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 56 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
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%
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	$700,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 2.91% Airbnb Rental Income: $2680 Traditional Rental Income: $3397 Airbnb ROI: 0.84% Traditional ROI: 2.91%
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: 2.03% Traditional cash on cash: 3.73% Airbnb Rental Income: $2680 Traditional Rental Income: $2896 Airbnb ROI: 2.03% Traditional ROI: 3.73%
1034 SAINT MARGARETS DR Annapolis, MD Welcome home to this well maintained four bedroom, two and a half bath property in sought ...	4 beds \| 3 baths \| N/A	$545,000	Airbnb cash on cash: 2.64% Traditional cash on cash: 4.47% Airbnb Rental Income: $3104 Traditional Rental Income: $3333 Airbnb ROI: 2.64% Traditional ROI: 4.47%
1011 HYDE PARK DR Annapolis, MD This updated home offers 3 bedrooms and 2 full baths, with flexible living spaces througho...	3 beds \| 2 baths \| N/A	$575,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 2.39% Airbnb Rental Income: $2680 Traditional Rental Income: $2432 Airbnb ROI: 1.66% Traditional ROI: 2.39%
1411 STONECREEK RD Annapolis, MD Open House Saturday 10/11/25 12-2 pm. Price reduction on a perfect single family home in A...	4 beds \| 4 baths \| N/A	$559,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 4.98% Airbnb Rental Income: $3104 Traditional Rental Income: $3771 Airbnb ROI: 2.35% Traditional ROI: 4.98%
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%
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: -1.12% Traditional cash on cash: -1.03% Airbnb Rental Income: $1744 Traditional Rental Income: $1412 Airbnb ROI: -1.12% Traditional ROI: -1.03%
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: -0.32% Traditional cash on cash: -0.18% Airbnb Rental Income: $2338 Traditional Rental Income: $1916 Airbnb ROI: -0.32% Traditional ROI: -0.18%
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%
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: -0.07% Traditional cash on cash: 0.89% Airbnb Rental Income: $3104 Traditional Rental Income: $3874 Airbnb ROI: -0.07% Traditional ROI: 0.89%
553 CHOPTANK COVE CT Annapolis, MD English Tudor featuring a stone front patio for nature lovers and bird watchers. Surroun...	5 beds \| 4 baths \| N/A	$1,077,000	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%
1901 EAMONS WAY Annapolis, MD OPEN HOUSE SUNDAY, SEPTEMBER 21ST FROM 11 AM TO 1 PM. Tucked away at the end of a quiet ...	3 beds \| 4 baths \| N/A	$825,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 2.15% Airbnb Rental Income: $2680 Traditional Rental Income: $3236 Airbnb ROI: 0.6% Traditional ROI: 2.15%
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%
7 SILOPANNA RD Annapolis, MD Welcome to this beautifully restored and thoughtfully updated 1942 gem. Step inside to fi...	4 beds \| 3 baths \| N/A	$729,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 3.44% Airbnb Rental Income: $3104 Traditional Rental Income: $3557 Airbnb ROI: 1.74% Traditional ROI: 3.44%
3307 HARNESS CREEK RD Annapolis, MD Welcome to 3307 Harness Creek Road-- a Nantucket style, coastal home with spectacular wate...	3 beds \| 3 baths \| N/A	$3,195,000	Airbnb cash on cash: -0.82% Traditional cash on cash: -0.55% Airbnb Rental Income: $2680 Traditional Rental Income: $2863 Airbnb ROI: -0.82% Traditional ROI: -0.55%
303 RIDING RIDGE RD Annapolis, MD Welcome to the sought-after Hunt Meadow Community! This three level, 4 bedroom and 2.5 ba...	4 beds \| 3 baths \| N/A	$729,700	Airbnb cash on cash: 1.48% Traditional cash on cash: 2.88% Airbnb Rental Income: $3104 Traditional Rental Income: $3350 Airbnb ROI: 1.48% Traditional ROI: 2.88%
102 BOXWOOD Road Annapolis, MD This lovely home in Annapolis is now available at a reduced price! 4bd, 1.5ba Raised Ranch...	4 beds \| 2 baths \| 1,296 sq.ft.	$489,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 3.98% Airbnb Rental Income: $3104 Traditional Rental Income: $2765 Airbnb ROI: 3.17% Traditional ROI: 3.98%
2175 GLENCREST CIRCLE - GEORGETOWN MODEL Annapolis, MD Ameri-Star Homes, one of the area's premier homebuilders, is excited to be offering our sp...	3 beds \| 2 baths \| 1,757 sq.ft.	$799,990	Airbnb cash on cash: 0.53% Traditional cash on cash: 1.51% Airbnb Rental Income: $2680 Traditional Rental Income: $2775 Airbnb ROI: 0.53% Traditional ROI: 1.51%
2656-A Queen Anne Cir Annapolis, MD 2656-A Queen Anne Cir, Annapolis, MD 21403 \| Single Family Residential	4 beds \| 4 baths \| 3,405 sq.ft.	$1,730,000	Airbnb cash on cash: -0.65% Traditional cash on cash: -0.22% Airbnb Rental Income: $3104 Traditional Rental Income: $3091 Airbnb ROI: -0.65% Traditional ROI: -0.22%
1150 LITTLE MAGOTHY VIEW Annapolis, MD *Seller accepted an offer prior to going active*** Open House cancelled. Welcome to t...	3 beds \| 2 baths \| N/A	$575,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 2.09% Airbnb Rental Income: $2680 Traditional Rental Income: $2179 Airbnb ROI: 1.84% Traditional ROI: 2.09%
192 Duke Of Gloucester Annapolis, MD 192 Duke Of Gloucester, Annapolis, MD 21401 \| Single Family Residential	6 beds \| 4 baths \| 3,415 sq.ft.	$2,100,000	Airbnb cash on cash: -0.57% Traditional cash on cash: -0.47% Airbnb Rental Income: $3871 Traditional Rental Income: $3245 Airbnb ROI: -0.57% Traditional ROI: -0.47%
1100 BROADVIEW DR Annapolis, MD Stunning Waterview Home in Prime Water Privileged Neighborhood Discover this beautiful, s...	4 beds \| 4 baths \| N/A	$825,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 1.8% Airbnb Rental Income: $3104 Traditional Rental Income: $2801 Airbnb ROI: 1.28% Traditional ROI: 1.8%
22 East Lake Dr Annapolis, MD 22 East Lake Dr, Annapolis, MD 21403 \| Single Family Residential	3 beds \| 3 baths \| 3,320 sq.ft.	$2,775,000	Airbnb cash on cash: -1.34% Traditional cash on cash: -1.2% Airbnb Rental Income: $2680 Traditional Rental Income: $2404 Airbnb ROI: -1.34% Traditional ROI: -1.2%
1864 Milvale Rd Annapolis, MD 1864 Milvale Rd, Annapolis, MD 21409 \| Single Family Residential	4 beds \| 5 baths \| 7,684 sq.ft.	$5,450,000	Airbnb cash on cash: -1.63% Traditional cash on cash: -1.26% Airbnb Rental Income: $3104 Traditional Rental Income: $4281 Airbnb ROI: -1.63% Traditional ROI: -1.26%
1241 Cherry Tree Ln Annapolis, MD 1241 Cherry Tree Ln, Annapolis, MD 21403 \| Single Family Residential	5 beds \| 5 baths \| 6,428 sq.ft.	$2,675,000	Airbnb cash on cash: -1% Traditional cash on cash: -0.36% Airbnb Rental Income: $3871 Traditional Rental Income: $4627 Airbnb ROI: -1% Traditional ROI: -0.36%
2514 Lyon Dr Annapolis, MD 2514 Lyon Dr, Annapolis, MD 21403 \| Single Family Residential	6 beds \| 6 baths \| 5,678 sq.ft.	$3,850,000	Airbnb cash on cash: -1.26% Traditional cash on cash: -0.45% Airbnb Rental Income: $3871 Traditional Rental Income: $5931 Airbnb ROI: -1.26% Traditional ROI: -0.45%
2512 Lyon Dr Annapolis, MD 2512 Lyon Dr, Annapolis, MD 21403 \| Single Family Residential	4 beds \| 3 baths \| 4,587 sq.ft.	$3,875,000	Airbnb cash on cash: -1.44% Traditional cash on cash: -1.26% Airbnb Rental Income: $3104 Traditional Rental Income: $3066 Airbnb ROI: -1.44% Traditional ROI: -1.26%
1900 Carrollton Rd Annapolis, MD 1900 Carrollton Rd, Annapolis, MD 21409 \| Single Family Residential	7 beds \| 6 baths \| 12,200 sq.ft.	$8,995,000	Airbnb cash on cash: -1.73% Traditional cash on cash: -1.4% Airbnb Rental Income: $3871 Traditional Rental Income: $5816 Airbnb ROI: -1.73% Traditional ROI: -1.4%
2680 Claibourne Ct Annapolis, MD 2680 Claibourne Ct, Annapolis, MD 21403 \| Single Family Residential	5 beds \| 4 baths \| 3,415 sq.ft.	$2,595,000	Airbnb cash on cash: -0.86% Traditional cash on cash: -0.72% Airbnb Rental Income: $3871 Traditional Rental Income: $3375 Airbnb ROI: -0.86% Traditional ROI: -0.72%
122 Roselawn Rd Annapolis, MD 122 Roselawn Rd, Annapolis, MD 21403 \| Single Family Residential	2 beds \| 1 baths \| 700 sq.ft.	$360,000	Airbnb cash on cash: 2.85% Traditional cash on cash: 1.91% Airbnb Rental Income: $2338 Traditional Rental Income: $1441 Airbnb ROI: 2.85% Traditional ROI: 1.91%
Lynnfield Plan Annapolis, MD	4 beds \| 3 baths \| 4,213 sq.ft.	$974,990	Airbnb cash on cash: 0.46% Traditional cash on cash: 0.81% Airbnb Rental Income: $3104 Traditional Rental Income: $2723 Airbnb ROI: 0.46% Traditional ROI: 0.81%
Admiral Plan Annapolis, MD	4 beds \| 4 baths \| 4,483 sq.ft.	$1,034,990	Airbnb cash on cash: 0.31% Traditional cash on cash: 1.06% Airbnb Rental Income: $3104 Traditional Rental Income: $3120 Airbnb ROI: 0.31% Traditional ROI: 1.06%
Kensington Plan Annapolis, MD	4 beds \| 4 baths \| 4,245 sq.ft.	$999,990	Airbnb cash on cash: 0.39% Traditional cash on cash: 1.17% Airbnb Rental Income: $3104 Traditional Rental Income: $3120 Airbnb ROI: 0.39% Traditional ROI: 1.17%
Fitzgerald Plan Annapolis, MD	4 beds \| 3 baths \| 4,336 sq.ft.	$989,990	Airbnb cash on cash: 0.42% Traditional cash on cash: 0.77% Airbnb Rental Income: $3104 Traditional Rental Income: $2723 Airbnb ROI: 0.42% Traditional ROI: 0.77%
93 BAY DR Annapolis, MD SPECTACULAR WATER VIEWS OF THE THE CHESPEAKE BAY! LOCATION LOCATION! Don't MISS this RARE ...	3 beds \| 1 baths \| N/A	$2,895,000	Airbnb cash on cash: -0.88% Traditional cash on cash: -0.94% Airbnb Rental Income: $2680 Traditional Rental Income: $1900 Airbnb ROI: -0.88% Traditional ROI: -0.94%
210 CANTERWOOD CT Annapolis, MD Welcome to 210 Canterwood Court, located in the beautiful community of Old Mill Bottom Est...	5 beds \| 4 baths \| N/A	$1,375,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 1.1% Airbnb Rental Income: $3871 Traditional Rental Income: $3784 Airbnb ROI: 0.51% Traditional ROI: 1.1%
9 TOLSON ST Annapolis, MD Welcome to 9 Tolson, a home that perfectly combines charm, convenience, and timeless desig...	4 beds \| 3 baths \| N/A	$1,475,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 0.09% Airbnb Rental Income: $3104 Traditional Rental Income: $2593 Airbnb ROI: -0.05% Traditional ROI: 0.09%
341 Dubois Rd Annapolis, MD 341 Dubois Rd, Annapolis, MD 21401 \| Single Family Residential	7 beds \| 8 baths \| 9,570 sq.ft.	$2,750,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 0.2% Airbnb Rental Income: $3871 Traditional Rental Income: $5914 Airbnb ROI: -0.93% Traditional ROI: 0.2%
1227 HAMPTON RD Annapolis, MD Welcome to 1227 Hampton Road in Cape St. Claire, a home that blends comfort, flexibility, ...	4 beds \| 2 baths \| N/A	$585,000	Airbnb cash on cash: 2.37% Traditional cash on cash: 3.16% Airbnb Rental Income: $3104 Traditional Rental Income: $2827 Airbnb ROI: 2.37% Traditional ROI: 3.16%

Your search for investment property begins and ends here

Single Family Homes for Sale in Annapolis, MD

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%

39 WINDWHISPER LN

Annapolis, MD

3 beds | 4 baths | N/A

$700,000

Airbnb cash on cash: 0.84%

Traditional cash on cash: 2.91%

Airbnb Rental Income: $2680

Traditional Rental Income: $3397

Airbnb ROI: 0.84%

Traditional ROI: 2.91%

1096 LINDEN TREE DR

Annapolis, MD

3 beds | 1 baths | N/A

$535,000

Airbnb cash on cash: 2.03%

Traditional cash on cash: 3.73%

Airbnb Rental Income: $2680

Traditional Rental Income: $2896

Airbnb ROI: 2.03%

Traditional ROI: 3.73%

1034 SAINT MARGARETS DR

Annapolis, MD

4 beds | 3 baths | N/A

$545,000

Airbnb cash on cash: 2.64%

Traditional cash on cash: 4.47%

Airbnb Rental Income: $3104

Traditional Rental Income: $3333

Airbnb ROI: 2.64%

Traditional ROI: 4.47%

1011 HYDE PARK DR

Annapolis, MD

3 beds | 2 baths | N/A

$575,000

Airbnb cash on cash: 1.66%

Traditional cash on cash: 2.39%

Airbnb Rental Income: $2680

Traditional Rental Income: $2432

Airbnb ROI: 1.66%

Traditional ROI: 2.39%

1411 STONECREEK RD

Annapolis, MD

4 beds | 4 baths | N/A

$559,000

Airbnb cash on cash: 2.35%

Traditional cash on cash: 4.98%

Airbnb Rental Income: $3104

Traditional Rental Income: $3771

Airbnb ROI: 2.35%

Traditional ROI: 4.98%

730 CRISFIELD WAY

Annapolis, MD

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%

1632 WINCHESTER RD

Annapolis, MD

1 beds | 1 baths | N/A

$1,900,000

Airbnb cash on cash: -1.12%

Traditional cash on cash: -1.03%

Airbnb Rental Income: $1744

Traditional Rental Income: $1412

Airbnb ROI: -1.12%