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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
6369 State Route 9 Chestertown, NY Three levels of mixed-use space are available in the historic Remington Building in the he...	4 beds \| 7 baths \| 6,840 sq.ft.	$749,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 7.73% Airbnb Rental Income: $4533 Traditional Rental Income: $6566 Airbnb ROI: 3.47% Traditional ROI: 7.73%
5 Circle Chestertown, NY A rare Friends Lake find, private lake with lake access including sandy beach & deeded doc...	3 beds \| 2 baths \| 2,974 sq.ft.	$699,000	Airbnb cash on cash: 2.37% Traditional cash on cash: 3.73% Airbnb Rental Income: $3583 Traditional Rental Income: $3688 Airbnb ROI: 2.37% Traditional ROI: 3.73%
Investment Properties for Sale in Other Cities of New-york
467 Keap Street New York , NY Ainslie Tower is a ten-story, thirty-unit elevator apartment building built in 2009. Thi...	N/A beds \| N/A baths \| 65,535 sq.ft.	$27,000,000	Airbnb cash on cash: -1.37% Traditional cash on cash: -1.38% Airbnb Rental Income: $3834 Traditional Rental Income: $2749 Airbnb ROI: -1.37% Traditional ROI: -1.38%
77 Arlington Place New York , NY Presenting a wonderful opportunity in the form of a semi-detached one-family home boasting...	3 beds \| 2 baths \| 1,532 sq.ft.	$548,800	Airbnb cash on cash: 7.42% Traditional cash on cash: 4.14% Airbnb Rental Income: $5856 Traditional Rental Income: $3011 Airbnb ROI: 7.42% Traditional ROI: 4.14%
50 Bradburn Street Rochester , NY Delayed showings/negotiations. Showings to commence on 11/15/24, negotiations begin on 11/...	3 beds \| 1 baths \| 1,772 sq.ft.	$149,900	Airbnb cash on cash: 8.89% Traditional cash on cash: 7.89% Airbnb Rental Income: $2330 Traditional Rental Income: $1610 Airbnb ROI: 8.89% Traditional ROI: 7.89%
1621 70th Street New York , NY Fully detached huge one family home in Bensonhurst. First and second floor a four bedroom ...	4 beds \| 3 baths \| 1,493 sq.ft.	$1,380,000	Airbnb cash on cash: 4.77% Traditional cash on cash: 1.46% Airbnb Rental Income: $10021 Traditional Rental Income: $3917 Airbnb ROI: 4.77% Traditional ROI: 1.46%
7739 Shore Road New York , NY Location! Location! Location!. 1 Family Fully Detached house with a full finished basement...	4 beds \| 3 baths \| 1,144 sq.ft.	$1,398,000	Airbnb cash on cash: 4.46% Traditional cash on cash: 1.09% Airbnb Rental Income: $9950 Traditional Rental Income: $3731 Airbnb ROI: 4.46% Traditional ROI: 1.09%
139-15 83rd Avenue #127 New York , NY Discover the perfect blend of style and convenience in this beautifully updated 1-bedroom ...	1 beds \| 1 baths \| 709 sq.ft.	$199,000	Airbnb cash on cash: 4.4% Traditional cash on cash: 3.27% Airbnb Rental Income: $3197 Traditional Rental Income: $2261 Airbnb ROI: 4.4% Traditional ROI: 3.27%
16 Mickardan Court New York , NY Price Improved and Cheaper Than a Condo! Welcome to this charming semi-detached single-fam...	3 beds \| 3 baths \| 1,200 sq.ft.	$488,888	Airbnb cash on cash: 3.82% Traditional cash on cash: 4.4% Airbnb Rental Income: $3430 Traditional Rental Income: $2933 Airbnb ROI: 3.82% Traditional ROI: 4.4%
20 Lake Road Great Neck , NY Stunning Contemporary Meticulously Designed Home on Lake Garrison. Sprawling 1 Acre Proper...	5 beds \| 3 baths \| N/A	$2,490,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.13% Airbnb Rental Income: $null Traditional Rental Income: $5328 Airbnb ROI: N/A Traditional ROI: -0.13%
86 Virginia Avenue New York , NY LOCATION is Everything!!! Minutes to the Verrazano Bridge and SI Ferry, this recently reno...	5 beds \| 4 baths \| 2,190 sq.ft.	$859,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.71% Airbnb Rental Income: $null Traditional Rental Income: $3655 Airbnb ROI: N/A Traditional ROI: 2.71%
58 Dutchess Avenue New York , NY Welcome to a Timeless Masterpiece: The Colonial Gem You've Been Dreaming Of! Nestled amids...	5 beds \| 3 baths \| 3,322 sq.ft.	$1,750,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.93% Airbnb Rental Income: $null Traditional Rental Income: $4136 Airbnb ROI: N/A Traditional ROI: 0.93%
109-41 164th Street So.Jamaica , NY Welcome to this fully detached single family home located in Jamaica. It has 3 bedroom wit...	3 beds \| 2 baths \| 1,072 sq.ft.	$699,999	Airbnb cash on cash: 0.8% Traditional cash on cash: 3.23% Airbnb Rental Income: $2086 Traditional Rental Income: $3135 Airbnb ROI: 0.8% Traditional ROI: 3.23%
217-14 133rd Road New York , NY REO- HANDYMAN SPECIAL COLONIAL BOASTS 3 BEDROOMS, LR, FDR, EIK, 2 FULL BATHS, AND FULL BAS...	3 beds \| 2 baths \| N/A	$549,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 4.42% Airbnb Rental Income: $4419 Traditional Rental Income: $3388 Airbnb ROI: 4.63% Traditional ROI: 4.42%
151 Ross Avenue New York , NY LOCATION LOCATION! THIS BEAUTIFUL 2 FAMILY OFFERS 3BED 3 BATH IN MAIN UNIT, WITH AN ATTIC ...	5 beds \| 5 baths \| 1,886 sq.ft.	$878,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $4462 Airbnb ROI: N/A Traditional ROI: 3.56%
99-03 207th Street New York , NY	5 beds \| 3 baths \| N/A	$1,450,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.16% Airbnb Rental Income: $null Traditional Rental Income: $4817 Airbnb ROI: N/A Traditional ROI: 2.16%
6015 Independence Avenue New York , NY An oasis of serenity in North Riverdale. Welcome to this tastefully decorated home nestled...	4 beds \| 5 baths \| 2,244 sq.ft.	$1,450,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 2.08% Airbnb Rental Income: $8454 Traditional Rental Income: $5331 Airbnb ROI: 3.21% Traditional ROI: 2.08%

Real Estate investment in Chestertown, NY

There are 2 properties for sale in the city of Chestertown . The median list price in Chestertown is $724,000 and the average price per square foot is $148. In November 2024, the average monthly cash on cash return in Chestertown is 6.00%. The average monthly rental income in Chestertown is $5,127.

Chestertown, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 2 investment properties available for sale in Chestertown.

In 2024, the best neighborhood to buy investment property is Chestertown.

The ROI for Long-Term is higher than the Short-Term in Chestertown with average rental income of $5,127.

Your search for investment property begins and ends here

Investment Property for Sale in Chestertown, NY

6369 State Route 9

Chestertown, NY

4 beds | 7 baths | 6,840 sq.ft.

$749,000

Airbnb cash on cash: 3.47%

Traditional cash on cash: 7.73%

Airbnb Rental Income: $4533

Traditional Rental Income: $6566

Airbnb ROI: 3.47%

Traditional ROI: 7.73%

5 Circle

Chestertown, NY

3 beds | 2 baths | 2,974 sq.ft.

$699,000

Airbnb cash on cash: 2.37%

Traditional cash on cash: 3.73%

Airbnb Rental Income: $3583

Traditional Rental Income: $3688

Airbnb ROI: 2.37%

Traditional ROI: 3.73%

Investment Properties for Sale in Other Cities of New-york

New York , NY

N/A beds | N/A baths | 65,535 sq.ft.

$27,000,000

Airbnb cash on cash: -1.37%

Traditional cash on cash: -1.38%

Airbnb Rental Income: $3834

Traditional Rental Income: $2749

Airbnb ROI: -1.37%

Traditional ROI: -1.38%

New York , NY

3 beds | 2 baths | 1,532 sq.ft.

$548,800

Airbnb cash on cash: 7.42%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $5856

Traditional Rental Income: $3011

Airbnb ROI: 7.42%

Traditional ROI: 4.14%

Rochester , NY

3 beds | 1 baths | 1,772 sq.ft.

$149,900

Airbnb cash on cash: 8.89%

Traditional cash on cash: 7.89%

Airbnb Rental Income: $2330

Traditional Rental Income: $1610

Airbnb ROI: 8.89%

Traditional ROI: 7.89%

New York , NY

4 beds | 3 baths | 1,493 sq.ft.

$1,380,000

Airbnb cash on cash: 4.77%

Traditional cash on cash: 1.46%

Airbnb Rental Income: $10021

Traditional Rental Income: $3917

Airbnb ROI: 4.77%

Traditional ROI: 1.46%

New York , NY

4 beds | 3 baths | 1,144 sq.ft.

$1,398,000

Airbnb cash on cash: 4.46%

Traditional cash on cash: 1.09%

Airbnb Rental Income: $9950

Traditional Rental Income: $3731

Airbnb ROI: 4.46%

Traditional ROI: 1.09%

New York , NY

1 beds | 1 baths | 709 sq.ft.

$199,000

Airbnb cash on cash: 4.4%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $3197

Traditional Rental Income: $2261

Airbnb ROI: 4.4%

Traditional ROI: 3.27%

New York , NY

3 beds | 3 baths | 1,200 sq.ft.

$488,888

Airbnb cash on cash: 3.82%