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.

Condos for Sale in Chester, NY

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

Showing 4 Condo 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
2503 Whispering Hills Chester, NY PRICE REDUCED NEED TO SELL!!! Motivated Seller -- Discover this beautiful 3-bedroom, 2.5-b...	3 beds \| 3 baths \| 1,316 sq.ft.	$357,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 4.08% Airbnb Rental Income: $2676 Traditional Rental Income: $2754 Airbnb ROI: 1.96% Traditional ROI: 4.08%
3708 Whispering Hills Chester, NY Welcome to this fantastic 2-bedroom, 1.5-bathroom condo, perfectly situated in the desirab...	2 beds \| 2 baths \| 1,072 sq.ft.	$295,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 4.57% Airbnb Rental Income: $2848 Traditional Rental Income: $2453 Airbnb ROI: 3.61% Traditional ROI: 4.57%
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: 3.41% Traditional cash on cash: 4.32% Airbnb Rental Income: $2848 Traditional Rental Income: $2440 Airbnb ROI: 3.41% Traditional ROI: 4.32%
3915 Whispering Hills Chester, NY Highly desirable 3 BR, 2.5 Bath w/2 car garage condo in Whispering Hills! Pristine Conditi...	3 beds \| 3 baths \| 1,331 sq.ft.	$369,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 4.04% Airbnb Rental Income: $2676 Traditional Rental Income: $2845 Airbnb ROI: 1.72% Traditional ROI: 4.04%
Other Investment Properties for Sale in Chester
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%
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: 0.35% Traditional cash on cash: -0.74% Airbnb Rental Income: $4097 Traditional Rental Income: $1715 Airbnb ROI: 0.35% Traditional ROI: -0.74%
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%

Your search for investment property begins and ends here

Condos for Sale in Chester, NY

2503 Whispering Hills

Chester, NY

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

$357,000

Airbnb cash on cash: 1.96%

Traditional cash on cash: 4.08%

Airbnb Rental Income: $2676

Traditional Rental Income: $2754

Airbnb ROI: 1.96%

Traditional ROI: 4.08%

3708 Whispering Hills

Chester, NY

2 beds | 2 baths | 1,072 sq.ft.

$295,000

Airbnb cash on cash: 3.61%

Traditional cash on cash: 4.57%

Airbnb Rental Income: $2848

Traditional Rental Income: $2453

Airbnb ROI: 3.61%

Traditional ROI: 4.57%

2317 Whispering Hills

Chester, NY

2 beds | 2 baths | 1,072 sq.ft.

$299,999

Airbnb cash on cash: 3.41%

Traditional cash on cash: 4.32%

Airbnb Rental Income: $2848

Traditional Rental Income: $2440

Airbnb ROI: 3.41%

Traditional ROI: 4.32%

3915 Whispering Hills

Chester, NY

3 beds | 3 baths | 1,331 sq.ft.

$369,000

Airbnb cash on cash: 1.72%

Traditional cash on cash: 4.04%

Airbnb Rental Income: $2676

Traditional Rental Income: $2845

Airbnb ROI: 1.72%

Traditional ROI: 4.04%

Other Investment Properties for Sale in Chester

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%

Chester , NY

N/A beds | N/A baths | N/A

$1,500,000

Airbnb cash on cash: 0.35%

Traditional cash on cash: -0.74%

Airbnb Rental Income: $4097

Traditional Rental Income: $1715

Airbnb ROI: 0.35%

Traditional ROI: -0.74%

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%

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%

Chester , NY

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