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Chester town, NY - homes for sale
47 of 47 results displayed
- Coming Soon
$650,000Coming Soon5 beds 3 baths9 Mount Ridge Court, Monroe, NY 10950
MLS# 951183Listed by: RE/MAX BENCHMARK REALTY GROUP - New
$350,000Active2 beds 1 baths1,272 sq. ft.307 Gibson Hill Road, Chester, NY 10918
MLS# 968972Listed by: HOWARD HANNA RAND REALTY - New
$370,000Active3 beds 3 baths1,331 sq. ft.2203 Whispering Hills, Chester, NY 10918
MLS# 954443Listed by: HOWARD HANNA RAND REALTY 
$360,000Active3 beds 2 baths1,460 sq. ft.4 Maple Lane, Monroe, NY 10950
MLS# 965315Listed by: FLAG REALTY GROUP
$879,900Active4 beds 3 baths3,200 sq. ft.1414 Kings Highway, Chester, NY 10918
MLS# 965992Listed by: KELLER WILLIAMS REALTY
Listed by BHGRE$449,900Active2 beds 2 baths1,998 sq. ft.31 Hudson Street, Chester, NY 10918
MLS# 963657Listed by: BHG REAL ESTATE GREEN TEAM
$499,999Active3 beds 2 baths1,460 sq. ft.35 Maple Lane, Monroe, NY 10950
MLS# 965197Listed by: EXP REALTY
$350,000Active5.7 Acres552 Pine Hill Road, Chester, NY 10918
MLS# 958740Listed by: EREALTY ADVISORS, INC
$249,900Active2 beds 2 baths1,053 sq. ft.1005 Whispering Hills, Chester, NY 10918
MLS# 964957Listed by: ARC REALTY 1 IN SALES
$850,000Active4 beds 3 baths3,120 sq. ft.558 Pine Hill Road, Chester, NY 10918
MLS# 958731Listed by: EREALTY ADVISORS, INC
$149,900Active0.2 Acres2 Imperial Park, Chester, NY 10918
MLS# 964115Listed by: HOMESMART HOMES & ESTATES
$425,000Active2 beds 1 baths1,026 sq. ft.7 Hambletonian Avenue, Chester, NY 10918
MLS# 964090Listed by: HOMESMART HOMES & ESTATES
$279,900Pending2 beds 1 baths1,084 sq. ft.2913 Whispering Hills, Chester, NY 10918
MLS# 962709Listed by: HOMESMART HOMES & ESTATES
$849,999Active5 beds 6 baths5,403 sq. ft.4 Debbie Court, Chester, NY 10918
MLS# 962813Listed by: FLAG REALTY GROUP
$699,000Active4 beds 3 baths2,506 sq. ft.34 Booth Road, Chester, NY 10918
MLS# 961100Listed by: CENTURY 21 FULL SERVICE REALTY
$725,000Active6 beds 4 baths4,204 sq. ft.487 Black Meadow Road, Chester, NY 10918
MLS# 960665Listed by: JOSEPH BARATTA COMPANY REALTY
$339,900Active3 beds 3 baths1,320 sq. ft.607 Mountain Laurel Drive, Monroe, NY 10950
MLS# 961136Listed by: WEICHERT REALTORS
$309,900Active2 beds 1 baths792 sq. ft.111 Lake Region Boulevard, Monroe, NY 10950
MLS# 957716Listed by: KELLER WILLIAMS VALLEY REALTY
$635,000Pending3 beds 3 baths1,954 sq. ft.25 Sugarloaf Mountain Road, Chester, NY 10918
MLS# 951920Listed by: CRONIN & COMPANY REAL ESTATE
$580,000Active4 beds 3 baths2,112 sq. ft.150 Lake Region Boulevard, Monroe, NY 10950
MLS# 955186Listed by: HUDSON VALLEY HOME CONNECTION
$450,000Active4 beds 2 baths1,932 sq. ft.3 Tulip Lane, Monroe, NY 10950
MLS# 954439Listed by: ETHOS REALTY LLC
$675,000Active2 Acres50 Elkay Drive, Chester, NY 10918
MLS# 954329Listed by: POINT REALTY USA
$460,000Active3 beds 2 baths1,728 sq. ft.1367 Kings Highway, Chester, NY 10918
MLS# 951876Listed by: KARTEN REAL ESTATE SVCS LLC
$299,999Pending2 beds 2 baths1,072 sq. ft.4508 Whispering Hills, Chester, NY 10918
MLS# 951306Listed by: EXP REALTY
$295,000Active2 beds 1 baths1,084 sq. ft.2113 Whispering Hills, Chester, NY 10918
MLS# 950534Listed by: KELLER WILLIAMS REALTY
$500,000Active9.78 Acres30 Harding Way, Monroe, NY 10950
MLS# 950482Listed by: KELLER WILLIAMS REALTY
$444,000Active4 beds 2 baths1,780 sq. ft.108 Pine Hill Road, Chester, NY 10918
MLS# 944582Listed by: AVION
$289,000Pending2 beds 2 baths1,072 sq. ft.3308 Whispering Hills Drive, Chester, NY 10918
MLS# 924165Listed by: HOWARD HANNA RAND REALTY
$299,000Pending2 beds 2 baths1,072 sq. ft.3120 Whispering Hills, Chester, NY 10918
MLS# 941582Listed by: JOHN J LEASE REALTORS INC
$305,000Active2 beds 2 baths1,072 sq. ft.3917 Whispering Hills, Chester, NY 10918
MLS# 942965Listed by: KELLER WILLIAMS HUDSON VALLEY
$239,900Active2 beds 2 baths1,240 sq. ft.503 Mountain Laurel Drive, Monroe, NY 10950
MLS# 942812Listed by: ARC REALTY 1 IN SALES
Listed by BHGRE$425,000Pending4 beds 3 baths2,090 sq. ft.16 Oakland Avenue, Chester, NY 10918
MLS# 939522Listed by: BHG REAL ESTATE GREEN TEAM
$309,900Pending3 beds 3 baths1,331 sq. ft.1503 Whispering Hills, Chester, NY 10918
MLS# 937839Listed by: CENTURY 21 E & M WILLIAMS RLTY
$289,500Active2 beds 1 baths1,084 sq. ft.1401 Whispering Hills, Chester, NY 10918
MLS# 935471Listed by: HOWARD HANNA RAND REALTY
$874,400Active4 beds 2 baths2,466 sq. ft.651 Lakes Road, Monroe, NY 10950
MLS# 929552Listed by: HOWARD HANNA RAND REALTY
$369,000Pending3 beds 3 baths1,331 sq. ft.2915 Whispering Hills, Chester, NY 10918
MLS# 927990Listed by: CENTURY 21 FULL SERVICE REALTY
$730,000Active4 beds 4 baths2,780 sq. ft.7 Park Place, Chester, NY 10918
MLS# 927218Listed by: CENTURY 21 FULL SERVICE REALTY
$475,000Active4 beds 3 baths1,357 sq. ft.70 Main Street, Chester, NY 10918
MLS# 914556Listed by: KELLER WILLIAMS HUDSON VALLEY
$400,000Active3 beds 1 baths1,561 sq. ft.33 Meadow Avenue, Chester, NY 10918
MLS# 907272Listed by: RIVER REALTY SERVICES, INC.
$849,900Active4 beds 3 baths2,603 sq. ft.32 Mountainside Drive, Chester, NY 10918
MLS# 901144Listed by: OUR HOUSE REAL ESTATE GROUP
$699,990Active4 beds 3 baths1,867 sq. ft.34 Mountainside Drive, Chester, NY 10918
MLS# 956879Listed by: OUR HOUSE REAL ESTATE GROUP
$509,999Pending2 beds 2 baths1,714 sq. ft.391 Bull Mill Road, Chester, NY 10918
MLS# 880804Listed by: CENTURY 21 REALTY CENTER
$1,100,000Active4 beds 4 baths4,467 sq. ft.53 Odyssey Drive, Chester, NY 10918
MLS# 881474Listed by: HOWARD HANNA RAND REALTY
$350,000Active5.1 AcresOdyssey Drive, Chester, NY 10918
MLS# 858370Listed by: KELLER WILLIAMS REALTY
$259,000Active20.18 Acres32 Mountainside Drive, Chester, NY 10918
MLS# H6328761Listed by: OUR HOUSE REAL ESTATE GROUP
$225,000Active1 Acres34 Mountainside Drive, Chester, NY 10918
MLS# H6326715Listed by: OUR HOUSE REAL ESTATE GROUP
$500,000Pending0.83 AcresMain Street, Chester, NY 10918
MLS# H6204360Listed by: KELLER WILLIAMS REALTY
Local realty services provided by:Better Homes and Gardens Real Estate Choice Realty
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© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.