Real Estate Investment Properties for Sale in Chestertown, NY
Looking for investment property in Chestertown, NY with high ROI ?
Explore a variety of short-term homes & houses in Chestertown, NY. Invest wisely with VRBO & Chestertown, NY 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, NY
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
18 Woodcliff AcresChestertown, NYWinter fun is just beginning in the Adirondacks! You can enjoy all the seasons year-round ... |
3 beds | 1 baths | 920 sq.ft. |
$399,000 |
Airbnb cash on cash: -0.33%
|
161 E Shore DriveChestertown, NYWelcome to one of the most breathtaking properties on Loon Lake - a true Adirondack retrea... |
3 beds | 2 baths | 2,160 sq.ft. |
$1,250,000 |
Airbnb cash on cash: -1.3%
|
123 Forest Lake RdChestertown, NY123 Forest Lake Rd, Chestertown, NY 12817 | Single Family Residential |
5 beds | 4 baths | 2,594 sq.ft. |
$659,000 |
Airbnb cash on cash: -0.48%
|
5537 State Route 8Chestertown, NY5537 State Route 8, Chestertown, NY 12817 | Single Family Residential |
2 beds | 1 baths | 1,632 sq.ft. |
$850,000 |
Airbnb cash on cash: -2.15%
|
71 Ferris RdChestertown, NY71 Ferris Rd, Chestertown, NY 12817 | Manufactured Home |
3 beds | 2 baths | 1,400 sq.ft. |
$359,500 |
Airbnb cash on cash: -0.89%
|
24 Balsam Crest Path #BChestertown, NY24 Balsam Crest Path #B, Chestertown, NY 12817 | Townhouse |
2 beds | 1 baths | 1,320 sq.ft. |
$350,000 |
Airbnb cash on cash: -2.7%
|
60 Dixon RdChestertown, NY60 Dixon Rd, Chestertown, NY 12817 | Single Family Residential |
2 beds | 1 baths | 1,160 sq.ft. |
$225,000 |
Airbnb cash on cash: -0.6%
|
11K Overlook LnChestertown, NY11K Overlook Ln, Chestertown, NY 12817 | Condo/Coop |
2 beds | 1 baths | 928 sq.ft. |
$189,000 |
Airbnb cash on cash: -2.81%
|
6378 US Route 9Chestertown, NY6378 US Route 9, Chestertown, NY 12817 | Multi Family |
1 beds | 1 baths | 3,222 sq.ft. |
$199,000 |
Airbnb cash on cash: -0.33%
|
L9 Atateka RdChestertown, NYL9 Atateka Rd, Chestertown, NY 12817 | Other |
N/A beds | N/A baths | N/A |
$299,900 |
Airbnb cash on cash: 1.94%
|
Landon Hill RdChestertown, NYLandon Hill Rd, Chestertown, NY | Other |
N/A beds | N/A baths | N/A |
$76,900 |
Airbnb cash on cash: N/A
|
Real Estate investment in Chestertown, NY
There are 11 properties for sale in the city of Chestertown . The median list price in Chestertown is $281,950 and the average price per square foot is $139. In March 2026, the average monthly cash on cash return in Chestertown is 6.00%. The average monthly rental income in Chestertown is $1,663.