Real Estate Investment Properties for Sale in Chestertown, MD

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

Explore a variety of short-term homes & houses in Chestertown, MD. Invest wisely with VRBO & Chestertown, MD Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Chestertown, MD

Search for Single Family Residential for Sale in Chestertown, Maryland. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 11 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
10540 TONOPAH Road CHESTERTOWN, MD Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge ...	3 beds \| 2 baths \| 1,404 sq.ft.	$279,000	Airbnb cash on cash: 5.38% Traditional cash on cash: 6.89% Airbnb Rental Income: $2508 Traditional Rental Income: $2300 Airbnb ROI: 5.38% Traditional ROI: 6.89%
7982 RADCLIFFE Road CHESTERTOWN, MD Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of ch...	2 beds \| 2 baths \| 1,904 sq.ft.	$478,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 3.63% Airbnb Rental Income: $2055 Traditional Rental Income: $2460 Airbnb ROI: 1.54% Traditional ROI: 3.63%
124 Wilton Rd CHESTERTOWN, MD MOVE IN READY!! Charming 3 bedroom ranch home in the desirable water oriented community of...	3 beds \| 1 baths \| 1,056 sq.ft.	$299,900	Airbnb cash on cash: 4.85% Traditional cash on cash: 4.63% Airbnb Rental Income: $2508 Traditional Rental Income: $1839 Airbnb ROI: 4.85% Traditional ROI: 4.63%
7828 COUNTRY CLUB Lane CHESTERTOWN, MD Welcome to this spacious brick rancher located in the desirable Country Club Estates neigh...	3 beds \| 3 baths \| 2,857 sq.ft.	$799,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 1.48% Airbnb Rental Income: $2508 Traditional Rental Income: $2300 Airbnb ROI: 0.94% Traditional ROI: 1.48%
8706 ELM Road CHESTERTOWN, MD Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroo...	3 beds \| 2 baths \| 1,232 sq.ft.	$320,000	Airbnb cash on cash: 4.49% Traditional cash on cash: 5.71% Airbnb Rental Income: $2508 Traditional Rental Income: $2270 Airbnb ROI: 4.49% Traditional ROI: 5.71%
956 WASHINGTON Avenue CHESTERTOWN, MD Nice basic rancher offering 3 bedrooms and a full bath, generous sized living room with a ...	3 beds \| 1 baths \| 1,248 sq.ft.	$275,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 5.24% Airbnb Rental Income: $2508 Traditional Rental Income: $1933 Airbnb ROI: 5.12% Traditional ROI: 5.24%
896 WASHINGTON Avenue CHESTERTOWN, MD A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial...	3 beds \| 1 baths \| 1,000 sq.ft.	$325,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 3.38% Airbnb Rental Income: $2508 Traditional Rental Income: $1628 Airbnb ROI: 4.28% Traditional ROI: 3.38%
9126 FAIRLEE Road CHESTERTOWN, MD Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beaut...	3 beds \| 2 baths \| 1,216 sq.ft.	$324,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 5.63% Airbnb Rental Income: $2508 Traditional Rental Income: $2267 Airbnb ROI: 4.43% Traditional ROI: 5.63%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chestertown, MD

10540 TONOPAH Road

CHESTERTOWN, MD

3 beds | 2 baths | 1,404 sq.ft.

$279,000

Airbnb cash on cash: 5.38%

Traditional cash on cash: 6.89%

Airbnb Rental Income: $2508

Traditional Rental Income: $2300

Airbnb ROI: 5.38%

Traditional ROI: 6.89%

7982 RADCLIFFE Road

CHESTERTOWN, MD

2 beds | 2 baths | 1,904 sq.ft.

$478,000

Airbnb cash on cash: 1.54%

Traditional cash on cash: 3.63%

Airbnb Rental Income: $2055

Traditional Rental Income: $2460

Airbnb ROI: 1.54%

Traditional ROI: 3.63%

124 Wilton Rd

CHESTERTOWN, MD

3 beds | 1 baths | 1,056 sq.ft.

$299,900

Airbnb cash on cash: 4.85%

Traditional cash on cash: 4.63%

Airbnb Rental Income: $2508

Traditional Rental Income: $1839

Airbnb ROI: 4.85%

Traditional ROI: 4.63%

7828 COUNTRY CLUB Lane

CHESTERTOWN, MD

3 beds | 3 baths | 2,857 sq.ft.

$799,000

Airbnb cash on cash: 0.94%

Traditional cash on cash: 1.48%

Airbnb Rental Income: $2508

Traditional Rental Income: $2300

Airbnb ROI: 0.94%

Traditional ROI: 1.48%

8706 ELM Road

CHESTERTOWN, MD

3 beds | 2 baths | 1,232 sq.ft.

$320,000

Airbnb cash on cash: 4.49%

Traditional cash on cash: 5.71%

Airbnb Rental Income: $2508

Traditional Rental Income: $2270

Airbnb ROI: 4.49%

Traditional ROI: 5.71%

956 WASHINGTON Avenue

CHESTERTOWN, MD

3 beds | 1 baths | 1,248 sq.ft.

$275,000

Airbnb cash on cash: 5.12%

Traditional cash on cash: 5.24%

Airbnb Rental Income: $2508

Traditional Rental Income: $1933

Airbnb ROI: 5.12%

Traditional ROI: 5.24%

896 WASHINGTON Avenue

CHESTERTOWN, MD

3 beds | 1 baths | 1,000 sq.ft.

$325,000

Airbnb cash on cash: 4.28%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $2508

Traditional Rental Income: $1628

Airbnb ROI: 4.28%

Traditional ROI: 3.38%

9126 FAIRLEE Road

CHESTERTOWN, MD

3 beds | 2 baths | 1,216 sq.ft.

$324,000

Airbnb cash on cash: 4.43%

Traditional cash on cash: 5.63%

Airbnb Rental Income: $2508

Traditional Rental Income: $2267

Airbnb ROI: 4.43%