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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1394 STONECREEK RD Annapolis, MD Offer has been received and we have set an offer deadline of 3 PM on Tuesday 1/14 for the ...	4 beds \| 4 baths \| N/A	$585,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 2.85% Airbnb Rental Income: $3104 Traditional Rental Income: $2779 Airbnb ROI: 2.15% Traditional ROI: 2.85%
474 Ruffian Ct Annapolis, MD Freshly updated Three Bath & Two Bath home featuring new flooring, fresh paint, stainless ...	3 beds \| 2 baths \| 1,232 sq.ft.	$369,500	Airbnb cash on cash: 4.01% Traditional cash on cash: 4.76% Airbnb Rental Income: $2680 Traditional Rental Income: $2303 Airbnb ROI: 4.01% Traditional ROI: 4.76%
1213 Mckinley St Annapolis, MD Here's your chance to live in the Heart of Eastport! Cute cape cod with new kitchen and re...	3 beds \| 1 baths \| 1,008 sq.ft.	$449,000	Airbnb cash on cash: 2.93% Traditional cash on cash: 2.42% Airbnb Rental Income: $2680 Traditional Rental Income: $1833 Airbnb ROI: 2.93% Traditional ROI: 2.42%
900 COACHWAY Annapolis, MD MID-CENTURY MODERN HOME IN THE DOWNS ON THE SEVERN! ALL OFFERS DUE AT 8PM SUNDAY 1/25/26. ...	3 beds \| 3 baths \| N/A	$824,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 1.23% Airbnb Rental Income: $2680 Traditional Rental Income: $2635 Airbnb ROI: 0.46% Traditional ROI: 1.23%
1909 Eleanor Ct Annapolis, MD Welcome to 1909 Eleanor Ct, a stunning colonial featuring five bedrooms and three and a ha...	5 beds \| 3 baths \| 4,790 sq.ft.	$950,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 2.23% Airbnb Rental Income: $3871 Traditional Rental Income: $3869 Airbnb ROI: 1.29% Traditional ROI: 2.23%
847 WOODMONT RD Annapolis, MD Welcome Home to Comfort, Convenience & Community Living This well-maintained 2-bedroom, 2...	2 beds \| 2 baths \| N/A	$689,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 1.37% Airbnb Rental Income: $2338 Traditional Rental Income: $2163 Airbnb ROI: 0.74% Traditional ROI: 1.37%
547 LEFTWICH LN #88 Annapolis, MD BIG PRICE IMPROVEMENT! COSMOPOLITAN ANNAPOLIS TOWNHOME BOASTING SKYLINE ROOFTOP DECK! ADM...	3 beds \| 3 baths \| N/A	$560,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 3.49% Airbnb Rental Income: $2680 Traditional Rental Income: $2973 Airbnb ROI: 1.71% Traditional ROI: 3.49%
38 HARBOUR HEIGHTS DR Annapolis, MD Welcome home to the highly sought-after Seabreeze Harbour Gates community! This SUN lit en...	3 beds \| 3 baths \| N/A	$415,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 2.36% Airbnb Rental Income: $2680 Traditional Rental Income: $2024 Airbnb ROI: 2.41% Traditional ROI: 2.36%
406 Harbor Dr Annapolis, MD Welcome to 406 Harbor Drive, an exceptional residence in the heart of Hillsmere Shores, on...	4 beds \| 3 baths \| 4,000 sq.ft.	$795,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 2.11% Airbnb Rental Income: $3104 Traditional Rental Income: $3202 Airbnb ROI: 1.03% Traditional ROI: 2.11%
1915 Towne Centre Blvd #707 Annapolis, MD Fantastic 2 Bedroom condo with great views of Annapolis Towne Centre from the balcony with...	2 beds \| 2 baths \| 1,246 sq.ft.	$535,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 0.82% Airbnb Rental Income: $2338 Traditional Rental Income: $2514 Airbnb ROI: -0.68% Traditional ROI: 0.82%
1009 OLD BAY RIDGE Road Annapolis, MD Rare double-lot opportunity in water-privileged Annapolis Roads! This beautifully updated ...	4 beds \| 4 baths \| 2,845 sq.ft.	$899,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 2.21% Airbnb Rental Income: $3104 Traditional Rental Income: $3390 Airbnb ROI: 1.03% Traditional ROI: 2.21%
2707 Judson Pl Annapolis, MD Welcome to 2707 Judson Place in Riva Woods. This inviting home sits on a private, fenced c...	3 beds \| 2 baths \| 2,156 sq.ft.	$590,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 3.7% Airbnb Rental Income: $2680 Traditional Rental Income: $3172 Airbnb ROI: 1.65% Traditional ROI: 3.7%
328 Bulwark Aly Annapolis, MD Big price reduction for this beautifully maintained 3 level end unit garage townhome in th...	3 beds \| 2 baths \| 2,000 sq.ft.	$598,500	Airbnb cash on cash: 1.28% Traditional cash on cash: 3.35% Airbnb Rental Income: $2680 Traditional Rental Income: $3200 Airbnb ROI: 1.28% Traditional ROI: 3.35%
66 Franklin St #214 Annapolis, MD Truly one of a kind, this exceptional 1-bedroom, 2 full-bath residence in sought-after Act...	1 beds \| 2 baths \| 1,821 sq.ft.	$840,000	Airbnb cash on cash: -1.93% Traditional cash on cash: -0.27% Airbnb Rental Income: $1744 Traditional Rental Income: $2559 Airbnb ROI: -1.93% Traditional ROI: -0.27%
106 Stilly Way Annapolis, MD This stunning home is move-in ready and boasts high-end upgrades throughout. It features a...	4 beds \| 4 baths \| 4,594 sq.ft.	$983,540	Airbnb cash on cash: 1.25% Traditional cash on cash: 3.75% Airbnb Rental Income: $3104 Traditional Rental Income: $4686 Airbnb ROI: 1.25% Traditional ROI: 3.75%
212 Duke Of Gloucester St Annapolis, MD Welcome to 212 Duke of Gloucester- a prime development opportunity in the heart of histori...	N/A beds \| N/A baths \| 2,300 sq.ft.	$599,900	Airbnb cash on cash: -0.06% Traditional cash on cash: 2.77% Airbnb Rental Income: $1884 Traditional Rental Income: $2964 Airbnb ROI: -0.06% Traditional ROI: 2.77%
1915 Towne Centre Blvd #1210 Annapolis, MD FABULOUS PENTHOUSE. Embrace a lifestyle of unparalleled luxury and breathtaking views wit...	3 beds \| 3 baths \| 3,520 sq.ft.	$1,695,000	Airbnb cash on cash: -2.51% Traditional cash on cash: -1.69% Airbnb Rental Income: $2680 Traditional Rental Income: $3337 Airbnb ROI: -2.51% Traditional ROI: -1.69%
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: 2.49% Traditional cash on cash: 4.23% Airbnb Rental Income: $3104 Traditional Rental Income: $3325 Airbnb ROI: 2.49% Traditional ROI: 4.23%
1165 Green Holly Ct Annapolis, MD Cape St. Claire Home sold with Extra Lot and Detached Garage Plans! Plans in Documents. Th...	3 beds \| 2 baths \| 2,218 sq.ft.	$535,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 3.78% Airbnb Rental Income: $2680 Traditional Rental Income: $2901 Airbnb ROI: 2.06% Traditional ROI: 3.78%
1141 MAINSAIL DR Annapolis, MD PRICE ADJUSTED on this wonderful 4-bedroom home! Welcome to one of Annapolis' most sought-...	4 beds \| 3 baths \| N/A	$890,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 2.15% Airbnb Rental Income: $3104 Traditional Rental Income: $3431 Airbnb ROI: 0.9% Traditional ROI: 2.15%
2555 Riva Rd Annapolis, MD Hard Hat Tours are now available by appointment! Early buyers have the opportunity to cust...	3 beds \| 3 baths \| 3,100 sq.ft.	$1,350,000	Airbnb cash on cash: -1.22% Traditional cash on cash: 0.52% Airbnb Rental Income: $2680 Traditional Rental Income: $4230 Airbnb ROI: -1.22% Traditional ROI: 0.52%
553 Choptank Cove Ct Annapolis, MD For limited time, Sellers will pay $20,000 towards closing costs. English Tudor featuring ...	5 beds \| 4 baths \| 3,759 sq.ft.	$1,076,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 1.57% Airbnb Rental Income: $3871 Traditional Rental Income: $3446 Airbnb ROI: 1.16% Traditional ROI: 1.57%
769 ROBINHOOD RD Annapolis, MD 769 Robinhood Road is one of the most desirable Waterfront properties in Sherwood Forest....	3 beds \| 2 baths \| N/A	$1,250,000	Airbnb cash on cash: -0.61% Traditional cash on cash: -0.01% Airbnb Rental Income: $2680 Traditional Rental Income: $2751 Airbnb ROI: -0.61% Traditional ROI: -0.01%
208 Sellew Rd Annapolis, MD Hard Hat Tours are now available by appointment! Early buyers have the opportunity to cust...	3 beds \| 3 baths \| 3,100 sq.ft.	$1,375,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 1.82% Airbnb Rental Income: $2680 Traditional Rental Income: $4230 Airbnb ROI: 0.11% Traditional ROI: 1.82%
111 Janwall St Annapolis, MD SELLER IS OFFERING $10,000 SETTLEMENT HELP! This beautiful home is ideally situated in a q...	3 beds \| 2 baths \| 1,754 sq.ft.	$599,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 3.27% Airbnb Rental Income: $2680 Traditional Rental Income: $2979 Airbnb ROI: 1.6% Traditional ROI: 3.27%
7101 Bay Front Dr #204 Annapolis, MD Gorgeous 1 bedroom, 1.5 bath condo on the second floor. Freshly painted and new carpet hav...	1 beds \| 1 baths \| 1,000 sq.ft.	$320,000	Airbnb cash on cash: -15.92% Traditional cash on cash: -14.79% Airbnb Rental Income: $1744 Traditional Rental Income: $1605 Airbnb ROI: -15.92% Traditional ROI: -14.79%
1167 Green Holly Dr Annapolis, MD 1167 Green Holly Dr, GIBSON ISLAND, MD 21409 \| Other	N/A beds \| N/A baths \| N/A	$160,000	Airbnb cash on cash: 6.35% Traditional cash on cash: 3.6% Airbnb Rental Income: $1884 Traditional Rental Income: $960 Airbnb ROI: 6.35% Traditional ROI: 3.6%
1915 Towne Centre Blvd #405 & 406 Annapolis, MD A rare opportunity at the Annapolis Town Center - two units combined into one stunning res...	4 beds \| 3 baths \| 3,422 sq.ft.	$3,399,000	Airbnb cash on cash: -1.4% Traditional cash on cash: -1.27% Airbnb Rental Income: $3104 Traditional Rental Income: $2811 Airbnb ROI: -1.4% Traditional ROI: -1.27%
41 Cornhill St Annapolis, MD 41 Cornhill St, Annapolis, MD 21401 \| Townhouse	4 beds \| 2 baths \| 4,404 sq.ft.	$2,100,000	Airbnb cash on cash: -0.9% Traditional cash on cash: -0.96% Airbnb Rental Income: $3104 Traditional Rental Income: $2278 Airbnb ROI: -0.9% Traditional ROI: -0.96%
1814 PLEASANT PLAINS RD Annapolis, MD RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO...	5 beds \| 2 baths \| N/A	$1,300,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 0.32% Airbnb Rental Income: $3871 Traditional Rental Income: $3002 Airbnb ROI: 0.35% Traditional ROI: 0.32%
1814 & 1836 PLEASANT PLAINS & CHERRY RD Annapolis, MD RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO...	5 beds \| 2 baths \| N/A	$1,300,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 0.46% Airbnb Rental Income: $3871 Traditional Rental Income: $2971 Airbnb ROI: 0.52% Traditional ROI: 0.46%
920 OLD ANNAPOLIS NECK Road Annapolis, MD Discover the perfect blend of privacy, lifestyle, and location on the highly coveted Annap...	4 beds \| 3 baths \| 2,552 sq.ft.	$719,995	Airbnb cash on cash: 1.49% Traditional cash on cash: 2.86% Airbnb Rental Income: $3104 Traditional Rental Income: $3317 Airbnb ROI: 1.49% Traditional ROI: 2.86%
51 Franklin St Annapolis, MD An exclusive and rare opportunity could be yours! Welcome to 51 Franklin, consisting of 9 ...	2 beds \| 2 baths \| 2,269 sq.ft.	$1,695,000	Airbnb cash on cash: -2.1% Traditional cash on cash: -1.19% Airbnb Rental Income: $2338 Traditional Rental Income: $3192 Airbnb ROI: -2.1% Traditional ROI: -1.19%
7002 CHANNEL VILLAGE Court unit: 101 #101 Annapolis, MD PRICE PRICE PRICE!!!! Welcome to Chesapeake Harbour! This beautifully updated Marina VIEW ...	2 beds \| 2 baths \| 1,319 sq.ft.	$525,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 2.91% Airbnb Rental Income: $2338 Traditional Rental Income: $2356 Airbnb ROI: 1.69% Traditional ROI: 2.91%
411 Ridgely Ave Annapolis, MD 411 Ridgely Ave, Annapolis, MD 21401 \| Single Family Residential	4 beds \| 4 baths \| 5,950 sq.ft.	$3,950,000	Airbnb cash on cash: -1.46% Traditional cash on cash: -1.25% Airbnb Rental Income: $3104 Traditional Rental Income: $3143 Airbnb ROI: -1.46% Traditional ROI: -1.25%
606 JAMES WALKER PL Annapolis, MD Existing / Assumable-VA Loan at a favorable 2.5% interest rate! Welcome to Annapolis Towne...	3 beds \| 5 baths \| N/A	$605,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 2.43% Airbnb Rental Income: $2680 Traditional Rental Income: $2710 Airbnb ROI: 1.25% Traditional ROI: 2.43%

Real Estate investment in Annapolis, MD

There are 74 properties for sale in the city of Annapolis . The median list price in Annapolis is $605,000 and the average price per square foot is $284. In February 2026, the average monthly cash on cash return in Annapolis is 1.00%. The average monthly rental income in Annapolis is $2,328.

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

There are 74 investment properties available for sale in Annapolis.

In 2026, the best neighborhood to buy investment property is Annapolis.

The ROI for Short-Term is higher than the Long-Term in Annapolis with average rental income of $2,680.

Your search for investment property begins and ends here

Investment Property for Sale in Annapolis, MD

1394 STONECREEK RD

Annapolis, MD

4 beds | 4 baths | N/A

$585,000

Airbnb cash on cash: 2.15%

Traditional cash on cash: 2.85%

Airbnb Rental Income: $3104

Traditional Rental Income: $2779

Airbnb ROI: 2.15%

Traditional ROI: 2.85%

474 Ruffian Ct

Annapolis, MD

3 beds | 2 baths | 1,232 sq.ft.

$369,500

Airbnb cash on cash: 4.01%

Traditional cash on cash: 4.76%

Airbnb Rental Income: $2680

Traditional Rental Income: $2303

Airbnb ROI: 4.01%

Traditional ROI: 4.76%

1213 Mckinley St

Annapolis, MD

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

$449,000

Airbnb cash on cash: 2.93%

Traditional cash on cash: 2.42%

Airbnb Rental Income: $2680

Traditional Rental Income: $1833

Airbnb ROI: 2.93%

Traditional ROI: 2.42%

900 COACHWAY

Annapolis, MD

3 beds | 3 baths | N/A

$824,000

Airbnb cash on cash: 0.46%

Traditional cash on cash: 1.23%

Airbnb Rental Income: $2680

Traditional Rental Income: $2635

Airbnb ROI: 0.46%

Traditional ROI: 1.23%

1909 Eleanor Ct

Annapolis, MD

5 beds | 3 baths | 4,790 sq.ft.

$950,000

Airbnb cash on cash: 1.29%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $3871

Traditional Rental Income: $3869

Airbnb ROI: 1.29%

Traditional ROI: 2.23%

847 WOODMONT RD

Annapolis, MD

2 beds | 2 baths | N/A

$689,000

Airbnb cash on cash: 0.74%

Traditional cash on cash: 1.37%

Airbnb Rental Income: $2338

Traditional Rental Income: $2163

Airbnb ROI: 0.74%

Traditional ROI: 1.37%

547 LEFTWICH LN #88

Annapolis, MD

3 beds | 3 baths | N/A

$560,000

Airbnb cash on cash: 1.71%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $2680

Traditional Rental Income: $2973

Airbnb ROI: 1.71%

Traditional ROI: 3.49%

38 HARBOUR HEIGHTS DR

Annapolis, MD

3 beds | 3 baths | N/A

$415,000

Airbnb cash on cash: 2.41%

Traditional cash on cash: 2.36%

Airbnb Rental Income: $2680

Traditional Rental Income: $2024

Airbnb ROI: 2.41%