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
202 E Chestnut St SAINT MICHAELS, MD Welcome to the William J. Wrightson House, a beautifully restored c. 1897 residence where ...	3 beds \| 3 baths \| 2,052 sq.ft.	$1,250,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 0.47% Airbnb Rental Income: $4357 Traditional Rental Income: $2454 Airbnb ROI: 1.32% Traditional ROI: 0.47%
23820 Mount Pleasant Lndg SAINT MICHAELS, MD Extraordinary waterfront living on 3.4 acres, just one mile from historic St. Michaels. Im...	4 beds \| 3 baths \| 2,815 sq.ft.	$3,000,000	Airbnb cash on cash: -0.33% Traditional cash on cash: -0.01% Airbnb Rental Income: $3889 Traditional Rental Income: $3956 Airbnb ROI: -0.33% Traditional ROI: -0.01%
101 Mulberry St SAINT MICHAELS, MD Dramatic Price Drop!!! Seller ready to sell this beautifully restored Historic Victorian i...	4 beds \| 2 baths \| 1,500 sq.ft.	$997,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 0.83% Airbnb Rental Income: $3889 Traditional Rental Income: $2590 Airbnb ROI: 1.27% Traditional ROI: 0.83%
104 Mulberry St SAINT MICHAELS, MD This beautiful historic house is located in the heart of Saint Michaels Historic District,...	3 beds \| 2 baths \| 1,938 sq.ft.	$1,399,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 0.33% Airbnb Rental Income: $4357 Traditional Rental Income: $2839 Airbnb ROI: 0.77% Traditional ROI: 0.33%
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.	$455,000	Airbnb cash on cash: 5.33% Traditional cash on cash: 3.65% Airbnb Rental Income: $4357 Traditional Rental Income: $2728 Airbnb ROI: 5.33% Traditional ROI: 3.65%
204 E Marengo St SAINT MICHAELS, MD Priced to sell! The perfect weekend getaway does exist-and it's more attainable than you m...	2 beds \| 1 baths \| 1,200 sq.ft.	$525,000	Airbnb cash on cash: 1.79% Traditional cash on cash: 2.39% Airbnb Rental Income: $2507 Traditional Rental Income: $2210 Airbnb ROI: 1.79% Traditional ROI: 2.39%
9545 Quail Holw #205 SAINT MICHAELS, MD REDUCED CLEAN UNIT ... CASUAL LIVING IN SOUTH AFTER ""THE LINK AT PERRY CABIN "" MARTINGHA...	2 beds \| 3 baths \| 1,800 sq.ft.	$374,000	Airbnb cash on cash: 2.67% Traditional cash on cash: 4.45% Airbnb Rental Income: $2507 Traditional Rental Income: $2525 Airbnb ROI: 2.67% Traditional ROI: 4.45%
807 Radcliff Ave SAINT MICHAELS, MD *BRAND NEW & MOVE-IN READY* this Arts & Crafts home sits on a quaint corner lot in pic...	3 beds \| 2 baths \| 2,027 sq.ft.	$775,000	Airbnb cash on cash: 3.41% Traditional cash on cash: 2.32% Airbnb Rental Income: $4357 Traditional Rental Income: $2629 Airbnb ROI: 3.41% Traditional ROI: 2.32%
24390 OAKWOOD PARK Road SAINT MICHAELS, MD Significant price improvement! Welcome to your private waterfront retreat just minutes fro...	4 beds \| 4 baths \| 2,839 sq.ft.	$1,679,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 1.19% Airbnb Rental Income: $3889 Traditional Rental Income: $4217 Airbnb ROI: 0.45% Traditional ROI: 1.19%
101 Brooks Ln SAINT MICHAELS, MD Seller will offer a 10K credit for a storage shed with full price offer! Welcome to this b...	3 beds \| 2 baths \| 1,120 sq.ft.	$425,000	Airbnb cash on cash: 6.65% Traditional cash on cash: 3.36% Airbnb Rental Income: $4357 Traditional Rental Income: $2132 Airbnb ROI: 6.65% Traditional ROI: 3.36%
1215 Washington SAINT MICHAELS, MD RDesirable Rio Vista Duplex - Live in One Unit and Let Rental Income Help Pay Your Mortgag...	4 beds \| 2 baths \| 2,420 sq.ft.	$499,000	Airbnb cash on cash: 4.71% Traditional cash on cash: 5.99% Airbnb Rental Income: $3889 Traditional Rental Income: $3650 Airbnb ROI: 4.71% Traditional ROI: 5.99%
1211 Washington SAINT MICHAELS, MD Desirable Rio Vista Duplex - Live in One Unit and Rent the Other! Rare opportunity to own ...	4 beds \| 2 baths \| 2,420 sq.ft.	$499,000	Airbnb cash on cash: 4.72% Traditional cash on cash: 6% Airbnb Rental Income: $3889 Traditional Rental Income: $3652 Airbnb ROI: 4.72% Traditional ROI: 6%
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: 0.04% Traditional cash on cash: 1.94% Airbnb Rental Income: $2768 Traditional Rental Income: $5088 Airbnb ROI: 0.04% Traditional ROI: 1.94%
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: 1.23% Traditional cash on cash: 1.73% Airbnb Rental Income: $3889 Traditional Rental Income: $3703 Airbnb ROI: 1.23% Traditional ROI: 1.73%
204 Lincoln SAINT MICHAELS, MD Rio Vista Community - No Town Taxes! Enjoy life in the desirable Rio Vista community, feat...	3 beds \| 2 baths \| 2,348 sq.ft.	$598,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 2.31% Airbnb Rental Income: $4357 Traditional Rental Income: $2218 Airbnb ROI: 4.51% Traditional ROI: 2.31%
104 CHERRY Street SAINT MICHAELS, MD Historic St. Michaels Opportunity! Priced to Sell Quickly! Property sold strictly "as-is."...	4 beds \| 3 baths \| 2,718 sq.ft.	$995,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 2.43% Airbnb Rental Income: $3889 Traditional Rental Income: $3956 Airbnb ROI: 1.45% Traditional ROI: 2.43%
214 Madison Ave SAINT MICHAELS, MD Opportunity awaits! This 4-bedroom, 2-bathroom, two-level home offers a functional layout ...	4 beds \| 2 baths \| 1,743 sq.ft.	$375,000	Airbnb cash on cash: 6.28% Traditional cash on cash: 5.3% Airbnb Rental Income: $3889 Traditional Rental Income: $2685 Airbnb ROI: 6.28% Traditional ROI: 5.3%

Real Estate investment in Saint-michaels, MD

There are 39 properties for sale in the city of Saint Michaels . The median list price in Saint Michaels is $1,049,000 and the average price per square foot is $414. In October 2026, the average monthly cash on cash return in Saint Michaels is 1.00%. The average monthly rental income in Saint Michaels is $2,449.

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

There are 39 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 $3,889.

Your search for investment property begins and ends here

Investment Property for Sale in Saint Michaels, MD

202 E Chestnut St

SAINT MICHAELS, MD

3 beds | 3 baths | 2,052 sq.ft.

$1,250,000

Airbnb cash on cash: 1.32%

Traditional cash on cash: 0.47%

Airbnb Rental Income: $4357

Traditional Rental Income: $2454

Airbnb ROI: 1.32%

Traditional ROI: 0.47%

23820 Mount Pleasant Lndg

SAINT MICHAELS, MD

4 beds | 3 baths | 2,815 sq.ft.

$3,000,000

Airbnb cash on cash: -0.33%

Traditional cash on cash: -0.01%

Airbnb Rental Income: $3889

Traditional Rental Income: $3956

Airbnb ROI: -0.33%

Traditional ROI: -0.01%

101 Mulberry St

SAINT MICHAELS, MD

4 beds | 2 baths | 1,500 sq.ft.

$997,000

Airbnb cash on cash: 1.27%

Traditional cash on cash: 0.83%

Airbnb Rental Income: $3889

Traditional Rental Income: $2590

Airbnb ROI: 1.27%

Traditional ROI: 0.83%

104 Mulberry St

SAINT MICHAELS, MD

3 beds | 2 baths | 1,938 sq.ft.

$1,399,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 0.33%

Airbnb Rental Income: $4357

Traditional Rental Income: $2839

Airbnb ROI: 0.77%

Traditional ROI: 0.33%

9518 Quail Holw #702

SAINT MICHAELS, MD

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

$455,000

Airbnb cash on cash: 5.33%

Traditional cash on cash: 3.65%

Airbnb Rental Income: $4357

Traditional Rental Income: $2728

Airbnb ROI: 5.33%

Traditional ROI: 3.65%

204 E Marengo St

SAINT MICHAELS, MD

2 beds | 1 baths | 1,200 sq.ft.

$525,000

Airbnb cash on cash: 1.79%

Traditional cash on cash: 2.39%

Airbnb Rental Income: $2507

Traditional Rental Income: $2210

Airbnb ROI: 1.79%

Traditional ROI: 2.39%

9545 Quail Holw #205

SAINT MICHAELS, MD

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

$374,000

Airbnb cash on cash: 2.67%

Traditional cash on cash: 4.45%

Airbnb Rental Income: $2507

Traditional Rental Income: $2525

Airbnb ROI: 2.67%

Traditional ROI: 4.45%

807 Radcliff Ave

SAINT MICHAELS, MD

3 beds | 2 baths | 2,027 sq.ft.

$775,000

Airbnb cash on cash: 3.41%

Traditional cash on cash: 2.32%

Airbnb Rental Income: $4357

Traditional Rental Income: $2629

Airbnb ROI: 3.41%