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 34 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
349 EPPING WAY Annapolis, MD Priced to sell. Exceptional Value for over 3,292 finished sq ft. tucked among the trees in...	4 beds \| 3 baths \| N/A	$975,000	Airbnb cash on cash: -0.55% Traditional cash on cash: -1.39% Airbnb Rental Income: $2057 Traditional Rental Income: $763 Airbnb ROI: -0.55% Traditional ROI: -1.39%
1254 WASHINGTON DR Annapolis, MD Rare waterfront redevelopment opportunity in Annapolis. The existing structure is a comple...	5 beds \| 5 baths \| N/A	$1,000,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 3.33% Airbnb Rental Income: $1643 Traditional Rental Income: $5132 Airbnb ROI: -0.92% Traditional ROI: 3.33%
314 KINGSBERRY DR Annapolis, MD It's all about the land at this St. Margaret's Farm location with approximately 150 ft of ...	3 beds \| 3 baths \| N/A	$1,400,000	Airbnb cash on cash: -1.58% Traditional cash on cash: -0.26% Airbnb Rental Income: $1648 Traditional Rental Income: $2896 Airbnb ROI: -1.58% Traditional ROI: -0.26%
3320 ARUNDEL ON THE BAY RD Annapolis, MD Welcome to 3320 Arundel on the Bay Road-where relaxed coastal living meets thoughtful desi...	3 beds \| 4 baths \| N/A	$625,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 3.53% Airbnb Rental Income: $1648 Traditional Rental Income: $3299 Airbnb ROI: -0.1% Traditional ROI: 3.53%
207 1ST ST Annapolis, MD UPDATE: Open House this Saturday from 11-2pm. Seller is offering Seller help of $10,000 f...	4 beds \| 2 baths \| N/A	$484,900	Airbnb cash on cash: 1.18% Traditional cash on cash: 3.39% Airbnb Rental Income: $2057 Traditional Rental Income: $2528 Airbnb ROI: 1.18% Traditional ROI: 3.39%
163 PRINCE GEORGE ST Annapolis, MD Exceptional new pricing creates a compelling offering in the heart of Historic Annapolis. ...	3 beds \| 3 baths \| N/A	$1,325,000	Airbnb cash on cash: -1.27% Traditional cash on cash: -0.07% Airbnb Rental Income: $1648 Traditional Rental Income: $2654 Airbnb ROI: -1.27% Traditional ROI: -0.07%
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.	$565,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 3.45% Airbnb Rental Income: $1643 Traditional Rental Income: $2932 Airbnb ROI: 0.13% Traditional ROI: 3.45%
730 CRISFIELD WAY Annapolis, MD Welcome to Kingsport-where timeless elegance meets waterfront living. Nestled within this ...	5 beds \| 5 baths \| N/A	$865,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 3.15% Airbnb Rental Income: $1643 Traditional Rental Income: $4276 Airbnb ROI: -0.69% Traditional ROI: 3.15%
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: -1.33% Traditional cash on cash: -0.04% Airbnb Rental Income: $1082 Traditional Rental Income: $1916 Airbnb ROI: -1.33% 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: 0.85% Traditional cash on cash: 4.23% Airbnb Rental Income: $2057 Traditional Rental Income: $3325 Airbnb ROI: 0.85% Traditional ROI: 4.23%
1106 MAINSAIL DR Annapolis, MD At last, the one you've been waiting for. A beautiful home in a waterfront community. Mo...	5 beds \| 3 baths \| N/A	$849,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 1.47% Airbnb Rental Income: $1643 Traditional Rental Income: $2863 Airbnb ROI: -0.65% Traditional ROI: 1.47%
912 WINDSOR AVE Annapolis, MD Welcome to 912 Windsor Ave - The only ground up new construction home that is move in read...	5 beds \| 5 baths \| N/A	$2,050,000	Airbnb cash on cash: -1.51% Traditional cash on cash: -1.15% Airbnb Rental Income: $1643 Traditional Rental Income: $1866 Airbnb ROI: -1.51% Traditional ROI: -1.15%
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: -0.64% Traditional cash on cash: 0.89% Airbnb Rental Income: $2057 Traditional Rental Income: $3874 Airbnb ROI: -0.64% 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	$999,997	Airbnb cash on cash: -0.67% Traditional cash on cash: 1.76% Airbnb Rental Income: $1643 Traditional Rental Income: $3446 Airbnb ROI: -0.67% Traditional ROI: 1.76%
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: -1.35% Traditional cash on cash: -0.01% Airbnb Rental Income: $1648 Traditional Rental Income: $2751 Airbnb ROI: -1.35% Traditional ROI: -0.01%
3307 HARNESS CREEK RD Annapolis, MD Welcome to 3307 Harness Creek Road: a Nantucket style, coastal home set on a private penin...	3 beds \| 3 baths \| N/A	$3,145,000	Airbnb cash on cash: -1.19% Traditional cash on cash: -0.62% Airbnb Rental Income: $1648 Traditional Rental Income: $2863 Airbnb ROI: -1.19% Traditional ROI: -0.62%
111 JANWALL ST Annapolis, MD Charming 3-Bedroom Home on Quiet Cul-de-Sac Near Downtown Annapolis Welcome to this beaut...	3 beds \| 3 baths \| N/A	$525,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 3.87% Airbnb Rental Income: $1648 Traditional Rental Income: $2979 Airbnb ROI: 0.21% Traditional ROI: 3.87%
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	$3,950,000	Airbnb cash on cash: -1.72% Traditional cash on cash: -1.16% Airbnb Rental Income: $2057 Traditional Rental Income: $3581 Airbnb ROI: -1.72% Traditional ROI: -1.16%
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.	$499,999	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.43% Airbnb Rental Income: $1648 Traditional Rental Income: $2551 Airbnb ROI: 0.5% Traditional ROI: 3.43%
3130 STARBOARD DR Annapolis, MD Welcome to your dream home nestled in the sought after water privileged community of Ancho...	5 beds \| 3 baths \| N/A	$1,350,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 1.18% Airbnb Rental Income: $1643 Traditional Rental Income: $3607 Airbnb ROI: -0.75% Traditional ROI: 1.18%
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	$1,499,999	Airbnb cash on cash: -1.17% Traditional cash on cash: -0.25% Airbnb Rental Income: $1648 Traditional Rental Income: $2471 Airbnb ROI: -1.17% Traditional ROI: -0.25%
3275 HARNESS CREEK RD Annapolis, MD Set gracefully along Harness Creek with unobstructed water views and a rare boathouse, thi...	2 beds \| 3 baths \| N/A	$3,950,000	Airbnb cash on cash: -1.43% Traditional cash on cash: -0.78% Airbnb Rental Income: $1082 Traditional Rental Income: $3082 Airbnb ROI: -1.43% Traditional ROI: -0.78%
148 JEFFERSON ST Annapolis, MD Brand New Construction Completed and ready for move in! Price reduction and the home is re...	5 beds \| 3 baths \| N/A	$899,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 2.14% Airbnb Rental Income: $1643 Traditional Rental Income: $3179 Airbnb ROI: -0.25% Traditional ROI: 2.14%
1266 SEABRIGHT DR Annapolis, MD Welcome home to this three bedroom, two full bath split level home in sought after Cape St...	3 beds \| 2 baths \| N/A	$525,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 2.88% Airbnb Rental Income: $1648 Traditional Rental Income: $2421 Airbnb ROI: 0.36% Traditional ROI: 2.88%
100 1ST Street Annapolis, MD Better price! Welcome home to this charming and well-maintained 3-bedroom, 2-bath property...	3 beds \| 2 baths \| 1,537 sq.ft.	$449,900	Airbnb cash on cash: 0.66% Traditional cash on cash: 3.13% Airbnb Rental Income: $1648 Traditional Rental Income: $2226 Airbnb ROI: 0.66% Traditional ROI: 3.13%
1718 WOODLORE RD Annapolis, MD This unique Annapolitan Contemporary home is located in the quiet wooded enclave of WOODLO...	4 beds \| 4 baths \| N/A	$1,250,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 0.75% Airbnb Rental Income: $2057 Traditional Rental Income: $2798 Airbnb ROI: -0.34% Traditional ROI: 0.75%
515 POWELL DR Annapolis, MD Welcome Home to this beautifully appointed four-bedroom, two full bath and one half bath i...	4 beds \| 3 baths \| N/A	$899,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 1.97% Airbnb Rental Income: $2057 Traditional Rental Income: $3314 Airbnb ROI: -0.17% Traditional ROI: 1.97%
933 FOREST HILLS AVE Annapolis, MD Welcome home to this beautifully updated 3-bedroom, 2.5-bathroom duplex conveniently locat...	3 beds \| 3 baths \| N/A	$459,900	Airbnb cash on cash: 0.46% Traditional cash on cash: 2.87% Airbnb Rental Income: $1648 Traditional Rental Income: $2220 Airbnb ROI: 0.46% Traditional ROI: 2.87%
1915 CHERRY RD Annapolis, MD Charming and well-appointed, this corner lot rancher in the Pleasant Plains community offe...	3 beds \| 2 baths \| N/A	$600,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 0.81% Airbnb Rental Income: $1648 Traditional Rental Income: $1630 Airbnb ROI: 0.01% Traditional ROI: 0.81%
1717 PORTERS HILL ROAD Annapolis, MD Welcome to 1717 Porters Hill Road, a light-filled contemporary home designed around volume...	3 beds \| 2 baths \| N/A	$1,300,000	Airbnb cash on cash: -1.4% Traditional cash on cash: -0.44% Airbnb Rental Income: $1648 Traditional Rental Income: $2341 Airbnb ROI: -1.4% Traditional ROI: -0.44%
905 CORNELL AVE Annapolis, MD This exquisite 5-bedroom, 5 full bath stone-front traditional residence blends timeless so...	5 beds \| 5 baths \| N/A	$1,125,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 2.1% Airbnb Rental Income: $1643 Traditional Rental Income: $4335 Airbnb ROI: -0.92% Traditional ROI: 2.1%
103 WAINWRIGHT DR Annapolis, MD Exceptional offering in sought-after community of Admiral Heights! Great location near th...	3 beds \| 3 baths \| N/A	$775,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 2.25% Airbnb Rental Income: $1648 Traditional Rental Income: $3141 Airbnb ROI: -0.45% Traditional ROI: 2.25%
2550 GOLFERS RIDGE RD Annapolis, MD HERITAGE HARBOUR! It's the perfect size! 2 Bedrooms. 2 full Baths. Den. Sun Room Addition....	2 beds \| 2 baths \| N/A	$570,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 2.11% Airbnb Rental Income: $1082 Traditional Rental Income: $2211 Airbnb ROI: -0.71% Traditional ROI: 2.11%
1430 BAY HEAD RD Annapolis, MD Welcome to your beautiful new home on the picturesque Broadneck Peninsula, located within ...	4 beds \| 4 baths \| N/A	$850,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 2.64% Airbnb Rental Income: $2057 Traditional Rental Income: $3731 Airbnb ROI: -0.14% Traditional ROI: 2.64%

Your search for investment property begins and ends here

Single Family Homes for Sale in Annapolis, MD

349 EPPING WAY

Annapolis, MD

4 beds | 3 baths | N/A

$975,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: -1.39%

Airbnb Rental Income: $2057

Traditional Rental Income: $763

Airbnb ROI: -0.55%

Traditional ROI: -1.39%

1254 WASHINGTON DR

Annapolis, MD

5 beds | 5 baths | N/A

$1,000,000

Airbnb cash on cash: -0.92%

Traditional cash on cash: 3.33%

Airbnb Rental Income: $1643

Traditional Rental Income: $5132

Airbnb ROI: -0.92%

Traditional ROI: 3.33%

314 KINGSBERRY DR

Annapolis, MD

3 beds | 3 baths | N/A

$1,400,000

Airbnb cash on cash: -1.58%

Traditional cash on cash: -0.26%

Airbnb Rental Income: $1648

Traditional Rental Income: $2896

Airbnb ROI: -1.58%

Traditional ROI: -0.26%

3320 ARUNDEL ON THE BAY RD

Annapolis, MD

3 beds | 4 baths | N/A

$625,000

Airbnb cash on cash: -0.1%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $1648

Traditional Rental Income: $3299

Airbnb ROI: -0.1%

Traditional ROI: 3.53%

207 1ST ST

Annapolis, MD

4 beds | 2 baths | N/A

$484,900

Airbnb cash on cash: 1.18%

Traditional cash on cash: 3.39%

Airbnb Rental Income: $2057

Traditional Rental Income: $2528

Airbnb ROI: 1.18%

Traditional ROI: 3.39%

163 PRINCE GEORGE ST

Annapolis, MD

3 beds | 3 baths | N/A

$1,325,000

Airbnb cash on cash: -1.27%

Traditional cash on cash: -0.07%

Airbnb Rental Income: $1648

Traditional Rental Income: $2654

Airbnb ROI: -1.27%

Traditional ROI: -0.07%

1002 TYLER Avenue

Annapolis, MD

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

$565,000

Airbnb cash on cash: 0.13%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $1643

Traditional Rental Income: $2932

Airbnb ROI: 0.13%

Traditional ROI: 3.45%

730 CRISFIELD WAY

Annapolis, MD

5 beds | 5 baths | N/A

$865,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: 3.15%

Airbnb Rental Income: $1643

Traditional Rental Income: $4276

Airbnb ROI: -0.69%