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
128 Booth Road Chester, NY FULLY AVAILABLE 10/6 Welcome to your sanctuary in Chester, New York! This impeccable four...	4 beds \| 3 baths \| 2,102 sq.ft.	$549,920	Airbnb cash on cash: 8.62% Traditional cash on cash: 3.78% Airbnb Rental Income: $7580 Traditional Rental Income: $3644 Airbnb ROI: 8.62% Traditional ROI: 3.78%
152 Gibson Hill Road Chester, NY Set back from the road, nestled behind mature native and ornamental trees sits this statel...	4 beds \| 3 baths \| 3,176 sq.ft.	$799,000	Airbnb cash on cash: 4.96% Traditional cash on cash: 2.04% Airbnb Rental Income: $7580 Traditional Rental Income: $3955 Airbnb ROI: 4.96% Traditional ROI: 2.04%
1002 Whispering Hills Chester, NY This charming three-bedroom, two-bath townhouse is nestled in the Whispering Hills communi...	3 beds \| 2 baths \| 1,316 sq.ft.	$345,000	Airbnb cash on cash: 5.64% Traditional cash on cash: 3.59% Airbnb Rental Income: $4130 Traditional Rental Income: $2586 Airbnb ROI: 5.64% Traditional ROI: 3.59%
24 Woodridge Drive Chester, NY Discover your perfect home in Blooming Grove New York! This charming four bedroom and a tw...	4 beds \| 3 baths \| 2,680 sq.ft.	$579,000	Airbnb cash on cash: 7.2% Traditional cash on cash: 3.16% Airbnb Rental Income: $7580 Traditional Rental Income: $3944 Airbnb ROI: 7.2% Traditional ROI: 3.16%
1807 Whispering Hills Chester, NY Welcome to 1807 Whispering Hills, Chester Your Dream Home Awaits! This 2 bedroom 1.5 ba...	2 beds \| 2 baths \| 1,086 sq.ft.	$299,000	Airbnb cash on cash: 4.96% Traditional cash on cash: 3.85% Airbnb Rental Income: $3305 Traditional Rental Income: $2253 Airbnb ROI: 4.96% Traditional ROI: 3.85%
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.	$784,000	Airbnb cash on cash: 5.56% Traditional cash on cash: 2.42% Airbnb Rental Income: $7580 Traditional Rental Income: $3834 Airbnb ROI: 5.56% Traditional ROI: 2.42%
1301 Kings Highway Chester, NY Located just outside the quaint village of Sugar Loaf sits this 1835 farm house. Situated ...	4 beds \| 3 baths \| 2,676 sq.ft.	$685,000	Airbnb cash on cash: 6.77% Traditional cash on cash: 3.17% Airbnb Rental Income: $7580 Traditional Rental Income: $3824 Airbnb ROI: 6.77% Traditional ROI: 3.17%
412 Laroe Road Chester, NY This extraordinarily charming totally updated high ranch is sitting on 2.4 private landsc...	3 beds \| 2 baths \| 1,848 sq.ft.	$579,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 2.6% Airbnb Rental Income: $4130 Traditional Rental Income: $3062 Airbnb ROI: 2.96% Traditional ROI: 2.6%
60 Evan Road Chester, NY WARWICK SCHOOL DISTRICT & No Hoa Fees! Welcome to Kings Estate; centrally located to Ches...	3 beds \| 3 baths \| 1,452 sq.ft.	$395,000	Airbnb cash on cash: 5.9% Traditional cash on cash: 4.88% Airbnb Rental Income: $4130 Traditional Rental Income: $2875 Airbnb ROI: 5.9% Traditional ROI: 4.88%
65 Oxford Springs Road Chester, NY This stunning 5-bedroom, 4-bath colonial offers 3,400 square feet of living space that ble...	5 beds \| 4 baths \| 3,464 sq.ft.	$799,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 3.19% Airbnb Rental Income: $6686 Traditional Rental Income: $4747 Airbnb ROI: 4.04% Traditional ROI: 3.19%
2910 Whispering Hills Chester, NY Spacious End Unit Duplex Townhouse featuring 3 Bedrooms, 2.5 Bathrooms and oversized 2 car...	3 beds \| 3 baths \| 1,331 sq.ft.	$365,000	Airbnb cash on cash: 5.57% Traditional cash on cash: 4.12% Airbnb Rental Income: $4130 Traditional Rental Income: $2757 Airbnb ROI: 5.57% Traditional ROI: 4.12%
151 Kings Highway Chester, NY Nestled on a picturesque 14-acre lot overlooking Sugarloaf, the Adirondack timber frame ho...	4 beds \| 5 baths \| 5,638 sq.ft.	$1,588,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 0.61% Airbnb Rental Income: $7580 Traditional Rental Income: $5763 Airbnb ROI: 0.86% Traditional ROI: 0.61%
11 Saddle Hill Road Chester, NY Welcome to 11 Saddle River Rd, a beautifully updated home situated on a tranquil private r...	4 beds \| 4 baths \| 4,489 sq.ft.	$1,100,000	Airbnb cash on cash: 3.18% Traditional cash on cash: 1.77% Airbnb Rental Income: $7580 Traditional Rental Income: $4688 Airbnb ROI: 3.18% Traditional ROI: 1.77%
504 Bull Mill Road Chester, NY A NEW HOME IS A NEW BEGINNING!! Impressive home - redone to perfection is waiting for you!...	4 beds \| 3 baths \| 2,777 sq.ft.	$790,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 2.1% Airbnb Rental Income: $7580 Traditional Rental Income: $3905 Airbnb ROI: 5.12% Traditional ROI: 2.1%
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: 5.11% Traditional cash on cash: 2.92% Airbnb Rental Income: $7580 Traditional Rental Income: $4495 Airbnb ROI: 5.11% Traditional ROI: 2.92%
1911 Whispering Hills Chester, NY Welcome to your dream oasis nestled in the heart of Chester, NY This meticulously renovate...	3 beds \| 2 baths \| 1,316 sq.ft.	$364,999	Airbnb cash on cash: 5.75% Traditional cash on cash: 3.98% Airbnb Rental Income: $4130 Traditional Rental Income: $2646 Airbnb ROI: 5.75% Traditional ROI: 3.98%
1818 Whispering Hills Chester, NY There is nothing to do but move in, this unit has loads of upgrades. The kitchen and baths...	2 beds \| 2 baths \| 1,086 sq.ft.	$289,900	Airbnb cash on cash: 6.05% Traditional cash on cash: 5.41% Airbnb Rental Income: $3305 Traditional Rental Income: $2389 Airbnb ROI: 6.05% Traditional ROI: 5.41%
2 Park Place Chester, NY This custom-built colonial w/ 4 bedrooms & 4.5 baths on 7.5 acres is a must see. A grand f...	4 beds \| 5 baths \| 4,492 sq.ft.	$859,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 3.58% Airbnb Rental Income: $7580 Traditional Rental Income: $6042 Airbnb ROI: 3.69% Traditional ROI: 3.58%
4 Greycourt Road Chester, NY Magnificent sprawling ranch situated on a park like setting with 2.80 acres with mature la...	3 beds \| 2 baths \| N/A	$599,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 2.62% Airbnb Rental Income: $4130 Traditional Rental Income: $3141 Airbnb ROI: 2.82% Traditional ROI: 2.62%
40 Farmingdale Road Chester, NY Beautifully renovated 4-bedroom, 3-bathroom split-level home nestled on 4.3 acres of stunn...	4 beds \| 3 baths \| 2,269 sq.ft.	$499,000	Airbnb cash on cash: 9.79% Traditional cash on cash: 4.56% Airbnb Rental Income: $7580 Traditional Rental Income: $3688 Airbnb ROI: 9.79% Traditional ROI: 4.56%
5 Oxford Springs Road Chester, NY ONE OF A KIND GEM! Nestled in a private setting on 3.3 acres, this unique house welcomes ...	3 beds \| 2 baths \| 2,608 sq.ft.	$625,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 1.91% Airbnb Rental Income: $4130 Traditional Rental Income: $3022 Airbnb ROI: 2.31% Traditional ROI: 1.91%
3406 Whispering Hills Chester, NY Welcome to this beautifully maintained 2 bedroom, 1.5 bath condo nestled in the heart of C...	2 beds \| 2 baths \| 1,086 sq.ft.	$289,000	Airbnb cash on cash: 5.02% Traditional cash on cash: 4.05% Airbnb Rental Income: $3305 Traditional Rental Income: $2302 Airbnb ROI: 5.02% Traditional ROI: 4.05%
77 Surrey Road Chester, NY Pride of ownership at it's finest! What an honor to represent this original owner's home! ...	5 beds \| 3 baths \| 2,136 sq.ft.	$549,000	Airbnb cash on cash: 7.3% Traditional cash on cash: 4.06% Airbnb Rental Income: $6686 Traditional Rental Income: $3719 Airbnb ROI: 7.3% Traditional ROI: 4.06%
60 Rose Ann Lane Chester, NY Serenity awaits! Come home to your pristine 4 bdrm, 3 ba Colonial nestled on 1.3 acres in ...	4 beds \| 3 baths \| 2,326 sq.ft.	$569,999	Airbnb cash on cash: 7.93% Traditional cash on cash: 3.47% Airbnb Rental Income: $7580 Traditional Rental Income: $3750 Airbnb ROI: 7.93% Traditional ROI: 3.47%
12 Meadow Avenue Chester, NY New Village Colonial with all the options, walk out basement with 10 ft ceiling height, ro...	4 beds \| 3 baths \| 2,050 sq.ft.	$609,000	Airbnb cash on cash: 7.33% Traditional cash on cash: 3.18% Airbnb Rental Income: $7580 Traditional Rental Income: $3766 Airbnb ROI: 7.33% Traditional ROI: 3.18%
38 Rebecca Road Chester, NY Multiple offer situation submit highest/best offers by 10am Sept 9th --- WELCOME HOME!...	4 beds \| 3 baths \| 1,910 sq.ft.	$575,000	Airbnb cash on cash: 8.12% Traditional cash on cash: 3.14% Airbnb Rental Income: $7580 Traditional Rental Income: $3454 Airbnb ROI: 8.12% Traditional ROI: 3.14%
11 Townsend Place Chester, NY Welcome to your dream home! This beautifully maintained split-level house, in a cul-de-sac...	3 beds \| 2 baths \| 1,788 sq.ft.	$499,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 3.7% Airbnb Rental Income: $4130 Traditional Rental Income: $3187 Airbnb ROI: 3.84% Traditional ROI: 3.7%
79 Conklingtown Road Chester, NY Beautiful 4 bedrooms, 3 full baths with hardwood floors throughout!! Updated bathrooms, ce...	4 beds \| 3 baths \| 2,636 sq.ft.	$555,000	Airbnb cash on cash: 8.65% Traditional cash on cash: 4.24% Airbnb Rental Income: $7580 Traditional Rental Income: $3840 Airbnb ROI: 8.65% Traditional ROI: 4.24%
3606 Whispering Hills Chester, NY FANTASTIC 2 bedroom, 1 1/2 bath condo/townhouse (2 floors) with an attached 2 car garage -...	2 beds \| 2 baths \| 1,086 sq.ft.	$264,000	Airbnb cash on cash: 6.02% Traditional cash on cash: 5.37% Airbnb Rental Income: $3305 Traditional Rental Income: $2404 Airbnb ROI: 6.02% Traditional ROI: 5.37%

Real Estate investment in Chester, NY

There are 29 properties for sale in the city of Chester . The median list price in Chester is $572,500 and the average price per square foot is $240. In November 2024, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $3,666.

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

There are 29 investment properties available for sale in Chester.

In 2024, 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 $7,580.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, NY

128 Booth Road

Chester, NY

4 beds | 3 baths | 2,102 sq.ft.

$549,920

Airbnb cash on cash: 8.62%

Traditional cash on cash: 3.78%

Airbnb Rental Income: $7580

Traditional Rental Income: $3644

Airbnb ROI: 8.62%

Traditional ROI: 3.78%

152 Gibson Hill Road

Chester, NY

4 beds | 3 baths | 3,176 sq.ft.

$799,000

Airbnb cash on cash: 4.96%

Traditional cash on cash: 2.04%

Airbnb Rental Income: $7580

Traditional Rental Income: $3955

Airbnb ROI: 4.96%

Traditional ROI: 2.04%

1002 Whispering Hills

Chester, NY

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

$345,000

Airbnb cash on cash: 5.64%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $4130

Traditional Rental Income: $2586

Airbnb ROI: 5.64%

Traditional ROI: 3.59%

24 Woodridge Drive

Chester, NY

4 beds | 3 baths | 2,680 sq.ft.

$579,000

Airbnb cash on cash: 7.2%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $7580

Traditional Rental Income: $3944

Airbnb ROI: 7.2%

Traditional ROI: 3.16%

1807 Whispering Hills

Chester, NY

2 beds | 2 baths | 1,086 sq.ft.

$299,000

Airbnb cash on cash: 4.96%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $3305

Traditional Rental Income: $2253

Airbnb ROI: 4.96%

Traditional ROI: 3.85%

278 Gibson Hill Road

Chester, NY

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

$784,000

Airbnb cash on cash: 5.56%

Traditional cash on cash: 2.42%

Airbnb Rental Income: $7580

Traditional Rental Income: $3834

Airbnb ROI: 5.56%

Traditional ROI: 2.42%

1301 Kings Highway

Chester, NY

4 beds | 3 baths | 2,676 sq.ft.

$685,000

Airbnb cash on cash: 6.77%

Traditional cash on cash: 3.17%

Airbnb Rental Income: $7580

Traditional Rental Income: $3824

Airbnb ROI: 6.77%

Traditional ROI: 3.17%

412 Laroe Road

Chester, NY

3 beds | 2 baths | 1,848 sq.ft.

$579,000

Airbnb cash on cash: 2.96%

Traditional cash on cash: 2.6%

Airbnb Rental Income: $4130

Traditional Rental Income: $3062

Airbnb ROI: 2.96%