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 98 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
414 JEFFERSON STREET Annapolis, MD Stunning Eastport Craftsman light filled home with 9 foot ceilings & open floor plan. Des...	4 beds \| 4 baths \| 3,658 sq.ft.	$1,450,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 1.27% Airbnb Rental Income: $5866 Traditional Rental Income: $3912 Airbnb ROI: 1.86% Traditional ROI: 1.27%
1177 SOUTHVIEW DR Annapolis, MD FRESH PAINT being done this weekend. This home is PRICED TO SELL! This 4-bedroom, 2.5 bat...	4 beds \| 3 baths \| N/A	$498,000	Airbnb cash on cash: 7.92% Traditional cash on cash: 4.59% Airbnb Rental Income: $5866 Traditional Rental Income: $3147 Airbnb ROI: 7.92% Traditional ROI: 4.59%
862 RUDDER WAY Annapolis, MD Welcome to Heritage Harbour, a distinguished enclave for sophisticated living. This 3-bedr...	3 beds \| 2 baths \| 2,490 sq.ft.	$630,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 2.41% Airbnb Rental Income: $4318 Traditional Rental Income: $2800 Airbnb ROI: 3.45% Traditional ROI: 2.41%
916 BERWICK DRIVE Annapolis, MD Welcome to 916 Berwick; tucked into the sought after Ambridge Community, conveniently loca...	3 beds \| 3 baths \| 2,662 sq.ft.	$695,000	Airbnb cash on cash: 3% Traditional cash on cash: 2.95% Airbnb Rental Income: $4318 Traditional Rental Income: $3379 Airbnb ROI: 3% Traditional ROI: 2.95%
220 AUTUMN CHASE DRIVE Annapolis, MD Nestled in the sought-after Riva Trace community of Annapolis, this possible 5-bedroom, 3 ...	5 beds \| 4 baths \| 3,214 sq.ft.	$685,000	Airbnb cash on cash: 6.13% Traditional cash on cash: 4.11% Airbnb Rental Income: $6650 Traditional Rental Income: $4061 Airbnb ROI: 6.13% Traditional ROI: 4.11%
1201 BLACKWALNUT LANE Annapolis, MD This beautifully renovated Colonial is ready for you to call home! Nestled on a tranquil s...	5 beds \| 4 baths \| 1,972 sq.ft.	$700,000	Airbnb cash on cash: 6.2% Traditional cash on cash: 3.43% Airbnb Rental Income: $6650 Traditional Rental Income: $3542 Airbnb ROI: 6.2% Traditional ROI: 3.43%
1760 BIRDBROOK TRAIL Annapolis, MD Epic Home just listed in Waterfront Epping Forest Community! Post and Beam Tree House with...	3 beds \| 2 baths \| 2,667 sq.ft.	$950,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 1.65% Airbnb Rental Income: $4318 Traditional Rental Income: $2902 Airbnb ROI: 2.23% Traditional ROI: 1.65%
986 WESTWAY Annapolis, MD 986 Westway offers the perfect blend of modern living and coastal charm! This like-new hom...	3 beds \| 2 baths \| 1,269 sq.ft.	$499,900	Airbnb cash on cash: 5.22% Traditional cash on cash: 3.5% Airbnb Rental Income: $4318 Traditional Rental Income: $2607 Airbnb ROI: 5.22% Traditional ROI: 3.5%
2 HAMPTON COURT Annapolis, MD Welcome to Hunt Meadow, a highly sought-after community in Annapolis, MD! This spacious an...	4 beds \| 3 baths \| 2,780 sq.ft.	$782,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 2.59% Airbnb Rental Income: $5866 Traditional Rental Income: $3605 Airbnb ROI: 4.09% Traditional ROI: 2.59%
7 HILL STREET Annapolis, MD Welcome to 7 Hill Street, a beautifully maintained and upgraded single-family Colonial hom...	4 beds \| 3 baths \| 2,538 sq.ft.	$1,100,000	Airbnb cash on cash: 2.61% Traditional cash on cash: 1.36% Airbnb Rental Income: $5866 Traditional Rental Income: $3422 Airbnb ROI: 2.61% Traditional ROI: 1.36%
1155 TYLER AVE Annapolis, MD Charming 3-Bedroom Ranch on Spacious Corner Lot Welcome to this cozy 3-bedroom, ranch-styl...	3 beds \| 1 baths \| N/A	$490,000	Airbnb cash on cash: 5.13% Traditional cash on cash: 3.7% Airbnb Rental Income: $4318 Traditional Rental Income: $2755 Airbnb ROI: 5.13% Traditional ROI: 3.7%
2668 OGLETON ROAD Annapolis, MD Just the perfect place to call home in Annapolis Roads! This lovely 4 bedroom, 2.5 bath br...	4 beds \| 3 baths \| 2,602 sq.ft.	$854,900	Airbnb cash on cash: 3.96% Traditional cash on cash: 2.23% Airbnb Rental Income: $5866 Traditional Rental Income: $3319 Airbnb ROI: 3.96% Traditional ROI: 2.23%
909 LANGDON COURT Annapolis, MD Welcome to this stunning, 3 bedroom 2 full bath bright, and sunny contemporary home just m...	3 beds \| 3 baths \| 2,335 sq.ft.	$659,900	Airbnb cash on cash: 3.4% Traditional cash on cash: 2.74% Airbnb Rental Income: $4318 Traditional Rental Income: $3003 Airbnb ROI: 3.4% Traditional ROI: 2.74%
3536 SARATOGA AVENUE Annapolis, MD WELCOME! Come see this stunning property that has everything youâll ever want or need i...	4 beds \| 3 baths \| 2,368 sq.ft.	$1,250,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 0.95% Airbnb Rental Income: $5866 Traditional Rental Income: $3097 Airbnb ROI: 2.33% Traditional ROI: 0.95%
212 BOWEN COURT Annapolis, MD This home is a PERFECT 10!! Impeccably maintained and beautifully updated, this 4BR 3.5 ba...	4 beds \| 4 baths \| 4,367 sq.ft.	$949,000	Airbnb cash on cash: 3.37% Traditional cash on cash: 2.4% Airbnb Rental Income: $5866 Traditional Rental Income: $3842 Airbnb ROI: 3.37% Traditional ROI: 2.4%
1471 AMBERWOOD DRIVE N Annapolis, MD Back on the market! Still time to make this your home for the holidays! Welcome to your dr...	4 beds \| 2 baths \| 1,698 sq.ft.	$475,000	Airbnb cash on cash: 8.42% Traditional cash on cash: 3.79% Airbnb Rental Income: $5866 Traditional Rental Income: $2639 Airbnb ROI: 8.42% Traditional ROI: 3.79%
792 PARKWOOD AVENUE Annapolis, MD Highly desirable Eastport home. Lots of room at 3,500+ sq ft. 2 owner suites. Separate fin...	5 beds \| 5 baths \| 3,575 sq.ft.	$949,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 3.31% Airbnb Rental Income: $6650 Traditional Rental Income: $4925 Airbnb ROI: 3.8% Traditional ROI: 3.31%
400 JEFFERSON STREET Annapolis, MD Custom coastal craftsman home is currently under construction in Eastport - Annapolis, Mar...	4 beds \| 3 baths \| 3,640 sq.ft.	$1,700,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 0.81% Airbnb Rental Income: $5866 Traditional Rental Income: $3405 Airbnb ROI: 1.63% Traditional ROI: 0.81%
407 TAYLOR AVENUE Annapolis, MD Active Air BnB. The Goat House, Located within a stones throw to the Naval-Marine Corps ...	3 beds \| 2 baths \| 1,966 sq.ft.	$1,000,000	Airbnb cash on cash: 1.83% Traditional cash on cash: 1.18% Airbnb Rental Income: $4318 Traditional Rental Income: $2810 Airbnb ROI: 1.83% Traditional ROI: 1.18%
729 ANNAPOLIS NECK ROAD Annapolis, MD *AGENTS AND BUYERS MUST SIGN A HOLD HARMLESS AGREEMENT BEFORE AN APPOINTMENT CAN BE MADE...	4 beds \| 2 baths \| 1,356 sq.ft.	$400,000	Airbnb cash on cash: 9.7% Traditional cash on cash: 3.82% Airbnb Rental Income: $5866 Traditional Rental Income: $2496 Airbnb ROI: 9.7% Traditional ROI: 3.82%
1422 HOWARD ROAD Annapolis, MD Welcome home to 1422 Howard Rd! This contemporary Oyster Harbor coastal paradise in the hi...	5 beds \| 5 baths \| 3,505 sq.ft.	$1,199,999	Airbnb cash on cash: 3.08% Traditional cash on cash: 2.69% Airbnb Rental Income: $6650 Traditional Rental Income: $4920 Airbnb ROI: 3.08% Traditional ROI: 2.69%
1270 SWAN DRIVE Annapolis, MD Waterfront Retreat on Little Magothy River, Annapolis. Welcome to this exquisite waterfr...	5 beds \| 5 baths \| 2,848 sq.ft.	$2,097,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 1.19% Airbnb Rental Income: $6650 Traditional Rental Income: $5033 Airbnb ROI: 1.35% Traditional ROI: 1.19%
1009 DULANEY LANE Annapolis, MD Build Your Dream Weekend Retreat in Annapolis Roads! Discover the perfect opportunity to...	4 beds \| 4 baths \| 2,896 sq.ft.	$1,695,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 0.85% Airbnb Rental Income: $5866 Traditional Rental Income: $3734 Airbnb ROI: 1.47% Traditional ROI: 0.85%
40 OAK COURT Annapolis, MD RARE COMMERCIAL/RESIDENTIAL FORECLOSURE IN ANNAPOLIS!! Structure is ready for your build-o...	2 beds \| 2 baths \| 1,061 sq.ft.	$459,000	Airbnb cash on cash: 3.13% Traditional cash on cash: 3.77% Airbnb Rental Income: $2829 Traditional Rental Income: $2442 Airbnb ROI: 3.13% Traditional ROI: 3.77%
110 STILLY WAY Annapolis, MD New Construction - Move In Ready February -March 2025! Please go to Model home to tour! W...	5 beds \| 6 baths \| 5,017 sq.ft.	$1,061,190	Airbnb cash on cash: 3.12% Traditional cash on cash: 2.13% Airbnb Rental Income: $6650 Traditional Rental Income: $4377 Airbnb ROI: 3.12% Traditional ROI: 2.13%
371 CARRIAGE PARK WAY Annapolis, MD Discover the timeless charm of 371 Carriage Park Way, a New England transition-style home ...	4 beds \| 5 baths \| 6,576 sq.ft.	$1,575,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 1.41% Airbnb Rental Income: $5866 Traditional Rental Income: $5125 Airbnb ROI: 1.12% Traditional ROI: 1.41%
301 UNITY LANE Annapolis, MD Walk in and be amazed with a beautiful and luxurious remodeled open floor concept. Open t...	5 beds \| 6 baths \| 7,616 sq.ft.	$1,349,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 3.07% Airbnb Rental Income: $6650 Traditional Rental Income: $6254 Airbnb ROI: 2.35% Traditional ROI: 3.07%
2539 MISSION HILLS COURT Annapolis, MD Seller will consider all offers! Seller is willing to give a $2500 credit towards new car...	2 beds \| 2 baths \| 1,694 sq.ft.	$515,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 2.43% Airbnb Rental Income: $2829 Traditional Rental Income: $2442 Airbnb ROI: 1.87% Traditional ROI: 2.43%
3335 THOMAS POINT ROAD Annapolis, MD BRING ALL OFFERS! Pinterest Perfect, Beautifully Remodeled 4 Bedroom, 2 Full Bath Rancher ...	4 beds \| 2 baths \| 1,380 sq.ft.	$579,999	Airbnb cash on cash: 6.76% Traditional cash on cash: 2.86% Airbnb Rental Income: $5866 Traditional Rental Income: $2590 Airbnb ROI: 6.76% Traditional ROI: 2.86%
2997 SOUTHAVEN DR Annapolis, MD Don't miss out on this beautifully remodeled home, set on a private and expansive .86-acre...	4 beds \| 3 baths \| N/A	$895,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 2.06% Airbnb Rental Income: $5866 Traditional Rental Income: $3171 Airbnb ROI: 3.9% Traditional ROI: 2.06%
1806 RIVER WATCH Annapolis, MD Priced to sell! Custom built waterfront home located on Luce Creek offers a serene setting...	5 beds \| 6 baths \| 5,872 sq.ft.	$2,995,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 0.53% Airbnb Rental Income: $6650 Traditional Rental Income: $6411 Airbnb ROI: 0.15% Traditional ROI: 0.53%
3422 NARRAGANSETT AVENUE Annapolis, MD Fully renovated house with limited water view in desirable Arundel In The Bay, just steps ...	3 beds \| 3 baths \| 2,200 sq.ft.	$710,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 2.17% Airbnb Rental Income: $4318 Traditional Rental Income: $2560 Airbnb ROI: 3.45% Traditional ROI: 2.17%
1159 PINE TREE DRIVE Annapolis, MD Open House Saturday, Nov 23, 1-3 PM! Stop by or explore the online 3D tour! Welcome to 115...	4 beds \| 3 baths \| 2,116 sq.ft.	$500,000	Airbnb cash on cash: 7.89% Traditional cash on cash: 5.47% Airbnb Rental Income: $5866 Traditional Rental Income: $3570 Airbnb ROI: 7.89% Traditional ROI: 5.47%
1012 MOUNT HOLLY DR Annapolis, MD Coming soon, new house to be built.	4 beds \| 3 baths \| N/A	$800,000	Airbnb cash on cash: 4.1% Traditional cash on cash: 3.02% Airbnb Rental Income: $5866 Traditional Rental Income: $3897 Airbnb ROI: 4.1% Traditional ROI: 3.02%
1879 WHITEHALL ROAD Annapolis, MD Mint condition! Move right in and enjoy private and serene waterfront living on nearly 4 a...	5 beds \| 6 baths \| 6,321 sq.ft.	$3,750,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 0.41% Airbnb Rental Income: $6650 Traditional Rental Income: $6591 Airbnb ROI: 0.05% Traditional ROI: 0.41%
3101 ERVIN COURT Annapolis, MD Welcome Home to 3101 Ervin Court. This stunning, newly renovated home located in a quiet c...	3 beds \| 3 baths \| 1,808 sq.ft.	$684,900	Airbnb cash on cash: 3.31% Traditional cash on cash: 2.44% Airbnb Rental Income: $4318 Traditional Rental Income: $2854 Airbnb ROI: 3.31% Traditional ROI: 2.44%
1632 WINCHESTER RD Annapolis, MD Please note - this tax record is associated with only 3.3 acres, but this listing is for t...	1 beds \| 1 baths \| N/A	$1,900,000	Airbnb cash on cash: -0.34% Traditional cash on cash: -1.03% Airbnb Rental Income: $3393 Traditional Rental Income: $1412 Airbnb ROI: -0.34% Traditional ROI: -1.03%
515 LITTLE CURRENT DRIVE Annapolis, MD Classic Charm Meets Potential in Revell Downs. Discover the possibilities at 515 Little Cu...	3 beds \| 2 baths \| 1,614 sq.ft.	$440,000	Airbnb cash on cash: 6.08% Traditional cash on cash: 5.03% Airbnb Rental Income: $4318 Traditional Rental Income: $2977 Airbnb ROI: 6.08% Traditional ROI: 5.03%
9 RUSTY RED DRIVE Annapolis, MD STUNNING NEW COMMUNITY BY STURBRIDGE HOMES IN COVETED ANNAPOLIS NEIGHBORHOOD. Discover ...	5 beds \| 5 baths \| 5,062 sq.ft.	$1,490,000	Airbnb cash on cash: 1.67% Traditional cash on cash: 1.44% Airbnb Rental Income: $6650 Traditional Rental Income: $5042 Airbnb ROI: 1.67% Traditional ROI: 1.44%
1590 KESWICK PL Annapolis, MD SIGNIFICANT PRICE REDUCTION & EXQUISITE LUXURY HOME! BEAUTIFUL WATERFRONT PROPERTY AND NE...	4 beds \| 4 baths \| N/A	$2,595,000	Airbnb cash on cash: 0.26% Traditional cash on cash: -0.12% Airbnb Rental Income: $5866 Traditional Rental Income: $3792 Airbnb ROI: 0.26% Traditional ROI: -0.12%

Your search for investment property begins and ends here

Single Family Homes for Sale in Annapolis, MD

414 JEFFERSON STREET

Annapolis, MD

4 beds | 4 baths | 3,658 sq.ft.

$1,450,000

Airbnb cash on cash: 1.86%

Traditional cash on cash: 1.27%

Airbnb Rental Income: $5866

Traditional Rental Income: $3912

Airbnb ROI: 1.86%

Traditional ROI: 1.27%

1177 SOUTHVIEW DR

Annapolis, MD

4 beds | 3 baths | N/A

$498,000

Airbnb cash on cash: 7.92%

Traditional cash on cash: 4.59%

Airbnb Rental Income: $5866

Traditional Rental Income: $3147

Airbnb ROI: 7.92%

Traditional ROI: 4.59%

862 RUDDER WAY

Annapolis, MD

3 beds | 2 baths | 2,490 sq.ft.

$630,000

Airbnb cash on cash: 3.45%

Traditional cash on cash: 2.41%

Airbnb Rental Income: $4318

Traditional Rental Income: $2800

Airbnb ROI: 3.45%

Traditional ROI: 2.41%

916 BERWICK DRIVE

Annapolis, MD

3 beds | 3 baths | 2,662 sq.ft.

$695,000

Airbnb cash on cash: 3%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $4318

Traditional Rental Income: $3379

Airbnb ROI: 3%

Traditional ROI: 2.95%

220 AUTUMN CHASE DRIVE

Annapolis, MD

5 beds | 4 baths | 3,214 sq.ft.

$685,000

Airbnb cash on cash: 6.13%

Traditional cash on cash: 4.11%

Airbnb Rental Income: $6650

Traditional Rental Income: $4061

Airbnb ROI: 6.13%

Traditional ROI: 4.11%

1201 BLACKWALNUT LANE

Annapolis, MD

5 beds | 4 baths | 1,972 sq.ft.

$700,000

Airbnb cash on cash: 6.2%

Traditional cash on cash: 3.43%

Airbnb Rental Income: $6650

Traditional Rental Income: $3542

Airbnb ROI: 6.2%

Traditional ROI: 3.43%

1760 BIRDBROOK TRAIL

Annapolis, MD

3 beds | 2 baths | 2,667 sq.ft.

$950,000

Airbnb cash on cash: 2.23%

Traditional cash on cash: 1.65%

Airbnb Rental Income: $4318

Traditional Rental Income: $2902

Airbnb ROI: 2.23%

Traditional ROI: 1.65%

986 WESTWAY

Annapolis, MD

3 beds | 2 baths | 1,269 sq.ft.

$499,900

Airbnb cash on cash: 5.22%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $4318

Traditional Rental Income: $2607

Airbnb ROI: 5.22%