Real Estate Investment Properties for Sale in Saint Michaels, MD

Looking for investment property in Saint Michaels, MD with high ROI ?

Explore a variety of short-term homes & houses in Saint Michaels, MD. Invest wisely with VRBO & Saint Michaels, 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 Saint Michaels, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
408 SPINNAKER LN SAINT MICHAELS, MD OPEN HOUSE Sat 3/21 2 - 4pm and Sun 3/22 10-12pm. This immaculate 4 bedroom, 2.5 bath h...	4 beds \| 3 baths \| N/A	$699,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 2.51% Airbnb Rental Income: $1681 Traditional Rental Income: $3037 Airbnb ROI: -0.29% Traditional ROI: 2.51%
106 CHESTNUT Street E SAINT MICHAELS, MD Luxury Restoration in the Heart of Historic St. Michaels Welcome to 106 E. Chestnut Street...	2 beds \| 3 baths \| 2,282 sq.ft.	$1,325,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 0.72% Airbnb Rental Income: $1640 Traditional Rental Income: $2879 Airbnb ROI: -0.66% Traditional ROI: 0.72%
938 MAREA TERRACE SAINT MICHAELS, MD Fabulous in-town St. Michaels waterfront property - This coastal style waterfront residenc...	4 beds \| 6 baths \| 3,000 sq.ft.	$2,390,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 1.73% Airbnb Rental Income: $1681 Traditional Rental Income: $7308 Airbnb ROI: -1.02% Traditional ROI: 1.73%
24912 BACK CREEK Drive SAINT MICHAELS, MD Back Creek Landing home for sale in St. Michaels, MD - located in one of the town's most d...	3 beds \| 3 baths \| 3,166 sq.ft.	$795,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 0.99% Airbnb Rental Income: $2491 Traditional Rental Income: $2170 Airbnb ROI: 0.61% Traditional ROI: 0.99%
23961 LYNNEWOOD Drive SAINT MICHAELS, MD Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends ...	4 beds \| 4 baths \| 4,035 sq.ft.	$3,100,000	Airbnb cash on cash: -1.2% Traditional cash on cash: 0.02% Airbnb Rental Income: $1681 Traditional Rental Income: $4724 Airbnb ROI: -1.2% Traditional ROI: 0.02%
114 W CHESTNUT Street SAINT MICHAELS, MD Ideally located in the heart of the St. Michaels Historic District, this beautifully maint...	4 beds \| 5 baths \| 3,528 sq.ft.	$1,350,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 1.88% Airbnb Rental Income: $1681 Traditional Rental Income: $4612 Airbnb ROI: -0.83% Traditional ROI: 1.88%
101 MULBERRY Street SAINT MICHAELS, MD Beautifully restored Historic Victorian in the heart of Saint Michaels. This charming home...	4 beds \| 3 baths \| 1,500 sq.ft.	$1,194,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 0.73% Airbnb Rental Income: $1681 Traditional Rental Income: $2590 Airbnb ROI: -0.51% Traditional ROI: 0.73%
114 E CHEW Avenue SAINT MICHAELS, MD The George E. Shockley House (c. 1890) is a rare historic gem in the heart of St. Michaels...	3 beds \| 3 baths \| 2,336 sq.ft.	$1,325,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 0.77% Airbnb Rental Income: $2491 Traditional Rental Income: $3032 Airbnb ROI: -0.16% Traditional ROI: 0.77%
9518 QUAIL HOLLOW unit: 702 SAINT MICHAELS, MD Set within the sought-after Martingham community of Quail Hollow, this fully updated 3-bed...	3 beds \| 3 baths \| 1,800 sq.ft.	$480,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 3.41% Airbnb Rental Income: $2491 Traditional Rental Income: $2728 Airbnb ROI: 1.54% Traditional ROI: 3.41%
204 E MARENGO Street SAINT MICHAELS, MD The perfect weekend getaway does exist - and it's affordable. Escape the city / suburbs an...	2 beds \| 1 baths \| 1,200 sq.ft.	$599,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 2.11% Airbnb Rental Income: $1640 Traditional Rental Income: $2210 Airbnb ROI: 0.27% Traditional ROI: 2.11%
111 GLORIA SAINT MICHAELS, MD Essentially a NEW HOME! Extensively, tastefully and professionally renovated 1965 rancher ...	2 beds \| 2 baths \| 1,125 sq.ft.	$450,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 2.79% Airbnb Rental Income: $1640 Traditional Rental Income: $1890 Airbnb ROI: 1.1% Traditional ROI: 2.79%
9545 QUAIL HOLLOW #205 SAINT MICHAELS, MD Desirable Martingham Community is the location of this fabulous Quail Hollow unit nestled...	2 beds \| 3 baths \| N/A	$385,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 4.91% Airbnb Rental Income: $1640 Traditional Rental Income: $2525 Airbnb ROI: 1.18% Traditional ROI: 4.91%
24390 OAKWOOD PARK Road SAINT MICHAELS, MD Price Improvement! Welcome to your private waterfront retreat just minutes from the charmi...	4 beds \| 4 baths \| 2,839 sq.ft.	$1,825,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 1.02% Airbnb Rental Income: $1681 Traditional Rental Income: $4217 Airbnb ROI: -0.75% Traditional ROI: 1.02%
105 SEYMOUR Avenue SAINT MICHAELS, MD SAINT MICHAELS CHARMING COTTAGE! Welcome Home to this Adorable Cottage perfectly situated ...	2 beds \| 1 baths \| 1,080 sq.ft.	$474,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 2.62% Airbnb Rental Income: $1640 Traditional Rental Income: $1993 Airbnb ROI: 0.78% Traditional ROI: 2.62%
216 E CHEW AVE SAINT MICHAELS, MD Don't miss this rare opportunity. This special home offers spectacular and picturesque vie...	4 beds \| 4 baths \| 3,575 sq.ft.	$1,795,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 0.55% Airbnb Rental Income: $1681 Traditional Rental Income: $3902 Airbnb ROI: -1.06% Traditional ROI: 0.55%
24700 DEEPWATER POINT Drive unit: 1 SAINT MICHAELS, MD Price improvement! Inviting townhouse in the St. Michaels Martingham community with views ...	2 beds \| 3 baths \| 1,486 sq.ft.	$369,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.76% Airbnb Rental Income: $1640 Traditional Rental Income: $1970 Airbnb ROI: 1.47% Traditional ROI: 3.76%
107 W CHESTNUT Street SAINT MICHAELS, MD Your picture-perfect St. Michaels Bungalow on the coveted W. Chestnut Street. The owners c...	3 beds \| 2 baths \| 1,914 sq.ft.	$1,295,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 0.31% Airbnb Rental Income: $2491 Traditional Rental Income: $2117 Airbnb ROI: 0.12% Traditional ROI: 0.31%
107 W CHESTNUT Street SAINT MICHAELS, MD Your picture-perfect St. Michaels Bungalow on the coveted W. Chestnut Street. The owners c...	3 beds \| 2 baths \| 1,914 sq.ft.	$1,295,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 0.31% Airbnb Rental Income: $2491 Traditional Rental Income: $2121 Airbnb ROI: 0.12% Traditional ROI: 0.31%
101 BROOKS Lane SAINT MICHAELS, MD Welcome to this beautifully updated cottage in the heart of St. Michaels-where modern comf...	3 beds \| 2 baths \| 1,120 sq.ft.	$425,000	Airbnb cash on cash: 2.75% Traditional cash on cash: 3.36% Airbnb Rental Income: $2491 Traditional Rental Income: $2132 Airbnb ROI: 2.75% Traditional ROI: 3.36%
1215 WASHINGTON SAINT MICHAELS, MD DESIREABLE RIO VISTA LIVING -MOVE IN ONE SIDE OF THIS DUPLEX AND RENT THE OTHER ONE TO HEL...	4 beds \| 4 baths \| N/A	$525,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 6.27% Airbnb Rental Income: $1681 Traditional Rental Income: $3956 Airbnb ROI: 0.68% Traditional ROI: 6.27%
1211 WASHINGTON SAINT MICHAELS, MD DESIREABLE RIO VISTA LIVING -MOVE IN ONE SIDE OF THIS DUPLEX AND RENT THE OTHER ONE TO HEL...	4 beds \| 4 baths \| N/A	$525,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 5.66% Airbnb Rental Income: $1681 Traditional Rental Income: $3652 Airbnb ROI: 0.69% Traditional ROI: 5.66%
9180 SAINT MICHAELS SAINT MICHAELS, MD UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY...	5 beds \| 5 baths \| N/A	$1,685,000	Airbnb cash on cash: -1.19% Traditional cash on cash: 1.94% Airbnb Rental Income: $457 Traditional Rental Income: $5088 Airbnb ROI: -1.19% Traditional ROI: 1.94%
24645 LONG HAUL SAINT MICHAELS, MD Experience waterfront living at its finest in this remarkable St. Michaels retreat, where ...	4 beds \| 5 baths \| 3,677 sq.ft.	$2,900,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 0.65% Airbnb Rental Income: $1681 Traditional Rental Income: $5714 Airbnb ROI: -1.02% Traditional ROI: 0.65%
222 CHESTNUT SAINT MICHAELS, MD Where the harbor meanders to a close and drifting ducks replace the bustle of boats, this ...	3 beds \| 3 baths \| N/A	$1,885,000	Airbnb cash on cash: -0.7% Traditional cash on cash: -0.18% Airbnb Rental Income: $2491 Traditional Rental Income: $2797 Airbnb ROI: -0.7% Traditional ROI: -0.18%
24965 BACK CREEK Drive SAINT MICHAELS, MD Tucked into the heart of Back Creek Landing, this home offers the kind of layout and setti...	3 beds \| 3 baths \| 2,798 sq.ft.	$739,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 2.6% Airbnb Rental Income: $2491 Traditional Rental Income: $3132 Airbnb ROI: 0.79% Traditional ROI: 2.6%
7865 PEA NECK SAINT MICHAELS, MD Under construction by Laine Street Homes, this exceptional property offers over 3,300 sq f...	4 beds \| 4 baths \| 3,332 sq.ft.	$1,379,800	Airbnb cash on cash: -0.21% Traditional cash on cash: 1.73% Airbnb Rental Income: $1681 Traditional Rental Income: $3703 Airbnb ROI: -0.21% Traditional ROI: 1.73%

Real Estate investment in Saint-michaels, MD

There are 29 properties for sale in the city of Saint Michaels . The median list price in Saint Michaels is $795,000 and the average price per square foot is $329. In April 2026, the average monthly cash on cash return in Saint Michaels is 1.00%. The average monthly rental income in Saint Michaels is $2,287.

Saint-michaels, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 29 investment properties available for sale in Saint-michaels.

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

The ROI for Short-Term is higher than the Long-Term in Saint-michaels with average rental income of $1,681.

Your search for investment property begins and ends here

Investment Property for Sale in Saint Michaels, MD

408 SPINNAKER LN

SAINT MICHAELS, MD

4 beds | 3 baths | N/A

$699,000

Airbnb cash on cash: -0.29%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $1681

Traditional Rental Income: $3037

Airbnb ROI: -0.29%

Traditional ROI: 2.51%

106 CHESTNUT Street E

SAINT MICHAELS, MD

2 beds | 3 baths | 2,282 sq.ft.

$1,325,000

Airbnb cash on cash: -0.66%

Traditional cash on cash: 0.72%

Airbnb Rental Income: $1640

Traditional Rental Income: $2879

Airbnb ROI: -0.66%

Traditional ROI: 0.72%

938 MAREA TERRACE

SAINT MICHAELS, MD

4 beds | 6 baths | 3,000 sq.ft.

$2,390,000

Airbnb cash on cash: -1.02%

Traditional cash on cash: 1.73%

Airbnb Rental Income: $1681

Traditional Rental Income: $7308

Airbnb ROI: -1.02%

Traditional ROI: 1.73%

24912 BACK CREEK Drive

SAINT MICHAELS, MD

3 beds | 3 baths | 3,166 sq.ft.

$795,000

Airbnb cash on cash: 0.61%

Traditional cash on cash: 0.99%

Airbnb Rental Income: $2491

Traditional Rental Income: $2170

Airbnb ROI: 0.61%

Traditional ROI: 0.99%

23961 LYNNEWOOD Drive

SAINT MICHAELS, MD

4 beds | 4 baths | 4,035 sq.ft.

$3,100,000

Airbnb cash on cash: -1.2%

Traditional cash on cash: 0.02%

Airbnb Rental Income: $1681

Traditional Rental Income: $4724

Airbnb ROI: -1.2%

Traditional ROI: 0.02%

114 W CHESTNUT Street

SAINT MICHAELS, MD

4 beds | 5 baths | 3,528 sq.ft.

$1,350,000

Airbnb cash on cash: -0.83%

Traditional cash on cash: 1.88%

Airbnb Rental Income: $1681

Traditional Rental Income: $4612

Airbnb ROI: -0.83%

Traditional ROI: 1.88%

101 MULBERRY Street

SAINT MICHAELS, MD

4 beds | 3 baths | 1,500 sq.ft.

$1,194,000

Airbnb cash on cash: -0.51%

Traditional cash on cash: 0.73%

Airbnb Rental Income: $1681

Traditional Rental Income: $2590

Airbnb ROI: -0.51%

Traditional ROI: 0.73%

114 E CHEW Avenue

SAINT MICHAELS, MD

3 beds | 3 baths | 2,336 sq.ft.

$1,325,000

Airbnb cash on cash: -0.16%

Traditional cash on cash: 0.77%

Airbnb Rental Income: $2491

Traditional Rental Income: $3032

Airbnb ROI: -0.16%