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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
5 PARK PLACE #514 Annapolis, MD Move right in and enjoy the fabulous downtown Annapolis lifestyle in this meticulously mai...	2 beds \| 2 baths \| 1,056 sq.ft.	$660,000	Airbnb cash on cash: 1.51% Traditional cash on cash: 1.95% Airbnb Rental Income: $2829 Traditional Rental Income: $2437 Airbnb ROI: 1.51% Traditional ROI: 1.95%
2900 SHIPMASTER WAY #315 Annapolis, MD Don't miss outâtake advantage of this fantastic opportunity as a buyer! Discover your dr...	2 beds \| 2 baths \| 1,008 sq.ft.	$299,900	Airbnb cash on cash: 5.13% Traditional cash on cash: 5.22% Airbnb Rental Income: $2829 Traditional Rental Income: $2194 Airbnb ROI: 5.13% Traditional ROI: 5.22%
2006 PEGGY STEWART WAY #101 Annapolis, MD Discover this 2 bedroom, 2 bath ground-level unit in highly sought after Tidewater Colony....	2 beds \| 2 baths \| 1,123 sq.ft.	$340,000	Airbnb cash on cash: 4.6% Traditional cash on cash: 5.06% Airbnb Rental Income: $2829 Traditional Rental Income: $2313 Airbnb ROI: 4.6% Traditional ROI: 5.06%
1004 PRIMROSE RD #301 Annapolis, MD This beautiful condo has it all. Open floor plan with a balcony overlooking woods. This se...	1 beds \| 1 baths \| N/A	$254,990	Airbnb cash on cash: 8.52% Traditional cash on cash: 3.55% Airbnb Rental Income: $3393 Traditional Rental Income: $1441 Airbnb ROI: 8.52% Traditional ROI: 3.55%
7016 CLINTON COURT #22A Annapolis, MD This home is located in the gated waterfront condo community of Chesapeake Harbor where re...	2 beds \| 3 baths \| 1,830 sq.ft.	$649,900	Airbnb cash on cash: 1.12% Traditional cash on cash: 1.84% Airbnb Rental Income: $2829 Traditional Rental Income: $2602 Airbnb ROI: 1.12% Traditional ROI: 1.84%
940 ASTERN WAY #405 Annapolis, MD Beautifully Staged condominium The Reserve at Heritage Harbour. One of the largest units w...	2 beds \| 2 baths \| N/A	$535,000	Airbnb cash on cash: 2.22% Traditional cash on cash: 2.25% Airbnb Rental Income: $2829 Traditional Rental Income: $2185 Airbnb ROI: 2.22% Traditional ROI: 2.25%
7038 CLINTON CT #11B Annapolis, MD Welcome to an amazing condo experience right here in Chesapeake Harbour in Annapolis, MD. ...	3 beds \| 3 baths \| N/A	$850,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 1.26% Airbnb Rental Income: $4318 Traditional Rental Income: $2669 Airbnb ROI: 2.2% Traditional ROI: 1.26%
5 PARK PL #428 Annapolis, MD Discover the perfect blend of comfort and convenience in this rare 3-bedroom, 2.5-bath con...	3 beds \| 3 baths \| N/A	$1,450,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 0.18% Airbnb Rental Income: $4318 Traditional Rental Income: $2797 Airbnb ROI: 0.64% Traditional ROI: 0.18%
930 ASTERN WAY #207 Annapolis, MD Gorgeous corner unit on the back of the building provides privacy and peaceful views of th...	2 beds \| 2 baths \| 1,464 sq.ft.	$379,900	Airbnb cash on cash: 3.51% Traditional cash on cash: 3.64% Airbnb Rental Income: $2829 Traditional Rental Income: $2216 Airbnb ROI: 3.51% Traditional ROI: 3.64%
940 ASTERN WAY #504 Annapolis, MD Charming 2 bedroom, 2 bath condo for sale in the heart of Heritage Harbour's 55+ retiremen...	2 beds \| 2 baths \| 1,272 sq.ft.	$385,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 4.34% Airbnb Rental Income: $2829 Traditional Rental Income: $2532 Airbnb ROI: 3.33% Traditional ROI: 4.34%
2100 CHESAPEAKE HARBOUR DRIVE #T2 Annapolis, MD Welcome to resort style living at Chesapeake Harbour! This spectacular 2 bedroom condo ha...	2 beds \| 2 baths \| 1,319 sq.ft.	$565,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 2.13% Airbnb Rental Income: $2829 Traditional Rental Income: $2608 Airbnb ROI: 1.3% Traditional ROI: 2.13%
1915 TOWNE CENTRE BLVD #1210 Annapolis, MD Embrace a lifestyle of unparalleled luxury and breathtaking views with this rare opportuni...	3 beds \| 4 baths \| N/A	$1,875,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 0.03% Airbnb Rental Income: $4318 Traditional Rental Income: $3337 Airbnb ROI: 0.08% Traditional ROI: 0.03%
1915 TOWNE CENTRE BLVD #1013 Annapolis, MD Introducing the epitome of luxury living in Annapolis! Experience the pinnacle of sophisti...	2 beds \| 2 baths \| N/A	$629,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 2.01% Airbnb Rental Income: $2829 Traditional Rental Income: $2362 Airbnb ROI: 1.68% Traditional ROI: 2.01%
2052 QUAKER WAY #14 Annapolis, MD IMPRESSIVE 2 BR, 2 FBA LOFT CONDO (2 LEVELS) w/BALCONY FACING TREES! Welcome Home IN th...	2 beds \| 2 baths \| N/A	$346,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 5.19% Airbnb Rental Income: $2829 Traditional Rental Income: $2390 Airbnb ROI: 4.51% Traditional ROI: 5.19%
2002 QUAY VILLAGE COURT #202 Annapolis, MD Step into luxury with this stunning move-in-ready condo, designed for modern living in a s...	2 beds \| 2 baths \| 1,524 sq.ft.	$429,000	Airbnb cash on cash: 2.32% Traditional cash on cash: 2.85% Airbnb Rental Income: $2829 Traditional Rental Income: $2381 Airbnb ROI: 2.32% Traditional ROI: 2.85%
2574 RIVA ROAD #1A Annapolis, MD Discover tranquil living in this rarely available, beautifully updated 3-bedroom, 2-bath c...	3 beds \| 2 baths \| 1,147 sq.ft.	$349,900	Airbnb cash on cash: 7% Traditional cash on cash: 3.88% Airbnb Rental Income: $4318 Traditional Rental Income: $2382 Airbnb ROI: 7% Traditional ROI: 3.88%
5 PRESIDENT POINT DRIVE #A1 Annapolis, MD Spend the Holidays in Annapolis!! First floor 1 Bedroom, 1 Bath condo is a perfect "home ...	1 beds \| 1 baths \| 923 sq.ft.	$670,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 0.73% Airbnb Rental Income: $3393 Traditional Rental Income: $1861 Airbnb ROI: 1.97% Traditional ROI: 0.73%
1125 LAKE HERON DRIVE #1B Annapolis, MD Lake Heron Condo in great condition on the main level, in a conveniently located building....	2 beds \| 2 baths \| 1,089 sq.ft.	$359,000	Airbnb cash on cash: 4.06% Traditional cash on cash: 4.58% Airbnb Rental Income: $2829 Traditional Rental Income: $2346 Airbnb ROI: 4.06% Traditional ROI: 4.58%
1915 TOWNE CENTRE BOULEVARD #1005 Annapolis, MD PRICE REDUCED AND OPEN HOUSE, SUNDAY , OCT 20th From12:00PM - 2:00PM. Please join us! Beau...	2 beds \| 2 baths \| 1,682 sq.ft.	$785,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 1.44% Airbnb Rental Income: $2829 Traditional Rental Income: $2551 Airbnb ROI: 0.92% Traditional ROI: 1.44%
1507 BROADNECK PL #403 Annapolis, MD Stunning 2 BR/2 FBA Loft Condo w/ vaulted ceilings in Sought after 55+ Four Seasons at St ...	2 beds \| 2 baths \| N/A	$423,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 3.61% Airbnb Rental Income: $2829 Traditional Rental Income: $2239 Airbnb ROI: 3.43% Traditional ROI: 3.61%
2510 NORTH HAVEN COVE #104 Annapolis, MD Stunningly Renovated 2-Bedroom Home in Heritage Harbour Step into this beautifully renova...	2 beds \| 2 baths \| 1,461 sq.ft.	$529,900	Airbnb cash on cash: 2.11% Traditional cash on cash: 2.45% Airbnb Rental Income: $2829 Traditional Rental Income: $2337 Airbnb ROI: 2.11% Traditional ROI: 2.45%
7042 CLINTON CT Annapolis, MD Feel your stress melt away the moment you pass through the gates of Chesapeake Harbour, an...	3 beds \| 3 baths \| N/A	$850,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 1.33% Airbnb Rental Income: $4318 Traditional Rental Income: $2727 Airbnb ROI: 2.2% Traditional ROI: 1.33%
409 MAHAN LN Annapolis, MD Welcome to this stunning home in the heart of Annapolis, offering convenience and comfort ...	3 beds \| 3 baths \| N/A	$575,000	Airbnb cash on cash: 4.18% Traditional cash on cash: 3.1% Airbnb Rental Income: $4318 Traditional Rental Income: $2827 Airbnb ROI: 4.18% Traditional ROI: 3.1%
930 ASTERN WAY #302 Annapolis, MD Spacious Condo - freshly painted and ready to move in. Upgrades include new HVAC (2022), ...	2 beds \| 2 baths \| 1,477 sq.ft.	$377,700	Airbnb cash on cash: 3.28% Traditional cash on cash: 3.45% Airbnb Rental Income: $2829 Traditional Rental Income: $2229 Airbnb ROI: 3.28% Traditional ROI: 3.45%
2157 SCOTTS CROSSING COURT #203 Annapolis, MD Price adjusted- be in a new home for the holidays! Buyer Agents warmly welcomed. Location...	2 beds \| 2 baths \| 1,142 sq.ft.	$349,900	Airbnb cash on cash: 4.39% Traditional cash on cash: 5.15% Airbnb Rental Income: $2829 Traditional Rental Income: $2417 Airbnb ROI: 4.39% Traditional ROI: 5.15%
930 ASTERN WAY #106 Annapolis, MD Rare desirable first floor unit with direct access from exterior! Fall in love with this ...	1 beds \| 2 baths \| 1,235 sq.ft.	$299,900	Airbnb cash on cash: 6.46% Traditional cash on cash: 5.26% Airbnb Rental Income: $3393 Traditional Rental Income: $2300 Airbnb ROI: 6.46% Traditional ROI: 5.26%
2123 BEACH VILLAGE CT #102 Annapolis, MD Welcome to your dream retreat! This stunning waterfront condo in the highly sought-after C...	2 beds \| 2 baths \| N/A	$685,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 1.13% Airbnb Rental Income: $2829 Traditional Rental Income: $2043 Airbnb ROI: 1.33% Traditional ROI: 1.13%
15 PRESIDENT POINT DRIVE #A2 Annapolis, MD Stunning Waterfront Retreat in President Point â Your Dream Home Awaits! Discover the p...	1 beds \| 1 baths \| 923 sq.ft.	$665,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 0.64% Airbnb Rental Income: $3393 Traditional Rental Income: $1800 Airbnb ROI: 1.99% Traditional ROI: 0.64%
801 DREAMS LANDING WAY #801 Annapolis, MD Welcome to Dreams Landing. This hidden gem overlooks The Severn River. It is the ideal pl...	2 beds \| 1 baths \| 981 sq.ft.	$425,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.59% Airbnb Rental Income: $2829 Traditional Rental Income: $1899 Airbnb ROI: 3.27% Traditional ROI: 2.59%
7101 BAY FRONT DR #400 Annapolis, MD Isn't this how you always envisioned retirement!! A premiere life of luxury overlooking th...	1 beds \| 1 baths \| N/A	$285,000	Airbnb cash on cash: 7.19% Traditional cash on cash: 4.68% Airbnb Rental Income: $3393 Traditional Rental Income: $1966 Airbnb ROI: 7.19% Traditional ROI: 4.68%
940 ASTERN WAY #108 Annapolis, MD Gorgeous Main Level Unit! Oak hardwood flooring throughout! 3 bedroom, 3 full baths. Lovel...	3 beds \| 3 baths \| N/A	$600,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 2.56% Airbnb Rental Income: $4318 Traditional Rental Income: $2662 Airbnb ROI: 3.9% Traditional ROI: 2.56%
7036 HARBOUR VILLAGE COURT #T1 Annapolis, MD 7036 Harbour Village Court in Annapolis, MD, is a charming waterfront townhouse that combi...	1 beds \| 1 baths \| N/A	$380,000	Airbnb cash on cash: 3.44% Traditional cash on cash: 0.25% Airbnb Rental Income: $3393 Traditional Rental Income: $1502 Airbnb ROI: 3.44% Traditional ROI: 0.25%
1240 GEMINI DRIVE #95 Annapolis, MD Welcome to your dream home! Nestled in the heart of Annapolis, this Move-In-Ready home of...	3 beds \| 3 baths \| 1,956 sq.ft.	$365,000	Airbnb cash on cash: 7.72% Traditional cash on cash: 6.35% Airbnb Rental Income: $4318 Traditional Rental Income: $2943 Airbnb ROI: 7.72% Traditional ROI: 6.35%
2106 CHESAPEAKE HARBOUR DR #T1 Annapolis, MD Welcome to Waterfront Living at Chesapeake Harbour in Annapolis, MD! Discover this beautif...	2 beds \| 2 baths \| N/A	$549,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 2.23% Airbnb Rental Income: $2829 Traditional Rental Income: $2204 Airbnb ROI: 2.16% Traditional ROI: 2.23%
3 HERITAGE COURT #C Annapolis, MD OFFER DEADLINE - SUN 11/24 @ 5pm. As requested by the seller, the deadline for submitting...	2 beds \| 1 baths \| 960 sq.ft.	$225,000	Airbnb cash on cash: 7.79% Traditional cash on cash: 6.28% Airbnb Rental Income: $2829 Traditional Rental Income: $1847 Airbnb ROI: 7.79% Traditional ROI: 6.28%
2900 SHIPMASTER WAY #316 Annapolis, MD Welcome to your new home in the highly sought after Heritage Harbour community! Rarely av...	2 beds \| 2 baths \| 1,044 sq.ft.	$298,000	Airbnb cash on cash: 5.08% Traditional cash on cash: 5.06% Airbnb Rental Income: $2829 Traditional Rental Income: $2164 Airbnb ROI: 5.08% Traditional ROI: 5.06%
1915 TOWNE CENTRE BOULEVARD #1214 Annapolis, MD Welcome to GrandView, one of the most sought-after and luxurious locations in Annapolis! T...	3 beds \| 3 baths \| 2,602 sq.ft.	$1,299,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 0.69% Airbnb Rental Income: $4318 Traditional Rental Income: $3259 Airbnb ROI: 0.82% Traditional ROI: 0.69%
30 SANDSTONE COURT #G Annapolis, MD Discover the perfect blend of comfort and convenience at 30 Sandstone Court, Unit G, in th...	2 beds \| 2 baths \| 1,010 sq.ft.	$270,000	Airbnb cash on cash: 6.15% Traditional cash on cash: 6.16% Airbnb Rental Income: $2829 Traditional Rental Income: $2172 Airbnb ROI: 6.15% Traditional ROI: 6.16%
13-C HERITAGE CT Annapolis, MD A rare opportunity to own a beautifully updated 2 bedroom condo in the heart of Annapolis ...	2 beds \| 1 baths \| 960 sq.ft.	$235,000	Airbnb cash on cash: 7.37% Traditional cash on cash: 5.29% Airbnb Rental Income: $2829 Traditional Rental Income: $1705 Airbnb ROI: 7.37% Traditional ROI: 5.29%

Your search for investment property begins and ends here

Condos for Sale in Annapolis, MD

5 PARK PLACE #514

Annapolis, MD

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

$660,000

Airbnb cash on cash: 1.51%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $2829

Traditional Rental Income: $2437

Airbnb ROI: 1.51%

Traditional ROI: 1.95%

2900 SHIPMASTER WAY #315

Annapolis, MD

2 beds | 2 baths | 1,008 sq.ft.

$299,900

Airbnb cash on cash: 5.13%

Traditional cash on cash: 5.22%

Airbnb Rental Income: $2829

Traditional Rental Income: $2194

Airbnb ROI: 5.13%

Traditional ROI: 5.22%

2006 PEGGY STEWART WAY #101

Annapolis, MD

2 beds | 2 baths | 1,123 sq.ft.

$340,000

Airbnb cash on cash: 4.6%

Traditional cash on cash: 5.06%

Airbnb Rental Income: $2829

Traditional Rental Income: $2313

Airbnb ROI: 4.6%

Traditional ROI: 5.06%

1004 PRIMROSE RD #301

Annapolis, MD

1 beds | 1 baths | N/A

$254,990

Airbnb cash on cash: 8.52%

Traditional cash on cash: 3.55%

Airbnb Rental Income: $3393

Traditional Rental Income: $1441

Airbnb ROI: 8.52%

Traditional ROI: 3.55%

7016 CLINTON COURT #22A

Annapolis, MD

2 beds | 3 baths | 1,830 sq.ft.

$649,900

Airbnb cash on cash: 1.12%

Traditional cash on cash: 1.84%

Airbnb Rental Income: $2829

Traditional Rental Income: $2602

Airbnb ROI: 1.12%

Traditional ROI: 1.84%

940 ASTERN WAY #405

Annapolis, MD

2 beds | 2 baths | N/A

$535,000

Airbnb cash on cash: 2.22%

Traditional cash on cash: 2.25%

Airbnb Rental Income: $2829

Traditional Rental Income: $2185

Airbnb ROI: 2.22%

Traditional ROI: 2.25%

7038 CLINTON CT #11B

Annapolis, MD

3 beds | 3 baths | N/A

$850,000

Airbnb cash on cash: 2.2%

Traditional cash on cash: 1.26%

Airbnb Rental Income: $4318

Traditional Rental Income: $2669

Airbnb ROI: 2.2%

Traditional ROI: 1.26%

5 PARK PL #428

Annapolis, MD

3 beds | 3 baths | N/A

$1,450,000

Airbnb cash on cash: 0.64%

Traditional cash on cash: 0.18%

Airbnb Rental Income: $4318

Traditional Rental Income: $2797

Airbnb ROI: 0.64%