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.

San Rafael Hill Investment Property for Sale in Annapolis, MD

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

Showing 194 San Rafael Hill Investment Property 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
926 YACHTSMAN Way Annapolis, MD Welcome to 926 Yachtsman Way - a rare single-level home in the City of Annapolis offering ...	2 beds \| 2 baths \| 1,174 sq.ft.	$415,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 3.29% Airbnb Rental Income: $2338 Traditional Rental Income: $2317 Airbnb ROI: 1.86% Traditional ROI: 3.29%
1915 TOWNE CENTRE Boulevard unit: 807 #807 Annapolis, MD FRESH INTERIOR PAINT THROUGHOUT - A PRISTINE, NEUTRAL PALETTE READY FOR YOUR STYLE!! SELLE...	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%
474 RUFFIAN Court Annapolis, MD Freshly updated Three Bath & Two Bath home featuring new flooring, fresh paint, stainless ...	3 beds \| 2 baths \| 1,232 sq.ft.	$374,950	Airbnb cash on cash: 3.96% Traditional cash on cash: 4.7% Airbnb Rental Income: $2680 Traditional Rental Income: $2303 Airbnb ROI: 3.96% Traditional ROI: 4.7%
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%
201 BOWIE Avenue Annapolis, MD Beautifully Updated Annapolis Home Near Navy Stadium!! Welcome to 201 Bowie Ave, a turnkey...	4 beds \| 3 baths \| 1,709 sq.ft.	$574,900	Airbnb cash on cash: 2.34% Traditional cash on cash: 3.21% Airbnb Rental Income: $3104 Traditional Rental Income: $2866 Airbnb ROI: 2.34% Traditional ROI: 3.21%
27 DORSEY AVE Annapolis, MD Step into this beautifully renovated Annapolis charmer - completely updated from the groun...	2 beds \| 1 baths \| N/A	$349,900	Airbnb cash on cash: 3.01% Traditional cash on cash: 2.34% Airbnb Rental Income: $2338 Traditional Rental Income: $1538 Airbnb ROI: 3.01% Traditional ROI: 2.34%
3182 HARNESS CREEK Road Annapolis, MD Incredible value for this newly completed waterfront estate - now offered at $10,250,000. ...	4 beds \| 6 baths \| 5,375 sq.ft.	$10,250,000	Airbnb cash on cash: -0.9% Traditional cash on cash: -0.35% Airbnb Rental Income: $3104 Traditional Rental Income: $7639 Airbnb ROI: -0.9% Traditional ROI: -0.35%
215 CHESTER Avenue Annapolis, MD Embrace the Eastport lifestyle in this charming craftsman just steps from the water and do...	4 beds \| 4 baths \| 3,421 sq.ft.	$1,895,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 0.28% Airbnb Rental Income: $3104 Traditional Rental Income: $3908 Airbnb ROI: -0.57% Traditional ROI: 0.28%
103 NORMA Alley Annapolis, MD OPEN HOUSE Sunday 2-4PM Please join us to see this beautiful and updated townhome located ...	4 beds \| 5 baths \| 2,475 sq.ft.	$695,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 3.17% Airbnb Rental Income: $3104 Traditional Rental Income: $3727 Airbnb ROI: 1.12% Traditional ROI: 3.17%
1071 CEDAR RIDGE COURT Annapolis, MD $5,000 decorating allowance will be offered to Buyer with an acceptable offer! Nestled in ...	3 beds \| 3 baths \| 1,320 sq.ft.	$395,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 3.73% Airbnb Rental Income: $2680 Traditional Rental Income: $2469 Airbnb ROI: 2.58% Traditional ROI: 3.73%
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%
1909 ELEANOR Court Annapolis, MD Welcome to 1909 Eleanor Ct, a stunning colonial featuring five bedrooms and three and a ha...	5 beds \| 4 baths \| 4,790 sq.ft.	$935,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 2.29% Airbnb Rental Income: $3871 Traditional Rental Income: $3869 Airbnb ROI: 1.34% Traditional ROI: 2.29%
8 ASHFORD CT Annapolis, MD Price Adjustment! Welcome to 8 Ashford Ct - Modern Living in the Heart of Annapolis! Now o...	2 beds \| 2 baths \| N/A	$399,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 2.97% Airbnb Rental Income: $2338 Traditional Rental Income: $2034 Airbnb ROI: 2.23% Traditional ROI: 2.97%
1984 MARCONI Circle Annapolis, MD Perfect Heritage Harbour Location. Lovely end of row unit with additional daylight through...	2 beds \| 2 baths \| 1,434 sq.ft.	$489,900	Airbnb cash on cash: 1.71% Traditional cash on cash: 3.2% Airbnb Rental Income: $2338 Traditional Rental Income: $2445 Airbnb ROI: 1.71% Traditional ROI: 3.2%
1553 STAR PINE Drive Annapolis, MD Welcome to your new home in Whispering Woods! This charming duplex offers practical living...	2 beds \| 2 baths \| 1,060 sq.ft.	$346,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 4.37% Airbnb Rental Income: $2338 Traditional Rental Income: $2165 Airbnb ROI: 3.12% Traditional ROI: 4.37%
2900 SHIPMASTER WAY #216 Annapolis, MD Welcome to Waterfront living at its finest! This exclusive second floor unit is a rare gem...	2 beds \| 2 baths \| N/A	$347,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 4.76% Airbnb Rental Income: $2338 Traditional Rental Income: $2221 Airbnb ROI: 3.34% Traditional ROI: 4.76%
122 WATERLINE Court Annapolis, MD Just Reduced and Open Sunday 11AM-1PM! Elegant and refined, this home is the upscale A...	4 beds \| 5 baths \| 2,450 sq.ft.	$605,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 4.56% Airbnb Rental Income: $3104 Traditional Rental Income: $3916 Airbnb ROI: 1.87% Traditional ROI: 4.56%
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%
161 E BAY VIEW DR Annapolis, MD Welcome home to this fantastic contemporary style where coastal charm meets modern connive...	4 beds \| 4 baths \| N/A	$949,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 2.13% Airbnb Rental Income: $3104 Traditional Rental Income: $3705 Airbnb ROI: 0.65% Traditional ROI: 2.13%
2013 WARNERS TER S #348 Annapolis, MD Welcome to this stunning 3-bedroom, 2-bath condo nestled in the desirable Rivergate commun...	3 beds \| 2 baths \| N/A	$389,900	Airbnb cash on cash: 3.26% Traditional cash on cash: 3.76% Airbnb Rental Income: $2680 Traditional Rental Income: $2229 Airbnb ROI: 3.26% Traditional ROI: 3.76%
1002 TYLER Avenue Annapolis, MD Location Location location!! Modern rancher style home located near everything Annapolis h...	5 beds \| 2 baths \| 1,920 sq.ft.	$580,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 3.33% Airbnb Rental Income: $3871 Traditional Rental Income: $2932 Airbnb ROI: 3.53% Traditional ROI: 3.33%
627 TRIPP CREEK Court Annapolis, MD Offers received. Deadline Wednesday 12/10 at Noon. This beautiful end-of-row townhouse on ...	4 beds \| 3 baths \| 1,822 sq.ft.	$369,999	Airbnb cash on cash: 4.52% Traditional cash on cash: 6.03% Airbnb Rental Income: $3104 Traditional Rental Income: $2920 Airbnb ROI: 4.52% Traditional ROI: 6.03%
932 RIVERSEDGE CIR Annapolis, MD Welcome to 932 Riversedge Circle - a beautifully updated, one-level end-unit townhome in d...	2 beds \| 1 baths \| N/A	$389,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 1.73% Airbnb Rental Income: $2338 Traditional Rental Income: $1398 Airbnb ROI: 2.72% Traditional ROI: 1.73%
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.	$925,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 0.85% Airbnb Rental Income: $2680 Traditional Rental Income: $2797 Airbnb ROI: -0.03% Traditional ROI: 0.85%
304-G HILLTOP Lane Annapolis, MD Welcome home! This beautiful 2-bedroom, 2-bath condo in Annapolis! This spacious unit offe...	2 beds \| 2 baths \| 1,072 sq.ft.	$285,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 5.09% Airbnb Rental Income: $2338 Traditional Rental Income: $2031 Airbnb ROI: 4.08% Traditional ROI: 5.09%
165 KING GEORGE Street Annapolis, MD There are so many option available for this property in the heart of Historic Annapolis. Y...	N/A beds \| N/A baths \| 2,649 sq.ft.	$1,375,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 0.68% Airbnb Rental Income: $1884 Traditional Rental Income: $3263 Airbnb ROI: -0.79% Traditional ROI: 0.68%
133 Lake View Dr Annapolis, MD 133 Lake View Dr, Annapolis, MD 21403 \| Single Family Residential	5 beds \| 5 baths \| 4,308 sq.ft.	$1,400,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 1.6% Airbnb Rental Income: $3871 Traditional Rental Income: $4883 Airbnb ROI: 0.18% Traditional ROI: 1.6%
1411 STONECREEK RD Annapolis, MD Price Reduction to under $550K!! Open House Saturday 10/26/25 12-2 pm. Perfect single fami...	4 beds \| 4 baths \| N/A	$549,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 5.09% Airbnb Rental Income: $3104 Traditional Rental Income: $3771 Airbnb ROI: 2.41% Traditional ROI: 5.09%
2707 JUDSON Place Annapolis, MD Welcome to 2707 Judson Place in Riva Woods. This inviting home sits on a private, fenced c...	3 beds \| 3 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%
1 TUCKER Street Annapolis, MD 30K Price Improvement! Seller motivated! Incredible West Annapolis home that has been reno...	3 beds \| 3 baths \| 1,869 sq.ft.	$1,145,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 1.05% Airbnb Rental Income: $2680 Traditional Rental Income: $3155 Airbnb ROI: 0.01% Traditional ROI: 1.05%
2203 MULBERRY HILL Road Annapolis, MD Bring your personal touch to this waterfront get away and enjoy the waterfront lifestyle! ...	3 beds \| 3 baths \| 1,994 sq.ft.	$1,350,000	Airbnb cash on cash: -0.13% Traditional cash on cash: -0.6% Airbnb Rental Income: $2680 Traditional Rental Income: $1460 Airbnb ROI: -0.13% Traditional ROI: -0.6%
110 BIKRAM Terrace Annapolis, MD Welcome To 110 Bikram Ter - Classic Annapolis Living Meets Modern Luxury! Experience the b...	3 beds \| 4 baths \| 2,229 sq.ft.	$675,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 2.88% Airbnb Rental Income: $2680 Traditional Rental Income: $3344 Airbnb ROI: 0.81% Traditional ROI: 2.88%
328 BULWARK Alley Annapolis, MD Welcome to this beautifully maintained 3 level end unit garage townhome in the sought afte...	3 beds \| 4 baths \| 2,000 sq.ft.	$619,900	Airbnb cash on cash: 1.46% Traditional cash on cash: 3.46% Airbnb Rental Income: $2680 Traditional Rental Income: $3200 Airbnb ROI: 1.46% Traditional ROI: 3.46%
106 STILLY Way Annapolis, MD This stunning home is move-in ready and boasts high-end upgrades throughout. It features a...	4 beds \| 5 baths \| 4,594 sq.ft.	$974,990	Airbnb cash on cash: 1.27% Traditional cash on cash: 3.79% Airbnb Rental Income: $3104 Traditional Rental Income: $4686 Airbnb ROI: 1.27% Traditional ROI: 3.79%
730 CRISFIELD WAY Annapolis, MD Welcome to Kingsport , a water privileged community packed with beautiful homes and all th...	5 beds \| 5 baths \| N/A	$865,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 3.15% Airbnb Rental Income: $3871 Traditional Rental Income: $4276 Airbnb ROI: 1.62% Traditional ROI: 3.15%
1913 DULANEY Place Annapolis, MD The perfect blend of 1950s charm and modern Annapolis living, situated steps from the wate...	5 beds \| 2 baths \| 2,969 sq.ft.	$925,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 2.25% Airbnb Rental Income: $3871 Traditional Rental Income: $3595 Airbnb ROI: 1.61% Traditional ROI: 2.25%
1955 MARCONI Circle Annapolis, MD Heritage Harbour a 55 plus community. Welcome Home to 1955 Marconi Cir. This two bedroom t...	2 beds \| 2 baths \| 1,200 sq.ft.	$460,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 2.63% Airbnb Rental Income: $2338 Traditional Rental Income: $2217 Airbnb ROI: 1.57% Traditional ROI: 2.63%
48 MURRAY Avenue Annapolis, MD Thoughtfully updated home, preserving the character and charm of Murray Hill while offerin...	4 beds \| 4 baths \| 2,580 sq.ft.	$1,595,000	Airbnb cash on cash: 0.03% Traditional cash on cash: -0.38% Airbnb Rental Income: $3104 Traditional Rental Income: $1796 Airbnb ROI: 0.03% Traditional ROI: -0.38%
301 UNITY Lane Annapolis, MD Walk in and be amazed with a beautiful and luxurious remodeled open floor concept. Open th...	5 beds \| 6 baths \| 7,616 sq.ft.	$1,127,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 3.86% Airbnb Rental Income: $3871 Traditional Rental Income: $6254 Airbnb ROI: 0.79% Traditional ROI: 3.86%
90 E LAKE Drive Annapolis, MD Come explore the shores of Bay Ridge. As Annapolis's premiere waterfront community, Bay Ri...	5 beds \| 6 baths \| 4,204 sq.ft.	$3,795,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 0.05% Airbnb Rental Income: $3871 Traditional Rental Income: $6472 Airbnb ROI: -0.93% Traditional ROI: 0.05%

Your search for investment property begins and ends here

San Rafael Hill Investment Property for Sale in Annapolis, MD

926 YACHTSMAN Way

Annapolis, MD

2 beds | 2 baths | 1,174 sq.ft.

$415,000

Airbnb cash on cash: 1.86%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $2338

Traditional Rental Income: $2317

Airbnb ROI: 1.86%

Traditional ROI: 3.29%

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%

474 RUFFIAN Court

Annapolis, MD

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

$374,950

Airbnb cash on cash: 3.96%

Traditional cash on cash: 4.7%

Airbnb Rental Income: $2680

Traditional Rental Income: $2303

Airbnb ROI: 3.96%

Traditional ROI: 4.7%

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%

201 BOWIE Avenue

Annapolis, MD

4 beds | 3 baths | 1,709 sq.ft.

$574,900

Airbnb cash on cash: 2.34%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $3104

Traditional Rental Income: $2866

Airbnb ROI: 2.34%

Traditional ROI: 3.21%

27 DORSEY AVE

Annapolis, MD

2 beds | 1 baths | N/A

$349,900

Airbnb cash on cash: 3.01%

Traditional cash on cash: 2.34%

Airbnb Rental Income: $2338

Traditional Rental Income: $1538

Airbnb ROI: 3.01%

Traditional ROI: 2.34%

3182 HARNESS CREEK Road

Annapolis, MD

4 beds | 6 baths | 5,375 sq.ft.

$10,250,000

Airbnb cash on cash: -0.9%

Traditional cash on cash: -0.35%

Airbnb Rental Income: $3104

Traditional Rental Income: $7639

Airbnb ROI: -0.9%

Traditional ROI: -0.35%

215 CHESTER Avenue

Annapolis, MD

4 beds | 4 baths | 3,421 sq.ft.

$1,895,000

Airbnb cash on cash: -0.57%

Traditional cash on cash: 0.28%

Airbnb Rental Income: $3104

Traditional Rental Income: $3908

Airbnb ROI: -0.57%