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
1017 TIMBER CREEK DRIVE Annapolis, MD Sun-Drenched Contemporary Home Minutes from Downtown Annapolis! Situated within the tree-l...	3 beds \| 2 baths \| 1,826 sq.ft.	$545,000	Airbnb cash on cash: 6.37% Traditional cash on cash: 2.73% Airbnb Rental Income: $5532 Traditional Rental Income: $2566 Airbnb ROI: 6.37% Traditional ROI: 2.73%
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: 3.48% Traditional cash on cash: 1.95% Airbnb Rental Income: $4278 Traditional Rental Income: $2437 Airbnb ROI: 3.48% Traditional ROI: 1.95%
1014 JACKSON STREET Annapolis, MD Major remodel was completed in 2018 ..."Eat-In" Kitchen features 42" white cabinetry, "s...	3 beds \| 2 baths \| 1,014 sq.ft.	$475,000	Airbnb cash on cash: 7.61% Traditional cash on cash: 3.15% Airbnb Rental Income: $5532 Traditional Rental Income: $2439 Airbnb ROI: 7.61% Traditional ROI: 3.15%
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: 4.56% Traditional cash on cash: 2.95% Airbnb Rental Income: $5532 Traditional Rental Income: $3379 Airbnb ROI: 4.56% 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: 6.69% Traditional cash on cash: 4.11% Airbnb Rental Income: $7081 Traditional Rental Income: $4061 Airbnb ROI: 6.69% Traditional ROI: 4.11%
702 MILLER RD Annapolis, MD 702 Miller Rd. is a most extraordinary property on 3/4 acre of serene privacy in downtown ...	3 beds \| 3 baths \| N/A	$775,000	Airbnb cash on cash: 3.96% Traditional cash on cash: 1.97% Airbnb Rental Income: $5532 Traditional Rental Income: $2985 Airbnb ROI: 3.96% Traditional ROI: 1.97%
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: 6.75% Traditional cash on cash: 3.43% Airbnb Rental Income: $7081 Traditional Rental Income: $3542 Airbnb ROI: 6.75% Traditional ROI: 3.43%
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: 5.52% Traditional cash on cash: 2.59% Airbnb Rental Income: $7117 Traditional Rental Income: $3605 Airbnb ROI: 5.52% Traditional ROI: 2.59%
512 JOSEPH JOHNSON DRIVE Annapolis, MD 2.375% Va Loan Assumption Eligible at owners discretion! Don't miss this meticulously mai...	3 beds \| 5 baths \| 2,272 sq.ft.	$589,900	Airbnb cash on cash: 5.38% Traditional cash on cash: 4.47% Airbnb Rental Income: $5532 Traditional Rental Income: $3925 Airbnb ROI: 5.38% Traditional ROI: 4.47%
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: 3.63% Traditional cash on cash: 1.36% Airbnb Rental Income: $7117 Traditional Rental Income: $3422 Airbnb ROI: 3.63% Traditional ROI: 1.36%
1142 LAKE HERON DRIVE #2A Annapolis, MD UPDATED 2 bedroom condo with water views and numerous upgrades throughout! Located just a ...	2 beds \| 2 baths \| 1,103 sq.ft.	$369,900	Airbnb cash on cash: 7.37% Traditional cash on cash: 3.8% Airbnb Rental Income: $4278 Traditional Rental Income: $2137 Airbnb ROI: 7.37% Traditional ROI: 3.8%
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: 9.41% Traditional cash on cash: 5.22% Airbnb Rental Income: $4278 Traditional Rental Income: $2194 Airbnb ROI: 9.41% Traditional ROI: 5.22%
2006 PEGGY STEWART WAY #101 Annapolis, MD Wonderful 2 bedroom, 2 bath ground level unit in sought after Tidewater Colony. Nice open ...	2 beds \| 2 baths \| 1,123 sq.ft.	$350,000	Airbnb cash on cash: 8.12% Traditional cash on cash: 4.89% Airbnb Rental Income: $4278 Traditional Rental Income: $2313 Airbnb ROI: 8.12% Traditional ROI: 4.89%
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: 6.21% Traditional cash on cash: 3.69% Airbnb Rental Income: $5532 Traditional Rental Income: $3169 Airbnb ROI: 6.21% Traditional ROI: 3.69%
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: 3.12% Traditional cash on cash: 1.84% Airbnb Rental Income: $4278 Traditional Rental Income: $2602 Airbnb ROI: 3.12% 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: 4.64% Traditional cash on cash: 2.25% Airbnb Rental Income: $4278 Traditional Rental Income: $2185 Airbnb ROI: 4.64% 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	$878,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 1.25% Airbnb Rental Income: $5532 Traditional Rental Income: $2669 Airbnb ROI: 3.39% Traditional ROI: 1.25%
115 LEE DR Annapolis, MD Welcome to 115 Lee Drive! This 4BR/2BA home is located in water privileged Hillsmere Shor...	4 beds \| 2 baths \| N/A	$560,000	Airbnb cash on cash: 9.01% Traditional cash on cash: 3.41% Airbnb Rental Income: $7117 Traditional Rental Income: $2809 Airbnb ROI: 9.01% Traditional ROI: 3.41%
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: 5.27% Traditional cash on cash: 2.23% Airbnb Rental Income: $7117 Traditional Rental Income: $3319 Airbnb ROI: 5.27% 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: 5.05% Traditional cash on cash: 2.74% Airbnb Rental Income: $5532 Traditional Rental Income: $3003 Airbnb ROI: 5.05% 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: 3.34% Traditional cash on cash: 1.07% Airbnb Rental Income: $7117 Traditional Rental Income: $3097 Airbnb ROI: 3.34% Traditional ROI: 1.07%
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: 4.55% Traditional cash on cash: 2.4% Airbnb Rental Income: $7117 Traditional Rental Income: $3842 Airbnb ROI: 4.55% 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: 1.39% Traditional cash on cash: 0.18% Airbnb Rental Income: $5532 Traditional Rental Income: $2797 Airbnb ROI: 1.39% Traditional ROI: 0.18%
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: 6.9% Traditional cash on cash: 3.64% Airbnb Rental Income: $4278 Traditional Rental Income: $2216 Airbnb ROI: 6.9% Traditional ROI: 3.64%
936 BAY RIDGE AVENUE #106 Annapolis, MD Bright and welcoming first-floor condo in a wonderful location! Freshly repainted with upd...	2 beds \| 2 baths \| 1,175 sq.ft.	$309,000	Airbnb cash on cash: 9.19% Traditional cash on cash: 5.65% Airbnb Rental Income: $4278 Traditional Rental Income: $2347 Airbnb ROI: 9.19% Traditional ROI: 5.65%
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: -0.97% Traditional cash on cash: -0.84% Airbnb Rental Income: $2154 Traditional Rental Income: $1824 Airbnb ROI: -0.97% Traditional ROI: -0.84%
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: 4.21% Traditional cash on cash: 3.31% Airbnb Rental Income: $7081 Traditional Rental Income: $4925 Airbnb ROI: 4.21% 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: 2.29% Traditional cash on cash: 0.81% Airbnb Rental Income: $7117 Traditional Rental Income: $3405 Airbnb ROI: 2.29% 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: 2.91% Traditional cash on cash: 1.18% Airbnb Rental Income: $5532 Traditional Rental Income: $2810 Airbnb ROI: 2.91% Traditional ROI: 1.18%
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: 3.4% Traditional cash on cash: 2.69% Airbnb Rental Income: $7081 Traditional Rental Income: $4920 Airbnb ROI: 3.4% 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: 1.53% Traditional cash on cash: 1.19% Airbnb Rental Income: $7081 Traditional Rental Income: $5033 Airbnb ROI: 1.53% Traditional ROI: 1.19%
7022 CHANNEL VILLAGE COURT #T2 Annapolis, MD Great View!! Property is offered completely furnished!! Beautiful 2 Bedrooms and 2 Bathroo...	2 beds \| 2 baths \| 1,194 sq.ft.	$499,999	Airbnb cash on cash: 4.89% Traditional cash on cash: 2.22% Airbnb Rental Income: $4278 Traditional Rental Income: $2130 Airbnb ROI: 4.89% Traditional ROI: 2.22%
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: 3.59% Traditional cash on cash: 2.13% Airbnb Rental Income: $4278 Traditional Rental Income: $2608 Airbnb ROI: 3.59% 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: 2.13% Traditional cash on cash: 0.85% Airbnb Rental Income: $7117 Traditional Rental Income: $3734 Airbnb ROI: 2.13% 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: 5.95% Traditional cash on cash: 3.77% Airbnb Rental Income: $4278 Traditional Rental Income: $2442 Airbnb ROI: 5.95% 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: 4.53% Traditional cash on cash: 3.18% Airbnb Rental Income: $7081 Traditional Rental Income: $4377 Airbnb ROI: 4.53% Traditional ROI: 3.18%
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: 1.83% Traditional cash on cash: 1.41% Airbnb Rental Income: $7117 Traditional Rental Income: $5125 Airbnb ROI: 1.83% Traditional ROI: 1.41%
164 W LAKE DRIVE Annapolis, MD New Price!! Fantastic transitional Waterfront home in Bay Ridge with private, deep w...	5 beds \| 6 baths \| 6,052 sq.ft.	$2,750,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 0.37% Airbnb Rental Income: $7081 Traditional Rental Income: $6382 Airbnb ROI: 0.11% Traditional ROI: 0.37%
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.	$1,389,000	Airbnb cash on cash: 2.54% Traditional cash on cash: 2.96% Airbnb Rental Income: $7081 Traditional Rental Income: $6254 Airbnb ROI: 2.54% Traditional ROI: 2.96%
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: 4.37% Traditional cash on cash: 2.43% Airbnb Rental Income: $4278 Traditional Rental Income: $2442 Airbnb ROI: 4.37% Traditional ROI: 2.43%

Real Estate investment in Annapolis, MD

There are 145 properties for sale in the city of Annapolis . The median list price in Annapolis is $627,000 and the average price per square foot is $278. In November 2024, the average monthly cash on cash return in Annapolis is 3.00%. The average monthly rental income in Annapolis is $2,779.

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

There are 145 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 $5,532.

Your search for investment property begins and ends here

Investment Property for Sale in Annapolis, MD

1017 TIMBER CREEK DRIVE

Annapolis, MD

3 beds | 2 baths | 1,826 sq.ft.

$545,000

Airbnb cash on cash: 6.37%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $5532

Traditional Rental Income: $2566

Airbnb ROI: 6.37%

Traditional ROI: 2.73%

5 PARK PLACE #514

Annapolis, MD

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

$660,000

Airbnb cash on cash: 3.48%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $4278

Traditional Rental Income: $2437

Airbnb ROI: 3.48%

Traditional ROI: 1.95%

1014 JACKSON STREET

Annapolis, MD

3 beds | 2 baths | 1,014 sq.ft.

$475,000

Airbnb cash on cash: 7.61%

Traditional cash on cash: 3.15%

Airbnb Rental Income: $5532

Traditional Rental Income: $2439

Airbnb ROI: 7.61%

Traditional ROI: 3.15%

916 BERWICK DRIVE

Annapolis, MD

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

$695,000

Airbnb cash on cash: 4.56%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $5532

Traditional Rental Income: $3379

Airbnb ROI: 4.56%

Traditional ROI: 2.95%

220 AUTUMN CHASE DRIVE

Annapolis, MD

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

$685,000

Airbnb cash on cash: 6.69%

Traditional cash on cash: 4.11%

Airbnb Rental Income: $7081

Traditional Rental Income: $4061

Airbnb ROI: 6.69%

Traditional ROI: 4.11%

702 MILLER RD

Annapolis, MD

3 beds | 3 baths | N/A

$775,000

Airbnb cash on cash: 3.96%

Traditional cash on cash: 1.97%

Airbnb Rental Income: $5532

Traditional Rental Income: $2985

Airbnb ROI: 3.96%

Traditional ROI: 1.97%

1201 BLACKWALNUT LANE

Annapolis, MD

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

$700,000

Airbnb cash on cash: 6.75%

Traditional cash on cash: 3.43%

Airbnb Rental Income: $7081

Traditional Rental Income: $3542

Airbnb ROI: 6.75%

Traditional ROI: 3.43%

2 HAMPTON COURT

Annapolis, MD

4 beds | 3 baths | 2,780 sq.ft.

$782,000

Airbnb cash on cash: 5.52%

Traditional cash on cash: 2.59%

Airbnb Rental Income: $7117

Traditional Rental Income: $3605

Airbnb ROI: 5.52%