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 |
|---|---|---|---|
6378 US-9Chestertown, NYThis is a Multi-family 2-unit rental in the heart of Chestertown! Walking distance to ever... |
1 beds | 2 baths | 3,222 sq.ft. |
$199,000 |
Airbnb cash on cash: 2.38%
|
71 Ferris RoadChestertown, NYTucked away on 6.5+ wooded acres at the end of a quiet dead-end road, this brand new 3-bed... |
3 beds | 2 baths | 1,400 sq.ft. |
$324,900 |
Airbnb cash on cash: 1.09%
|
4 A High Pines TerraceChestertown, NYDiscover Adirondack living at its finest at 4A High Pines Terrace in Warrensburg, NY. Nest... |
2 beds | 2 baths | 1,404 sq.ft. |
$235,000 |
Airbnb cash on cash: 2.01%
|
185 Chester Shores DriveChestertown, NYNestled along 100' of direct frontage on beautiful Loon Lake, this well-maintained year-ro... |
4 beds | 2 baths | 1,416 sq.ft. |
$949,000 |
Airbnb cash on cash: -0.28%
|
342-346 Starbuck Hill RoadChestertown, NYTucked away on over 5 private, wooded acres yet minutes from I-87 and town, this meticulou... |
4 beds | 3 baths | 3,977 sq.ft. |
$699,900 |
Airbnb cash on cash: 0.23%
|
2982 Schroon River RoadChestertown, NYExquisite Schroon River Family Compound! Nestled on 3.9 private acres with direct frontage... |
4 beds | 3 baths | 3,300 sq.ft. |
$845,900 |
Airbnb cash on cash: -0.32%
|
35 Schroon River ForestChestertown, NYWelcome to your waterfront Adirondack retreat on the peaceful Schroon River! Located off e... |
2 beds | 2 baths | 1,246 sq.ft. |
$269,000 |
Airbnb cash on cash: 1.21%
|
Real Estate investment in Chestertown, NY
There are 7 properties for sale in the city of Chestertown . The median list price in Chestertown is $310,000 and the average price per square foot is $146. In July 2026, the average monthly cash on cash return in Chestertown is 4.00%. The average monthly rental income in Chestertown is $2,836.