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 54 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%
3535 Cohasset Ave Annapolis, MD Water view lot one block from the Bay at the end of peninsula.. Great view before leaves g...	3 beds \| 1 baths \| 1,512 sq.ft.	$415,000	Airbnb cash on cash: 3.07% Traditional cash on cash: 5.37% Airbnb Rental Income: $2680 Traditional Rental Income: $2939 Airbnb ROI: 3.07% Traditional ROI: 5.37%
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%
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: 1.33% Airbnb Rental Income: $2338 Traditional Rental Income: $2137 Airbnb ROI: 0.74% Traditional ROI: 1.33%
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.	$450,000	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%
1007 Park Ave Annapolis, MD GORGEOUS home in sought after Eastport ,one block from waterfront ! Recently updated hom...	3 beds \| 2 baths \| 2,430 sq.ft.	$1,075,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 0.95% Airbnb Rental Income: $2680 Traditional Rental Income: $2506 Airbnb ROI: 0.49% Traditional ROI: 0.95%
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 \| 5 baths \| 5,370 sq.ft.	$1,295,000	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%
34 Lafayette Ave Annapolis, MD Nestled in the sought-after Murray Hill section of Annapolis, this "diamond in the rough" ...	3 beds \| 1 baths \| 2,280 sq.ft.	$599,900	Airbnb cash on cash: 1.21% Traditional cash on cash: 1.01% Airbnb Rental Income: $2680 Traditional Rental Income: $1935 Airbnb ROI: 1.21% Traditional ROI: 1.01%
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%
553 CHOPTANK COVE CT Annapolis, MD For limited time, Sellers will pay $20,000 towards closing costs. English Tudor featuring ...	5 beds \| 4 baths \| N/A	$1,076,000	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%
45 E Lake Dr Annapolis, MD Rare Bay Ridge Opportunity 150 Wide Lot - Across the street from Lake Ogleton. Dont miss t...	3 beds \| 3 baths \| 2,043 sq.ft.	$3,250,000	Airbnb cash on cash: -0.74% Traditional cash on cash: -0.26% Airbnb Rental Income: $2680 Traditional Rental Income: $3505 Airbnb ROI: -0.74% Traditional ROI: -0.26%
289 HILLSMERE Drive Annapolis, MD Big Reduction of $24,000! Start your new year off in this 3-bedroom, 1-bath home situated ...	3 beds \| 1 baths \| 1,176 sq.ft.	$495,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 2.59% Airbnb Rental Income: $2680 Traditional Rental Income: $2172 Airbnb ROI: 2.31% Traditional ROI: 2.59%
778 Bon Haven Dr Annapolis, MD 778 Bon Haven Dr, RIVA, MD 21401 \| Single Family Residential	6 beds \| 4 baths \| 5,094 sq.ft.	$2,800,000	Airbnb cash on cash: -0.96% Traditional cash on cash: -0.82% Airbnb Rental Income: $3871 Traditional Rental Income: $3388 Airbnb ROI: -0.96% Traditional ROI: -0.82%
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%
2942 Southaven Dr Annapolis, MD 2942 Southaven Dr, RIVA, MD 21401 \| Single Family Residential	4 beds \| 2 baths \| 2,142 sq.ft.	$949,900	Airbnb cash on cash: 0.51% Traditional cash on cash: 0.56% Airbnb Rental Income: $3104 Traditional Rental Income: $2440 Airbnb ROI: 0.51% Traditional ROI: 0.56%
856 St Edmonds Pl Annapolis, MD 856 St Edmonds Pl, Arnold, MD 21401 \| Single Family Residential	5 beds \| 4 baths \| 6,412 sq.ft.	$3,100,000	Airbnb cash on cash: -1.11% Traditional cash on cash: -1% Airbnb Rental Income: $3871 Traditional Rental Income: $3347 Airbnb ROI: -1.11% Traditional ROI: -1%
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%
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%
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%
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%
812 Coachway Annapolis, MD 812 Coachway, Arnold, MD 21401 \| Single Family Residential	6 beds \| 5 baths \| 7,766 sq.ft.	$3,499,999	Airbnb cash on cash: -1.2% Traditional cash on cash: -0.72% Airbnb Rental Income: $3871 Traditional Rental Income: $4599 Airbnb ROI: -1.2% Traditional ROI: -0.72%
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%
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%
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%
2639 GREENBRIAR LN Annapolis, MD New Price - Seller wants offer today and a fast close. Incredible value for this Custom-...	3 beds \| 3 baths \| N/A	$1,500,000	Airbnb cash on cash: -0.73% Traditional cash on cash: -0.8% Airbnb Rental Income: $2680 Traditional Rental Income: $1947 Airbnb ROI: -0.73% Traditional ROI: -0.8%
3109 Ervin Ct Annapolis, MD 3109 Ervin Ct, Annapolis, MD 21403 \| Single Family Residential	3 beds \| 2 baths \| 1,801 sq.ft.	$849,900	Airbnb cash on cash: 0.35% Traditional cash on cash: 0.62% Airbnb Rental Income: $2680 Traditional Rental Income: $2259 Airbnb ROI: 0.35% 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%
1808 Lincoln Dr Annapolis, MD 1808 Lincoln Dr, Annapolis, MD 21401 \| Single Family Residential	3 beds \| 1 baths \| 1,008 sq.ft.	$405,000	Airbnb cash on cash: 3.06% Traditional cash on cash: 2.29% Airbnb Rental Income: $2680 Traditional Rental Income: $1754 Airbnb ROI: 3.06% Traditional ROI: 2.29%
16 Brice Rd Annapolis, MD This is an estate sale and being sold "As Is." A rancher that has been in this family for ...	3 beds \| 1 baths \| 1,936 sq.ft.	$800,000	Airbnb cash on cash: 0.6% Traditional cash on cash: -0.05% Airbnb Rental Income: $2680 Traditional Rental Income: $1558 Airbnb ROI: 0.6% Traditional ROI: -0.05%
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%

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%

3535 Cohasset Ave

Annapolis, MD

3 beds | 1 baths | 1,512 sq.ft.

$415,000

Airbnb cash on cash: 3.07%

Traditional cash on cash: 5.37%

Airbnb Rental Income: $2680

Traditional Rental Income: $2939

Airbnb ROI: 3.07%

Traditional ROI: 5.37%

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%

847 WOODMONT RD

Annapolis, MD

2 beds | 2 baths | N/A

$689,000

Airbnb cash on cash: 0.74%

Traditional cash on cash: 1.33%

Airbnb Rental Income: $2338

Traditional Rental Income: $2137

Airbnb ROI: 0.74%

Traditional ROI: 1.33%

1525 Hickory Wood Dr

Annapolis, MD

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

$450,000

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%

1007 Park Ave

Annapolis, MD

3 beds | 2 baths | 2,430 sq.ft.

$1,075,000

Airbnb cash on cash: 0.49%

Traditional cash on cash: 0.95%

Airbnb Rental Income: $2680

Traditional Rental Income: $2506

Airbnb ROI: 0.49%

Traditional ROI: 0.95%

143 Stilly Way

Annapolis, MD

6 beds | 5 baths | 5,370 sq.ft.

$1,295,000

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%

34 Lafayette Ave

Annapolis, MD

3 beds | 1 baths | 2,280 sq.ft.

$599,900

Airbnb cash on cash: 1.21%

Traditional cash on cash: 1.01%

Airbnb Rental Income: $2680

Traditional Rental Income: $1935

Airbnb ROI: 1.21%