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
309 MCDONOUGH ROAD Annapolis, MD Admiral Heights Beauty! 309 McDonough Rd features modern upgrades in a layout design for e...	4 beds \| 3 baths \| 2,945 sq.ft.	$890,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.53% Airbnb Rental Income: $null Traditional Rental Income: $3718 Airbnb ROI: N/A Traditional ROI: 2.53%
1915 TOWNE CENTRE BOULEVARD #807 Annapolis, MD PRICE IMPROVEMENT!! COSMOPOLITAN 2BR/2BA CONDO in the GRANDVIEW at TOWNE CENTRE! Condo com...	2 beds \| 2 baths \| 1,246 sq.ft.	$585,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.78% Airbnb Rental Income: $null Traditional Rental Income: $2694 Airbnb ROI: N/A Traditional ROI: 2.78%
66 FRANKLIN ST #20 Annapolis, MD Chic Street-Level Condo in the Heart of Annapolis. Welcome to this spacious 1-bedroom, 1.5...	1 beds \| 2 baths \| N/A	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.09% Airbnb Rental Income: $null Traditional Rental Income: $2248 Airbnb ROI: N/A Traditional ROI: 1.09%
5 PARK PLACE #107 Annapolis, MD Enjoy luxury condo living in this first-floor 2-bedroom, 2-bath home. Featuring gleaming h...	2 beds \| 2 baths \| 1,272 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.1% Airbnb Rental Income: $null Traditional Rental Income: $2551 Airbnb ROI: N/A Traditional ROI: 2.1%
1230 CRUMMELL AVENUE Annapolis, MD Discover a rare gem in Bay Highlands, the only Annapolis community with its own private, p...	4 beds \| 3 baths \| 2,555 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.16% Airbnb Rental Income: $null Traditional Rental Income: $3443 Airbnb ROI: N/A Traditional ROI: 1.16%
111 CLAY STREET Annapolis, MD Major Price Adjustment!! Great opportunity in West Annapolis! Discover the charm of 111 Cl...	3 beds \| 2 baths \| 1,568 sq.ft.	$599,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.9% Airbnb Rental Income: $null Traditional Rental Income: $2678 Airbnb ROI: N/A Traditional ROI: 2.9%
210 BOWEN COURT Annapolis, MD Welcome to an exquisite single-family residencea turnkey, move-in ready home just minutes ...	5 beds \| 4 baths \| 4,204 sq.ft.	$1,025,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.42% Airbnb Rental Income: $null Traditional Rental Income: $4074 Airbnb ROI: N/A Traditional ROI: 2.42%
1634 ORCHARD BEACH ROAD Annapolis, MD An incredible opportunity with endless potential awaits! This 3-bedroom, 3-bath home sits ...	3 beds \| 3 baths \| 2,868 sq.ft.	$930,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.08% Airbnb Rental Income: $null Traditional Rental Income: $3336 Airbnb ROI: N/A Traditional ROI: 2.08%
1192 BAY HIGHLANDS DRIVE Annapolis, MD Welcome to this generously spacious 4-bedroom, 2.5-bathroom home that blends comfort, char...	4 beds \| 3 baths \| 2,200 sq.ft.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.22% Airbnb Rental Income: $null Traditional Rental Income: $3363 Airbnb ROI: N/A Traditional ROI: 3.22%
103 NORMA ALLEY Annapolis, MD Welcome to this stunning, light-filled, and modern four-bedroom townhome located in the pr...	4 beds \| 5 baths \| 1,880 sq.ft.	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.17% Airbnb Rental Income: $null Traditional Rental Income: $3727 Airbnb ROI: N/A Traditional ROI: 3.17%
66 FRANKLIN STREET #509 Annapolis, MD Gorgeous, One-of-a-Kind Luxury Penthouse in Downtown Annapolis! Welcome to this stunning 3...	3 beds \| 4 baths \| 2,477 sq.ft.	$1,850,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.05% Airbnb Rental Income: $null Traditional Rental Income: $3393 Airbnb ROI: N/A Traditional ROI: 0.05%
2013 WARNERS TERRACE S #241 Annapolis, MD Welcome Home to this beautifully maintained 2-bedroom, 2-bath condo offering the perfect b...	2 beds \| 2 baths \| 1,062 sq.ft.	$335,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.48% Airbnb Rental Income: $null Traditional Rental Income: $2111 Airbnb ROI: N/A Traditional ROI: 4.48%
39 WINDWHISPER LN Annapolis, MD Tucked away on a peaceful cul-de-sac in the desirable Georgetown Grove community, this bea...	3 beds \| 4 baths \| N/A	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.65% Airbnb Rental Income: $null Traditional Rental Income: $3397 Airbnb ROI: N/A Traditional ROI: 2.65%
1096 LINDEN TREE DR Annapolis, MD Large double Lot with tons of potential - 2 Lots included in this sale 1096 (Lot 4) and 1...	3 beds \| 1 baths \| N/A	$535,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.73% Airbnb Rental Income: $null Traditional Rental Income: $2896 Airbnb ROI: N/A Traditional ROI: 3.73%
8 ASHFORD CT Annapolis, MD Price Adjustment! Welcome to 8 Ashford Ct - Modern Living in the Heart of Annapolis! Now o...	2 beds \| 2 baths \| N/A	$465,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.41% Airbnb Rental Income: $null Traditional Rental Income: $2034 Airbnb ROI: N/A Traditional ROI: 2.41%
1233 BOUCHER AVENUE Annapolis, MD Private and Peaceful Eastport Waterfront Community. Price Improvement - Waterfront Enclave...	3 beds \| 3 baths \| 2,052 sq.ft.	$675,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.38% Airbnb Rental Income: $null Traditional Rental Income: $3221 Airbnb ROI: N/A Traditional ROI: 2.38%
1755 ROBINHOOD ROAD Annapolis, MD From the moment you arrive, this 3-bedroom, 2.5-bathroom home welcomes you with charm and ...	3 beds \| 3 baths \| 1,664 sq.ft.	$824,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.8% Airbnb Rental Income: $null Traditional Rental Income: $2805 Airbnb ROI: N/A Traditional ROI: 1.8%
547 LEFTWICH LN #88 Annapolis, MD COSMOPOLITAN ANNAPOLIS TOWNHOME BOASTING SKYLINE ROOFTOP DECK! ADMIRALS SQUARE DUAL ASPEC...	3 beds \| 3 baths \| N/A	$594,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.23% Airbnb Rental Income: $null Traditional Rental Income: $2973 Airbnb ROI: N/A Traditional ROI: 3.23%
336 SEVERN ROAD Annapolis, MD Waterfront Living in Epping Forest with Stunning Views! Nestled in the exclusive, gated c...	2 beds \| 3 baths \| 1,708 sq.ft.	$829,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.74% Airbnb Rental Income: $null Traditional Rental Income: $3144 Airbnb ROI: N/A Traditional ROI: 1.74%
2900 SHIPMASTER WAY #211 Annapolis, MD NEW PRICE Welcome to your Annapolis retreatUnit #211 is a bright and breezy 2-bedroom,...	2 beds \| 2 baths \| 1,154 sq.ft.	$344,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.24% Airbnb Rental Income: $null Traditional Rental Income: $2162 Airbnb ROI: N/A Traditional ROI: 4.24%
138 QUIET WATERS PLACE Annapolis, MD ***Seller is in the process of replacing the roof as a proactive upgradethere are currentl...	2 beds \| 4 baths \| 1,752 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.57% Airbnb Rental Income: $null Traditional Rental Income: $2575 Airbnb ROI: N/A Traditional ROI: 3.57%
805 COXSWAIN WAY #205 Annapolis, MD Welcome to this beautifully updated 2-bedroom, 2-bathroom condo with a versatile den, perf...	2 beds \| 2 baths \| N/A	$434,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.23% Airbnb Rental Income: $null Traditional Rental Income: $2169 Airbnb ROI: N/A Traditional ROI: 3.23%
1200 GEMINI DRIVE Annapolis, MD Dont miss this beautifully updated 3-bedroom, 2.5-bath end-unit townhouse located just min...	3 beds \| 3 baths \| 1,304 sq.ft.	$324,999	Airbnb cash on cash: N/A Traditional cash on cash: 5.97% Airbnb Rental Income: $null Traditional Rental Income: $2543 Airbnb ROI: N/A Traditional ROI: 5.97%
930 ASTERN WAY #105 Annapolis, MD Beautifully Updated 2-Bedroom Condo in Heritage Harbour Welcome to this bright and spacio...	2 beds \| 2 baths \| 1,578 sq.ft.	$477,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.38% Airbnb Rental Income: $null Traditional Rental Income: $2162 Airbnb ROI: N/A Traditional ROI: 2.38%
5 PARK PLACE #428 Annapolis, MD Experience luxury and light in this rare 3-bedroom, 2.5-bath condo in the highly sought-af...	3 beds \| 3 baths \| 1,822 sq.ft.	$1,195,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.43% Airbnb Rental Income: $null Traditional Rental Income: $2797 Airbnb ROI: N/A Traditional ROI: 0.43%
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%
792 PARKWOOD AVE Annapolis, MD PRICE ADJUSTED! Seller has a 4.5% assumable VA loan for a qualified buyer. 792 Parkwood A...	4 beds \| 5 baths \| N/A	$895,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.57% Airbnb Rental Income: $null Traditional Rental Income: $4925 Airbnb ROI: N/A Traditional ROI: 3.57%
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: N/A Traditional cash on cash: 0.81% Airbnb Rental Income: $null Traditional Rental Income: $3405 Airbnb ROI: N/A Traditional ROI: 0.81%
930 ASTERN WAY #412 Annapolis, MD Welcome to effortless living in the vibrant 55+ community of Heritage Harbour! This beauti...	2 beds \| 2 baths \| N/A	$495,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.56% Airbnb Rental Income: $null Traditional Rental Income: $2139 Airbnb ROI: N/A Traditional ROI: 2.56%
198 CLAY STREET Annapolis, MD Welcome to 198 Clay Street in the heart of Annapolis! This charming row home offers water ...	2 beds \| 2 baths \| 902 sq.ft.	$429,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.14% Airbnb Rental Income: $null Traditional Rental Income: $2021 Airbnb ROI: N/A Traditional ROI: 3.14%
1809 LABROTT LANE Annapolis, MD Great SFH situated on flag lot in desirable location! Multiple living spaces on main level...	3 beds \| 4 baths \| 2,236 sq.ft.	$580,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.15% Airbnb Rental Income: $null Traditional Rental Income: $3966 Airbnb ROI: N/A Traditional ROI: 5.15%
919 BERWICK DRIVE Annapolis, MD Welcome to this exquisite home nestled conveniently close to downtown Annapolis and Eastpo...	4 beds \| 3 baths \| 2,292 sq.ft.	$799,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.1% Airbnb Rental Income: $null Traditional Rental Income: $3829 Airbnb ROI: N/A Traditional ROI: 3.1%
301 BURNSIDE STREET #A 202 Annapolis, MD The luxury waterfront lifestyle is awaiting you on Spa Creek in Eastport. This updated uni...	1 beds \| 1 baths \| 513 sq.ft.	$649,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.84% Airbnb Rental Income: $null Traditional Rental Income: $1727 Airbnb ROI: N/A Traditional ROI: 0.84%
1915 TOWNE CENTRE BOULEVARD #301 Annapolis, MD This impeccably maintained 2-bedroom, 2.5-bath Everest floor plan offers high-end living, ...	2 beds \| 3 baths \| 1,684 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.21% Airbnb Rental Income: $null Traditional Rental Income: $2599 Airbnb ROI: N/A Traditional ROI: 2.21%
106 STILLY WAY Annapolis, MD This stunning home, available for delivery in April, boasts high-end upgrades throughout. ...	4 beds \| 5 baths \| 4,594 sq.ft.	$999,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.67% Airbnb Rental Income: $null Traditional Rental Income: $4686 Airbnb ROI: N/A Traditional ROI: 3.67%
730 CRISFIELD WAY Annapolis, MD Stunning 5BR/4.5BA Luxury Home Grand residence featuring hardwood foyer, formal oval dinin...	5 beds \| 5 baths \| N/A	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 3% Airbnb Rental Income: $null Traditional Rental Income: $4276 Airbnb ROI: N/A Traditional ROI: 3%
40 OAK COURT Annapolis, MD Introducing a distinctive opportunity for visionary entrepreneurs and investors: a commerc...	2 beds \| 2 baths \| 1,061 sq.ft.	$389,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.61% Airbnb Rental Income: $null Traditional Rental Income: $2442 Airbnb ROI: N/A Traditional ROI: 4.61%
1831 DREW ST Annapolis, MD Tucked away with a long, freshly paved driveway and generous outdoor space, 1831 Drew Stre...	5 beds \| 2 baths \| N/A	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.05% Airbnb Rental Income: $null Traditional Rental Income: $2626 Airbnb ROI: N/A Traditional ROI: 3.05%
212 DUKE OF GLOUCESTER STREET Annapolis, MD Welcome to 212 Duke of Gloucester- a prime development opportunity in the heart of histori...	N/A beds \| N/A baths \| 2,300 sq.ft.	$649,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.48% Airbnb Rental Income: $null Traditional Rental Income: $2964 Airbnb ROI: N/A Traditional ROI: 2.48%
1915 TOWNE CENTRE BLVD #1210 Annapolis, MD FABULOUS PENTHOUSE. Embrace a lifestyle of unparalleled luxury and breathtaking views wit...	3 beds \| 4 baths \| N/A	$1,750,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.11% Airbnb Rental Income: $null Traditional Rental Income: $3337 Airbnb ROI: N/A Traditional ROI: 0.11%

Real Estate investment in Annapolis, MD

There are 168 properties for sale in the city of Annapolis . The median list price in Annapolis is $654,000 and the average price per square foot is $294. In September 2025, the average monthly cash on cash return in Annapolis is 3.00%. The average monthly rental income in Annapolis is $2,918.

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

There are 168 investment properties available for sale in Annapolis.

The ROI for Short-Term is higher than the Long-Term in Annapolis with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Annapolis, MD

309 MCDONOUGH ROAD

Annapolis, MD

4 beds | 3 baths | 2,945 sq.ft.

$890,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.53%

Airbnb Rental Income: $null

Traditional Rental Income: $3718

Airbnb ROI: N/A

Traditional ROI: 2.53%

1915 TOWNE CENTRE BOULEVARD #807

Annapolis, MD

2 beds | 2 baths | 1,246 sq.ft.

$585,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.78%

Airbnb Rental Income: $null

Traditional Rental Income: $2694

Airbnb ROI: N/A

Traditional ROI: 2.78%

66 FRANKLIN ST #20

Annapolis, MD

1 beds | 2 baths | N/A

$750,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.09%

Airbnb Rental Income: $null

Traditional Rental Income: $2248

Airbnb ROI: N/A

Traditional ROI: 1.09%

5 PARK PLACE #107

Annapolis, MD

2 beds | 2 baths | 1,272 sq.ft.

$625,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.1%

Airbnb Rental Income: $null

Traditional Rental Income: $2551

Airbnb ROI: N/A

Traditional ROI: 2.1%

1230 CRUMMELL AVENUE

Annapolis, MD

4 beds | 3 baths | 2,555 sq.ft.

$1,250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.16%

Airbnb Rental Income: $null

Traditional Rental Income: $3443

Airbnb ROI: N/A

Traditional ROI: 1.16%

111 CLAY STREET

Annapolis, MD

3 beds | 2 baths | 1,568 sq.ft.

$599,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.9%

Airbnb Rental Income: $null

Traditional Rental Income: $2678

Airbnb ROI: N/A

Traditional ROI: 2.9%

210 BOWEN COURT

Annapolis, MD

5 beds | 4 baths | 4,204 sq.ft.

$1,025,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.42%

Airbnb Rental Income: $null

Traditional Rental Income: $4074

Airbnb ROI: N/A

Traditional ROI: 2.42%

1634 ORCHARD BEACH ROAD

Annapolis, MD

3 beds | 3 baths | 2,868 sq.ft.

$930,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.08%

Airbnb Rental Income: $null

Traditional Rental Income: $3336

Airbnb ROI: N/A