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 \| 2 baths \| 1,957 sq.ft.	$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%
24700 Deepwater Point Dr #1 SAINT MICHAELS, MD Spectacular Golf Course Views! End of Group THS in Martingham Boasts 2 Master Suites, Rear...	2 beds \| 2 baths \| 1,486 sq.ft.	$389,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 2.76% Airbnb Rental Income: $1640 Traditional Rental Income: $1823 Airbnb ROI: 0.99% Traditional ROI: 2.76%
24912 Back Creek Dr SAINT MICHAELS, MD Back Creek Landing home for sale in St. Michaels, MD - located in one of the town's most d...	3 beds \| 2 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 Dr SAINT MICHAELS, MD Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends ...	4 beds \| 3 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%
24977 Back Creek Dr SAINT MICHAELS, MD Custom Built Home ! All Extras included in this one. Many Built ins and extras throughout....	4 beds \| 3 baths \| 3,010 sq.ft.	$749,999	Airbnb cash on cash: -0.01% Traditional cash on cash: 2.06% Airbnb Rental Income: $1681 Traditional Rental Income: $2656 Airbnb ROI: -0.01% Traditional ROI: 2.06%
24749 Swan Rd SAINT MICHAELS, MD This is a rare chance to secure meaningful savings and a beautiful home in one of the East...	3 beds \| 2 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%
228 Tyler Ave SAINT MICHAELS, MD This handsome home is nestled in the trees on a quiet cul de sac in Rio Vista. This popula...	3 beds \| 2 baths \| 1,922 sq.ft.	$549,900	Airbnb cash on cash: 1.86% Traditional cash on cash: 3.78% Airbnb Rental Income: $2491 Traditional Rental Income: $2873 Airbnb ROI: 1.86% Traditional ROI: 3.78%
24390 Oakwood Park Rd SAINT MICHAELS, MD Welcome to your private waterfront retreat just minutes from the charming, historic town o...	4 beds \| 3 baths \| 2,839 sq.ft.	$1,900,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 0.94% Airbnb Rental Income: $1681 Traditional Rental Income: $4217 Airbnb ROI: -0.76% Traditional ROI: 0.94%
216 E Chew Ave SAINT MICHAELS, MD Don't miss this rare opportunity. This special home offers spectacular and picturesque vie...	4 beds \| 3 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 #1 SAINT MICHAELS, MD Inviting townhouse in the St. Michaels Martingham community with views across the Links at...	2 beds \| 3 baths \| 1,486 sq.ft.	$389,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 4.68% Airbnb Rental Income: $1640 Traditional Rental Income: $2393 Airbnb ROI: 1.35% Traditional ROI: 4.68%
912 Calvert Ave SAINT MICHAELS, MD 912 Calvert Ave, SAINT MICHAELS, MD 21663 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$229,000	Airbnb cash on cash: 2.37% Traditional cash on cash: 1.85% Airbnb Rental Income: $1495 Traditional Rental Income: $943 Airbnb ROI: 2.37% Traditional ROI: 1.85%
107 W Chestnut St 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.	$1,350,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 0.21% Airbnb Rental Income: $2491 Traditional Rental Income: $2061 Airbnb ROI: 0.07% Traditional ROI: 0.21%
209 Webb Ln SAINT MICHAELS, MD Wonderful opportunity to live in the quaint, picturesque and historic town of St Michaels ...	2 beds \| 1 baths \| 932 sq.ft.	$229,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 4.64% Airbnb Rental Income: $1640 Traditional Rental Income: $1525 Airbnb ROI: 3.04% Traditional ROI: 4.64%
704 Meadow St SAINT MICHAELS, MD 704 Meadow St, SAINT MICHAELS, MD 21663 \| Single Family Residential	4 beds \| 3 baths \| 3,100 sq.ft.	$889,800	Airbnb cash on cash: -0.73% Traditional cash on cash: 1.09% Airbnb Rental Income: $1681 Traditional Rental Income: $2723 Airbnb ROI: -0.73% Traditional ROI: 1.09%
108 Miles Ave SAINT MICHAELS, MD 108 Miles Ave, SAINT MICHAELS, MD 21663 \| Single Family Residential	3 beds \| 2 baths \| 1,710 sq.ft.	$779,000	Airbnb cash on cash: 0.39% Traditional cash on cash: -0.91% Airbnb Rental Income: $2491 Traditional Rental Income: $943 Airbnb ROI: 0.39% Traditional ROI: -0.91%
8620 Bozman Neavitt SAINT MICHAELS, MD 8620 Bozman Neavitt, SAINT MICHAELS, MD 21663 \| Single Family Residential	6 beds \| 7 baths \| 17,402 sq.ft.	$8,495,000	Airbnb cash on cash: -2.07% Traditional cash on cash: -1.33% Airbnb Rental Income: $457 Traditional Rental Income: $6068 Airbnb ROI: -2.07% Traditional ROI: -1.33%
Lot 16A Meadow St SAINT MICHAELS, MD Lot 16A Meadow St, SAINT MICHAELS, MD 21663 \| Single Family Residential	4 beds \| 2 baths \| N/A	$799,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 0.62% Airbnb Rental Income: $1681 Traditional Rental Income: $2107 Airbnb ROI: -0.58% Traditional ROI: 0.62%

Real Estate investment in Saint-michaels, MD

There are 18 properties for sale in the city of Saint Michaels . The median list price in Saint Michaels is $764,500 and the average price per square foot is $240. In February 2026, the average monthly cash on cash return in Saint Michaels is 1.00%. The average monthly rental income in Saint Michaels is $2,278.

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

There are 18 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 $1,661.

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 | 2 baths | 1,957 sq.ft.

$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%

24700 Deepwater Point Dr #1

SAINT MICHAELS, MD

2 beds | 2 baths | 1,486 sq.ft.

$389,000

Airbnb cash on cash: 0.99%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $1640

Traditional Rental Income: $1823

Airbnb ROI: 0.99%

Traditional ROI: 2.76%

24912 Back Creek Dr

SAINT MICHAELS, MD

3 beds | 2 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 Dr

SAINT MICHAELS, MD

4 beds | 3 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%

24977 Back Creek Dr

SAINT MICHAELS, MD

4 beds | 3 baths | 3,010 sq.ft.

$749,999

Airbnb cash on cash: -0.01%

Traditional cash on cash: 2.06%

Airbnb Rental Income: $1681

Traditional Rental Income: $2656

Airbnb ROI: -0.01%

Traditional ROI: 2.06%

24749 Swan Rd

SAINT MICHAELS, MD

3 beds | 2 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%

228 Tyler Ave

SAINT MICHAELS, MD

3 beds | 2 baths | 1,922 sq.ft.

$549,900

Airbnb cash on cash: 1.86%

Traditional cash on cash: 3.78%

Airbnb Rental Income: $2491

Traditional Rental Income: $2873

Airbnb ROI: 1.86%

Traditional ROI: 3.78%

24390 Oakwood Park Rd

SAINT MICHAELS, MD

4 beds | 3 baths | 2,839 sq.ft.

$1,900,000

Airbnb cash on cash: -0.76%

Traditional cash on cash: 0.94%

Airbnb Rental Income: $1681

Traditional Rental Income: $4217

Airbnb ROI: -0.76%