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Chester town, NY - single-family homes for sale
71 of 71 results displayed
- Coming Soon
$599,000Coming Soon4 beds 5 baths3,326 sq. ft.111 Ayr Road, Chester, NY 10918
MLS# 1049653Listed by: CURASI REALTY, INC. - New
$849,900Active4 beds 3 baths3,200 sq. ft.Lot 3 - 62 Camp Monroe Road, Monroe, NY 10950
MLS# 1053820Listed by: HOWARD HANNA RAND REALTY - New
$549,000Active4 beds 2 baths1,894 sq. ft.50 Lincoln Road, Monroe, NY 10950
MLS# 1056405Listed by: WEICHERT REALTORS - New
$525,000Active3 beds 3 baths2,441 sq. ft.94 Booth Road, Chester, NY 10918
MLS# 1050173Listed by: HOWARD HANNA RAND REALTY - New
$599,000Active4 beds 3 baths2,082 sq. ft.123 Pickerel Road, Monroe, NY 10950
MLS# 1052929Listed by: CENTURY 21 REALTY CENTER 
$550,000Active4 beds 3 baths2,216 sq. ft.16 Cambridge Circle, Monroe, NY 10950
MLS# 1041577Listed by: KW HUDSON VALLEY UNITED
$525,000Active2 beds 2 baths1,910 sq. ft.19 Meadow Avenue, Chester, NY 10918
MLS# 1050131Listed by: RE/MAX TOWN & COUNTRY
$879,000Active4 beds 4 baths3,764 sq. ft.101 Beverly Road, Chester, NY 10918
MLS# 1048079Listed by: GREENE REALTY GROUP
$459,000Active4 beds 2 baths1,832 sq. ft.8 Townsend Place, Chester, NY 10918
MLS# 1047996Listed by: HOWARD HANNA RAND REALTY- Open Sat, 10:30am to 2:30pm
$409,000Active3 beds 1 baths1,288 sq. ft.21 Midway Drive, Monroe, NY 10950
MLS# 1044454Listed by: HOWARD HANNA RAND REALTY 
$679,000Active4 beds 4 baths2,960 sq. ft.5 Red Fox Run, Chester, NY 10918
MLS# 1046418Listed by: HOWARD HANNA RAND REALTY- Open Sat, 1 to 3pm
$1,599,999Active6 beds 8 baths69 Cedar Pond Lane, Chester, NY 10918
MLS# 26032766Listed by: PROMINENT PROPERTIES SOTHEBY'S INTERNATIONAL REALTY-ALPINE
$374,900Pending3 beds 2 baths1,644 sq. ft.260 Gibson Hill Road, Chester, NY 10918
MLS# 1044316Listed by: KELLER WILLIAMS REALTY
$749,000Active4 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- Open Sat, 11am to 1pm
$619,999Active3 beds 3 baths2,902 sq. ft.3561 Rte 94, Chester, NY 10918
MLS# 1041906Listed by: HOWARD HANNA RAND REALTY 
$669,000Active3 beds 3 baths2,533 sq. ft.173 Creamery Pond Road, Chester, NY 10918
MLS# 1040801Listed by: KELLER WILLIAMS REALTY
$750,000Active4 beds 3 baths2,280 sq. ft.1 Sanford Avenue, Chester, NY 10918
MLS# 1041533Listed by: REDFIN REAL ESTATE
$475,000Pending4 beds 2 baths1,820 sq. ft.32 Surrey Road, Chester, NY 10918
MLS# 1040785Listed by: EXP REALTY
$839,000Active4 beds 4 baths2,707 sq. ft.34 Boville Court, Chester, NY 10918
MLS# 1040485Listed by: KELLER WILLIAMS VALLEY REALTY
$700,000Active4 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
$749,900Active4 beds 4 baths3,080 sq. ft.20 Mountainside Drive, Chester, NY 10918
MLS# 1037562Listed by: EXP REALTY
$500,000Active3 beds 2 baths1,676 sq. ft.74 Heaton Road, Monroe, NY 10950
MLS# 1037241Listed by: COLDWELL BANKER REALTY- Open Sat, 11am to 1pm
$605,000Active3 beds 2 baths1,848 sq. ft.412 Laroe Road, Chester, NY 10918
MLS# 1035387Listed by: HOWARD HANNA RAND REALTY 
$475,000Pending3 beds 2 baths1,624 sq. ft.21 Trotting Drive, Chester, NY 10918
MLS# 1030740Listed by: KELLER WILLIAMS REALTY
$469,000Active3 beds 3 baths1,357 sq. ft.70 Main Street, Chester, NY 10918
MLS# 1034449Listed by: CURASI REALTY, INC.
$699,900Pending4 beds 3 baths2,715 sq. ft.176 Beverly Road, Chester, NY 10918
MLS# 1034535Listed by: OWNER ENTRY.COM- Open Sat, 12 to 2pm
$435,000Active3 beds 2 baths1,500 sq. ft.66 Whitetail Run, Chester, NY 10918
MLS# 1033721Listed by: HOWARD HANNA RAND REALTY 
$370,000Active3 beds 1 baths1,561 sq. ft.33 Meadow Avenue, Chester, NY 10918
MLS# 1033159Listed by: RIVER REALTY SERVICES, INC.
$425,000Active3 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
$750,000Active5 beds 3 baths2,700 sq. ft.1 Hilltop Lane, Chester, NY 10918
MLS# 1031045Listed by: MK REALTY INC
$549,999Pending4 beds 3 baths2,098 sq. ft.7 Lakeview Drive, Chester, NY 10918
MLS# 1028872Listed by: HOWARD HANNA RAND REALTY
$750,000Active5 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
$750,000Pending5 beds 3 baths2,700 sq. ft.3 Hemlock Court, Chester, NY 10918
MLS# 1020128Listed by: MK REALTY INC
$635,000Pending4 beds 3 baths3,636 sq. ft.10 Hidden Drive, Monroe, NY 10950
MLS# 1023272Listed by: CENTURY 21 FULL SERVICE REALTY- Open Sun, 12:30 to 2:30pm
$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
$850,000Active5 beds 3 baths3,200 sq. ft.5 Hilltop Lane, Chester, NY 10918
MLS# 1020076Listed by: MK REALTY INC
$789,900Active5 beds 4 baths4,697 sq. ft.19 Grand View Terrace, Chester, NY 10918
MLS# 1012919Listed by: EXP REALTY
$1,199,000Active4 beds 4 baths5,712 sq. ft.16 Sunset Ridge, Monroe, NY 10950
MLS# 1015235Listed by: SERHANT LLC
$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
$685,000Pending4 beds 3 baths1,718 sq. ft.26 Bridle Lane, Chester, NY 10918
MLS# 1011224Listed by: OWNER ENTRY.COM
$1,200,000Active4 beds 3 baths2,711 sq. ft.63 Whitetail Run, Chester, NY 10918
MLS# 1010784Listed by: SPIRAL NY REAL ESTATE LLC
$990,000Active4 beds 3 baths3,955 sq. ft.1 Oakland Avenue, Chester, NY 10918
MLS# 1006113Listed by: HOWARD HANNA RAND REALTY
$549,900Active3 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.
$429,000Active3 beds 2 baths1,460 sq. ft.4 Maple Lane, Monroe, NY 10950
MLS# 1008564Listed by: FLAG REALTY GROUP
$525,000Active4 beds 3 baths2,698 sq. ft.24 Walnut Street, Chester, NY 10918
MLS# 1004369Listed by: KELLER WILLIAMS VILLAGE SQ RLT
$900,000Active4 beds 3 baths2,588 sq. ft.60 Whitetail Run, Chester, NY 10918
MLS# 1002536Listed by: REALTY BLUE CORP
$495,000Pending4 beds 3 baths1,792 sq. ft.18 Southside Drive, Monroe, NY 10950
MLS# 1001395Listed by: KELLER WILLIAMS REALTY
$825,000Pending4 beds 3 baths2,732 sq. ft.45 Whitetail Run, Chester, NY 10918
MLS# 999741Listed by: HUDSON VALLEY HOME CONNECTION
$785,000Pending5 beds 6 baths5,403 sq. ft.4 Debbie Court, Chester, NY 10918
MLS# 995223Listed by: FLAG REALTY GROUP- Open Sun, 12 to 2pm
$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
$775,000Pending3 beds 3 baths2,740 sq. ft.149 Creamery Pond Road, Chester, NY 10918
MLS# 986323Listed by: KELLER WILLIAMS REALTY
$1,100,000Pending5 beds 4 baths5,312 sq. ft.53 Gibson Hill Road, Chester, NY 10918
MLS# 986225Listed by: EXP REALTY
$569,000Pending4 beds 3 baths2,040 sq. ft.78 Pickerel Road, Monroe, NY 10950
MLS# 847899Listed by: EXP REALTY
$495,000Pending4 beds 3 baths1,916 sq. ft.22 Cambridge Circle, Monroe, NY 10950
MLS# 979471Listed by: HOWARD HANNA RAND 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
$585,000Pending4 beds 2 baths2,056 sq. ft.6 Adams Court, Monroe, NY 10950
MLS# 977377Listed by: KELLER WILLIAMS REALTY
$879,900Active4 beds 3 baths3,200 sq. ft.1414 Kings Highway, Chester, NY 10918
MLS# 965992Listed by: KELLER WILLIAMS REALTY
$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
Local realty services provided by:CENTURY 21 Monticello Realty, CENTURY 21 Concept 100
The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the NJMLS. Real estate listings held by brokerage firms other than CENTURY 21 Concept 100 are marked with the Internet Data Exchange logo and information about them includes the name of the listing brokers. Some properties listed with the participating brokers do not appear on this website at the request of the seller. Listings of brokers that do not participate in Internet Data Exchange do not appear on this website.
All information deemed reliable but not guaranteed. Last date updated: October 2, 2026. Source: New Jersey Multiple Listing Service, Inc.
2026 New Jersey Multiple Listing Service, Inc. All rights reserved. NJ_MLS Member Broker: Eileen O'Driscoll
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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.