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
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.	$740,000	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 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: -0.25% Traditional cash on cash: 2.7% Airbnb Rental Income: $2830 Traditional Rental Income: $4501 Airbnb ROI: -0.25% Traditional ROI: 2.7%
33 Meadow 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.	$430,000	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 Road Chester, NY Welcome to 65 Oxford Springs Road, Chester, NY a custom-built Country Contemporary set on ...	5 beds \| 4 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%
18 Oakland Avenue Chester, NY This is a "Neat as a pin" ranch in the Village of Chester. The kitchen has many updated ap...	2 beds \| 1 baths \| 1,084 sq.ft.	$369,900	Airbnb cash on cash: -1.4% Traditional cash on cash: 3.04% Airbnb Rental Income: $1165 Traditional Rental Income: $2324 Airbnb ROI: -1.4% Traditional ROI: 3.04%
278 Gibson Hill Road Chester, NY FULLY AVAILABLE. Amazing property, offers something for everyone! Gorgeously restored 3,97...	4 beds \| 3 baths \| 3,977 sq.ft.	$722,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 2.4% Airbnb Rental Income: $2830 Traditional Rental Income: $3683 Airbnb ROI: 0.15% Traditional ROI: 2.4%
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 Street Chester, NY Discover the perfect blend of versatility and charm with this exceptional property. The ma...	4 beds \| 3 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%
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%
2 Pine Hill Road Chester, NY Listed on the National Register of Historic Places in the Sugar Loaf Historic District, th...	3 beds \| 3 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 Drive Chester, NY Exquisite Colonial Estate: Timeless Grandeur Meets Modern Luxury Nestled gracefully on a ...	4 beds \| 3 baths \| 2,722 sq.ft.	$1,099,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 1.17% Airbnb Rental Income: $2830 Traditional Rental Income: $3988 Airbnb ROI: -0.61% Traditional ROI: 1.17%
37-39 Main Street 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%
20 Goshen Road Chester, NY Discover a rare opportunity to own a one-of-a-kind estate set on 53 sprawling acres in the...	4 beds \| 3 baths \| 3,348 sq.ft.	$1,775,000	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%
507 Bull Mill Road Chester, NY Welcome to this beautifully maintained colonial with a charming wrap-around front porch, s...	5 beds \| 3 baths \| 3,115 sq.ft.	$674,999	Airbnb cash on cash: -0.3% Traditional cash on cash: 2.44% Airbnb Rental Income: $3006 Traditional Rental Income: $4038 Airbnb ROI: -0.3% Traditional ROI: 2.44%
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: 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%
16 Mari Road Chester, NY Set back on a quiet street, just steps from downtown Sugar Loaf is this large home on almo...	4 beds \| 3 baths \| 2,098 sq.ft.	$500,000	Airbnb cash on cash: 1.31% Traditional cash on cash: 4.68% Airbnb Rental Income: $2830 Traditional Rental Income: $3743 Airbnb ROI: 1.31% Traditional ROI: 4.68%
220 Oxford Road Chester, NY Step into this newly renovated contemporary ranch, where comfort meets value on 6.3 acres ...	4 beds \| 4 baths \| 3,472 sq.ft.	$699,000	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%
2915 Whispering Hills Chester, NY Welcome to your next home in the highly desirable Whispering Hills community! Completely r...	3 beds \| 3 baths \| 1,331 sq.ft.	$369,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 3.69% Airbnb Rental Income: $2220 Traditional Rental Income: $2795 Airbnb ROI: 0.42% Traditional ROI: 3.69%
65 Hudson Street Chester, NY A truly rare opportunity to secure over two acres of prime land in the highly desirable an...	3 beds \| 1 baths \| 1,120 sq.ft.	$345,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 3.15% Airbnb Rental Income: $2220 Traditional Rental Income: $2297 Airbnb ROI: 1.19% Traditional ROI: 3.15%
2912 Whispering Hills Chester, NY Welcome home to this beautifully renovated 2 bedroom, 1 bathroom condo located in the desi...	2 beds \| 1 baths \| 1,084 sq.ft.	$304,900	Airbnb cash on cash: 0.03% Traditional cash on cash: 4.82% Airbnb Rental Income: $1165 Traditional Rental Income: $2155 Airbnb ROI: 0.03% Traditional ROI: 4.82%
80 Pewter Circle Chester, NY Welcome to the Villas at Sugar Loaf - an unbeatable location that rarely sees homes come o...	3 beds \| 3 baths \| 1,946 sq.ft.	$534,900	Airbnb cash on cash: -0.02% Traditional cash on cash: 3.22% Airbnb Rental Income: $2220 Traditional Rental Income: $3279 Airbnb ROI: -0.02% Traditional ROI: 3.22%
2104 Whispering Hills Chester, NY WHISPERING HILLS!! SOLD AS IS!!! Largest Model! Two Level Living! 3 Bedrooms! 2 1/2 Bathro...	3 beds \| 3 baths \| 1,331 sq.ft.	$299,900	Airbnb cash on cash: 2.77% Traditional cash on cash: 6.92% Airbnb Rental Income: $2220 Traditional Rental Income: $2834 Airbnb ROI: 2.77% Traditional ROI: 6.92%
6 Moffatt Lane Chester, NY Discover an exceptional income-generating two-family home nestled in the Village of Cheste...	5 beds \| 3 baths \| N/A	$499,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 4.69% Airbnb Rental Income: $3006 Traditional Rental Income: $3649 Airbnb ROI: 1.84% Traditional ROI: 4.69%
11 Saddle Hill Road Chester, NY Welcome to 11 Saddle Hill Road - A Perfect Blend of Luxury, Space & Location This stun...	4 beds \| 4 baths \| 3,489 sq.ft.	$845,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 1.67% Airbnb Rental Income: $2830 Traditional Rental Income: $4011 Airbnb ROI: -0.67% Traditional ROI: 1.67%
2317 Whispering Hills Chester, NY Welcome to your new home at 2317 Whispering Hills, Chester, NY 10918, where resort-style l...	2 beds \| 2 baths \| 1,072 sq.ft.	$299,999	Airbnb cash on cash: -1.55% Traditional cash on cash: 4.32% Airbnb Rental Income: $1165 Traditional Rental Income: $2440 Airbnb ROI: -1.55% Traditional ROI: 4.32%
47 Greycourt Avenue Chester, NY Classic farmhouse feel with contemporary updates on a generous 1.3-acre lot, with this hom...	4 beds \| 2 baths \| 1,386 sq.ft.	$425,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 4.25% Airbnb Rental Income: $2830 Traditional Rental Income: $3073 Airbnb ROI: 1.98% Traditional ROI: 4.25%
22 Bridle Lane Chester, NY This well-maintained 4-bedroom raised ranch located in Surrey Meadows, is just a short wal...	4 beds \| 2 baths \| 1,570 sq.ft.	$489,900	Airbnb cash on cash: 1.52% Traditional cash on cash: 3.73% Airbnb Rental Income: $2830 Traditional Rental Income: $3181 Airbnb ROI: 1.52% Traditional ROI: 3.73%
48 Brennan Court Chester, NY Welcome to this stunning home nestled on 5 acres near the heart of Chester, NY. Tucked awa...	4 beds \| 3 baths \| 3,063 sq.ft.	$769,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 2.36% Airbnb Rental Income: $2830 Traditional Rental Income: $4089 Airbnb ROI: -0.31% Traditional ROI: 2.36%
2 Dawn Court Chester, NY Spectacular 4 bedrooms, 2.5 bathrooms colonial in the very desirable Sugarloaf Heights. Th...	4 beds \| 3 baths \| 3,092 sq.ft.	$689,900	Airbnb cash on cash: 0.39% Traditional cash on cash: 3.44% Airbnb Rental Income: $2830 Traditional Rental Income: $4126 Airbnb ROI: 0.39% Traditional ROI: 3.44%
16 Oakland Avenue Chester, NY Charming 4-Bedroom Colonial in the Heart of Hudson Valley. Priced to Sell, tons of potenti...	4 beds \| 3 baths \| 2,090 sq.ft.	$400,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 6% Airbnb Rental Income: $2830 Traditional Rental Income: $3743 Airbnb ROI: 1.8% Traditional ROI: 6%
219 Bull Mill Road Chester, NY Welcome to your private oasis in Chester, NY! Immaculately maintained and move-in ready, t...	4 beds \| 2 baths \| 1,928 sq.ft.	$525,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 4.2% Airbnb Rental Income: $2830 Traditional Rental Income: $3647 Airbnb ROI: 1.19% Traditional ROI: 4.2%

Real Estate investment in Chester, NY

There are 32 properties for sale in the city of Chester . The median list price in Chester is $594,500 and the average price per square foot is $240. In December 2025, the average monthly cash on cash return in Chester is 3.00%. The average monthly rental income in Chester is $3,743.

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

There are 32 investment properties available for sale in Chester.

In 2025, the best neighborhood to buy investment property is Chester.

The ROI for Short-Term is higher than the Long-Term in Chester with average rental income of $2,830.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, NY

7 Park Place

Chester, NY

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

$740,000

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 Drive

Chester, NY

4 beds | 3 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 Avenue

Chester, NY

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

$430,000

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 Road

Chester, NY

5 beds | 4 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%

18 Oakland Avenue

Chester, NY

2 beds | 1 baths | 1,084 sq.ft.

$369,900

Airbnb cash on cash: -1.4%

Traditional cash on cash: 3.04%

Airbnb Rental Income: $1165

Traditional Rental Income: $2324

Airbnb ROI: -1.4%

Traditional ROI: 3.04%

278 Gibson Hill Road

Chester, NY

4 beds | 3 baths | 3,977 sq.ft.

$722,000

Airbnb cash on cash: 0.15%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $2830

Traditional Rental Income: $3683

Airbnb ROI: 0.15%

Traditional ROI: 2.4%

16 Lori Lane

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%

70 Main Street

Chester, NY

4 beds | 3 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%