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 60 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
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%
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: 2.13% Airbnb Rental Income: $3104 Traditional Rental Income: $3705 Airbnb ROI: 0.65% Traditional ROI: 2.13%
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%
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%
133 Lake View Dr Annapolis, MD 133 Lake View Dr, Annapolis, MD 21403 \| Single Family Residential	5 beds \| 5 baths \| 4,308 sq.ft.	$1,400,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 1.6% Airbnb Rental Income: $3871 Traditional Rental Income: $4883 Airbnb ROI: 0.18% Traditional ROI: 1.6%
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: 3.43% Airbnb Rental Income: $2680 Traditional Rental Income: $3954 Airbnb ROI: 0.78% Traditional ROI: 3.43%
730 CRISFIELD WAY Annapolis, MD Welcome to Kingsport , a water privileged community packed with beautiful homes and all th...	5 beds \| 5 baths \| N/A	$865,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 3.15% Airbnb Rental Income: $3871 Traditional Rental Income: $4276 Airbnb ROI: 1.62% Traditional ROI: 3.15%
1913 DULANEY Place Annapolis, MD The perfect blend of 1950s charm and modern Annapolis living, situated steps from the wate...	5 beds \| 2 baths \| 2,969 sq.ft.	$925,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 2.25% Airbnb Rental Income: $3871 Traditional Rental Income: $3595 Airbnb ROI: 1.61% Traditional ROI: 2.25%
179 GREEN ST Annapolis, MD Experience the Essence of Annapolis Charm at 179 Green Street Nestled in the heart of his...	2 beds \| 2 baths \| N/A	$1,175,000	Airbnb cash on cash: -0.32% Traditional cash on cash: -0.18% Airbnb Rental Income: $2338 Traditional Rental Income: $1916 Airbnb ROI: -0.32% Traditional ROI: -0.18%
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%
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%
2828 BERTH Court Annapolis, MD Charming Home in Heritage Harbour - 55+ Community Living at Its Finest! Welcome to this be...	2 beds \| 2 baths \| 1,434 sq.ft.	$500,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 2.84% Airbnb Rental Income: $2338 Traditional Rental Income: $2458 Airbnb ROI: 1.34% Traditional ROI: 2.84%
553 CHOPTANK COVE CT Annapolis, MD English Tudor featuring a stone front patio, covered front porch for nature lovers and bir...	5 beds \| 4 baths \| N/A	$1,077,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 1.57% Airbnb Rental Income: $3871 Traditional Rental Income: $3446 Airbnb ROI: 1.16% Traditional ROI: 1.57%
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%
2175 GLENCREST CIRCLE - GEORGETOWN MODEL Annapolis, MD Ameri-Star Homes, one of the area's premier homebuilders, is excited to be offering our sp...	3 beds \| 2 baths \| 1,757 sq.ft.	$799,990	Airbnb cash on cash: 0.53% Traditional cash on cash: 1.51% Airbnb Rental Income: $2680 Traditional Rental Income: $2775 Airbnb ROI: 0.53% Traditional ROI: 1.51%
192 Duke Of Gloucester Annapolis, MD 192 Duke Of Gloucester, Annapolis, MD 21401 \| Single Family Residential	6 beds \| 4 baths \| 3,415 sq.ft.	$2,100,000	Airbnb cash on cash: -0.57% Traditional cash on cash: -0.47% Airbnb Rental Income: $3871 Traditional Rental Income: $3245 Airbnb ROI: -0.57% Traditional ROI: -0.47%
1241 Cherry Tree Ln Annapolis, MD 1241 Cherry Tree Ln, Annapolis, MD 21403 \| Single Family Residential	4 beds \| 5 baths \| 6,428 sq.ft.	$2,675,000	Airbnb cash on cash: -1.26% Traditional cash on cash: -0.36% Airbnb Rental Income: $3104 Traditional Rental Income: $4627 Airbnb ROI: -1.26% Traditional ROI: -0.36%
1900 Carrollton Rd Annapolis, MD 1900 Carrollton Rd, Annapolis, MD 21409 \| Single Family Residential	7 beds \| 6 baths \| 12,200 sq.ft.	$8,995,000	Airbnb cash on cash: -1.73% Traditional cash on cash: -1.4% Airbnb Rental Income: $3871 Traditional Rental Income: $5816 Airbnb ROI: -1.73% Traditional ROI: -1.4%
Lynnfield Plan Annapolis, MD	4 beds \| 3 baths \| 4,213 sq.ft.	$974,990	Airbnb cash on cash: 0.46% Traditional cash on cash: 0.81% Airbnb Rental Income: $3104 Traditional Rental Income: $2723 Airbnb ROI: 0.46% Traditional ROI: 0.81%
Admiral Plan Annapolis, MD	4 beds \| 4 baths \| 4,483 sq.ft.	$1,034,990	Airbnb cash on cash: 0.31% Traditional cash on cash: 1.06% Airbnb Rental Income: $3104 Traditional Rental Income: $3120 Airbnb ROI: 0.31% Traditional ROI: 1.06%
Kensington Plan Annapolis, MD	4 beds \| 4 baths \| 4,245 sq.ft.	$999,990	Airbnb cash on cash: 0.39% Traditional cash on cash: 1.17% Airbnb Rental Income: $3104 Traditional Rental Income: $3120 Airbnb ROI: 0.39% Traditional ROI: 1.17%
Fitzgerald Plan Annapolis, MD	4 beds \| 3 baths \| 4,336 sq.ft.	$989,990	Airbnb cash on cash: 0.42% Traditional cash on cash: 0.77% Airbnb Rental Income: $3104 Traditional Rental Income: $2723 Airbnb ROI: 0.42% Traditional ROI: 0.77%
93 BAY DR Annapolis, MD ""NEW PRICE"": SPECTACULAR WATER VIEWS OF THE THE CHESPEAKE BAY! LOCATION LOCATION! Don't ...	3 beds \| 1 baths \| N/A	$2,750,000	Airbnb cash on cash: -0.88% Traditional cash on cash: -0.93% Airbnb Rental Income: $2680 Traditional Rental Income: $1900 Airbnb ROI: -0.88% Traditional ROI: -0.93%
341 DUBOIS RD Annapolis, MD Located on a picturesque tree-lined street in highly desirable Annapolis, MD, this propert...	3 beds \| 3 baths \| N/A	$475,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 10.96% Airbnb Rental Income: $2680 Traditional Rental Income: $5914 Airbnb ROI: 2.25% Traditional ROI: 10.96%
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%
1715 PORTERS HILL RD Annapolis, MD Ideally situated on the banks of Luce Creek with sweeping views down the Severn River, 171...	4 beds \| 6 baths \| N/A	$3,995,000	Airbnb cash on cash: -1.04% Traditional cash on cash: -0.72% Airbnb Rental Income: $3104 Traditional Rental Income: $3581 Airbnb ROI: -1.04% Traditional ROI: -0.72%
962 Old Annapolis Neck Rd Annapolis, MD 962 Old Annapolis Neck Rd, Annapolis, MD 21403 \| Single Family Residential	5 beds \| 4 baths \| 3,718 sq.ft.	$1,695,000	Airbnb cash on cash: -0.21% Traditional cash on cash: -0.05% Airbnb Rental Income: $3871 Traditional Rental Income: $3296 Airbnb ROI: -0.21% Traditional ROI: -0.05%
228 DUBOIS RD Annapolis, MD Welcome to 228 Dubois Road in Annapolis Maryland** Updated Cape Cod on .81 Acres in Annapo...	4 beds \| 3 baths \| N/A	$675,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 3.26% Airbnb Rental Income: $3104 Traditional Rental Income: $3176 Airbnb ROI: 2.03% Traditional ROI: 3.26%
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 \| N/A	$779,000	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%
98 PINE DR Annapolis, MD Coming soon in water priveledged community on the South River! Well maintained ranch styl...	3 beds \| 2 baths \| N/A	$550,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 1.08% Airbnb Rental Income: $2680 Traditional Rental Income: $1577 Airbnb ROI: 1.99% Traditional ROI: 1.08%
410 Fox Hollow Ln Annapolis, MD 410 Fox Hollow Ln, Annapolis, MD 21403 \| Single Family Residential	4 beds \| 3 baths \| 3,240 sq.ft.	$725,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 1.81% Airbnb Rental Income: $3104 Traditional Rental Income: $2823 Airbnb ROI: 1.18% Traditional ROI: 1.81%
1641 CANANARO DR Annapolis, MD Amazing Value in this well cared for Single Family Home in the Revel Downs Community. Arc...	2 beds \| 2 baths \| N/A	$399,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 2.41% Airbnb Rental Income: $2338 Traditional Rental Income: $1782 Airbnb ROI: 2.35% Traditional ROI: 2.41%
30 Decatur Ave Annapolis, MD 30 Decatur Ave, Annapolis, MD 21403 \| Single Family Residential	4 beds \| 2 baths \| 1,477 sq.ft.	$1,100,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 0.14% Airbnb Rental Income: $3104 Traditional Rental Income: $2372 Airbnb ROI: 0.17% Traditional ROI: 0.14%
2639 GREENBRIAR LN Annapolis, MD Custom-built, Private, Waterfront Retreat on Crab Creek off the South River. This gorgeou...	3 beds \| 3 baths \| N/A	$1,650,000	Airbnb cash on cash: -0.75% Traditional cash on cash: -0.81% Airbnb Rental Income: $2680 Traditional Rental Income: $1947 Airbnb ROI: -0.75% Traditional ROI: -0.81%
219 Wardour Dr Annapolis, MD 219 Wardour Dr, Annapolis, MD 21401 \| Single Family Residential	5 beds \| 6 baths \| 8,296 sq.ft.	$3,595,000	Airbnb cash on cash: -1.2% Traditional cash on cash: -0.35% Airbnb Rental Income: $3871 Traditional Rental Income: $5879 Airbnb ROI: -1.2% Traditional ROI: -0.35%
222 LOOKOUT LN Annapolis, MD SHOWINGS BEGIN FRIDAY 12 NOON. Welcome to Providence, one of the most sought-after water p...	5 beds \| 3 baths \| N/A	$1,350,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 1.02% Airbnb Rental Income: $3871 Traditional Rental Income: $3576 Airbnb ROI: 0.59% Traditional ROI: 1.02%

Your search for investment property begins and ends here

Single Family Homes for Sale in Annapolis, MD

27 DORSEY AVE

Annapolis, MD

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%

161 E BAY VIEW DR

Annapolis, MD

4 beds | 4 baths | N/A

$949,000

Airbnb cash on cash: 0.65%

Traditional cash on cash: 2.13%

Airbnb Rental Income: $3104

Traditional Rental Income: $3705

Airbnb ROI: 0.65%

Traditional ROI: 2.13%

1002 TYLER Avenue

Annapolis, MD

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%

1011 HYDE PARK DR

Annapolis, MD

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%

133 Lake View Dr

Annapolis, MD

5 beds | 5 baths | 4,308 sq.ft.

$1,400,000

Airbnb cash on cash: 0.18%

Traditional cash on cash: 1.6%

Airbnb Rental Income: $3871

Traditional Rental Income: $4883

Airbnb ROI: 0.18%

Traditional ROI: 1.6%

1411 STONECREEK RD

Annapolis, MD

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

3 beds | 4 baths | 2,877 sq.ft.

$775,000

Airbnb cash on cash: 0.78%

Traditional cash on cash: 3.43%

Airbnb Rental Income: $2680

Traditional Rental Income: $3954

Airbnb ROI: 0.78%

Traditional ROI: 3.43%

730 CRISFIELD WAY

Annapolis, MD

5 beds | 5 baths | N/A

$865,000

Airbnb cash on cash: 1.62%

Traditional cash on cash: 3.15%

Airbnb Rental Income: $3871

Traditional Rental Income: $4276

Airbnb ROI: 1.62%