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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
49 Stone Mountain TrailChester, NYStunning 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%
|
206 Greycourt Road #190Chester, 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%
|
16 Lori LaneChester, NYIndulge 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%
|
5 Gabriels DriveChester, NYExquisite 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%
|
90 Main StreetChester, 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%
|
65 Oxford Springs RoadChester, NYWelcome 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%
|
278 Gibson Hill RoadChester, NYAMAZING 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%
|
20 Goshen RoadChester, NYDiscover 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%
|
2503 Whispering HillsChester, NYPRICE 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%
|
507 Bull Mill RoadChester, NYWelcome 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%
|
34 Mountainside DriveChester, NYONE 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%
|
3708 Whispering HillsChester, NYWelcome 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%
|
32 Mountainside DriveChester, NYA 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%
|
11 Saddle Hill RoadChester, 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%
|
2 Pine Hill RoadChester, NYListed 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%
|
2317 Whispering HillsChester, NYWelcome 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%
|
47 Greycourt AvenueChester, NYClassic 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%
|
11 Lakeview DriveChester, NYSplit-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%
|
70 Main StreetChester, NYDiscover the perfect blend of versatility and charm with this exceptional property featuri... |
5 beds | 4 baths | N/A |
$499,000 |
Airbnb cash on cash: 3.68%
|
15 Mari RoadChester, NYMove 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%
|
1711 Kings HighwayChester, NYNestled 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%
|
9 June RoadChester, NYWelcome 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%
|
284 Bull Mill RoadChester, NYMonroe'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%
|
81 Hambletonian RoadChester, NYOWN 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%
|
3915 Whispering HillsChester, NYHighly 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%
|
40 Mountainside DriveChester, NYFANTASTIC 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%
|
Real Estate investment in Chester, NY
There are 26 properties for sale in the city of Chester . The median list price in Chester is $737,000 and the average price per square foot is $283. In September 2025, the average monthly cash on cash return in Chester is 2.00%. The average monthly rental income in Chester is $3,688.