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
200 WASHINGTON AVENUE CHESTERTOWN, MD Every initial showing stated what a great house but it is priced a little high!. The house...	4 beds \| 4 baths \| 2,917 sq.ft.	$745,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.09% Airbnb Rental Income: $null Traditional Rental Income: $3655 Airbnb ROI: N/A Traditional ROI: 3.09%
25800 COLLINS AVENUE CHESTERTOWN, MD Located in Country Club Estates, on a lovely, corner lot with mature trees. Solid brick ra...	3 beds \| 2 baths \| 2,162 sq.ft.	$485,000	Airbnb cash on cash: 6.57% Traditional cash on cash: 3.95% Airbnb Rental Income: $4884 Traditional Rental Income: $2693 Airbnb ROI: 6.57% Traditional ROI: 3.95%
200 FEY RD CHESTERTOWN, MD Welcome to this charming rancher situated just minutes from historic downtown Chestertown....	3 beds \| 2 baths \| N/A	$374,900	Airbnb cash on cash: 9.17% Traditional cash on cash: 5.11% Airbnb Rental Income: $4884 Traditional Rental Income: $2450 Airbnb ROI: 9.17% Traditional ROI: 5.11%
109 WILTON ROAD CHESTERTOWN, MD Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comf...	3 beds \| 2 baths \| 1,392 sq.ft.	$349,900	Airbnb cash on cash: 9.97% Traditional cash on cash: 5.64% Airbnb Rental Income: $4884 Traditional Rental Income: $2457 Airbnb ROI: 9.97% Traditional ROI: 5.64%
108 S KENT STREET CHESTERTOWN, MD Price improvement! Cute as a button in the historic district on South Kent St. This 1-bedr...	1 beds \| 2 baths \| 936 sq.ft.	$315,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 4.09% Airbnb Rental Income: $2337 Traditional Rental Income: $1867 Airbnb ROI: 3.72% Traditional ROI: 4.09%
251 DEVON DRIVE CHESTERTOWN, MD Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When ente...	3 beds \| 3 baths \| 3,935 sq.ft.	$595,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 2.77% Airbnb Rental Income: $4884 Traditional Rental Income: $2834 Airbnb ROI: 4.66% Traditional ROI: 2.77%
165 CHAR NOR MANOR BOULEVARD CHESTERTOWN, MD Chester River Views from Every Angle! Welcome to this stunning Colonial located on the Que...	4 beds \| 3 baths \| 2,258 sq.ft.	$475,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.87% Airbnb Rental Income: $null Traditional Rental Income: $2977 Airbnb ROI: N/A Traditional ROI: 4.87%
111 CEE JAY ROAD CHESTERTOWN, MD Beautiful, like new rancher built in 2021 offers 4 bedrooms and 2 baths. Luxury vinyl tile...	4 beds \| 2 baths \| 1,400 sq.ft.	$359,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.21% Airbnb Rental Income: $null Traditional Rental Income: $2399 Airbnb ROI: N/A Traditional ROI: 5.21%
103 LANDING LANE CHESTERTOWN, MD Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable...	2 beds \| 3 baths \| 2,100 sq.ft.	$559,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 1.54% Airbnb Rental Income: $3399 Traditional Rental Income: $2769 Airbnb ROI: 1.3% Traditional ROI: 1.54%
116 HARLAN LOOP CHESTERTOWN, MD Welcome to Coventry Farms in Chestertown where comfort, elegance, and space come together ...	5 beds \| 4 baths \| 4,067 sq.ft.	$529,000	Airbnb cash on cash: 7.3% Traditional cash on cash: 3.34% Airbnb Rental Income: $5900 Traditional Rental Income: $2770 Airbnb ROI: 7.3% Traditional ROI: 3.34%
11040 KYLIE LANE CHESTERTOWN, MD Rare lake front property in Kent County! Welcome to your serene getaway nestled on 2.62 ac...	4 beds \| 4 baths \| 3,684 sq.ft.	$659,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.26% Airbnb Rental Income: $null Traditional Rental Income: $4493 Airbnb ROI: N/A Traditional ROI: 5.26%
23620 LANDS END ROAD CHESTERTOWN, MD Hartwell Estate features 80 private acres with pristine, panoramic views on the mouth of t...	5 beds \| 8 baths \| 9,852 sq.ft.	$4,850,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 0.1% Airbnb Rental Income: $5900 Traditional Rental Income: $7827 Airbnb ROI: -0.59% Traditional ROI: 0.1%
105 HIGH STREET CHESTERTOWN, MD ***Photos reflect the progress as of 3 months ago. The property is now nearly completed an...	5 beds \| 5 baths \| 3,243 sq.ft.	$1,395,500	Airbnb cash on cash: 1.99% Traditional cash on cash: 2.11% Airbnb Rental Income: $5900 Traditional Rental Income: $4880 Airbnb ROI: 1.99% Traditional ROI: 2.11%
128 EDMORE ROAD CHESTERTOWN, MD Your Dream Eastern Shore Retreat Awaits! Welcome to this meticulously maintained home, wh...	4 beds \| 2 baths \| 2,568 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.36% Airbnb Rental Income: $null Traditional Rental Income: $3222 Airbnb ROI: N/A Traditional ROI: 6.36%
26889 MORGNEC ROAD CHESTERTOWN, MD This waterfront farmette is a rare find just a few minutes from downtown Chestertown and f...	2 beds \| 2 baths \| 1,966 sq.ft.	$699,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 2.33% Airbnb Rental Income: $3399 Traditional Rental Income: $2748 Airbnb ROI: 2.17% Traditional ROI: 2.33%
7961 QUAKER NECK ROAD CHESTERTOWN, MD Exquisite Waterfront Retreat on Chester River Welcome to 7961 Quaker Neck Road, Chest...	5 beds \| 4 baths \| 4,167 sq.ft.	$1,550,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 1.87% Airbnb Rental Income: $5900 Traditional Rental Income: $5133 Airbnb ROI: 1.59% Traditional ROI: 1.87%
5179 QUAKER NECK ROAD CHESTERTOWN, MD $20,000 Price Reduction! A One-of-a-Kind Historic Treasure Reimagined for Modern Living St...	1 beds \| 1 baths \| 1,148 sq.ft.	$559,900	Airbnb cash on cash: 1.65% Traditional cash on cash: 1.3% Airbnb Rental Income: $2337 Traditional Rental Income: $1571 Airbnb ROI: 1.65% Traditional ROI: 1.3%
201 BIRCH RUN ROAD CHESTERTOWN, MD This Mid Century Modern is located in Mile Tree Village, one of Chestertown's most coveted...	3 beds \| 2 baths \| 1,588 sq.ft.	$470,000	Airbnb cash on cash: 6.58% Traditional cash on cash: 4.34% Airbnb Rental Income: $4884 Traditional Rental Income: $2896 Airbnb ROI: 6.58% Traditional ROI: 4.34%
206 S WATER STREET CHESTERTOWN, MD Just in time for the annual Downrigging Festival! See tall ships sailing the Chester River...	4 beds \| 4 baths \| 2,008 sq.ft.	$648,750	Airbnb cash on cash: N/A Traditional cash on cash: 2.87% Airbnb Rental Income: $null Traditional Rental Income: $3155 Airbnb ROI: N/A Traditional ROI: 2.87%
201 BOUNDARY AVENUE CHESTERTOWN, MD Discover this spacious home offering 3,100 sq ft of living space on a acre lot with deeded...	3 beds \| 3 baths \| 3,096 sq.ft.	$449,000	Airbnb cash on cash: 7.3% Traditional cash on cash: 6.53% Airbnb Rental Income: $4884 Traditional Rental Income: $3560 Airbnb ROI: 7.3% Traditional ROI: 6.53%
907 N MEADOWVIEW DRIVE CHESTERTOWN, MD Welcome to 907 N Meadowview Drive, a beautifully maintained home in the sought-after Crest...	3 beds \| 3 baths \| 1,842 sq.ft.	$440,000	Airbnb cash on cash: 7.53% Traditional cash on cash: 4.71% Airbnb Rental Income: $4884 Traditional Rental Income: $2720 Airbnb ROI: 7.53% Traditional ROI: 4.71%
103 ADELA WAY CHESTERTOWN, MD Looking for a large spacious home in a lovely neighborhood that is close to downtown & sho...	4 beds \| 4 baths \| 5,576 sq.ft.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.72% Airbnb Rental Income: $null Traditional Rental Income: $3767 Airbnb ROI: N/A Traditional ROI: 4.72%
26933 MALLARD ROAD CHESTERTOWN, MD Stunning waterfront property with private dock site on the Chester River. The house has be...	3 beds \| 3 baths \| 1,600 sq.ft.	$625,000	Airbnb cash on cash: 4.74% Traditional cash on cash: 3.33% Airbnb Rental Income: $4884 Traditional Rental Income: $3063 Airbnb ROI: 4.74% Traditional ROI: 3.33%
23043 BAY SHORE SPUR CHESTERTOWN, MD Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 ac...	4 beds \| 3 baths \| 2,630 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.5% Airbnb Rental Income: $null Traditional Rental Income: $2650 Airbnb ROI: N/A Traditional ROI: 5.5%
515 N KENT STREET CHESTERTOWN, MD Welcome to 515 N Kent Street in the heart of Chestertown! This charming two story home fea...	4 beds \| 2 baths \| 2,220 sq.ft.	$509,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.34% Airbnb Rental Income: $null Traditional Rental Income: $2974 Airbnb ROI: N/A Traditional ROI: 4.34%
10751 MILLBROOK DR CHESTERTOWN, MD Chesapeake Landing - This home is featured on a corner lot with large living space and add...	3 beds \| 2 baths \| N/A	$375,000	Airbnb cash on cash: 8.92% Traditional cash on cash: 4.69% Airbnb Rental Income: $4884 Traditional Rental Income: $2392 Airbnb ROI: 8.92% Traditional ROI: 4.69%
7989 QUAKER NECK ROAD CHESTERTOWN, MD Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this ...	5 beds \| 5 baths \| 4,305 sq.ft.	$2,750,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 1.09% Airbnb Rental Income: $5900 Traditional Rental Income: $6617 Airbnb ROI: 0.35% Traditional ROI: 1.09%
23110 OLD FAIRLEE ROAD CHESTERTOWN, MD Renovated Ranch Home in Fairlee. This home has been updated top to bottom. Recent updates ...	3 beds \| 1 baths \| 1,805 sq.ft.	$379,900	Airbnb cash on cash: 9.13% Traditional cash on cash: 3.26% Airbnb Rental Income: $4884 Traditional Rental Income: $1791 Airbnb ROI: 9.13% Traditional ROI: 3.26%
118 LITTLE HARBOR WAY #201 CHESTERTOWN, MD An impeccably maintained, perfectly positioned two bedroom, two and one-half bath condo fe...	2 beds \| 3 baths \| 1,550 sq.ft.	$695,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 2.74% Airbnb Rental Income: $3399 Traditional Rental Income: $3219 Airbnb ROI: 1.85% Traditional ROI: 2.74%

Real Estate investment in Chestertown, MD

There are 29 properties for sale in the city of Chestertown . The median list price in Chestertown is $459,500 and the average price per square foot is $186. In September 2025, the average monthly cash on cash return in Chestertown is 5.00%. The average monthly rental income in Chestertown is $2,748.

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

There are 29 investment properties available for sale in Chestertown.

In 2025, 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 $4,884.

Your search for investment property begins and ends here

Investment Property for Sale in Chestertown, MD

200 WASHINGTON AVENUE

CHESTERTOWN, MD

4 beds | 4 baths | 2,917 sq.ft.

$745,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.09%

Airbnb Rental Income: $null

Traditional Rental Income: $3655

Airbnb ROI: N/A

Traditional ROI: 3.09%

25800 COLLINS AVENUE

CHESTERTOWN, MD

3 beds | 2 baths | 2,162 sq.ft.

$485,000

Airbnb cash on cash: 6.57%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $4884

Traditional Rental Income: $2693

Airbnb ROI: 6.57%

Traditional ROI: 3.95%

200 FEY RD

CHESTERTOWN, MD

3 beds | 2 baths | N/A

$374,900

Airbnb cash on cash: 9.17%

Traditional cash on cash: 5.11%

Airbnb Rental Income: $4884

Traditional Rental Income: $2450

Airbnb ROI: 9.17%

Traditional ROI: 5.11%

109 WILTON ROAD

CHESTERTOWN, MD

3 beds | 2 baths | 1,392 sq.ft.

$349,900

Airbnb cash on cash: 9.97%

Traditional cash on cash: 5.64%

Airbnb Rental Income: $4884

Traditional Rental Income: $2457

Airbnb ROI: 9.97%

Traditional ROI: 5.64%

108 S KENT STREET

CHESTERTOWN, MD

1 beds | 2 baths | 936 sq.ft.

$315,000

Airbnb cash on cash: 3.72%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $2337

Traditional Rental Income: $1867

Airbnb ROI: 3.72%

Traditional ROI: 4.09%

251 DEVON DRIVE

CHESTERTOWN, MD

3 beds | 3 baths | 3,935 sq.ft.

$595,000

Airbnb cash on cash: 4.66%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $4884

Traditional Rental Income: $2834

Airbnb ROI: 4.66%

Traditional ROI: 2.77%

165 CHAR NOR MANOR BOULEVARD

CHESTERTOWN, MD

4 beds | 3 baths | 2,258 sq.ft.

$475,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.87%

Airbnb Rental Income: $null

Traditional Rental Income: $2977

Airbnb ROI: N/A

Traditional ROI: 4.87%

111 CEE JAY ROAD

CHESTERTOWN, MD

4 beds | 2 baths | 1,400 sq.ft.

$359,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.21%

Airbnb Rental Income: $null

Traditional Rental Income: $2399

Airbnb ROI: N/A