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.

Multi Family for Sale in Chester, NY

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

Showing 1 Multi Family 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
206 Greycourt Rd Chester, NY 206 Greycourt Rd, Chester, NY 10918 \| Multi Family	N/A beds \| N/A baths \| 4,032 sq.ft.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.7% Airbnb Rental Income: $null Traditional Rental Income: $1220 Airbnb ROI: N/A Traditional ROI: -1.7%
Other Investment Properties for Sale in Chester
151 Laroe Road Chester , NY What a remarkable property in the town of Chester, NY-a highly sought after town in the so...	3 beds \| 2 baths \| 1,177 sq.ft.	$430,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 3.56% Airbnb Rental Income: $2875 Traditional Rental Income: $2684 Airbnb ROI: 2.38% Traditional ROI: 3.56%
19 Greentree Lane Chester , NY Set behind a gated entrance with a private guard house and unfolding across 8.4 private ac...	4 beds \| 4 baths \| 7,750 sq.ft.	$3,400,000	Airbnb cash on cash: -0.96% Traditional cash on cash: -0.38% Airbnb Rental Income: $3903 Traditional Rental Income: $4896 Airbnb ROI: -0.96% Traditional ROI: -0.38%
35 Maple Ave Chester , NY Make this Home Yours "HOME SWEET HOME" Your Search Ends Here!! This Updated 3 Bedroom 3 Fu...	3 beds \| 3 baths \| 2,032 sq.ft.	$529,900	Airbnb cash on cash: 1.14% Traditional cash on cash: 3.31% Airbnb Rental Income: $2875 Traditional Rental Income: $3279 Airbnb ROI: 1.14% Traditional ROI: 3.31%
1311 Whispering Hills Chester , NY AO Experience Elevated Living: Your Private Hudson Valley Retreat at 1311 Whispering Hills...	3 beds \| 2 baths \| 1,316 sq.ft.	$344,900	Airbnb cash on cash: 2.15% Traditional cash on cash: 3.59% Airbnb Rental Income: $2875 Traditional Rental Income: $2673 Airbnb ROI: 2.15% Traditional ROI: 3.59%
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: 0.88% Traditional cash on cash: 2.7% Airbnb Rental Income: $3903 Traditional Rental Income: $4501 Airbnb ROI: 0.88% 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.	$400,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 3.27% Airbnb Rental Income: $2875 Traditional Rental Income: $2578 Airbnb ROI: 2.28% Traditional ROI: 3.27%
208 Glenmere Rd Chester , NY Here's your chance to own this renovated, country cottage located on a beautiful, pictures...	5 beds \| 2 baths \| 1,815 sq.ft.	$550,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 4.19% Airbnb Rental Income: $3246 Traditional Rental Income: $3518 Airbnb ROI: 2.24% Traditional ROI: 4.19%
19 High St Chester , NY Own a true piece of American history with the iconic Hambletonian House, a one-of-a-kind V...	9 beds \| 6 baths \| 4,965 sq.ft.	$1,195,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 0.55% Airbnb Rental Income: $3246 Traditional Rental Income: $3603 Airbnb ROI: -0.43% Traditional ROI: 0.55%
487 Black Meadow Rd Chester , NY Beautiful colonial farm house. Over 4,000 square feet. Large, foyer. Spacious living room ...	6 beds \| 3 baths \| 4,204 sq.ft.	$725,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 0.37% Airbnb Rental Income: $3246 Traditional Rental Income: $2174 Airbnb ROI: 0.88% Traditional ROI: 0.37%
2 Garnett Hill Rd Chester , NY Located in the highly desired street Garnet Hill which backs up to Primrose rd. Sits a Stu...	5 beds \| 2 baths \| 4,772 sq.ft.	$999,999	Airbnb cash on cash: -0.44% Traditional cash on cash: 1.41% Airbnb Rental Income: $3246 Traditional Rental Income: $4236 Airbnb ROI: -0.44% Traditional ROI: 1.41%
4 Greycourt Rd Chester , NY Magnificent sprawling ranch situated on a park like setting with 2.80 acres with mature la...	3 beds \| 1 baths \| 2,136 sq.ft.	$640,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 2.39% Airbnb Rental Income: $2875 Traditional Rental Income: $3141 Airbnb ROI: 0.83% Traditional ROI: 2.39%
16 Lori Lane Chester , NY Welcome to Chester, NY, a resort-style luxury colonial set on a private 1.1-acre cul-de-sa...	4 beds \| 5 baths \| 4,624 sq.ft.	$1,159,900	Airbnb cash on cash: -0.55% Traditional cash on cash: 2.08% Airbnb Rental Income: $3903 Traditional Rental Income: $5897 Airbnb ROI: -0.55% Traditional ROI: 2.08%
2 Pine Hill Rd Chester , NY Listed on the National Register of Historic Places in the Sugar Loaf Historic District, th...	3 beds \| 2 baths \| 2,302 sq.ft.	$875,000	Airbnb cash on cash: 0% Traditional cash on cash: 1.88% Airbnb Rental Income: $2875 Traditional Rental Income: $3733 Airbnb ROI: 0% Traditional ROI: 1.88%
20 Goshen Road Chester , NY THE ULTIMATE HUDSON VALLEY LEGACY ESTATE \| 53 ACRES OF UNMATCHED POTENTIAL Rarely does a p...	4 beds \| 3 baths \| 3,348 sq.ft.	$1,725,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 0.19% Airbnb Rental Income: $3903 Traditional Rental Income: $4136 Airbnb ROI: -0.48% Traditional ROI: 0.19%
4 Debbie Court Chester , NY Welcome to this exceptional private retreat nestled on beautifully landscaped grounds in d...	5 beds \| 6 baths \| 5,403 sq.ft.	$799,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 5.98% Airbnb Rental Income: $3246 Traditional Rental Income: $7227 Airbnb ROI: -0.35% Traditional ROI: 5.98%

Your search for investment property begins and ends here

Multi Family for Sale in Chester, NY

206 Greycourt Rd

Chester, NY

N/A beds | N/A baths | 4,032 sq.ft.

$1,200,000

Airbnb cash on cash: N/A

Traditional cash on cash: -1.7%

Airbnb Rental Income: $null

Traditional Rental Income: $1220

Airbnb ROI: N/A

Traditional ROI: -1.7%

Other Investment Properties for Sale in Chester

Chester , NY

3 beds | 2 baths | 1,177 sq.ft.

$430,000

Airbnb cash on cash: 2.38%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $2875

Traditional Rental Income: $2684

Airbnb ROI: 2.38%

Traditional ROI: 3.56%

Chester , NY

4 beds | 4 baths | 7,750 sq.ft.

$3,400,000

Airbnb cash on cash: -0.96%

Traditional cash on cash: -0.38%

Airbnb Rental Income: $3903

Traditional Rental Income: $4896

Airbnb ROI: -0.96%

Traditional ROI: -0.38%

Chester , NY

3 beds | 3 baths | 2,032 sq.ft.

$529,900

Airbnb cash on cash: 1.14%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $2875

Traditional Rental Income: $3279

Airbnb ROI: 1.14%

Traditional ROI: 3.31%

Chester , NY

3 beds | 2 baths | 1,316 sq.ft.

$344,900

Airbnb cash on cash: 2.15%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $2875

Traditional Rental Income: $2673

Airbnb ROI: 2.15%

Traditional ROI: 3.59%

Chester , NY

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

$849,900

Airbnb cash on cash: 0.88%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $3903

Traditional Rental Income: $4501

Airbnb ROI: 0.88%

Traditional ROI: 2.7%

Chester , NY

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

$400,000

Airbnb cash on cash: 2.28%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $2875

Traditional Rental Income: $2578

Airbnb ROI: 2.28%

Traditional ROI: 3.27%

Chester , NY

5 beds | 2 baths | 1,815 sq.ft.

$550,000

Airbnb cash on cash: 2.24%

Traditional cash on cash: 4.19%

Airbnb Rental Income: $3246

Traditional Rental Income: $3518

Airbnb ROI: 2.24%

Traditional ROI: 4.19%

Chester , NY

9 beds | 6 baths | 4,965 sq.ft.

$1,195,000

Airbnb cash on cash: -0.43%

Traditional cash on cash: 0.55%