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 2 Multi Family listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
37-39 Main St 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%
Other Investment Properties for Sale in Chester
7 Park Pl Chester , NY Welcome to your private, wooded oasis! This charming home perfectly blends convenience wit...	4 beds \| 3 baths \| 2,780 sq.ft.	$730,000	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 Dr Chester , NY A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-...	4 beds \| 2 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 Ave 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: 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 Rd Chester , NY Welcome to 65 Oxford Springs Road, Chester, NY a custom-built Country Contemporary set on ...	5 beds \| 3 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%
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 St Chester , NY Discover the perfect blend of versatility and charm with this exceptional property. The ma...	4 beds \| 2 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%
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: -0.67% Traditional cash on cash: 1.88% Airbnb Rental Income: $2220 Traditional Rental Income: $3733 Airbnb ROI: -0.67% Traditional ROI: 1.88%
5 Gabriels Dr Chester , NY Exquisite 4 bedroom 3 bath colonial , timeless grandeur meets modern luxury nestled gracef...	4 beds \| 2 baths \| 2,722 sq.ft.	$899,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 1.59% Airbnb Rental Income: $2830 Traditional Rental Income: $3988 Airbnb ROI: -0.59% Traditional ROI: 1.59%
20 Goshen Rd Chester , NY Discover a rare opportunity to own a one-of-a-kind estate set on 53 sprawling acres in the...	4 beds \| 2 baths \| 3,348 sq.ft.	$1,725,000	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%
34 Mountainside Dr 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%
11 Lakeview Drive Chester , NY Split-level spacious home in desirable Chester neighborhood within Warwick Valley School D...	4 beds \| 3 baths \| 1,848 sq.ft.	$539,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 4.31% Airbnb Rental Income: $2830 Traditional Rental Income: $3775 Airbnb ROI: 1.12% Traditional ROI: 4.31%
220 Oxford Rd Chester , NY Step into this newly renovated contemporary ranch, where comfort meets value on 6.3 acres ...	N/A beds \| N/A baths \| 3,472 sq.ft.	$350,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 3.74% Airbnb Rental Income: $2830 Traditional Rental Income: $4853 Airbnb ROI: -0.37% Traditional ROI: 3.74%
2948 State Route 94 Chester , NY Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, th...	4 beds \| 2 baths \| 3,866 sq.ft.	$1,395,000	Airbnb cash on cash: -1.63% Traditional cash on cash: -0.05% Airbnb Rental Income: $2830 Traditional Rental Income: $4211 Airbnb ROI: -1.63% Traditional ROI: -0.05%

Your search for investment property begins and ends here

Multi Family for Sale in Chester, NY

206 Greycourt Road #190

Chester, NY

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%

37-39 Main St

Chester, NY

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%

Other Investment Properties for Sale in Chester

Chester , NY

4 beds | 3 baths | 2,780 sq.ft.

$730,000

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 | 2 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.

$400,000

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 | 3 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

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%

Chester , NY

4 beds | 2 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%

Chester , NY

3 beds | 2 baths | 2,302 sq.ft.

$875,000

Airbnb cash on cash: -0.67%