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
1005 Whispering Hills Chester, NY ONLY CASH OFFERS!! LOW TAXES! Two Level Living! 2 Bedrooms! 1 1/2 Bathrooms! 1 Car Garage!...	2 beds \| 2 baths \| 1,053 sq.ft.	$249,900	Airbnb cash on cash: 3.83% Traditional cash on cash: 7.43% Airbnb Rental Income: $2117 Traditional Rental Income: $2426 Airbnb ROI: 3.83% Traditional ROI: 7.43%
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.	$730,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 3% Airbnb Rental Income: $3935 Traditional Rental Income: $4642 Airbnb ROI: 0.72% Traditional ROI: 3%
1311 Whispering Hills Chester, NY Rare Opportunity! Welcome to this stunning 3-bedroom, 2-bathroom end-unit in the highly so...	3 beds \| 2 baths \| 1,316 sq.ft.	$349,900	Airbnb cash on cash: -0.57% Traditional cash on cash: 4.2% Airbnb Rental Income: $1553 Traditional Rental Income: $2673 Airbnb ROI: -0.57% Traditional ROI: 4.2%
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: 0.92% Traditional cash on cash: 2.7% Airbnb Rental Income: $3935 Traditional Rental Income: $4501 Airbnb ROI: 0.92% 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: -0.66% Traditional cash on cash: 3.27% Airbnb Rental Income: $1553 Traditional Rental Income: $2578 Airbnb ROI: -0.66% Traditional ROI: 3.27%
58 Oxford Springs Road Chester, NY Tucked away in a serene, wooded setting, this extraordinary private retreat offers a rare ...	1 beds \| 1 baths \| 783 sq.ft.	$349,900	Airbnb cash on cash: -1.22% Traditional cash on cash: 2.63% Airbnb Rental Income: $1051 Traditional Rental Income: $1953 Airbnb ROI: -1.22% Traditional ROI: 2.63%
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: -0.47% Traditional cash on cash: 0.19% Airbnb Rental Income: $3935 Traditional Rental Income: $4136 Airbnb ROI: -0.47% Traditional ROI: 0.19%
4 Debbie Court Chester, NY DISCOVER THE EPITOME OF LUXURY LIVING! With 5400 sq ft of breathtaking property, where eve...	5 beds \| 6 baths \| 5,403 sq.ft.	$840,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 5.64% Airbnb Rental Income: $2745 Traditional Rental Income: $7227 Airbnb ROI: -0.92% Traditional ROI: 5.64%
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: 1.75% Traditional cash on cash: 2.87% Airbnb Rental Income: $3935 Traditional Rental Income: $3820 Airbnb ROI: 1.75% Traditional ROI: 2.87%
2948 State Route 94 Chester, NY Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, th...	4 beds \| 3 baths \| 3,866 sq.ft.	$1,300,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 0.02% Airbnb Rental Income: $3935 Traditional Rental Income: $4211 Airbnb ROI: -0.91% Traditional ROI: 0.02%
3917 Whispering Hills Chester, NY Welcome to Whispering Hills! This beautifully maintained home features a galley kitchen wi...	2 beds \| 2 baths \| 1,072 sq.ft.	$305,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 3.86% Airbnb Rental Income: $2117 Traditional Rental Income: $2391 Airbnb ROI: 1.02% Traditional ROI: 3.86%
2113 Whispering Hills 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: 0.51% Traditional cash on cash: 2.12% Airbnb Rental Income: $2117 Traditional Rental Income: $1992 Airbnb ROI: 0.51% Traditional ROI: 2.12%
1367 Kings Highway Chester, NY Historic Colonial Era Home in the Heart of Sugar Loaf, NY Located just 60 minutes from NYC...	3 beds \| 2 baths \| 1,728 sq.ft.	$460,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 3.87% Airbnb Rental Income: $1553 Traditional Rental Income: $2908 Airbnb ROI: -0.32% Traditional ROI: 3.87%
5 Bens Way Chester, NY Welcome to 5 Bens Way, a beautifully positioned residence tucked away on a quiet cul-de-sa...	4 beds \| 3 baths \| 2,544 sq.ft.	$699,999	Airbnb cash on cash: 0.9% Traditional cash on cash: 2.09% Airbnb Rental Income: $3935 Traditional Rental Income: $3869 Airbnb ROI: 0.9% Traditional ROI: 2.09%
7 Hambletonian Avenue Chester, NY This 2 bedroom charmer with additional room offers potential 3 bedrooms. Larger than it lo...	2 beds \| 1 baths \| 1,026 sq.ft.	$410,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 2.15% Airbnb Rental Income: $2117 Traditional Rental Income: $2043 Airbnb ROI: 0.93% Traditional ROI: 2.15%
10 Wells Sweep Lane Chester, NY Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combin...	4 beds \| 3 baths \| 3,000 sq.ft.	$869,900	Airbnb cash on cash: 0.99% Traditional cash on cash: 2.14% Airbnb Rental Income: $3935 Traditional Rental Income: $4022 Airbnb ROI: 0.99% Traditional ROI: 2.14%
1414 Kings Highway Chester, NY Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combin...	4 beds \| 3 baths \| 3,200 sq.ft.	$879,900	Airbnb cash on cash: 0.95% Traditional cash on cash: 2.12% Airbnb Rental Income: $3935 Traditional Rental Income: $4051 Airbnb ROI: 0.95% Traditional ROI: 2.12%
5 N Hudson Street 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: -1.46% Traditional cash on cash: 2.86% Airbnb Rental Income: $1553 Traditional Rental Income: $3127 Airbnb ROI: -1.46% Traditional ROI: 2.86%
90 Pewter Circle Chester, NY This beautiful custom home is planned to be built in the highly sought-after Sugar Loaf ar...	4 beds \| 3 baths \| 2,250 sq.ft.	$759,900	Airbnb cash on cash: 2.14% Traditional cash on cash: 3.04% Airbnb Rental Income: $3935 Traditional Rental Income: $3727 Airbnb ROI: 2.14% Traditional ROI: 3.04%
16 Oakland Avenue Chester, NY .	4 beds \| 3 baths \| 2,090 sq.ft.	$425,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 5.59% Airbnb Rental Income: $3935 Traditional Rental Income: $3743 Airbnb ROI: 3.95% Traditional ROI: 5.59%
3910 Whispering Hills Chester, NY Welcome to 3910 Whispering Hills - a refined, turnkey townhome in one of Chester's most de...	3 beds \| 3 baths \| 1,331 sq.ft.	$369,900	Airbnb cash on cash: -0.99% Traditional cash on cash: 3.71% Airbnb Rental Income: $1553 Traditional Rental Income: $2737 Airbnb ROI: -0.99% Traditional ROI: 3.71%
4508 Whispering Hills Chester, NY Welcome to 4508 Whispering Hills, a well-maintained and thoughtfully updated 2-bedroom, 1....	2 beds \| 2 baths \| 1,072 sq.ft.	$299,999	Airbnb cash on cash: 1.31% Traditional cash on cash: 3.86% Airbnb Rental Income: $2117 Traditional Rental Income: $2294 Airbnb ROI: 1.31% Traditional ROI: 3.86%
2913 Whispering Hills Chester, NY Welcome to 2913 Whispering Hills Drive - A Move-In Ready End Unit in the Heart of Chester!...	2 beds \| 1 baths \| 1,084 sq.ft.	$279,900	Airbnb cash on cash: 1.16% Traditional cash on cash: 2.98% Airbnb Rental Income: $2117 Traditional Rental Income: $2056 Airbnb ROI: 1.16% Traditional ROI: 2.98%
34 Booth Road Chester, NY Updated 4BR Colonial in Chester - Monroe-Woodbury Schools! Welcome home to this beautifull...	4 beds \| 3 baths \| 2,506 sq.ft.	$699,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 2.24% Airbnb Rental Income: $3935 Traditional Rental Income: $3763 Airbnb ROI: 1.21% Traditional ROI: 2.24%
31 Hudson Street Chester, NY Set on nearly half an acre in the Village of Chester, this charming brick Cape Cod offers ...	2 beds \| 2 baths \| 1,998 sq.ft.	$449,900	Airbnb cash on cash: 0.12% Traditional cash on cash: 3.19% Airbnb Rental Income: $2117 Traditional Rental Income: $2872 Airbnb ROI: 0.12% Traditional ROI: 3.19%

Real Estate investment in Chester, NY

There are 25 properties for sale in the city of Chester . The median list price in Chester is $274,900 and the average price per square foot is $164. In April 2026, the average monthly cash on cash return in Chester is 3.00%. The average monthly rental income in Chester is $3,127.

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

There are 25 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 $3,127.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, NY

1005 Whispering Hills

Chester, NY

2 beds | 2 baths | 1,053 sq.ft.

$249,900

Airbnb cash on cash: 3.83%

Traditional cash on cash: 7.43%

Airbnb Rental Income: $2117

Traditional Rental Income: $2426

Airbnb ROI: 3.83%

Traditional ROI: 7.43%

7 Park Place

Chester, NY

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

$730,000

Airbnb cash on cash: 0.72%

Traditional cash on cash: 3%

Airbnb Rental Income: $3935

Traditional Rental Income: $4642

Airbnb ROI: 0.72%

Traditional ROI: 3%

1311 Whispering Hills

Chester, NY

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

$349,900

Airbnb cash on cash: -0.57%

Traditional cash on cash: 4.2%

Airbnb Rental Income: $1553

Traditional Rental Income: $2673

Airbnb ROI: -0.57%

Traditional ROI: 4.2%

32 Mountainside Drive

Chester, NY

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

$849,900

Airbnb cash on cash: 0.92%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $3935

Traditional Rental Income: $4501

Airbnb ROI: 0.92%

Traditional ROI: 2.7%

33 Meadow Avenue

Chester, NY

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

$400,000

Airbnb cash on cash: -0.66%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $1553

Traditional Rental Income: $2578

Airbnb ROI: -0.66%

Traditional ROI: 3.27%

58 Oxford Springs Road

Chester, NY

1 beds | 1 baths | 783 sq.ft.

$349,900

Airbnb cash on cash: -1.22%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $1051

Traditional Rental Income: $1953

Airbnb ROI: -1.22%

Traditional ROI: 2.63%

20 Goshen Road

Chester, NY

4 beds | 3 baths | 3,348 sq.ft.

$1,725,000

Airbnb cash on cash: -0.47%

Traditional cash on cash: 0.19%

Airbnb Rental Income: $3935

Traditional Rental Income: $4136

Airbnb ROI: -0.47%

Traditional ROI: 0.19%

4 Debbie Court

Chester, NY

5 beds | 6 baths | 5,403 sq.ft.

$840,000

Airbnb cash on cash: -0.92%

Traditional cash on cash: 5.64%

Airbnb Rental Income: $2745

Traditional Rental Income: $7227

Airbnb ROI: -0.92%