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.

Townhouses for Sale in Chestertown, NY

Search for Townhouse for Sale in Chestertown, New York. Browse all of Mashvisor’s Townhouse listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 1 Townhouse listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
24 Balsam Crest Path #B Chestertown, NY Opportunity 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: 0.18% Traditional cash on cash: 5.33% Airbnb Rental Income: $1619 Traditional Rental Income: $2815 Airbnb ROI: 0.18% Traditional ROI: 5.33%
Other Investment Properties for Sale in Chestertown
81 Clarkson Rd Chestertown , NY Comfy, cozy home with lake rights to Loon Lake. Beautiful shared beach with docking. Extre...	2 beds \| 2 baths \| 1,086 sq.ft.	$349,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 5.69% Airbnb Rental Income: $1619 Traditional Rental Income: $2603 Airbnb ROI: 1.28% Traditional ROI: 5.69%
68 Birchwood Dr Chestertown , NY 68 Birchwood Dr, Chestertown, NY 12817 is a single family home built in 1972. <br>&l...	4 beds \| 2 baths \| 1,782 sq.ft.	$1,799,000	Airbnb cash on cash: -1.76% Traditional cash on cash: -0.76% Airbnb Rental Income: $2254 Traditional Rental Income: $3359 Airbnb ROI: -1.76% Traditional ROI: -0.76%
4A High Pines Ter Chestertown , NY Discover 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: -0.75% Traditional cash on cash: 8.39% Airbnb Rental Income: $1619 Traditional Rental Income: $3192 Airbnb ROI: -0.75% Traditional ROI: 8.39%
71 Ferris Road Chestertown , NY Tucked 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: 1.66% Traditional cash on cash: 7.97% Airbnb Rental Income: $1704 Traditional Rental Income: $3160 Airbnb ROI: 1.66% Traditional ROI: 7.97%
11K Overlook Ln Chestertown , NY 11K Overlook Ln, Chestertown, NY 12817 \| Condo/Coop	2 beds \| 1 baths \| 928 sq.ft.	$189,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 3.75% Airbnb Rental Income: $1619 Traditional Rental Income: $1716 Airbnb ROI: 0.65% Traditional ROI: 3.75%
41 Moffitt Rd Chestertown , NY 41 Moffitt Rd, Chestertown, NY 12817 \| Single Family Residential	3 beds \| 2 baths \| 2,700 sq.ft.	$740,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 1.94% Airbnb Rental Income: $1704 Traditional Rental Income: $3298 Airbnb ROI: -1.06% Traditional ROI: 1.94%
4 A High Pines Terrace Chestertown , NY Discover 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: 3.15% Traditional cash on cash: 11.67% Airbnb Rental Income: $1619 Traditional Rental Income: $3054 Airbnb ROI: 3.15% Traditional ROI: 11.67%
185 Chester Shores Dr Chestertown , NY Nestled 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: 0.09% Traditional cash on cash: 2.13% Airbnb Rental Income: $2254 Traditional Rental Income: $3447 Airbnb ROI: 0.09% Traditional ROI: 2.13%
2982 Schroon River Road Chestertown , NY Exquisite 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: 0.12% Traditional cash on cash: 3.84% Airbnb Rental Income: $2254 Traditional Rental Income: $4616 Airbnb ROI: 0.12% Traditional ROI: 3.84%
35 Schroon River Forest Chestertown , NY Welcome 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: 2.2% Traditional cash on cash: 9.33% Airbnb Rental Income: $1619 Traditional Rental Income: $2970 Airbnb ROI: 2.2% Traditional ROI: 9.33%
342-346 Starbuck Hill Rd Chestertown , NY Tucked 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: 0.76% Traditional cash on cash: 4.89% Airbnb Rental Income: $2254 Traditional Rental Income: $4380 Airbnb ROI: 0.76% Traditional ROI: 4.89%
132 Blythewood Island Rd Chestertown , NY Experience 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: -0.63% Traditional cash on cash: 0.88% Airbnb Rental Income: $2254 Traditional Rental Income: $3929 Airbnb ROI: -0.63% Traditional ROI: 0.88%
4 B High Pines Ter Chestertown , NY 4 B High Pines Ter, Chestertown, NY 12817 \| Condo/Coop	2 beds \| 2 baths \| 1,040 sq.ft.	$149,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 6.91% Airbnb Rental Income: $1619 Traditional Rental Income: $2327 Airbnb ROI: -1.27% Traditional ROI: 6.91%
14 Vanderwalker Rd Chestertown , NY 14 Vanderwalker Rd, Chestertown, NY 12817 \| Single Family Residential	3 beds \| 2 baths \| 1,488 sq.ft.	$399,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 5.28% Airbnb Rental Income: $1704 Traditional Rental Income: $3080 Airbnb ROI: 0.34% Traditional ROI: 5.28%

Your search for investment property begins and ends here

Townhouses for Sale in Chestertown, NY

24 Balsam Crest Path #B

Chestertown, NY

2 beds | 1 baths | 1,320 sq.ft.

$342,000

Airbnb cash on cash: 0.18%

Traditional cash on cash: 5.33%

Airbnb Rental Income: $1619

Traditional Rental Income: $2815

Airbnb ROI: 0.18%

Traditional ROI: 5.33%

Other Investment Properties for Sale in Chestertown

Chestertown , NY

2 beds | 2 baths | 1,086 sq.ft.

$349,000

Airbnb cash on cash: 1.28%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $1619

Traditional Rental Income: $2603

Airbnb ROI: 1.28%

Traditional ROI: 5.69%

Chestertown , NY

4 beds | 2 baths | 1,782 sq.ft.

$1,799,000

Airbnb cash on cash: -1.76%

Traditional cash on cash: -0.76%

Airbnb Rental Income: $2254

Traditional Rental Income: $3359

Airbnb ROI: -1.76%

Traditional ROI: -0.76%

Chestertown , NY

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

$235,000

Airbnb cash on cash: -0.75%

Traditional cash on cash: 8.39%

Airbnb Rental Income: $1619

Traditional Rental Income: $3192

Airbnb ROI: -0.75%

Traditional ROI: 8.39%

Chestertown , NY

3 beds | 2 baths | 1,400 sq.ft.

$324,900

Airbnb cash on cash: 1.66%

Traditional cash on cash: 7.97%

Airbnb Rental Income: $1704

Traditional Rental Income: $3160

Airbnb ROI: 1.66%

Traditional ROI: 7.97%

Chestertown , NY

2 beds | 1 baths | 928 sq.ft.

$189,000

Airbnb cash on cash: 0.65%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $1619

Traditional Rental Income: $1716

Airbnb ROI: 0.65%

Traditional ROI: 3.75%

Chestertown , NY

3 beds | 2 baths | 2,700 sq.ft.

$740,000

Airbnb cash on cash: -1.06%

Traditional cash on cash: 1.94%

Airbnb Rental Income: $1704

Traditional Rental Income: $3298

Airbnb ROI: -1.06%

Traditional ROI: 1.94%

Chestertown , NY

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

$235,000

Airbnb cash on cash: 3.15%

Traditional cash on cash: 11.67%

Airbnb Rental Income: $1619

Traditional Rental Income: $3054

Airbnb ROI: 3.15%

Traditional ROI: 11.67%

Chestertown , NY

4 beds | 2 baths | 816 sq.ft.

$924,900

Airbnb cash on cash: 0.09%

Traditional cash on cash: 2.13%