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.

Condos for Sale in Chestertown, MD

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

Showing 3 Condo 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
103 LANDING Lane CHESTERTOWN, MD MOTIVATED SELLER - BRING OFFERS. Welcome to 103 Landing Lane: a meticulously maintained 2-...	2 beds \| 3 baths \| 2,100 sq.ft.	$499,999	Airbnb cash on cash: -0.82% Traditional cash on cash: 1.84% Airbnb Rental Income: $2055 Traditional Rental Income: $2769 Airbnb ROI: -0.82% Traditional ROI: 1.84%
117 N WATER Street #3B CHESTERTOWN, MD Set within a stately 1800s waterfront home, this beautifully renovated one-bedroom condomi...	1 beds \| 1 baths \| N/A	$295,000	Airbnb cash on cash: -5.79% Traditional cash on cash: -4.51% Airbnb Rental Income: $1182 Traditional Rental Income: $1150 Airbnb ROI: -5.79% Traditional ROI: -4.51%
Other Investment Properties for Sale in Chestertown
6746 QUAKER NECK Road CHESTERTOWN , MD	5 beds \| 3 baths \| 3,371 sq.ft.	$349,000	Airbnb cash on cash: 7.5% Traditional cash on cash: 9.12% Airbnb Rental Income: $3918 Traditional Rental Income: $3607 Airbnb ROI: 7.5% Traditional ROI: 9.12%
22400 GREAT OAK LANDING RD. CHESTERTOWN , MD Welcome to this beautifully crafted home in the water-oriented community of Great Oak Esta...	4 beds \| 3 baths \| 2,864 sq.ft.	$649,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 1.49% Airbnb Rental Income: $2789 Traditional Rental Income: $2047 Airbnb ROI: 1.64% Traditional ROI: 1.49%
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%
123 TRAFFORD Drive CHESTERTOWN , MD Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedr...	4 beds \| 3 baths \| 2,504 sq.ft.	$375,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 6.36% Airbnb Rental Income: $2789 Traditional Rental Income: $3142 Airbnb ROI: 3.5% Traditional ROI: 6.36%
124 WILTON Road 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%
8630 ELM Road CHESTERTOWN , MD Located in a beautiful waterfront community, this refreshed 5-bedroom, 2.5-bath home offer...	5 beds \| 3 baths \| 1,936 sq.ft.	$424,900	Airbnb cash on cash: 5.75% Traditional cash on cash: 5.96% Airbnb Rental Income: $3918 Traditional Rental Income: $3160 Airbnb ROI: 5.75% Traditional ROI: 5.96%
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%
213 BYFORD Drive CHESTERTOWN , MD Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was to...	4 beds \| 2 baths \| 1,277 sq.ft.	$372,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 5.07% Airbnb Rental Income: $2789 Traditional Rental Income: $2670 Airbnb ROI: 3.53% Traditional ROI: 5.07%
101 S COLLEGE Avenue CHESTERTOWN , MD This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Tho...	2 beds \| 2 baths \| 1,036 sq.ft.	$369,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 2.75% Airbnb Rental Income: $2055 Traditional Rental Income: $1723 Airbnb ROI: 2.18% Traditional ROI: 2.75%

Your search for investment property begins and ends here

Condos for Sale in Chestertown, MD

103 LANDING Lane

CHESTERTOWN, MD

2 beds | 3 baths | 2,100 sq.ft.

$499,999

Airbnb cash on cash: -0.82%

Traditional cash on cash: 1.84%

Airbnb Rental Income: $2055

Traditional Rental Income: $2769

Airbnb ROI: -0.82%

Traditional ROI: 1.84%

117 N WATER Street #3B

CHESTERTOWN, MD

1 beds | 1 baths | N/A

$295,000

Airbnb cash on cash: -5.79%

Traditional cash on cash: -4.51%

Airbnb Rental Income: $1182

Traditional Rental Income: $1150

Airbnb ROI: -5.79%

Traditional ROI: -4.51%

Other Investment Properties for Sale in Chestertown

CHESTERTOWN , MD

5 beds | 3 baths | 3,371 sq.ft.

$349,000

Airbnb cash on cash: 7.5%

Traditional cash on cash: 9.12%

Airbnb Rental Income: $3918

Traditional Rental Income: $3607

Airbnb ROI: 7.5%

Traditional ROI: 9.12%

CHESTERTOWN , MD

4 beds | 3 baths | 2,864 sq.ft.

$649,000

Airbnb cash on cash: 1.64%

Traditional cash on cash: 1.49%

Airbnb Rental Income: $2789

Traditional Rental Income: $2047

Airbnb ROI: 1.64%

Traditional ROI: 1.49%

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%

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%

CHESTERTOWN , MD

4 beds | 3 baths | 2,504 sq.ft.

$375,000

Airbnb cash on cash: 3.5%

Traditional cash on cash: 6.36%

Airbnb Rental Income: $2789

Traditional Rental Income: $3142

Airbnb ROI: 3.5%

Traditional ROI: 6.36%

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%

CHESTERTOWN , MD

5 beds | 3 baths | 1,936 sq.ft.

$424,900

Airbnb cash on cash: 5.75%