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Chester town, NY - homes for sale
84 of 84 results displayed
- New
$720,000Active4 beds 3 baths1,718 sq. ft.26 Bridle Lane, Chester, NY 10918
MLS# 1011224Listed by: OWNER ENTRY.COM - New
$1,200,000Active4 beds 3 baths2,711 sq. ft.63 Whitetail Run, Chester, NY 10918
MLS# 1010784Listed by: SPIRAL NY REAL ESTATE LLC - Coming SoonOpen Sat, 12 to 2pm
$1,000,000Coming Soon4 beds 3 baths1 Oakland Avenue, Chester, NY 10918
MLS# 1006113Listed by: HOWARD HANNA RAND REALTY - New
$549,900Active3 beds 2 baths2,138 sq. ft.3318 State Route 94, Chester, NY 10918
MLS# 1008703Listed by: HOWARD HANNA RAND REALTY - Open Sun, 11am to 1pmNew
$715,000Active4 beds 3 baths2,784 sq. ft.335 Laroe Road, Chester, NY 10918
MLS# 1009848Listed by: COLDWELL BANKER CHOICE PROP. - Open Sun, 2am to 2:45pmNew
$429,000Active3 beds 2 baths1,460 sq. ft.4 Maple Lane, Monroe, NY 10950
MLS# 1008564Listed by: FLAG REALTY GROUP - New
$1,200,000Active-- beds -- baths4,032 sq. ft.206 Greycourt Road, Chester, NY 10918
MLS# 1003998Listed by: CRONIN & COMPANY REAL ESTATE - New
$385,000Active2 beds 3 baths1,490 sq. ft.152 Eagleton Drive, Monroe, NY 10950
MLS# 998360Listed by: KELLER WILLIAMS REALTY - New
$275,000Active2 beds 1 baths1,062 sq. ft.804 Swan Hollow Road, Monroe, NY 10950
MLS# 1006554Listed by: KELLER WILLIAMS REALTY 
$1,090,000Active4 beds 4 baths4,130 sq. ft.102 Beverly Road, Chester, NY 10918
MLS# 1005710Listed by: KELLER WILLIAMS REALTY
$549,000Active3 beds 3 baths1,730 sq. ft.107 Pine Hill Road, Chester, NY 10918
MLS# 1003546Listed by: HUDSON VALLEY GRIFFITH
$985,000Active5 beds 4 baths3,764 sq. ft.86 Long Vista Lane, Chester, NY 10918
MLS# 1003760Listed by: RE/MAX TOWN & COUNTRY
$579,999Active4 beds 3 baths2,698 sq. ft.24 Walnut Street, Chester, NY 10918
MLS# 1004369Listed by: KELLER WILLIAMS VILLAGE SQ RLT- Open Thu, 12 to 2pm
$779,000Active4 beds 4 baths2,948 sq. ft.270 Bull Mill Road, Chester, NY 10918
MLS# 1000373Listed by: KELLER WILLIAMS REALTY 
$419,000Active3 beds 3 baths1,694 sq. ft.332 Heritage Lane, Monroe, NY 10950
MLS# 994139Listed by: RE/MAX PRIME PROPERTIES
$550,000Active3 beds 3 baths2,083 sq. ft.94 Booth Road, Chester, NY 10918
MLS# 898870Listed by: COMPASS GREATER NY, LLC
$399,000Active46 Acres492 Black Meadow Road, Chester, NY 10918
MLS# 1002697Listed by: EXP REALTY
$900,000Active4 beds 3 baths2,588 sq. ft.60 Whitetail Run, Chester, NY 10918
MLS# 1002536Listed by: REALTY BLUE CORP
$495,000Active4 beds 3 baths1,792 sq. ft.18 Southside Drive, Monroe, NY 10950
MLS# 1001395Listed by: KELLER WILLIAMS REALTY
$849,900Active4 beds 3 baths3,200 sq. ft.Lot 3 - 62 Camp Monroe Road, Monroe, NY 10950
MLS# 934733Listed by: HOWARD HANNA RAND REALTY
$370,000Active3 beds 3 baths1,331 sq. ft.3815 Whispering Hills Drive, Chester, NY 10918
MLS# 1000359Listed by: MK REALTY INC
$825,000Active4 beds 3 baths2,732 sq. ft.45 Whitetail Run, Chester, NY 10918
MLS# 999741Listed by: HUDSON VALLEY HOME CONNECTION- Open Sun, 1:15 to 2pm
$785,000Active5 beds 6 baths5,403 sq. ft.4 Debbie Court, Chester, NY 10918
MLS# 995223Listed by: FLAG REALTY GROUP 
$769,000Active3 beds 3 baths2,718 sq. ft.58 Nancy Lane, Chester, NY 10918
MLS# 995624Listed by: HOWARD HANNA RAND REALTY
$430,000Active3 beds 2 baths1,177 sq. ft.151 Laroe Road, Chester, NY 10918
MLS# 995916Listed by: KELLER WILLIAMS REALTY
$424,999Active3 beds 3 baths1,331 sq. ft.2722 Whispering Hills, Chester, NY 10918
MLS# 994269Listed by: ARTISAN REALTY
$1,195,000Active9 beds 7 baths4,965 sq. ft.19 High Street, Chester, NY 10918
MLS# 995148Listed by: KELLER WILLIAMS REALTY
$319,900Active2 beds 2 baths1,072 sq. ft.2820 Whispering Hills, Chester, NY 10918
MLS# 986005Listed by: R2M REALTY INC.
$450,000Pending4 beds 2 baths1,642 sq. ft.82 Southside Drive, Monroe, NY 10950
MLS# 991081Listed by: EXP REALTY
$499,900Active3 beds 3 baths2,032 sq. ft.35 Maple Avenue, Chester, NY 10918
MLS# 990509Listed by: RE/MAX BENCHMARK REALTY GROUP
$327,000Pending2 beds 2 baths1,316 sq. ft.2323 Whispering Hills, Chester, NY 10918
MLS# 979690Listed by: CENTURY 21 FULL SERVICE REALTY- Open Sat, 12 to 3pm
$849,900Active3 beds 3 baths2,740 sq. ft.149 Creamery Pond Road, Chester, NY 10918
MLS# 986323Listed by: KELLER WILLIAMS REALTY 
$565,000Pending4 beds 3 baths1,846 sq. ft.52 Wilson Road, Monroe, NY 10950
MLS# 986296Listed by: KELLER WILLIAMS REALTY
$1,299,000Active4 beds 4 baths5,712 sq. ft.16 Sunset Ridge, Monroe, NY 10950
MLS# 979798Listed by: SERHANT LLC
$1,100,000Active5 beds 4 baths5,312 sq. ft.53 Gibson Hill Road, Chester, NY 10918
MLS# 986225Listed by: EXP REALTY
$394,900Pending3 beds 3 baths1,762 sq. ft.195 Eagleton Drive, Monroe, NY 10950
MLS# 984688Listed by: CENTURY 21 REALTY CENTER
$569,000Active4 beds 3 baths2,040 sq. ft.78 Pickerel Road, Monroe, NY 10950
MLS# 847899Listed by: EXP REALTY
$1,399,777Active4 beds 4 baths4,508 sq. ft.145 Kings Highway Bypass, Chester, NY 10918
MLS# 982708Listed by: KELLER WILLIAMS REALTY
$425,000Pending3 beds 2 baths1,108 sq. ft.40 Poplar Drive, Monroe, NY 10950
MLS# 982301Listed by: RE/MAX BENCHMARK REALTY GROUP
$875,000Active3 beds 3 baths2,302 sq. ft.2 Pine Hill Road, Chester, NY 10918
MLS# 974429Listed by: ELLIS SOTHEBY'S INTL REALTY
$589,000Pending3 beds 3 baths1,854 sq. ft.101 Whitetail Run, Chester, NY 10918
MLS# 983196Listed by: CRONIN & COMPANY REAL ESTATE
$1,159,900Active4 beds 5 baths4,624 sq. ft.16 Lori Lane, Chester, NY 10918
MLS# 982679Listed by: EXP REALTY
$548,000Active4 beds 3 baths1,916 sq. ft.22 Cambridge Circle, Monroe, NY 10950
MLS# 979471Listed by: HOWARD HANNA RAND REALTY
$499,900Pending3 beds 3 baths1,888 sq. ft.4 Oak Street, Chester, NY 10918
MLS# 973625Listed by: CRONIN & COMPANY REAL ESTATE
$650,000Active4 beds 3 baths3,636 sq. ft.10 Hidden Drive, Monroe, NY 10950
MLS# 835097Listed by: CENTURY 21 FULL SERVICE REALTY
$759,900Active4 beds 3 baths2,250 sq. ft.90 Pewter Circle, Chester, NY 10918
MLS# 981270Listed by: KELLER WILLIAMS REALTY
$869,900Active4 beds 3 baths3,000 sq. ft.10 Wells Sweep Lane, Chester, NY 10918
MLS# 966048Listed by: KELLER WILLIAMS REALTY- Open Sun, 12 to 2pm
$585,000Active4 beds 2 baths2,056 sq. ft.6 Adams Court, Monroe, NY 10950
MLS# 977377Listed by: KELLER WILLIAMS REALTY 
$549,000Pending3 beds 2 baths1,644 sq. ft.38 Jefferson Drive, Monroe, NY 10950
MLS# 978155Listed by: ARROWHEAD REALTY
$450,000Pending3 beds 2 baths1,882 sq. ft.5 Roggia Road, Chester, NY 10918
MLS# 978824Listed by: NAZMA REAL ESTATE LLC
$329,900Active3 beds 2 baths1,316 sq. ft.1311 Whispering Hills, Chester, NY 10918
MLS# 983111Listed by: KELLER WILLIAMS REALTY
$500,000Active3 beds 2 baths2,688 sq. ft.5 N Hudson Street, Chester, NY 10918
MLS# 976521Listed by: KELLER WILLIAMS REALTY
$735,000Pending4 beds 4 baths3,356 sq. ft.55 Beverly Road, Chester, NY 10918
MLS# 977281Listed by: HOWARD HANNA RAND REALTY
$375,000Pending3 beds 3 baths1,355 sq. ft.4116 Whispering Hills, Chester, NY 10918
MLS# 975277Listed by: WILLIAM RAVEIS-NEW YORK, LLC
$395,000Pending3 beds 3 baths1,694 sq. ft.223 Eagleton Drive, Monroe, NY 10950
MLS# 963575Listed by: KELLER WILLIAMS REALTY
$595,000Active5 beds 3 baths2,983 sq. ft.9 Mount Ridge Court, Monroe, NY 10950
MLS# 951183Listed by: RE/MAX BENCHMARK REALTY GROUP
$362,900Pending3 beds 3 baths1,331 sq. ft.2203 Whispering Hills, Chester, NY 10918
MLS# 954443Listed by: HOWARD HANNA RAND REALTY
$879,900Active4 beds 3 baths3,200 sq. ft.1414 Kings Highway, Chester, NY 10918
MLS# 965992Listed by: KELLER WILLIAMS REALTY
$299,000Active5.7 Acres552 Pine Hill Road, Chester, NY 10918
MLS# 958740Listed by: EREALTY ADVISORS, INC
$599,000Active4 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
$399,900Active2 beds 1 baths1,026 sq. ft.7 Hambletonian Avenue, Chester, NY 10918
MLS# 964090Listed by: HOMESMART HOMES & ESTATES
$725,000Active6 beds 4 baths4,204 sq. ft.487 Black Meadow Road, Chester, NY 10918
MLS# 960665Listed by: JOSEPH BARATTA COMPANY REALTY
$319,900Active3 beds 3 baths1,320 sq. ft.607 Mountain Laurel Drive, Monroe, NY 10950
MLS# 961136Listed by: WEICHERT REALTORS
$635,000Pending3 beds 3 baths1,954 sq. ft.25 Sugarloaf Mountain Road, Chester, NY 10918
MLS# 951920Listed by: CRONIN & COMPANY REAL ESTATE
$569,000Active4 beds 3 baths2,112 sq. ft.150 Lake Region Boulevard, Monroe, NY 10950
MLS# 955186Listed by: HUDSON VALLEY HOME CONNECTION
$625,000Active2 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
$275,000Pending2 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
$369,900Pending3 beds 3 baths1,331 sq. ft.3910 Whispering Hills, Chester, NY 10918
MLS# 946789Listed by: EXP REALTY
$215,000Active2 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
$260,000Active2 beds 1 baths1,084 sq. ft.1401 Whispering Hills, Chester, NY 10918
MLS# 935471Listed by: HOWARD HANNA RAND REALTY
$730,000Pending4 beds 4 baths2,780 sq. ft.7 Park Place, Chester, NY 10918
MLS# 927218Listed by: CENTURY 21 FULL SERVICE REALTY
$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
$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 Dream Properties
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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.