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 Franklin St Annapolis, MD 5 Franklin St, Annapolis, MD 21401 \| Single Family Residential	5 beds \| 6 baths \| 5,993 sq.ft.	$12,500,000	Airbnb cash on cash: -1.94% Traditional cash on cash: -1.57% Airbnb Rental Income: $2411 Traditional Rental Income: $6094 Airbnb ROI: -1.94% Traditional ROI: -1.57%
1100 Bay Ridge Ave Annapolis, MD This is a great opportunity to own in Eastport. Location is fantastic and a very easy wal...	4 beds \| 2 baths \| 1,720 sq.ft.	$799,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 1.45% Airbnb Rental Income: $2523 Traditional Rental Income: $2567 Airbnb ROI: 0.66% Traditional ROI: 1.45%
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.	$479,900	Airbnb cash on cash: -2.16% Traditional cash on cash: 0.4% Airbnb Rental Income: $1208 Traditional Rental Income: $1969 Airbnb ROI: -2.16% Traditional ROI: 0.4%
19 Boucher Pl Annapolis, MD Nestled in the charming Boucher Place community, this exquisite end-of-row townhouse offer...	3 beds \| 3 baths \| 1,800 sq.ft.	$819,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 1.45% Airbnb Rental Income: $2404 Traditional Rental Income: $2791 Airbnb ROI: 0.17% Traditional ROI: 1.45%
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: -2.58% Traditional cash on cash: 0.03% Airbnb Rental Income: $1459 Traditional Rental Income: $2401 Airbnb ROI: -2.58% Traditional ROI: 0.03%
417 Chesapeake Ave Annapolis, MD This exceptional 3-bedroom, 2.5-bath sun-drenched contemporary home sits on a spacious Eas...	3 beds \| 2 baths \| 2,259 sq.ft.	$1,495,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 0.15% Airbnb Rental Income: $2404 Traditional Rental Income: $3146 Airbnb ROI: -0.81% Traditional ROI: 0.15%
1915 Towne Centre Blvd #1105 Annapolis, MD A rare and spectacular 3,400 sq. ft. penthouse offering at the GrandView in Annapolis Town...	3 beds \| 3 baths \| 3,368 sq.ft.	$1,800,000	Airbnb cash on cash: -1.61% Traditional cash on cash: -1.23% Airbnb Rental Income: $2404 Traditional Rental Income: $2456 Airbnb ROI: -1.61% Traditional ROI: -1.23%
66 Franklin St #20 Annapolis, MD Stylish Street-Level Condo in the Heart of Annapolis. Welcome to this spacious 1-bedroom, ...	1 beds \| 1 baths \| 1,342 sq.ft.	$725,000	Airbnb cash on cash: -2.55% Traditional cash on cash: -0.43% Airbnb Rental Income: $1208 Traditional Rental Income: $2248 Airbnb ROI: -2.55% Traditional ROI: -0.43%
11 S Acton Pl Annapolis, MD 11 S Acton Pl, Annapolis, MD 21401 \| Single Family Residential	4 beds \| 3 baths \| 3,658 sq.ft.	$7,999,000	Airbnb cash on cash: -1.03% Traditional cash on cash: -0.88% Airbnb Rental Income: $2523 Traditional Rental Income: $3010 Airbnb ROI: -1.03% Traditional ROI: -0.88%
130 Summer Village Dr Annapolis, MD Beautiful spacious town home in sought after Riva Trace. updated 6 years ago.Pristine cond...	3 beds \| 2 baths \| 2,488 sq.ft.	$625,000	Airbnb cash on cash: 1.09% Traditional cash on cash: 1.93% Airbnb Rental Income: $2404 Traditional Rental Income: $2305 Airbnb ROI: 1.09% Traditional ROI: 1.93%
7 Silverwood Cir #3 Annapolis, MD Renovated Annapolis Condo \| Private Patio \| Community Amenities \| Move-In Ready Renovated ...	2 beds \| 2 baths \| N/A	$247,500	Airbnb cash on cash: -0.46% Traditional cash on cash: 3.79% Airbnb Rental Income: $1459 Traditional Rental Income: $2020 Airbnb ROI: -0.46% Traditional ROI: 3.79%
1107 Brashears St Annapolis, MD Discover the perfect blend of Annapolis charm and contemporary luxury at 1107 Brashears St...	5 beds \| 2 baths \| 1,800 sq.ft.	$825,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 1.43% Airbnb Rental Income: $2411 Traditional Rental Income: $2541 Airbnb ROI: 0.49% Traditional ROI: 1.43%
1915 Towne Centre Blvd #513 Annapolis, MD This exceptional 5th-floor condo offers a one-of-a-kind, unique floor plan with breathtaki...	2 beds \| 2 baths \| 1,485 sq.ft.	$549,000	Airbnb cash on cash: -2.78% Traditional cash on cash: 0.76% Airbnb Rental Income: $1459 Traditional Rental Income: $2844 Airbnb ROI: -2.78% Traditional ROI: 0.76%
774 Fairview Ave #F Annapolis, MD Welcome to easy waterfront living in the heart of Eastport. Rarely available and beautiful...	2 beds \| 2 baths \| 1,060 sq.ft.	$635,000	Airbnb cash on cash: -1.57% Traditional cash on cash: 0.49% Airbnb Rental Income: $1459 Traditional Rental Income: $2248 Airbnb ROI: -1.57% Traditional ROI: 0.49%
349 Epping Way Annapolis, MD Major price reduction, exceptional value for over 3,292 finished sq ft tucked among the tr...	4 beds \| 2 baths \| 3,292 sq.ft.	$925,000	Airbnb cash on cash: -0.07% Traditional cash on cash: -1.41% Airbnb Rental Income: $2523 Traditional Rental Income: $763 Airbnb ROI: -0.07% Traditional ROI: -1.41%
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: -1.06% Traditional cash on cash: -0.91% Airbnb Rental Income: $2404 Traditional Rental Income: $2613 Airbnb ROI: -1.06% Traditional ROI: -0.91%
2906 Boyds Cove Dr Annapolis, MD Beautiful stone front colonial in Boyds Cove. Gourmet kitchen w/ granite, cherry cabinets,...	4 beds \| 3 baths \| 3,770 sq.ft.	$899,900	Airbnb cash on cash: 0.16% Traditional cash on cash: 1.09% Airbnb Rental Income: $2523 Traditional Rental Income: $2692 Airbnb ROI: 0.16% Traditional ROI: 1.09%
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.	$1,125,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 0.43% Airbnb Rental Income: $2523 Traditional Rental Income: $2722 Airbnb ROI: -0.34% Traditional ROI: 0.43%
3280 Arundel On The Bay Rd Annapolis, MD Welcome to this beautifully maintained custom built Tudor Style home! With a primary suite...	5 beds \| 4 baths \| 3,144 sq.ft.	$799,900	Airbnb cash on cash: 0.43% Traditional cash on cash: 4.54% Airbnb Rental Income: $2411 Traditional Rental Income: $4883 Airbnb ROI: 0.43% Traditional ROI: 4.54%
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.	$2,999,999	Airbnb cash on cash: -0.82% Traditional cash on cash: -0.63% Airbnb Rental Income: $2404 Traditional Rental Income: $2358 Airbnb ROI: -0.82% Traditional ROI: -0.63%
607 Melvin Ave Annapolis, MD Open House Friday , 5/15 4:30-6:30PM & Saturday 5/16 12-2PM. Please join us!Adorable bunga...	2 beds \| 2 baths \| 1,102 sq.ft.	$899,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 0.66% Airbnb Rental Income: $1459 Traditional Rental Income: $2253 Airbnb ROI: -0.81% Traditional ROI: 0.66%
1254 WASHINGTON DR Annapolis, MD Rare waterfront redevelopment opportunity in Annapolis. The existing structure is a comple...	5 beds \| 5 baths \| N/A	$1,000,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 3.33% Airbnb Rental Income: $2411 Traditional Rental Income: $5132 Airbnb ROI: -0.23% Traditional ROI: 3.33%
619 Second St Annapolis, MD Just in time for the Holidays! This stunning 4 bedroom, 4 bath Coastal Contemporary home ...	3 beds \| 2 baths \| 3,004 sq.ft.	$1,650,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 0.04% Airbnb Rental Income: $2404 Traditional Rental Income: $2757 Airbnb ROI: -0.57% Traditional ROI: 0.04%
1014 Wells Ave Annapolis, MD Welcome Home to Eastport. Walk to the Eastport Shopping center for breakfast or to downtow...	4 beds \| 1 baths \| 880 sq.ft.	$419,900	Airbnb cash on cash: 2.2% Traditional cash on cash: 3.34% Airbnb Rental Income: $2523 Traditional Rental Income: $2363 Airbnb ROI: 2.2% Traditional ROI: 3.34%
1915 Towne Centre Blvd #403 Annapolis, MD Welcome to the highly sought-after "Davenport" corner unit in the prestigious GrandView co...	2 beds \| 2 baths \| 1,602 sq.ft.	$695,000	Airbnb cash on cash: -2.76% Traditional cash on cash: -0.15% Airbnb Rental Income: $1459 Traditional Rental Income: $2724 Airbnb ROI: -2.76% Traditional ROI: -0.15%
5 Park Pl #527 Annapolis, MD Nestled in the prestigious Park Place community, this exquisite mid-rise condominium build...	2 beds \| 2 baths \| 1,292 sq.ft.	$654,900	Airbnb cash on cash: -2.55% Traditional cash on cash: -0.58% Airbnb Rental Income: $1459 Traditional Rental Income: $2234 Airbnb ROI: -2.55% Traditional ROI: -0.58%
707 Buoy Ct Annapolis, MD Upscale Ryland Manor Home showcasing inspired open floor plan & custom detailing at every ...	5 beds \| 3 baths \| 3,729 sq.ft.	$924,900	Airbnb cash on cash: 0.34% Traditional cash on cash: 2.16% Airbnb Rental Income: $2411 Traditional Rental Income: $3390 Airbnb ROI: 0.34% Traditional ROI: 2.16%
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: -1.23% Traditional cash on cash: -0.89% Airbnb Rental Income: $2404 Traditional Rental Income: $2887 Airbnb ROI: -1.23% Traditional ROI: -0.89%
1117 PRIMROSE CT #301 Annapolis, MD Located in the community of The Landing at Spa Creek, 1117 Primrose Ct #301 gives condo li...	2 beds \| 1 baths \| N/A	$269,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 1.53% Airbnb Rental Income: $1459 Traditional Rental Income: $1473 Airbnb ROI: -0.23% Traditional ROI: 1.53%
304 Glen Ave Annapolis, MD 304 Glen Avenue is a beautiful single-family home in the heart of Annapolis just minutes t...	4 beds \| 3 baths \| 3,219 sq.ft.	$1,295,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 1.24% Airbnb Rental Income: $2523 Traditional Rental Income: $3334 Airbnb ROI: 0.06% Traditional ROI: 1.24%
3320 Arundel On The Bay Rd Annapolis, MD Welcome to 3320 Arundel on the Bay Road-where relaxed coastal living meets thoughtful desi...	3 beds \| 3 baths \| 1,812 sq.ft.	$600,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 3.71% Airbnb Rental Income: $2404 Traditional Rental Income: $3299 Airbnb ROI: 1.06% Traditional ROI: 3.71%
1000 Gomoljak Ln Annapolis, MD Looking for a secluded Mountaintop home tucked away on 3.89 acres within 15 minutes from d...	4 beds \| 3 baths \| 3,620 sq.ft.	$884,990	Airbnb cash on cash: 0.26% Traditional cash on cash: 1.75% Airbnb Rental Income: $2523 Traditional Rental Income: $3142 Airbnb ROI: 0.26% Traditional ROI: 1.75%
141 West St #401 Annapolis, MD Elegantly appointed penthouse residence in the sought-after 141 West building in the heart...	2 beds \| 2 baths \| 1,354 sq.ft.	$1,195,000	Airbnb cash on cash: -2.26% Traditional cash on cash: -0.22% Airbnb Rental Income: $1459 Traditional Rental Income: $3292 Airbnb ROI: -2.26% Traditional ROI: -0.22%
4 Southgate Ave Annapolis, MD An exceptional offering on Southgate Avenue in Murray Hill, this stately American Four Squ...	5 beds \| 4 baths \| 4,015 sq.ft.	$3,500,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 0.15% Airbnb Rental Income: $2411 Traditional Rental Income: $5504 Airbnb ROI: -0.99% Traditional ROI: 0.15%
494 FAWNS WALK Annapolis, MD 2,748 Total Square feet! Welcome to 494 Fawns Walk... a home that truly unfolds as you mo...	3 beds \| 3 baths \| N/A	$535,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 3.07% Airbnb Rental Income: $2404 Traditional Rental Income: $2559 Airbnb ROI: 1.58% Traditional ROI: 3.07%

Real Estate investment in Annapolis, MD

There are 339 properties for sale in the city of Annapolis . The median list price in Annapolis is $748,713 and the average price per square foot is $288. In May 2026, the average monthly cash on cash return in Annapolis is 1.00%. The average monthly rental income in Annapolis is $2,465.

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

There are 339 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 $2,404.

Your search for investment property begins and ends here

Investment Property for Sale in Annapolis, MD

5 Franklin St

Annapolis, MD

5 beds | 6 baths | 5,993 sq.ft.

$12,500,000

Airbnb cash on cash: -1.94%

Traditional cash on cash: -1.57%

Airbnb Rental Income: $2411

Traditional Rental Income: $6094

Airbnb ROI: -1.94%

Traditional ROI: -1.57%

1100 Bay Ridge Ave

Annapolis, MD

4 beds | 2 baths | 1,720 sq.ft.

$799,000

Airbnb cash on cash: 0.66%

Traditional cash on cash: 1.45%

Airbnb Rental Income: $2523

Traditional Rental Income: $2567

Airbnb ROI: 0.66%

Traditional ROI: 1.45%

5 Park Pl #431

Annapolis, MD

1 beds | 1 baths | 839 sq.ft.

$479,900

Airbnb cash on cash: -2.16%

Traditional cash on cash: 0.4%

Airbnb Rental Income: $1208

Traditional Rental Income: $1969

Airbnb ROI: -2.16%

Traditional ROI: 0.4%

19 Boucher Pl

Annapolis, MD

3 beds | 3 baths | 1,800 sq.ft.

$819,000

Airbnb cash on cash: 0.17%

Traditional cash on cash: 1.45%

Airbnb Rental Income: $2404

Traditional Rental Income: $2791

Airbnb ROI: 0.17%

Traditional ROI: 1.45%

5 Park Pl #314

Annapolis, MD

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

$564,000

Airbnb cash on cash: -2.58%

Traditional cash on cash: 0.03%

Airbnb Rental Income: $1459

Traditional Rental Income: $2401

Airbnb ROI: -2.58%

Traditional ROI: 0.03%

417 Chesapeake Ave

Annapolis, MD

3 beds | 2 baths | 2,259 sq.ft.

$1,495,000

Airbnb cash on cash: -0.81%

Traditional cash on cash: 0.15%

Airbnb Rental Income: $2404

Traditional Rental Income: $3146

Airbnb ROI: -0.81%

Traditional ROI: 0.15%

1915 Towne Centre Blvd #1105

Annapolis, MD

3 beds | 3 baths | 3,368 sq.ft.

$1,800,000

Airbnb cash on cash: -1.61%

Traditional cash on cash: -1.23%

Airbnb Rental Income: $2404

Traditional Rental Income: $2456

Airbnb ROI: -1.61%

Traditional ROI: -1.23%

66 Franklin St #20

Annapolis, MD

1 beds | 1 baths | 1,342 sq.ft.

$725,000

Airbnb cash on cash: -2.55%

Traditional cash on cash: -0.43%

Airbnb Rental Income: $1208

Traditional Rental Income: $2248

Airbnb ROI: -2.55%