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.

Single Family Homes for Sale in Annapolis, MD

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

Showing 184 Single Family Residential 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
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%
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.	$975,000	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.	$589,000	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%
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.	$750,000	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%
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.	$850,000	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.	$5,898,000	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.	$615,000	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%
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%
1226 Tyler Ave Annapolis, MD Prepare to fall in love with this totally renovated gem! A complete and tasteful remodel h...	3 beds \| 1 baths \| 1,056 sq.ft.	$399,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 3.19% Airbnb Rental Income: $2603 Traditional Rental Income: $1929 Airbnb ROI: 3.33% Traditional ROI: 3.19%
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%
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%
1045 Skyview Dr Annapolis, MD Nestled in the charming community of Cape St. Claire, this delightful raised ranch home of...	4 beds \| 2 baths \| 2,327 sq.ft.	$579,500	Airbnb cash on cash: 1.71% Traditional cash on cash: 3.42% Airbnb Rental Income: $2683 Traditional Rental Income: $2972 Airbnb ROI: 1.71% Traditional ROI: 3.42%
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.	$850,000	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%
935 Marine Dr Annapolis, MD This delightful colonial combines a traditional floor plan with modern features / Light an...	4 beds \| 2 baths \| 2,480 sq.ft.	$625,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 3.06% Airbnb Rental Income: $2683 Traditional Rental Income: $2902 Airbnb ROI: 1.6% Traditional ROI: 3.06%
1724 Robinhood Rd Annapolis, MD Beautifully updated and thoughtfully designed, this four-bedroom home offers exceptional i...	4 beds \| 3 baths \| 3,080 sq.ft.	$959,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 2.02% Airbnb Rental Income: $2683 Traditional Rental Income: $3588 Airbnb ROI: 0.29% Traditional ROI: 2.02%
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.	$540,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 3.65% Airbnb Rental Income: $2512 Traditional Rental Income: $2932 Airbnb ROI: 1.61% Traditional ROI: 3.65%
152 Jefferson St Annapolis, MD BEAUTIFULLY RENOVATED EASTPORT GEM with MODERN COASTAL FINISHES! Perfect for a Primary Res...	4 beds \| 3 baths \| 2,282 sq.ft.	$785,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 3.68% Airbnb Rental Income: $2683 Traditional Rental Income: $3862 Airbnb ROI: 1.2% Traditional ROI: 3.68%
211 N Pindell Ave Annapolis, MD Tucked just off Poplar Trail, 211 Pindell Avenue is a classic brick rancher that lives far...	3 beds \| 2 baths \| 4,497 sq.ft.	$745,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 0.91% Airbnb Rental Income: $2603 Traditional Rental Income: $2185 Airbnb ROI: 0.61% Traditional ROI: 0.91%
1252 Creek Dr Annapolis, MD Charming Oyster Harbor Home on an oversized fully fenced lot just minutes from downtown An...	3 beds \| 2 baths \| 1,555 sq.ft.	$565,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 2.74% Airbnb Rental Income: $2603 Traditional Rental Income: $2449 Airbnb ROI: 1.85% Traditional ROI: 2.74%
310 Epping Way Annapolis, MD Welcome to this extraordinary "find" in Epping Forest. One-of-a-kind craftsman bungalow wi...	3 beds \| 2 baths \| 2,036 sq.ft.	$1,100,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 0.98% Airbnb Rental Income: $2603 Traditional Rental Income: $2719 Airbnb ROI: 0.26% Traditional ROI: 0.98%
76 Summerfield Dr Annapolis, MD This Cape Cod located minutes from downtown Annapolis will charm you the minute you arrive...	3 beds \| 2 baths \| 1,203 sq.ft.	$499,999	Airbnb cash on cash: 2.33% Traditional cash on cash: 3.41% Airbnb Rental Income: $2603 Traditional Rental Income: $2485 Airbnb ROI: 2.33% Traditional ROI: 3.41%
45 Fleet St Annapolis, MD Remarkable updated 1700's Tidewater Georgian Vernacular home with off street parking and ...	2 beds \| 1 baths \| 864 sq.ft.	$824,995	Airbnb cash on cash: -0.27% Traditional cash on cash: 0.52% Airbnb Rental Income: $1822 Traditional Rental Income: $1938 Airbnb ROI: -0.27% Traditional ROI: 0.52%
32 Cornhill St Annapolis, MD Great historic home built in 1850 in the heart of downtown historic Annapolis. Completely ...	2 beds \| 1 baths \| 1,064 sq.ft.	$774,900	Airbnb cash on cash: -0.38% Traditional cash on cash: 1.63% Airbnb Rental Income: $1822 Traditional Rental Income: $2776 Airbnb ROI: -0.38% Traditional ROI: 1.63%
1917 Cherry Rd Annapolis, MD Welcome to Pleasant Plains, one of Annapolis' most sought-after communities, where generou...	4 beds \| 2 baths \| 2,368 sq.ft.	$675,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 3.69% Airbnb Rental Income: $2683 Traditional Rental Income: $3588 Airbnb ROI: 1.25% Traditional ROI: 3.69%
2 Silopanna Ct Annapolis, MD Annapolis single family home, Completely updated and move-in ready! This home offers a fen...	4 beds \| 2 baths \| 2,000 sq.ft.	$549,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 2.51% Airbnb Rental Income: $2683 Traditional Rental Income: $2501 Airbnb ROI: 1.7% Traditional ROI: 2.51%
4 Shiley St Annapolis, MD Here's the West Annapolis unicorn property that you've been waiting for! A VERY RARE TRIPL...	5 beds \| 5 baths \| 5,312 sq.ft.	$3,090,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 0.13% Airbnb Rental Income: $2512 Traditional Rental Income: $4522 Airbnb ROI: -0.79% Traditional ROI: 0.13%
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.	$899,899	Airbnb cash on cash: 0.56% Traditional cash on cash: 0.61% Airbnb Rental Income: $2603 Traditional Rental Income: $2023 Airbnb ROI: 0.56% Traditional ROI: 0.61%
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.	$569,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 4.04% Airbnb Rental Income: $2683 Traditional Rental Income: $3378 Airbnb ROI: 1.54% Traditional ROI: 4.04%
400 Jefferson St Annapolis, MD Nestled in the heart of historic Eastport Annapolis, this coastal craftsman has been exten...	4 beds \| 4 baths \| 4,200 sq.ft.	$1,950,000	Airbnb cash on cash: -1.03% Traditional cash on cash: -0.29% Airbnb Rental Income: $2683 Traditional Rental Income: $3405 Airbnb ROI: -1.03% Traditional ROI: -0.29%
83 Market St Annapolis, MD This exceptional Historic District home combines the charm of a classic Annapolis address ...	5 beds \| 4 baths \| 3,178 sq.ft.	$2,295,000	Airbnb cash on cash: -0.98% Traditional cash on cash: -0.15% Airbnb Rental Income: $2512 Traditional Rental Income: $3660 Airbnb ROI: -0.98% Traditional ROI: -0.15%
238 King George St Annapolis, MD Perfectly positioned on one of the most coveted streets in Historic Annapolis, just steps ...	4 beds \| 3 baths \| 3,750 sq.ft.	$2,950,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 0.31% Airbnb Rental Income: $2683 Traditional Rental Income: $5340 Airbnb ROI: -0.9% Traditional ROI: 0.31%

Your search for investment property begins and ends here

Single Family Homes 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%

2978 Valley View Rd

Annapolis, MD

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

$975,000

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.

$589,000

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%

11 S Acton Pl

Annapolis, MD

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

3 beds | 2 baths | 1,742 sq.ft.

$750,000

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%

349 EPPING WAY

Annapolis, MD

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

4 beds | 3 baths | 2,533 sq.ft.

$850,000

Airbnb cash on cash: 0.59%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $2683

Traditional Rental Income: $3524

Airbnb ROI: 0.59%