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 |
|---|---|---|---|
6 Moffatt LaneChester, NYDiscover an exceptional income-generating two-family home nestled in the Village of Cheste... |
5 beds | 3 baths | 1,888 sq.ft. |
$499,000 |
Airbnb cash on cash: 3.16%
|
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. |
$849,900 |
Airbnb cash on cash: 0.72%
|
33 Meadow AvenueChester, NYOne 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%
|
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. |
$723,000 |
Airbnb cash on cash: 1.28%
|
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. |
$845,000 |
Airbnb cash on cash: 0.3%
|
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. |
$1,160,000 |
Airbnb cash on cash: -0.67%
|
70 Main StreetChester, NYDiscover 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%
|
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: 0.74%
|
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: 0.14%
|
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: -0.46%
|
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: 0.14%
|
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: -0.58%
|
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. |
$674,999 |
Airbnb cash on cash: 0.34%
|
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. |
$699,990 |
Airbnb cash on cash: 1.51%
|
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. |
$425,000 |
Airbnb cash on cash: 3.9%
|
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: 2.58%
|
2 Dawn CourtChester, NYSpectacular 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%
|
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: 1.22%
|
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: 3.06%
|
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: 0.21%
|
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: 1.39%
|
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: 1.24%
|
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: 1.08%
|
22 Bridle LaneChester, NYThis 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%
|
48 Brennan CourtChester, NYWelcome 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%
|
Real Estate investment in Chester, NY
There are 25 properties for sale in the city of Chester . The median list price in Chester is $699,900 and the average price per square foot is $281. In October 2025, the average monthly cash on cash return in Chester is 3.00%. The average monthly rental income in Chester is $3,775.