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Chester town, NY - homes for sale
93 of 93 results displayed
- Coming SoonOpen Sat, 12 to 2pm
$475,000Coming Soon3 beds 2 baths1,848 sq. ft.3 Mari Road, Sugar Loaf, NY 10918
MLS# 1068654Listed by: DIVINE REALTY NY, LLC - Coming Soon
$299,999Coming Soon3 beds 1 baths1,046 sq. ft.14 School Street, Chester, NY 10918
MLS# 1069090Listed by: HOWARD HANNA RAND REALTY - New
$360,000Active3 beds 1 baths1,561 sq. ft.33 Meadow Avenue, Chester, NY 10918
MLS# 1068790Listed by: RIVER REALTY SERVICES, INC. - New
$939,000Active4 beds 3 baths3,406 sq. ft.82 Goosepond Mountain Road, Chester, NY 10918
MLS# 1034493Listed by: MK REALTY INC - New
$365,000Active5.1 Acres90 Odyssey Drive, Chester, NY 10918
MLS# 1067328Listed by: RE/MAX TOWN & COUNTRY - New
$499,000Active3 beds 2 baths2,000 sq. ft.7 Townsend Place, Chester, NY 10918
MLS# 1045305Listed by: NATIONAL VETERANS REALTY GROUP - New
$1,599,999Active6 beds 8 baths7,034 sq. ft.69 Cedar Pond Lane, Chester, NY 10918
MLS# 1066175Listed by: PROMINENT PROPERTIES SOTHEBY'S 
$975,000Active5 beds 4 baths5,312 sq. ft.53 Gibson Hill Road, Chester, NY 10918
MLS# 1065336Listed by: EXP REALTY
$880,000Active5 beds 3 baths3,600 sq. ft.2 Periwinkle Court, Chester, NY 10918
MLS# 1062146Listed by: MK REALTY INC- Open Sun, 12 to 2pm
$719,000Active4 beds 3 baths3,763 sq. ft.28 Pewter Circle, Chester, NY 10918
MLS# 1056857Listed by: CENTURY 21 FULL SERVICE REALTY 
$239,900Active2 beds 1 baths1,084 sq. ft.2313 Whispering Hills, Chester, NY 10918
MLS# 1061960Listed by: R2M REALTY INC
$595,000Active3 beds 2 baths1,842 sq. ft.161 Highland Avenue, Monroe, NY 10950
MLS# 1059180Listed by: EXP REALTY
$849,900Active4 beds 3 baths3,200 sq. ft.Lot 3 - 62 Camp Monroe Road, Monroe, NY 10950
MLS# 1053820Listed by: HOWARD HANNA RAND REALTY
$599,000Pending4 beds 5 baths3,326 sq. ft.111 Ayr Road, Chester, NY 10918
MLS# 1049653Listed by: CURASI REALTY, INC.
$524,999Active4 beds 2 baths1,894 sq. ft.50 Lincoln Road, Monroe, NY 10950
MLS# 1056405Listed by: WEICHERT REALTORS
$339,900Active2 beds 2 baths1,086 sq. ft.3706 Whispering Hills, Chester, NY 10918
MLS# 1039289Listed by: EXP REALTY
$299,000Active2 beds 2 baths1,086 sq. ft.2107 Whispering Hills, Chester, NY 10918
MLS# 1050213Listed by: WANSOR REALTY
$485,000Active3 beds 3 baths2,441 sq. ft.94 Booth Road, Chester, NY 10918
MLS# 1050173Listed by: HOWARD HANNA RAND REALTY
$599,000Active4 beds 3 baths2,082 sq. ft.123 Pickerel Road, Monroe, NY 10950
MLS# 1052929Listed by: CENTURY 21 REALTY CENTER
$549,000Active4 beds 2 baths2,824 sq. ft.147 Main Street, Chester, NY 10918
MLS# 1052484Listed by: HOWARD HANNA RAND REALTY
$269,000Active2 beds 1 baths1,084 sq. ft.1212 Whispering Hills, Chester, NY 10918
MLS# 1048656Listed by: KELLER WILLIAMS REALTY
$515,000Active4 beds 3 baths2,216 sq. ft.16 Cambridge Circle, Monroe, NY 10950
MLS# 1041577Listed by: KW HUDSON VALLEY UNITED
$499,999Active2 beds 2 baths1,910 sq. ft.19 Meadow Avenue, Chester, NY 10918
MLS# 1050131Listed by: RE/MAX TOWN & COUNTRY
$499,000Pending3 beds 3 baths1,848 sq. ft.264 Bull Mill Road, Chester, NY 10918
MLS# 1049026Listed by: KELLER WILLIAMS REALTY
$879,000Pending3 beds 4 baths3,764 sq. ft.101 Beverly Road, Chester, NY 10918
MLS# 1048079Listed by: GREENE REALTY GROUP
$449,000Active4 beds 2 baths1,832 sq. ft.8 Townsend Place, Chester, NY 10918
MLS# 1047996Listed by: HOWARD HANNA RAND REALTY- Open Sat, 10:30am to 1:30pm
$376,000Active3 beds 1 baths1,288 sq. ft.21 Midway Drive, Monroe, NY 10950
MLS# 1044454Listed by: HOWARD HANNA RAND REALTY - Open Sun, 2:30 to 4:30pm
$679,000Active4 beds 4 baths2,960 sq. ft.5 Red Fox Run, Chester, NY 10918
MLS# 1046418Listed by: HOWARD HANNA RAND REALTY 
$370,000Active3 beds 3 baths1,331 sq. ft.4704 Whispering Hills, Chester, NY 10918
MLS# 1038636Listed by: SAHAGIAN REALTY LLC
$374,900Pending3 beds 2 baths1,644 sq. ft.260 Gibson Hill Road, Chester, NY 10918
MLS# 1044316Listed by: KELLER WILLIAMS REALTY
$354,900Active3 beds 3 baths1,331 sq. ft.2921 Whispering Hills, Chester, NY 10918
MLS# 1043986Listed by: ARC REALTY 1 IN SALES
$290,000Active2 beds 2 baths1,053 sq. ft.1005 Whispering Hills, Chester, NY 10918
MLS# 1043197Listed by: CENTURY 21 FULL SERVICE REALTY
$739,000Active4 beds 3 baths2,599 sq. ft.121 Conklingtown Road, Chester, NY 10918
MLS# 1042913Listed by: MS REALTY GROUP USA, INC
$550,000Pending3 beds 2 baths1,583 sq. ft.50 Hambletonian Avenue, Chester, NY 10918
MLS# 1042882Listed by: HOWARD HANNA RAND REALTY
$289,000Active2 beds 1 baths1,084 sq. ft.2124 Whispering Hills, Chester, NY 10918
MLS# 1042658Listed by: HOWARD HANNA RAND REALTY
$599,999Active3 beds 3 baths2,902 sq. ft.3561 Rte 94, Chester, NY 10918
MLS# 1041906Listed by: HOWARD HANNA RAND REALTY- Open Sat, 12:30 to 2:30pm
$750,000Active4 beds 3 baths2,280 sq. ft.1 Sanford Avenue, Chester, NY 10918
MLS# 1041533Listed by: REDFIN REAL ESTATE 
$360,000Pending3 beds 3 baths1,331 sq. ft.3409 Whispering Hills, Chester, NY 10918
MLS# 1032618Listed by: HOWARD HANNA RAND REALTY
$839,000Pending4 beds 4 baths2,707 sq. ft.34 Boville Court, Chester, NY 10918
MLS# 1040485Listed by: KELLER WILLIAMS VALLEY REALTY
$690,000Active4 beds 3 baths3,296 sq. ft.13 Bianca Boulevard, Chester, NY 10918
MLS# 1040084Listed by: KELLER WILLIAMS REALTY
$675,000Pending3 beds 3 baths3,202 sq. ft.188 Creamery Pond Road, Chester, NY 10918
MLS# 1038759Listed by: KELLER WILLIAMS REALTY
$440,000Active3 beds 2 baths1,728 sq. ft.1367 Kings Highway, Chester, NY 10918
MLS# 1036770Listed by: GREENE REALTY GROUP
$739,900Active4 beds 4 baths3,080 sq. ft.20 Mountainside Drive, Chester, NY 10918
MLS# 1037562Listed by: EXP REALTY
$250,000Pending3 beds 3 baths1,320 sq. ft.607 Mountain Laurel Drive, Monroe, NY 10950
MLS# 1037650Listed by: WEICHERT REALTORS
$490,000Active3 beds 2 baths1,676 sq. ft.74 Heaton Road, Monroe, NY 10950
MLS# 1037241Listed by: COLDWELL BANKER REALTY
$495,000Pending4 beds 2 baths1,820 sq. ft.8 Bridle Lane, Chester, NY 10918
MLS# 1036394Listed by: KELLER WILLIAMS REALTY
$289,000Pending2 beds 1 baths1,004 sq. ft.166 Bull Mill Road, Chester, NY 10918
MLS# 1030923Listed by: KELLER WILLIAMS VALLEY REALTY
$475,000Pending3 beds 2 baths1,624 sq. ft.21 Trotting Drive, Chester, NY 10918
MLS# 1030740Listed by: KELLER WILLIAMS REALTY
$385,000Active3 beds 3 baths1,694 sq. ft.213 Eagleton Drive, Monroe, NY 10950
MLS# 1030733Listed by: KELLER WILLIAMS VALLEY REALTY
$419,000Active3 beds 3 baths1,357 sq. ft.70 Main Street, Chester, NY 10918
MLS# 1034449Listed by: CURASI REALTY, INC.
$355,000Active3 beds 3 baths1,331 sq. ft.2522 Whispering Hills, Chester, NY 10918
MLS# 1027103Listed by: HOWARD HANNA RAND REALTY
$399,999Active3 beds 2 baths1,500 sq. ft.66 Whitetail Run, Chester, NY 10918
MLS# 1033721Listed by: HOWARD HANNA RAND REALTY
$425,000Pending3 beds 2 baths2,460 sq. ft.23 Pike Court, Monroe, NY 10950
MLS# 1031523Listed by: RE/MAX BENCHMARK REALTY GROUP
$750,000Active5 beds 3 baths2,700 sq. ft.3 Hilltop Lane, Chester, NY 10918
MLS# 1031147Listed by: MK REALTY INC
$299,000Active4 beds 1 baths1,504 sq. ft.151 Main Street, Chester, NY 10918
MLS# 1031155Listed by: HUDSON VALLEY GRIFFITH
$760,000Active5 beds 3 baths2,700 sq. ft.1 Hilltop Lane, Chester, NY 10918
MLS# 1031045Listed by: MK REALTY INC
$575,000Active6 beds 2 baths68 Conklingtown Road #1&2, Chester, NY 10918
MLS# 992189Listed by: MS REALTY GROUP USA, INC
$360,000Active3 beds 3 baths1,585 sq. ft.154 Eagleton Drive, Monroe, NY 10950
MLS# 1026625Listed by: KELLER WILLIAMS REALTY
$299,999Pending3 beds 3 baths1,840 sq. ft.402 Mountain Laurel Drive, Monroe, NY 10950
MLS# 1025157Listed by: KELLER WILLIAMS REALTY
$750,000Pending5 beds 3 baths2,700 sq. ft.2 Hemlock Court, Chester, NY 10918
MLS# 1025992Listed by: MK REALTY INC
$349,999Active4 beds 2 baths1,560 sq. ft.241 Meadow Avenue, Chester, NY 10918
MLS# 1024779Listed by: KELLER WILLIAMS REALTY
$725,000Pending3 beds 3 baths2,677 sq. ft.1 Arborvitae Court, Chester, NY 10918
MLS# 1024518Listed by: MK REALTY INC
$750,000Pending5 beds 3 baths2,700 sq. ft.3 Hemlock Court, Chester, NY 10918
MLS# 1020128Listed by: MK REALTY INC
$349,999Pending3 beds 2 baths1,316 sq. ft.3414 Whispering Hills, Chester, NY 10918
MLS# 974398Listed by: KW HUDSON VALLEY UNITED- Open Sun, 12 to 2pm
$499,999Active3 beds 3 baths1,908 sq. ft.11 Chandler Drive, Chester, NY 10918
MLS# 1018371Listed by: COLDWELL BANKER REALTY 
$549,000Pending3 beds 3 baths2,374 sq. ft.44 Wilson Road, Monroe, NY 10950
MLS# 1016146Listed by: KELLER WILLIAMS REALTY
$850,000Pending5 beds 3 baths3,200 sq. ft.5 Hilltop Lane, Chester, NY 10918
MLS# 1020076Listed by: MK REALTY INC
$634,999Active4 beds 3 baths2,316 sq. ft.424 Laroe Road, Chester, NY 10918
MLS# 1013375Listed by: EPIQUE REALTY- Open Sat, 12 to 3pm
$789,900Active5 beds 4 baths4,697 sq. ft.19 Grand View Terrace, Chester, NY 10918
MLS# 1012919Listed by: EXP REALTY 
$900,000Active4 beds 2 baths2,466 sq. ft.651 Lakes Road, Monroe, NY 10950
MLS# 997767Listed by: HOWARD HANNA RAND REALTY
$875,000Active4 beds 3 baths3,656 sq. ft.49 Stone Mountain Trail, Chester, NY 10918
MLS# 1011165Listed by: EREALTY ADVISORS, INC
$1,200,000Active4 beds 3 baths2,711 sq. ft.63 Whitetail Run, Chester, NY 10918
MLS# 1010784Listed by: SPIRAL NY REAL ESTATE LLC
$910,000Active4 beds 3 baths3,955 sq. ft.1 Oakland Avenue, Chester, NY 10918
MLS# 1006113Listed by: HOWARD HANNA RAND REALTY
$549,900Pending3 beds 2 baths2,138 sq. ft.3318 State Route 94, Chester, NY 10918
MLS# 1008703Listed by: HOWARD HANNA RAND REALTY
$675,000Pending4 beds 3 baths2,784 sq. ft.335 Laroe Road, Chester, NY 10918
MLS# 1009848Listed by: COLDWELL BANKER CHOICE PROP.
$419,000Active3 beds 2 baths1,460 sq. ft.4 Maple Lane, Monroe, NY 10950
MLS# 1008564Listed by: FLAG REALTY GROUP
$999,900Pending-- beds -- baths4,032 sq. ft.206 Greycourt Road, Chester, NY 10918
MLS# 1003998Listed by: CRONIN & COMPANY REAL ESTATE
$250,000Active2 beds 1 baths1,062 sq. ft.804 Swan Hollow Road, Monroe, NY 10950
MLS# 1006554Listed by: KELLER WILLIAMS REALTY
$525,000Active4 beds 3 baths2,698 sq. ft.24 Walnut Street, Chester, NY 10918
MLS# 1004369Listed by: KELLER WILLIAMS VILLAGE SQ RLT
$349,000Active46 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
$825,000Pending4 beds 3 baths2,732 sq. ft.45 Whitetail Run, Chester, NY 10918
MLS# 999741Listed by: HUDSON VALLEY HOME CONNECTION
$744,999Active4 beds 3 baths2,718 sq. ft.58 Nancy Lane, Chester, NY 10918
MLS# 995624Listed by: HOWARD HANNA RAND REALTY
$1,145,000Active9 beds 7 baths4,965 sq. ft.19 High Street, Chester, NY 10918
MLS# 995148Listed by: KELLER WILLIAMS REALTY
$759,900Active4 beds 3 baths2,250 sq. ft.90 Pewter Circle, Chester, NY 10918
MLS# 981270Listed by: KELLER WILLIAMS REALTY
$869,900Pending4 beds 3 baths3,000 sq. ft.10 Wells Sweep Lane, Chester, NY 10918
MLS# 966048Listed by: KELLER WILLIAMS 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
$379,900Pending2 beds 1 baths1,026 sq. ft.7 Hambletonian Avenue, Chester, NY 10918
MLS# 964090Listed by: HOMESMART HOMES & ESTATES
$699,995Active6 beds 4 baths4,204 sq. ft.487 Black Meadow Road, Chester, NY 10918
MLS# 960665Listed by: JOSEPH BARATTA COMPANY REALTY
$549,000Pending4 beds 3 baths2,112 sq. ft.150 Lake Region Boulevard, Monroe, NY 10950
MLS# 955186Listed by: HUDSON VALLEY HOME CONNECTION
$275,000Active2 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
Local realty services provided by:Better Homes and Gardens Real Estate Realty Connect
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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.