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: $2512 Traditional Rental Income: $6094 Airbnb ROI: -1.93% 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...	3 beds \| 2 baths \| 1,720 sq.ft.	$750,000	Airbnb cash on cash: 1.09% Traditional cash on cash: 1.93% Airbnb Rental Income: $2603 Traditional Rental Income: $2567 Airbnb ROI: 1.09% Traditional ROI: 1.93%
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: -2.05% Traditional cash on cash: -0.01% Airbnb Rental Income: $1502 Traditional Rental Income: $1969 Airbnb ROI: -2.05% Traditional ROI: -0.01%
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.	$799,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 1.45% Airbnb Rental Income: $2603 Traditional Rental Income: $2791 Airbnb ROI: 0.38% Traditional ROI: 1.45%
2978 Valley View Rd Annapolis, MD Nestled in the highly sought-after, water-privileged community of Cape St. John, this exce...	4 beds \| 3 baths \| 2,553 sq.ft.	$950,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 1.75% Airbnb Rental Income: $2683 Traditional Rental Income: $3269 Airbnb ROI: 0.4% Traditional ROI: 1.75%
1016 Timber Creek Dr Annapolis, MD Welcome to 1016 Timber Creek Drive, a well maintained home nestled in the sought-after Tim...	3 beds \| 3 baths \| 1,730 sq.ft.	$575,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 2.75% Airbnb Rental Income: $2603 Traditional Rental Income: $2798 Airbnb ROI: 1.26% Traditional ROI: 2.75%
1915 Towne Centre Blvd #1105 Annapolis, MD The only 3,400 sqft penthouse under $600/sqft in Annapolis, with 11ft ceilings, dual balco...	3 beds \| 3 baths \| 3,368 sq.ft.	$1,650,000	Airbnb cash on cash: -2.28% Traditional cash on cash: -1.97% Airbnb Rental Income: $2603 Traditional Rental Income: $2456 Airbnb ROI: -2.28% Traditional ROI: -1.97%
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: -2.19% Traditional cash on cash: -0.43% Airbnb Rental Income: $1502 Traditional Rental Income: $2248 Airbnb ROI: -2.19% 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.	$7,250,000	Airbnb cash on cash: -1.01% Traditional cash on cash: -0.87% Airbnb Rental Income: $2683 Traditional Rental Income: $3010 Airbnb ROI: -1.01% Traditional ROI: -0.87%
110 Lake View Dr Annapolis, MD Beautiful home on a corner lot in desirable WATER privileged community of Hillsmere Estate...	3 beds \| 2 baths \| 1,742 sq.ft.	$740,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 2.65% Airbnb Rental Income: $2603 Traditional Rental Income: $3013 Airbnb ROI: 1.18% Traditional ROI: 2.65%
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: -2.19% Traditional cash on cash: 0.76% Airbnb Rental Income: $1822 Traditional Rental Income: $2844 Airbnb ROI: -2.19% 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.	$545,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 0.64% Airbnb Rental Income: $1822 Traditional Rental Income: $2248 Airbnb ROI: -1.06% Traditional ROI: 0.64%
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: 0.27% Traditional cash on cash: 0.39% Airbnb Rental Income: $1822 Traditional Rental Income: $1402 Airbnb ROI: 0.27% Traditional ROI: 0.39%
349 EPPING WAY Annapolis, MD Major price reduction, exceptional value for over 3,292 finished sq ft tucked among the tr...	4 beds \| 3 baths \| N/A	$925,000	Airbnb cash on cash: 0.08% Traditional cash on cash: -1.41% Airbnb Rental Income: $2683 Traditional Rental Income: $763 Airbnb ROI: 0.08% Traditional ROI: -1.41%
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.	$830,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 2.46% Airbnb Rental Income: $2683 Traditional Rental Income: $3524 Airbnb ROI: 0.59% Traditional ROI: 2.46%
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: -1.03% Traditional cash on cash: -0.91% Airbnb Rental Income: $2603 Traditional Rental Income: $2613 Airbnb ROI: -1.03% Traditional ROI: -0.91%
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: -0.22% Traditional cash on cash: 0.43% Airbnb Rental Income: $2683 Traditional Rental Income: $2722 Airbnb ROI: -0.22% Traditional ROI: 0.43%
1365 Moyer Rd Annapolis, MD Welcome to 1365 Moyer Road, a beautifully renovated home offering the perfect blend of mod...	4 beds \| 3 baths \| 1,814 sq.ft.	$609,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 2.74% Airbnb Rental Income: $2683 Traditional Rental Income: $2768 Airbnb ROI: 1.49% Traditional ROI: 2.74%
707 Shelton Ave Annapolis, MD INVESTOR ALERT! Turn-Key Rental! Tenant Occupied till May 31st 2021. Professional Managem...	4 beds \| 3 baths \| 2,600 sq.ft.	$649,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 2.77% Airbnb Rental Income: $2683 Traditional Rental Income: $2834 Airbnb ROI: 1.47% Traditional ROI: 2.77%
3280 Arundel On The Bay Rd Annapolis, MD Welcome to this beautifully maintained custom built Tudor Style home in this small coastal...	5 beds \| 4 baths \| 3,144 sq.ft.	$799,900	Airbnb cash on cash: 0.54% Traditional cash on cash: 4.54% Airbnb Rental Income: $2512 Traditional Rental Income: $4883 Airbnb ROI: 0.54% Traditional ROI: 4.54%
219 Lockwood Ct Annapolis, MD EASTPORT! Beautiful historic Annapolis & Spa Creek views -- all the way down to the Severn...	4 beds \| 4 baths \| 1,848 sq.ft.	$1,750,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 0.11% Airbnb Rental Income: $2683 Traditional Rental Income: $3351 Airbnb ROI: -0.7% Traditional ROI: 0.11%
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: -0.44% Traditional cash on cash: 0.66% Airbnb Rental Income: $1822 Traditional Rental Income: $2253 Airbnb ROI: -0.44% Traditional ROI: 0.66%
1006 Primrose Rd #303 Annapolis, MD	3 beds \| 2 baths \| 1,253 sq.ft.	$379,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 2.43% Airbnb Rental Income: $2603 Traditional Rental Income: $2266 Airbnb ROI: 1.63% Traditional ROI: 2.43%
1709 Point No Point Dr Annapolis, MD Major $25,000 price improvement - an incredible opportunity to own a private contemporary ...	4 beds \| 2 baths \| 2,464 sq.ft.	$750,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 1.71% Airbnb Rental Income: $2683 Traditional Rental Income: $2775 Airbnb ROI: 0.7% Traditional ROI: 1.71%
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: -0.14% Traditional cash on cash: 3.33% Airbnb Rental Income: $2512 Traditional Rental Income: $5132 Airbnb ROI: -0.14% Traditional ROI: 3.33%
103 Norma Aly Annapolis, MD Welcome to Primrose Hill, one of Annapolis' most desirable hidden gems, where modern luxur...	4 beds \| 3 baths \| 2,500 sq.ft.	$699,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 3.01% Airbnb Rental Income: $2683 Traditional Rental Income: $3727 Airbnb ROI: 0.44% Traditional ROI: 3.01%
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: -2.3% Traditional cash on cash: -0.15% Airbnb Rental Income: $1822 Traditional Rental Income: $2724 Airbnb ROI: -2.3% 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 \| N/A	$654,900	Airbnb cash on cash: -2.06% Traditional cash on cash: -0.58% Airbnb Rental Income: $1822 Traditional Rental Income: $2234 Airbnb ROI: -2.06% Traditional ROI: -0.58%
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: -1.17% Traditional cash on cash: -0.89% Airbnb Rental Income: $2603 Traditional Rental Income: $2887 Airbnb ROI: -1.17% 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.	$589,900	Airbnb cash on cash: 0.77% Traditional cash on cash: 4% Airbnb Rental Income: $2603 Traditional Rental Income: $3787 Airbnb ROI: 0.77% Traditional ROI: 4%
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 \| 4 baths \| N/A	$550,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 4.14% Airbnb Rental Income: $2603 Traditional Rental Income: $3299 Airbnb ROI: 1.57% Traditional ROI: 4.14%
3268 Kitty Duvall Dr Annapolis, MD Our Adams model with a 2' extenstion will be built at this beautiful location near Duvall ...	4 beds \| 2 baths \| 2,474 sq.ft.	$849,990	Airbnb cash on cash: 1.11% Traditional cash on cash: 2.81% Airbnb Rental Income: $2683 Traditional Rental Income: $3393 Airbnb ROI: 1.11% Traditional ROI: 2.81%
418 Chesapeake Ave Annapolis, MD Quintessential Eastport charm in this sought-after Lower Eastport location. A welcoming fr...	2 beds \| 1 baths \| 1,128 sq.ft.	$825,000	Airbnb cash on cash: -0.85% Traditional cash on cash: -0.47% Airbnb Rental Income: $1822 Traditional Rental Income: $1627 Airbnb ROI: -0.85% Traditional ROI: -0.47%

Real Estate investment in Annapolis, MD

There are 392 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 $236. In August 2026, the average monthly cash on cash return in Annapolis is 1.00%. The average monthly rental income in Annapolis is $2,476.

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

There are 392 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 $2,512.

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: $2512

Traditional Rental Income: $6094

Airbnb ROI: -1.93%

Traditional ROI: -1.57%

1100 Bay Ridge Ave

Annapolis, MD

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

$750,000

Airbnb cash on cash: 1.09%

Traditional cash on cash: 1.93%

Airbnb Rental Income: $2603

Traditional Rental Income: $2567

Airbnb ROI: 1.09%

Traditional ROI: 1.93%

5 Park Pl #431

Annapolis, MD

1 beds | 1 baths | 839 sq.ft.

$475,000

Airbnb cash on cash: -2.05%

Traditional cash on cash: -0.01%

Airbnb Rental Income: $1502

Traditional Rental Income: $1969

Airbnb ROI: -2.05%

Traditional ROI: -0.01%

19 Boucher Pl

Annapolis, MD

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

$799,000

Airbnb cash on cash: 0.38%

Traditional cash on cash: 1.45%

Airbnb Rental Income: $2603

Traditional Rental Income: $2791

Airbnb ROI: 0.38%

Traditional ROI: 1.45%

2978 Valley View Rd

Annapolis, MD

4 beds | 3 baths | 2,553 sq.ft.

$950,000

Airbnb cash on cash: 0.4%

Traditional cash on cash: 1.75%

Airbnb Rental Income: $2683

Traditional Rental Income: $3269

Airbnb ROI: 0.4%

Traditional ROI: 1.75%

1016 Timber Creek Dr

Annapolis, MD

3 beds | 3 baths | 1,730 sq.ft.

$575,000

Airbnb cash on cash: 1.26%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $2603

Traditional Rental Income: $2798

Airbnb ROI: 1.26%

Traditional ROI: 2.75%

1915 Towne Centre Blvd #1105

Annapolis, MD

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

$1,650,000

Airbnb cash on cash: -2.28%

Traditional cash on cash: -1.97%

Airbnb Rental Income: $2603

Traditional Rental Income: $2456

Airbnb ROI: -2.28%

Traditional ROI: -1.97%

66 Franklin St #20

Annapolis, MD

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

$725,000

Airbnb cash on cash: -2.19%

Traditional cash on cash: -0.43%

Airbnb Rental Income: $1502

Traditional Rental Income: $2248

Airbnb ROI: -2.19%