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
1090 BROADVIEW DR Annapolis, MD Welcome home to this cozy four bedroom, two full bath split foyer in sought after Cape St ...	4 beds \| 2 baths \| N/A	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.36% Airbnb Rental Income: $null Traditional Rental Income: $2771 Airbnb ROI: N/A Traditional ROI: 3.36%
190 Duke Of Gloucester St Annapolis, MD Historic charm and everyday comfort come together beautifully in this spacious Victorian i...	4 beds \| 3 baths \| 3,393 sq.ft.	$1,500,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.88% Airbnb Rental Income: $null Traditional Rental Income: $5080 Airbnb ROI: N/A Traditional ROI: 1.88%
52 PRIMROSE HILL Lane Annapolis, MD Modern accents meet classic Georgian design in a downtown Annapolis private enclave of cus...	5 beds \| 5 baths \| 3,978 sq.ft.	$924,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.31% Airbnb Rental Income: $null Traditional Rental Income: $5022 Airbnb ROI: N/A Traditional ROI: 3.31%
3280 Arundel On The Bay Rd Annapolis, MD Significant Price Improvement!! A rare opportunity! Priced to sell, won't last long. Welco...	5 beds \| 4 baths \| 3,144 sq.ft.	$850,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.21% Airbnb Rental Income: $null Traditional Rental Income: $4883 Airbnb ROI: N/A Traditional ROI: 4.21%
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.	$1,529,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.47% Airbnb Rental Income: $null Traditional Rental Income: $4864 Airbnb ROI: N/A Traditional ROI: 1.47%
1576 Saint Margarets Rd Annapolis, MD Welcome to 1576 St. Margaret's Road, a meticulously rebuilt rancher set on a peaceful 1.89...	4 beds \| 2 baths \| 1,792 sq.ft.	$690,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.44% Airbnb Rental Income: $null Traditional Rental Income: $2950 Airbnb ROI: N/A Traditional ROI: 2.44%
930 Astern Way #304 Annapolis, MD Welcome to 930 Astern Way - a spacious and beautifully updated 1-bedroom, 1 1/2-bath condo...	1 beds \| 1 baths \| 1,152 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.13% Airbnb Rental Income: $null Traditional Rental Income: $2070 Airbnb ROI: N/A Traditional ROI: 2.13%
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.	$430,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.24% Airbnb Rental Income: $null Traditional Rental Income: $2363 Airbnb ROI: N/A Traditional ROI: 3.24%
99 Summerfield Dr Annapolis, MD Charming rancher in the heart of Annapolis! Hardwood throughout, updates to the kitchens a...	4 beds \| 3 baths \| 1,980 sq.ft.	$524,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.83% Airbnb Rental Income: $null Traditional Rental Income: $2939 Airbnb ROI: N/A Traditional ROI: 3.83%
310 Giddings Ave Annapolis, MD Welcome to 310 Giddings Avenue, a stunningly re-imagined Craftsman-style home on an expans...	3 beds \| 3 baths \| 3,218 sq.ft.	$1,700,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.42% Airbnb Rental Income: $null Traditional Rental Income: $3351 Airbnb ROI: N/A Traditional ROI: 0.42%
141 West St #201 Annapolis, MD Welcome to 141 West a boutique building styled after one of Manhattan's most iconic neighb...	1 beds \| 1 baths \| 612 sq.ft.	$482,500	Airbnb cash on cash: N/A Traditional cash on cash: 1.49% Airbnb Rental Income: $null Traditional Rental Income: $2190 Airbnb ROI: N/A Traditional ROI: 1.49%
7002 Channel Village Ct #101 Annapolis, MD MOTIVATED SELLER!!!! This is a fabulous unit, and Welcome to Chesapeake Harbour! This beau...	2 beds \| 2 baths \| 1,319 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.8% Airbnb Rental Income: $null Traditional Rental Income: $2002 Airbnb ROI: N/A Traditional ROI: 0.8%
163 Prince George St Annapolis, MD Located on one of the most charming and desirable streets in Historic Annapolis, this beau...	3 beds \| 2 baths \| 2,434 sq.ft.	$1,425,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.14% Airbnb Rental Income: $null Traditional Rental Income: $2654 Airbnb ROI: N/A Traditional ROI: -0.14%
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.	$565,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.45% Airbnb Rental Income: $null Traditional Rental Income: $2932 Airbnb ROI: N/A Traditional ROI: 3.45%
1223 Madison St Annapolis, MD Fully updated 4-bedroom, 2-bath home in the heart of Eastport offering modern finishes, fl...	4 beds \| 2 baths \| 1,488 sq.ft.	$609,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.81% Airbnb Rental Income: $null Traditional Rental Income: $2812 Airbnb ROI: N/A Traditional ROI: 2.81%
316 Burnside St #203 Annapolis, MD Welcome to the sought-after Newport Condominiums in Eastport, where coastal charm meets wa...	1 beds \| 1 baths \| 525 sq.ft.	$482,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.02% Airbnb Rental Income: $null Traditional Rental Income: $1337 Airbnb ROI: N/A Traditional ROI: -0.02%
605 ADMIRAL DR #301 Annapolis, MD HURRY! This location is EVERTHING! Ready for a low-maintenance lifestyle? Experience effor...	2 beds \| 2 baths \| N/A	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.95% Airbnb Rental Income: $null Traditional Rental Income: $2019 Airbnb ROI: N/A Traditional ROI: 1.95%
3 Elliott Rd Annapolis, MD 3 Elliott Road offers a fantastic opportunity to own a well-maintained two-unit duplex wit...	4 beds \| 2 baths \| 2,928 sq.ft.	$745,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.64% Airbnb Rental Income: $null Traditional Rental Income: $3030 Airbnb ROI: N/A Traditional ROI: 2.64%
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: N/A Traditional cash on cash: 0.68% Airbnb Rental Income: $null Traditional Rental Income: $3263 Airbnb ROI: N/A Traditional ROI: 0.68%
2114 Chesapeake Harbour Dr E #202 Annapolis, MD WATCH THE SUNSETS & ENJOY THE BREATHTAKING MARINA VIEWS FROM THIS BEAUTIFUL 3 BEDROOM, 3 F...	3 beds \| 3 baths \| 1,748 sq.ft.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.51% Airbnb Rental Income: $null Traditional Rental Income: $2904 Airbnb ROI: N/A Traditional ROI: 0.51%
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.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.24% Airbnb Rental Income: $null Traditional Rental Income: $2765 Airbnb ROI: N/A Traditional ROI: 3.24%
220 West St Annapolis, MD Welcome to 220 West Street in Annapolis, Maryland. A rare, fully gut-renovated detached pr...	3 beds \| 2 baths \| 1,540 sq.ft.	$924,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.57% Airbnb Rental Income: $null Traditional Rental Income: $2023 Airbnb ROI: N/A Traditional ROI: 0.57%
79 Windwhisper Ln Annapolis, MD Motivated Sellers!! Price Just Improved!! Rare Opportunity in an Amazing Annapolis Neighbo...	4 beds \| 3 baths \| 2,560 sq.ft.	$629,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $3378 Airbnb ROI: N/A Traditional ROI: 3.56%
400 Jefferson St Annapolis, MD Nestled in the heart of historic Eastport Annapolis, this coastal craftsman has been exten...	4 beds \| 3 baths \| 3,640 sq.ft.	$1,990,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.29% Airbnb Rental Income: $null Traditional Rental Income: $3405 Airbnb ROI: N/A Traditional ROI: -0.29%
1176 GREEN HOLLY Drive Annapolis, MD RECENTLY CONSTRUCTED 4 BEDROOM, 2.5 BATH COLONIAL LOCATED IN THE HIGHLY DESIRED WATER-PRIV...	4 beds \| 3 baths \| 2,594 sq.ft.	$889,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.55% Airbnb Rental Income: $null Traditional Rental Income: $3727 Airbnb ROI: N/A Traditional ROI: 2.55%
706 Drake Way Annapolis, MD Experience the best of Annapolis living in this beautifully cared-for Kingsport home, offe...	4 beds \| 4 baths \| 4,571 sq.ft.	$905,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.32% Airbnb Rental Income: $null Traditional Rental Income: $4777 Airbnb ROI: N/A Traditional ROI: 3.32%

Real Estate investment in Annapolis, MD

There are 279 properties for sale in the city of Annapolis . The median list price in Annapolis is $619,950 and the average price per square foot is $287. In April 2026, the average monthly cash on cash return in Annapolis is 1.00%. The average monthly rental income in Annapolis is $2,440.

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

There are 279 investment properties available for sale in Annapolis.

The ROI for Short-Term is higher than the Long-Term in Annapolis with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Annapolis, MD

1090 BROADVIEW DR

Annapolis, MD

4 beds | 2 baths | N/A

$550,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.36%

Airbnb Rental Income: $null

Traditional Rental Income: $2771

Airbnb ROI: N/A

Traditional ROI: 3.36%

190 Duke Of Gloucester St

Annapolis, MD

4 beds | 3 baths | 3,393 sq.ft.

$1,500,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.88%

Airbnb Rental Income: $null

Traditional Rental Income: $5080

Airbnb ROI: N/A

Traditional ROI: 1.88%

52 PRIMROSE HILL Lane

Annapolis, MD

5 beds | 5 baths | 3,978 sq.ft.

$924,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.31%

Airbnb Rental Income: $null

Traditional Rental Income: $5022

Airbnb ROI: N/A

Traditional ROI: 3.31%

3280 Arundel On The Bay Rd

Annapolis, MD

5 beds | 4 baths | 3,144 sq.ft.

$850,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.21%

Airbnb Rental Income: $null

Traditional Rental Income: $4883

Airbnb ROI: N/A

Traditional ROI: 4.21%

1109 Boucher Ave

Annapolis, MD

4 beds | 4 baths | 3,779 sq.ft.

$1,529,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.47%

Airbnb Rental Income: $null

Traditional Rental Income: $4864

Airbnb ROI: N/A

Traditional ROI: 1.47%

1576 Saint Margarets Rd

Annapolis, MD

4 beds | 2 baths | 1,792 sq.ft.

$690,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.44%

Airbnb Rental Income: $null

Traditional Rental Income: $2950

Airbnb ROI: N/A

Traditional ROI: 2.44%

930 Astern Way #304

Annapolis, MD

1 beds | 1 baths | 1,152 sq.ft.

$275,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.13%

Airbnb Rental Income: $null

Traditional Rental Income: $2070

Airbnb ROI: N/A

Traditional ROI: 2.13%

1014 Wells Ave

Annapolis, MD

4 beds | 1 baths | 880 sq.ft.

$430,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.24%

Airbnb Rental Income: $null

Traditional Rental Income: $2363

Airbnb ROI: N/A