Affordable Homes For Sale in Chester, NY

70 homes

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$239,900
2 Beds
1 Bath
1,084 sqft
2313 Whispering Hills,
Chester, NY 10918
Listing by: R2M Realty Inc
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$269,000
2 Beds
1 Bath
1,084 sqft
1212 Whispering Hills,
Chester, NY 10918
Listing by: Keller Williams Realty
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$275,000
2 Beds
1 Bath
1,084 sqft
2113 Whispering Hills,
Chester, NY 10918
Listing by: Keller Williams Realty
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3D VIEW
$289,000
2 Beds
1 Bath
1,084 sqft
2124 Whispering Hills,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
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OPEN SAT, 1-3PM
3D VIEW
$290,000
2 Beds
1.5 Baths
1,053 sqft
1005 Whispering Hills,
Chester, NY 10918
Listing by: Century 21 Full Service Realty
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$299,000
4 Beds
1 Bath
1,504 sqft
151 Main Street,
Chester, NY 10918
Listing by: Hudson Valley Griffith
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$299,000
2 Beds
1.5 Baths
1,086 sqft
2107 Whispering Hills,
Chester, NY 10918
Listing by: Wansor Realty
5.7 ACRES
$299,000
552 Pine Hill Road,
Chester, NY 10918
Listing by: eRealty Advisors, Inc
COMING SOON 11/9
0.61 ACRES
$299,999
3 Beds
1 Bath
1,046 sqft
14 School Street,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
COMING SOON 11/18
$325,900
2 Beds
1.5 Baths
1,072 sqft
4108 Whispering Hills,
Chester, NY 10918
Listing by: Keller Williams Realty
$339,900
2 Beds
1.5 Baths
1,086 sqft
3706 Whispering Hills,
Chester, NY 10918
Listing by: eXp Realty
46 ACRES
$349,000
492 Black Meadow Road,
Chester, NY 10918
Listing by: eXp Realty
FORECLOSURE
NOTICE OF DEFAULT
3D VIEW
0.94 ACRES
4 Beds
1.5 Baths
1,560 sqft
241 Meadow Avenue,
Chester, NY 10918
Listing by: Keller Williams Realty
$354,900
3 Beds
2.5 Baths
1,331 sqft
2921 Whispering Hills,
Chester, NY 10918
Listing by: ARC Realty 1 in Sales
$355,000
3 Beds
2.5 Baths
1,331 sqft
2522 Whispering Hills,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
FORECLOSURE
BANK OWNED
0.37 ACRES
$360,000
3 Beds
1 Bath
1,561 sqft
33 Meadow Avenue,
Chester, NY 10918
Listing by: River Realty Services, Inc.
5.1 ACRES
$365,000
90 Odyssey Drive,
Chester, NY 10918
Listing by: RE/MAX Town & Country
$370,000
3 Beds
2.5 Baths
1,331 sqft
4704 Whispering Hills,
Chester, NY 10918
Listing by: Sahagian Realty LLC
0.92 ACRES
$399,999
3 Beds
1.5 Baths
1,500 sqft
66 Whitetail Run,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
0.76 ACRES
$419,000
3 Beds
2 Baths
1,357 sqft
70 Main Street,
Chester, NY 10918
Listing by: Curasi Realty, Inc.
0.37 ACRES
$440,000
3 Beds
1.5 Baths
1,728 sqft
1367 Kings Highway,
Chester, NY 10918
Listing by: Greene Realty Group
AUCTION
3D VIEW
0.38 ACRES
$449,000
4 Beds
2 Baths
1,832 sqft
8 Townsend Place,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
OPEN SAT, 12-2PM
0.42 ACRES
$475,000
3 Beds
1.5 Baths
1,848 sqft
3 Mari Road,
Chester, NY 10918
Listing by: Divine Realty NY, LLC
1.8 ACRES
$485,000
3 Beds
2.5 Baths
2,441 sqft
94 Booth Road,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
0.41 ACRES
$499,000
3 Beds
2 Baths
2,000 sqft
7 Townsend Place,
Chester, NY 10918
Listing by: National Veterans Realty Group
OPEN SUN, 12-2PM
0.46 ACRES
$499,999
3 Beds
2.5 Baths
1,908 sqft
11 Chandler Drive,
Chester, NY 10918
Listing by: Coldwell Banker Realty
0.4 ACRES
$499,999
2 Beds
2 Baths
1,910 sqft
19 Meadow Avenue,
Chester, NY 10918
Listing by: RE/MAX Town & Country
0.56 ACRES
$525,000
4 Beds
2.5 Baths
2,698 sqft
24 Walnut Street,
Chester, NY 10918
Listing by: Keller Williams Village Sq Rlt
$549,000
4 Beds
2 Baths
2,824 sqft
147 Main Street,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
1 ACRE
$575,000
6 Beds
2 Baths
68 Conklingtown Road #1&2,
Chester, NY 10918
Listing by: MS Realty Group USA, Inc
3D VIEW
2 ACRES
$599,999
3 Beds
3 Baths
2,902 sqft
3561 Rte 94,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
2.5 ACRES
$634,999
4 Beds
3 Baths
2,316 sqft
424 Laroe Road,
Chester, NY 10918
Listing by: Epique Realty
OPEN SUN, 2:30-4:30PM
6.2 ACRES
$679,000
4 Beds
3.5 Baths
2,960 sqft
5 Red Fox Run,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
1 ACRE
$690,000
4 Beds
2.5 Baths
3,296 sqft
13 Bianca Boulevard,
Chester, NY 10918
Listing by: Keller Williams Realty
3D VIEW
2.3 ACRES
$699,000
5 Beds
3.5 Baths
3,463 sqft
65 Oxford Springs Road,
Chester, NY 10918
Listing by: HomeSmart Homes & Estates
OPEN SAT, 12-3PM
1 ACRE
$699,995
6 Beds
3.5 Baths
4,204 sqft
487 Black Meadow Road,
Chester, NY 10918
Listing by: Joseph Baratta Company Realty
OPEN SUN, 12-2PM
3D VIEW
0.3 ACRES
$719,000
4 Beds
2.5 Baths
3,763 sqft
28 Pewter Circle,
Chester, NY 10918
Listing by: Century 21 Full Service Realty
OPEN SAT, 12:30-2:30PM
$725,000
4 Beds
3 Baths
2,280 sqft
1 Sanford Avenue,
Chester, NY 10918
Listing by: Redfin Real Estate
1.5 ACRES
$739,000
4 Beds
2.5 Baths
2,599 sqft
121 Conklingtown Road,
Chester, NY 10918
Listing by: MS Realty Group USA, Inc
OPEN SAT, 12-3PM
1.6 ACRES
$739,900
4 Beds
3 Baths
3,080 sqft
20 Mountainside Drive,
Chester, NY 10918
Listing by: eXp Realty
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Based on information submitted to the MLS GRID as of 2026-11-06 23:22:57 PST All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Click here for more information

Affordable Homes For Sale in Chester, NY

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