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
1915 TOWNE CENTRE BOULEVARD #807 Annapolis, MD PRICE IMPROVEMENT!! COSMOPOLITAN 2BR/2BA CONDO in the GRANDVIEW at TOWNE CENTRE! Condo com...	2 beds \| 2 baths \| 1,246 sq.ft.	$585,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 2.78% Airbnb Rental Income: $2330 Traditional Rental Income: $2694 Airbnb ROI: 1.06% Traditional ROI: 2.78%
66 FRANKLIN ST #20 Annapolis, MD Chic Street-Level Condo in the Heart of Annapolis. Welcome to this spacious 1-bedroom, 1.5...	1 beds \| 2 baths \| N/A	$750,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 1.09% Airbnb Rental Income: $1691 Traditional Rental Income: $2248 Airbnb ROI: -0.38% Traditional ROI: 1.09%
2026 GOV THOMAS BLADEN WAY #102 Annapolis, MD This 3 bed / 2 bath condo has everything you need a cozy fireplace, spacious layout, and n...	3 beds \| 2 baths \| 1,317 sq.ft.	$389,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 2.88% Airbnb Rental Income: $2518 Traditional Rental Income: $2320 Airbnb ROI: 1.75% Traditional ROI: 2.88%
5 PARK PLACE #107 Annapolis, MD Enjoy luxury condo living in this first-floor 2-bedroom, 2-bath home. Featuring gleaming h...	2 beds \| 2 baths \| 1,272 sq.ft.	$625,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 2.1% Airbnb Rental Income: $2330 Traditional Rental Income: $2551 Airbnb ROI: 0.73% Traditional ROI: 2.1%
1136 LAKE HERON DRIVE #3A Annapolis, MD Two spacious bedrooms and two beautifully appointed bathrooms anchor this stunning home. A...	2 beds \| 2 baths \| 1,412 sq.ft.	$410,000	Airbnb cash on cash: 2.22% Traditional cash on cash: 4.09% Airbnb Rental Income: $2330 Traditional Rental Income: $2469 Airbnb ROI: 2.22% Traditional ROI: 4.09%
1230 CRUMMELL AVENUE Annapolis, MD A peaceful retreat where calm waters set the stage for your everyday getaway. Imagine step...	4 beds \| 3 baths \| 2,555 sq.ft.	$1,225,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 1.2% Airbnb Rental Income: $3084 Traditional Rental Income: $3443 Airbnb ROI: 0.27% Traditional ROI: 1.2%
52 PRIMROSE HILL LANE Annapolis, MD Welcome to 52 Primrose Hill Lane, the original model home in Craftmarks Primrose Hill comm...	5 beds \| 5 baths \| 3,978 sq.ft.	$985,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 3.16% Airbnb Rental Income: $3750 Traditional Rental Income: $5022 Airbnb ROI: 0.88% Traditional ROI: 3.16%
1634 ORCHARD BEACH ROAD Annapolis, MD An incredible opportunity with endless potential awaits! This 3-bedroom, 3-bath home sits ...	3 beds \| 3 baths \| 2,868 sq.ft.	$930,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 2.08% Airbnb Rental Income: $2518 Traditional Rental Income: $3336 Airbnb ROI: 0.43% Traditional ROI: 2.08%
1834 SAINT MARGARETS RD Annapolis, MD Set on nearly an acre in the rolling hills of Saint Margaret's, this one-level home combin...	3 beds \| 1 baths \| N/A	$475,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 1.83% Airbnb Rental Income: $2518 Traditional Rental Income: $1851 Airbnb ROI: 1.96% Traditional ROI: 1.83%
3182 HARNESS CREEK ROAD Annapolis, MD Experience sweeping waterfront vistas and unforgettable sunsets from this never-lived-in, ...	4 beds \| 6 baths \| 5,375 sq.ft.	$11,500,000	Airbnb cash on cash: -0.91% Traditional cash on cash: -0.42% Airbnb Rental Income: $3084 Traditional Rental Income: $7639 Airbnb ROI: -0.91% Traditional ROI: -0.42%
1192 BAY HIGHLANDS DRIVE Annapolis, MD Welcome to this generously spacious 4-bedroom, 2.5-bathroom home that blends comfort, char...	4 beds \| 3 baths \| 2,200 sq.ft.	$685,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 3.3% Airbnb Rental Income: $3084 Traditional Rental Income: $3363 Airbnb ROI: 1.77% Traditional ROI: 3.3%
103 NORMA ALLEY Annapolis, MD Welcome to this stunning, light-filled, and modern four-bedroom townhome located in the pr...	4 beds \| 5 baths \| 1,880 sq.ft.	$695,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 3.17% Airbnb Rental Income: $3084 Traditional Rental Income: $3727 Airbnb ROI: 1.1% Traditional ROI: 3.17%
2026 GOV THOMAS BLADEN WAY #203 Annapolis, MD Welcome to your new home! This beautifully maintained property offers an open-concept floo...	2 beds \| 2 baths \| 1,006 sq.ft.	$368,000	Airbnb cash on cash: 3.06% Traditional cash on cash: 4.04% Airbnb Rental Income: $2330 Traditional Rental Income: $2089 Airbnb ROI: 3.06% Traditional ROI: 4.04%
66 FRANKLIN STREET #509 Annapolis, MD Gorgeous, One-of-a-Kind Luxury Penthouse in Downtown Annapolis! Welcome to this stunning 3...	3 beds \| 4 baths \| 2,477 sq.ft.	$1,850,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 0.05% Airbnb Rental Income: $2518 Traditional Rental Income: $3393 Airbnb ROI: -0.81% Traditional ROI: 0.05%
633 BAYSTONE CT Annapolis, MD Welcome to easy living on the Broadneck Peninsula! This three-level garage townhome blends...	3 beds \| 2 baths \| N/A	$469,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 4.09% Airbnb Rental Income: $2518 Traditional Rental Income: $2717 Airbnb ROI: 2.25% Traditional ROI: 4.09%
39 WINDWHISPER LN Annapolis, MD Tucked away on a peaceful cul-de-sac in the desirable Georgetown Grove community, this bea...	3 beds \| 4 baths \| N/A	$700,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 2.91% Airbnb Rental Income: $2518 Traditional Rental Income: $3397 Airbnb ROI: 0.63% Traditional ROI: 2.91%
100 SUNSET DR Annapolis, MD Welcome to your coastal dream home! Perfectly positioned just one block from the community...	4 beds \| 3 baths \| N/A	$915,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 2.02% Airbnb Rental Income: $3084 Traditional Rental Income: $3380 Airbnb ROI: 0.84% Traditional ROI: 2.02%
930 ASTERN WAY #609 Annapolis, MD Contemporary and beautifully maintained, this 2 bedroom, 2.5 bath penthouse condominium of...	2 beds \| 3 baths \| 1,926 sq.ft.	$450,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 4.22% Airbnb Rental Income: $2330 Traditional Rental Income: $2912 Airbnb ROI: 1.47% Traditional ROI: 4.22%
1096 LINDEN TREE DR Annapolis, MD Large double Lot with tons of potential - 2 Lots included in this sale 1096 (Lot 4) and 1...	3 beds \| 1 baths \| N/A	$535,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 3.73% Airbnb Rental Income: $2518 Traditional Rental Income: $2896 Airbnb ROI: 1.76% Traditional ROI: 3.73%
8 ASHFORD CT Annapolis, MD Price Adjustment! Welcome to 8 Ashford Ct - Modern Living in the Heart of Annapolis! Now o...	2 beds \| 2 baths \| N/A	$465,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 2.41% Airbnb Rental Income: $2330 Traditional Rental Income: $2034 Airbnb ROI: 1.76% Traditional ROI: 2.41%
547 LEFTWICH LN #88 Annapolis, MD COSMOPOLITAN ANNAPOLIS TOWNHOME BOASTING SKYLINE ROOFTOP DECK! ADMIRALS SQUARE DUAL ASPEC...	3 beds \| 3 baths \| N/A	$589,999	Airbnb cash on cash: 1.33% Traditional cash on cash: 3.26% Airbnb Rental Income: $2518 Traditional Rental Income: $2973 Airbnb ROI: 1.33% Traditional ROI: 3.26%
237 HANOVER ST Annapolis, MD This is a rare opportunity to own a well-documented (MHA) Greek Revival home on quiet Han...	3 beds \| 3 baths \| N/A	$1,295,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 0.29% Airbnb Rental Income: $2518 Traditional Rental Income: $2672 Airbnb ROI: -0.34% Traditional ROI: 0.29%
2900 SHIPMASTER WAY #211 Annapolis, MD NEW PRICE Welcome to your Annapolis retreatUnit #211 is a bright and breezy 2-bedroom,...	2 beds \| 2 baths \| 1,154 sq.ft.	$344,900	Airbnb cash on cash: 2.98% Traditional cash on cash: 4.24% Airbnb Rental Income: $2330 Traditional Rental Income: $2162 Airbnb ROI: 2.98% Traditional ROI: 4.24%
1034 SAINT MARGARETS DR Annapolis, MD Welcome home to this well maintained four bedroom, two and a half bath property in sought ...	4 beds \| 3 baths \| N/A	$575,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 4.19% Airbnb Rental Income: $3084 Traditional Rental Income: $3333 Airbnb ROI: 2.42% Traditional ROI: 4.19%
1624 KATHERYNE VILLAGE SQ Annapolis, MD Welcome to 1624 Katheryne Village Sq- This beautifully updated 4 bed/3 full bath townhome...	4 beds \| 4 baths \| N/A	$489,900	Airbnb cash on cash: 3.08% Traditional cash on cash: 5.29% Airbnb Rental Income: $3084 Traditional Rental Income: $3396 Airbnb ROI: 3.08% Traditional ROI: 5.29%
5 PARK PLACE #428 Annapolis, MD Experience luxury and light in this rare 3-bedroom, 2.5-bath condo in the highly sought-af...	3 beds \| 3 baths \| 1,822 sq.ft.	$1,099,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 0.56% Airbnb Rental Income: $2518 Traditional Rental Income: $2797 Airbnb ROI: -0.31% Traditional ROI: 0.56%
25 DORSEY AVENUE Annapolis, MD Modern Cape Cod style home located near everything Annapolis has to offer! It's just minut...	4 beds \| 3 baths \| 1,820 sq.ft.	$525,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 6.59% Airbnb Rental Income: $3084 Traditional Rental Income: $4234 Airbnb ROI: 2.82% Traditional ROI: 6.59%
2022 SAMS WAY #12A Annapolis, MD Waterfront Townhouse in Chesapeake Harbour Your search ends here! This mint-condition, ful...	2 beds \| 3 baths \| 1,923 sq.ft.	$675,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 2.26% Airbnb Rental Income: $2330 Traditional Rental Income: $3045 Airbnb ROI: 0.2% Traditional ROI: 2.26%
144 ISLAND VIEW DRIVE Annapolis, MD MOTIVATED SELLER! This home sits on almost a half-acre wooded lot in a quiet, family-frien...	4 beds \| 3 baths \| 1,612 sq.ft.	$615,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 1.97% Airbnb Rental Income: $3084 Traditional Rental Income: $2317 Airbnb ROI: 2.08% Traditional ROI: 1.97%
1411 STONECREEK RD Annapolis, MD Nicely renovated single family contemporary in sought after Stonecreek (The Landings). 4 b...	4 beds \| 4 baths \| N/A	$575,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 4.82% Airbnb Rental Income: $3084 Traditional Rental Income: $3771 Airbnb ROI: 2.23% Traditional ROI: 4.82%
400 JEFFERSON STREET Annapolis, MD Custom coastal craftsman home is currently under construction in Eastport - Annapolis, Mar...	4 beds \| 3 baths \| 3,640 sq.ft.	$1,700,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 0.81% Airbnb Rental Income: $3084 Traditional Rental Income: $3405 Airbnb ROI: 0.16% Traditional ROI: 0.81%
5 EDGEWOOD GREEN COURT Annapolis, MD Affordably priced GEM! Wonderful 3 bed 2.5 bath town home in an exceptional location in de...	3 beds \| 3 baths \| 1,368 sq.ft.	$395,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 4.22% Airbnb Rental Income: $2518 Traditional Rental Income: $2701 Airbnb ROI: 2.08% Traditional ROI: 4.22%
2707 JUDSON PLACE Annapolis, MD Welcome to 2707 Judson Place in Riva Woods. This inviting home sits on a private, fenced c...	3 beds \| 3 baths \| 2,156 sq.ft.	$600,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 3.62% Airbnb Rental Income: $2518 Traditional Rental Income: $3172 Airbnb ROI: 1.37% Traditional ROI: 3.62%
1 TUCKER STREET Annapolis, MD Incredible West Annapolis home that has been renovated from top to bottom with high end fi...	3 beds \| 3 baths \| 1,869 sq.ft.	$1,175,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 1% Airbnb Rental Income: $2518 Traditional Rental Income: $3155 Airbnb ROI: -0.14% Traditional ROI: 1%
198 CLAY STREET Annapolis, MD Welcome to 198 Clay Street in the heart of Annapolis! This charming row home offers water ...	2 beds \| 2 baths \| 902 sq.ft.	$429,000	Airbnb cash on cash: 2.47% Traditional cash on cash: 3.14% Airbnb Rental Income: $2330 Traditional Rental Income: $2021 Airbnb ROI: 2.47% Traditional ROI: 3.14%
1809 LABROTT LANE Annapolis, MD Great SFH situated on flag lot in desirable location! Multiple living spaces on main level...	3 beds \| 4 baths \| 2,236 sq.ft.	$570,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 5.26% Airbnb Rental Income: $2518 Traditional Rental Income: $3966 Airbnb ROI: 1.39% Traditional ROI: 5.26%
1915 TOWNE CENTRE BOULEVARD #301 Annapolis, MD This impeccably maintained 2-bedroom, 2.5-bath Everest floor plan offers high-end living, ...	2 beds \| 3 baths \| 1,684 sq.ft.	$625,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 2.21% Airbnb Rental Income: $2330 Traditional Rental Income: $2599 Airbnb ROI: 0.76% Traditional ROI: 2.21%
106 STILLY WAY Annapolis, MD This stunning home is move-in ready and boasts high-end upgrades throughout. It features a...	4 beds \| 5 baths \| 4,594 sq.ft.	$984,990	Airbnb cash on cash: 1.23% Traditional cash on cash: 3.74% Airbnb Rental Income: $3084 Traditional Rental Income: $4686 Airbnb ROI: 1.23% Traditional ROI: 3.74%
1005 TIMBER CREEK DRIVE Annapolis, MD Welcome to 1005 Timber Creek Dr, where timeless comfort meets nearly $200,000 in recent u...	3 beds \| 3 baths \| 1,826 sq.ft.	$609,900	Airbnb cash on cash: 1.19% Traditional cash on cash: 3.64% Airbnb Rental Income: $2518 Traditional Rental Income: $3303 Airbnb ROI: 1.19% Traditional ROI: 3.64%
730 CRISFIELD WAY Annapolis, MD Stunning 5BR/4.5BA Luxury Home Grand residence featuring hardwood foyer, formal oval dinin...	5 beds \| 5 baths \| N/A	$899,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 3% Airbnb Rental Income: $3750 Traditional Rental Income: $4276 Airbnb ROI: 1.4% Traditional ROI: 3%

Real Estate investment in Annapolis, MD

There are 229 properties for sale in the city of Annapolis . The median list price in Annapolis is $699,450 and the average price per square foot is $262. In September 2025, the average monthly cash on cash return in Annapolis is 2.00%. The average monthly rental income in Annapolis is $2,852.

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

There are 229 investment properties available for sale in Annapolis.

In 2025, the best neighborhood to buy investment property is Annapolis.

The ROI for Long-Term is higher than the Short-Term in Annapolis with average rental income of $2,852.

Your search for investment property begins and ends here

Investment Property for Sale in Annapolis, MD

1915 TOWNE CENTRE BOULEVARD #807

Annapolis, MD

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

$585,000

Airbnb cash on cash: 1.06%

Traditional cash on cash: 2.78%

Airbnb Rental Income: $2330

Traditional Rental Income: $2694

Airbnb ROI: 1.06%

Traditional ROI: 2.78%

66 FRANKLIN ST #20

Annapolis, MD

1 beds | 2 baths | N/A

$750,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 1.09%

Airbnb Rental Income: $1691

Traditional Rental Income: $2248

Airbnb ROI: -0.38%

Traditional ROI: 1.09%

2026 GOV THOMAS BLADEN WAY #102

Annapolis, MD

3 beds | 2 baths | 1,317 sq.ft.

$389,000

Airbnb cash on cash: 1.75%

Traditional cash on cash: 2.88%

Airbnb Rental Income: $2518

Traditional Rental Income: $2320

Airbnb ROI: 1.75%

Traditional ROI: 2.88%

5 PARK PLACE #107

Annapolis, MD

2 beds | 2 baths | 1,272 sq.ft.

$625,000

Airbnb cash on cash: 0.73%

Traditional cash on cash: 2.1%

Airbnb Rental Income: $2330

Traditional Rental Income: $2551

Airbnb ROI: 0.73%

Traditional ROI: 2.1%

1136 LAKE HERON DRIVE #3A

Annapolis, MD

2 beds | 2 baths | 1,412 sq.ft.

$410,000

Airbnb cash on cash: 2.22%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $2330

Traditional Rental Income: $2469

Airbnb ROI: 2.22%

Traditional ROI: 4.09%

1230 CRUMMELL AVENUE

Annapolis, MD

4 beds | 3 baths | 2,555 sq.ft.

$1,225,000

Airbnb cash on cash: 0.27%

Traditional cash on cash: 1.2%

Airbnb Rental Income: $3084

Traditional Rental Income: $3443

Airbnb ROI: 0.27%

Traditional ROI: 1.2%

52 PRIMROSE HILL LANE

Annapolis, MD

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

$985,000

Airbnb cash on cash: 0.88%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $3750

Traditional Rental Income: $5022

Airbnb ROI: 0.88%

Traditional ROI: 3.16%

1634 ORCHARD BEACH ROAD

Annapolis, MD

3 beds | 3 baths | 2,868 sq.ft.

$930,000

Airbnb cash on cash: 0.43%

Traditional cash on cash: 2.08%

Airbnb Rental Income: $2518

Traditional Rental Income: $3336

Airbnb ROI: 0.43%