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.	$349,000	Airbnb cash on cash: 7.5% Traditional cash on cash: 9.12% Airbnb Rental Income: $3918 Traditional Rental Income: $3607 Airbnb ROI: 7.5% Traditional ROI: 9.12%
22400 GREAT OAK LANDING RD. CHESTERTOWN, MD Welcome to this beautifully crafted home in the water-oriented community of Great Oak Esta...	4 beds \| 3 baths \| 2,864 sq.ft.	$649,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 1.49% Airbnb Rental Income: $2789 Traditional Rental Income: $2047 Airbnb ROI: 1.64% Traditional ROI: 1.49%
10540 TONOPAH Road CHESTERTOWN, MD Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge ...	3 beds \| 2 baths \| 1,404 sq.ft.	$279,000	Airbnb cash on cash: 5.38% Traditional cash on cash: 6.89% Airbnb Rental Income: $2508 Traditional Rental Income: $2300 Airbnb ROI: 5.38% Traditional ROI: 6.89%
7982 RADCLIFFE Road CHESTERTOWN, MD Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of ch...	2 beds \| 2 baths \| 1,904 sq.ft.	$478,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 3.63% Airbnb Rental Income: $2055 Traditional Rental Income: $2460 Airbnb ROI: 1.54% Traditional ROI: 3.63%
123 TRAFFORD Drive CHESTERTOWN, MD Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedr...	4 beds \| 3 baths \| 2,504 sq.ft.	$375,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 6.36% Airbnb Rental Income: $2789 Traditional Rental Income: $3142 Airbnb ROI: 3.5% Traditional ROI: 6.36%
124 Wilton Rd CHESTERTOWN, MD MOVE IN READY!! Charming 3 bedroom ranch home in the desirable water oriented community of...	3 beds \| 1 baths \| 1,056 sq.ft.	$299,900	Airbnb cash on cash: 4.85% Traditional cash on cash: 4.63% Airbnb Rental Income: $2508 Traditional Rental Income: $1839 Airbnb ROI: 4.85% Traditional ROI: 4.63%
8630 ELM Road CHESTERTOWN, MD Located in a beautiful waterfront community, this refreshed 5-bedroom, 2.5-bath home offer...	5 beds \| 3 baths \| 1,936 sq.ft.	$424,900	Airbnb cash on cash: 5.75% Traditional cash on cash: 5.96% Airbnb Rental Income: $3918 Traditional Rental Income: $3160 Airbnb ROI: 5.75% Traditional ROI: 5.96%
7828 COUNTRY CLUB Lane CHESTERTOWN, MD Welcome to this spacious brick rancher located in the desirable Country Club Estates neigh...	3 beds \| 3 baths \| 2,857 sq.ft.	$799,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 1.48% Airbnb Rental Income: $2508 Traditional Rental Income: $2300 Airbnb ROI: 0.94% Traditional ROI: 1.48%
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.	$372,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 5.07% Airbnb Rental Income: $2789 Traditional Rental Income: $2670 Airbnb ROI: 3.53% Traditional ROI: 5.07%
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: -0.82% Traditional cash on cash: 1.84% Airbnb Rental Income: $2055 Traditional Rental Income: $2769 Airbnb ROI: -0.82% Traditional ROI: 1.84%
101 S COLLEGE Avenue CHESTERTOWN, MD This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Tho...	2 beds \| 2 baths \| 1,036 sq.ft.	$369,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 2.75% Airbnb Rental Income: $2055 Traditional Rental Income: $1723 Airbnb ROI: 2.18% Traditional ROI: 2.75%
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: 3.91% Traditional cash on cash: 5.33% Airbnb Rental Income: $2789 Traditional Rental Income: $2650 Airbnb ROI: 3.91% Traditional ROI: 5.33%
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.	$489,900	Airbnb cash on cash: 2.84% Traditional cash on cash: 5.41% Airbnb Rental Income: $2789 Traditional Rental Income: $3316 Airbnb ROI: 2.84% Traditional ROI: 5.41%
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.	$829,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 1.17% Airbnb Rental Income: $2508 Traditional Rental Income: $2825 Airbnb ROI: -0.03% Traditional ROI: 1.17%
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: 4.49% Traditional cash on cash: 5.71% Airbnb Rental Income: $2508 Traditional Rental Income: $2270 Airbnb ROI: 4.49% Traditional ROI: 5.71%
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.	$275,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 5.24% Airbnb Rental Income: $2508 Traditional Rental Income: $1933 Airbnb ROI: 5.12% Traditional ROI: 5.24%
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.	$275,000	Airbnb cash on cash: 4.87% Traditional cash on cash: 7.35% Airbnb Rental Income: $2508 Traditional Rental Income: $2543 Airbnb ROI: 4.87% Traditional ROI: 7.35%
896 WASHINGTON Avenue CHESTERTOWN, MD A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial...	3 beds \| 1 baths \| 1,000 sq.ft.	$325,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 3.38% Airbnb Rental Income: $2508 Traditional Rental Income: $1628 Airbnb ROI: 4.28% Traditional ROI: 3.38%
9126 FAIRLEE Road CHESTERTOWN, MD Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beaut...	3 beds \| 2 baths \| 1,216 sq.ft.	$324,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 5.63% Airbnb Rental Income: $2508 Traditional Rental Income: $2267 Airbnb ROI: 4.43% Traditional ROI: 5.63%
8999 ORCHARD Drive CHESTERTOWN, MD Welcome to a breathtaking country estate where modern elegance, architectural grandeur, an...	5 beds \| 4 baths \| 4,353 sq.ft.	$824,900	Airbnb cash on cash: 1.79% Traditional cash on cash: 3.33% Airbnb Rental Income: $3918 Traditional Rental Income: $4259 Airbnb ROI: 1.79% Traditional ROI: 3.33%
302 S MILL Street CHESTERTOWN, MD Remarkable downtown Chestertown development opportunity outside the Historic District. Inc...	2 beds \| 1 baths \| 806 sq.ft.	$1,195,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 0.34% Airbnb Rental Income: $2055 Traditional Rental Income: $1753 Airbnb ROI: 0.14% Traditional ROI: 0.34%
117 N WATER Street #3B CHESTERTOWN, MD Set within a stately 1800s waterfront home, this beautifully renovated one-bedroom condomi...	1 beds \| 1 baths \| N/A	$295,000	Airbnb cash on cash: -5.79% Traditional cash on cash: -4.51% Airbnb Rental Income: $1182 Traditional Rental Income: $1150 Airbnb ROI: -5.79% Traditional ROI: -4.51%
1003 TWIN Court CHESTERTOWN, MD Welcome home to this beautifully maintained and thoughtfully updated residence nestled at ...	3 beds \| 3 baths \| 2,076 sq.ft.	$524,900	Airbnb cash on cash: 1.17% Traditional cash on cash: 3.39% Airbnb Rental Income: $2508 Traditional Rental Income: $2986 Airbnb ROI: 1.17% Traditional ROI: 3.39%

Real Estate investment in Chestertown, MD

There are 41 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 $175. In October 2026, the average monthly cash on cash return in Chestertown is 3.00%. The average monthly rental income in Chestertown is $2,300.

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

There are 41 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 $2,300.

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.

$349,000

Airbnb cash on cash: 7.5%

Traditional cash on cash: 9.12%

Airbnb Rental Income: $3918

Traditional Rental Income: $3607

Airbnb ROI: 7.5%

Traditional ROI: 9.12%

22400 GREAT OAK LANDING RD.

CHESTERTOWN, MD

4 beds | 3 baths | 2,864 sq.ft.

$649,000

Airbnb cash on cash: 1.64%

Traditional cash on cash: 1.49%

Airbnb Rental Income: $2789

Traditional Rental Income: $2047

Airbnb ROI: 1.64%

Traditional ROI: 1.49%

10540 TONOPAH Road

CHESTERTOWN, MD

3 beds | 2 baths | 1,404 sq.ft.

$279,000

Airbnb cash on cash: 5.38%

Traditional cash on cash: 6.89%

Airbnb Rental Income: $2508

Traditional Rental Income: $2300

Airbnb ROI: 5.38%

Traditional ROI: 6.89%

7982 RADCLIFFE Road

CHESTERTOWN, MD

2 beds | 2 baths | 1,904 sq.ft.

$478,000

Airbnb cash on cash: 1.54%

Traditional cash on cash: 3.63%

Airbnb Rental Income: $2055

Traditional Rental Income: $2460

Airbnb ROI: 1.54%

Traditional ROI: 3.63%

123 TRAFFORD Drive

CHESTERTOWN, MD

4 beds | 3 baths | 2,504 sq.ft.

$375,000

Airbnb cash on cash: 3.5%

Traditional cash on cash: 6.36%

Airbnb Rental Income: $2789

Traditional Rental Income: $3142

Airbnb ROI: 3.5%

Traditional ROI: 6.36%

124 Wilton Rd

CHESTERTOWN, MD

3 beds | 1 baths | 1,056 sq.ft.

$299,900

Airbnb cash on cash: 4.85%

Traditional cash on cash: 4.63%

Airbnb Rental Income: $2508

Traditional Rental Income: $1839

Airbnb ROI: 4.85%

Traditional ROI: 4.63%

8630 ELM Road

CHESTERTOWN, MD

5 beds | 3 baths | 1,936 sq.ft.

$424,900

Airbnb cash on cash: 5.75%

Traditional cash on cash: 5.96%

Airbnb Rental Income: $3918

Traditional Rental Income: $3160

Airbnb ROI: 5.75%

Traditional ROI: 5.96%

7828 COUNTRY CLUB Lane

CHESTERTOWN, MD

3 beds | 3 baths | 2,857 sq.ft.

$799,000

Airbnb cash on cash: 0.94%

Traditional cash on cash: 1.48%

Airbnb Rental Income: $2508

Traditional Rental Income: $2300

Airbnb ROI: 0.94%