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 |
|---|---|---|---|
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: 0.81%
|
4 B High Pines TerChestertown, NY4 B High Pines Ter, Chestertown, NY 12817 | Condo/Coop |
2 beds | 2 baths | 1,040 sq.ft. |
$149,000 |
Airbnb cash on cash: -3.04%
|
46 Fiddlehead Bay RdChestertown, NY46 Fiddlehead Bay Rd, Chestertown, NY 12817 | Single Family Residential |
7 beds | 8 baths | 11,038 sq.ft. |
$4,497,000 |
Airbnb cash on cash: -2.21%
|
10 Landon Hill RdChestertown, NY10 Landon Hill Rd, Chestertown, NY 12817 | Single Family Residential |
6 beds | 5 baths | 3,372 sq.ft. |
$599,000 |
Airbnb cash on cash: 1.07%
|
81 Clarkson RdChestertown, NYComfy, cozy home with lake rights to Loon Lake. Beautiful shared beach with docking. Extre... |
2 beds | 2 baths | 1,086 sq.ft. |
$420,000 |
Airbnb cash on cash: 0.26%
|
5154 U.s. 9Chestertown, NY5154 U.s. 9, Chestertown, NY 12817 | Single Family Residential |
3 beds | 1 baths | 1,225 sq.ft. |
$259,000 |
Airbnb cash on cash: 0.9%
|
22 Spring StChestertown, NY22 Spring St, Chestertown, NY 12817 | Single Family Residential |
2 beds | 1 baths | 1,021 sq.ft. |
$300,000 |
Airbnb cash on cash: 0.19%
|
84 Marina RdChestertown, NY84 Marina Rd, Chestertown, NY 12817 | Single Family Residential |
3 beds | 2 baths | 1,806 sq.ft. |
$639,000 |
Airbnb cash on cash: -1.25%
|
7189 U.s. 9Chestertown, NY7189 U.s. 9, Chestertown, NY 12817 | Single Family Residential |
4 beds | 2 baths | 1,369 sq.ft. |
$497,500 |
Airbnb cash on cash: -0.08%
|
7278 Us-9Chestertown, NY7278 Us-9, Chestertown, NY 12817 | Single Family Residential |
3 beds | 1 baths | 1,220 sq.ft. |
$765,000 |
Airbnb cash on cash: -1.48%
|
14 Vanderwalker RdChestertown, NY14 Vanderwalker Rd, Chestertown, NY 12817 | Single Family Residential |
3 beds | 2 baths | 1,488 sq.ft. |
$420,000 |
Airbnb cash on cash: -0.47%
|
190 Kingsley Ln ExtChestertown, NY190 Kingsley Ln Ext, Chestertown, NY 12817 | Single Family Residential |
5 beds | 3 baths | 2,482 sq.ft. |
$949,000 |
Airbnb cash on cash: -0.38%
|
7 May RdChestertown, NY7 May Rd, Chestertown, NY 12817 | Single Family Residential |
4 beds | 3 baths | 2,058 sq.ft. |
$464,900 |
Airbnb cash on cash: 0.55%
|
773 Atateka DrChestertown, NY773 Atateka Dr, Chestertown, NY 12817 | Single Family Residential |
2 beds | 1 baths | 651 sq.ft. |
$799,000 |
Airbnb cash on cash: -1.61%
|
20 Vetter AveChestertown, NY20 Vetter Ave, Chestertown, NY 12817 | Single Family Residential |
5 beds | 1 baths | 1,286 sq.ft. |
$395,000 |
Airbnb cash on cash: 3%
|
26 Emily LnChestertown, NY26 Emily Ln, Chestertown, NY 12817 | Single Family Residential |
3 beds | 2 baths | 1,476 sq.ft. |
$819,000 |
Airbnb cash on cash: -1.67%
|
6380 U.s. 9Chestertown, NY6380 U.s. 9, Chestertown, NY 12817 | Single Family Residential |
3 beds | 2 baths | 1,624 sq.ft. |
$219,000 |
Airbnb cash on cash: 1.55%
|
527 Potter Brook RdChestertown, NY527 Potter Brook Rd, Chestertown, NY 12817 | Single Family Residential |
3 beds | 2 baths | 1,960 sq.ft. |
$329,900 |
Airbnb cash on cash: 0.14%
|
185 Chester Shores DrChestertown, NYNestled along 100' of direct frontage on beautiful Loon Lake, this well-maintained year-ro... |
4 beds | 2 baths | 816 sq.ft. |
$924,900 |
Airbnb cash on cash: -0.12%
|
342-346 Starbuck Hill RdChestertown, 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: 0.49%
|
50 Kingsley LnChestertown, NY50 Kingsley Ln, Chestertown, NY 12817 | Single Family Residential |
4 beds | 2 baths | 2,552 sq.ft. |
$499,000 |
Airbnb cash on cash: 0.33%
|
12 Theriot AveChestertown, NY12 Theriot Ave, Chestertown, NY 12817 | Single Family Residential |
1 beds | 1 baths | 704 sq.ft. |
$212,000 |
Airbnb cash on cash: 1.42%
|
18 W Kelm Pond RdChestertown, NY18 W Kelm Pond Rd, Chestertown, NY 12817 | Single Family Residential |
5 beds | 3 baths | 2,750 sq.ft. |
$874,900 |
Airbnb cash on cash: -0.12%
|
6324 State Route 9Chestertown, NY6324 State Route 9, Chestertown, NY 12817 | Single Family Residential |
6 beds | 3 baths | 2,916 sq.ft. |
$424,900 |
Airbnb cash on cash: 2.6%
|
6378 Us-9Chestertown, NYThis is a Multi-family 2-unit rental in the heart of Chestertown! Walking distance to ever... |
1 beds | 1 baths | 3,222 sq.ft. |
$199,000 |
Airbnb cash on cash: 2.36%
|
11 S Overlook Ln #BChestertown, NY11 S Overlook Ln #B, Chestertown, NY 12817 | Condo/Coop |
2 beds | 1 baths | 1,024 sq.ft. |
$195,000 |
Airbnb cash on cash: -0.86%
|
41 Moffitt RdChestertown, NY41 Moffitt Rd, Chestertown, NY 12817 | Single Family Residential |
3 beds | 2 baths | 2,700 sq.ft. |
$740,000 |
Airbnb cash on cash: -1.43%
|
24 Balsam Crest Path #BChestertown, NYOpportunity to own an Adirondack Town Home in the private Green Mansions development. A re... |
2 beds | 1 baths | 1,320 sq.ft. |
$342,000 |
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: -0.75%
|
William Elford DrChestertown, NYWilliam Elford Dr, Chestertown, NY 12817 | Other |
N/A beds | N/A baths | N/A |
$140,000 |
Airbnb cash on cash: 7.06%
|
L1.34 Mcphillips Pine LnChestertown, NYL1.34 Mcphillips Pine Ln, Chestertown, NY 12817 | Other |
N/A beds | N/A baths | N/A |
$275,000 |
Airbnb cash on cash: 2.25%
|
2 Dixon RdChestertown, NY2 Dixon Rd, Chestertown, NY 12817 | Other |
N/A beds | N/A baths | N/A |
$189,000 |
Airbnb cash on cash: 4.6%
|
36 Fawn Ridge RdChestertown, NY36 Fawn Ridge Rd, Chestertown, NY 12817 | Other |
N/A beds | N/A baths | N/A |
$150,000 |
Airbnb cash on cash: 6.44%
|
203 Tripp Lake RdChestertown, NY203 Tripp Lake Rd, Chestertown, NY 12817 | Other |
N/A beds | N/A baths | N/A |
$1,925,000 |
Airbnb cash on cash: -1.98%
|
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%
|
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: -0.11%
|
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%
|
132 Blythewood Island RdChestertown, NYExperience the best of Adirondack lakefront living with this private direct waterfront ret... |
4 beds | 3 baths | 1,914 sq.ft. |
$1,599,000 |
Airbnb cash on cash: -0.75%
|
4A High Pines TerChestertown, 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: -1.88%
|
Real Estate investment in Chestertown, NY
There are 39 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 $149. In September 2026, the average monthly cash on cash return in Chestertown is 5.00%. The average monthly rental income in Chestertown is $2,605.