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
6746 QUAKER NECK Road CHESTERTOWN, MD	5 beds \| 3 baths \| 3,371 sq.ft.	$384,000	Airbnb cash on cash: 6.74% Traditional cash on cash: 8.21% Airbnb Rental Income: $3918 Traditional Rental Income: $3607 Airbnb ROI: 6.74% Traditional ROI: 8.21%
101 S MILL Street CHESTERTOWN, MD This cute as a button downtown stunner is recently updated and ready for the next owner to...	2 beds \| 3 baths \| 1,476 sq.ft.	$515,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 2.95% Airbnb Rental Income: $2063 Traditional Rental Income: $2478 Airbnb ROI: 0.98% Traditional ROI: 2.95%
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.	$380,000	Airbnb cash on cash: 3.41% Traditional cash on cash: 4.94% Airbnb Rental Income: $2778 Traditional Rental Income: $2670 Airbnb ROI: 3.41% Traditional ROI: 4.94%
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: -0.81% Traditional cash on cash: 1.84% Airbnb Rental Income: $2063 Traditional Rental Income: $2769 Airbnb ROI: -0.81% Traditional ROI: 1.84%
208 Central Dr CHESTERTOWN, MD Welcome to 208 Central Drive, located in the desirable Chester Harbor community just minut...	3 beds \| 1 baths \| 1,120 sq.ft.	$299,000	Airbnb cash on cash: 4.7% Traditional cash on cash: 4.68% Airbnb Rental Income: $2463 Traditional Rental Income: $1857 Airbnb ROI: 4.7% Traditional ROI: 4.68%
105 HIGH Street CHESTERTOWN, MD Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one ...	5 beds \| 5 baths \| 3,243 sq.ft.	$1,245,500	Airbnb cash on cash: -0.04% Traditional cash on cash: 1.52% Airbnb Rental Income: $3918 Traditional Rental Income: $4880 Airbnb ROI: -0.04% Traditional ROI: 1.52%
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.	$385,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 5.33% Airbnb Rental Income: $2778 Traditional Rental Income: $2650 Airbnb ROI: 3.88% Traditional ROI: 5.33%
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.	$2,200,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 1.61% Airbnb Rental Income: $3918 Traditional Rental Income: $6617 Airbnb ROI: -0.13% Traditional ROI: 1.61%
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: 2.74% Traditional cash on cash: 5.29% Airbnb Rental Income: $2778 Traditional Rental Income: $3316 Airbnb ROI: 2.74% Traditional ROI: 5.29%
106 QUEEN Street S CHESTERTOWN, MD Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic Dist...	3 beds \| 4 baths \| 2,472 sq.ft.	$865,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 1.08% Airbnb Rental Income: $2463 Traditional Rental Income: $2825 Airbnb ROI: -0.12% Traditional ROI: 1.08%
218 CAMELOT Drive CHESTERTOWN, MD Seller is motivated and can move quickly in 30 days! Welcome to 218 Camelot Drive, stunnin...	5 beds \| 4 baths \| 3,932 sq.ft.	$499,999	Airbnb cash on cash: 4.19% Traditional cash on cash: 5.96% Airbnb Rental Income: $3918 Traditional Rental Income: $3905 Airbnb ROI: 4.19% Traditional ROI: 5.96%
22481 GOOSE HOLLOW Drive CHESTERTOWN, MD AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. This beautifully renovated 3-bedroom, 2-...	3 beds \| 2 baths \| 1,296 sq.ft.	$279,900	Airbnb cash on cash: 4.92% Traditional cash on cash: 6.02% Airbnb Rental Income: $2463 Traditional Rental Income: $2156 Airbnb ROI: 4.92% Traditional ROI: 6.02%
222 Dutchess Rd CHESTERTOWN, MD 222 Dutchess Rd, CHESTERTOWN, MD 21620 \| Single Family Residential	3 beds \| 1 baths \| 1,096 sq.ft.	$320,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 2.74% Airbnb Rental Income: $2463 Traditional Rental Income: $1545 Airbnb ROI: 3.8% Traditional ROI: 2.74%
204 Double Creek Rd CHESTERTOWN, MD Custom builder selling his own home that has been well built, well maintained, and thought...	3 beds \| 2 baths \| 2,927 sq.ft.	$565,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 4.03% Airbnb Rental Income: $2463 Traditional Rental Income: $3130 Airbnb ROI: 1.63% Traditional ROI: 4.03%
0 Round Top Rd CHESTERTOWN, MD 0 Round Top Rd, CHESTERTOWN, MD 21620 \| Other	N/A beds \| N/A baths \| N/A	$200,000	Airbnb cash on cash: 2.93% Traditional cash on cash: 0.82% Airbnb Rental Income: $1480 Traditional Rental Income: $643 Airbnb ROI: 2.93% Traditional ROI: 0.82%
8276 BROAD NECK Road CHESTERTOWN, MD Price improvement! Wait until you see this! Impecably maintained brick house on nearly 20 ...	4 beds \| 4 baths \| 3,383 sq.ft.	$1,395,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 1.36% Airbnb Rental Income: $2778 Traditional Rental Income: $3735 Airbnb ROI: 0.12% Traditional ROI: 1.36%
101 Coleman Dr CHESTERTOWN, MD Tucked away just south of the scenic Chester River and moments from the timeless charm of ...	3 beds \| 2 baths \| 2,268 sq.ft.	$519,900	Airbnb cash on cash: 1.95% Traditional cash on cash: 4.55% Airbnb Rental Income: $2463 Traditional Rental Income: $3125 Airbnb ROI: 1.95% Traditional ROI: 4.55%
8706 ELM Road CHESTERTOWN, MD Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroo...	3 beds \| 2 baths \| 1,232 sq.ft.	$320,000	Airbnb cash on cash: 4.36% Traditional cash on cash: 5.71% Airbnb Rental Income: $2463 Traditional Rental Income: $2270 Airbnb ROI: 4.36% Traditional ROI: 5.71%
215 FAIRVIEW DR CHESTERTOWN, MD Beautiful, Well-Maintained 3BR/2.5BA Home with Upgrades - 215 Fairview Drive Owner pride ...	3 beds \| 3 baths \| N/A	$425,000	Airbnb cash on cash: 3% Traditional cash on cash: 5.32% Airbnb Rental Income: $2463 Traditional Rental Income: $2790 Airbnb ROI: 3% Traditional ROI: 5.32%
214 SILVER HEEL Road CHESTERTOWN, MD Price Reduction! VERY motivated seller-open to all reasonable offers. Welcome to this beau...	4 beds \| 3 baths \| 1,972 sq.ft.	$340,000	Airbnb cash on cash: 4.18% Traditional cash on cash: 6.92% Airbnb Rental Income: $2778 Traditional Rental Income: $2999 Airbnb ROI: 4.18% Traditional ROI: 6.92%
107 FLYING CLOUD Drive CHESTERTOWN, MD NEW PRICE - One of Chestertown's Best Values! Over 2,500 square feet of 2023 construction ...	5 beds \| 4 baths \| 2,534 sq.ft.	$375,000	Airbnb cash on cash: 6.06% Traditional cash on cash: 6.63% Airbnb Rental Income: $3918 Traditional Rental Income: $3280 Airbnb ROI: 6.06% Traditional ROI: 6.63%
102 FLYING CLOUD DR CHESTERTOWN, MD Welcome to 102 Flying Cloud a new community known as The Village of Chestertown. This is a...	3 beds \| 3 baths \| N/A	$329,900	Airbnb cash on cash: 3.3% Traditional cash on cash: 6.02% Airbnb Rental Income: $2463 Traditional Rental Income: $2705 Airbnb ROI: 3.3% Traditional ROI: 6.02%
956 WASHINGTON Avenue CHESTERTOWN, MD Nice basic rancher offering 3 bedrooms and a full bath, generous sized living room with a ...	3 beds \| 1 baths \| 1,248 sq.ft.	$285,000	Airbnb cash on cash: 4.77% Traditional cash on cash: 5.03% Airbnb Rental Income: $2463 Traditional Rental Income: $1933 Airbnb ROI: 4.77% Traditional ROI: 5.03%
109 2nd St CHESTERTOWN, MD 109 2nd St, CHESTERTOWN, MD 21620 \| Other	N/A beds \| N/A baths \| N/A	$135,000	Airbnb cash on cash: 5.26% Traditional cash on cash: 3.18% Airbnb Rental Income: $1480 Traditional Rental Income: $774 Airbnb ROI: 5.26% Traditional ROI: 3.18%
21172 WYOMING Avenue CHESTERTOWN, MD Great area and lot walking distance to the Chesapeake bay and Tolchester Marina. House is ...	4 beds \| 1 baths \| 2,920 sq.ft.	$200,000	Airbnb cash on cash: 8.62% Traditional cash on cash: 7.75% Airbnb Rental Income: $2778 Traditional Rental Income: $1960 Airbnb ROI: 8.62% Traditional ROI: 7.75%
1904 Pondtown Rd CHESTERTOWN, MD 1904 Pondtown Rd, CHESTERTOWN, MD 21620 \| Single Family Residential	3 beds \| 1 baths \| 1,967 sq.ft.	$265,000	Airbnb cash on cash: 5% Traditional cash on cash: 3.53% Airbnb Rental Income: $2463 Traditional Rental Income: $1496 Airbnb ROI: 5% Traditional ROI: 3.53%
1906 Pondtown Rd CHESTERTOWN, MD 1906 Pondtown Rd, CHESTERTOWN, MD 21620 \| Other	N/A beds \| N/A baths \| N/A	$110,000	Airbnb cash on cash: 6.86% Traditional cash on cash: 4.49% Airbnb Rental Income: $1480 Traditional Rental Income: $792 Airbnb ROI: 6.86% Traditional ROI: 4.49%
104 ACORN Drive CHESTERTOWN, MD Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,...	3 beds \| 3 baths \| 1,900 sq.ft.	$284,900	Airbnb cash on cash: 4.53% Traditional cash on cash: 7.06% Airbnb Rental Income: $2463 Traditional Rental Income: $2543 Airbnb ROI: 4.53% Traditional ROI: 7.06%

Real Estate investment in Chestertown, MD

There are 48 properties for sale in the city of Chestertown . The median list price in Chestertown is $354,788 and the average price per square foot is $164. In August 2026, the average monthly cash on cash return in Chestertown is 4.00%. The average monthly rental income in Chestertown is $2,391.

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

There are 48 investment properties available for sale in Chestertown.

In 2026, the best neighborhood to buy investment property is CHESTERTOWN.

The ROI for Long-Term is higher than the Short-Term in Chestertown with average rental income of $2,391.

Your search for investment property begins and ends here

Investment Property for Sale in Chestertown, MD

6746 QUAKER NECK Road

CHESTERTOWN, MD

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

$384,000

Airbnb cash on cash: 6.74%

Traditional cash on cash: 8.21%

Airbnb Rental Income: $3918

Traditional Rental Income: $3607

Airbnb ROI: 6.74%

Traditional ROI: 8.21%

101 S MILL Street

CHESTERTOWN, MD

2 beds | 3 baths | 1,476 sq.ft.

$515,000

Airbnb cash on cash: 0.98%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $2063

Traditional Rental Income: $2478

Airbnb ROI: 0.98%

Traditional ROI: 2.95%

213 BYFORD Drive

CHESTERTOWN, MD

4 beds | 2 baths | 1,277 sq.ft.

$380,000

Airbnb cash on cash: 3.41%

Traditional cash on cash: 4.94%

Airbnb Rental Income: $2778

Traditional Rental Income: $2670

Airbnb ROI: 3.41%

Traditional ROI: 4.94%

103 LANDING Lane

CHESTERTOWN, MD

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

$499,999

Airbnb cash on cash: -0.81%

Traditional cash on cash: 1.84%

Airbnb Rental Income: $2063

Traditional Rental Income: $2769

Airbnb ROI: -0.81%

Traditional ROI: 1.84%

208 Central Dr

CHESTERTOWN, MD

3 beds | 1 baths | 1,120 sq.ft.

$299,000

Airbnb cash on cash: 4.7%

Traditional cash on cash: 4.68%

Airbnb Rental Income: $2463

Traditional Rental Income: $1857

Airbnb ROI: 4.7%

Traditional ROI: 4.68%

105 HIGH Street

CHESTERTOWN, MD

5 beds | 5 baths | 3,243 sq.ft.

$1,245,500

Airbnb cash on cash: -0.04%

Traditional cash on cash: 1.52%

Airbnb Rental Income: $3918

Traditional Rental Income: $4880

Airbnb ROI: -0.04%

Traditional ROI: 1.52%

23043 BAY SHORE Spur

CHESTERTOWN, MD

4 beds | 3 baths | 2,630 sq.ft.

$385,000

Airbnb cash on cash: 3.88%

Traditional cash on cash: 5.33%

Airbnb Rental Income: $2778

Traditional Rental Income: $2650

Airbnb ROI: 3.88%

Traditional ROI: 5.33%

7989 QUAKER NECK Road

CHESTERTOWN, MD

5 beds | 5 baths | 4,305 sq.ft.

$2,200,000

Airbnb cash on cash: -0.13%

Traditional cash on cash: 1.61%

Airbnb Rental Income: $3918

Traditional Rental Income: $6617

Airbnb ROI: -0.13%