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Chester town, NY - homes for sale
52 of 52 results displayed
- New
$635,000Active3 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 - New
$465,000Active4 beds 2 baths1,932 sq. ft.3 Tulip Lane, Monroe, NY 10950
MLS# 954439Listed by: ETHOS REALTY LLC - New
$699,000Active2 Acres50 Elkay Drive, Chester, NY 10918
MLS# 954329Listed by: POINT REALTY USA - New
$1,399,999Active4 beds 4 baths4,508 sq. ft.145 Kings Highway Bypass, Chester, NY 10918
MLS# 953574Listed by: KELLER WILLIAMS REALTY 
$460,000Active3 beds 2 baths1,728 sq. ft.1367 Kings Highway, Chester, NY 10918
MLS# 951876Listed by: KARTEN REAL ESTATE SVCS LLC
$710,000Active4 beds 3 baths2,000 sq. ft.1 Hillview Terrace, Chester, NY 10918
MLS# 2600369Listed by: ROBERT DEFALCO REALTY, INC.- Open Sun, 12 to 2pm
$299,999Active2 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
$449,000Active4 beds 2 baths1,780 sq. ft.108 Pine Hill Road, Chester, NY 10918
MLS# 944582Listed by: AVION- Open Sat, 11am to 1pm
$289,000Active2 beds 2 baths1,072 sq. ft.3308 Whispering Hills Drive, Chester, NY 10918
MLS# 924165Listed by: HOWARD HANNA RAND REALTY 
$299,000Active2 beds 2 baths1,072 sq. ft.3120 Whispering Hills, Chester, NY 10918
MLS# 941582Listed by: JOHN J LEASE REALTORS INC
$319,000Active2 beds 2 baths1,072 sq. ft.3917 Whispering Hills, Chester, NY 10918
MLS# 942965Listed by: KELLER WILLIAMS HUDSON VALLEY
$600,000Pending3 beds 2 baths1,876 sq. ft.44 Cedar Pond Lane, Chester, NY 10918
MLS# 942578Listed by: EXP REALTY
$261,250Active2 beds 2 baths1,240 sq. ft.503 Mountain Laurel Drive, Monroe, NY 10950
MLS# 942812Listed by: ARC REALTY 1 IN SALES
$650,000Pending4 beds 3 baths2,318 sq. ft.23 Pewter Circle, Chester, NY 10918
MLS# 939836Listed 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
$309,900Active3 beds 3 baths1,331 sq. ft.1503 Whispering Hills, Chester, NY 10918
MLS# 937839Listed by: CENTURY 21 E & M WILLIAMS RLTY
$534,900Pending3 beds 3 baths1,946 sq. ft.80 Pewter Circle, Chester, NY 10918
MLS# 913254Listed by: BHG REAL ESTATE GREEN TEAM
$290,000Pending2 beds 1 baths1,084 sq. ft.2812 Whispering Hills, Chester, NY 10918
MLS# 936470Listed by: EXIT REALTY CONNECTIONS
$304,900Pending2 beds 1 baths1,084 sq. ft.2912 Whispering Hills, Chester, NY 10918
MLS# 937375Listed by: KELLER WILLIAMS REALTY
$299,900Pending3 beds 3 baths1,331 sq. ft.2104 Whispering Hills, Chester, NY 10918
MLS# 936624Listed by: ARC REALTY 1 IN SALES
$289,500Active2 beds 1 baths1,084 sq. ft.1401 Whispering Hills, Chester, NY 10918
MLS# 935471Listed by: HOWARD HANNA RAND REALTY
$324,000Pending4 beds 2 baths1,760 sq. ft.3 Hickory Lane, Monroe, NY 10950
MLS# 935454Listed by: BLOOMING REALTY
$345,000Pending3 beds 1 baths1,120 sq. ft.65 Hudson Street, Chester, NY 10918
MLS# 934146Listed by: KELLER WILLIAMS REALTY
$875,000Active3 beds 3 baths2,302 sq. ft.2 Pine Hill Road, Chester, NY 10918
MLS# 933779Listed by: SHAHAR MANAGEMENT LLC
$874,400Active4 beds 2 baths2,466 sq. ft.651 Lakes Road, Monroe, NY 10950
MLS# 929552Listed by: HOWARD HANNA RAND REALTY
$399,000Pending3 beds 4 baths1,698 sq. ft.451 Meri Lane, Monroe, NY 10950
MLS# 932221Listed by: KELLER WILLIAMS VALLEY REALTY
$54,900Active10.14 Acres15 Deer Run, Chester, NY 12817
MLS# 202528852Listed by: PEARSALL REALTY
$749,000Active6 beds 3 baths3,066 sq. ft.3 Grand View Terrace, Chester, NY 10918
MLS# 925401Listed by: EREALTY ADVISORS, INC
$500,000Pending4 beds 3 baths2,098 sq. ft.16 Mari Road, Chester, NY 10918
MLS# 926859Listed by: KELLER WILLIAMS REALTY
$369,000Pending3 beds 3 baths1,331 sq. ft.2915 Whispering Hills, Chester, NY 10918
MLS# 927990Listed by: CENTURY 21 FULL SERVICE REALTY
$740,000Active4 beds 4 baths2,780 sq. ft.7 Park Place, Chester, NY 10918
MLS# 927218Listed by: CENTURY 21 FULL SERVICE REALTY
$650,000Pending5 beds 4 baths2,550 sq. ft.3 Derose Lane, Chester, NY 10918
MLS# 924694Listed by: HOWARD HANNA RAND REALTY
$425,000Active3 beds 1 baths1,266 sq. ft.84 Pine Hill Road, Chester, NY 10918
MLS# 926175Listed by: EREALTY ADVISORS, INC
$525,000Pending4 beds 2 baths1,928 sq. ft.219 Bull Mill Road, Chester, NY 10918
MLS# 924125Listed by: KELLER WILLIAMS REALTY
$1,750,000Active6 beds 8 baths7,034 sq. ft.69 Cedar Pond Lane, Chester, NY 10918
MLS# 920071Listed by: FOUR SEASONS SOTHEBYS INTL
$475,000Active4 beds 3 baths1,357 sq. ft.70 Main Street, Chester, NY 10918
MLS# 914556Listed by: KELLER WILLIAMS HUDSON VALLEY
$430,000Active3 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
$359,900Pending3 beds 2 baths1,376 sq. ft.264 Heritage Lane, Monroe, NY 10950
MLS# 899973Listed by: HOWARD HANNA RAND REALTY- New
$699,990Active4 beds 3 baths1,867 sq. ft.34 Mountainside Drive, Chester, NY 10918
MLS# 956879Listed by: OUR HOUSE REAL ESTATE GROUP 
$509,999Active3 beds 2 baths1,800 sq. ft.391 Bull Mill Road, Chester, NY 10918
MLS# 880804Listed by: CENTURY 21 REALTY CENTER
$515,000Pending4 beds 3 baths2,898 sq. ft.25 High Street, Chester, NY 10918
MLS# 883804Listed by: CHRISTIE'S INT. REAL ESTATE
$1,100,000Active4 beds 4 baths4,467 sq. ft.53 Odyssey Drive, Chester, NY 10918
MLS# 881474Listed by: HOWARD HANNA RAND REALTY
$1,498,888Active4 beds 4 baths7,308 sq. ft.37-39 Main Street, Chester, NY 10918
MLS# 873541Listed by: EXP 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
$500,000Active0.83 AcresMain Street, Chester, NY 10918
MLS# H6204360Listed by: KELLER WILLIAMS REALTY
Local realty services provided by:CENTURY 21 Alliance Realty Group, CENTURY 21 Awaye Realty, CENTURY 21 North East
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.