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.

Single Family Homes for Sale in Saint Michaels, MD

Search for Single Family Residential for Sale in Saint Michaels, 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 31 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
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.	$699,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 2.51% Airbnb Rental Income: $2210 Traditional Rental Income: $3037 Airbnb ROI: 0.39% Traditional ROI: 2.51%
106 Chestnut St E SAINT MICHAELS, MD Luxury Restoration in the Heart of Historic St. Michaels Welcome to 106 E. Chestnut Street...	2 beds \| 2 baths \| 2,282 sq.ft.	$1,325,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 0.72% Airbnb Rental Income: $2063 Traditional Rental Income: $2879 Airbnb ROI: -0.38% Traditional ROI: 0.72%
938 Marea Ter SAINT MICHAELS, MD Fabulous in-town St. Michaels waterfront property - This coastal style waterfront residenc...	4 beds \| 5 baths \| 3,000 sq.ft.	$2,390,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 1.73% Airbnb Rental Income: $2210 Traditional Rental Income: $7308 Airbnb ROI: -0.82% Traditional ROI: 1.73%
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: 1.49% Traditional cash on cash: 0.99% Airbnb Rental Income: $3281 Traditional Rental Income: $2170 Airbnb ROI: 1.49% Traditional ROI: 0.99%
9206 Martingham Dr SAINT MICHAELS, MD Beautiful four-bedroom contemporary home on a private one + acre lot overlooking the 12th ...	4 beds \| 2 baths \| 2,841 sq.ft.	$749,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 3.01% Airbnb Rental Income: $2210 Traditional Rental Income: $3306 Airbnb ROI: 0.65% Traditional ROI: 3.01%
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: -1.05% Traditional cash on cash: 0.02% Airbnb Rental Income: $2210 Traditional Rental Income: $4724 Airbnb ROI: -1.05% Traditional ROI: 0.02%
114 W Chestnut St SAINT MICHAELS, MD Ideally located in the heart of the St. Michaels Historic District, this beautifully maint...	4 beds \| 4 baths \| 3,528 sq.ft.	$1,350,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 1.88% Airbnb Rental Income: $2210 Traditional Rental Income: $4612 Airbnb ROI: -0.48% Traditional ROI: 1.88%
203 Chew Ave E SAINT MICHAELS, MD Welcome to 203 E Chew Avenue, a residence of exceptional craftsmanship and refined luxury,...	4 beds \| 3 baths \| 4,673 sq.ft.	$2,538,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 0.22% Airbnb Rental Income: $2210 Traditional Rental Income: $4722 Airbnb ROI: -1.09% Traditional ROI: 0.22%
101 Mulberry St SAINT MICHAELS, MD Beautifully restored Historic Victorian in the heart of Saint Michaels. This charming home...	4 beds \| 2 baths \| 1,500 sq.ft.	$1,194,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 0.73% Airbnb Rental Income: $2210 Traditional Rental Income: $2590 Airbnb ROI: -0.11% Traditional ROI: 0.73%
114 E Chew Ave SAINT MICHAELS, MD The George E. Shockley House (c. 1890) is a rare historic gem in the heart of St. Michaels...	3 beds \| 2 baths \| 2,336 sq.ft.	$1,250,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 0.77% Airbnb Rental Income: $3281 Traditional Rental Income: $3032 Airbnb ROI: 0.37% Traditional ROI: 0.77%
204 E Marengo St 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: 0.9% Traditional cash on cash: 2.11% Airbnb Rental Income: $2063 Traditional Rental Income: $2210 Airbnb ROI: 0.9% Traditional ROI: 2.11%
111 Gloria SAINT MICHAELS, MD Essentially a NEW HOME! Extensively, tastefully and professionally renovated 1965 rancher ...	2 beds \| 1 baths \| 1,125 sq.ft.	$435,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 2.79% Airbnb Rental Income: $2063 Traditional Rental Income: $1890 Airbnb ROI: 1.94% Traditional ROI: 2.79%
24390 Oakwood Park Rd SAINT MICHAELS, MD Price Improvement! Welcome to your private waterfront retreat just minutes from the charmi...	4 beds \| 3 baths \| 2,839 sq.ft.	$1,825,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 1.02% Airbnb Rental Income: $2210 Traditional Rental Income: $4217 Airbnb ROI: -0.49% Traditional ROI: 1.02%
105 Seymour Ave 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: 1.58% Traditional cash on cash: 2.62% Airbnb Rental Income: $2063 Traditional Rental Income: $1993 Airbnb ROI: 1.58% 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...	N/A beds \| 1 baths \| 3,575 sq.ft.	$1,795,000	Airbnb cash on cash: -0.8% Traditional cash on cash: 0.55% Airbnb Rental Income: $2210 Traditional Rental Income: $3902 Airbnb ROI: -0.8% Traditional ROI: 0.55%
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.	$1,225,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 0.31% Airbnb Rental Income: $3281 Traditional Rental Income: $2121 Airbnb ROI: 0.66% Traditional ROI: 0.31%
101 Brooks Ln 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: 4.4% Traditional cash on cash: 3.36% Airbnb Rental Income: $3281 Traditional Rental Income: $2132 Airbnb ROI: 4.4% Traditional ROI: 3.36%
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 \| 4,728 sq.ft.	$1,685,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 1.94% Airbnb Rental Income: $1600 Traditional Rental Income: $5088 Airbnb ROI: -0.58% Traditional ROI: 1.94%
24645 Long Haul SAINT MICHAELS, MD Experience waterfront living at its finest in this remarkable St. Michaels retreat, where ...	N/A beds \| N/A baths \| 3,677 sq.ft.	$2,750,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 0.74% Airbnb Rental Income: $2210 Traditional Rental Income: $5714 Airbnb ROI: -0.85% Traditional ROI: 0.74%
222 Chestnut SAINT MICHAELS, MD Where the harbor meanders to a close and drifting ducks replace the bustle of boats, this ...	3 beds \| 2 baths \| 2,284 sq.ft.	$1,885,000	Airbnb cash on cash: -0.32% Traditional cash on cash: -0.18% Airbnb Rental Income: $3281 Traditional Rental Income: $2797 Airbnb ROI: -0.32% Traditional ROI: -0.18%
24965 Back Creek Dr SAINT MICHAELS, MD Tucked into the heart of Back Creek Landing, this home offers the kind of layout and setti...	3 beds \| 2 baths \| 2,798 sq.ft.	$739,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 2.6% Airbnb Rental Income: $3281 Traditional Rental Income: $3132 Airbnb ROI: 1.75% Traditional ROI: 2.6%
7865 Pea Nck SAINT MICHAELS, MD Under construction by Laine Street Homes, this exceptional property offers over 3,300 sq f...	4 beds \| 3 baths \| 3,332 sq.ft.	$1,379,800	Airbnb cash on cash: 0.13% Traditional cash on cash: 1.73% Airbnb Rental Income: $2210 Traditional Rental Income: $3703 Airbnb ROI: 0.13% Traditional ROI: 1.73%
7149 Drum Pt SAINT MICHAELS, MD ST MICHAELS TUCKED AWAY ON DESIRABLE DRUM POINT NEIGHBORHOOD, MINUTES FROM THE BUZZLING T...	3 beds \| 3 baths \| 3,017 sq.ft.	$2,249,000	Airbnb cash on cash: -0.38% Traditional cash on cash: -0.19% Airbnb Rental Income: $3281 Traditional Rental Income: $2936 Airbnb ROI: -0.38% Traditional ROI: -0.19%

Your search for investment property begins and ends here

Single Family Homes for Sale in Saint Michaels, MD

408 Spinnaker Ln

SAINT MICHAELS, MD

4 beds | 2 baths | 1,957 sq.ft.

$699,000

Airbnb cash on cash: 0.39%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $2210

Traditional Rental Income: $3037

Airbnb ROI: 0.39%

Traditional ROI: 2.51%

106 Chestnut St E

SAINT MICHAELS, MD

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

$1,325,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 0.72%

Airbnb Rental Income: $2063

Traditional Rental Income: $2879

Airbnb ROI: -0.38%

Traditional ROI: 0.72%

938 Marea Ter

SAINT MICHAELS, MD

4 beds | 5 baths | 3,000 sq.ft.

$2,390,000

Airbnb cash on cash: -0.82%

Traditional cash on cash: 1.73%

Airbnb Rental Income: $2210

Traditional Rental Income: $7308

Airbnb ROI: -0.82%

Traditional ROI: 1.73%

24912 Back Creek Dr

SAINT MICHAELS, MD

3 beds | 2 baths | 3,166 sq.ft.

$795,000

Airbnb cash on cash: 1.49%

Traditional cash on cash: 0.99%

Airbnb Rental Income: $3281

Traditional Rental Income: $2170

Airbnb ROI: 1.49%

Traditional ROI: 0.99%

9206 Martingham Dr

SAINT MICHAELS, MD

4 beds | 2 baths | 2,841 sq.ft.

$749,000

Airbnb cash on cash: 0.65%

Traditional cash on cash: 3.01%

Airbnb Rental Income: $2210

Traditional Rental Income: $3306

Airbnb ROI: 0.65%

Traditional ROI: 3.01%

23961 Lynnewood Dr

SAINT MICHAELS, MD

4 beds | 3 baths | 4,035 sq.ft.

$3,100,000

Airbnb cash on cash: -1.05%

Traditional cash on cash: 0.02%

Airbnb Rental Income: $2210

Traditional Rental Income: $4724

Airbnb ROI: -1.05%

Traditional ROI: 0.02%

114 W Chestnut St

SAINT MICHAELS, MD

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

$1,350,000

Airbnb cash on cash: -0.48%

Traditional cash on cash: 1.88%

Airbnb Rental Income: $2210

Traditional Rental Income: $4612

Airbnb ROI: -0.48%

Traditional ROI: 1.88%

203 Chew Ave E

SAINT MICHAELS, MD

4 beds | 3 baths | 4,673 sq.ft.

$2,538,000

Airbnb cash on cash: -1.09%

Traditional cash on cash: 0.22%

Airbnb Rental Income: $2210

Traditional Rental Income: $4722

Airbnb ROI: -1.09%