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.

Investment Property for Sale in Chester, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
985 Craigville Rd Chester, NY Through the Stone Pillars into your circular driveway and you are Welcomed to this Prestig...	4 beds \| 3 baths \| 3,100 sq.ft.	$750,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 2.48% Airbnb Rental Income: $3425 Traditional Rental Income: $3820 Airbnb ROI: 0.83% Traditional ROI: 2.48%
24 Boville Ct Chester, NY Welcome to 24 Boville Court, a beautifully situated home tucked away on a quiet cul-de-sac...	4 beds \| 2 baths \| 2,236 sq.ft.	$849,999	Airbnb cash on cash: 0.37% Traditional cash on cash: 1.96% Airbnb Rental Income: $3425 Traditional Rental Income: $3925 Airbnb ROI: 0.37% Traditional ROI: 1.96%
34 Boville Ct Chester, NY New construction home being built by New Gen Construction in Chesterdale Estates a communi...	4 beds \| 2 baths \| 2,707 sq.ft.	$839,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 1.68% Airbnb Rental Income: $3425 Traditional Rental Income: $3520 Airbnb ROI: 0.58% Traditional ROI: 1.68%
241 Meadow Ave Chester, NY Charming Farmhouse Colonial with stunning views of the countryside mountains. Beautiful w...	4 beds \| 1 baths \| 1,560 sq.ft.	$349,999	Airbnb cash on cash: 4.81% Traditional cash on cash: 5.21% Airbnb Rental Income: $3425 Traditional Rental Income: $2796 Airbnb ROI: 4.81% Traditional ROI: 5.21%
19 Greentree Ln 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: -1.09% Traditional cash on cash: -0.38% Airbnb Rental Income: $3425 Traditional Rental Income: $4896 Airbnb ROI: -1.09% Traditional ROI: -0.38%
101 Beverly Rd Chester, NY Homepath property for sale! Large colonial tucked away in scenic Chester waiting for your ...	4 beds \| 2 baths \| 3,764 sq.ft.	$879,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 1.2% Airbnb Rental Income: $3425 Traditional Rental Income: $3280 Airbnb ROI: 0.45% Traditional ROI: 1.2%
166 Bull Mill Rd Chester, NY Refreshingly Different! 1860's Country Farmhouse! NOTE: THIS IS A "PERIOD" HOUSE with rus...	2 beds \| 1 baths \| 1,004 sq.ft.	$289,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 3.16% Airbnb Rental Income: $2461 Traditional Rental Income: $1982 Airbnb ROI: 2.72% Traditional ROI: 3.16%
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.	$489,900	Airbnb cash on cash: 1.17% Traditional cash on cash: 3.66% Airbnb Rental Income: $2797 Traditional Rental Income: $3279 Airbnb ROI: 1.17% Traditional ROI: 3.66%
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.	$370,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 3.54% Airbnb Rental Income: $2797 Traditional Rental Income: $2578 Airbnb ROI: 2.29% Traditional ROI: 3.54%
424 Laroe Rd Chester, NY Great home, beautiful views, close to highway's, close to Woodbury Common Premium outlets,...	4 beds \| 3 baths \| 2,316 sq.ft.	$634,999	Airbnb cash on cash: 1.35% Traditional cash on cash: 2.86% Airbnb Rental Income: $3425 Traditional Rental Income: $3559 Airbnb ROI: 1.35% Traditional ROI: 2.86%
3 Grand View Ter Chester, NY Beautiful large home. Perfect for entertaining. Kitchen appliances are less than a year ol...	6 beds \| 3 baths \| 3,066 sq.ft.	$749,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 2.33% Airbnb Rental Income: $3239 Traditional Rental Income: $3928 Airbnb ROI: 0.29% Traditional ROI: 2.33%
121 Conklingtown Rd Chester, NY Rare opportunity to live in a prime location just minutes away from all local amenities! ...	4 beds \| 2 baths \| 2,599 sq.ft.	$749,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 2.35% Airbnb Rental Income: $3425 Traditional Rental Income: $3744 Airbnb ROI: 0.81% Traditional ROI: 2.35%
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.	$1,145,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 0.62% Airbnb Rental Income: $3239 Traditional Rental Income: $3603 Airbnb ROI: -0.41% Traditional ROI: 0.62%
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.	$699,995	Airbnb cash on cash: 1% Traditional cash on cash: 0.48% Airbnb Rental Income: $3239 Traditional Rental Income: $2174 Airbnb ROI: 1% Traditional ROI: 0.48%
50 Hambletonian Ave Chester, NY Welcome to the Town of Chester! WOW!! Nothing to do but unpack into this beautifully renov...	3 beds \| 2 baths \| 1,583 sq.ft.	$550,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 2.69% Airbnb Rental Income: $2797 Traditional Rental Income: $3083 Airbnb ROI: 0.86% Traditional ROI: 2.69%
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: $3239 Traditional Rental Income: $4236 Airbnb ROI: -0.44% Traditional ROI: 1.41%
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 \| 3,463 sq.ft.	$699,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 3% Airbnb Rental Income: $3239 Traditional Rental Income: $4293 Airbnb ROI: 0.26% Traditional ROI: 3%
412 Laroe Rd Chester, NY This extraordinarily charming totally updated high ranch is sitting on 2.4 private landsc...	3 beds \| 2 baths \| 1,848 sq.ft.	$605,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 2.66% Airbnb Rental Income: $2797 Traditional Rental Income: $3181 Airbnb ROI: 0.82% Traditional ROI: 2.66%
16 Lori Ln Chester, NY Welcome to Chester, NY, a resort-style luxury colonial set on a private 1.1-acre cul-de-sa...	4 beds \| 3 baths \| 4,624 sq.ft.	$1,139,900	Airbnb cash on cash: -0.92% Traditional cash on cash: 2.13% Airbnb Rental Income: $3425 Traditional Rental Income: $5897 Airbnb ROI: -0.92% Traditional ROI: 2.13%
70 Main St Chester, NY Discover the perfect blend of versatility and charm with this exceptional property. The ma...	3 beds \| 1 baths \| 1,357 sq.ft.	$469,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 4.22% Airbnb Rental Income: $2797 Traditional Rental Income: $3391 Airbnb ROI: 1.37% Traditional ROI: 4.22%
49 Stone Mountain Trl Chester, NY Stunning curb appeal. Unrivaled privacy. This 3-story, 3,650+ sq. ft. contemporary colonia...	4 beds \| 2 baths \| 3,656 sq.ft.	$875,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 2.14% Airbnb Rental Income: $3425 Traditional Rental Income: $4114 Airbnb ROI: 0.36% Traditional ROI: 2.14%
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: -0.08% Traditional cash on cash: 1.88% Airbnb Rental Income: $2797 Traditional Rental Income: $3733 Airbnb ROI: -0.08% Traditional ROI: 1.88%
20 Goshen Rd Chester, NY THE ULTIMATE HUDSON VALLEY LEGACY ESTATE \| 53 ACRES OF UNMATCHED POTENTIAL Rarely does a p...	4 beds \| 2 baths \| 3,348 sq.ft.	$1,725,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 0.19% Airbnb Rental Income: $3425 Traditional Rental Income: $4136 Airbnb ROI: -0.73% Traditional ROI: 0.19%
220 Oxford Rd Chester, NY Step into this newly renovated contemporary ranch, where comfort meets value on 6.3 acres ...	3 beds \| 3 baths \| 3,535 sq.ft.	$894,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 2.72% Airbnb Rental Income: $2797 Traditional Rental Income: $4853 Airbnb ROI: -0.54% Traditional ROI: 2.72%
2113 Whispering Hls Chester, NY Welcome Home! 2 Bedrooms 1 Bathroom move in ready end unit. Recently renovated including a...	2 beds \| 1 baths \| 1,084 sq.ft.	$275,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 2.12% Airbnb Rental Income: $2461 Traditional Rental Income: $1992 Airbnb ROI: 1.61% Traditional ROI: 2.12%
69 Cedar Pond Ln Chester, NY 69 Cedar Pond Ln, Chester, NY 10918 \| Single Family Residential	6 beds \| 7 baths \| 7,034 sq.ft.	$1,599,999	Airbnb cash on cash: -1.17% Traditional cash on cash: 1.46% Airbnb Rental Income: $3239 Traditional Rental Income: $6617 Airbnb ROI: -1.17% Traditional ROI: 1.46%
Odyssey Dr Chester, NY Odyssey Dr, Chester, NY 10918 \| Other	N/A beds \| N/A baths \| N/A	$350,000	Airbnb cash on cash: -6.27% Traditional cash on cash: -4.21% Airbnb Rental Income: $796 Traditional Rental Income: $1152 Airbnb ROI: -6.27% Traditional ROI: -4.21%
1367 Kings Hwy Chester, NY Historic Colonial Era Home in the Heart of Sugar Loaf, NY Located just 60 minutes from NYC...	3 beds \| 1 baths \| 1,728 sq.ft.	$440,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 4.09% Airbnb Rental Income: $2797 Traditional Rental Income: $2908 Airbnb ROI: 2.23% Traditional ROI: 4.09%
145 Kings Highway Byp Chester, NY Set gracefully on 3.8 private acres within the highly coveted Warwick School District, thi...	4 beds \| 4 baths \| 4,508 sq.ft.	$1,299,900	Airbnb cash on cash: -0.32% Traditional cash on cash: 1.51% Airbnb Rental Income: $3425 Traditional Rental Income: $4877 Airbnb ROI: -0.32% Traditional ROI: 1.51%
12 Damian Ct Chester, NY 12 Damian Ct, Chester, NY 10918 \| Single Family Residential	5 beds \| 4 baths \| 3,136 sq.ft.	$949,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 2.1% Airbnb Rental Income: $3239 Traditional Rental Income: $4341 Airbnb ROI: 0.03% Traditional ROI: 2.1%
558 Pine Hill Rd Chester, NY 558 Pine Hill Rd, Chester, NY 10918 \| Single Family Residential	4 beds \| 2 baths \| 3,120 sq.ft.	$599,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 3.63% Airbnb Rental Income: $3425 Traditional Rental Income: $3640 Airbnb ROI: 1.89% Traditional ROI: 3.63%
1005 Whispering Hls Chester, NY 1005 Whispering Hls, Chester, NY 10918 \| Condo/Coop	2 beds \| 1 baths \| 1,053 sq.ft.	$290,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 2.03% Airbnb Rental Income: $2461 Traditional Rental Income: $1801 Airbnb ROI: 2.25% Traditional ROI: 2.03%
552 Pine Hill Rd Chester, NY 552 Pine Hill Rd, Chester, NY 10918 \| Other	N/A beds \| N/A baths \| N/A	$299,000	Airbnb cash on cash: -1.35% Traditional cash on cash: 1.15% Airbnb Rental Income: $796 Traditional Rental Income: $1176 Airbnb ROI: -1.35% Traditional ROI: 1.15%
1414 Kings Hwy Chester, NY Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combin...	4 beds \| 2 baths \| 3,200 sq.ft.	$879,900	Airbnb cash on cash: 0.43% Traditional cash on cash: 2.12% Airbnb Rental Income: $3425 Traditional Rental Income: $4051 Airbnb ROI: 0.43% Traditional ROI: 2.12%
5 N Hudson St Chester, NY 3 bedroom 2 bath contemporary home tucked away on a quiet street. Modern renovation alread...	3 beds \| 2 baths \| 2,688 sq.ft.	$500,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 2.86% Airbnb Rental Income: $2797 Traditional Rental Income: $3127 Airbnb ROI: 0.75% Traditional ROI: 2.86%
90 Pewter Cir Chester, NY This beautiful custom home is planned to be built in the highly sought-after Sugar Loaf ar...	4 beds \| 2 baths \| 2,250 sq.ft.	$759,900	Airbnb cash on cash: 1.54% Traditional cash on cash: 3.04% Airbnb Rental Income: $3425 Traditional Rental Income: $3727 Airbnb ROI: 1.54% Traditional ROI: 3.04%
2 Primrose Ln Chester, NY 2 Primrose Ln, Chester, NY 10918 \| Single Family Residential	4 beds \| 3 baths \| 2,370 sq.ft.	$849,900	Airbnb cash on cash: 0.54% Traditional cash on cash: 1.98% Airbnb Rental Income: $3425 Traditional Rental Income: $3801 Airbnb ROI: 0.54% Traditional ROI: 1.98%
58 Nancy Ln Chester, NY 58 Nancy Ln, Chester, NY 10918 \| Single Family Residential	4 beds \| 2 baths \| 2,718 sq.ft.	$744,999	Airbnb cash on cash: 1% Traditional cash on cash: 1.38% Airbnb Rental Income: $3425 Traditional Rental Income: $2931 Airbnb ROI: 1% Traditional ROI: 1.38%
60 Whitetail Run Chester, NY Beautifully maintained Colonial set on a picturesque and private property offering the per...	4 beds \| 2 baths \| 2,588 sq.ft.	$900,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 1.21% Airbnb Rental Income: $3425 Traditional Rental Income: $3637 Airbnb ROI: 0.05% Traditional ROI: 1.21%
63 Hubshop Rd Chester, NY Nestled on a quiet road off the beaten path, this serene 4-bedroom, 2.5-bathroom Colonial ...	4 beds \| 2 baths \| 2,060 sq.ft.	$459,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 4.71% Airbnb Rental Income: $3425 Traditional Rental Income: $3669 Airbnb ROI: 2.38% Traditional ROI: 4.71%

Real Estate investment in Chester, NY

There are 110 properties for sale in the city of Chester . The median list price in Chester is $350,790 and the average price per square foot is $175. In October 2026, the average monthly cash on cash return in Chester is 2.00%. The average monthly rental income in Chester is $3,205.

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

There are 110 investment properties available for sale in Chester.

In 2026, the best neighborhood to buy investment property is Chester.

The ROI for Long-Term is higher than the Short-Term in Chester with average rental income of $3,205.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, NY

985 Craigville Rd

Chester, NY

4 beds | 3 baths | 3,100 sq.ft.

$750,000

Airbnb cash on cash: 0.83%

Traditional cash on cash: 2.48%

Airbnb Rental Income: $3425

Traditional Rental Income: $3820

Airbnb ROI: 0.83%

Traditional ROI: 2.48%

24 Boville Ct

Chester, NY

4 beds | 2 baths | 2,236 sq.ft.

$849,999

Airbnb cash on cash: 0.37%

Traditional cash on cash: 1.96%

Airbnb Rental Income: $3425

Traditional Rental Income: $3925

Airbnb ROI: 0.37%

Traditional ROI: 1.96%

34 Boville Ct

Chester, NY

4 beds | 2 baths | 2,707 sq.ft.

$839,000

Airbnb cash on cash: 0.58%

Traditional cash on cash: 1.68%

Airbnb Rental Income: $3425

Traditional Rental Income: $3520

Airbnb ROI: 0.58%

Traditional ROI: 1.68%

241 Meadow Ave

Chester, NY

4 beds | 1 baths | 1,560 sq.ft.

$349,999

Airbnb cash on cash: 4.81%

Traditional cash on cash: 5.21%

Airbnb Rental Income: $3425

Traditional Rental Income: $2796

Airbnb ROI: 4.81%

Traditional ROI: 5.21%

19 Greentree Ln

Chester, NY

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

$3,400,000

Airbnb cash on cash: -1.09%

Traditional cash on cash: -0.38%

Airbnb Rental Income: $3425

Traditional Rental Income: $4896

Airbnb ROI: -1.09%

Traditional ROI: -0.38%

101 Beverly Rd

Chester, NY

4 beds | 2 baths | 3,764 sq.ft.

$879,000

Airbnb cash on cash: 0.45%

Traditional cash on cash: 1.2%

Airbnb Rental Income: $3425

Traditional Rental Income: $3280

Airbnb ROI: 0.45%

Traditional ROI: 1.2%

166 Bull Mill Rd

Chester, NY

2 beds | 1 baths | 1,004 sq.ft.

$289,000

Airbnb cash on cash: 2.72%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $2461

Traditional Rental Income: $1982

Airbnb ROI: 2.72%

Traditional ROI: 3.16%

35 Maple Ave

Chester, NY

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

$489,900

Airbnb cash on cash: 1.17%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $2797

Traditional Rental Income: $3279

Airbnb ROI: 1.17%