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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
7517 SUNBURST AVENUE CHESTERTOWN, MD Almost new home in Chestertown! Modern three bed, two bath rancher with split floor plan....	3 beds \| 2 baths \| 1,320 sq.ft.	$254,900	Airbnb cash on cash: 8.93% Traditional cash on cash: 6.97% Airbnb Rental Income: $3452 Traditional Rental Income: $2215 Airbnb ROI: 8.93% Traditional ROI: 6.97%
6270 QUAKER NECK LANDING ROAD CHESTERTOWN, MD From the moment you drive up to this beautiful home, you are struck by the beautiful lands...	3 beds \| 2 baths \| 2,400 sq.ft.	$675,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 2.72% Airbnb Rental Income: $3452 Traditional Rental Income: $2808 Airbnb ROI: 2.53% Traditional ROI: 2.72%
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%
305 LINCOLN DRIVE CHESTERTOWN, MD Looking for extra space? This home has a large extra room that could be a primary bedroom ...	4 beds \| 3 baths \| 1,632 sq.ft.	$250,000	Airbnb cash on cash: 8.66% Traditional cash on cash: 9.38% Airbnb Rental Income: $3306 Traditional Rental Income: $2738 Airbnb ROI: 8.66% Traditional ROI: 9.38%
25285 FOXCHASE DRIVE CHESTERTOWN, MD Welcome to your private oasis! This charming home boasts mature landscaping that provides ...	3 beds \| 3 baths \| 2,010 sq.ft.	$599,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 3.06% Airbnb Rental Income: $3452 Traditional Rental Income: $2753 Airbnb ROI: 2.95% Traditional ROI: 3.06%
203 HILLTOP LANE CHESTERTOWN, MD Built in 2005, this like-new home boasts an open floor plan with inviting, bright spaces. ...	3 beds \| 3 baths \| 1,222 sq.ft.	$225,000	Airbnb cash on cash: 9.75% Traditional cash on cash: 7.79% Airbnb Rental Income: $3452 Traditional Rental Income: $2271 Airbnb ROI: 9.75% Traditional ROI: 7.79%
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%
1316 EWINGTOWN ROAD CHESTERTOWN, MD Welcome to 1316 Ewingtown Rd, where the charm of historic Chestertown meets the tranquilit...	4 beds \| 2 baths \| 2,476 sq.ft.	$625,000	Airbnb cash on cash: 2.67% Traditional cash on cash: 2.56% Airbnb Rental Income: $3306 Traditional Rental Income: $2502 Airbnb ROI: 2.67% Traditional ROI: 2.56%
24291 CHESTERTOWN ROAD CHESTERTOWN, MD Price Improvement - Welcome to this delightful brick rancher, offering over 1,500 square f...	3 beds \| 2 baths \| 1,536 sq.ft.	$342,000	Airbnb cash on cash: 6.48% Traditional cash on cash: 5.08% Airbnb Rental Income: $3452 Traditional Rental Income: $2239 Airbnb ROI: 6.48% Traditional ROI: 5.08%
481 PEAR TREE POINT ROAD CHESTERTOWN, MD Major Price Reduction - Brand New Home ready ready for ALL your Holiday Celebrations! Law...	3 beds \| 3 baths \| 1,512 sq.ft.	$374,900	Airbnb cash on cash: 6.25% Traditional cash on cash: 5.89% Airbnb Rental Income: $3452 Traditional Rental Income: $2562 Airbnb ROI: 6.25% Traditional ROI: 5.89%
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: 5.8% Traditional cash on cash: 5.22% Airbnb Rental Income: $3452 Traditional Rental Income: $2468 Airbnb ROI: 5.8% Traditional ROI: 5.22%
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.	$289,000	Airbnb cash on cash: 7.05% Traditional cash on cash: 6.35% Airbnb Rental Income: $3452 Traditional Rental Income: $2495 Airbnb ROI: 7.05% Traditional ROI: 6.35%
228 CONCORD ROAD CHESTERTOWN, MD This 1500 sq. foot rancher sits on a nice open lot with plenty of parking and room to grow...	4 beds \| 2 baths \| 1,500 sq.ft.	$329,000	Airbnb cash on cash: 6.52% Traditional cash on cash: 6.32% Airbnb Rental Income: $3306 Traditional Rental Income: $2505 Airbnb ROI: 6.52% 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%
221 RIVER ROAD CHESTERTOWN, MD Hidden within the wandering gardens, you will find this meticulously maintained home with...	5 beds \| 2 baths \| 2,240 sq.ft.	$399,000	Airbnb cash on cash: 6.3% Traditional cash on cash: 5.57% Airbnb Rental Income: $3924 Traditional Rental Income: $2805 Airbnb ROI: 6.3% Traditional ROI: 5.57%
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.	$499,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 3.15% Airbnb Rental Income: $3452 Traditional Rental Income: $2380 Airbnb ROI: 3.81% Traditional ROI: 3.15%
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%
7675 QUAKER NECK ROAD CHESTERTOWN, MD The attention to detail, superior craftsmanship and high end finishes gives this home an "...	3 beds \| 3 baths \| 1,800 sq.ft.	$639,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 3.6% Airbnb Rental Income: $3452 Traditional Rental Income: $3221 Airbnb ROI: 2.7% Traditional ROI: 3.6%
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%

Real Estate investment in Chestertown, MD

There are 23 properties for sale in the city of Chestertown . The median list price in Chestertown is $386,950 and the average price per square foot is $202. In November 2024, the average monthly cash on cash return in Chestertown is 5.00%. The average monthly rental income in Chestertown is $2,522.

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

There are 23 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

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%

7517 SUNBURST AVENUE

CHESTERTOWN, MD

3 beds | 2 baths | 1,320 sq.ft.

$254,900

Airbnb cash on cash: 8.93%

Traditional cash on cash: 6.97%

Airbnb Rental Income: $3452

Traditional Rental Income: $2215

Airbnb ROI: 8.93%

Traditional ROI: 6.97%

6270 QUAKER NECK LANDING ROAD

CHESTERTOWN, MD

3 beds | 2 baths | 2,400 sq.ft.

$675,000

Airbnb cash on cash: 2.53%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $3452

Traditional Rental Income: $2808

Airbnb ROI: 2.53%

Traditional ROI: 2.72%

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%

305 LINCOLN DRIVE

CHESTERTOWN, MD

4 beds | 3 baths | 1,632 sq.ft.

$250,000

Airbnb cash on cash: 8.66%

Traditional cash on cash: 9.38%

Airbnb Rental Income: $3306

Traditional Rental Income: $2738

Airbnb ROI: 8.66%

Traditional ROI: 9.38%

25285 FOXCHASE DRIVE

CHESTERTOWN, MD

3 beds | 3 baths | 2,010 sq.ft.

$599,000

Airbnb cash on cash: 2.95%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $3452

Traditional Rental Income: $2753

Airbnb ROI: 2.95%

Traditional ROI: 3.06%

203 HILLTOP LANE

CHESTERTOWN, MD

3 beds | 3 baths | 1,222 sq.ft.

$225,000

Airbnb cash on cash: 9.75%

Traditional cash on cash: 7.79%

Airbnb Rental Income: $3452

Traditional Rental Income: $2271

Airbnb ROI: 9.75%

Traditional ROI: 7.79%

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%