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Homes Recently Sold in Chester, NY | Page 4

339 Homes
 
138 Dug Rd, Chester, NY 10918
  • $700,000
  • 4Bd
  • 3Ba
  • 2,452 Sq Ft
SOLD
157 Creamery Pond Rd, Chester, NY 10918
  • $875,000
  • 4Bd
  • 4Ba
  • 4,021 Sq Ft
SOLD
4706 Whispering Hls, Chester, NY 10918
  • $310,000
  • 2Bd
  • 2Ba
  • 1,086 Sq Ft
SOLD
55 Hudson St, Chester, NY 10918
  • $460,000
  • 3Bd
  • 2Ba
  • 1,576 Sq Ft
SOLD
118 Murray Dr, Chester, NY 10918
  • $800,000
  • 5Bd
  • 4Ba
  • 3,418 Sq Ft
SOLD
7 Garden St, Chester, NY 10918
  • $400,000
  • 3Bd
  • 2Ba
  • 1,435 Sq Ft
SOLD
20 Hubshop Rd, Chester, NY 10918
  • $624,000
  • 4Bd
  • 3Ba
  • 2,236 Sq Ft
SOLD
18 Miller Dr, Chester, NY 10918
  • $415,000
  • 3Bd
  • 1Ba
  • 1,144 Sq Ft
SOLD
4401 Whispering Hills Dr, Chester, NY 10918
  • $290,000
  • 2Bd
  • 1Ba
  • 1,118 Sq Ft
SOLD
151 Kings Highway Byp, Chester, NY 10918
  • $1,450,000
  • 4Bd
  • 5Ba
  • 5,638 Sq Ft
SOLD
142 Laroe Rd, Chester, NY 10918
  • $607,700
  • 5Bd
  • 4Ba
  • 3,385 Sq Ft
SOLD
3 Woodridge Dr, Chester, NY 10918
  • $763,750
  • 4Bd
  • 3Ba
  • 2,500 Sq Ft
SOLD
11 N Hudson St, Chester, NY 10918
  • $475,000
  • 3Bd
  • 2Ba
  • 1,500 Sq Ft
SOLD
4120 Whispering Hills Dr, Chester, NY 10918
  • $338,000
  • 2Bd
  • 2Ba
  • 1,282 Sq Ft
SOLD
2 Bell Way, Chester, NY 10918
  • $609,000
  • 3Bd
  • 3Ba
  • 2,032 Sq Ft
SOLD
16 Spectrum Dr, Chester, NY 10918
  • $750,000
  • 3Bd
  • 4Ba
  • 2,276 Sq Ft
SOLD
1213 Whispering Hls, Chester, NY 10918
  • $270,000
  • 2Bd
  • 1Ba
  • 1,084 Sq Ft
SOLD
21 Angle Dr, Chester, NY 10918
  • $350,000
  • 4Bd
  • 3Ba
  • 2,953 Sq Ft
SOLD
1301 Kings Hwy, Chester, NY 10918
  • $617,000
  • 4Bd
  • 3Ba
  • 2,676 Sq Ft
SOLD
2706 Whispering Hls, Chester, NY 10918
  • $315,000
  • 2Bd
  • 2Ba
  • 1,086 Sq Ft
SOLD
8 Country Woods Dr, Chester, NY 10918
  • $700,000
  • 5Bd
  • 3Ba
  • 3,120 Sq Ft
SOLD
16 Fernglade Ct, Chester, NY 10918
  • $550,000
  • 4Bd
  • 3Ba
  • 3,327 Sq Ft
SOLD
69 High St, Chester, NY 10918
  • $560,000
  • 3Bd
  • 3Ba
  • 2,092 Sq Ft
SOLD
154 Hambletonian Rd, Chester, NY 10918
  • $1,350,000
  • 4Bd
  • 4Ba
  • 4,350 Sq Ft
SOLD
3111 Whispering Hills Dr, Chester, NY 10918
  • $339,000
  • 3Bd
  • 2Ba
  • 1,316 Sq Ft
SOLD
16 Kerner Dr, Chester, NY 10918
  • $405,000
  • 3Bd
  • 1Ba
  • 1,222 Sq Ft
SOLD
397 Bellvale Rd, Chester, NY 10918
  • $475,000
  • 2Bd
  • 2Ba
  • 1,452 Sq Ft
SOLD
16 Academy Ave, Chester, NY 10918
  • $453,000
  • 3Bd
  • 2Ba
  • 2,358 Sq Ft
SOLD
2 Fields Ln, Chester, NY 10918
  • $415,000
  • 3Bd
  • 3Ba
  • 2,604 Sq Ft
SOLD
L14 Panther Mountain Drive, Chester, NY 12817
  • $75,000
  • 1.8 Acre
SOLD
152 Gibson Hill Rd, Chester, NY 10918
  • $782,000
  • 4Bd
  • 3Ba
  • 3,176 Sq Ft
SOLD
137 Creamery Pond Rd, Chester, NY 10918
  • $750,000
  • 4Bd
  • 3Ba
  • 2,822 Sq Ft
SOLD
14 Mari Rd, Chester, NY 10918
  • $460,000
  • 3Bd
  • 2Ba
  • 1,926 Sq Ft
SOLD
2607 Whispering Hls, Chester, NY 10918
  • $325,000
  • 2Bd
  • 2Ba
  • 1,086 Sq Ft
SOLD
2 Grand View Ter, Chester, NY 10918
  • $749,900
  • 4Bd
  • 3Ba
  • 3,480 Sq Ft
SOLD
76 Restdale Rd, Chester, NY 10918
  • $715,000
  • 4Bd
  • 3Ba
  • 2,838 Sq Ft
SOLD
6 Silvertail Rd, Chester, NY 10918
  • $1,247,500
  • 6Bd
  • 5Ba
  • 5,127 Sq Ft
SOLD
18 Academy Ave, Chester, NY 10918
  • $420,000
  • —Bd
  • —Ba
SOLD
204 Farmingdale Rd, Chester, NY 10918
  • $581,000
  • 2Bd
  • 2Ba
  • 2,067 Sq Ft
SOLD
220 Glenmere Rd, Chester, NY 10918
  • $490,900
  • 3Bd
  • 2Ba
  • 1,268 Sq Ft
SOLD
2910 Whispering Hls, Chester, NY 10918
  • $355,000
  • 3Bd
  • 3Ba
  • 1,331 Sq Ft
SOLD
14 Country Woods Dr, Chester, NY 10918
  • $720,000
  • 5Bd
  • 4Ba
  • 3,955 Sq Ft
SOLD
3 Seely Rd, Chester, NY 10918
  • $520,000
  • 4Bd
  • 3Ba
  • 2,208 Sq Ft
SOLD
14 Twin Brooks Dr, Chester, NY 10918
  • $475,000
  • 4Bd
  • 2Ba
  • 1,692 Sq Ft
SOLD
1107 Whispering Hls, Chester, NY 10918
  • $273,000
  • 2Bd
  • 2Ba
  • 1,086 Sq Ft
SOLD
86 Brimstone Mountain Rd, Chester, NY 10918
  • $565,000
  • 3Bd
  • 2Ba
  • 1,817 Sq Ft
SOLD
156 Oxford Rd, Chester, NY 10918
  • $410,000
  • 3Bd
  • 2Ba
  • 2,350 Sq Ft
SOLD
9 Laroc Rd, Chester, NY 10918
  • $565,000
  • 3Bd
  • 3Ba
  • 1,810 Sq Ft
SOLD
240 Renies Rd, Chester, NY 10918
  • $600,000
  • 4Bd
  • 4Ba
  • 3,097 Sq Ft
SOLD
1807 Whispering Hls, Chester, NY 10918
  • $285,000
  • 2Bd
  • 2Ba
  • 1,086 Sq Ft
SOLD
151 - 200 of 339 Homes in Chester, NY
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Chester, NY real estate market trends

Statistics as of November 2026
$684K
Avg. list price
$266/Sqft
Avg. price/sqft
94
Homes for sale
2,599 Sqft
Avg. home size
77 Days
Avg. days on market
Movoto makes it easy to track market trends in Chester, NY. Whether you’re entering the market or planning your next move, understanding these key metrics can guide smart decisions. Looking for more detailed housing market stats in Chester, NY?
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Frequently Asked Questions about Chester, NY

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The data relating to real estate for sale on this web site comes in part from the OneKey® MLS. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) nor the website owner shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Property locations as displayed on any map are best approximations only and exact locations should be independently verified. IDX information is provided exclusively for consumers personal non-commercial use and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.©2026 OneKey® MLS. All rights reserved. Fair Housing Notice
Standardized Operating Procedures for the Prerequisites Prospective Homebuyers: (1) Perspective clients will not be required to verify their identity during the home purchase process by providing government issued identification. (2) An exclusive broker agreement will not be required on an individual property basis. Or, a specific period of time in order to assist perspective home buyers. (3) In the event a home buyer will be using a mortgage loan to facilitate the purchase of a property. The home buyer will be required to provide proof of pre-approval. (4) In the event the perspective home buyer will be purchasing in all cash. The buyer will be required to provide proof of funds before the submission of an offer.
©2026 Global Multiple Listing Service, Inc. The data relating to real estate on this website comes in part from the Internet Data Exchange program of the GMLS. All information is deemed reliable but not guaranteed and should be independently verified. All properties subject to prior sale, change, or withdrawal. Neither listing broker(s), GMLS shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless from any damages arising from reliance upon these data. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties they may be interested in purchasing. Fair Housing Notice
Standardized Operating Procedures for the Prerequisites Prospective Homebuyers: (1) Perspective clients will not be required to verify their identity during the home purchase process by providing government issued identification. (2) An exclusive broker agreement will not be required on an individual property basis. Or, a specific period of time in order to assist perspective home buyers. (3) In the event a home buyer will be using a mortgage loan to facilitate the purchase of a property. The home buyer will be required to provide proof of pre-approval. (4) In the event the perspective home buyer will be purchasing in all cash. The buyer will be required to provide proof of funds before the submission of an offer.
The data relating to real estate for sale on this web site comes in part from the Hudson Valley Catskill Region MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information deemed reliable but not guaranteed and should be independently verified. Copyright 2026 by the Hudson Valley Catskill Region MLS. All Rights Reserved. Fair Housing Notice
Standardized Operating Procedures for the Prerequisites Prospective Homebuyers: (1) Perspective clients will not be required to verify their identity during the home purchase process by providing government issued identification. (2) An exclusive broker agreement will not be required on an individual property basis. Or, a specific period of time in order to assist perspective home buyers. (3) In the event a home buyer will be using a mortgage loan to facilitate the purchase of a property. The home buyer will be required to provide proof of pre-approval. (4) In the event the perspective home buyer will be purchasing in all cash. The buyer will be required to provide proof of funds before the submission of an offer.
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