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	$699,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 2.51% Airbnb Rental Income: $2813 Traditional Rental Income: $3037 Airbnb ROI: 1.16% Traditional ROI: 2.51%
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.	$2,249,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 1.9% Airbnb Rental Income: $2813 Traditional Rental Income: $7308 Airbnb ROI: -0.57% Traditional ROI: 1.9%
24830 DEEPWATER POINT DR SAINT MICHAELS, MD DREAMING OF A BEACH HOUSE ? STUNNING LOCATION , ENDLESS BREEZES AND SUNSETS..... A treasu...	3 beds \| 3 baths \| N/A	$2,425,000	Airbnb cash on cash: -0.24% Traditional cash on cash: -0.03% Airbnb Rental Income: $3257 Traditional Rental Income: $3017 Airbnb ROI: -0.24% Traditional ROI: -0.03%
9206 MARTINGHAM Drive SAINT MICHAELS, MD Improved pricing - now offered at $725,000. A light-filled entertainer's dream with soarin...	4 beds \| 3 baths \| 2,841 sq.ft.	$725,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 3.14% Airbnb Rental Income: $2813 Traditional Rental Income: $3306 Airbnb ROI: 1.44% Traditional ROI: 3.14%
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: -0.87% Traditional cash on cash: 0.02% Airbnb Rental Income: $2813 Traditional Rental Income: $4724 Airbnb ROI: -0.87% Traditional ROI: 0.02%
114 W CHESTNUT Street SAINT MICHAELS, MD Enjoy historic in-town living in the heart of St. Michaels, where this beautifully maintai...	4 beds \| 5 baths \| 3,528 sq.ft.	$1,350,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 1.88% Airbnb Rental Income: $2813 Traditional Rental Income: $4612 Airbnb ROI: -0.08% Traditional ROI: 1.88%
203 CHEW Avenue E SAINT MICHAELS, MD Welcome to 203 E Chew Avenue, a residence of exceptional craftsmanship and refined luxury,...	5 beds \| 6 baths \| 4,673 sq.ft.	$2,538,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 0.22% Airbnb Rental Income: $2058 Traditional Rental Income: $4722 Airbnb ROI: -1.14% Traditional ROI: 0.22%
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: 0.34% Traditional cash on cash: 0.73% Airbnb Rental Income: $2813 Traditional Rental Income: $2590 Airbnb ROI: 0.34% Traditional ROI: 0.73%
9518 QUAIL HOLLOW #702 SAINT MICHAELS, MD Set within the sought-after Martingham community of Quail Hollow, backing to the top rated...	3 beds \| 3 baths \| 1,800 sq.ft.	$480,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 3.41% Airbnb Rental Income: $3257 Traditional Rental Income: $2728 Airbnb ROI: 2.96% 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: 0.75% Traditional cash on cash: 2.11% Airbnb Rental Income: $1965 Traditional Rental Income: $2210 Airbnb ROI: 0.75% Traditional ROI: 2.11%
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: 1.93% Traditional cash on cash: 4.91% Airbnb Rental Income: $1965 Traditional Rental Income: $2525 Airbnb ROI: 1.93% Traditional ROI: 4.91%
807 RADCLIFF AVE SAINT MICHAELS, MD Public OPEN HOUSE Saturday 5/16 from 12-3pm. This BRAND NEW Arts & Crafts home sits on a ...	3 beds \| 3 baths \| N/A	$859,900	Airbnb cash on cash: 1.96% Traditional cash on cash: 2.09% Airbnb Rental Income: $3257 Traditional Rental Income: $2629 Airbnb ROI: 1.96% Traditional ROI: 2.09%
24390 OAKWOOD PARK Road SAINT MICHAELS, MD OPEN HOUSE SUNDAY 5/17 11am to 1pm! Significant price improvement! Welcome to your private...	4 beds \| 4 baths \| 2,839 sq.ft.	$1,679,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 1.19% Airbnb Rental Income: $2813 Traditional Rental Income: $4217 Airbnb ROI: -0.13% Traditional ROI: 1.19%
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: 1.39% Traditional cash on cash: 2.62% Airbnb Rental Income: $1965 Traditional Rental Income: $1993 Airbnb ROI: 1.39% 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: -0.5% Traditional cash on cash: 0.55% Airbnb Rental Income: $2813 Traditional Rental Income: $3902 Airbnb ROI: -0.5% Traditional ROI: 0.55%
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: 4.35% Traditional cash on cash: 3.36% Airbnb Rental Income: $3257 Traditional Rental Income: $2132 Airbnb ROI: 4.35% 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: 2.6% Traditional cash on cash: 5.65% Airbnb Rental Income: $2813 Traditional Rental Income: $3650 Airbnb ROI: 2.6% Traditional ROI: 5.65%
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: 2.61% Traditional cash on cash: 5.66% Airbnb Rental Income: $2813 Traditional Rental Income: $3652 Airbnb ROI: 2.61% 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: -0.34% Traditional cash on cash: 1.94% Airbnb Rental Income: $2058 Traditional Rental Income: $5088 Airbnb ROI: -0.34% 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.	$2,550,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 0.88% Airbnb Rental Income: $2813 Traditional Rental Income: $5714 Airbnb ROI: -0.62% Traditional ROI: 0.88%
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: -0.34% Traditional cash on cash: -0.18% Airbnb Rental Income: $3257 Traditional Rental Income: $2797 Airbnb ROI: -0.34% 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...	4 beds \| 3 baths \| 2,798 sq.ft.	$739,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 2.6% Airbnb Rental Income: $2813 Traditional Rental Income: $3132 Airbnb ROI: 1.18% 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: 0.53% Traditional cash on cash: 1.73% Airbnb Rental Income: $2813 Traditional Rental Income: $3703 Airbnb ROI: 0.53% Traditional ROI: 1.73%
7149 DRUM POINT SAINT MICHAELS, MD ST MICHAELS TUCKED AWAY ON DESIRABLE DRUM POINT NEIGHBORHOOD, MINUTES FROM THE BUZZLING T...	3 beds \| 3 baths \| N/A	$2,249,000	Airbnb cash on cash: -0.39% Traditional cash on cash: -0.19% Airbnb Rental Income: $3257 Traditional Rental Income: $2936 Airbnb ROI: -0.39% Traditional ROI: -0.19%
504 SEYMOUR Avenue SAINT MICHAELS, MD Charming yet completely reimagined, this beautifully remodeled home offers refined Eastern...	3 beds \| 3 baths \| 2,200 sq.ft.	$1,200,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 1.34% Airbnb Rental Income: $3257 Traditional Rental Income: $3049 Airbnb ROI: 0.87% Traditional ROI: 1.34%
204 LINCOLN SAINT MICHAELS, MD RIO VISTA COMMUNITY - NO TOWN TAX - WATER FRONT PARK AT THE MILES RIVER FOR RESIDENTS ONLY...	3 beds \| 2 baths \| N/A	$598,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 2.31% Airbnb Rental Income: $3257 Traditional Rental Income: $2218 Airbnb ROI: 2.86% Traditional ROI: 2.31%
9359 MARTINGHAM SAINT MICHAELS, MD FABULOUS ONE STORY LIVING WITH PRIVATE BACKYARD WITH VIEW OF THE POND OF THE 4TH GREEN O...	4 beds \| 3 baths \| N/A	$795,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 2.63% Airbnb Rental Income: $2813 Traditional Rental Income: $3222 Airbnb ROI: 1.19% Traditional ROI: 2.63%
24561 DEEPWATER POINT SAINT MICHAELS, MD Effortless living in the Martingham community. This thoughtfully designed 3-bedroom, 3-bat...	3 beds \| 3 baths \| 2,144 sq.ft.	$649,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 2.85% Airbnb Rental Income: $3257 Traditional Rental Income: $2891 Airbnb ROI: 2.25% Traditional ROI: 2.85%
203 CANTON Street SAINT MICHAELS, MD Discover this ranch-style home located 1 block to the center of downtown, perfect for thos...	3 beds \| 2 baths \| 1,364 sq.ft.	$350,000	Airbnb cash on cash: 5.69% Traditional cash on cash: 4.99% Airbnb Rental Income: $3257 Traditional Rental Income: $2293 Airbnb ROI: 5.69% Traditional ROI: 4.99%
24555 DEEPWATER POINT SAINT MICHAELS, MD This sturdy brick ranch sits on a premium lot backing up to The Links at Perry Cabin Golf ...	4 beds \| 3 baths \| 2,072 sq.ft.	$779,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 2.46% Airbnb Rental Income: $2813 Traditional Rental Income: $2957 Airbnb ROI: 1.35% Traditional ROI: 2.46%

Real Estate investment in Saint-michaels, MD

There are 30 properties for sale in the city of Saint Michaels . The median list price in Saint Michaels is $827,450 and the average price per square foot is $322. In May 2026, the average monthly cash on cash return in Saint Michaels is 1.00%. The average monthly rental income in Saint Michaels is $2,525.

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

There are 30 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 $2,813.

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: 1.16%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $2813

Traditional Rental Income: $3037

Airbnb ROI: 1.16%

Traditional ROI: 2.51%

938 MAREA TERRACE

SAINT MICHAELS, MD

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

$2,249,000

Airbnb cash on cash: -0.57%

Traditional cash on cash: 1.9%

Airbnb Rental Income: $2813

Traditional Rental Income: $7308

Airbnb ROI: -0.57%

Traditional ROI: 1.9%

24830 DEEPWATER POINT DR

SAINT MICHAELS, MD

3 beds | 3 baths | N/A

$2,425,000

Airbnb cash on cash: -0.24%

Traditional cash on cash: -0.03%

Airbnb Rental Income: $3257

Traditional Rental Income: $3017

Airbnb ROI: -0.24%

Traditional ROI: -0.03%

9206 MARTINGHAM Drive

SAINT MICHAELS, MD

4 beds | 3 baths | 2,841 sq.ft.

$725,000

Airbnb cash on cash: 1.44%

Traditional cash on cash: 3.14%

Airbnb Rental Income: $2813

Traditional Rental Income: $3306

Airbnb ROI: 1.44%

Traditional ROI: 3.14%

23961 LYNNEWOOD Drive

SAINT MICHAELS, MD

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

$3,100,000

Airbnb cash on cash: -0.87%

Traditional cash on cash: 0.02%

Airbnb Rental Income: $2813

Traditional Rental Income: $4724

Airbnb ROI: -0.87%

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: -0.08%

Traditional cash on cash: 1.88%

Airbnb Rental Income: $2813

Traditional Rental Income: $4612

Airbnb ROI: -0.08%

Traditional ROI: 1.88%

203 CHEW Avenue E

SAINT MICHAELS, MD

5 beds | 6 baths | 4,673 sq.ft.

$2,538,000

Airbnb cash on cash: -1.14%

Traditional cash on cash: 0.22%

Airbnb Rental Income: $2058

Traditional Rental Income: $4722

Airbnb ROI: -1.14%

Traditional ROI: 0.22%

101 MULBERRY Street

SAINT MICHAELS, MD

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

$1,194,000

Airbnb cash on cash: 0.34%

Traditional cash on cash: 0.73%

Airbnb Rental Income: $2813

Traditional Rental Income: $2590

Airbnb ROI: 0.34%