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.	$800,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 2.26% Airbnb Rental Income: $4261 Traditional Rental Income: $3820 Airbnb ROI: 1.65% Traditional ROI: 2.26%
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: 1.25% Traditional cash on cash: 1.96% Airbnb Rental Income: $4261 Traditional Rental Income: $3925 Airbnb ROI: 1.25% Traditional ROI: 1.96%
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: 2.98% Traditional cash on cash: 3.56% Airbnb Rental Income: $3164 Traditional Rental Income: $2684 Airbnb ROI: 2.98% Traditional ROI: 3.56%
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: -0.87% Traditional cash on cash: -0.38% Airbnb Rental Income: $4261 Traditional Rental Income: $4896 Airbnb ROI: -0.87% 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.	$489,900	Airbnb cash on cash: 1.84% Traditional cash on cash: 3.66% Airbnb Rental Income: $3164 Traditional Rental Income: $3279 Airbnb ROI: 1.84% 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.	$390,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 3.31% Airbnb Rental Income: $3164 Traditional Rental Income: $2578 Airbnb ROI: 2.96% Traditional ROI: 3.31%
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.	$649,999	Airbnb cash on cash: 2.45% Traditional cash on cash: 2.77% Airbnb Rental Income: $4261 Traditional Rental Income: $3559 Airbnb ROI: 2.45% Traditional ROI: 2.77%
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: 0.04% Traditional cash on cash: 0.62% Airbnb Rental Income: $3806 Traditional Rental Income: $3603 Airbnb ROI: 0.04% 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: 1.72% Traditional cash on cash: 0.48% Airbnb Rental Income: $3806 Traditional Rental Income: $2174 Airbnb ROI: 1.72% Traditional ROI: 0.48%
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: 0.06% Traditional cash on cash: 1.41% Airbnb Rental Income: $3806 Traditional Rental Income: $4236 Airbnb ROI: 0.06% Traditional ROI: 1.41%
26 Bridle Ln Chester, NY Welcome Home!!! Turn key & ready to be loved. Current owners spared no expense when renova...	4 beds \| 2 baths \| 1,718 sq.ft.	$685,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 2.45% Airbnb Rental Income: $4261 Traditional Rental Income: $3421 Airbnb ROI: 2.36% Traditional ROI: 2.45%
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: -0.26% Traditional cash on cash: 2.13% Airbnb Rental Income: $4261 Traditional Rental Income: $5897 Airbnb ROI: -0.26% Traditional ROI: 2.13%
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: 1.22% Traditional cash on cash: 2.14% Airbnb Rental Income: $4261 Traditional Rental Income: $4114 Airbnb ROI: 1.22% 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: 0.3% Traditional cash on cash: 1.88% Airbnb Rental Income: $3164 Traditional Rental Income: $3733 Airbnb ROI: 0.3% 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: -0.3% Traditional cash on cash: 0.19% Airbnb Rental Income: $4261 Traditional Rental Income: $4136 Airbnb ROI: -0.3% Traditional ROI: 0.19%
4 Debbie Ct Chester, NY Welcome to this exceptional private retreat nestled on beautifully landscaped grounds in d...	5 beds \| 5 baths \| 5,403 sq.ft.	$785,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 6.1% Airbnb Rental Income: $3806 Traditional Rental Income: $7227 Airbnb ROI: 0.3% Traditional ROI: 6.1%
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: -0.17% Traditional cash on cash: 2.72% Airbnb Rental Income: $3164 Traditional Rental Income: $4853 Airbnb ROI: -0.17% Traditional ROI: 2.72%
Odyssey Dr Chester, NY Odyssey Dr, Chester, NY 10918 \| Other	N/A beds \| N/A baths \| N/A	$350,000	Airbnb cash on cash: -6.23% Traditional cash on cash: -4.21% Airbnb Rental Income: $813 Traditional Rental Income: $1152 Airbnb ROI: -6.23% 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.	$460,000	Airbnb cash on cash: 2.8% Traditional cash on cash: 3.87% Airbnb Rental Income: $3164 Traditional Rental Income: $2908 Airbnb ROI: 2.8% Traditional ROI: 3.87%
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: 0.25% Traditional cash on cash: 1.51% Airbnb Rental Income: $4261 Traditional Rental Income: $4877 Airbnb ROI: 0.25% 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: 0.56% Traditional cash on cash: 2.1% Airbnb Rental Income: $3806 Traditional Rental Income: $4341 Airbnb ROI: 0.56% Traditional ROI: 2.1%
7 Hambletonian Ave Chester, NY Great new price! Come take a look at this 2 bedroom charmer with additional room offers po...	2 beds \| 1 baths \| 1,026 sq.ft.	$379,900	Airbnb cash on cash: 1.67% Traditional cash on cash: 2.4% Airbnb Rental Income: $2367 Traditional Rental Income: $2043 Airbnb ROI: 1.67% Traditional ROI: 2.4%
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: 3.14% Traditional cash on cash: 3.63% Airbnb Rental Income: $4261 Traditional Rental Income: $3640 Airbnb ROI: 3.14% Traditional ROI: 3.63%
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: -1.3% Traditional cash on cash: 1.15% Airbnb Rental Income: $813 Traditional Rental Income: $1176 Airbnb ROI: -1.3% Traditional ROI: 1.15%
10 Wells Sweep Ln Chester, NY Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combin...	4 beds \| 2 baths \| 3,000 sq.ft.	$869,900	Airbnb cash on cash: 1.33% Traditional cash on cash: 2.14% Airbnb Rental Income: $4261 Traditional Rental Income: $4022 Airbnb ROI: 1.33% Traditional ROI: 2.14%
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: 1.28% Traditional cash on cash: 2.12% Airbnb Rental Income: $4261 Traditional Rental Income: $4051 Airbnb ROI: 1.28% 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: 1.41% Traditional cash on cash: 2.86% Airbnb Rental Income: $3164 Traditional Rental Income: $3127 Airbnb ROI: 1.41% 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: 2.53% Traditional cash on cash: 3.04% Airbnb Rental Income: $4261 Traditional Rental Income: $3727 Airbnb ROI: 2.53% Traditional ROI: 3.04%
53 Gibson Hill Road Chester, NY Tucked away on over 3 private acres, this recently renovated custom residence offers a rar...	5 beds \| 4 baths \| 5,312 sq.ft.	$1,100,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 2% Airbnb Rental Income: $3806 Traditional Rental Income: $5518 Airbnb ROI: -0.48% Traditional ROI: 2%
149 Creamery Pond Rd Chester, NY Welcome to the highly sought-after Creamery Estate, located in the award-winning Warwick s...	3 beds \| 3 baths \| 2,740 sq.ft.	$799,900	Airbnb cash on cash: -0.08% Traditional cash on cash: 1.83% Airbnb Rental Income: $3164 Traditional Rental Income: $3870 Airbnb ROI: -0.08% Traditional ROI: 1.83%
17 Woodridge Dr Chester, NY Beautiful Colonial set on just under an acre of meticulously landscaped property, offering...	4 beds \| 2 baths \| 2,524 sq.ft.	$623,900	Airbnb cash on cash: 1.87% Traditional cash on cash: 3.16% Airbnb Rental Income: $4261 Traditional Rental Income: $4110 Airbnb ROI: 1.87% Traditional ROI: 3.16%
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: 1.42% Traditional cash on cash: 1.98% Airbnb Rental Income: $4261 Traditional Rental Income: $3801 Airbnb ROI: 1.42% Traditional ROI: 1.98%
58 Nancy Ln Chester, NY 58 Nancy Ln, Chester, NY 10918 \| Single Family Residential	3 beds \| 2 baths \| 2,718 sq.ft.	$749,999	Airbnb cash on cash: 0.66% Traditional cash on cash: 1.35% Airbnb Rental Income: $3164 Traditional Rental Income: $2931 Airbnb ROI: 0.66% Traditional ROI: 1.35%
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: 0.88% Traditional cash on cash: 1.21% Airbnb Rental Income: $4261 Traditional Rental Income: $3637 Airbnb ROI: 0.88% 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.	$499,000	Airbnb cash on cash: 3.6% Traditional cash on cash: 4.26% Airbnb Rental Income: $4261 Traditional Rental Income: $3669 Airbnb ROI: 3.6% Traditional ROI: 4.26%
45 Whitetail Run Chester, NY Set on over 10 private acres in the rolling hills of Orange County, this exceptional custo...	4 beds \| 2 baths \| 2,732 sq.ft.	$825,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 1.8% Airbnb Rental Income: $4261 Traditional Rental Income: $4039 Airbnb ROI: 0.92% Traditional ROI: 1.8%
24 Walnut St Chester, NY Welcome to 24 Walnut Street, Flexibility, Space & Endless Possibility in the Heart of Ches...	4 beds \| 2 baths \| 2,698 sq.ft.	$559,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 4.14% Airbnb Rental Income: $4261 Traditional Rental Income: $4084 Airbnb ROI: 2.76% Traditional ROI: 4.14%
86 Long Vista Ln Chester, NY 86 Long Vista Ln, Chester, NY 10918 \| Single Family Residential	5 beds \| 3 baths \| 3,764 sq.ft.	$899,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 1.87% Airbnb Rental Income: $3806 Traditional Rental Income: $4059 Airbnb ROI: 0.59% Traditional ROI: 1.87%
102 Beverly Rd Chester, NY Located in the Warwick School district on a coveted street sits this larger than life home...	4 beds \| 3 baths \| 4,130 sq.ft.	$1,090,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 2.38% Airbnb Rental Income: $4261 Traditional Rental Income: $5240 Airbnb ROI: 0.53% Traditional ROI: 2.38%
94 Booth Rd Chester, NY 94 Booth Rd, Chester, NY 10918 \| Single Family Residential	3 beds \| 2 baths \| 2,083 sq.ft.	$550,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 2.8% Airbnb Rental Income: $3164 Traditional Rental Income: $2922 Airbnb ROI: 1.88% Traditional ROI: 2.8%

Real Estate investment in Chester, NY

There are 73 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 $177. In July 2026, the average monthly cash on cash return in Chester is 2.00%. The average monthly rental income in Chester is $3,558.

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

There are 73 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 $3,558.

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.

$800,000

Airbnb cash on cash: 1.65%

Traditional cash on cash: 2.26%

Airbnb Rental Income: $4261

Traditional Rental Income: $3820

Airbnb ROI: 1.65%

Traditional ROI: 2.26%

24 Boville Ct

Chester, NY

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

$849,999

Airbnb cash on cash: 1.25%

Traditional cash on cash: 1.96%

Airbnb Rental Income: $4261

Traditional Rental Income: $3925

Airbnb ROI: 1.25%

Traditional ROI: 1.96%

151 Laroe Road

Chester, NY

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

$430,000

Airbnb cash on cash: 2.98%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $3164

Traditional Rental Income: $2684

Airbnb ROI: 2.98%

Traditional ROI: 3.56%

19 Greentree Ln

Chester, NY

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

$3,400,000

Airbnb cash on cash: -0.87%

Traditional cash on cash: -0.38%

Airbnb Rental Income: $4261

Traditional Rental Income: $4896

Airbnb ROI: -0.87%

Traditional ROI: -0.38%

35 Maple Ave

Chester, NY

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

$489,900

Airbnb cash on cash: 1.84%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $3164

Traditional Rental Income: $3279

Airbnb ROI: 1.84%

Traditional ROI: 3.66%

33 Meadow Ave

Chester, NY

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

$390,000

Airbnb cash on cash: 2.96%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $3164

Traditional Rental Income: $2578

Airbnb ROI: 2.96%

Traditional ROI: 3.31%

424 Laroe Rd

Chester, NY

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

$649,999

Airbnb cash on cash: 2.45%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $4261

Traditional Rental Income: $3559

Airbnb ROI: 2.45%

Traditional ROI: 2.77%

19 High St

Chester, NY

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

$1,145,000

Airbnb cash on cash: 0.04%

Traditional cash on cash: 0.62%

Airbnb Rental Income: $3806

Traditional Rental Income: $3603

Airbnb ROI: 0.04%