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 94 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
309 MCDONOUGH ROAD Annapolis, MD Admiral Heights Beauty! 309 McDonough Rd features modern upgrades in a layout design for e...	4 beds \| 3 baths \| 2,945 sq.ft.	$890,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.53% Airbnb Rental Income: $null Traditional Rental Income: $3718 Airbnb ROI: N/A Traditional ROI: 2.53%
1230 CRUMMELL AVENUE Annapolis, MD Discover a rare gem in Bay Highlands, the only Annapolis community with its own private, p...	4 beds \| 3 baths \| 2,555 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.16% Airbnb Rental Income: $null Traditional Rental Income: $3443 Airbnb ROI: N/A Traditional ROI: 1.16%
111 CLAY STREET Annapolis, MD Major Price Adjustment!! Great opportunity in West Annapolis! Discover the charm of 111 Cl...	3 beds \| 2 baths \| 1,568 sq.ft.	$599,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.9% Airbnb Rental Income: $null Traditional Rental Income: $2678 Airbnb ROI: N/A Traditional ROI: 2.9%
210 BOWEN COURT Annapolis, MD Welcome to an exquisite single-family residencea turnkey, move-in ready home just minutes ...	5 beds \| 4 baths \| 4,204 sq.ft.	$1,025,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.42% Airbnb Rental Income: $null Traditional Rental Income: $4074 Airbnb ROI: N/A Traditional ROI: 2.42%
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: N/A Traditional cash on cash: 2.08% Airbnb Rental Income: $null Traditional Rental Income: $3336 Airbnb ROI: N/A Traditional ROI: 2.08%
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.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.22% Airbnb Rental Income: $null Traditional Rental Income: $3363 Airbnb ROI: N/A Traditional ROI: 3.22%
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	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.65% Airbnb Rental Income: $null Traditional Rental Income: $3397 Airbnb ROI: N/A Traditional ROI: 2.65%
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: N/A Traditional cash on cash: 3.73% Airbnb Rental Income: $null Traditional Rental Income: $2896 Airbnb ROI: N/A Traditional ROI: 3.73%
1755 ROBINHOOD ROAD Annapolis, MD From the moment you arrive, this 3-bedroom, 2.5-bathroom home welcomes you with charm and ...	3 beds \| 3 baths \| 1,664 sq.ft.	$824,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.8% Airbnb Rental Income: $null Traditional Rental Income: $2805 Airbnb ROI: N/A Traditional ROI: 1.8%
336 SEVERN ROAD Annapolis, MD Waterfront Living in Epping Forest with Stunning Views! Nestled in the exclusive, gated c...	2 beds \| 3 baths \| 1,708 sq.ft.	$829,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.74% Airbnb Rental Income: $null Traditional Rental Income: $3144 Airbnb ROI: N/A Traditional ROI: 1.74%
792 PARKWOOD AVE Annapolis, MD PRICE ADJUSTED! Seller has a 4.5% assumable VA loan for a qualified buyer. 792 Parkwood A...	4 beds \| 5 baths \| N/A	$895,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.57% Airbnb Rental Income: $null Traditional Rental Income: $4925 Airbnb ROI: N/A Traditional ROI: 3.57%
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: N/A Traditional cash on cash: 0.81% Airbnb Rental Income: $null Traditional Rental Income: $3405 Airbnb ROI: N/A Traditional ROI: 0.81%
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.	$580,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.15% Airbnb Rental Income: $null Traditional Rental Income: $3966 Airbnb ROI: N/A Traditional ROI: 5.15%
919 BERWICK DRIVE Annapolis, MD Welcome to this exquisite home nestled conveniently close to downtown Annapolis and Eastpo...	4 beds \| 3 baths \| 2,292 sq.ft.	$799,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.1% Airbnb Rental Income: $null Traditional Rental Income: $3829 Airbnb ROI: N/A Traditional ROI: 3.1%
106 STILLY WAY Annapolis, MD This stunning home, available for delivery in April, boasts high-end upgrades throughout. ...	4 beds \| 5 baths \| 4,594 sq.ft.	$999,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.67% Airbnb Rental Income: $null Traditional Rental Income: $4686 Airbnb ROI: N/A Traditional ROI: 3.67%
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: N/A Traditional cash on cash: 3% Airbnb Rental Income: $null Traditional Rental Income: $4276 Airbnb ROI: N/A Traditional ROI: 3%
40 OAK COURT Annapolis, MD Introducing a distinctive opportunity for visionary entrepreneurs and investors: a commerc...	2 beds \| 2 baths \| 1,061 sq.ft.	$389,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.61% Airbnb Rental Income: $null Traditional Rental Income: $2442 Airbnb ROI: N/A Traditional ROI: 4.61%
1831 DREW ST Annapolis, MD Tucked away with a long, freshly paved driveway and generous outdoor space, 1831 Drew Stre...	5 beds \| 2 baths \| N/A	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.05% Airbnb Rental Income: $null Traditional Rental Income: $2626 Airbnb ROI: N/A Traditional ROI: 3.05%
201 NOTTINGHAM HL Annapolis, MD PRICE REDUCTION - Exciting Opportunity in Sherwood Forest - Enjoy breathtaking panoramic w...	5 beds \| 3 baths \| N/A	$1,980,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.02% Airbnb Rental Income: $null Traditional Rental Income: $3827 Airbnb ROI: N/A Traditional ROI: 0.02%
1632 WINCHESTER RD Annapolis, MD Please note - this tax record is associated with only 3.3 acres, but this listing is for t...	1 beds \| 1 baths \| N/A	$1,900,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.03% Airbnb Rental Income: $null Traditional Rental Income: $1412 Airbnb ROI: N/A Traditional ROI: -1.03%
9 RUSTY RED DR Annapolis, MD Move-in ready new construction from acclaimed local builder, Sturbridge Homes. This specta...	5 beds \| 5 baths \| 5,124 sq.ft.	$1,375,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.67% Airbnb Rental Income: $null Traditional Rental Income: $5042 Airbnb ROI: N/A Traditional ROI: 1.67%
1352 BLACKWALNUT COURT Annapolis, MD this charming four-bedroom, four-bath colonial in the desirable Blackwalnut Cove community...	4 beds \| 4 baths \| 1,696 sq.ft.	$749,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.72% Airbnb Rental Income: $null Traditional Rental Income: $3245 Airbnb ROI: N/A Traditional ROI: 2.72%
179 GREEN ST Annapolis, MD Experience the Essence of Annapolis Charm at 179 Green Street Nestled in the heart of his...	2 beds \| 2 baths \| N/A	$1,175,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.18% Airbnb Rental Income: $null Traditional Rental Income: $1916 Airbnb ROI: N/A Traditional ROI: -0.18%
1971 DOMINOE ROAD Annapolis, MD Welcome to this Wonderful home very close to Annapolis & the properties to be in a private...	4 beds \| 3 baths \| 2,160 sq.ft.	$509,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.65% Airbnb Rental Income: $null Traditional Rental Income: $3187 Airbnb ROI: N/A Traditional ROI: 4.65%
2706 JUDSON PL Annapolis, MD Welcome to 2706 Judson Place, an immaculate completely remodeled rancher nestled in the de...	4 beds \| 3 baths \| N/A	$569,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.23% Airbnb Rental Income: $null Traditional Rental Income: $3325 Airbnb ROI: N/A Traditional ROI: 4.23%
3 PARK LN Annapolis, MD Don't miss this incredible opportunity to own a charming 5 bedroom (3 in main house, 2 in ...	5 beds \| 4 baths \| N/A	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.75% Airbnb Rental Income: $null Traditional Rental Income: $4217 Airbnb ROI: N/A Traditional ROI: 3.75%
1165 GREEN HOLLY COURT Annapolis, MD Cape St. Claire Home sold with Extra Lot and Detached Garage Plans! Plans in Documents. T...	3 beds \| 2 baths \| 2,218 sq.ft.	$585,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.37% Airbnb Rental Income: $null Traditional Rental Income: $2901 Airbnb ROI: N/A Traditional ROI: 3.37%
1534 CIRCLE DR Annapolis, MD Stunning contemporary in Winchester on the Severn featuring abundant windows that provide ...	4 beds \| 3 baths \| N/A	$975,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.16% Airbnb Rental Income: $null Traditional Rental Income: $3528 Airbnb ROI: N/A Traditional ROI: 2.16%
1141 MAINSAIL DRIVE Annapolis, MD Welcome to 1141 Mainsail Drive, a beautifully updated colonial nestled on a desirable corn...	4 beds \| 3 baths \| 2,176 sq.ft.	$949,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.95% Airbnb Rental Income: $null Traditional Rental Income: $3431 Airbnb ROI: N/A Traditional ROI: 1.95%
1632A WINCHESTER ROAD Annapolis, MD Don't miss this incredible opportunity to build your dream luxury estate home on this amaz...	5 beds \| 5 baths \| 5,000 sq.ft.	$4,950,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.07% Airbnb Rental Income: $null Traditional Rental Income: $5746 Airbnb ROI: N/A Traditional ROI: -0.07%
130 GREAT LAKE DRIVE Annapolis, MD Lovely Brick home in private Water Community of Hillsmere Estates that offers 5 Bedroom, 2...	5 beds \| 3 baths \| 2,014 sq.ft.	$647,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.7% Airbnb Rental Income: $null Traditional Rental Income: $3472 Airbnb ROI: N/A Traditional ROI: 3.7%
1924 HIDDEN POINT RD Annapolis, MD Nestled at the end of a quiet cul-de-sac and set on over half an acre, this rare waterfron...	4 beds \| 3 baths \| N/A	$1,875,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.07% Airbnb Rental Income: $null Traditional Rental Income: $3168 Airbnb ROI: N/A Traditional ROI: -0.07%
48A E LAKE DRIVE Annapolis, MD Once-in-a-Lifetime Opportunity to Build Your Dream Waterfront Home in Bay Ridge. Don't mis...	4 beds \| 4 baths \| 3,750 sq.ft.	$3,395,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.28% Airbnb Rental Income: $null Traditional Rental Income: $5689 Airbnb ROI: N/A Traditional ROI: 0.28%
541 SECOND STREET Annapolis, MD A Rare Find in the Heart of Eastport! Built in 2006 with timeless Eastport charm, this bea...	4 beds \| 3 baths \| 2,341 sq.ft.	$1,499,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.3% Airbnb Rental Income: $null Traditional Rental Income: $3120 Airbnb ROI: N/A Traditional ROI: 0.3%
2977 SOUTHAVEN DRIVE Annapolis, MD This stunning log home on 2.48 scenic acres (with the potential to subdivide) offers the p...	4 beds \| 4 baths \| 3,200 sq.ft.	$925,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.52% Airbnb Rental Income: $null Traditional Rental Income: $3708 Airbnb ROI: N/A Traditional ROI: 2.52%
14 DORSEY AVENUE Annapolis, MD TO BE BUILT / READY TO BE CUSTOMIZED. CONSTRUCTION STARTING SOON Starting at a base pric...	4 beds \| 3 baths \| 2,037 sq.ft.	$600,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.31% Airbnb Rental Income: $null Traditional Rental Income: $3086 Airbnb ROI: N/A Traditional ROI: 4.31%
3117 PORT WAY Annapolis, MD Priced to Sell: Annapolis Hidden Gem in the Sought-After Anchorage Waterfront Community: W...	5 beds \| 3 baths \| 2,288 sq.ft.	$797,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.64% Airbnb Rental Income: $null Traditional Rental Income: $3506 Airbnb ROI: N/A Traditional ROI: 2.64%
3300 SHORE DR Annapolis, MD Stunning Waterfront Coastal Retreat on Oyster Creek with Breathtaking Sunsets! This except...	4 beds \| 4 baths \| N/A	$1,650,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.89% Airbnb Rental Income: $null Traditional Rental Income: $3874 Airbnb ROI: N/A Traditional ROI: 0.89%
1094 LINDEN TREE DRIVE - TAFT MODEL Annapolis, MD Ameri-Star Homes is pleased to offer this incredible opportunity for a to-be-built, crafts...	4 beds \| 3 baths \| 2,580 sq.ft.	$849,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.92% Airbnb Rental Income: $null Traditional Rental Income: $3354 Airbnb ROI: N/A Traditional ROI: 2.92%
2828 BERTH COURT Annapolis, MD !!Price Improvement!! Charming Home in Heritage Harbour 55+ Community Living at Its Finest...	2 beds \| 2 baths \| 1,434 sq.ft.	$529,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.62% Airbnb Rental Income: $null Traditional Rental Income: $2458 Airbnb ROI: N/A Traditional ROI: 2.62%

Your search for investment property begins and ends here

Single Family Homes for Sale in Annapolis, MD

309 MCDONOUGH ROAD

Annapolis, MD

4 beds | 3 baths | 2,945 sq.ft.

$890,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.53%

Airbnb Rental Income: $null

Traditional Rental Income: $3718

Airbnb ROI: N/A

Traditional ROI: 2.53%

1230 CRUMMELL AVENUE

Annapolis, MD

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

$1,250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.16%

Airbnb Rental Income: $null

Traditional Rental Income: $3443

Airbnb ROI: N/A

Traditional ROI: 1.16%

111 CLAY STREET

Annapolis, MD

3 beds | 2 baths | 1,568 sq.ft.

$599,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.9%

Airbnb Rental Income: $null

Traditional Rental Income: $2678

Airbnb ROI: N/A

Traditional ROI: 2.9%

210 BOWEN COURT

Annapolis, MD

5 beds | 4 baths | 4,204 sq.ft.

$1,025,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.42%

Airbnb Rental Income: $null

Traditional Rental Income: $4074

Airbnb ROI: N/A

Traditional ROI: 2.42%

1634 ORCHARD BEACH ROAD

Annapolis, MD

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

$930,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.08%

Airbnb Rental Income: $null

Traditional Rental Income: $3336

Airbnb ROI: N/A

Traditional ROI: 2.08%

1192 BAY HIGHLANDS DRIVE

Annapolis, MD

4 beds | 3 baths | 2,200 sq.ft.

$699,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.22%

Airbnb Rental Income: $null

Traditional Rental Income: $3363

Airbnb ROI: N/A

Traditional ROI: 3.22%

39 WINDWHISPER LN

Annapolis, MD

3 beds | 4 baths | N/A

$750,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.65%

Airbnb Rental Income: $null

Traditional Rental Income: $3397

Airbnb ROI: N/A

Traditional ROI: 2.65%

1096 LINDEN TREE DR

Annapolis, MD

3 beds | 1 baths | N/A

$535,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.73%

Airbnb Rental Income: $null

Traditional Rental Income: $2896

Airbnb ROI: N/A