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.	$484,950	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%
5 Park Pl #314 Annapolis, MD Live the Annapolis Lifestyle at the Residence at Park Place. Chic 2 bedroom, 2 bath cond...	2 beds \| 2 baths \| 1,056 sq.ft.	$564,000	Airbnb cash on cash: -1.19% Traditional cash on cash: 0.03% Airbnb Rental Income: $2338 Traditional Rental Income: $2401 Airbnb ROI: -1.19% Traditional ROI: 0.03%
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: -0.98% Traditional cash on cash: 0.85% Airbnb Rental Income: $2338 Traditional Rental Income: $2694 Airbnb ROI: -0.98% Traditional ROI: 0.85%
1608 Belle Dr Annapolis, MD 1608 Belle Drive, a beautiful well maintained end-unit residence with lots of natural ligh...	3 beds \| 3 baths \| 2,459 sq.ft.	$588,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 4.39% Airbnb Rental Income: $2680 Traditional Rental Income: $3876 Airbnb ROI: 1.05% Traditional ROI: 4.39%
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%
1 Shipwright Hbr Annapolis, MD Reduced & priced below 3/10/2018 appraisal! One of the finest homes on Spa Creek located o...	3 beds \| 3 baths \| 3,108 sq.ft.	$5,898,000	Airbnb cash on cash: -1.01% Traditional cash on cash: -0.85% Airbnb Rental Income: $2680 Traditional Rental Income: $2942 Airbnb ROI: -1.01% Traditional ROI: -0.85%
819 Janice Dr Annapolis, MD Beautiful Colonial-Under Construction*9 ft ceilings & Hardwood flrs- Main level 2 Story ...	4 beds \| 3 baths \| 4,043 sq.ft.	$1,195,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 0.28% Airbnb Rental Income: $3104 Traditional Rental Income: $2722 Airbnb ROI: -0.01% Traditional ROI: 0.28%
113 Bay Dr Annapolis, MD Stunning Chesapeake Bay views in desirable Bay Ridge neighborhood. Water view home, open f...	3 beds \| 2 baths \| 2,286 sq.ft.	$3,300,000	Airbnb cash on cash: -0.76% Traditional cash on cash: -0.66% Airbnb Rental Income: $2680 Traditional Rental Income: $2358 Airbnb ROI: -0.76% Traditional ROI: -0.66%
1109 Boucher Ave Annapolis, MD Greet neighbors from the front porch or entertain them on the private, fenced rear patio. ...	4 beds \| 4 baths \| 3,779 sq.ft.	$1,545,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 0.49% Airbnb Rental Income: $3104 Traditional Rental Income: $3496 Airbnb ROI: -0.28% Traditional ROI: 0.49%
1873 LUCE CREEK DR Annapolis, MD OPEN SATURDAY AND SUNDAY, FEB 28/MAR 1, 12:00-2:00! This one is a gem! Welcome to this abs...	5 beds \| 3 baths \| N/A	$815,000	Airbnb cash on cash: 2.14% Traditional cash on cash: N/A Airbnb Rental Income: $3871 Traditional Rental Income: $0 Airbnb ROI: 2.14% Traditional ROI: N/A
1136 Lake Heron Dr #3B Annapolis, MD Get ready to fall in love with this charming Annapolis condo! With two spacious bedrooms,...	2 beds \| 2 baths \| 1,412 sq.ft.	$405,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 1.85% Airbnb Rental Income: $2338 Traditional Rental Income: $2072 Airbnb ROI: 1.04% Traditional ROI: 1.85%
1703 Nimitz Dr Annapolis, MD Rarely available colonial in the extremely sought-after, water-privileged community of Adm...	3 beds \| 2 baths \| 2,629 sq.ft.	$795,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 1.61% Airbnb Rental Income: $2680 Traditional Rental Income: $2942 Airbnb ROI: 0.47% Traditional ROI: 1.61%
1071 Cedar Ridge Ct Annapolis, MD NEW PRICE and TRULY MOVE-IN READY! Save time and money with this meticulously maintained h...	3 beds \| 2 baths \| 1,320 sq.ft.	$382,500	Airbnb cash on cash: 2.52% Traditional cash on cash: 3.68% Airbnb Rental Income: $2680 Traditional Rental Income: $2469 Airbnb ROI: 2.52% Traditional ROI: 3.68%
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%
310 Giddings Ave Annapolis, MD West Annapolis! 3-bedroom, 3-bath home on corner lot in sought-after community needs TLC. ...	3 beds \| 3 baths \| 3,218 sq.ft.	$1,750,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 0.32% Airbnb Rental Income: $2680 Traditional Rental Income: $2942 Airbnb ROI: -0.23% Traditional ROI: 0.32%
8 ASHFORD CT Annapolis, MD Discover the charm of this 2-bedroom, 1.5-bathroom contemporary townhouse nestled in the d...	2 beds \| 2 baths \| N/A	$399,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 2.97% Airbnb Rental Income: $2338 Traditional Rental Income: $2034 Airbnb ROI: 2.23% Traditional ROI: 2.97%
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%
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 \| N/A	$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 Welcome to Chesapeake Harbour! This beautifully updated Marina VIEW 2-bedroom, 2-bath cond...	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%
2006 Peggy Stewart Way #204 Annapolis, MD LOCATION, LOCATION, LOCATION! This stylish 2 bedroom, 2 full bathroom condo is located in...	2 beds \| 2 baths \| 1,046 sq.ft.	$345,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 3.41% Airbnb Rental Income: $2338 Traditional Rental Income: $2157 Airbnb ROI: 2.18% Traditional ROI: 3.41%
1002 Tyler Ave Annapolis, MD Location Location location!! Modern rancher style home located near everything Annapolis h...	5 beds \| 2 baths \| 1,920 sq.ft.	$570,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 3.41% Airbnb Rental Income: $3871 Traditional Rental Income: $2932 Airbnb ROI: 3.61% Traditional ROI: 3.41%
2725 Cabernet Ln Annapolis, MD Luxury Living Meets Gated Seclusion at The Vineyards Tucked away in one of Annapolis's mos...	3 beds \| 3 baths \| 2,865 sq.ft.	$699,900	Airbnb cash on cash: 0.63% Traditional cash on cash: 2.01% Airbnb Rental Income: $2680 Traditional Rental Income: $2942 Airbnb ROI: 0.63% Traditional ROI: 2.01%
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%
306 Forbes St #M Annapolis, MD View of water from the upper deck area. 1 assigned space. Pool and marina are part of comm...	N/A beds \| 1 baths \| 500 sq.ft.	$365,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 0.2% Airbnb Rental Income: $1884 Traditional Rental Income: $1139 Airbnb ROI: 0.9% Traditional ROI: 0.2%
932 Riversedge Cir Annapolis, MD Welcome to 932 Riversedge Circle - an updated, one-level end-unit Villa in desirable Herit...	2 beds \| 1 baths \| 912 sq.ft.	$374,999	Airbnb cash on cash: 2.86% Traditional cash on cash: 1.83% Airbnb Rental Income: $2338 Traditional Rental Income: $1398 Airbnb ROI: 2.86% Traditional ROI: 1.83%
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%
4 Shiley St Annapolis, MD Here's the West Annapolis unicorn property that you've been waiting for! A VERY RARE TRIPL...	5 beds \| 5 baths \| 5,312 sq.ft.	$3,285,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 0.06% Airbnb Rental Income: $3871 Traditional Rental Income: $4522 Airbnb ROI: -0.43% Traditional ROI: 0.06%
2568 Glen Cv Annapolis, MD OPEN HOUSE SUNDAY 3/8 11-1. Tucked away at the end of a quiet cul-de-sac, this two-level h...	3 beds \| 2 baths \| 1,512 sq.ft.	$505,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 3.19% Airbnb Rental Income: $2680 Traditional Rental Income: $2765 Airbnb ROI: 1.66% Traditional ROI: 3.19%
940 Astern Way #102A Annapolis, MD If you are looking for convenience then come and visit this 1st FLOOR CONDO with PRIVATE P...	1 beds \| 1 baths \| 1,073 sq.ft.	$329,999	Airbnb cash on cash: -0.66% Traditional cash on cash: 1.2% Airbnb Rental Income: $1744 Traditional Rental Income: $1840 Airbnb ROI: -0.66% Traditional ROI: 1.2%
13 German St Annapolis, MD This charming fully renovated 3 level single family colonial home is located in sought aft...	5 beds \| 3 baths \| 2,590 sq.ft.	$1,170,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 1.53% Airbnb Rental Income: $3871 Traditional Rental Income: $3724 Airbnb ROI: 0.94% Traditional ROI: 1.53%
709 Skippers Ln Annapolis, MD Welcome to 709 Skippers Lane, a rare and versatile Live/Work townhome in the soughtafter V...	3 beds \| 2 baths \| 3,016 sq.ft.	$637,500	Airbnb cash on cash: 0.76% Traditional cash on cash: 3.14% Airbnb Rental Income: $2680 Traditional Rental Income: $3458 Airbnb ROI: 0.76% Traditional ROI: 3.14%
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%
1915 Towne Centre Blvd #309 Annapolis, MD Experience upscale urban living in this stunning 3rd-floor Everest model at Grandview, ide...	2 beds \| 2 baths \| 1,681 sq.ft.	$770,000	Airbnb cash on cash: -1.66% Traditional cash on cash: -0.41% Airbnb Rental Income: $2338 Traditional Rental Income: $2660 Airbnb ROI: -1.66% Traditional ROI: -0.41%
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 \| N/A	$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%
2052 Quaker Way #7 Annapolis, MD This charming condo in the heart of Annapolis offers the perfect blend of comfort and conv...	N/A beds \| N/A baths \| 1,122 sq.ft.	$349,990	Airbnb cash on cash: 1.16% Traditional cash on cash: 3.24% Airbnb Rental Income: $1884 Traditional Rental Income: $2064 Airbnb ROI: 1.16% Traditional ROI: 3.24%
1915 Towne Centre Blvd #406 Annapolis, MD Experience luxury living at its finest in this extraordinary residence that combines two u...	4 beds \| 3 baths \| 3,364 sq.ft.	$3,299,000	Airbnb cash on cash: -1.63% Traditional cash on cash: -1.47% Airbnb Rental Income: $3104 Traditional Rental Income: $2910 Airbnb ROI: -1.63% Traditional ROI: -1.47%
1955 Marconi Cir Annapolis, MD Heritage Harbour a 55 plus community. Welcome Home to 1955 Marconi Cir. This two bedroom t...	2 beds \| 2 baths \| 1,200 sq.ft.	$445,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 2.73% Airbnb Rental Income: $2338 Traditional Rental Income: $2217 Airbnb ROI: 1.64% Traditional ROI: 2.73%
721 Fairway Dr Annapolis, MD Elegant brick and siding split-foyer residence offering 4 bedrooms and 3 renovated full ba...	4 beds \| 3 baths \| 1,820 sq.ft.	$585,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 4.75% Airbnb Rental Income: $3104 Traditional Rental Income: $3687 Airbnb ROI: 2.39% Traditional ROI: 4.75%
2941 Southaven Dr Annapolis, MD Architecturally distinctive and thoughtfully designed, this three-level contemporary resid...	4 beds \| 2 baths \| 2,390 sq.ft.	$949,999	Airbnb cash on cash: 0.82% Traditional cash on cash: 4.01% Airbnb Rental Income: $3104 Traditional Rental Income: $5276 Airbnb ROI: 0.82% Traditional ROI: 4.01%

Real Estate investment in Annapolis, MD

There are 212 properties for sale in the city of Annapolis . The median list price in Annapolis is $643,250 and the average price per square foot is $287. In March 2026, the average monthly cash on cash return in Annapolis is 1.00%. The average monthly rental income in Annapolis is $2,358.

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

There are 212 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.

$484,950

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%

5 Park Pl #314

Annapolis, MD

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

$564,000

Airbnb cash on cash: -1.19%

Traditional cash on cash: 0.03%

Airbnb Rental Income: $2338

Traditional Rental Income: $2401

Airbnb ROI: -1.19%

Traditional ROI: 0.03%

1915 Towne Centre Blvd #807

Annapolis, MD

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

$545,000

Airbnb cash on cash: -0.98%

Traditional cash on cash: 0.85%

Airbnb Rental Income: $2338

Traditional Rental Income: $2694

Airbnb ROI: -0.98%

Traditional ROI: 0.85%

1608 Belle Dr

Annapolis, MD

3 beds | 3 baths | 2,459 sq.ft.

$588,000

Airbnb cash on cash: 1.05%

Traditional cash on cash: 4.39%

Airbnb Rental Income: $2680

Traditional Rental Income: $3876

Airbnb ROI: 1.05%

Traditional ROI: 4.39%

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%

1 Shipwright Hbr

Annapolis, MD

3 beds | 3 baths | 3,108 sq.ft.

$5,898,000

Airbnb cash on cash: -1.01%

Traditional cash on cash: -0.85%

Airbnb Rental Income: $2680

Traditional Rental Income: $2942

Airbnb ROI: -1.01%

Traditional ROI: -0.85%

819 Janice Dr

Annapolis, MD

4 beds | 3 baths | 4,043 sq.ft.

$1,195,000

Airbnb cash on cash: -0.01%

Traditional cash on cash: 0.28%

Airbnb Rental Income: $3104

Traditional Rental Income: $2722

Airbnb ROI: -0.01%

Traditional ROI: 0.28%

113 Bay Dr

Annapolis, MD

3 beds | 2 baths | 2,286 sq.ft.

$3,300,000

Airbnb cash on cash: -0.76%

Traditional cash on cash: -0.66%

Airbnb Rental Income: $2680

Traditional Rental Income: $2358

Airbnb ROI: -0.76%