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.

Investment Property for Sale in Annapolis, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
5 PARK PLACE #514 Annapolis, MD Move right in and enjoy the fabulous downtown Annapolis lifestyle in this meticulously mai...	2 beds \| 2 baths \| 1,056 sq.ft.	$660,000	Airbnb cash on cash: 1.51% Traditional cash on cash: 1.95% Airbnb Rental Income: $2829 Traditional Rental Income: $2437 Airbnb ROI: 1.51% Traditional ROI: 1.95%
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%
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%
633 BAYSTONE COURT Annapolis, MD Discover the perfect combination of location and lifestyle at 633 Baystone Court! This spa...	4 beds \| 2 baths \| 1,868 sq.ft.	$495,900	Airbnb cash on cash: 8.1% Traditional cash on cash: 3.82% Airbnb Rental Income: $5866 Traditional Rental Income: $2717 Airbnb ROI: 8.1% Traditional ROI: 3.82%
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: 2.15% Airbnb Rental Income: $4318 Traditional Rental Income: $2044 Airbnb ROI: 5.13% Traditional ROI: 2.15%
2900 SHIPMASTER WAY #315 Annapolis, MD Don't miss outâtake advantage of this fantastic opportunity as a buyer! Discover your dr...	2 beds \| 2 baths \| 1,008 sq.ft.	$299,900	Airbnb cash on cash: 5.13% Traditional cash on cash: 5.22% Airbnb Rental Income: $2829 Traditional Rental Income: $2194 Airbnb ROI: 5.13% Traditional ROI: 5.22%
217 VANGUARD LANE Annapolis, MD This stunning Annapolis townhome, located in the exclusive Village Greens gated community,...	3 beds \| 4 baths \| 2,000 sq.ft.	$529,900	Airbnb cash on cash: 4.17% Traditional cash on cash: 3.69% Airbnb Rental Income: $4318 Traditional Rental Income: $3169 Airbnb ROI: 4.17% Traditional ROI: 3.69%
1004 PRIMROSE RD #301 Annapolis, MD This beautiful condo has it all. Open floor plan with a balcony overlooking woods. This se...	1 beds \| 1 baths \| N/A	$254,990	Airbnb cash on cash: 8.52% Traditional cash on cash: 3.55% Airbnb Rental Income: $3393 Traditional Rental Income: $1441 Airbnb ROI: 8.52% Traditional ROI: 3.55%
7016 CLINTON COURT #22A Annapolis, MD This home is located in the gated waterfront condo community of Chesapeake Harbor where re...	2 beds \| 3 baths \| 1,830 sq.ft.	$649,900	Airbnb cash on cash: 1.12% Traditional cash on cash: 1.84% Airbnb Rental Income: $2829 Traditional Rental Income: $2602 Airbnb ROI: 1.12% Traditional ROI: 1.84%
940 ASTERN WAY #405 Annapolis, MD Beautifully Staged condominium The Reserve at Heritage Harbour. One of the largest units w...	2 beds \| 2 baths \| N/A	$535,000	Airbnb cash on cash: 2.22% Traditional cash on cash: 2.25% Airbnb Rental Income: $2829 Traditional Rental Income: $2185 Airbnb ROI: 2.22% Traditional ROI: 2.25%
7038 CLINTON CT #11B Annapolis, MD Welcome to an amazing condo experience right here in Chesapeake Harbour in Annapolis, MD. ...	3 beds \| 3 baths \| N/A	$850,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 1.26% Airbnb Rental Income: $4318 Traditional Rental Income: $2669 Airbnb ROI: 2.2% Traditional ROI: 1.26%
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%
5 PARK PL #428 Annapolis, MD Discover the perfect blend of comfort and convenience in this rare 3-bedroom, 2.5-bath con...	3 beds \| 3 baths \| N/A	$1,450,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 0.18% Airbnb Rental Income: $4318 Traditional Rental Income: $2797 Airbnb ROI: 0.64% Traditional ROI: 0.18%
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%
930 ASTERN WAY #207 Annapolis, MD Gorgeous corner unit on the back of the building provides privacy and peaceful views of th...	2 beds \| 2 baths \| 1,464 sq.ft.	$379,900	Airbnb cash on cash: 3.51% Traditional cash on cash: 3.64% Airbnb Rental Income: $2829 Traditional Rental Income: $2216 Airbnb ROI: 3.51% Traditional ROI: 3.64%
15 NEWMAN STREET Annapolis, MD Location, location, location! INVESTOR alert for an apartment unit building that can be co...	N/A beds \| N/A baths \| 3,509 sq.ft.	$1,799,999	Airbnb cash on cash: N/A Traditional cash on cash: -0.84% Airbnb Rental Income: $null Traditional Rental Income: $1824 Airbnb ROI: N/A Traditional ROI: -0.84%
2157 SAND CASTLE COURT Annapolis, MD Welcome to this Exceptional Gem with captivating Chesapeake Bay sunrises and Bay Bridge vi...	3 beds \| 5 baths \| 3,136 sq.ft.	$2,675,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 0.27% Airbnb Rental Income: $4318 Traditional Rental Income: $5182 Airbnb ROI: -0.44% Traditional ROI: 0.27%
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%
940 ASTERN WAY #504 Annapolis, MD Charming 2 bedroom, 2 bath condo for sale in the heart of Heritage Harbour's 55+ retiremen...	2 beds \| 2 baths \| 1,272 sq.ft.	$385,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 4.34% Airbnb Rental Income: $2829 Traditional Rental Income: $2532 Airbnb ROI: 3.33% Traditional ROI: 4.34%
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%
102 CHARLES STREET Annapolis, MD âCharming 2-bedroom, 2.5-bathroom corner townhome located in the heart of sought-after h...	2 beds \| 3 baths \| 948 sq.ft.	$675,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 1.27% Airbnb Rental Income: $2829 Traditional Rental Income: $2380 Airbnb ROI: 0.93% Traditional ROI: 1.27%
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%
1133 LAKE HERON DR #3B Annapolis, MD Nestled in the tranquil Lake Heron community, this sun-drenched top-floor end-unit condo o...	3 beds \| 2 baths \| N/A	$385,000	Airbnb cash on cash: 7.02% Traditional cash on cash: 4.51% Airbnb Rental Income: $4318 Traditional Rental Income: $2504 Airbnb ROI: 7.02% Traditional ROI: 4.51%
2100 CHESAPEAKE HARBOUR DRIVE #T2 Annapolis, MD Welcome to resort style living at Chesapeake Harbour! This spectacular 2 bedroom condo ha...	2 beds \| 2 baths \| 1,319 sq.ft.	$565,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 2.13% Airbnb Rental Income: $2829 Traditional Rental Income: $2608 Airbnb ROI: 1.3% Traditional ROI: 2.13%
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.	$1,600,000	Airbnb cash on cash: 1.09% Traditional cash on cash: 1.37% Airbnb Rental Income: $5866 Traditional Rental Income: $5125 Airbnb ROI: 1.09% Traditional ROI: 1.37%

Real Estate investment in Annapolis, MD

There are 132 properties for sale in the city of Annapolis . The median list price in Annapolis is $667,450 and the average price per square foot is $273. In December 2024, the average monthly cash on cash return in Annapolis is 3.00%. The average monthly rental income in Annapolis is $2,854.

Annapolis, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 132 investment properties available for sale in Annapolis.

In 2024, the best neighborhood to buy investment property is Annapolis.

The ROI for Short-Term is higher than the Long-Term in Annapolis with average rental income of $4,318.

Your search for investment property begins and ends here

Investment Property for Sale in Annapolis, MD

5 PARK PLACE #514

Annapolis, MD

2 beds | 2 baths | 1,056 sq.ft.

$660,000

Airbnb cash on cash: 1.51%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $2829

Traditional Rental Income: $2437

Airbnb ROI: 1.51%

Traditional ROI: 1.95%

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%