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: -1.93% Traditional cash on cash: -1.57% Airbnb Rental Income: $2481 Traditional Rental Income: $6094 Airbnb ROI: -1.93% Traditional ROI: -1.57%
5 Park Pl #431 Annapolis, MD Discover the perfect blend of comfort and convenience in this charming 1-bedroom, 1-bathro...	1 beds \| 1 baths \| 839 sq.ft.	$475,000	Airbnb cash on cash: -1.88% Traditional cash on cash: -0.01% Airbnb Rental Income: $1593 Traditional Rental Income: $1969 Airbnb ROI: -1.88% Traditional ROI: -0.01%
19 Boucher Pl Annapolis, MD NEW PRICE ALERT!!******Nestled in the charming Boucher Place community, this exquisite end...	3 beds \| 3 baths \| 1,800 sq.ft.	$799,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 1.26% Airbnb Rental Income: $2689 Traditional Rental Income: $2791 Airbnb ROI: 0.27% Traditional ROI: 1.26%
66 FRANKLIN ST #20 Annapolis, MD Stylish Street-Level Condo in the Heart of Annapolis. Welcome to this spacious 1-bedroom, ...	1 beds \| 2 baths \| N/A	$725,000	Airbnb cash on cash: -2.08% Traditional cash on cash: -0.43% Airbnb Rental Income: $1593 Traditional Rental Income: $2248 Airbnb ROI: -2.08% Traditional ROI: -0.43%
5 Park Pl #414 Annapolis, MD Discover this charming 2-bedroom, 2-bathroom unit in the desirable Park Place community, b...	2 beds \| 2 baths \| 1,056 sq.ft.	$564,900	Airbnb cash on cash: -1.75% Traditional cash on cash: -0.57% Airbnb Rental Income: $1908 Traditional Rental Income: $2024 Airbnb ROI: -1.75% Traditional ROI: -0.57%
11 S Acton Pl Annapolis, MD 11 S Acton Pl, Annapolis, MD 21401 \| Single Family Residential	4 beds \| 3 baths \| 3,658 sq.ft.	$7,250,000	Airbnb cash on cash: -0.93% Traditional cash on cash: -0.87% Airbnb Rental Income: $3333 Traditional Rental Income: $3010 Airbnb ROI: -0.93% Traditional ROI: -0.87%
2102 Chesapeake Harbour Dr E #202 Annapolis, MD Welcome to coastal living at its finest in Annapolis' gated Chesapeake Harbour community! ...	3 beds \| 3 baths \| 1,666 sq.ft.	$675,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 0.69% Airbnb Rental Income: $2689 Traditional Rental Income: $2723 Airbnb ROI: -0.36% Traditional ROI: 0.69%
110 Lake View Dr Annapolis, MD Beautiful home on a corner lot in desirable WATER privileged community of Hillsmere Estate...	3 beds \| 2 baths \| 2,242 sq.ft.	$720,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 1.95% Airbnb Rental Income: $2689 Traditional Rental Income: $2470 Airbnb ROI: 1.34% Traditional ROI: 1.95%
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: -2.05% Traditional cash on cash: 0.76% Airbnb Rental Income: $1908 Traditional Rental Income: $2844 Airbnb ROI: -2.05% Traditional ROI: 0.76%
126 Spring Place Way Annapolis, MD Nestled in the charming community of Riva Trace, this delightful townhouse offers a perfec...	3 beds \| 3 baths \| 2,323 sq.ft.	$554,900	Airbnb cash on cash: 1.42% Traditional cash on cash: 3.18% Airbnb Rental Income: $2689 Traditional Rental Income: $2990 Airbnb ROI: 1.42% Traditional ROI: 3.18%
774 FAIRVIEW AVE #F Annapolis, MD PRICE ADJUSTED AS SELLERS HAVE FOUND THEIR NEXT HOME Welcome to easy waterfront living in ...	2 beds \| 2 baths \| N/A	$545,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 0.74% Airbnb Rental Income: $1908 Traditional Rental Income: $2248 Airbnb ROI: -0.92% Traditional ROI: 0.74%
34 Pinkney St Annapolis, MD Totally renovated Historic home in the heart of downtown Annapolis, a stone's throw from s...	2 beds \| 1 baths \| 1,040 sq.ft.	$685,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 0.39% Airbnb Rental Income: $1908 Traditional Rental Income: $1402 Airbnb ROI: 0.39% Traditional ROI: 0.39%
2691 Claibourne Rd Annapolis, MD Nestled in the highly sought-after Annapolis Roads community, this spacious Colonial offer...	4 beds \| 3 baths \| 2,533 sq.ft.	$825,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 2.56% Airbnb Rental Income: $3333 Traditional Rental Income: $3524 Airbnb ROI: 1.35% Traditional ROI: 2.56%
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.	$5,675,000	Airbnb cash on cash: -1.01% Traditional cash on cash: -0.91% Airbnb Rental Income: $2689 Traditional Rental Income: $2613 Airbnb ROI: -1.01% Traditional ROI: -0.91%
145 Prince George St Annapolis, MD Welcome to 145 Prince George St., a distinctive historic home that blends classic architec...	3 beds \| 2 baths \| 1,476 sq.ft.	$1,100,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 0.45% Airbnb Rental Income: $2689 Traditional Rental Income: $2614 Airbnb ROI: -0.05% Traditional ROI: 0.45%
3280 Arundel On The Bay Rd Annapolis, MD Significant Price improvement! Priced to sell, incredible value! Welcome to this beautiful...	5 beds \| 4 baths \| 3,144 sq.ft.	$750,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 4.9% Airbnb Rental Income: $2481 Traditional Rental Income: $4883 Airbnb ROI: 0.61% Traditional ROI: 4.9%
219 Lockwood Ct Annapolis, MD Nestled in the heart of Eastport, this stunning Craftsman-style home offers the perfect bl...	4 beds \| 4 baths \| 1,848 sq.ft.	$1,650,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 0.11% Airbnb Rental Income: $3333 Traditional Rental Income: $3351 Airbnb ROI: -0.36% Traditional ROI: 0.11%
1164 Latrobe Dr Annapolis, MD Get ready for a great summer in this great location! New Kitchen w/ SS appliances, granite...	4 beds \| 2 baths \| 1,926 sq.ft.	$525,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 2.85% Airbnb Rental Income: $3333 Traditional Rental Income: $2369 Airbnb ROI: 3.29% Traditional ROI: 2.85%
101 Carraway Ln Annapolis, MD DON'T MISS THIS OPPORTUNITY! MOVE-IN READY! Reduced again and seller wants it SOLD! Just b...	5 beds \| 4 baths \| 3,432 sq.ft.	$679,000	Airbnb cash on cash: 0.47% Traditional cash on cash: N/A Airbnb Rental Income: $2481 Traditional Rental Income: $0 Airbnb ROI: 0.47% Traditional ROI: N/A
607 Melvin Ave Annapolis, MD Open House Saturday July 11th, 11AM - 1PM! Come Join us to see this adorable bungalow in a...	2 beds \| 2 baths \| 1,102 sq.ft.	$899,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 0.66% Airbnb Rental Income: $1908 Traditional Rental Income: $2253 Airbnb ROI: -0.36% Traditional ROI: 0.66%
1254 Washington Dr Annapolis, MD Rare waterfront redevelopment opportunity in Annapolis. The existing structure is a comple...	5 beds \| 4 baths \| 9,960 sq.ft.	$960,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 3.33% Airbnb Rental Income: $2481 Traditional Rental Income: $5132 Airbnb ROI: -0.17% Traditional ROI: 3.33%
16 Woodlawn Ave Annapolis, MD Are you looking for a beautiful home in beautiful Annapolis, MD? This home has it all! The...	3 beds \| 2 baths \| 1,512 sq.ft.	$799,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 2.08% Airbnb Rental Income: $2689 Traditional Rental Income: $2990 Airbnb ROI: 0.88% Traditional ROI: 2.08%
1915 Towne Centre Blvd #303 Annapolis, MD Discover a luxurious lifestyle in this exquisite 2-bedroom, 2-bathroom residence nestled i...	2 beds \| 2 baths \| 1,602 sq.ft.	$599,000	Airbnb cash on cash: -2.37% Traditional cash on cash: -1.3% Airbnb Rental Income: $1908 Traditional Rental Income: $2024 Airbnb ROI: -2.37% Traditional ROI: -1.3%
425 Blossom Tree Ct Annapolis, MD No more looking around!! Stunning Twin/Semi-Detached with 3 levels located in Whispering W...	4 beds \| 3 baths \| 1,670 sq.ft.	$425,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 6% Airbnb Rental Income: $3333 Traditional Rental Income: $3167 Airbnb ROI: 4.54% Traditional ROI: 6%
5 PRESIDENT POINT Drive #A2 Annapolis, MD Welcome to waterfront living at The Point, one of Annapolis' most desirable communities on...	1 beds \| 1 baths \| 923 sq.ft.	$799,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 0.45% Airbnb Rental Income: $1593 Traditional Rental Income: $1944 Airbnb ROI: -0.63% Traditional ROI: 0.45%
924 Shipmaster Ct Annapolis, MD Enjoy easy, one-level living in this beautifully maintained end-unit home in Heritage Harb...	2 beds \| 2 baths \| 1,634 sq.ft.	$540,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 1.94% Airbnb Rental Income: $1908 Traditional Rental Income: $2024 Airbnb ROI: 0.71% Traditional ROI: 1.94%
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.	$675,000	Airbnb cash on cash: -2.22% Traditional cash on cash: -0.12% Airbnb Rental Income: $1908 Traditional Rental Income: $2724 Airbnb ROI: -2.22% Traditional ROI: -0.12%
1107 COMMANDERS Way S Annapolis, MD Discover the perfect combination of value, comfort, and convenience in this beautifully up...	3 beds \| 2 baths \| 1,200 sq.ft.	$360,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 6.45% Airbnb Rental Income: $2689 Traditional Rental Income: $2990 Airbnb ROI: 3.67% Traditional ROI: 6.45%
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: $2689 Traditional Rental Income: $2887 Airbnb ROI: -1.15% Traditional ROI: -0.89%
602 James Walker Pl Annapolis, MD Location! Location! Location! Nestled in the vibrant heart of Annapolis Towne Center, this...	3 beds \| 3 baths \| 2,272 sq.ft.	$579,900	Airbnb cash on cash: 0.95% Traditional cash on cash: 4.12% Airbnb Rental Income: $2689 Traditional Rental Income: $3787 Airbnb ROI: 0.95% Traditional ROI: 4.12%
1055 Sun Valley Dr Annapolis, MD This charming colonial home is located in Cape St. Claire and offers 3 bedrooms, 2.5 baths...	3 beds \| 2 baths \| 2,050 sq.ft.	$565,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 3.65% Airbnb Rental Income: $2689 Traditional Rental Income: $2990 Airbnb ROI: 1.93% Traditional ROI: 3.65%

Real Estate investment in Annapolis, MD

There are 383 properties for sale in the city of Annapolis . The median list price in Annapolis is $597,392 and the average price per square foot is $233. In October 2026, the average monthly cash on cash return in Annapolis is 1.00%. The average monthly rental income in Annapolis is $2,430.

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

There are 383 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 $2,481.

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: -1.93%

Traditional cash on cash: -1.57%

Airbnb Rental Income: $2481

Traditional Rental Income: $6094

Airbnb ROI: -1.93%

Traditional ROI: -1.57%

5 Park Pl #431

Annapolis, MD

1 beds | 1 baths | 839 sq.ft.

$475,000

Airbnb cash on cash: -1.88%

Traditional cash on cash: -0.01%

Airbnb Rental Income: $1593

Traditional Rental Income: $1969

Airbnb ROI: -1.88%

Traditional ROI: -0.01%

19 Boucher Pl

Annapolis, MD

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

$799,000

Airbnb cash on cash: 0.27%

Traditional cash on cash: 1.26%

Airbnb Rental Income: $2689

Traditional Rental Income: $2791

Airbnb ROI: 0.27%

Traditional ROI: 1.26%

66 FRANKLIN ST #20

Annapolis, MD

1 beds | 2 baths | N/A

$725,000

Airbnb cash on cash: -2.08%

Traditional cash on cash: -0.43%

Airbnb Rental Income: $1593

Traditional Rental Income: $2248

Airbnb ROI: -2.08%

Traditional ROI: -0.43%

5 Park Pl #414

Annapolis, MD

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

$564,900

Airbnb cash on cash: -1.75%

Traditional cash on cash: -0.57%

Airbnb Rental Income: $1908

Traditional Rental Income: $2024

Airbnb ROI: -1.75%

Traditional ROI: -0.57%

11 S Acton Pl

Annapolis, MD

4 beds | 3 baths | 3,658 sq.ft.

$7,250,000

Airbnb cash on cash: -0.93%

Traditional cash on cash: -0.87%

Airbnb Rental Income: $3333

Traditional Rental Income: $3010

Airbnb ROI: -0.93%

Traditional ROI: -0.87%

2102 Chesapeake Harbour Dr E #202

Annapolis, MD

3 beds | 3 baths | 1,666 sq.ft.

$675,000

Airbnb cash on cash: -0.36%

Traditional cash on cash: 0.69%

Airbnb Rental Income: $2689

Traditional Rental Income: $2723

Airbnb ROI: -0.36%

Traditional ROI: 0.69%

110 Lake View Dr

Annapolis, MD

3 beds | 2 baths | 2,242 sq.ft.

$720,000

Airbnb cash on cash: 1.34%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $2689

Traditional Rental Income: $2470

Airbnb ROI: 1.34%