Cheap Homes For Sale in Town of Chester, NY

47 homes

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FORECLOSURE
BANK OWNED
$215,000
2 Beds
1.5 Baths
1,240 sqft
503 Mountain Laurel Drive,
Monroe, NY 10950
Listing by: ARC Realty 1 in Sales
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3D VIEW
$260,000
2 Beds
1 Bath
1,084 sqft
1401 Whispering Hills,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
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AUCTION
Est. $298,400
2 Beds
2 Baths
1,086 sqft
1206 Whispering Hls #151,
Chester, NY 10918
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$319,900
2 Beds
1.5 Baths
1,072 sqft
2820 Whispering Hills,
Chester, NY 10918
Listing by: R2M Realty Inc.
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$319,900
3 Beds
2.5 Baths
1,320 sqft
607 Mountain Laurel Drive,
Monroe, NY 10950
Listing by: Weichert Realtors
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$344,900
3 Beds
2 Baths
1,316 sqft
1311 Whispering Hills,
Chester, NY 10918
Listing by: Keller Williams Realty
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$370,000
3 Beds
2.5 Baths
1,331 sqft
3815 Whispering Hills Drive,
Chester, NY 10918
Listing by: MK Realty Inc
$377,000
3 Beds
2.5 Baths
1,331 sqft
1221 Whispering Hls,
Chester, NY 10918
Listing by: BUY NY REALTY LLC
0.29 ACRES
$399,900
2 Beds
1 Bath
1,026 sqft
7 Hambletonian Avenue,
Chester, NY 10918
Listing by: HomeSmart Homes & Estates
FORECLOSURE
BANK OWNED
0.37 ACRES
$400,000
3 Beds
1 Bath
1,561 sqft
33 Meadow Avenue,
Chester, NY 10918
Listing by: River Realty Services, Inc.
NEW
COMING SOON 6/6
$419,000
3 Beds
2.5 Baths
1,694 sqft
332 Heritage Lane,
Monroe, NY 10950
Listing by: RE/MAX Prime Properties
$425,000
3 Beds
2.5 Baths
1,331 sqft
2722 Whispering Hills,
Chester, NY 10918
Listing by: Artisan Realty
0.45 ACRES
$450,000
3 Beds
1.5 Baths
1,177 sqft
151 Laroe Road,
Chester, NY 10918
Listing by: Keller Williams Realty
$460,000
3 Beds
1.5 Baths
1,728 sqft
1367 Kings Highway,
Chester, NY 10918
Listing by: Karten Real Estate Svcs LLC
NEW - 2 DAYS AGO
0.29 ACRES
$475,000
3 Beds
2 Baths
1,460 sqft
35 Maple Lane,
Monroe, NY 10950
Listing by: eXp Realty
0.64 ACRES
$495,000
4 Beds
3 Baths
1,792 sqft
18 Southside Drive,
Monroe, NY 10950
Listing by: Keller Williams Realty
0.36 ACRES
$499,900
3 Beds
2 Baths
1,778 sqft
1 N Hudson Street,
Chester, NY 10918
Listing by: Keller Williams Hudson Valley
0.38 ACRES
$500,000
3 Beds
2 Baths
2,688 sqft
5 N Hudson Street,
Chester, NY 10918
Listing by: Keller Williams Realty
0.26 ACRES
$529,900
3 Beds
3 Baths
2,032 sqft
35 Maple Avenue,
Chester, NY 10918
Listing by: RE/MAX Benchmark Realty Group
1 ACRE
$550,000
5 Beds
2.5 Baths
1,815 sqft
208 Glenmere Road,
Chester, NY 10918
Listing by: MK Realty Inc
$559,000
4 Beds
2.5 Baths
1,916 sqft
22 Cambridge Circle,
Monroe, NY 10950
Listing by: Howard Hanna Rand Realty
3D VIEW
$569,000
4 Beds
2.5 Baths
2,112 sqft
150 Lake Region Boulevard,
Monroe, NY 10950
Listing by: Hudson Valley Home Connection
3D VIEW
0.51 ACRES
$569,000
4 Beds
2.5 Baths
2,040 sqft
78 Pickerel Road,
Monroe, NY 10950
Listing by: eXp Realty
OPEN SAT, 1-2PM
COMING SOON 5/27
1.8 ACRES
$590,000
3 Beds
2.5 Baths
2,083 sqft
94 Booth Road,
Chester, NY 10918
Listing by: Compass Greater NY, LLC
0.41 ACRES
$599,000
4 Beds
2 Baths
2,056 sqft
6 Adams Court,
Monroe, NY 10950
Listing by: Keller Williams Realty
0.43 ACRES
$600,000
5 Beds
3 Baths
2,983 sqft
9 Mount Ridge Court,
Monroe, NY 10950
Listing by: RE/MAX Benchmark Realty Group
3D VIEW
1.3 ACRES
$670,000
4 Beds
3 Baths
3,636 sqft
10 Hidden Drive,
Monroe, NY 10950
Listing by: Century 21 Full Service Realty
1.8 ACRES
$699,000
4 Beds
2.5 Baths
3,120 sqft
558 Pine Hill Road,
Chester, NY 10918
Listing by: eRealty Advisors, Inc
NEW CONSTRUCTION
1 ACRE
$699,990
4 Beds
3 Baths
1,867 sqft
34 Mountainside Drive,
Chester, NY 10918
Listing by: Our House Real Estate Group
1 ACRE
$725,000
6 Beds
3.5 Baths
4,204 sqft
487 Black Meadow Road,
Chester, NY 10918
Listing by: Joseph Baratta Company Realty
NEW CONSTRUCTION
0.53 ACRES
$759,900
4 Beds
2.5 Baths
2,250 sqft
90 Pewter Circle,
Chester, NY 10918
Listing by: Keller Williams Realty
NEW
COMING SOON 5/29
1 ACRE
$779,000
4 Beds
3.5 Baths
2,948 sqft
270 Bull Mill Road,
Chester, NY 10918
Listing by: Keller Williams Realty
5.4 ACRES
$799,000
5 Beds
5.5 Baths
5,403 sqft
4 Debbie Court,
Chester, NY 10918
Listing by: Flag Realty Group
OPEN SUN, 12-2PM
1.3 ACRES
$799,999
3 Beds
2.5 Baths
2,718 sqft
58 Nancy Lane,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
1 ACRE
$849,900
3 Beds
3 Baths
2,740 sqft
149 Creamery Pond Road,
Chester, NY 10918
Listing by: Keller Williams Realty
NEW CONSTRUCTION
0.62 ACRES
$849,900
4 Beds
2.5 Baths
3,200 sqft
Lot 3 - 62 Camp Monroe Road,
Monroe, NY 10950
Listing by: Howard Hanna Rand Realty
NEW CONSTRUCTION
20.18 ACRES
$849,900
4 Beds
2.5 Baths
2,603 sqft
32 Mountainside Drive,
Chester, NY 10918
Listing by: Our House Real Estate Group
NEW CONSTRUCTION
1.6 ACRES
$869,900
4 Beds
2.5 Baths
3,000 sqft
10 Wells Sweep Lane,
Chester, NY 10918
Listing by: Keller Williams Realty
0.5 ACRES
$875,000
3 Beds
2.5 Baths
2,302 sqft
2 Pine Hill Road,
Chester, NY 10918
Listing by: Ellis Sotheby's Intl Realty
NEW CONSTRUCTION
4.5 ACRES
$879,900
4 Beds
2.5 Baths
3,200 sqft
1414 Kings Highway,
Chester, NY 10918
Listing by: Keller Williams Realty
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Based on information submitted to the MLS GRID as of 2026-02-06 15:18:24 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

Cheap Homes For Sale in Town of Chester, NY

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