Real Estate Investment Properties for Sale in Charlestown, MD

Looking for investment property in Charlestown, MD with high ROI ?

Explore a variety of short-term homes & houses in Charlestown, MD. Invest wisely with VRBO & Charlestown, 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 Charlestown, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
15 SUNDAY Drive CHARLESTOWN, MD Unique opportunity to buy 6 adjacent properties for you to build your dream home. Public S...	2 beds \| 1 baths \| 924 sq.ft.	$1,200,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 0.23% Airbnb Rental Income: $2587 Traditional Rental Income: $1515 Airbnb ROI: 0.64% Traditional ROI: 0.23%
119 Caroline St CHARLESTOWN, MD Discover the charm of this delightful split foyer home nestled in the serene Smiths Landin...	3 beds \| 2 baths \| 1,075 sq.ft.	$359,900	Airbnb cash on cash: 7.1% Traditional cash on cash: 3.82% Airbnb Rental Income: $3996 Traditional Rental Income: $2031 Airbnb ROI: 7.1% Traditional ROI: 3.82%
572 Baltimore St CHARLESTOWN, MD 572 Baltimore St, CHARLESTOWN, MD 21914 \| Single Family Residential	6 beds \| 3 baths \| 2,738 sq.ft.	$500,000	Airbnb cash on cash: 6.11% Traditional cash on cash: 3.56% Airbnb Rental Income: $4932 Traditional Rental Income: $2732 Airbnb ROI: 6.11% Traditional ROI: 3.56%
Investment Properties for Sale in Other Cities of Maryland
2635 N CALVERT Street Baltimore , MD This beautifully renovated four-unit apartment building is ideally located in the heart of...	N/A beds \| N/A baths \| 3,292 sq.ft.	$935,000	Airbnb cash on cash: -0.76% Traditional cash on cash: -0.11% Airbnb Rental Income: $1396 Traditional Rental Income: $1535 Airbnb ROI: -0.76% Traditional ROI: -0.11%
827 LIGHT Street Baltimore , MD With over $300,000 in upgrades, this home perfectly blends historic charm with modern luxu...	3 beds \| 4 baths \| 2,736 sq.ft.	$528,695	Airbnb cash on cash: -0.75% Traditional cash on cash: 2.96% Airbnb Rental Income: $1500 Traditional Rental Income: $2894 Airbnb ROI: -0.75% Traditional ROI: 2.96%
4500 EASTWAY Baltimore , MD Price repositioned! Check it out today. This charming home offers a blend of original char...	3 beds \| 2 baths \| N/A	$495,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 2.35% Airbnb Rental Income: $1948 Traditional Rental Income: $2175 Airbnb ROI: 0.75% Traditional ROI: 2.35%
649 DOVER Street Baltimore , MD Rich with character and original charm, this beautiful home is tucked away on a cobbleston...	1 beds \| 2 baths \| 936 sq.ft.	$195,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 5.51% Airbnb Rental Income: $1107 Traditional Rental Income: $1709 Airbnb ROI: 0.24% Traditional ROI: 5.51%
502 OAKLAND Avenue Baltimore , MD Spacious brick end-of-row townhome located on a quiet residential street in the desirable ...	3 beds \| 1 baths \| 1,380 sq.ft.	$129,900	Airbnb cash on cash: 3.16% Traditional cash on cash: 9.21% Airbnb Rental Income: $1232 Traditional Rental Income: $1593 Airbnb ROI: 3.16% Traditional ROI: 9.21%
16 138TH Street unit: 106 #106 Ocean City , MD Expansive 4-Bedroom Condo with Ocean Views in Island Breeze - Rarely Available! Welcome to...	4 beds \| 3 baths \| 2,570 sq.ft.	$950,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 1.53% Airbnb Rental Income: $4007 Traditional Rental Income: $3157 Airbnb ROI: 1.52% Traditional ROI: 1.53%
5 Park Pl #431 Annapolis , MD PLEASE TAKE A LOOK AT EVERY CONDO IN THE BUILDING SOLD IN THE LAST YEAR AND THEN MAKE AN A...	1 beds \| 1 baths \| 839 sq.ft.	$489,900	Airbnb cash on cash: -1.16% Traditional cash on cash: 0.37% Airbnb Rental Income: $1744 Traditional Rental Income: $1969 Airbnb ROI: -1.16% Traditional ROI: 0.37%
1520 BYRD Street Baltimore , MD Welcome home to 1520 Byrd Street! This beautifully updated four level with 3/4bedroom, 3-f...	4 beds \| 3 baths \| 1,571 sq.ft.	$480,000	Airbnb cash on cash: 5.4% Traditional cash on cash: 3.18% Airbnb Rental Income: $4607 Traditional Rental Income: $2653 Airbnb ROI: 5.4% Traditional ROI: 3.18%
3519 ROYSTON Avenue Baltimore , MD Beautifully Renovated 3-Bedroom, 2-Bath Home Step into modern comfort with this beautifull...	3 beds \| 2 baths \| 1,989 sq.ft.	$299,900	Airbnb cash on cash: -0.58% Traditional cash on cash: 5.68% Airbnb Rental Income: $966 Traditional Rental Income: $2382 Airbnb ROI: -0.58% Traditional ROI: 5.68%
7404 POPLAR Avenue Baltimore , MD Exciting opportunity in the Eastern Heights neighborhood. This 4 bedroom 2 bath home await...	4 beds \| 2 baths \| 2,418 sq.ft.	$290,000	Airbnb cash on cash: -1.71% Traditional cash on cash: 8.44% Airbnb Rental Income: $531 Traditional Rental Income: $3026 Airbnb ROI: -1.71% Traditional ROI: 8.44%
109 E WEST Street Baltimore , MD Discover 109 East West Street, a delightful treasure in the heart of Baltimore's dynamic n...	4 beds \| 4 baths \| 2,208 sq.ft.	$379,900	Airbnb cash on cash: 2.61% Traditional cash on cash: 5.16% Airbnb Rental Income: $2738 Traditional Rental Income: $3001 Airbnb ROI: 2.61% Traditional ROI: 5.16%
1910 DRUID HILL Avenue Baltimore , MD Great investment opportunity! Excellent long term tenant in place and wishes to stay. The ...	3 beds \| 1 baths \| 1,300 sq.ft.	$140,000	Airbnb cash on cash: 2.67% Traditional cash on cash: 9.88% Airbnb Rental Income: $1036 Traditional Rental Income: $1642 Airbnb ROI: 2.67% Traditional ROI: 9.88%
3108 East Ave Parkville , MD This conveniently located 4BR/2BA Parkville home is a diamond in the rough. Featuring two ...	4 beds \| 2 baths \| 2,659 sq.ft.	$369,900	Airbnb cash on cash: 3.42% Traditional cash on cash: 4.45% Airbnb Rental Income: $2445 Traditional Rental Income: $2207 Airbnb ROI: 3.42% Traditional ROI: 4.45%
9036 Simms Ct Parkville , MD Welcome Home to Modern Comfort! Step into this beautifully reimagined residence, where eve...	3 beds \| 3 baths \| 1,409 sq.ft.	$365,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 5.9% Airbnb Rental Income: $1116 Traditional Rental Income: $2644 Airbnb ROI: 0.34% Traditional ROI: 5.9%
2303 ESSEX Street Baltimore , MD WOW!!! MAJOR PRICE ADJUSTMENT! Stunning Canton Luxury Home! This beautifully appointed 4 b...	4 beds \| 5 baths \| 3,339 sq.ft.	$794,900	Airbnb cash on cash: 2.06% Traditional cash on cash: 3.31% Airbnb Rental Income: $4486 Traditional Rental Income: $4476 Airbnb ROI: 2.06% Traditional ROI: 3.31%

Real Estate investment in Charlestown, MD

There are 3 properties for sale in the city of Charlestown . The median list price in Charlestown is $650,000 and the average price per square foot is $443. In February 2026, the average monthly cash on cash return in Charlestown is 4.00%. The average monthly rental income in Charlestown is $2,031.

Charlestown, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 3 investment properties available for sale in Charlestown.

In 2026, the best neighborhood to buy investment property is CHARLESTOWN.

The ROI for Short-Term is higher than the Long-Term in Charlestown with average rental income of $3,996.

Your search for investment property begins and ends here

Investment Property for Sale in Charlestown, MD

15 SUNDAY Drive

CHARLESTOWN, MD

2 beds | 1 baths | 924 sq.ft.

$1,200,000

Airbnb cash on cash: 0.64%

Traditional cash on cash: 0.23%

Airbnb Rental Income: $2587

Traditional Rental Income: $1515

Airbnb ROI: 0.64%

Traditional ROI: 0.23%

119 Caroline St

CHARLESTOWN, MD

3 beds | 2 baths | 1,075 sq.ft.

$359,900

Airbnb cash on cash: 7.1%

Traditional cash on cash: 3.82%

Airbnb Rental Income: $3996

Traditional Rental Income: $2031

Airbnb ROI: 7.1%

Traditional ROI: 3.82%

572 Baltimore St

CHARLESTOWN, MD

6 beds | 3 baths | 2,738 sq.ft.

$500,000

Airbnb cash on cash: 6.11%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $4932

Traditional Rental Income: $2732

Airbnb ROI: 6.11%

Traditional ROI: 3.56%

Investment Properties for Sale in Other Cities of Maryland

Baltimore , MD

N/A beds | N/A baths | 3,292 sq.ft.

$935,000

Airbnb cash on cash: -0.76%

Traditional cash on cash: -0.11%

Airbnb Rental Income: $1396

Traditional Rental Income: $1535

Airbnb ROI: -0.76%

Traditional ROI: -0.11%

Baltimore , MD

3 beds | 4 baths | 2,736 sq.ft.

$528,695

Airbnb cash on cash: -0.75%

Traditional cash on cash: 2.96%

Airbnb Rental Income: $1500

Traditional Rental Income: $2894

Airbnb ROI: -0.75%

Traditional ROI: 2.96%

Baltimore , MD

3 beds | 2 baths | N/A

$495,000

Airbnb cash on cash: 0.75%

Traditional cash on cash: 2.35%

Airbnb Rental Income: $1948

Traditional Rental Income: $2175

Airbnb ROI: 0.75%

Traditional ROI: 2.35%

Baltimore , MD

1 beds | 2 baths | 936 sq.ft.

$195,000

Airbnb cash on cash: 0.24%

Traditional cash on cash: 5.51%

Airbnb Rental Income: $1107

Traditional Rental Income: $1709

Airbnb ROI: 0.24%

Traditional ROI: 5.51%

Baltimore , MD

3 beds | 1 baths | 1,380 sq.ft.

$129,900

Airbnb cash on cash: 3.16%

Traditional cash on cash: 9.21%

Airbnb Rental Income: $1232

Traditional Rental Income: $1593

Airbnb ROI: 3.16%

Traditional ROI: 9.21%

Ocean City , MD

4 beds | 3 baths | 2,570 sq.ft.

$950,000