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 90 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%
735 Whitehall Beach Rd Annapolis, MD This stunning split-level home in Whitehall Beach, offers a perfect blend of modern comfor...	3 beds \| 2 baths \| 2,406 sq.ft.	$650,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 3.07% Airbnb Rental Income: $2680 Traditional Rental Income: $3082 Airbnb ROI: 1.36% Traditional ROI: 3.07%
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%
807 Eastern Point Rd Annapolis, MD offered " For Rent or For Sale " .. BEST DEAL IN HERITAGE HARBOUR ? One of the largest...	5 beds \| 3 baths \| 1,694 sq.ft.	$650,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 1.8% Airbnb Rental Income: $3871 Traditional Rental Income: $2384 Airbnb ROI: 2.88% Traditional ROI: 1.8%
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%
1002 Tyler Ave 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%
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%
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%
1403 Corey Ln Annapolis, MD Tucked away at the end of a quiet, secluded street off No Cherry Grove (one of the prettie...	4 beds \| 2 baths \| 1,960 sq.ft.	$925,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 2.33% Airbnb Rental Income: $3104 Traditional Rental Income: $3883 Airbnb ROI: 0.61% Traditional ROI: 2.33%
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%
90 E Lake Dr Annapolis, MD Come explore the shores of Bay Ridge. As Annapolis's premiere waterfront community, Bay Ri...	5 beds \| 5 baths \| 4,204 sq.ft.	$3,595,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 0.05% Airbnb Rental Income: $3871 Traditional Rental Income: $6472 Airbnb ROI: -0.93% Traditional ROI: 0.05%
721 Fairway Dr Annapolis, MD Elegant brick and siding split-foyer residence offering 4 bedrooms and 3 renovated full ba...	4 beds \| 3 baths \| 1,820 sq.ft.	$585,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 4.75% Airbnb Rental Income: $3104 Traditional Rental Income: $3687 Airbnb ROI: 2.39% Traditional ROI: 4.75%
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%
1165 Green Holly Ct Annapolis, MD Cape St. Claire Home sold with Extra Lot and Detached Garage Plans! Plans in Documents. Th...	3 beds \| 2 baths \| 2,218 sq.ft.	$535,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 3.78% Airbnb Rental Income: $2680 Traditional Rental Income: $2901 Airbnb ROI: 2.06% Traditional ROI: 3.78%
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%
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.	$2,950,000	Airbnb cash on cash: -0.27% Traditional cash on cash: -0.11% Airbnb Rental Income: $3871 Traditional Rental Income: $3468 Airbnb ROI: -0.27% Traditional ROI: -0.11%
14-A Dorsey Ave Annapolis, MD TO BE BUILT / READY TO BE CUSTOMIZED. CONSTRUCTION STARTING SOON Starting at a base pric...	4 beds \| 2 baths \| 2,037 sq.ft.	$600,000	Airbnb cash on cash: 3.09% Traditional cash on cash: 4.31% Airbnb Rental Income: $3104 Traditional Rental Income: $3086 Airbnb ROI: 3.09% Traditional ROI: 4.31%
3300 Shore Dr Annapolis, MD Stunning Waterfront Coastal Retreat on Oyster Creek with Breathtaking Sunsets! This except...	4 beds \| 4 baths \| 2,798 sq.ft.	$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 \| 3,759 sq.ft.	$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%
1486 Downham Market Annapolis, MD 1486 Downham Market is the ultimate Annapolis deep-water estate-designed for those who dem...	5 beds \| 4 baths \| 5,260 sq.ft.	$3,250,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 0.37% Airbnb Rental Income: $3871 Traditional Rental Income: $6001 Airbnb ROI: -0.61% Traditional ROI: 0.37%
1162 Saint George Dr Annapolis, MD Seller is offering $5,000 towards Buyer's Closing Costs! Welcome to this beautifully mai...	4 beds \| 2 baths \| 1,643 sq.ft.	$540,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 3.51% Airbnb Rental Income: $3104 Traditional Rental Income: $2815 Airbnb ROI: 2.68% Traditional ROI: 3.51%
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%
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%
2762 Bon Haven Ln Annapolis, MD Welcome to this lovely, affordable waterfront ranch home and boat house at water's edge in...	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.	$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%

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%

735 Whitehall Beach Rd

Annapolis, MD

3 beds | 2 baths | 2,406 sq.ft.

$650,000

Airbnb cash on cash: 1.36%

Traditional cash on cash: 3.07%

Airbnb Rental Income: $2680

Traditional Rental Income: $3082

Airbnb ROI: 1.36%

Traditional ROI: 3.07%

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%

807 Eastern Point Rd

Annapolis, MD

5 beds | 3 baths | 1,694 sq.ft.

$650,000

Airbnb cash on cash: 2.88%

Traditional cash on cash: 1.8%

Airbnb Rental Income: $3871

Traditional Rental Income: $2384

Airbnb ROI: 2.88%

Traditional ROI: 1.8%

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%