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 48 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
1394 STONECREEK RD Annapolis, MD Offer has been received and we have set an offer deadline of 3 PM on Tuesday 1/14 for the ...	4 beds \| 4 baths \| N/A	$585,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 2.85% Airbnb Rental Income: $3104 Traditional Rental Income: $2779 Airbnb ROI: 2.15% Traditional ROI: 2.85%
1213 Mckinley St Annapolis, MD Here's your chance to live in the Heart of Eastport! Cute cape cod with new kitchen and re...	3 beds \| 1 baths \| 1,008 sq.ft.	$449,000	Airbnb cash on cash: 2.93% Traditional cash on cash: 2.42% Airbnb Rental Income: $2680 Traditional Rental Income: $1833 Airbnb ROI: 2.93% Traditional ROI: 2.42%
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%
900 COACHWAY Annapolis, MD MID-CENTURY MODERN HOME IN THE DOWNS ON THE SEVERN! ALL OFFERS DUE AT 8PM SUNDAY 1/25/26. ...	3 beds \| 3 baths \| N/A	$824,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 1.23% Airbnb Rental Income: $2680 Traditional Rental Income: $2635 Airbnb ROI: 0.46% Traditional ROI: 1.23%
1909 Eleanor Ct Annapolis, MD Welcome to 1909 Eleanor Ct, a stunning colonial featuring five bedrooms and three and a ha...	5 beds \| 3 baths \| 4,790 sq.ft.	$950,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 2.23% Airbnb Rental Income: $3871 Traditional Rental Income: $3869 Airbnb ROI: 1.29% Traditional ROI: 2.23%
847 WOODMONT RD Annapolis, MD Welcome Home to Comfort, Convenience & Community Living This well-maintained 2-bedroom, 2...	2 beds \| 2 baths \| N/A	$689,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 1.37% Airbnb Rental Income: $2338 Traditional Rental Income: $2163 Airbnb ROI: 0.74% Traditional ROI: 1.37%
1525 Hickory Wood Dr Annapolis, MD This colonial style split foyer offers privacy & many major updates! Perfectly located in ...	3 beds \| 2 baths \| 1,265 sq.ft.	$445,000	Airbnb cash on cash: 2.9% Traditional cash on cash: 3.19% Airbnb Rental Income: $2680 Traditional Rental Income: $2167 Airbnb ROI: 2.9% Traditional ROI: 3.19%
406 Harbor Dr Annapolis, MD Welcome to 406 Harbor Drive, an exceptional residence in the heart of Hillsmere Shores, on...	4 beds \| 3 baths \| 4,000 sq.ft.	$795,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 2.11% Airbnb Rental Income: $3104 Traditional Rental Income: $3202 Airbnb ROI: 1.03% Traditional ROI: 2.11%
2707 Judson Pl Annapolis, MD Welcome to 2707 Judson Place in Riva Woods. This inviting home sits on a private, fenced c...	3 beds \| 2 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 St Annapolis, MD 30K Price Improvement! Seller motivated! Incredible West Annapolis home that has been reno...	3 beds \| 2 baths \| 1,869 sq.ft.	$1,115,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 1.05% Airbnb Rental Income: $2680 Traditional Rental Income: $3155 Airbnb ROI: 0.01% Traditional ROI: 1.05%
106 Stilly Way Annapolis, MD This stunning home is move-in ready and boasts high-end upgrades throughout. It features a...	4 beds \| 4 baths \| 4,594 sq.ft.	$983,540	Airbnb cash on cash: 1.25% Traditional cash on cash: 3.75% Airbnb Rental Income: $3104 Traditional Rental Income: $4686 Airbnb ROI: 1.25% Traditional ROI: 3.75%
143 Stilly Way Annapolis, MD May Delivery! This brand-new home is the perfect match for all of your family's needs! Thi...	6 beds \| 4 baths \| 5,370 sq.ft.	$1,199,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 3.43% Airbnb Rental Income: $3871 Traditional Rental Income: $5652 Airbnb ROI: 1.26% Traditional ROI: 3.43%
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%
1141 MAINSAIL DR Annapolis, MD PRICE ADJUSTED on this wonderful 4-bedroom home! Welcome to one of Annapolis' most sought-...	4 beds \| 3 baths \| N/A	$890,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 2.15% Airbnb Rental Income: $3104 Traditional Rental Income: $3431 Airbnb ROI: 0.9% Traditional ROI: 2.15%
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%
111 Janwall St Annapolis, MD SELLER IS OFFERING $10,000 SETTLEMENT HELP! This beautiful home is ideally situated in a q...	3 beds \| 2 baths \| 1,754 sq.ft.	$599,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 3.27% Airbnb Rental Income: $2680 Traditional Rental Income: $2979 Airbnb ROI: 1.6% Traditional ROI: 3.27%
Lynnfield Plan Annapolis, MD	4 beds \| 3 baths \| 4,213 sq.ft.	$1,034,990	Airbnb cash on cash: 0.31% Traditional cash on cash: 0.65% Airbnb Rental Income: $3104 Traditional Rental Income: $2723 Airbnb ROI: 0.31% Traditional ROI: 0.65%
Kensington Plan Annapolis, MD	4 beds \| 4 baths \| 4,245 sq.ft.	$1,059,990	Airbnb cash on cash: 0.25% Traditional cash on cash: 0.99% Airbnb Rental Income: $3104 Traditional Rental Income: $3120 Airbnb ROI: 0.25% Traditional ROI: 0.99%
513 Horn Point Dr Annapolis, MD Exceptional Waterfront and Beachfront living on Horn Point in coveted Eastport. Launch you...	4 beds \| 3 baths \| 3,186 sq.ft.	$3,500,000	Airbnb cash on cash: -0.97% Traditional cash on cash: -0.61% Airbnb Rental Income: $3104 Traditional Rental Income: $3593 Airbnb ROI: -0.97% Traditional ROI: -0.61%
1814 PLEASANT PLAINS RD Annapolis, MD RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO...	5 beds \| 2 baths \| N/A	$1,300,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 0.32% Airbnb Rental Income: $3871 Traditional Rental Income: $3002 Airbnb ROI: 0.35% Traditional ROI: 0.32%
1814 & 1836 PLEASANT PLAINS & CHERRY RD Annapolis, MD RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO...	5 beds \| 2 baths \| N/A	$1,300,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 0.46% Airbnb Rental Income: $3871 Traditional Rental Income: $2971 Airbnb ROI: 0.52% Traditional ROI: 0.46%
1207 Mcguckian St Annapolis, MD Don't miss this stunning new construction in the highly desirable Homewood neighborhood of...	4 beds \| 3 baths \| 3,150 sq.ft.	$1,395,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 1.72% Airbnb Rental Income: $3104 Traditional Rental Income: $3642 Airbnb ROI: 0.76% Traditional ROI: 1.72%
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%
320 Chester Ave Annapolis, MD Rare opportunity to own a charming 2-unit building in the heart of Eastport, offering wate...	2 beds \| 2 baths \| 1,176 sq.ft.	$750,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 0.29% Airbnb Rental Income: $2338 Traditional Rental Income: $1892 Airbnb ROI: 0.1% Traditional ROI: 0.29%
3109 Ervin Ct Annapolis, MD 3109 Ervin Ct, Annapolis, MD 21403 \| Single Family Residential	2 beds \| 2 baths \| 1,801 sq.ft.	$849,900	Airbnb cash on cash: -0.01% Traditional cash on cash: 0.62% Airbnb Rental Income: $2338 Traditional Rental Income: $2259 Airbnb ROI: -0.01% Traditional ROI: 0.62%
2 Southgate Ave #10 Annapolis, MD 2 Southgate Ave #10, Annapolis, MD 21401 \| Single Family Residential	3 beds \| 2 baths \| 3,884 sq.ft.	$1,975,000	Airbnb cash on cash: -1.12% Traditional cash on cash: -1.21% Airbnb Rental Income: $2680 Traditional Rental Income: $1890 Airbnb ROI: -1.12% Traditional ROI: -1.21%
39 Southgate Ave Annapolis, MD 39 Southgate Ave, Annapolis, MD 21401 \| Single Family Residential	5 beds \| 3 baths \| 6,789 sq.ft.	$3,750,000	Airbnb cash on cash: -1.24% Traditional cash on cash: -1.19% Airbnb Rental Income: $3871 Traditional Rental Income: $3213 Airbnb ROI: -1.24% Traditional ROI: -1.19%
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%
621 Wood Lot Trail Rd Annapolis, MD 621 Wood Lot Trail Rd, CROWNSVILLE, MD 21401 \| Single Family Residential	5 beds \| 3 baths \| 3,970 sq.ft.	$884,999	Airbnb cash on cash: 1.43% Traditional cash on cash: 1.36% Airbnb Rental Income: $3871 Traditional Rental Income: $2979 Airbnb ROI: 1.43% Traditional ROI: 1.36%
200 Chesapeake Ave Annapolis, MD *** A must-see opportunity in the desirable Eastport Peninsula! This unique property featu...	2 beds \| 1 baths \| 2,942 sq.ft.	$1,099,000	Airbnb cash on cash: -0.31% Traditional cash on cash: -0.91% Airbnb Rental Income: $2338 Traditional Rental Income: $1144 Airbnb ROI: -0.31% Traditional ROI: -0.91%
1800 SEVERN GROVE RD Annapolis, MD Nestled in the serene Dellwood community, this contemporary gem offers an exclusive lifest...	3 beds \| 3 baths \| N/A	$967,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 1.17% Airbnb Rental Income: $2680 Traditional Rental Income: $2912 Airbnb ROI: 0.21% Traditional ROI: 1.17%
1031 OLD BAY RIDGE RD Annapolis, MD Discover an exquisite blend of luxury and comfort in this stunning split foyer home, nestl...	4 beds \| 3 baths \| N/A	$739,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 2.28% Airbnb Rental Income: $3104 Traditional Rental Income: $2877 Airbnb ROI: 1.59% Traditional ROI: 2.28%
2572 Golfers Ridge Rd Annapolis, MD Heritage Harbour - A Premier 55+ Community! Enjoy active adult living with abundant amenit...	3 beds \| 2 baths \| 1,994 sq.ft.	$690,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 1.9% Airbnb Rental Income: $2680 Traditional Rental Income: $2691 Airbnb ROI: 0.9% Traditional ROI: 1.9%
1091 Skyway Dr Annapolis, MD 1091 Skyway Dr, Annapolis, MD 21409 \| Single Family Residential	4 beds \| 3 baths \| 2,360 sq.ft.	$625,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 2.27% Airbnb Rental Income: $3104 Traditional Rental Income: $2635 Airbnb ROI: 1.87% Traditional ROI: 2.27%
1753 EBLING TRL Annapolis, MD This exceptional residence is nestled in the exclusive, gated and water-privileged enclave...	3 beds \| 4 baths \| N/A	$1,100,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 0.66% Airbnb Rental Income: $2680 Traditional Rental Income: $2530 Airbnb ROI: 0.19% Traditional ROI: 0.66%
3 Victor Pkwy Annapolis, MD Schedule your appt today to tour this Charming Ranch style home located in the Victor Have...	2 beds \| 1 baths \| 886 sq.ft.	$330,000	Airbnb cash on cash: 3.13% Traditional cash on cash: 1.97% Airbnb Rental Income: $2338 Traditional Rental Income: $1400 Airbnb ROI: 3.13% Traditional ROI: 1.97%

Your search for investment property begins and ends here

Single Family Homes for Sale in Annapolis, MD

1394 STONECREEK RD

Annapolis, MD

4 beds | 4 baths | N/A

$585,000

Airbnb cash on cash: 2.15%

Traditional cash on cash: 2.85%

Airbnb Rental Income: $3104

Traditional Rental Income: $2779

Airbnb ROI: 2.15%

Traditional ROI: 2.85%

1213 Mckinley St

Annapolis, MD

3 beds | 1 baths | 1,008 sq.ft.

$449,000

Airbnb cash on cash: 2.93%

Traditional cash on cash: 2.42%

Airbnb Rental Income: $2680

Traditional Rental Income: $1833

Airbnb ROI: 2.93%

Traditional ROI: 2.42%

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%

900 COACHWAY

Annapolis, MD

3 beds | 3 baths | N/A

$824,000

Airbnb cash on cash: 0.46%

Traditional cash on cash: 1.23%

Airbnb Rental Income: $2680

Traditional Rental Income: $2635

Airbnb ROI: 0.46%

Traditional ROI: 1.23%

1909 Eleanor Ct

Annapolis, MD

5 beds | 3 baths | 4,790 sq.ft.

$950,000

Airbnb cash on cash: 1.29%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $3871

Traditional Rental Income: $3869

Airbnb ROI: 1.29%

Traditional ROI: 2.23%

847 WOODMONT RD

Annapolis, MD

2 beds | 2 baths | N/A

$689,000

Airbnb cash on cash: 0.74%

Traditional cash on cash: 1.37%

Airbnb Rental Income: $2338

Traditional Rental Income: $2163

Airbnb ROI: 0.74%

Traditional ROI: 1.37%

1525 Hickory Wood Dr

Annapolis, MD

3 beds | 2 baths | 1,265 sq.ft.

$445,000

Airbnb cash on cash: 2.9%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $2680

Traditional Rental Income: $2167

Airbnb ROI: 2.9%

Traditional ROI: 3.19%

406 Harbor Dr

Annapolis, MD

4 beds | 3 baths | 4,000 sq.ft.

$795,000

Airbnb cash on cash: 1.03%

Traditional cash on cash: 2.11%

Airbnb Rental Income: $3104

Traditional Rental Income: $3202

Airbnb ROI: 1.03%