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 This immaculate 4 bedroom, 2.5 bath home was built in 2022 and has been thoughtfully enhan...	4 beds \| 3 baths \| N/A	$775,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 2.17% Airbnb Rental Income: $2532 Traditional Rental Income: $3037 Airbnb ROI: 0.62% Traditional ROI: 2.17%
106 GRACE Street SAINT MICHAELS, MD Grace and Gratitude perfectly describe this charming historic home on Grace Street in the ...	3 beds \| 2 baths \| 2,068 sq.ft.	$780,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 1.68% Airbnb Rental Income: $3122 Traditional Rental Income: $2654 Airbnb ROI: 1.35% Traditional ROI: 1.68%
25070 HURLEY LN SAINT MICHAELS, MD HUGE PRICE DROP in St. MIchaels! This gorgeous home just became an unbeatable deal in one ...	3 beds \| 3 baths \| N/A	$439,999	Airbnb cash on cash: 4.07% Traditional cash on cash: 4.6% Airbnb Rental Income: $3122 Traditional Rental Income: $2632 Airbnb ROI: 4.07% Traditional ROI: 4.6%
24749 SWAN Road SAINT MICHAELS, MD Located in Martingham, home of the newly redesigned Pete Dye golf course, The Links at Per...	3 beds \| 3 baths \| 2,496 sq.ft.	$650,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 3.16% Airbnb Rental Income: $3122 Traditional Rental Income: $2952 Airbnb ROI: 2.27% Traditional ROI: 3.16%
24312 OAKWOOD PARK SAINT MICHAELS, MD Dappled in shade along the tranquil shores of San Domingo Creek, this picturesque Oakwood ...	2 beds \| 1 baths \| N/A	$825,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 0.61% Airbnb Rental Income: $2129 Traditional Rental Income: $1635 Airbnb ROI: 0.54% Traditional ROI: 0.61%
9539 QUAIL HOLLOW unit: 303 #303 SAINT MICHAELS, MD Located in the desirable Martingham Quail Hollow Community and nestled alongside the prest...	2 beds \| 3 baths \| 1,800 sq.ft.	$379,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 6.03% Airbnb Rental Income: $2129 Traditional Rental Income: $2889 Airbnb ROI: 2.36% Traditional ROI: 6.03%
24362 WIDGEON Place unit: 4 #4 SAINT MICHAELS, MD Welcome to Martingham, a premier golf course and waterfront community located just a mile ...	2 beds \| 3 baths \| 1,800 sq.ft.	$353,900	Airbnb cash on cash: 2.72% Traditional cash on cash: 5.84% Airbnb Rental Income: $2129 Traditional Rental Income: $2624 Airbnb ROI: 2.72% Traditional ROI: 5.84%
107 E CHESTNUT Street E SAINT MICHAELS, MD St. Michaels charm in this Circa 1870 Certified Plaque home, although historical data refl...	2 beds \| 2 baths \| 2,024 sq.ft.	$1,295,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 0.36% Airbnb Rental Income: $2129 Traditional Rental Income: $2301 Airbnb ROI: -0.23% Traditional ROI: 0.36%
228 TYLER Avenue SAINT MICHAELS, MD This handsome home is nestled in the trees on a quiet cul de sac in Rio Vista. This popula...	3 beds \| 3 baths \| 1,922 sq.ft.	$585,000	Airbnb cash on cash: 2.65% Traditional cash on cash: 3.49% Airbnb Rental Income: $3122 Traditional Rental Income: $2873 Airbnb ROI: 2.65% Traditional ROI: 3.49%
23869 NEW LAND Drive SAINT MICHAELS, MD Welcome to Heron Cove Farm, a beautiful waterfront paradise situated on the banks of Broad...	3 beds \| 2 baths \| 2,717 sq.ft.	$1,850,000	Airbnb cash on cash: -0.73% Traditional cash on cash: -0.3% Airbnb Rental Income: $3122 Traditional Rental Income: $3154 Airbnb ROI: -0.73% Traditional ROI: -0.3%
207 DODSON SAINT MICHAELS, MD Fabulous 1910 Bungalow with welcoming front porch that has been renovated throughout. All ...	2 beds \| 2 baths \| 960 sq.ft.	$524,900	Airbnb cash on cash: 1.67% Traditional cash on cash: 3.11% Airbnb Rental Income: $2129 Traditional Rental Income: $2292 Airbnb ROI: 1.67% Traditional ROI: 3.11%
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: 2.31% Traditional cash on cash: 4.91% Airbnb Rental Income: $2129 Traditional Rental Income: $2525 Airbnb ROI: 2.31% Traditional ROI: 4.91%

Real Estate investment in Saint-michaels, MD

There are 12 properties for sale in the city of Saint Michaels . The median list price in Saint Michaels is $617,500 and the average price per square foot is $313. In October 2025, the average monthly cash on cash return in Saint Michaels is 3.00%. The average monthly rental income in Saint Michaels is $2,632.

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

There are 12 investment properties available for sale in Saint-michaels.

In 2025, the best neighborhood to buy investment property is SAINT MICHAELS.

The ROI for Long-Term is higher than the Short-Term in Saint-michaels with average rental income of $2,632.

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

$775,000

Airbnb cash on cash: 0.62%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $2532

Traditional Rental Income: $3037

Airbnb ROI: 0.62%

Traditional ROI: 2.17%

106 GRACE Street

SAINT MICHAELS, MD

3 beds | 2 baths | 2,068 sq.ft.

$780,000

Airbnb cash on cash: 1.35%

Traditional cash on cash: 1.68%

Airbnb Rental Income: $3122

Traditional Rental Income: $2654

Airbnb ROI: 1.35%

Traditional ROI: 1.68%

25070 HURLEY LN

SAINT MICHAELS, MD

3 beds | 3 baths | N/A

$439,999

Airbnb cash on cash: 4.07%

Traditional cash on cash: 4.6%

Airbnb Rental Income: $3122

Traditional Rental Income: $2632

Airbnb ROI: 4.07%

Traditional ROI: 4.6%

24749 SWAN Road

SAINT MICHAELS, MD

3 beds | 3 baths | 2,496 sq.ft.

$650,000

Airbnb cash on cash: 2.27%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $3122

Traditional Rental Income: $2952

Airbnb ROI: 2.27%

Traditional ROI: 3.16%

24312 OAKWOOD PARK

SAINT MICHAELS, MD

2 beds | 1 baths | N/A

$825,000

Airbnb cash on cash: 0.54%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $2129

Traditional Rental Income: $1635

Airbnb ROI: 0.54%

Traditional ROI: 0.61%

9539 QUAIL HOLLOW unit: 303 #303

SAINT MICHAELS, MD

2 beds | 3 baths | 1,800 sq.ft.

$379,000

Airbnb cash on cash: 2.36%

Traditional cash on cash: 6.03%

Airbnb Rental Income: $2129

Traditional Rental Income: $2889

Airbnb ROI: 2.36%

Traditional ROI: 6.03%

24362 WIDGEON Place unit: 4 #4

SAINT MICHAELS, MD

2 beds | 3 baths | 1,800 sq.ft.

$353,900

Airbnb cash on cash: 2.72%

Traditional cash on cash: 5.84%

Airbnb Rental Income: $2129

Traditional Rental Income: $2624

Airbnb ROI: 2.72%

Traditional ROI: 5.84%

107 E CHESTNUT Street E

SAINT MICHAELS, MD

2 beds | 2 baths | 2,024 sq.ft.

$1,295,000

Airbnb cash on cash: -0.23%

Traditional cash on cash: 0.36%

Airbnb Rental Income: $2129

Traditional Rental Income: $2301

Airbnb ROI: -0.23%