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	$725,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 2.39% Airbnb Rental Income: $1681 Traditional Rental Income: $3037 Airbnb ROI: -0.31% Traditional ROI: 2.39%
24912 BACK CREEK Drive SAINT MICHAELS, MD Welcome to Back Creek Landing - one of Saint Michaels' most desirable neighborhoods, k...	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%
24318 OAKWOOD PARK Road SAINT MICHAELS, MD Welcome to Old House Cove Waterfront Retreat in St. Michaels, MD Nestled on nearly half an...	3 beds \| 3 baths \| 2,085 sq.ft.	$1,195,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 0.71% Airbnb Rental Income: $2491 Traditional Rental Income: $2478 Airbnb ROI: 0.18% Traditional ROI: 0.71%
24749 SWAN Road SAINT MICHAELS, MD Special Year-End Incentive! Seller is offering a Buyer Credit at settlement toward closing...	3 beds \| 3 baths \| 2,496 sq.ft.	$630,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 3.29% Airbnb Rental Income: $2491 Traditional Rental Income: $2952 Airbnb ROI: 1.48% Traditional ROI: 3.29%
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.	$349,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 5.94% Airbnb Rental Income: $1640 Traditional Rental Income: $2624 Airbnb ROI: 1.52% Traditional ROI: 5.94%
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.	$1,195,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 0.47% Airbnb Rental Income: $1640 Traditional Rental Income: $2301 Airbnb ROI: -0.54% Traditional ROI: 0.47%
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.	$549,900	Airbnb cash on cash: 1.86% Traditional cash on cash: 3.77% Airbnb Rental Income: $2491 Traditional Rental Income: $2873 Airbnb ROI: 1.86% Traditional ROI: 3.77%
207 DODSON Avenue SAINT MICHAELS, MD Fabulous 1910 Bungalow with welcoming front porch that has been renovated throughout. All ...	2 beds \| 2 baths \| 960 sq.ft.	$499,900	Airbnb cash on cash: 0.93% Traditional cash on cash: 3.31% Airbnb Rental Income: $1640 Traditional Rental Income: $2292 Airbnb ROI: 0.93% Traditional ROI: 3.31%
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%
807 RADCLIFF AVE SAINT MICHAELS, MD Home is currently under construction with an estimated completion date of Feb-March 2026. ...	3 beds \| 3 baths \| N/A	$859,900	Airbnb cash on cash: 0.61% Traditional cash on cash: 1.53% Airbnb Rental Income: $2491 Traditional Rental Income: $2629 Airbnb ROI: 0.61% Traditional ROI: 1.53%
24390 OAKWOOD PARK Road SAINT MICHAELS, MD Welcome to your private waterfront retreat just minutes from the charming, historic town o...	4 beds \| 4 baths \| 2,839 sq.ft.	$1,900,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 0.97% Airbnb Rental Income: $1681 Traditional Rental Income: $4217 Airbnb ROI: -0.73% Traditional ROI: 0.97%
105 SEYMOUR Avenue SAINT MICHAELS, MD SAINT MICHAELS CHARMER! Welcome Home to this Cozy Cottage perfectly situated in the desira...	2 beds \| 1 baths \| 1,080 sq.ft.	$499,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 2.44% Airbnb Rental Income: $1640 Traditional Rental Income: $1993 Airbnb ROI: 0.69% Traditional ROI: 2.44%
100 GRACE Street SAINT MICHAELS, MD Located in the heart of St. Michaels' historic district, this adorable cottage has a rare ...	2 beds \| 3 baths \| 1,445 sq.ft.	$1,099,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 0.95% Airbnb Rental Income: $1640 Traditional Rental Income: $2619 Airbnb ROI: -0.46% Traditional ROI: 0.95%

Real Estate investment in Saint-michaels, MD

There are 14 properties for sale in the city of Saint Michaels . The median list price in Saint Michaels is $760,000 and the average price per square foot is $351. In December 2025, the average monthly cash on cash return in Saint Michaels is 1.00%. The average monthly rental income in Saint Michaels is $2,348.

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

There are 14 investment properties available for sale in Saint-michaels.

In 2025, 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 $1,640.

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

$725,000

Airbnb cash on cash: -0.31%

Traditional cash on cash: 2.39%

Airbnb Rental Income: $1681

Traditional Rental Income: $3037

Airbnb ROI: -0.31%

Traditional ROI: 2.39%

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%

24318 OAKWOOD PARK Road

SAINT MICHAELS, MD

3 beds | 3 baths | 2,085 sq.ft.

$1,195,000

Airbnb cash on cash: 0.18%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $2491

Traditional Rental Income: $2478

Airbnb ROI: 0.18%

Traditional ROI: 0.71%

24749 SWAN Road

SAINT MICHAELS, MD

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

$630,000

Airbnb cash on cash: 1.48%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $2491

Traditional Rental Income: $2952

Airbnb ROI: 1.48%

Traditional ROI: 3.29%

24362 WIDGEON Place unit: 4 #4

SAINT MICHAELS, MD

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

$349,000

Airbnb cash on cash: 1.52%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $1640

Traditional Rental Income: $2624

Airbnb ROI: 1.52%

Traditional ROI: 5.94%

107 E CHESTNUT Street E

SAINT MICHAELS, MD

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

$1,195,000

Airbnb cash on cash: -0.54%

Traditional cash on cash: 0.47%

Airbnb Rental Income: $1640

Traditional Rental Income: $2301

Airbnb ROI: -0.54%

Traditional ROI: 0.47%

228 TYLER Avenue

SAINT MICHAELS, MD

3 beds | 3 baths | 1,922 sq.ft.

$549,900

Airbnb cash on cash: 1.86%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $2491

Traditional Rental Income: $2873

Airbnb ROI: 1.86%