Movoto Real Estate

Homes Under $550K Price For Sale in Chester, NY

50 Homes
 
3706 Whispering Hls, Chester, NY 10918
  • $339,900
  • 2Bd
  • 2Ba
  • 1,086 Sq Ft
New 4 Days
2107 Whispering Hls, Chester, NY 10918
  • $329,000
  • 2Bd
  • 2Ba
  • 1,086 Sq Ft
94 Booth Rd, Chester, NY 10918
  • $525,000
  • 3Bd
  • 3Ba
  • 2,441 Sq Ft
147 Main St, Chester, NY 10918
  • $549,000
  • 4Bd
  • 2Ba
  • 2,824 Sq Ft
1212 Whispering Hls, Chester, NY 10918
  • $269,000
  • 2Bd
  • 1Ba
  • 1,084 Sq Ft
1223 Whispering Hls, Chester, NY 10918
  • $299,900
  • 3Bd
  • 2Ba
  • 1,316 Sq Ft
18 Schueler Rd, Chester, NY 10918
  • $339,900
  • 2Bd
  • 1Ba
  • 960 Sq Ft
19 Meadow Ave, Chester, NY 10918
  • $525,000
  • 2Bd
  • 2Ba
  • 1,910 Sq Ft
L13.5 Joan Court, Chester, NY 12817
  • $49,900
  • 2.38 Acre
8 Townsend Pl, Chester, NY 10918
  • $459,000
  • 4Bd
  • 2Ba
  • 1,832 Sq Ft
Photos coming soon
  • $370,000
  • 3Bd
  • 2Ba
  • 1,316 Sq Ft
4704 Whispering Hls, Chester, NY 10918
  • $370,000
  • 3Bd
  • 3Ba
  • 1,331 Sq Ft
$10K
260 Gibson Hill Rd, Chester, NY 10918
  • $374,900
  • 3Bd
  • 2Ba
  • 1,644 Sq Ft
2921 Whispering Hls, Chester, NY 10918
  • $364,900
  • 3Bd
  • 3Ba
  • 1,331 Sq Ft
$10K
1005 Whispering Hls, Chester, NY 10918
  • $290,000
  • 2Bd
  • 2Ba
  • 1,053 Sq Ft
50 Hambletonian Ave, Chester, NY 10918
  • $550,000
  • 3Bd
  • 2Ba
  • 1,583 Sq Ft
2124 Whispering Hls, Chester, NY 10918
  • $289,000
  • 2Bd
  • 1Ba
  • 1,084 Sq Ft
$10K
75 White Schoolhouse Rd, Chester, NY 12817
  • $285,000
  • 3Bd
  • 2Ba
  • 1,008 Sq Ft
3409 Whispering Hls, Chester, NY 10918
  • $360,000
  • 3Bd
  • 3Ba
  • 1,331 Sq Ft
32 Surrey Rd, Chester, NY 10918
  • $475,000
  • 4Bd
  • 2Ba
  • 1,820 Sq Ft
63 Hubshop Rd, Chester, NY 10918
  • $459,000
  • 4Bd
  • 3Ba
  • 2,060 Sq Ft
1367 Kings Hwy, Chester, NY 10918
  • $440,000
  • 3Bd
  • 2Ba
  • 1,728 Sq Ft
166 Bull Mill Rd, Chester, NY 10918
  • $289,000
  • 2Bd
  • 1Ba
  • 1,004 Sq Ft
$51K
21 Trotting Dr, Chester, NY 10918
  • $475,000
  • 3Bd
  • 2Ba
  • 1,624 Sq Ft
8 Bergman Way, Chester, NY 12860
  • $35,000
  • 2Bd
  • 1Ba
  • 672 Sq Ft
2522 Whispering Hls, Chester, NY 10918
  • $359,000
  • 3Bd
  • 3Ba
  • 1,331 Sq Ft
$10K
66 Whitetail Run, Chester, NY 10918
  • $435,000
  • 3Bd
  • 2Ba
  • 1,500 Sq Ft
Open SAT 12-2
33 Meadow Ave, Chester, NY 10918
  • $370,000
  • 3Bd
  • 1Ba
  • 1,561 Sq Ft
151 Main St, Chester, NY 10918
  • $299,000
  • 4Bd
  • 1Ba
  • 1,504 Sq Ft
$26K
2007 Whispering Hls, Chester, NY 10918
  • $279,999
  • 2Bd
  • 2Ba
  • 1,086 Sq Ft
4008 Whispering Hills Dr, Chester, NY 10918
  • $290,000
  • 2Bd
  • 2Ba
  • 1,072 Sq Ft
7 Lakeview Dr, Chester, NY 10918
  • $549,999
  • 4Bd
  • 3Ba
  • 2,098 Sq Ft
4114 Whispering Hls, Chester, NY 10918
  • $389,900
  • 3Bd
  • 2Ba
  • 1,393 Sq Ft
2604 Whispering Hls, Chester, NY 10918
  • $350,000
  • 3Bd
  • 3Ba
  • 1,086 Sq Ft
241 Meadow Ave, Chester, NY 10918
  • $349,999
  • 4Bd
  • 2Ba
  • 1,560 Sq Ft
$25K
3414 Whispering Hls, Chester, NY 10918
  • $349,999
  • 3Bd
  • 2Ba
  • 1,316 Sq Ft
11 Chandler Dr, Chester, NY 10918
  • $499,999
  • 3Bd
  • 3Ba
  • 1,908 Sq Ft
Open SUN 12-2
4118 Whispering Hills Dr, Chester, NY 10918
  • $329,000
  • 2Bd
  • 2Ba
  • 1,294 Sq Ft
2119 Whispering Hls, Chester, NY 10918
  • $295,000
  • 2Bd
  • 2Ba
  • 1,086 Sq Ft
815 Craigville Rd, Chester, NY 10918
  • $280,000
  • 3Bd
  • 1Ba
  • 2,016 Sq Ft
3318 State Route 94, Chester, NY 10918
  • $549,900
  • 3Bd
  • 2Ba
  • 2,138 Sq Ft
24 Walnut St, Chester, NY 10918
  • $525,000
  • 4Bd
  • 3Ba
  • 2,698 Sq Ft
$14K
3815 Whispering Hills Dr, Chester, NY 10918
  • $370,000
  • 3Bd
  • 3Ba
  • 1,331 Sq Ft
527 Potter Brook Rd, Chester, NY 12817
  • $329,900
  • 3Bd
  • 2Ba
  • 1,960 Sq Ft
$10K
2820 Whispering Hls, Chester, NY 10918
  • $319,900
  • 2Bd
  • 2Ba
  • 1,072 Sq Ft
35 Maple Ave, Chester, NY 10918
  • $489,900
  • 3Bd
  • 3Ba
  • 2,032 Sq Ft
1311 Whispering Hls, Chester, NY 10918
  • $329,900
  • 3Bd
  • 2Ba
  • 1,316 Sq Ft
5 N Hudson St, Chester, NY 10918
  • $500,000
  • 3Bd
  • 2Ba
  • 2,688 Sq Ft
7 Hambletonian Ave, Chester, NY 10918
  • $379,900
  • 2Bd
  • 1Ba
  • 1,026 Sq Ft
2113 Whispering Hls, Chester, NY 10918
  • $275,000
  • 2Bd
  • 1Ba
  • 1,084 Sq Ft
$20K
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Chester, NY real estate market trends

Statistics as of October 2026
$599K
Avg. list price
$266/Sqft
Avg. price/sqft
106
Homes for sale
2,138 Sqft
Avg. home size
63 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.
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