Real Estate Investment Properties for Sale in Chester, NY

Looking for investment property in Chester, NY with high ROI ?

Explore a variety of short-term homes & houses in Chester, NY. Invest wisely with VRBO & Chester, NY Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Condos for Sale in Chester, NY

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

Showing 4 Condo 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
2915 Whispering Hills Chester, NY Welcome to your next home in the highly desirable Whispering Hills community! Completely r...	3 beds \| 3 baths \| 1,331 sq.ft.	$369,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 3.69% Airbnb Rental Income: $2220 Traditional Rental Income: $2795 Airbnb ROI: 0.42% Traditional ROI: 3.69%
2912 Whispering Hills Chester, NY Welcome home to this beautifully renovated 2 bedroom, 1 bathroom condo located in the desi...	2 beds \| 1 baths \| 1,084 sq.ft.	$304,900	Airbnb cash on cash: 0.03% Traditional cash on cash: 4.82% Airbnb Rental Income: $1165 Traditional Rental Income: $2155 Airbnb ROI: 0.03% Traditional ROI: 4.82%
80 Pewter Circle Chester, NY Welcome to the Villas at Sugar Loaf - an unbeatable location that rarely sees homes come o...	3 beds \| 3 baths \| 1,946 sq.ft.	$534,900	Airbnb cash on cash: -0.02% Traditional cash on cash: 3.22% Airbnb Rental Income: $2220 Traditional Rental Income: $3279 Airbnb ROI: -0.02% Traditional ROI: 3.22%
2317 Whispering Hills Chester, NY Welcome to your new home at 2317 Whispering Hills, Chester, NY 10918, where resort-style l...	2 beds \| 2 baths \| 1,072 sq.ft.	$299,999	Airbnb cash on cash: -1.55% Traditional cash on cash: 4.32% Airbnb Rental Income: $1165 Traditional Rental Income: $2440 Airbnb ROI: -1.55% Traditional ROI: 4.32%
Other Investment Properties for Sale in Chester
7 Park Place Chester , NY Welcome to your private, wooded oasis! This charming home perfectly blends convenience wit...	4 beds \| 4 baths \| 2,780 sq.ft.	$740,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 2.95% Airbnb Rental Income: $2830 Traditional Rental Income: $4642 Airbnb ROI: -0.64% Traditional ROI: 2.95%
32 Mountainside Drive Chester , NY A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-...	4 beds \| 3 baths \| 2,603 sq.ft.	$849,900	Airbnb cash on cash: -0.25% Traditional cash on cash: 2.7% Airbnb Rental Income: $2830 Traditional Rental Income: $4501 Airbnb ROI: -0.25% Traditional ROI: 2.7%
33 Meadow Avenue Chester , NY One floor living at it best! Walk out your front door, sit on your rocking chair front por...	3 beds \| 1 baths \| 1,561 sq.ft.	$430,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 2.98% Airbnb Rental Income: $2220 Traditional Rental Income: $2578 Airbnb ROI: 0.7% Traditional ROI: 2.98%
65 Oxford Springs Road Chester , NY Welcome to 65 Oxford Springs Road, Chester, NY a custom-built Country Contemporary set on ...	5 beds \| 4 baths \| 3,617 sq.ft.	$650,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 3.29% Airbnb Rental Income: $3006 Traditional Rental Income: $4293 Airbnb ROI: 0.03% Traditional ROI: 3.29%
18 Oakland Avenue Chester , NY This is a "Neat as a pin" ranch in the Village of Chester. The kitchen has many updated ap...	2 beds \| 1 baths \| 1,084 sq.ft.	$369,900	Airbnb cash on cash: -1.4% Traditional cash on cash: 3.04% Airbnb Rental Income: $1165 Traditional Rental Income: $2324 Airbnb ROI: -1.4% Traditional ROI: 3.04%
278 Gibson Hill Road Chester , NY FULLY AVAILABLE. Amazing property, offers something for everyone! Gorgeously restored 3,97...	4 beds \| 3 baths \| 3,977 sq.ft.	$722,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 2.4% Airbnb Rental Income: $2830 Traditional Rental Income: $3683 Airbnb ROI: 0.15% Traditional ROI: 2.4%
16 Lori Lane Chester , NY Indulge in luxury living at this resort-style residence in Chester, NY, within the prestig...	4 beds \| 5 baths \| 4,624 sq.ft.	$1,160,000	Airbnb cash on cash: -1.38% Traditional cash on cash: 2.08% Airbnb Rental Income: $2830 Traditional Rental Income: $5897 Airbnb ROI: -1.38% Traditional ROI: 2.08%
70 Main Street Chester , NY Discover the perfect blend of versatility and charm with this exceptional property. The ma...	4 beds \| 3 baths \| 1,357 sq.ft.	$475,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 4.16% Airbnb Rental Income: $2830 Traditional Rental Income: $3391 Airbnb ROI: 1.41% Traditional ROI: 4.16%
206 Greycourt Road #190 Chester , NY Endless Opportunities Await on This Rare 3.2-Acre Property! ZONED COMMMERCIAL INDUST...	N/A beds \| N/A baths \| N/A	$1,500,000	Airbnb cash on cash: -0.41% Traditional cash on cash: -0.74% Airbnb Rental Income: $2830 Traditional Rental Income: $1715 Airbnb ROI: -0.41% Traditional ROI: -0.74%
2 Pine Hill Road Chester , NY Listed on the National Register of Historic Places in the Sugar Loaf Historic District, th...	3 beds \| 3 baths \| 2,302 sq.ft.	$875,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 1.88% Airbnb Rental Income: $2220 Traditional Rental Income: $3733 Airbnb ROI: -0.67% Traditional ROI: 1.88%
5 Gabriels Drive Chester , NY Exquisite Colonial Estate: Timeless Grandeur Meets Modern Luxury Nestled gracefully on a ...	4 beds \| 3 baths \| 2,722 sq.ft.	$1,099,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 1.17% Airbnb Rental Income: $2830 Traditional Rental Income: $3988 Airbnb ROI: -0.61% Traditional ROI: 1.17%
37-39 Main Street Chester , NY Prime Investment Opportunity in the Heart of Chester Village â 37-39 Main Street & 9 Ban...	4 beds \| 4 baths \| 7,308 sq.ft.	$1,498,888	Airbnb cash on cash: -0.31% Traditional cash on cash: 1.53% Airbnb Rental Income: $2830 Traditional Rental Income: $4729 Airbnb ROI: -0.31% Traditional ROI: 1.53%
20 Goshen Road Chester , NY Discover a rare opportunity to own a one-of-a-kind estate set on 53 sprawling acres in the...	4 beds \| 3 baths \| 3,348 sq.ft.	$1,775,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 0.15% Airbnb Rental Income: $2830 Traditional Rental Income: $4136 Airbnb ROI: -1.04% Traditional ROI: 0.15%
507 Bull Mill Road Chester , NY Welcome to this beautifully maintained colonial with a charming wrap-around front porch, s...	5 beds \| 3 baths \| 3,115 sq.ft.	$674,999	Airbnb cash on cash: -0.3% Traditional cash on cash: 2.44% Airbnb Rental Income: $3006 Traditional Rental Income: $4038 Airbnb ROI: -0.3% Traditional ROI: 2.44%
34 Mountainside Drive Chester , NY ONE LEVEL LIVING/ EASY COMMUTE- with additional space upstairs and down! ... Don't miss th...	4 beds \| 3 baths \| 1,867 sq.ft.	$699,990	Airbnb cash on cash: 0.34% Traditional cash on cash: 2.87% Airbnb Rental Income: $2830 Traditional Rental Income: $3820 Airbnb ROI: 0.34% Traditional ROI: 2.87%

Your search for investment property begins and ends here

Condos for Sale in Chester, NY

2915 Whispering Hills

Chester, NY

3 beds | 3 baths | 1,331 sq.ft.

$369,000

Airbnb cash on cash: 0.42%

Traditional cash on cash: 3.69%

Airbnb Rental Income: $2220

Traditional Rental Income: $2795

Airbnb ROI: 0.42%

Traditional ROI: 3.69%

2912 Whispering Hills

Chester, NY

2 beds | 1 baths | 1,084 sq.ft.

$304,900

Airbnb cash on cash: 0.03%

Traditional cash on cash: 4.82%

Airbnb Rental Income: $1165

Traditional Rental Income: $2155

Airbnb ROI: 0.03%

Traditional ROI: 4.82%

80 Pewter Circle

Chester, NY

3 beds | 3 baths | 1,946 sq.ft.

$534,900

Airbnb cash on cash: -0.02%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $2220

Traditional Rental Income: $3279

Airbnb ROI: -0.02%

Traditional ROI: 3.22%

2317 Whispering Hills

Chester, NY

2 beds | 2 baths | 1,072 sq.ft.

$299,999

Airbnb cash on cash: -1.55%

Traditional cash on cash: 4.32%

Airbnb Rental Income: $1165

Traditional Rental Income: $2440

Airbnb ROI: -1.55%

Traditional ROI: 4.32%

Other Investment Properties for Sale in Chester

Chester , NY

4 beds | 4 baths | 2,780 sq.ft.

$740,000

Airbnb cash on cash: -0.64%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $2830

Traditional Rental Income: $4642

Airbnb ROI: -0.64%

Traditional ROI: 2.95%

Chester , NY

4 beds | 3 baths | 2,603 sq.ft.

$849,900

Airbnb cash on cash: -0.25%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $2830

Traditional Rental Income: $4501

Airbnb ROI: -0.25%

Traditional ROI: 2.7%

Chester , NY

3 beds | 1 baths | 1,561 sq.ft.

$430,000

Airbnb cash on cash: 0.7%

Traditional cash on cash: 2.98%

Airbnb Rental Income: $2220

Traditional Rental Income: $2578

Airbnb ROI: 0.7%

Traditional ROI: 2.98%

Chester , NY

5 beds | 4 baths | 3,617 sq.ft.

$650,000

Airbnb cash on cash: 0.03%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $3006

Traditional Rental Income: $4293

Airbnb ROI: 0.03%

Traditional ROI: 3.29%

Chester , NY

2 beds | 1 baths | 1,084 sq.ft.