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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
9206 Martingham Dr SAINT MICHAELS, MD NEW PRICE - EXCEPTIONAL VALUE IN DESIRABLE MARTINGHAM! Welcome to 9206 Martingham Drive, a...	4 beds \| 2 baths \| 2,841 sq.ft.	$600,000	Airbnb cash on cash: 3.32% Traditional cash on cash: 3.76% Airbnb Rental Income: $3883 Traditional Rental Income: $3306 Airbnb ROI: 3.32% Traditional ROI: 3.76%
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.	$1,195,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 2.25% Airbnb Rental Income: $3883 Traditional Rental Income: $4612 Airbnb ROI: 0.84% Traditional ROI: 2.25%
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.	$1,179,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 0.76% Airbnb Rental Income: $3883 Traditional Rental Income: $2590 Airbnb ROI: 1.17% Traditional ROI: 0.76%
109 W Marengo St SAINT MICHAELS, MD Discover the allure of Historic St Michaels, a captivating town nestled on Maryland's East...	4 beds \| 3 baths \| 2,250 sq.ft.	$1,049,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 1.75% Airbnb Rental Income: $3883 Traditional Rental Income: $3199 Airbnb ROI: 1.59% Traditional ROI: 1.75%
803 New Ln SAINT MICHAELS, MD Cute Bungalow in the town of Saint Michaels and just a few blocks to the town center and w...	3 beds \| 2 baths \| 1,288 sq.ft.	$849,000	Airbnb cash on cash: 2.9% Traditional cash on cash: 1.43% Airbnb Rental Income: $4357 Traditional Rental Income: $2276 Airbnb ROI: 2.9% Traditional ROI: 1.43%
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 The perfect weekend getaway does exist-and it's more attainable than you might think. Esca...	2 beds \| 1 baths \| 1,200 sq.ft.	$549,999	Airbnb cash on cash: 1.67% Traditional cash on cash: 2.24% Airbnb Rental Income: $2507 Traditional Rental Income: $2210 Airbnb ROI: 1.67% Traditional ROI: 2.24%
9545 Quail Holw #205 SAINT MICHAELS, MD REDUCED CLEAN UNIT ... CASUAL LIVING IN SOUTH AFTER ""THE LINK AT PERRY CABIN "" MARTING...	2 beds \| 3 baths \| 1,800 sq.ft.	$374,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 5.08% Airbnb Rental Income: $2507 Traditional Rental Income: $2525 Airbnb ROI: 3.3% Traditional ROI: 5.08%
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.	$799,900	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 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: 0.44% Traditional cash on cash: 1.19% Airbnb Rental Income: $3883 Traditional Rental Income: $4217 Airbnb ROI: 0.44% Traditional ROI: 1.19%
216 E Chew Ave SAINT MICHAELS, MD PRICE REDUCED: Don't miss this rare opportunity. This special home offers spectacular and ...	4 beds \| 3 baths \| 3,575 sq.ft.	$1,595,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 0.74% Airbnb Rental Income: $3883 Traditional Rental Income: $3902 Airbnb ROI: 0.17% Traditional ROI: 0.74%
912 Calvert Ave SAINT MICHAELS, MD 912 Calvert Ave, SAINT MICHAELS, MD 21663 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$219,000	Airbnb cash on cash: 5.39% Traditional cash on cash: 2.02% Airbnb Rental Income: $2198 Traditional Rental Income: $943 Airbnb ROI: 5.39% Traditional ROI: 2.02%
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: 2.53% Traditional cash on cash: -0.91% Airbnb Rental Income: $4357 Traditional Rental Income: $943 Airbnb ROI: 2.53% Traditional ROI: -0.91%
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: 1.88% Traditional cash on cash: 0.62% Airbnb Rental Income: $3883 Traditional Rental Income: $2107 Airbnb ROI: 1.88% Traditional ROI: 0.62%
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: 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: 4.7% Traditional cash on cash: 5.99% Airbnb Rental Income: $3883 Traditional Rental Income: $3650 Airbnb ROI: 4.7% 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: 4.71% Traditional cash on cash: 6% Airbnb Rental Income: $3883 Traditional Rental Income: $3652 Airbnb ROI: 4.71% Traditional ROI: 6%
228 Perry Cabin Dr #228 / 226 SAINT MICHAELS, MD 228 Perry Cabin Dr #228 / 226, SAINT MICHAELS, MD 21663 \| Townhouse	6 beds \| 6 baths \| 4,089 sq.ft.	$1,945,000	Airbnb cash on cash: -1.53% Traditional cash on cash: 0.43% Airbnb Rental Income: $2772 Traditional Rental Income: $5751 Airbnb ROI: -1.53% Traditional ROI: 0.43%
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: $2772 Traditional Rental Income: $5088 Airbnb ROI: 0.04% Traditional ROI: 1.94%
100 Bush SAINT MICHAELS, MD 100 Bush, SAINT MICHAELS, MD 21663 \| Single Family Residential	3 beds \| 2 baths \| 1,232 sq.ft.	$440,000	Airbnb cash on cash: 6.02% Traditional cash on cash: 2.58% Airbnb Rental Income: $4357 Traditional Rental Income: $2023 Airbnb ROI: 6.02% Traditional ROI: 2.58%
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: 0.19% Traditional cash on cash: -0.18% Airbnb Rental Income: $4357 Traditional Rental Income: $2797 Airbnb ROI: 0.19% Traditional ROI: -0.18%
303 Manor SAINT MICHAELS, MD 303 Manor, SAINT MICHAELS, MD 21663 \| Single Family Residential	3 beds \| 3 baths \| 2,622 sq.ft.	$1,985,000	Airbnb cash on cash: -0.27% Traditional cash on cash: -0.69% Airbnb Rental Income: $4357 Traditional Rental Income: $2663 Airbnb ROI: -0.27% Traditional ROI: -0.69%
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: 2.48% Traditional cash on cash: 2.6% Airbnb Rental Income: $3883 Traditional Rental Income: $3132 Airbnb ROI: 2.48% 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: 1.22% Traditional cash on cash: 1.73% Airbnb Rental Income: $3883 Traditional Rental Income: $3703 Airbnb ROI: 1.22% Traditional ROI: 1.73%
504 Seymour Ave SAINT MICHAELS, MD This charming, spectacular reimagined home offers refined Eastern Shore living at its very...	3 beds \| 2 baths \| 2,200 sq.ft.	$1,049,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 1.68% Airbnb Rental Income: $4357 Traditional Rental Income: $3049 Airbnb ROI: 2.08% Traditional ROI: 1.68%
7909 Church Nck SAINT MICHAELS, MD 7909 Church Nck, SAINT MICHAELS, MD 21663 \| Single Family Residential	4 beds \| 2 baths \| 4,492 sq.ft.	$2,000,000	Airbnb cash on cash: -0.57% Traditional cash on cash: -0.98% Airbnb Rental Income: $3883 Traditional Rental Income: $2245 Airbnb ROI: -0.57% Traditional ROI: -0.98%
204 Lincoln SAINT MICHAELS, MD Rio Vista Community - No Town Taxes! Enjoy life in the desirable Rio Vista community, fea...	3 beds \| 2 baths \| 2,348 sq.ft.	$598,000	Airbnb cash on cash: 4.5% Traditional cash on cash: 2.31% Airbnb Rental Income: $4357 Traditional Rental Income: $2218 Airbnb ROI: 4.5% Traditional ROI: 2.31%
9359 Martingham SAINT MICHAELS, MD Stunning One-Level Luxury Living with Golf Course & Pond Views Perfectly positioned in on...	4 beds \| 3 baths \| 1,988 sq.ft.	$795,000	Airbnb cash on cash: 2.4% Traditional cash on cash: 2.63% Airbnb Rental Income: $3883 Traditional Rental Income: $3222 Airbnb ROI: 2.4% Traditional ROI: 2.63%
24700 Deepwater Pt #23 SAINT MICHAELS, MD 24700 Deepwater Pt #23, SAINT MICHAELS, MD 21663 \| Townhouse	2 beds \| 2 baths \| 1,487 sq.ft.	$359,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 1.9% Airbnb Rental Income: $2507 Traditional Rental Income: $1779 Airbnb ROI: 2.26% Traditional ROI: 1.9%
962 San Domingo Ct SAINT MICHAELS, MD 962 San Domingo Ct, SAINT MICHAELS, MD 21663 \| Single Family Residential	4 beds \| 4 baths \| 3,300 sq.ft.	$2,349,000	Airbnb cash on cash: -0.88% Traditional cash on cash: -0.89% Airbnb Rental Income: $3883 Traditional Rental Income: $3022 Airbnb ROI: -0.88% Traditional ROI: -0.89%
203 Canton St 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.	$309,000	Airbnb cash on cash: 8.59% Traditional cash on cash: 5.03% Airbnb Rental Income: $4357 Traditional Rental Income: $2293 Airbnb ROI: 8.59% Traditional ROI: 5.03%
24555 Deepwater Pt 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.	$679,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 2.94% Airbnb Rental Income: $3883 Traditional Rental Income: $2957 Airbnb ROI: 3.08% Traditional ROI: 2.94%
24700 Deepwater Pt #20 SAINT MICHAELS, MD 24700 Deepwater Pt #20, SAINT MICHAELS, MD 21663 \| Townhouse	2 beds \| 2 baths \| 1,477 sq.ft.	$385,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 1.47% Airbnb Rental Income: $2507 Traditional Rental Income: $1751 Airbnb ROI: 1.87% Traditional ROI: 1.47%
8670 BOZMAN NEAVITT SAINT MICHAELS, MD The experience of Rose's Garden unfolds gradually, the way the best properties always do. ...	3 beds \| 3 baths \| N/A	$1,995,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 0.25% Airbnb Rental Income: $4357 Traditional Rental Income: $3255 Airbnb ROI: 0.35% Traditional ROI: 0.25%
8240 TRICEFIELD SAINT MICHAELS, MD Nestled on a gorgeous waterfront lot just minutes from St. Michaels, this exceptional prop...	5 beds \| 6 baths \| N/A	$2,445,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 1.22% Airbnb Rental Income: $2772 Traditional Rental Income: $6790 Airbnb ROI: -0.84% Traditional ROI: 1.22%
8209 Tricefield SAINT MICHAELS, MD Experience the best of Eastern Shore Living at this stunning waterfront retreat. Set on 8+...	5 beds \| 2 baths \| 4,706 sq.ft.	$2,250,000	Airbnb cash on cash: -0.7% Traditional cash on cash: -0.08% Airbnb Rental Income: $2772 Traditional Rental Income: $3573 Airbnb ROI: -0.7% Traditional ROI: -0.08%
24678 New Post Rd SAINT MICHAELS, MD 24678 New Post Rd, SAINT MICHAELS, MD 21663 \| Single Family Residential	4 beds \| 3 baths \| 6,404 sq.ft.	$3,495,000	Airbnb cash on cash: -1.27% Traditional cash on cash: -1.38% Airbnb Rental Income: $3883 Traditional Rental Income: $2665 Airbnb ROI: -1.27% Traditional ROI: -1.38%
24375 Widgeon #37 SAINT MICHAELS, MD 24375 Widgeon #37, SAINT MICHAELS, MD 21663 \| Townhouse	3 beds \| 3 baths \| 2,100 sq.ft.	$489,000	Airbnb cash on cash: 4.8% Traditional cash on cash: 2.74% Airbnb Rental Income: $4357 Traditional Rental Income: $2501 Airbnb ROI: 4.8% Traditional ROI: 2.74%

Real Estate investment in Saint-michaels, MD

There are 43 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 $351. In August 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 43 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 $3,883.

Your search for investment property begins and ends here

Investment Property for Sale in Saint Michaels, MD

9206 Martingham Dr

SAINT MICHAELS, MD

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

$600,000

Airbnb cash on cash: 3.32%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $3883

Traditional Rental Income: $3306

Airbnb ROI: 3.32%

Traditional ROI: 3.76%

114 W Chestnut St

SAINT MICHAELS, MD

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

$1,195,000

Airbnb cash on cash: 0.84%

Traditional cash on cash: 2.25%

Airbnb Rental Income: $3883

Traditional Rental Income: $4612

Airbnb ROI: 0.84%

Traditional ROI: 2.25%

101 Mulberry St

SAINT MICHAELS, MD

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

$1,179,000

Airbnb cash on cash: 1.17%

Traditional cash on cash: 0.76%

Airbnb Rental Income: $3883

Traditional Rental Income: $2590

Airbnb ROI: 1.17%

Traditional ROI: 0.76%

109 W Marengo St

SAINT MICHAELS, MD

4 beds | 3 baths | 2,250 sq.ft.

$1,049,000

Airbnb cash on cash: 1.59%

Traditional cash on cash: 1.75%

Airbnb Rental Income: $3883

Traditional Rental Income: $3199

Airbnb ROI: 1.59%

Traditional ROI: 1.75%

803 New Ln

SAINT MICHAELS, MD

3 beds | 2 baths | 1,288 sq.ft.

$849,000

Airbnb cash on cash: 2.9%

Traditional cash on cash: 1.43%

Airbnb Rental Income: $4357

Traditional Rental Income: $2276

Airbnb ROI: 2.9%

Traditional ROI: 1.43%

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.

$549,999

Airbnb cash on cash: 1.67%

Traditional cash on cash: 2.24%

Airbnb Rental Income: $2507

Traditional Rental Income: $2210

Airbnb ROI: 1.67%

Traditional ROI: 2.24%

9545 Quail Holw #205

SAINT MICHAELS, MD

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

$374,000

Airbnb cash on cash: 3.3%

Traditional cash on cash: 5.08%

Airbnb Rental Income: $2507

Traditional Rental Income: $2525

Airbnb ROI: 3.3%