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.

Investment Property for Sale in Chestertown, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
118 CHAR NOR MANOR BOULEVARD CHESTERTOWN, MD An adorable cottage with water views of the Chester River! Nicely maintained cottage featu...	3 beds \| 2 baths \| 1,114 sq.ft.	$289,000	Airbnb cash on cash: 8.03% Traditional cash on cash: 6.32% Airbnb Rental Income: $3452 Traditional Rental Income: $2220 Airbnb ROI: 8.03% Traditional ROI: 6.32%
7500 SHORTALL STREET CHESTERTOWN, MD This charming 3-bedroom, 2-bath rancher nestled in a serene setting of Quaker Estates is a...	3 beds \| 2 baths \| 1,288 sq.ft.	$299,900	Airbnb cash on cash: 7.47% Traditional cash on cash: 5.93% Airbnb Rental Income: $3452 Traditional Rental Income: $2253 Airbnb ROI: 7.47% Traditional ROI: 5.93%
103 LANDING LANE CHESTERTOWN, MD Discover this exquisite townhome nestled within the prestigious water-oriented community o...	2 beds \| 3 baths \| 2,100 sq.ft.	$579,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 1.46% Airbnb Rental Income: $3246 Traditional Rental Income: $2769 Airbnb ROI: 0.99% Traditional ROI: 1.46%
7775 WATERVIEW LANE CHESTERTOWN, MD Charming house in Country Club Estates. Located on the 14th hole with views of the Chest...	3 beds \| 3 baths \| 1,782 sq.ft.	$620,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 3.02% Airbnb Rental Income: $3452 Traditional Rental Income: $2739 Airbnb ROI: 2.94% Traditional ROI: 3.02%
6744 CHURCH HILL ROAD CHESTERTOWN, MD Nestled in a prime suburban commercial zone, this versatile property offers 1,300 sq ft of...	3 beds \| 1 baths \| 1,298 sq.ft.	$349,000	Airbnb cash on cash: 6.33% Traditional cash on cash: 3.77% Airbnb Rental Income: $3452 Traditional Rental Income: $1848 Airbnb ROI: 6.33% Traditional ROI: 3.77%
477 PEAR TREE POINT ROAD CHESTERTOWN, MD Located within the much desired Queen Anne's County School District!! Brand new constructi...	3 beds \| 3 baths \| 1,512 sq.ft.	$399,900	Airbnb cash on cash: 5.29% Traditional cash on cash: 4.7% Airbnb Rental Income: $3452 Traditional Rental Income: $2468 Airbnb ROI: 5.29% Traditional ROI: 4.7%
116 ISLAND LARK WAY CHESTERTOWN, MD Welcome home this beautiful end unit townhome in the newer community of The Village At Che...	3 beds \| 3 baths \| 1,420 sq.ft.	$289,900	Airbnb cash on cash: 7.03% Traditional cash on cash: 6.32% Airbnb Rental Income: $3452 Traditional Rental Income: $2495 Airbnb ROI: 7.03% Traditional ROI: 6.32%
10262 JOHN CARVILL ROAD CHESTERTOWN, MD This beloved waterfront property has been a treasured family gathering place for over twen...	5 beds \| 2 baths \| 3,788 sq.ft.	$1,600,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 0.5% Airbnb Rental Income: $3924 Traditional Rental Income: $3055 Airbnb ROI: 0.52% Traditional ROI: 0.5%
411 FAIRVIEW DRIVE CHESTERTOWN, MD Eastern Shore of Maryland Waterfront Cottage is perched on the banks of Rosin Creek in Que...	3 beds \| 2 baths \| 1,680 sq.ft.	$649,000	Airbnb cash on cash: 2.85% Traditional cash on cash: 2.65% Airbnb Rental Income: $3452 Traditional Rental Income: $2568 Airbnb ROI: 2.85% Traditional ROI: 2.65%
305 LONGFELLOW DRIVE CHESTERTOWN, MD Adorable and Affordable in Chester Harbor community! This 4-bedroom 2 bath home is ready f...	4 beds \| 2 baths \| 1,470 sq.ft.	$322,000	Airbnb cash on cash: 6.59% Traditional cash on cash: 5.89% Airbnb Rental Income: $3306 Traditional Rental Income: $2353 Airbnb ROI: 6.59% Traditional ROI: 5.89%
24543 CHESTERTOWN ROAD CHESTERTOWN, MD Nestled on 10 scenic acres just outside of Chestertown, this spacious 3,280 sq ft home off...	3 beds \| 2 baths \| 3,280 sq.ft.	$475,000	Airbnb cash on cash: 4.05% Traditional cash on cash: 3.36% Airbnb Rental Income: $3452 Traditional Rental Income: $2380 Airbnb ROI: 4.05% Traditional ROI: 3.36%
11040 KYLIE LANE CHESTERTOWN, MD Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville...	4 beds \| 4 baths \| 3,684 sq.ft.	$698,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 4.92% Airbnb Rental Income: $3306 Traditional Rental Income: $4493 Airbnb ROI: 1.96% Traditional ROI: 4.92%
100 ACORN DRIVE CHESTERTOWN, MD Rare end unit townhome in Oak Hollow. Close to shopping and college. Spacious rooms. Open ...	3 beds \| 3 baths \| 1,930 sq.ft.	$299,000	Airbnb cash on cash: 6.92% Traditional cash on cash: 6.39% Airbnb Rental Income: $3452 Traditional Rental Income: $2539 Airbnb ROI: 6.92% Traditional ROI: 6.39%
109 SECOR ROAD CHESTERTOWN, MD This home is located on a quiet Cul-de-sac in a water access community of Chester Harbor o...	3 beds \| 2 baths \| 1,560 sq.ft.	$365,000	Airbnb cash on cash: 5.9% Traditional cash on cash: 5.63% Airbnb Rental Income: $3452 Traditional Rental Income: $2596 Airbnb ROI: 5.9% Traditional ROI: 5.63%
210 HILLTOP LANE CHESTERTOWN, MD Built in 2005, this beautifully maintained home offers modern comforts and an inviting atm...	3 beds \| 3 baths \| 1,200 sq.ft.	$235,000	Airbnb cash on cash: 9.28% Traditional cash on cash: 7.5% Airbnb Rental Income: $3452 Traditional Rental Income: $2294 Airbnb ROI: 9.28% Traditional ROI: 7.5%
107 DUTCHESS ROAD CHESTERTOWN, MD Welcome to Chester Harbor - a family oriented place to live! The Chester Harbor Community...	3 beds \| 2 baths \| 1,380 sq.ft.	$369,000	Airbnb cash on cash: 5.96% Traditional cash on cash: 5.06% Airbnb Rental Income: $3452 Traditional Rental Income: $2375 Airbnb ROI: 5.96% Traditional ROI: 5.06%
220 BLAKEFIELD DRIVE CHESTERTOWN, MD Brand New Gorgeous Custom Home ready in December. Fall in love with the 1st floor bedroom/...	3 beds \| 3 baths \| 1,900 sq.ft.	$479,500	Airbnb cash on cash: 4.66% Traditional cash on cash: 5.37% Airbnb Rental Income: $3452 Traditional Rental Income: $3005 Airbnb ROI: 4.66% Traditional ROI: 5.37%
109 GRANT COURT CHESTERTOWN, MD This meticulously maintained 3-bedroom, 2-bathroom ranch-style home offers the perfect ble...	3 beds \| 2 baths \| 1,344 sq.ft.	$389,900	Airbnb cash on cash: 5.34% Traditional cash on cash: 4.19% Airbnb Rental Income: $3452 Traditional Rental Income: $2268 Airbnb ROI: 5.34% Traditional ROI: 4.19%
202 GLEN STREET CHESTERTOWN, MD Brick rancher located on the corner of Greenwood and Glen Street in College Heights offers...	3 beds \| 1 baths \| 1,252 sq.ft.	$307,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 4.67% Airbnb Rental Income: $3452 Traditional Rental Income: $2025 Airbnb ROI: 6.96% Traditional ROI: 4.67%

Real Estate investment in Chestertown, MD

There are 19 properties for sale in the city of Chestertown . The median list price in Chestertown is $365,000 and the average price per square foot is $207. In December 2024, the average monthly cash on cash return in Chestertown is 5.00%. The average monthly rental income in Chestertown is $2,380.

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

There are 19 investment properties available for sale in Chestertown.

In 2024, the best neighborhood to buy investment property is CHESTERTOWN.

The ROI for Short-Term is higher than the Long-Term in Chestertown with average rental income of $3,452.

Your search for investment property begins and ends here

Investment Property for Sale in Chestertown, MD

118 CHAR NOR MANOR BOULEVARD

CHESTERTOWN, MD

3 beds | 2 baths | 1,114 sq.ft.

$289,000

Airbnb cash on cash: 8.03%

Traditional cash on cash: 6.32%

Airbnb Rental Income: $3452

Traditional Rental Income: $2220

Airbnb ROI: 8.03%

Traditional ROI: 6.32%

7500 SHORTALL STREET

CHESTERTOWN, MD

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

$299,900

Airbnb cash on cash: 7.47%

Traditional cash on cash: 5.93%

Airbnb Rental Income: $3452

Traditional Rental Income: $2253

Airbnb ROI: 7.47%

Traditional ROI: 5.93%

103 LANDING LANE

CHESTERTOWN, MD

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

$579,000

Airbnb cash on cash: 0.99%

Traditional cash on cash: 1.46%

Airbnb Rental Income: $3246

Traditional Rental Income: $2769

Airbnb ROI: 0.99%

Traditional ROI: 1.46%

7775 WATERVIEW LANE

CHESTERTOWN, MD

3 beds | 3 baths | 1,782 sq.ft.

$620,000

Airbnb cash on cash: 2.94%

Traditional cash on cash: 3.02%

Airbnb Rental Income: $3452

Traditional Rental Income: $2739

Airbnb ROI: 2.94%

Traditional ROI: 3.02%

6744 CHURCH HILL ROAD

CHESTERTOWN, MD

3 beds | 1 baths | 1,298 sq.ft.

$349,000

Airbnb cash on cash: 6.33%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $3452

Traditional Rental Income: $1848

Airbnb ROI: 6.33%

Traditional ROI: 3.77%

477 PEAR TREE POINT ROAD

CHESTERTOWN, MD

3 beds | 3 baths | 1,512 sq.ft.

$399,900

Airbnb cash on cash: 5.29%

Traditional cash on cash: 4.7%

Airbnb Rental Income: $3452

Traditional Rental Income: $2468

Airbnb ROI: 5.29%

Traditional ROI: 4.7%

116 ISLAND LARK WAY

CHESTERTOWN, MD

3 beds | 3 baths | 1,420 sq.ft.

$289,900

Airbnb cash on cash: 7.03%

Traditional cash on cash: 6.32%

Airbnb Rental Income: $3452

Traditional Rental Income: $2495

Airbnb ROI: 7.03%

Traditional ROI: 6.32%

10262 JOHN CARVILL ROAD

CHESTERTOWN, MD

5 beds | 2 baths | 3,788 sq.ft.

$1,600,000

Airbnb cash on cash: 0.52%

Traditional cash on cash: 0.5%

Airbnb Rental Income: $3924

Traditional Rental Income: $3055

Airbnb ROI: 0.52%