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.

Single Family Homes for Sale in Chester, NY

Search for Single Family Residential for Sale in Chester, New York. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 20 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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: 0.72% Traditional cash on cash: 2.7% Airbnb Rental Income: $3747 Traditional Rental Income: $4501 Airbnb ROI: 0.72% 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.	$440,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 2.89% Airbnb Rental Income: $2448 Traditional Rental Income: $2578 Airbnb ROI: 1.12% Traditional ROI: 2.89%
278 Gibson Hill Road Chester, NY AMAZING PROPERTY -- offers something for everyone! Gorgeously restored 3,977 square foot c...	4 beds \| 3 baths \| 3,977 sq.ft.	$723,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 2.39% Airbnb Rental Income: $3747 Traditional Rental Income: $3683 Airbnb ROI: 1.28% Traditional ROI: 2.39%
11 Saddle Hill Road Chester, NY Welcome to 11 Saddle Hill Road â A Perfect Blend of Luxury, Space & Location This st...	4 beds \| 4 baths \| 4,489 sq.ft.	$845,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 1.67% Airbnb Rental Income: $3747 Traditional Rental Income: $4011 Airbnb ROI: 0.3% Traditional ROI: 1.67%
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: -0.67% Traditional cash on cash: 2.08% Airbnb Rental Income: $3747 Traditional Rental Income: $5897 Airbnb ROI: -0.67% 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: 3.13% Traditional cash on cash: 4.16% Airbnb Rental Income: $3747 Traditional Rental Income: $3391 Airbnb ROI: 3.13% Traditional ROI: 4.16%
49 Stone Mountain Trail Chester, NY Stunning curb appeal. Unrivaled privacy. This 3-story, 3,650+ sq. ft. contemporary colonia...	4 beds \| 3 baths \| 3,656 sq.ft.	$850,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 2.23% Airbnb Rental Income: $3747 Traditional Rental Income: $4114 Airbnb ROI: 0.74% Traditional ROI: 2.23%
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.	$915,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 1.75% Airbnb Rental Income: $2448 Traditional Rental Income: $3733 Airbnb ROI: -0.46% Traditional ROI: 1.75%
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: 0.14% Traditional cash on cash: 1.17% Airbnb Rental Income: $3747 Traditional Rental Income: $3988 Airbnb ROI: 0.14% Traditional ROI: 1.17%
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: -0.58% Traditional cash on cash: 0.15% Airbnb Rental Income: $3747 Traditional Rental Income: $4136 Airbnb ROI: -0.58% 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: 0.34% Traditional cash on cash: 2.44% Airbnb Rental Income: $3487 Traditional Rental Income: $4038 Airbnb ROI: 0.34% 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: 1.51% Traditional cash on cash: 2.87% Airbnb Rental Income: $3747 Traditional Rental Income: $3820 Airbnb ROI: 1.51% Traditional ROI: 2.87%
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: 3.9% Traditional cash on cash: 5.18% Airbnb Rental Income: $3747 Traditional Rental Income: $3444 Airbnb ROI: 3.9% Traditional ROI: 5.18%
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.	$549,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 4.22% Airbnb Rental Income: $3747 Traditional Rental Income: $3775 Airbnb ROI: 2.58% Traditional ROI: 4.22%
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.	$699,900	Airbnb cash on cash: 1.55% Traditional cash on cash: 3.37% Airbnb Rental Income: $3747 Traditional Rental Income: $4126 Airbnb ROI: 1.55% Traditional ROI: 3.37%
9 June Road Chester, NY Welcome to 9 June Road, a rare gem offering 3,122 square feet of well-designed living spac...	4 beds \| 3 baths \| 2,402 sq.ft.	$649,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 2.72% Airbnb Rental Income: $3747 Traditional Rental Income: $3840 Airbnb ROI: 1.22% Traditional ROI: 2.72%
15 Mari Road Chester, NY Move right into beautiful 15 Mari Road. Situated in a choice neighborhood and inclusive of...	4 beds \| 2 baths \| 1,888 sq.ft.	$499,000	Airbnb cash on cash: 3.06% Traditional cash on cash: 2.54% Airbnb Rental Income: $3747 Traditional Rental Income: $2689 Airbnb ROI: 3.06% Traditional ROI: 2.54%
284 Bull Mill Road Chester, NY Monroe's Stunning Mini Mansion Awaits Its New Owner! This exquisite home offers everything...	5 beds \| 3 baths \| 3,485 sq.ft.	$849,900	Airbnb cash on cash: 0.21% Traditional cash on cash: 2.27% Airbnb Rental Income: $3487 Traditional Rental Income: $4345 Airbnb ROI: 0.21% Traditional ROI: 2.27%
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: 3.19% Traditional cash on cash: 3.73% Airbnb Rental Income: $3747 Traditional Rental Income: $3181 Airbnb ROI: 3.19% 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: 0.75% Traditional cash on cash: 2.36% Airbnb Rental Income: $3747 Traditional Rental Income: $4089 Airbnb ROI: 0.75% Traditional ROI: 2.36%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chester, NY

32 Mountainside Drive

Chester, NY

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

$849,900

Airbnb cash on cash: 0.72%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $3747

Traditional Rental Income: $4501

Airbnb ROI: 0.72%

Traditional ROI: 2.7%

33 Meadow Avenue

Chester, NY

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

$440,000

Airbnb cash on cash: 1.12%

Traditional cash on cash: 2.89%

Airbnb Rental Income: $2448

Traditional Rental Income: $2578

Airbnb ROI: 1.12%

Traditional ROI: 2.89%

278 Gibson Hill Road

Chester, NY

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

$723,000

Airbnb cash on cash: 1.28%

Traditional cash on cash: 2.39%

Airbnb Rental Income: $3747

Traditional Rental Income: $3683

Airbnb ROI: 1.28%

Traditional ROI: 2.39%

11 Saddle Hill Road

Chester, NY

4 beds | 4 baths | 4,489 sq.ft.

$845,000

Airbnb cash on cash: 0.3%

Traditional cash on cash: 1.67%

Airbnb Rental Income: $3747

Traditional Rental Income: $4011

Airbnb ROI: 0.3%

Traditional ROI: 1.67%

16 Lori Lane

Chester, NY

4 beds | 5 baths | 4,624 sq.ft.

$1,160,000

Airbnb cash on cash: -0.67%

Traditional cash on cash: 2.08%

Airbnb Rental Income: $3747

Traditional Rental Income: $5897

Airbnb ROI: -0.67%

Traditional ROI: 2.08%

70 Main Street

Chester, NY

4 beds | 3 baths | 1,357 sq.ft.

$475,000

Airbnb cash on cash: 3.13%

Traditional cash on cash: 4.16%

Airbnb Rental Income: $3747

Traditional Rental Income: $3391

Airbnb ROI: 3.13%

Traditional ROI: 4.16%

49 Stone Mountain Trail

Chester, NY

4 beds | 3 baths | 3,656 sq.ft.

$850,000

Airbnb cash on cash: 0.74%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $3747

Traditional Rental Income: $4114

Airbnb ROI: 0.74%

Traditional ROI: 2.23%

2 Pine Hill Road

Chester, NY

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

$915,000

Airbnb cash on cash: -0.46%

Traditional cash on cash: 1.75%

Airbnb Rental Income: $2448

Traditional Rental Income: $3733

Airbnb ROI: -0.46%