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 |
|---|---|---|---|
11 Mill StreetChestertown, NYThis is the ideal getaway to relax and take in the sights and smells of the Adirondacks.Th... |
3 beds | 1 baths | 1,651 sq.ft. |
$349,900 |
Airbnb cash on cash: 0.01%
|
5 Overlook Lane N unit: B/D #B/DChestertown, NYRare, year-round double Condominium at 5 Overlook Lane, B/D in Warrensburg, NY-nestled in ... |
4 beds | 4 baths | 840 sq.ft. |
$325,000 |
Airbnb cash on cash: 1.2%
|
18 Woodcliff AcresChestertown, NYOctober is beautiful at Friends Lake and you can enjoy the holidays and ski/snowmobile sea... |
3 beds | 1 baths | 920 sq.ft. |
$399,000 |
Airbnb cash on cash: -0.21%
|
28 Balsam Crest Lane unit: #C #CChestertown, NYNo maintenance, carefree living! Beautiful 3 story townhouse in the Green Mansions communi... |
2 beds | N/A baths | 1,988 sq.ft. |
$350,000 |
Airbnb cash on cash: -1.45%
|
123 Stock Farm RoadChestertown, NYTucked away on a private 3.99 acre lot, this peaceful, well-maintained retreat places you ... |
3 beds | N/A baths | 2,528 sq.ft. |
$599,000 |
Airbnb cash on cash: -0.64%
|
251 Stock Farm RoadChestertown, NYMotivated Sellers, BOM due to buyer personal reasons at no fault of the seller. Welcome to... |
2 beds | 1 baths | 1,320 sq.ft. |
$285,000 |
Airbnb cash on cash: 0.95%
|
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: -1.26%
|
Real Estate investment in Chestertown, NY
There are 7 properties for sale in the city of Chestertown . The median list price in Chestertown is $349,950 and the average price per square foot is $218. In October 2025, the average monthly cash on cash return in Chestertown is 6.00%. The average monthly rental income in Chestertown is $2,847.