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.

Condos for Sale in Annapolis, MD

Search for Condo for Sale in Annapolis, Maryland. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 68 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1915 TOWNE CENTRE Boulevard unit: 807 #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.	$545,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 3.06% Airbnb Rental Income: $2338 Traditional Rental Income: $2694 Airbnb ROI: 1.22% Traditional ROI: 3.06%
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: -0.32% Traditional cash on cash: 1.09% Airbnb Rental Income: $1744 Traditional Rental Income: $2248 Airbnb ROI: -0.32% Traditional ROI: 1.09%
5 PARK Place unit: 107 #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: 0.74% Traditional cash on cash: 2.1% Airbnb Rental Income: $2338 Traditional Rental Income: $2551 Airbnb ROI: 0.74% Traditional ROI: 2.1%
2026 GOV THOMAS BLADEN Way unit: 203 #203 Annapolis, MD Price Reduced!!! Welcome to your new home! This beautifully maintained property offers an ...	2 beds \| 2 baths \| 1,006 sq.ft.	$358,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 4.18% Airbnb Rental Income: $2338 Traditional Rental Income: $2089 Airbnb ROI: 3.2% Traditional ROI: 4.18%
66 FRANKLIN Street unit: 509 #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: -0.73% Traditional cash on cash: 0.05% Airbnb Rental Income: $2680 Traditional Rental Income: $3393 Airbnb ROI: -0.73% Traditional ROI: 0.05%
1915 TOWNE CENTRE BLVD #1004 Annapolis, MD Time to Make a Lifestyle Change - Stunning & Fabulous at The GrandView! Welcome to The Fla...	2 beds \| 2 baths \| N/A	$975,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 1.07% Airbnb Rental Income: $2338 Traditional Rental Income: $2737 Airbnb ROI: -0.01% Traditional ROI: 1.07%
633 BAYSTONE CT Annapolis, MD Price just reduced! Welcome to easy living on the Broadneck Peninsula! This three-level ga...	3 beds \| 2 baths \| N/A	$450,000	Airbnb cash on cash: 2.71% Traditional cash on cash: 4.31% Airbnb Rental Income: $2680 Traditional Rental Income: $2717 Airbnb ROI: 2.71% Traditional ROI: 4.31%
930 ASTERN Way unit: 609 #609 Annapolis, MD Contemporary and beautifully maintained, this 2 bedroom, 2.5 bath penthouse condominium of...	2 beds \| 3 baths \| 1,926 sq.ft.	$425,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 4.53% Airbnb Rental Income: $2338 Traditional Rental Income: $2912 Airbnb ROI: 1.63% Traditional ROI: 4.53%
141 WEST ST #403 Annapolis, MD In the heart of Downtown Annapolis Art District, this Rare, LUXURY PENTHOUSE captures the ...	3 beds \| 3 baths \| N/A	$1,375,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 0.28% Airbnb Rental Income: $2680 Traditional Rental Income: $3160 Airbnb ROI: -0.59% Traditional ROI: 0.28%
547 LEFTWICH LN #88 Annapolis, MD PRiCE IMPROVEMENT! COSMOPOLITAN ANNAPOLIS TOWNHOME BOASTING SKYLINE ROOFTOP DECK! ADMIRAL...	3 beds \| 3 baths \| N/A	$575,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 3.37% Airbnb Rental Income: $2680 Traditional Rental Income: $2973 Airbnb ROI: 1.64% Traditional ROI: 3.37%
2900 SHIPMASTER Way unit: 211 #211 Annapolis, MD NEW PRICE Welcome to your Annapolis retreat-Unit #211 is a bright and breezy 2-bedroom...	2 beds \| 2 baths \| 1,154 sq.ft.	$344,900	Airbnb cash on cash: 3% Traditional cash on cash: 4.24% Airbnb Rental Income: $2338 Traditional Rental Income: $2162 Airbnb ROI: 3% Traditional ROI: 4.24%
5 PARK Place unit: 428 #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.	$985,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 0.73% Airbnb Rental Income: $2680 Traditional Rental Income: $2797 Airbnb ROI: -0.09% Traditional ROI: 0.73%
2022 SAMS Way unit: 12A #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: 0.22% Traditional cash on cash: 2.26% Airbnb Rental Income: $2338 Traditional Rental Income: $3045 Airbnb ROI: 0.22% Traditional ROI: 2.26%
308 FORBES ST #O Annapolis, MD Coastal Living with a Waterfront Deck Overlooking Weems Creek - Mariners Cove, West Annapo...	1 beds \| 1 baths \| N/A	$407,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 1.3% Airbnb Rental Income: $1744 Traditional Rental Income: $1338 Airbnb ROI: 1.11% Traditional ROI: 1.3%
1915 TOWNE CENTRE Boulevard unit: 301 #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: 0.77% Traditional cash on cash: 2.21% Airbnb Rental Income: $2338 Traditional Rental Income: $2599 Airbnb ROI: 0.77% Traditional ROI: 2.21%
1915 TOWNE CENTRE BLVD #1210 Annapolis, MD FABULOUS PENTHOUSE. Embrace a lifestyle of unparalleled luxury and breathtaking views wit...	3 beds \| 4 baths \| N/A	$1,695,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 0.14% Airbnb Rental Income: $2680 Traditional Rental Income: $3337 Airbnb ROI: -0.68% Traditional ROI: 0.14%
1915 TOWNE CENTRE BLVD #1013 Annapolis, MD The epitome of luxury living resides in Annapolis at Grand View! Reduced for QUICK SALE an...	2 beds \| 2 baths \| N/A	$545,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 2.47% Airbnb Rental Income: $2338 Traditional Rental Income: $2362 Airbnb ROI: 1.28% Traditional ROI: 2.47%
2186 CHESAPEAKE HARBOUR Drive Annapolis, MD Welcome to this extraordinary townhouse offering private water views and easy access to th...	3 beds \| 4 baths \| 2,719 sq.ft.	$1,695,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 0.48% Airbnb Rental Income: $2680 Traditional Rental Income: $3760 Airbnb ROI: -0.61% Traditional ROI: 0.48%
7101 BAY FRONT DR #400 Annapolis, MD MOTIVATED SELLER, JUST REDUCED ANOTHER $10,000!! It's a life of luxury amid the Annapol...	1 beds \| 1 baths \| N/A	$265,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 5.1% Airbnb Rental Income: $1744 Traditional Rental Income: $1966 Airbnb ROI: 2.29% Traditional ROI: 5.1%
1915 TOWNE CENTRE BLVD #502 Annapolis, MD This exceptional 5th-floor condo offers a one-of-a-kind, unique floor plan with breathtaki...	2 beds \| 2 baths \| N/A	$575,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 2.83% Airbnb Rental Income: $2338 Traditional Rental Income: $2654 Airbnb ROI: 1.17% Traditional ROI: 2.83%
287 STATE Street unit: 2 #2 Annapolis, MD South Annapolis Yacht Center is located on Spa Creek overlooking the beautiful skyline of ...	3 beds \| 3 baths \| 2,949 sq.ft.	$5,950,000	Airbnb cash on cash: -1.1% Traditional cash on cash: -0.77% Airbnb Rental Income: $2680 Traditional Rental Income: $3839 Airbnb ROI: -1.1% Traditional ROI: -0.77%
78 OLD MILL BOTTOM Road N unit: 101 #101 Annapolis, MD Priced to sell. Compare vs. buying new. Welcome to The Element at Mill Creek, an exclusive...	2 beds \| 2 baths \| 1,723 sq.ft.	$614,900	Airbnb cash on cash: 0.89% Traditional cash on cash: 2.21% Airbnb Rental Income: $2338 Traditional Rental Income: $2517 Airbnb ROI: 0.89% Traditional ROI: 2.21%
5 PARK Place unit: 507 #507 Annapolis, MD Experience luxury and convenience at The Residence at Park Place!! This two-bedroom, two-b...	2 beds \| 2 baths \| 1,277 sq.ft.	$675,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 1.83% Airbnb Rental Income: $2338 Traditional Rental Income: $2511 Airbnb ROI: 0.63% Traditional ROI: 1.83%
1915 TOWNE CENTRE BLVD #606 Annapolis, MD Time for a Lifestyle Upgrade - Welcome to GrandView at Annapolis Town Center! Step into el...	2 beds \| 3 baths \| N/A	$755,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 1.98% Airbnb Rental Income: $2338 Traditional Rental Income: $2862 Airbnb ROI: 0.41% Traditional ROI: 1.98%
1509 FERAL DAE LN #204 Annapolis, MD Price Reduction! Fantastic price for this gorgeous garage unit !! Enjoy a luxurious lifest...	2 beds \| 2 baths \| N/A	$489,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 3.69% Airbnb Rental Income: $2338 Traditional Rental Income: $2645 Airbnb ROI: 1.75% Traditional ROI: 3.69%
316 BURNSIDE ST #304 Annapolis, MD Beautiful Condo on Spa Creek! PRICE IMPROVEMENT TO $460K. Great investment property, secon...	1 beds \| 1 baths \| N/A	$460,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 1.26% Airbnb Rental Income: $1744 Traditional Rental Income: $1396 Airbnb ROI: 0.95% Traditional ROI: 1.26%
312 SEVERN Avenue unit: W 401 #W 401 Annapolis, MD Location! Location! Location! Perched on the top floor of The Tecumseh-Maryland's first co...	1 beds \| 1 baths \| 660 sq.ft.	$540,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 0.83% Airbnb Rental Income: $1744 Traditional Rental Income: $1537 Airbnb ROI: 0.29% Traditional ROI: 0.83%
21 CHESAPEAKE LNDG Annapolis, MD Spectacular Water View Home nestled at the tip of Eastport Peninsula between Spa Creek, Ba...	4 beds \| 4 baths \| N/A	$1,599,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 0.5% Airbnb Rental Income: $3104 Traditional Rental Income: $3477 Airbnb ROI: -0.23% Traditional ROI: 0.5%
2709 SUMMERVIEW WAY #303 Annapolis, MD Come tour this updated two story sought after 3rd floor penthouse with cathedral ceilings ...	2 beds \| 3 baths \| N/A	$413,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 4.02% Airbnb Rental Income: $2338 Traditional Rental Income: $2440 Airbnb ROI: 2.26% Traditional ROI: 4.02%
2108 CHESAPEAKE HARBOUR Drive E unit: 201 #201 Annapolis, MD Buyer's home contingency fell through. Now is your chance to call this HOME! Welcome to th...	3 beds \| 3 baths \| 1,700 sq.ft.	$645,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 1.86% Airbnb Rental Income: $2680 Traditional Rental Income: $2878 Airbnb ROI: 0.47% Traditional ROI: 1.86%
1507 BROADNECK Place unit: 404 #404 Annapolis, MD Welcome to the exquisite penthouse level sanctuary at 1507 Broadneck Place, Unit 404, Anna...	2 beds \| 2 baths \| 1,235 sq.ft.	$409,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 4.17% Airbnb Rental Income: $2338 Traditional Rental Income: $2392 Airbnb ROI: 2.52% Traditional ROI: 4.17%
5 PARK Place unit: 217 #217 Annapolis, MD The recent price adjustment makes this condo an exceptional value in the heart of historic...	2 beds \| 2 baths \| 1,343 sq.ft.	$699,900	Airbnb cash on cash: 0.53% Traditional cash on cash: 1.74% Airbnb Rental Income: $2338 Traditional Rental Income: $2553 Airbnb ROI: 0.53% Traditional ROI: 1.74%
301 BURNSIDE Street unit: C 202 #C 202 Annapolis, MD REDUCED AND PRICED TO SELL! STEP INTO LUXURY AT THE YACHT CLUB CONDOMINIUMS OVERLOOKING BE...	1 beds \| 1 baths \| 513 sq.ft.	$599,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 0.82% Airbnb Rental Income: $1744 Traditional Rental Income: $1628 Airbnb ROI: 0.17% Traditional ROI: 0.82%
10 SILVERWOOD Circle unit: 10 #10 Annapolis, MD LISTING DESCRIPTION UPDATED 10/3/2025 This top-floor penthouse condo has been extensiv...	2 beds \| 2 baths \| 1,164 sq.ft.	$299,900	Airbnb cash on cash: 3.97% Traditional cash on cash: 5.37% Airbnb Rental Income: $2338 Traditional Rental Income: $2157 Airbnb ROI: 3.97% Traditional ROI: 5.37%
5 PARK PL #626 Annapolis, MD This 2 bedroom, 2 bath condo is move-in ready! Freshly painted, and brand new carpet in be...	2 beds \| 2 baths \| N/A	$699,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 1.3% Airbnb Rental Income: $2338 Traditional Rental Income: $2249 Airbnb ROI: 0.55% Traditional ROI: 1.3%
930 ASTERN Way unit: 511 #511 Annapolis, MD Don't miss this rare opportunity! This spacious 2-bedroom, 2-bathroom condo offers over 1,...	2 beds \| 2 baths \| 1,635 sq.ft.	$404,900	Airbnb cash on cash: 1.91% Traditional cash on cash: 4.16% Airbnb Rental Income: $2338 Traditional Rental Income: $2612 Airbnb ROI: 1.91% Traditional ROI: 4.16%
2155 SCOTTS CROSSING Court unit: 303 #303 Annapolis, MD Sunny and bright top-floor condo featuring an open floor plan and a cozy gas fireplace. En...	2 beds \| 2 baths \| 1,126 sq.ft.	$349,900	Airbnb cash on cash: 3.16% Traditional cash on cash: 5.34% Airbnb Rental Income: $2338 Traditional Rental Income: $2475 Airbnb ROI: 3.16% Traditional ROI: 5.34%
2010 QUAY VILLAGE Court unit: 201 #201 Annapolis, MD Dreaming of a life by the water, with Bay views? Now's your chance to make it a reality in...	2 beds \| 2 baths \| 1,489 sq.ft.	$600,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 1.51% Airbnb Rental Income: $2338 Traditional Rental Income: $2368 Airbnb ROI: 0.42% Traditional ROI: 1.51%
5 PARK Place unit: 224 #224 Annapolis, MD Welcome to the luxury condominium community known as the Residence at Park Place in Annapo...	2 beds \| 2 baths \| 1,188 sq.ft.	$647,000	Airbnb cash on cash: -1.12% Traditional cash on cash: 0.07% Airbnb Rental Income: $2338 Traditional Rental Income: $2476 Airbnb ROI: -1.12% Traditional ROI: 0.07%
803 COXSWAIN Way unit: 203 #203 Annapolis, MD Welcome to Heritage Harbour, Annapolis' premier 55+ community offering resort-style living...	2 beds \| 2 baths \| 1,190 sq.ft.	$379,900	Airbnb cash on cash: 2.31% Traditional cash on cash: 3.94% Airbnb Rental Income: $2338 Traditional Rental Income: $2343 Airbnb ROI: 2.31% Traditional ROI: 3.94%

Your search for investment property begins and ends here

Condos for Sale in Annapolis, MD

1915 TOWNE CENTRE Boulevard unit: 807 #807

Annapolis, MD

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

$545,000

Airbnb cash on cash: 1.22%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $2338

Traditional Rental Income: $2694

Airbnb ROI: 1.22%

Traditional ROI: 3.06%

66 FRANKLIN ST #20

Annapolis, MD

1 beds | 2 baths | N/A

$750,000

Airbnb cash on cash: -0.32%

Traditional cash on cash: 1.09%

Airbnb Rental Income: $1744

Traditional Rental Income: $2248

Airbnb ROI: -0.32%

Traditional ROI: 1.09%

5 PARK Place unit: 107 #107

Annapolis, MD

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

$625,000

Airbnb cash on cash: 0.74%

Traditional cash on cash: 2.1%

Airbnb Rental Income: $2338

Traditional Rental Income: $2551

Airbnb ROI: 0.74%

Traditional ROI: 2.1%

2026 GOV THOMAS BLADEN Way unit: 203 #203

Annapolis, MD

2 beds | 2 baths | 1,006 sq.ft.

$358,000

Airbnb cash on cash: 3.2%

Traditional cash on cash: 4.18%

Airbnb Rental Income: $2338

Traditional Rental Income: $2089

Airbnb ROI: 3.2%

Traditional ROI: 4.18%

66 FRANKLIN Street unit: 509 #509

Annapolis, MD

3 beds | 4 baths | 2,477 sq.ft.

$1,850,000

Airbnb cash on cash: -0.73%

Traditional cash on cash: 0.05%

Airbnb Rental Income: $2680

Traditional Rental Income: $3393

Airbnb ROI: -0.73%

Traditional ROI: 0.05%

1915 TOWNE CENTRE BLVD #1004

Annapolis, MD

2 beds | 2 baths | N/A

$975,000

Airbnb cash on cash: -0.01%

Traditional cash on cash: 1.07%

Airbnb Rental Income: $2338

Traditional Rental Income: $2737

Airbnb ROI: -0.01%

Traditional ROI: 1.07%

633 BAYSTONE CT

Annapolis, MD

3 beds | 2 baths | N/A

$450,000

Airbnb cash on cash: 2.71%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $2680

Traditional Rental Income: $2717

Airbnb ROI: 2.71%

Traditional ROI: 4.31%

930 ASTERN Way unit: 609 #609

Annapolis, MD

2 beds | 3 baths | 1,926 sq.ft.

$425,000

Airbnb cash on cash: 1.63%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $2338

Traditional Rental Income: $2912

Airbnb ROI: 1.63%