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 Pl #431 Annapolis, MD PLEASE TAKE A LOOK AT EVERY CONDO IN THE BUILDING SOLD IN THE LAST YEAR AND THEN MAKE AN A...	1 beds \| 1 baths \| 839 sq.ft.	$489,900	Airbnb cash on cash: -1.16% Traditional cash on cash: 0.37% Airbnb Rental Income: $1744 Traditional Rental Income: $1969 Airbnb ROI: -1.16% Traditional ROI: 0.37%
1915 Towne Centre Blvd #807 Annapolis, MD FRESH INTERIOR PAINT THROUGHOUT - A PRISTINE, NEUTRAL PALETTE READY FOR YOUR STYLE!! SELLE...	2 beds \| 2 baths \| 1,246 sq.ft.	$545,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 0.96% Airbnb Rental Income: $2338 Traditional Rental Income: $2694 Airbnb ROI: -0.88% Traditional ROI: 0.96%
1394 STONECREEK RD Annapolis, MD Offer has been received and we have set an offer deadline of 3 PM on Tuesday 1/14 for the ...	4 beds \| 4 baths \| N/A	$585,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 2.85% Airbnb Rental Income: $3104 Traditional Rental Income: $2779 Airbnb ROI: 2.15% Traditional ROI: 2.85%
7 Silverwood Cir #3 Annapolis, MD 2022 renovated condo with private patio overlooking park/green/open space. Thoughtfully d...	2 beds \| 2 baths \| 1,314 sq.ft.	$275,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 3.38% Airbnb Rental Income: $2338 Traditional Rental Income: $2020 Airbnb ROI: 2.38% Traditional ROI: 3.38%
1213 Mckinley St Annapolis, MD Here's your chance to live in the Heart of Eastport! Cute cape cod with new kitchen and re...	3 beds \| 1 baths \| 1,008 sq.ft.	$449,000	Airbnb cash on cash: 2.93% Traditional cash on cash: 2.42% Airbnb Rental Income: $2680 Traditional Rental Income: $1833 Airbnb ROI: 2.93% Traditional ROI: 2.42%
9 Shipwright St Annapolis, MD Waterfront on Spa Creek in Downtown Annapolis!!! Property features open floor plan, walls ...	3 beds \| 2 baths \| 2,621 sq.ft.	$3,495,000	Airbnb cash on cash: -1.15% Traditional cash on cash: -0.89% Airbnb Rental Income: $2680 Traditional Rental Income: $2887 Airbnb ROI: -1.15% Traditional ROI: -0.89%
1915 Towne Centre Blvd #1004 Annapolis, MD Time to Make a Lifestyle Change - Stunning & Fabulous at The GrandView! Welcome to The Fla...	2 beds \| 2 baths \| 1,794 sq.ft.	$949,000	Airbnb cash on cash: -1.77% Traditional cash on cash: -0.69% Airbnb Rental Income: $2338 Traditional Rental Income: $2737 Airbnb ROI: -1.77% Traditional ROI: -0.69%
900 COACHWAY Annapolis, MD MID-CENTURY MODERN HOME IN THE DOWNS ON THE SEVERN! ALL OFFERS DUE AT 8PM SUNDAY 1/25/26. ...	3 beds \| 3 baths \| N/A	$824,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 1.23% Airbnb Rental Income: $2680 Traditional Rental Income: $2635 Airbnb ROI: 0.46% Traditional ROI: 1.23%
1909 Eleanor Ct Annapolis, MD Welcome to 1909 Eleanor Ct, a stunning colonial featuring five bedrooms and three and a ha...	5 beds \| 3 baths \| 4,790 sq.ft.	$950,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 2.23% Airbnb Rental Income: $3871 Traditional Rental Income: $3869 Airbnb ROI: 1.29% Traditional ROI: 2.23%
8 Ashford Ct Annapolis, MD Price Adjustment! Welcome to 8 Ashford Ct - Modern Living in the Heart of Annapolis! Now o...	2 beds \| 1 baths \| 1,248 sq.ft.	$399,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 2.29% Airbnb Rental Income: $1884 Traditional Rental Income: $2034 Airbnb ROI: 0.54% Traditional ROI: 2.29%
1553 Star Pine Dr Annapolis, MD Welcome to your new home in Whispering Woods! This charming duplex offers practical living...	2 beds \| 1 baths \| 1,060 sq.ft.	$339,990	Airbnb cash on cash: 3.2% Traditional cash on cash: 4.47% Airbnb Rental Income: $2338 Traditional Rental Income: $2165 Airbnb ROI: 3.2% Traditional ROI: 4.47%
847 WOODMONT RD Annapolis, MD Welcome Home to Comfort, Convenience & Community Living This well-maintained 2-bedroom, 2...	2 beds \| 2 baths \| N/A	$689,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 1.37% Airbnb Rental Income: $2338 Traditional Rental Income: $2163 Airbnb ROI: 0.74% Traditional ROI: 1.37%
2900 Shipmaster Way #216 Annapolis, MD Welcome to Waterfront living at its finest! This exclusive second floor unit is a rare gem...	2 beds \| 2 baths \| 1,048 sq.ft.	$347,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 4.76% Airbnb Rental Income: $2338 Traditional Rental Income: $2221 Airbnb ROI: 3.34% Traditional ROI: 4.76%
7002 Channel Village Ct #101 Annapolis, MD *PRICE LOWEREDSELLER WILL ENTERTAIN ALL OFFERS*Resort Style Community on the Chesape...	2 beds \| 2 baths \| 1,319 sq.ft.	$525,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 0.8% Airbnb Rental Income: $2338 Traditional Rental Income: $2002 Airbnb ROI: 0.31% Traditional ROI: 0.8%
547 LEFTWICH LN #88 Annapolis, MD BIG PRICE IMPROVEMENT! COSMOPOLITAN ANNAPOLIS TOWNHOME BOASTING SKYLINE ROOFTOP DECK! ADM...	3 beds \| 3 baths \| N/A	$560,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 3.49% Airbnb Rental Income: $2680 Traditional Rental Income: $2973 Airbnb ROI: 1.71% Traditional ROI: 3.49%
1525 Hickory Wood Dr Annapolis, MD This colonial style split foyer offers privacy & many major updates! Perfectly located in ...	3 beds \| 2 baths \| 1,265 sq.ft.	$445,000	Airbnb cash on cash: 2.9% Traditional cash on cash: 3.19% Airbnb Rental Income: $2680 Traditional Rental Income: $2167 Airbnb ROI: 2.9% Traditional ROI: 3.19%
2704 Summerview Way #103 Annapolis, MD Peaceful living in this private, spacious condo. The living room features a wood-burning...	2 beds \| 2 baths \| 1,285 sq.ft.	$365,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 2.67% Airbnb Rental Income: $2338 Traditional Rental Income: $2082 Airbnb ROI: 1.72% Traditional ROI: 2.67%
38 HARBOUR HEIGHTS DR Annapolis, MD Welcome home to the highly sought-after Seabreeze Harbour Gates community! This SUN lit en...	3 beds \| 3 baths \| N/A	$415,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 2.36% Airbnb Rental Income: $2680 Traditional Rental Income: $2024 Airbnb ROI: 2.41% Traditional ROI: 2.36%
1915 Towne Centre Blvd #402 Annapolis, MD CONTRACT ACCEPTED AND ACCEPTING BACK UP OFFERS This is it!!! Your chance to own your plac...	2 beds \| 2 baths \| 1,485 sq.ft.	$539,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 0.25% Airbnb Rental Income: $2338 Traditional Rental Income: $2529 Airbnb ROI: -1.27% Traditional ROI: 0.25%
406 Harbor Dr Annapolis, MD Welcome to 406 Harbor Drive, an exceptional residence in the heart of Hillsmere Shores, on...	4 beds \| 3 baths \| 4,000 sq.ft.	$795,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 2.11% Airbnb Rental Income: $3104 Traditional Rental Income: $3202 Airbnb ROI: 1.03% Traditional ROI: 2.11%
165 King George St Annapolis, MD There are so many option available for this property in the heart of Historic Annapolis. Y...	4 beds \| 3 baths \| 2,649 sq.ft.	$1,375,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 0.68% Airbnb Rental Income: $1884 Traditional Rental Income: $3263 Airbnb ROI: -0.79% Traditional ROI: 0.68%
1915 Towne Centre Blvd #707 Annapolis, MD Fantastic 2 Bedroom condo with great views of Annapolis Towne Centre from the balcony with...	2 beds \| 2 baths \| 1,246 sq.ft.	$535,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 0.82% Airbnb Rental Income: $2338 Traditional Rental Income: $2514 Airbnb ROI: -0.68% Traditional ROI: 0.82%
1009 OLD BAY RIDGE Road Annapolis, MD Rare double-lot opportunity in water-privileged Annapolis Roads! This beautifully updated ...	4 beds \| 4 baths \| 2,845 sq.ft.	$899,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 2.21% Airbnb Rental Income: $3104 Traditional Rental Income: $3390 Airbnb ROI: 1.03% Traditional ROI: 2.21%
2707 Judson Pl Annapolis, MD Welcome to 2707 Judson Place in Riva Woods. This inviting home sits on a private, fenced c...	3 beds \| 2 baths \| 2,156 sq.ft.	$590,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 3.7% Airbnb Rental Income: $2680 Traditional Rental Income: $3172 Airbnb ROI: 1.65% Traditional ROI: 3.7%
1 Tucker St Annapolis, MD 30K Price Improvement! Seller motivated! Incredible West Annapolis home that has been reno...	3 beds \| 2 baths \| 1,869 sq.ft.	$1,115,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 1.05% Airbnb Rental Income: $2680 Traditional Rental Income: $3155 Airbnb ROI: 0.01% Traditional ROI: 1.05%
328 Bulwark Aly Annapolis, MD Big price reduction for this beautifully maintained 3 level end unit garage townhome in th...	3 beds \| 2 baths \| 2,000 sq.ft.	$598,500	Airbnb cash on cash: 1.28% Traditional cash on cash: 3.35% Airbnb Rental Income: $2680 Traditional Rental Income: $3200 Airbnb ROI: 1.28% Traditional ROI: 3.35%
66 Franklin St #214 Annapolis, MD Truly one of a kind, this exceptional 1-bedroom, 2 full-bath residence in sought-after Act...	1 beds \| 2 baths \| 1,821 sq.ft.	$840,000	Airbnb cash on cash: -1.93% Traditional cash on cash: -0.27% Airbnb Rental Income: $1744 Traditional Rental Income: $2559 Airbnb ROI: -1.93% Traditional ROI: -0.27%
106 Stilly Way Annapolis, MD This stunning home is move-in ready and boasts high-end upgrades throughout. It features a...	4 beds \| 4 baths \| 4,594 sq.ft.	$983,540	Airbnb cash on cash: 1.25% Traditional cash on cash: 3.75% Airbnb Rental Income: $3104 Traditional Rental Income: $4686 Airbnb ROI: 1.25% Traditional ROI: 3.75%
2052 Quaker Way #7 Annapolis, MD This charming condo in the heart of Annapolis offers the perfect blend of comfort and conv...	2 beds \| 2 baths \| 1,122 sq.ft.	$349,990	Airbnb cash on cash: 2.22% Traditional cash on cash: 3.12% Airbnb Rental Income: $2338 Traditional Rental Income: $2064 Airbnb ROI: 2.22% Traditional ROI: 3.12%
940 Astern Way #607 Annapolis, MD Stunning Top Floor \| Private Wooded Views \| Designer Finishes Experience the perfect balan...	2 beds \| 2 baths \| 1,945 sq.ft.	$650,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 0.13% Airbnb Rental Income: $2338 Traditional Rental Income: $2544 Airbnb ROI: -1.16% Traditional ROI: 0.13%
143 Stilly Way Annapolis, MD May Delivery! This brand-new home is the perfect match for all of your family's needs! Thi...	6 beds \| 4 baths \| 5,370 sq.ft.	$1,199,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 3.43% Airbnb Rental Income: $3871 Traditional Rental Income: $5652 Airbnb ROI: 1.26% Traditional ROI: 3.43%
212 Duke Of Gloucester St 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.	$599,900	Airbnb cash on cash: -0.06% Traditional cash on cash: 2.77% Airbnb Rental Income: $1884 Traditional Rental Income: $2964 Airbnb ROI: -0.06% Traditional ROI: 2.77%
1915 Towne Centre Blvd #1210 Annapolis, MD FABULOUS PENTHOUSE. Embrace a lifestyle of unparalleled luxury and breathtaking views wit...	3 beds \| 3 baths \| 3,520 sq.ft.	$1,695,000	Airbnb cash on cash: -2.51% Traditional cash on cash: -1.69% Airbnb Rental Income: $2680 Traditional Rental Income: $3337 Airbnb ROI: -2.51% Traditional ROI: -1.69%
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: 2.49% Traditional cash on cash: 4.23% Airbnb Rental Income: $3104 Traditional Rental Income: $3325 Airbnb ROI: 2.49% Traditional ROI: 4.23%
1141 MAINSAIL DR Annapolis, MD PRICE ADJUSTED on this wonderful 4-bedroom home! Welcome to one of Annapolis' most sought-...	4 beds \| 3 baths \| N/A	$890,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 2.15% Airbnb Rental Income: $3104 Traditional Rental Income: $3431 Airbnb ROI: 0.9% Traditional ROI: 2.15%
703 Glendon Ave Annapolis, MD A brand-new home for the brand-new you. You've worked hard to get here-now you deserve a h...	5 beds \| 4 baths \| 4,116 sq.ft.	$2,750,000	Airbnb cash on cash: -0.27% Traditional cash on cash: -0.11% Airbnb Rental Income: $3871 Traditional Rental Income: $3468 Airbnb ROI: -0.27% Traditional ROI: -0.11%

Real Estate investment in Annapolis, MD

There are 148 properties for sale in the city of Annapolis . The median list price in Annapolis is $605,000 and the average price per square foot is $284. In February 2026, the average monthly cash on cash return in Annapolis is 1.00%. The average monthly rental income in Annapolis is $2,328.

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

There are 148 investment properties available for sale in Annapolis.

In 2026, 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 $2,680.

Your search for investment property begins and ends here

Investment Property for Sale in Annapolis, MD

5 Park Pl #431

Annapolis, MD

1 beds | 1 baths | 839 sq.ft.

$489,900

Airbnb cash on cash: -1.16%

Traditional cash on cash: 0.37%

Airbnb Rental Income: $1744

Traditional Rental Income: $1969

Airbnb ROI: -1.16%

Traditional ROI: 0.37%

1915 Towne Centre Blvd #807

Annapolis, MD

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

$545,000

Airbnb cash on cash: -0.88%

Traditional cash on cash: 0.96%

Airbnb Rental Income: $2338

Traditional Rental Income: $2694

Airbnb ROI: -0.88%

Traditional ROI: 0.96%

1394 STONECREEK RD

Annapolis, MD

4 beds | 4 baths | N/A

$585,000

Airbnb cash on cash: 2.15%

Traditional cash on cash: 2.85%

Airbnb Rental Income: $3104

Traditional Rental Income: $2779

Airbnb ROI: 2.15%

Traditional ROI: 2.85%

7 Silverwood Cir #3

Annapolis, MD

2 beds | 2 baths | 1,314 sq.ft.

$275,000

Airbnb cash on cash: 2.38%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $2338

Traditional Rental Income: $2020

Airbnb ROI: 2.38%

Traditional ROI: 3.38%

1213 Mckinley St

Annapolis, MD

3 beds | 1 baths | 1,008 sq.ft.

$449,000

Airbnb cash on cash: 2.93%

Traditional cash on cash: 2.42%

Airbnb Rental Income: $2680

Traditional Rental Income: $1833

Airbnb ROI: 2.93%

Traditional ROI: 2.42%

9 Shipwright St

Annapolis, MD

3 beds | 2 baths | 2,621 sq.ft.

$3,495,000

Airbnb cash on cash: -1.15%

Traditional cash on cash: -0.89%

Airbnb Rental Income: $2680

Traditional Rental Income: $2887

Airbnb ROI: -1.15%

Traditional ROI: -0.89%

1915 Towne Centre Blvd #1004

Annapolis, MD

2 beds | 2 baths | 1,794 sq.ft.

$949,000

Airbnb cash on cash: -1.77%

Traditional cash on cash: -0.69%

Airbnb Rental Income: $2338

Traditional Rental Income: $2737

Airbnb ROI: -1.77%

Traditional ROI: -0.69%

900 COACHWAY

Annapolis, MD

3 beds | 3 baths | N/A

$824,000

Airbnb cash on cash: 0.46%

Traditional cash on cash: 1.23%

Airbnb Rental Income: $2680

Traditional Rental Income: $2635

Airbnb ROI: 0.46%