown Rd Annapolis, MD 1349 Yorktown Rd, Annapolis, AR 21409 \| Single Family Residential	16 beds \| 6 baths \| 5,719 sq.ft.	$2,799,000	Airbnb cash on cash: -0.95% Traditional cash on cash: N/A Airbnb Rental Income: $3871 Traditional Rental Income: $0 Airbnb ROI: -0.95% Traditional ROI: N/A

Your search for investment property begins and ends here

Single Family Homes for Sale in Annapolis, MD

1 Shipwright Hbr

Annapolis, MD

3 beds | 3 baths | 3,108 sq.ft.

$5,898,000

Airbnb cash on cash: -1.01%

Traditional cash on cash: -0.85%

Airbnb Rental Income: $2680

Traditional Rental Income: $2942

Airbnb ROI: -1.01%

Traditional ROI: -0.85%

819 Janice Dr

Annapolis, MD

4 beds | 3 baths | 4,043 sq.ft.

$1,195,000

Airbnb cash on cash: -0.01%

Traditional cash on cash: 0.28%

Airbnb Rental Income: $3104

Traditional Rental Income: $2722

Airbnb ROI: -0.01%

Traditional ROI: 0.28%

113 Bay Dr

Annapolis, MD

3 beds | 2 baths | 2,286 sq.ft.

$3,300,000

Airbnb cash on cash: -0.76%

Traditional cash on cash: -0.66%

Airbnb Rental Income: $2680

Traditional Rental Income: $2358

Airbnb ROI: -0.76%

Traditional ROI: -0.66%

1873 LUCE CREEK DR

Annapolis, MD

5 beds | 3 baths | N/A

$815,000

Airbnb cash on cash: 2.14%

Traditional cash on cash: N/A

Airbnb Rental Income: $3871

Traditional Rental Income: $0

Airbnb ROI: 2.14%

Traditional ROI: N/A

9 Shipwright St

Annapolis, MD

3 beds | 2 baths | 2,621 sq.ft.

$3,495,000

Airbnb cash on cash: -1.15%

Traditional cash on cash: -0.89%

Airbnb Rental Income: $2680

Traditional Rental Income: $2887

Airbnb ROI: -1.15%

Traditional ROI: -0.89%

1002 TYLER Avenue

Annapolis, MD

5 beds | 2 baths | 1,920 sq.ft.

$570,000

Airbnb cash on cash: 3.61%

Traditional cash on cash: 3.41%

Airbnb Rental Income: $3871

Traditional Rental Income: $2932

Airbnb ROI: 3.61%

Traditional ROI: 3.41%

4 Shiley St

Annapolis, MD

5 beds | 5 baths | 5,312 sq.ft.

$3,285,000

Airbnb cash on cash: -0.43%

Traditional cash on cash: 0.06%

Airbnb Rental Income: $3871

Traditional Rental Income: $4522

Airbnb ROI: -0.43%

Traditional ROI: 0.06%

13 German St

Annapolis, MD

5 beds | 3 baths | 2,590 sq.ft.

$1,170,000

Airbnb cash on cash: 0.94%

Traditional cash on cash: 1.53%

Airbnb Rental Income: $3871

Traditional Rental Income: $3724

Airbnb ROI: 0.94%