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
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: 1.11% Traditional cash on cash: 2.23% Airbnb Rental Income: $4097 Traditional Rental Income: $4114 Airbnb ROI: 1.11% Traditional ROI: 2.23%
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.	$1,199,900	Airbnb cash on cash: -0.42% Traditional cash on cash: 1.98% Airbnb Rental Income: $4097 Traditional Rental Income: $5897 Airbnb ROI: -0.42% Traditional ROI: 1.98%
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: 0.43% Traditional cash on cash: 1.17% Airbnb Rental Income: $4097 Traditional Rental Income: $3988 Airbnb ROI: 0.43% Traditional ROI: 1.17%
90 Main Street Chester, NY "The House on the Hill" Proudly offered for the first time in over 70 years. This expansiv...	4 beds \| 3 baths \| 3,955 sq.ft.	$1,300,000	Airbnb cash on cash: -1.17% Traditional cash on cash: -0.78% Airbnb Rental Income: $4097 Traditional Rental Income: $3693 Airbnb ROI: -1.17% Traditional ROI: -0.78%
65 Oxford Springs Road Chester, NY Welcome to 65 Oxford Springs Road, Chester, NY â a custom-built Country Contemporary set...	5 beds \| 4 baths \| 3,617 sq.ft.	$650,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 3.29% Airbnb Rental Income: $2914 Traditional Rental Income: $4293 Airbnb ROI: -0.09% Traditional ROI: 3.29%
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.	$724,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 2.39% Airbnb Rental Income: $4097 Traditional Rental Income: $3683 Airbnb ROI: 1.71% Traditional ROI: 2.39%
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: -0.4% Traditional cash on cash: 0.15% Airbnb Rental Income: $4097 Traditional Rental Income: $4136 Airbnb ROI: -0.4% 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.	$700,000	Airbnb cash on cash: -0.44% Traditional cash on cash: N/A Airbnb Rental Income: $2914 Traditional Rental Income: $0 Airbnb ROI: -0.44% Traditional ROI: N/A
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.	$799,999	Airbnb cash on cash: 1.59% Traditional cash on cash: 2.39% Airbnb Rental Income: $4097 Traditional Rental Income: $3820 Airbnb ROI: 1.59% Traditional ROI: 2.39%
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.	$899,900	Airbnb cash on cash: 0.97% Traditional cash on cash: 2.49% Airbnb Rental Income: $4097 Traditional Rental Income: $4501 Airbnb ROI: 0.97% Traditional ROI: 2.49%
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.	$879,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 1.56% Airbnb Rental Income: $4097 Traditional Rental Income: $4011 Airbnb ROI: 0.6% Traditional ROI: 1.56%
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: -0.23% Traditional cash on cash: 1.75% Airbnb Rental Income: $2676 Traditional Rental Income: $3733 Airbnb ROI: -0.23% Traditional ROI: 1.75%
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.	$449,000	Airbnb cash on cash: 4.33% Traditional cash on cash: 4.85% Airbnb Rental Income: $4097 Traditional Rental Income: $3444 Airbnb ROI: 4.33% Traditional ROI: 4.85%
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: 3.14% Traditional cash on cash: 3.57% Airbnb Rental Income: $4097 Traditional Rental Income: $3444 Airbnb ROI: 3.14% Traditional ROI: 3.57%
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: 3.69% Traditional cash on cash: 2.54% Airbnb Rental Income: $4097 Traditional Rental Income: $2689 Airbnb ROI: 3.69% Traditional ROI: 2.54%
1711 Kings Highway Chester, NY Nestled amidst the tranquil woods of Chester, NY, this stunning contemporary home offers a...	3 beds \| 2 baths \| 2,020 sq.ft.	$750,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 1.9% Airbnb Rental Income: $2676 Traditional Rental Income: $3343 Airbnb ROI: 0.04% Traditional ROI: 1.9%
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: 1.7% Traditional cash on cash: 2.72% Airbnb Rental Income: $4097 Traditional Rental Income: $3840 Airbnb ROI: 1.7% Traditional ROI: 2.72%
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: -0.39% Traditional cash on cash: 2.27% Airbnb Rental Income: $2914 Traditional Rental Income: $4345 Airbnb ROI: -0.39% Traditional ROI: 2.27%
81 Hambletonian Road Chester, NY OWN A PIECE OF HISTORY! AND SO MUCH MORE! This 3 bedroom, 2 full bathroom ranch built in 2...	3 beds \| 2 baths \| 1,938 sq.ft.	$624,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 2.35% Airbnb Rental Income: $2676 Traditional Rental Income: $3358 Airbnb ROI: 0.09% Traditional ROI: 2.35%
40 Mountainside Drive Chester, NY FANTASTIC NEW CONSTRUCTION to be built!! FULLY CUSTOM BUILD opportunity for your DREAM HO...	4 beds \| 3 baths \| 2,500 sq.ft.	$799,900	Airbnb cash on cash: 1.22% Traditional cash on cash: 2.92% Airbnb Rental Income: $4097 Traditional Rental Income: $4495 Airbnb ROI: 1.22% Traditional ROI: 2.92%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chester, NY

49 Stone Mountain Trail

Chester, NY

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

$850,000

Airbnb cash on cash: 1.11%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $4097

Traditional Rental Income: $4114

Airbnb ROI: 1.11%

Traditional ROI: 2.23%

16 Lori Lane

Chester, NY

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

$1,199,900

Airbnb cash on cash: -0.42%

Traditional cash on cash: 1.98%

Airbnb Rental Income: $4097

Traditional Rental Income: $5897

Airbnb ROI: -0.42%

Traditional ROI: 1.98%

5 Gabriels Drive

Chester, NY

4 beds | 3 baths | 2,722 sq.ft.

$1,099,000

Airbnb cash on cash: 0.43%

Traditional cash on cash: 1.17%

Airbnb Rental Income: $4097

Traditional Rental Income: $3988

Airbnb ROI: 0.43%

Traditional ROI: 1.17%

90 Main Street

Chester, NY

4 beds | 3 baths | 3,955 sq.ft.

$1,300,000

Airbnb cash on cash: -1.17%

Traditional cash on cash: -0.78%

Airbnb Rental Income: $4097

Traditional Rental Income: $3693

Airbnb ROI: -1.17%

Traditional ROI: -0.78%

65 Oxford Springs Road

Chester, NY

5 beds | 4 baths | 3,617 sq.ft.

$650,000

Airbnb cash on cash: -0.09%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $2914

Traditional Rental Income: $4293

Airbnb ROI: -0.09%

Traditional ROI: 3.29%

278 Gibson Hill Road

Chester, NY

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

$724,000

Airbnb cash on cash: 1.71%

Traditional cash on cash: 2.39%

Airbnb Rental Income: $4097

Traditional Rental Income: $3683

Airbnb ROI: 1.71%

Traditional ROI: 2.39%

20 Goshen Road

Chester, NY

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

$1,775,000

Airbnb cash on cash: -0.4%

Traditional cash on cash: 0.15%

Airbnb Rental Income: $4097

Traditional Rental Income: $4136

Airbnb ROI: -0.4%

Traditional ROI: 0.15%

507 Bull Mill Road

Chester, NY

5 beds | 3 baths | 3,115 sq.ft.

$700,000

Airbnb cash on cash: -0.44%

Traditional cash on cash: N/A

Airbnb Rental Income: $2914

Traditional Rental Income: $0

Airbnb ROI: -0.44%