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Chester town, NY - single-family homes for sale
29 of 29 results displayed
- New
$360,000Active3 beds 2 baths1,460 sq. ft.4 Maple Lane, Monroe, NY 10950
MLS# 965315Listed by: FLAG REALTY GROUP - New
$879,900Active4 beds 3 baths3,200 sq. ft.1414 Kings Highway, Chester, NY 10918
MLS# 965992Listed by: KELLER WILLIAMS REALTY - New
$449,900Active2 beds 2 baths1,998 sq. ft.31 Hudson Street, Chester, NY 10918
MLS# 963657Listed by: BHG REAL ESTATE GREEN TEAM - New
$499,999Active3 beds 2 baths1,460 sq. ft.35 Maple Lane, Monroe, NY 10950
MLS# 965197Listed by: EXP REALTY - New
$850,000Active4 beds 3 baths3,120 sq. ft.558 Pine Hill Road, Chester, NY 10918
MLS# 958731Listed by: EREALTY ADVISORS, INC - New
$425,000Active2 beds 1 baths1,026 sq. ft.7 Hambletonian Avenue, Chester, NY 10918
MLS# 964090Listed by: HOMESMART HOMES & ESTATES 
$849,999Active5 beds 6 baths5,403 sq. ft.4 Debbie Court, Chester, NY 10918
MLS# 962813Listed by: FLAG REALTY GROUP
$720,000Active4 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- Coming Soon
$580,000Coming Soon4 beds 3 baths150 Lake Region Boulevard, Monroe, NY 10950
MLS# 955186Listed by: HUDSON VALLEY HOME CONNECTION 
$465,000Active4 beds 2 baths1,932 sq. ft.3 Tulip Lane, Monroe, NY 10950
MLS# 954439Listed by: ETHOS REALTY LLC
$460,000Active3 beds 2 baths1,728 sq. ft.1367 Kings Highway, Chester, NY 10918
MLS# 951876Listed by: KARTEN REAL ESTATE SVCS LLC
$449,000Active4 beds 2 baths1,780 sq. ft.108 Pine Hill Road, Chester, NY 10918
MLS# 944582Listed by: AVION
$499,900Pending3 beds 3 baths1,934 sq. ft.6 Vista Drive, Chester, NY 10918
MLS# 944968Listed by: KELLER WILLIAMS REALTY
$600,000Pending3 beds 2 baths1,876 sq. ft.44 Cedar Pond Lane, Chester, NY 10918
MLS# 942578Listed by: EXP REALTY
$425,000Pending4 beds 3 baths2,090 sq. ft.16 Oakland Avenue, Chester, NY 10918
MLS# 939522Listed by: BHG REAL ESTATE GREEN TEAM
$299,900Pending3 beds 3 baths1,331 sq. ft.2104 Whispering Hills, Chester, NY 10918
MLS# 936624Listed by: ARC REALTY 1 IN SALES
$874,400Active4 beds 2 baths2,466 sq. ft.651 Lakes Road, Monroe, NY 10950
MLS# 929552Listed by: HOWARD HANNA RAND 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.
$559,000Pending4 beds 3 baths2,288 sq. ft.12 Juniper Lane, Monroe, NY 10950
MLS# 904879Listed by: HOULIHAN LAWRENCE 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
$509,999Pending3 beds 2 baths1,800 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
Local realty services provided by:CENTURY 21 ICON
Neighborhoods near Chester town, NY
Zip codes near Chester town, NY
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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.
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 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.