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: 0.94% Traditional cash on cash: 2.51% Airbnb Rental Income: $2639 Traditional Rental Income: $3037 Airbnb ROI: 0.94% Traditional ROI: 2.51%
24700 Deepwater Point Dr #1 SAINT MICHAELS, MD Price improvement! Inviting townhouse in the St. Michaels Martingham community with views ...	2 beds \| 2 baths \| 1,486 sq.ft.	$369,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 2.74% Airbnb Rental Income: $1965 Traditional Rental Income: $1823 Airbnb ROI: 1.66% Traditional ROI: 2.74%
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.	$2,249,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 1.9% Airbnb Rental Income: $2639 Traditional Rental Income: $7308 Airbnb ROI: -0.64% 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: -0.15% Traditional cash on cash: -0.03% Airbnb Rental Income: $3501 Traditional Rental Income: $3017 Airbnb ROI: -0.15% Traditional ROI: -0.03%
9206 Martingham Dr SAINT MICHAELS, MD Improved pricing on this beautiful four-bedroom contemporary home, now offered at $725,000...	4 beds \| 2 baths \| 2,841 sq.ft.	$725,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 3.14% Airbnb Rental Income: $2639 Traditional Rental Income: $3306 Airbnb ROI: 1.22% Traditional ROI: 3.14%
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: -0.92% Traditional cash on cash: 0.02% Airbnb Rental Income: $2639 Traditional Rental Income: $4724 Airbnb ROI: -0.92% Traditional ROI: 0.02%
114 W Chestnut St SAINT MICHAELS, MD Enjoy historic in-town living in the heart of St. Michaels, where this beautifully maintai...	4 beds \| 4 baths \| 3,528 sq.ft.	$1,350,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 1.88% Airbnb Rental Income: $2639 Traditional Rental Income: $4612 Airbnb ROI: -0.19% 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,...	5 beds \| 5 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 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: 0.21% Traditional cash on cash: 0.73% Airbnb Rental Income: $2639 Traditional Rental Income: $2590 Airbnb ROI: 0.21% 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: 0.61% Traditional cash on cash: 0.87% Airbnb Rental Income: $3501 Traditional Rental Income: $3032 Airbnb ROI: 0.61% Traditional ROI: 0.87%
9518 Quail Holw #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: 3.41% Traditional cash on cash: 3.41% Airbnb Rental Income: $3501 Traditional Rental Income: $2728 Airbnb ROI: 3.41% Traditional ROI: 3.41%
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: 0.75% Traditional cash on cash: 2.11% Airbnb Rental Income: $1965 Traditional Rental Income: $2210 Airbnb ROI: 0.75% Traditional ROI: 2.11%
111 GLORIA SAINT MICHAELS, MD Essentially a NEW HOME! Extensively, tastefully and professionally renovated 1965 rancher ...	2 beds \| 2 baths \| 1,125 sq.ft.	$435,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 2.92% Airbnb Rental Income: $1965 Traditional Rental Income: $1890 Airbnb ROI: 1.84% Traditional ROI: 2.92%
9545 Quail Holw #205 SAINT MICHAELS, MD Desirable Martingham Community is the location of this fabulous Quail Hollow unit nestled...	2 beds \| 3 baths \| 1,800 sq.ft.	$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 This BRAND NEW Arts & Crafts home sits on a quaint corner lot in picturesque Saint Michael...	3 beds \| 2 baths \| 2,027 sq.ft.	$859,900	Airbnb cash on cash: 2.21% Traditional cash on cash: 2.09% Airbnb Rental Income: $3501 Traditional Rental Income: $2629 Airbnb ROI: 2.21% Traditional ROI: 2.09%
24390 Oakwood Park Rd SAINT MICHAELS, MD Significant price improvement! Welcome to your private waterfront retreat just minutes fro...	4 beds \| 3 baths \| 2,839 sq.ft.	$1,679,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 1.19% Airbnb Rental Income: $2639 Traditional Rental Income: $4217 Airbnb ROI: -0.22% Traditional ROI: 1.19%
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: 1.39% 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 \| 3 baths \| 3,575 sq.ft.	$1,795,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 0.55% Airbnb Rental Income: $2639 Traditional Rental Income: $3902 Airbnb ROI: -0.59% 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: 0.92% Traditional cash on cash: 0.39% Airbnb Rental Income: $3501 Traditional Rental Income: $2121 Airbnb ROI: 0.92% Traditional ROI: 0.39%
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: 4.86% Traditional cash on cash: 3.36% Airbnb Rental Income: $3501 Traditional Rental Income: $2132 Airbnb ROI: 4.86% 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 \| 2 baths \| 2,420 sq.ft.	$525,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 5.65% Airbnb Rental Income: $2639 Traditional Rental Income: $3650 Airbnb ROI: 2.31% 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 \| 2 baths \| 2,420 sq.ft.	$525,000	Airbnb cash on cash: 2.32% Traditional cash on cash: 5.66% Airbnb Rental Income: $2639 Traditional Rental Income: $3652 Airbnb ROI: 2.32% 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 \| 4,728 sq.ft.	$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 \| 4 baths \| 3,677 sq.ft.	$2,550,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 0.88% Airbnb Rental Income: $2639 Traditional Rental Income: $5714 Airbnb ROI: -0.69% 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 \| 2 baths \| 2,284 sq.ft.	$1,885,000	Airbnb cash on cash: -0.22% Traditional cash on cash: -0.18% Airbnb Rental Income: $3501 Traditional Rental Income: $2797 Airbnb ROI: -0.22% 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...	4 beds \| 2 baths \| 2,798 sq.ft.	$739,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 2.6% Airbnb Rental Income: $2639 Traditional Rental Income: $3132 Airbnb ROI: 0.97% 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: 0.41% Traditional cash on cash: 1.73% Airbnb Rental Income: $2639 Traditional Rental Income: $3703 Airbnb ROI: 0.41% 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: -0.29% Traditional cash on cash: -0.19% Airbnb Rental Income: $3501 Traditional Rental Income: $2936 Airbnb ROI: -0.29% Traditional ROI: -0.19%
504 Seymour Ave SAINT MICHAELS, MD Charming yet completely reimagined, this beautifully remodeled home offers refined Eastern...	3 beds \| 2 baths \| 2,200 sq.ft.	$1,200,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 1.34% Airbnb Rental Income: $3501 Traditional Rental Income: $3049 Airbnb ROI: 1.05% 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 \| 2,348 sq.ft.	$598,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 2.31% Airbnb Rental Income: $3501 Traditional Rental Income: $2218 Airbnb ROI: 3.23% 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 \| 1,988 sq.ft.	$795,000	Airbnb cash on cash: 1% Traditional cash on cash: 2.63% Airbnb Rental Income: $2639 Traditional Rental Income: $3222 Airbnb ROI: 1% Traditional ROI: 2.63%
24561 Deepwater Pt 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: 2.59% Traditional cash on cash: 2.85% Airbnb Rental Income: $3501 Traditional Rental Income: $2891 Airbnb ROI: 2.59% Traditional ROI: 2.85%
360 PERRY CABIN SAINT MICHAELS, MD Professional photos coming. Welcome to historic St. Michaels on the Miles River. This 3 b...	3 beds \| 3 baths \| N/A	$965,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 0.42% Airbnb Rental Income: $3501 Traditional Rental Income: $2550 Airbnb ROI: 0.62% Traditional ROI: 0.42%
24580-#2 Deepwater Pt SAINT MICHAELS, MD 24580-#2 Deepwater Pt, SAINT MICHAELS, MD 21663 \| Townhouse	2 beds \| 2 baths \| 1,296 sq.ft.	$409,500	Airbnb cash on cash: 0.8% Traditional cash on cash: 1.43% Airbnb Rental Income: $1965 Traditional Rental Income: $1690 Airbnb ROI: 0.8% Traditional ROI: 1.43%

Real Estate investment in Saint-michaels, MD

There are 48 properties for sale in the city of Saint Michaels . The median list price in Saint Michaels is $912,450 and the average price per square foot is $375. 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 $2,488.

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

There are 48 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 $2,639.

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: 0.94%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $2639

Traditional Rental Income: $3037

Airbnb ROI: 0.94%

Traditional ROI: 2.51%

24700 Deepwater Point Dr #1

SAINT MICHAELS, MD

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

$369,000

Airbnb cash on cash: 1.66%

Traditional cash on cash: 2.74%

Airbnb Rental Income: $1965

Traditional Rental Income: $1823

Airbnb ROI: 1.66%

Traditional ROI: 2.74%

938 Marea Ter

SAINT MICHAELS, MD

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

$2,249,000

Airbnb cash on cash: -0.64%

Traditional cash on cash: 1.9%

Airbnb Rental Income: $2639

Traditional Rental Income: $7308

Airbnb ROI: -0.64%

Traditional ROI: 1.9%

24830 DEEPWATER POINT DR

SAINT MICHAELS, MD

3 beds | 3 baths | N/A

$2,425,000

Airbnb cash on cash: -0.15%

Traditional cash on cash: -0.03%

Airbnb Rental Income: $3501

Traditional Rental Income: $3017

Airbnb ROI: -0.15%

Traditional ROI: -0.03%

9206 Martingham Dr

SAINT MICHAELS, MD

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

$725,000

Airbnb cash on cash: 1.22%

Traditional cash on cash: 3.14%

Airbnb Rental Income: $2639

Traditional Rental Income: $3306

Airbnb ROI: 1.22%

Traditional ROI: 3.14%

23961 Lynnewood Dr

SAINT MICHAELS, MD

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

$3,100,000

Airbnb cash on cash: -0.92%

Traditional cash on cash: 0.02%

Airbnb Rental Income: $2639

Traditional Rental Income: $4724

Airbnb ROI: -0.92%

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: -0.19%

Traditional cash on cash: 1.88%

Airbnb Rental Income: $2639

Traditional Rental Income: $4612

Airbnb ROI: -0.19%

Traditional ROI: 1.88%

203 Chew Ave E

SAINT MICHAELS, MD

5 beds | 5 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%