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.

W Wheatfield Twp Investment Property for Sale in Chestertown, MD

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

Showing 33 W Wheatfield Twp Investment Property 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
100 ADELA Way CHESTERTOWN, MD Days on Market Reporting Incorrectly- Property listed Oct 30, 2025 Nestled just outside ...	4 beds \| 4 baths \| 3,799 sq.ft.	$515,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 5.31% Airbnb Rental Income: $1948 Traditional Rental Income: $3673 Airbnb ROI: 0.66% Traditional ROI: 5.31%
7844 CHESTER Court CHESTERTOWN, MD Beautifully Updated Home in a Serene Setting! Welcome to this stunning home filled with th...	4 beds \| 3 baths \| 3,248 sq.ft.	$770,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 2.89% Airbnb Rental Income: $1948 Traditional Rental Income: $3409 Airbnb ROI: 0.13% Traditional ROI: 2.89%
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.	$344,900	Airbnb cash on cash: 5.01% Traditional cash on cash: 5.74% Airbnb Rental Income: $2892 Traditional Rental Income: $2457 Airbnb ROI: 5.01% Traditional ROI: 5.74%
251 DEVON Drive CHESTERTOWN, MD NO HOA OR FRONT FEES: Welcome to 251 Devon Drive located in the desirable Coventry Farms n...	3 beds \| 3 baths \| 3,935 sq.ft.	$595,000	Airbnb cash on cash: 1.67% Traditional cash on cash: 2.77% Airbnb Rental Income: $2892 Traditional Rental Income: $2834 Airbnb ROI: 1.67% 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.	$409,900	Airbnb cash on cash: 1.78% Traditional cash on cash: 5.79% Airbnb Rental Income: $1948 Traditional Rental Income: $2977 Airbnb ROI: 1.78% Traditional ROI: 5.79%
107 MALONE Avenue CHESTERTOWN, MD Welcome to 107 Malone Ave. in the friendly community of Foxley Manor....A Great place to c...	3 beds \| 1 baths \| 1,200 sq.ft.	$290,000	Airbnb cash on cash: 5.73% Traditional cash on cash: 4.96% Airbnb Rental Income: $2892 Traditional Rental Income: $2012 Airbnb ROI: 5.73% Traditional ROI: 4.96%
8833 GEORGETOWN Road CHESTERTOWN, MD Move-in ready and freshly updated in 2025! This 3-bedroom, 2-bath home offers approx. 1,60...	4 beds \| 2 baths \| 1,625 sq.ft.	$364,000	Airbnb cash on cash: 2.64% Traditional cash on cash: 6.14% Airbnb Rental Income: $1948 Traditional Rental Income: $2627 Airbnb ROI: 2.64% Traditional ROI: 6.14%
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.	$539,999	Airbnb cash on cash: -0.93% Traditional cash on cash: 1.63% Airbnb Rental Income: $1999 Traditional Rental Income: $2769 Airbnb ROI: -0.93% Traditional ROI: 1.63%
109 S COLLEGE Avenue CHESTERTOWN, MD Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial ble...	3 beds \| 3 baths \| 1,216 sq.ft.	$449,900	Airbnb cash on cash: 3.43% Traditional cash on cash: 2.44% Airbnb Rental Income: $2892 Traditional Rental Income: $1802 Airbnb ROI: 3.43% Traditional ROI: 2.44%
116 HARLAN Loop CHESTERTOWN, MD $$THE OWNER MUST RELOCATE. TAKE ADVANTAGE OF THE NEW PRICE IMPROVEMENT! $$ Welcome to Cove...	5 beds \| 4 baths \| 4,067 sq.ft.	$519,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 3.42% Airbnb Rental Income: $3223 Traditional Rental Income: $2770 Airbnb ROI: 2.86% Traditional ROI: 3.42%
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.	$649,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 5.36% Airbnb Rental Income: $1948 Traditional Rental Income: $4493 Airbnb ROI: 0.31% Traditional ROI: 5.36%
105 HIGH Street CHESTERTOWN, MD This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases clas...	5 beds \| 5 baths \| 3,243 sq.ft.	$1,395,500	Airbnb cash on cash: -0.59% Traditional cash on cash: 1.25% Airbnb Rental Income: $3223 Traditional Rental Income: $4880 Airbnb ROI: -0.59% Traditional ROI: 1.25%
304 HADAWAY Drive CHESTERTOWN, MD Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready f...	4 beds \| 2 baths \| 1,325 sq.ft.	$399,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 4.25% Airbnb Rental Income: $1948 Traditional Rental Income: $2284 Airbnb ROI: 1.98% Traditional ROI: 4.25%
112 METCALF Road CHESTERTOWN, MD Come enjoy the this 2 year old home in Historic Chestertown. The home features 3 full bedr...	3 beds \| 2 baths \| 1,280 sq.ft.	$249,950	Airbnb cash on cash: 6.64% Traditional cash on cash: 7.05% Airbnb Rental Income: $2892 Traditional Rental Income: $2320 Airbnb ROI: 6.64% Traditional ROI: 7.05%
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.	$325,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 6.49% Airbnb Rental Income: $1948 Traditional Rental Income: $2650 Airbnb ROI: 2.51% Traditional ROI: 6.49%
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	$350,000	Airbnb cash on cash: 4.57% Traditional cash on cash: 5.09% Airbnb Rental Income: $2892 Traditional Rental Income: $2392 Airbnb ROI: 4.57% Traditional ROI: 5.09%
21316 PERSIMMON Drive CHESTERTOWN, MD Back on the market through no fault of the sellers. Home inspection went well. Two bedroom...	2 beds \| 1 baths \| 1,232 sq.ft.	$179,000	Airbnb cash on cash: 5.84% Traditional cash on cash: 8.18% Airbnb Rental Income: $1999 Traditional Rental Income: $1876 Airbnb ROI: 5.84% Traditional ROI: 8.18%
7989 QUAKER NECK Road CHESTERTOWN, MD Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the ...	5 beds \| 5 baths \| 4,305 sq.ft.	$2,500,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 1.3% Airbnb Rental Income: $3223 Traditional Rental Income: $6617 Airbnb ROI: -0.48% Traditional ROI: 1.3%
23110 OLD FAIRLEE Road CHESTERTOWN, MD Turnkey Perfection! Fully Renovated Ranch Home in Desirable Fairlee! Prepare to be impress...	3 beds \| 1 baths \| 1,805 sq.ft.	$349,900	Airbnb cash on cash: 4.93% Traditional cash on cash: 3.62% Airbnb Rental Income: $2892 Traditional Rental Income: $1791 Airbnb ROI: 4.93% Traditional ROI: 3.62%
103 METCALF RD CHESTERTOWN, MD Brand new home in Historic Chestertown available for move-in this October. This home featu...	3 beds \| 2 baths \| 1,280 sq.ft.	$259,900	Airbnb cash on cash: 6.6% Traditional cash on cash: 6.24% Airbnb Rental Income: $2892 Traditional Rental Income: $2133 Airbnb ROI: 6.6% Traditional ROI: 6.24%
8750 GEORGETOWN Road CHESTERTOWN, MD Discover the perfect blend of space, privacy, and comfort at this well-maintained 3-bed, 2...	3 beds \| 2 baths \| 1,900 sq.ft.	$339,000	Airbnb cash on cash: 4.86% Traditional cash on cash: 5.75% Airbnb Rental Income: $2892 Traditional Rental Income: $2505 Airbnb ROI: 4.86% Traditional ROI: 5.75%
247 Blakefield Dr CHESTERTOWN, MD Unlock the door to your future with an exclusive offer: Qualify for an exceptional 5.05% f...	3 beds \| 3 baths \| 2,572 sq.ft.	$425,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 5.68% Airbnb Rental Income: $2892 Traditional Rental Income: $3020 Airbnb ROI: 3.67% Traditional ROI: 5.68%
8620 PARK Drive CHESTERTOWN, MD Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq f...	4 beds \| 3 baths \| 2,524 sq.ft.	$499,900	Airbnb cash on cash: 1.26% Traditional cash on cash: 5.29% Airbnb Rental Income: $1948 Traditional Rental Income: $3316 Airbnb ROI: 1.26% Traditional ROI: 5.29%
318 LINCOLN CHESTERTOWN, MD Kent County welcomes you with a move-in ready home that's full of updates! This 3-bedroom,...	3 beds \| 2 baths \| 960 sq.ft.	$269,000	Airbnb cash on cash: 6.41% Traditional cash on cash: 6.29% Airbnb Rental Income: $2892 Traditional Rental Income: $2190 Airbnb ROI: 6.41% Traditional ROI: 6.29%
108 FLYING CLOUD Drive CHESTERTOWN, MD Beautifully done! A MUST see! UPGRADED 2023-built Smart Home, tucked into a quiet and frie...	4 beds \| 3 baths \| 1,936 sq.ft.	$375,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 5.76% Airbnb Rental Income: $1948 Traditional Rental Income: $2892 Airbnb ROI: 1.61% Traditional ROI: 5.76%
204 ROLLING Road CHESTERTOWN, MD Live with ease in this beautifully updated and maintained one floor home in downtown Chest...	3 beds \| 2 baths \| 2,296 sq.ft.	$370,000	Airbnb cash on cash: 4.17% Traditional cash on cash: 5.29% Airbnb Rental Income: $2892 Traditional Rental Income: $2608 Airbnb ROI: 4.17% Traditional ROI: 5.29%
311 DEVON Drive CHESTERTOWN, MD 311 Devon Drive is located in Coventry Farms; and being located within the Chestertown tow...	5 beds \| 4 baths \| 3,504 sq.ft.	$598,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 4.45% Airbnb Rental Income: $3223 Traditional Rental Income: $3809 Airbnb ROI: 2.1% Traditional ROI: 4.45%
216 BLAKEFIELD Drive CHESTERTOWN, MD Discover the charm of this stunning new construction home in the desirable Blakefield comm...	4 beds \| 3 baths \| 2,400 sq.ft.	$579,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 3.71% Airbnb Rental Income: $1948 Traditional Rental Income: $3224 Airbnb ROI: 0.4% Traditional ROI: 3.71%
121 PRIMROSE Road CHESTERTOWN, MD Welcome to 121 Primrose Road, a spacious two-story residence offering 2,034 square feet on...	3 beds \| 3 baths \| 2,034 sq.ft.	$399,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 6.04% Airbnb Rental Income: $2892 Traditional Rental Income: $2995 Airbnb ROI: 3.97% Traditional ROI: 6.04%
7521 PINE Avenue CHESTERTOWN, MD Priced to sell! This 3-bedroom, 1-bath rancher in Quaker Estates offers convenient living ...	3 beds \| 1 baths \| 1,040 sq.ft.	$250,000	Airbnb cash on cash: 7.34% Traditional cash on cash: 6.62% Airbnb Rental Income: $2892 Traditional Rental Income: $2051 Airbnb ROI: 7.34% Traditional ROI: 6.62%
213 CENTRAL Drive CHESTERTOWN, MD Great rancher in Chester Harbor on the Queen Anne's County side of Chestertown. Fresh pain...	3 beds \| 2 baths \| 1,232 sq.ft.	$319,900	Airbnb cash on cash: 5.46% Traditional cash on cash: 5.93% Airbnb Rental Income: $2892 Traditional Rental Income: $2363 Airbnb ROI: 5.46% Traditional ROI: 5.93%
109 METCALF Road CHESTERTOWN, MD Brand new home in Historic Chestertown available for move-in Right Now. This home features...	3 beds \| 2 baths \| 1,280 sq.ft.	$264,900	Airbnb cash on cash: 7.3% Traditional cash on cash: 7.32% Airbnb Rental Income: $2892 Traditional Rental Income: $2225 Airbnb ROI: 7.3% Traditional ROI: 7.32%

Your search for investment property begins and ends here

W Wheatfield Twp Investment Property for Sale in Chestertown, MD

100 ADELA Way

CHESTERTOWN, MD

4 beds | 4 baths | 3,799 sq.ft.

$515,000

Airbnb cash on cash: 0.66%

Traditional cash on cash: 5.31%

Airbnb Rental Income: $1948

Traditional Rental Income: $3673

Airbnb ROI: 0.66%

Traditional ROI: 5.31%

7844 CHESTER Court

CHESTERTOWN, MD

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

$770,000

Airbnb cash on cash: 0.13%

Traditional cash on cash: 2.89%

Airbnb Rental Income: $1948

Traditional Rental Income: $3409

Airbnb ROI: 0.13%

Traditional ROI: 2.89%

109 WILTON Road

CHESTERTOWN, MD

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

$344,900

Airbnb cash on cash: 5.01%

Traditional cash on cash: 5.74%

Airbnb Rental Income: $2892

Traditional Rental Income: $2457

Airbnb ROI: 5.01%

Traditional ROI: 5.74%

251 DEVON Drive

CHESTERTOWN, MD

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

$595,000

Airbnb cash on cash: 1.67%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $2892

Traditional Rental Income: $2834

Airbnb ROI: 1.67%

Traditional ROI: 2.77%

165 CHAR NOR MANOR Boulevard

CHESTERTOWN, MD

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

$409,900

Airbnb cash on cash: 1.78%

Traditional cash on cash: 5.79%

Airbnb Rental Income: $1948

Traditional Rental Income: $2977

Airbnb ROI: 1.78%

Traditional ROI: 5.79%

107 MALONE Avenue

CHESTERTOWN, MD

3 beds | 1 baths | 1,200 sq.ft.

$290,000

Airbnb cash on cash: 5.73%

Traditional cash on cash: 4.96%

Airbnb Rental Income: $2892

Traditional Rental Income: $2012

Airbnb ROI: 5.73%

Traditional ROI: 4.96%

8833 GEORGETOWN Road

CHESTERTOWN, MD

4 beds | 2 baths | 1,625 sq.ft.

$364,000

Airbnb cash on cash: 2.64%

Traditional cash on cash: 6.14%

Airbnb Rental Income: $1948

Traditional Rental Income: $2627

Airbnb ROI: 2.64%

Traditional ROI: 6.14%

103 LANDING Lane

CHESTERTOWN, MD

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

$539,999

Airbnb cash on cash: -0.93%

Traditional cash on cash: 1.63%

Airbnb Rental Income: $1999

Traditional Rental Income: $2769

Airbnb ROI: -0.93%