Chester town, NY - single-family homes for sale

42 of 42 results displayed

New
$549,900Active
3 beds 3 baths2,032 sq. ft.
35 Maple Avenue, Chester, NY 10918
MLS# 990509Listed by: RE/MAX BENCHMARK REALTY GROUP
New
$887,500Active
3 beds 3 baths2,740 sq. ft.
149 Creamery Pond Road, Chester, NY 10918
MLS# 986323Listed by: KELLER WILLIAMS REALTY
New
$565,000Active
4 beds 3 baths1,846 sq. ft.
52 Wilson Road, Monroe, NY 10950
MLS# 986296Listed by: KELLER WILLIAMS REALTY
Coming Soon
$1,299,000Coming Soon
4 beds 4 baths
16 Sunset Ridge, Monroe, NY 10950
MLS# 979798Listed by: SERHANT LLC
New
$1,100,000Active
5 beds 4 baths5,312 sq. ft.
53 Gibson Hill Road, Chester, NY 10918
MLS# 986225Listed by: EXP REALTY
$569,000Active
4 beds 3 baths2,040 sq. ft.
78 Pickerel Road, Monroe, NY 10950
MLS# 847899Listed by: EXP REALTY
$1,450,000Active
4 beds 4 baths4,508 sq. ft.
145 Kings Highway Bypass, Chester, NY 10918
MLS# 982708Listed by: KELLER WILLIAMS REALTY
$425,000Active
3 beds 2 baths1,108 sq. ft.
40 Poplar Drive, Monroe, NY 10950
MLS# 982301Listed by: RE/MAX BENCHMARK REALTY GROUP
$875,000Active
3 beds 3 baths2,302 sq. ft.
2 Pine Hill Road, Chester, NY 10918
MLS# 974429Listed by: ELLIS SOTHEBY'S INTL REALTY
$589,000Active
3 beds 3 baths1,854 sq. ft.
101 Whitetail Run, Chester, NY 10918
MLS# 983196Listed by: CRONIN & COMPANY REAL ESTATE
$1,159,900Active
4 beds 5 baths4,624 sq. ft.
16 Lori Lane, Chester, NY 10918
MLS# 982679Listed by: EXP REALTY
$575,000Active
4 beds 3 baths1,916 sq. ft.
22 Cambridge Circle, Monroe, NY 10950
MLS# 979471Listed by: HOWARD HANNA RAND REALTY
$690,000Active
4 beds 3 baths3,636 sq. ft.
10 Hidden Drive, Monroe, NY 10950
MLS# 835097Listed by: CENTURY 21 FULL SERVICE REALTY
$759,900Active
4 beds 3 baths2,250 sq. ft.
90 Pewter Circle, Chester, NY 10918
MLS# 981270Listed by: KELLER WILLIAMS REALTY
$869,900Active
4 beds 3 baths3,000 sq. ft.
10 Wells Sweep Lane, Chester, NY 10918
MLS# 966048Listed by: KELLER WILLIAMS REALTY
$599,000Active
4 beds 2 baths2,056 sq. ft.
6 Adams Court, Monroe, NY 10950
MLS# 977377Listed by: KELLER WILLIAMS REALTY
$549,000Active
3 beds 2 baths1,644 sq. ft.
38 Jefferson Drive, Monroe, NY 10950
MLS# 978155Listed by: ARROWHEAD REALTY
$450,000Active
3 beds 2 baths1,882 sq. ft.
5 Roggia Road, Chester, NY 10918
MLS# 978824Listed by: NAZMA REAL ESTATE LLC
$500,000Active
3 beds 2 baths2,688 sq. ft.
5 N Hudson Street, Chester, NY 10918
MLS# 976521Listed by: KELLER WILLIAMS REALTY
$735,000Active
4 beds 4 baths3,356 sq. ft.
55 Beverly Road, Chester, NY 10918
MLS# 977281Listed by: HOWARD HANNA RAND REALTY
$489,000Pending
4 beds 2 baths1,760 sq. ft.
3 Hickory Lane, Monroe, NY 10950
MLS# 972917Listed by: EREALTY ADVISORS, INC
$635,000Active
5 beds 3 baths2,983 sq. ft.
9 Mount Ridge Court, Monroe, NY 10950
MLS# 951183Listed by: RE/MAX BENCHMARK REALTY GROUP
$350,000Pending
2 beds 1 baths1,272 sq. ft.
307 Gibson Hill Road, Chester, NY 10918
MLS# 968972Listed by: HOWARD HANNA RAND REALTY
$879,900Active
4 beds 3 baths3,200 sq. ft.
1414 Kings Highway, Chester, NY 10918
MLS# 965992Listed by: KELLER WILLIAMS REALTY
$449,900Pending
2 beds 2 baths1,998 sq. ft.
31 Hudson Street, Chester, NY 10918
MLS# 963657Listed by: BHG REAL ESTATE GREEN TEAM
$485,000Active
3 beds 2 baths1,460 sq. ft.
35 Maple Lane, Monroe, NY 10950
MLS# 965197Listed by: EXP REALTY
$799,000Active
4 beds 3 baths3,120 sq. ft.
558 Pine Hill Road, Chester, NY 10918
MLS# 958731Listed by: EREALTY ADVISORS, INC
$410,000Active
2 beds 1 baths1,026 sq. ft.
7 Hambletonian Avenue, Chester, NY 10918
MLS# 964090Listed by: HOMESMART HOMES & ESTATES
$799,000Active
5 beds 6 baths5,403 sq. ft.
4 Debbie Court, Chester, NY 10918
MLS# 962813Listed by: FLAG REALTY GROUP
$699,000Pending
4 beds 3 baths2,506 sq. ft.
34 Booth Road, Chester, NY 10918
MLS# 961100Listed by: CENTURY 21 FULL SERVICE REALTY
$725,000Active
6 beds 4 baths4,204 sq. ft.
487 Black Meadow Road, Chester, NY 10918
MLS# 960665Listed by: JOSEPH BARATTA COMPANY REALTY
$319,900Active
3 beds 3 baths1,320 sq. ft.
607 Mountain Laurel Drive, Monroe, NY 10950
MLS# 961136Listed by: WEICHERT REALTORS
$309,900Pending
2 beds 1 baths792 sq. ft.
111 Lake Region Boulevard, Monroe, NY 10950
MLS# 957716Listed by: KELLER WILLIAMS VALLEY REALTY
$635,000Pending
3 beds 3 baths1,954 sq. ft.
25 Sugarloaf Mountain Road, Chester, NY 10918
MLS# 951920Listed by: CRONIN & COMPANY REAL ESTATE
$580,000Active
4 beds 3 baths2,112 sq. ft.
150 Lake Region Boulevard, Monroe, NY 10950
MLS# 955186Listed by: HUDSON VALLEY HOME CONNECTION
$460,000Active
3 beds 2 baths1,728 sq. ft.
1367 Kings Highway, Chester, NY 10918
MLS# 951876Listed by: KARTEN REAL ESTATE SVCS LLC
$425,000Active
4 beds 3 baths2,090 sq. ft.
16 Oakland Avenue, Chester, NY 10918
MLS# 939522Listed by: BHG REAL ESTATE GREEN TEAM
$730,000Active
4 beds 4 baths2,780 sq. ft.
7 Park Place, Chester, NY 10918
MLS# 927218Listed by: CENTURY 21 FULL SERVICE REALTY
$400,000Active
3 beds 1 baths1,561 sq. ft.
33 Meadow Avenue, Chester, NY 10918
MLS# 907272Listed by: RIVER REALTY SERVICES, INC.
$849,900Active
4 beds 3 baths2,603 sq. ft.
32 Mountainside Drive, Chester, NY 10918
MLS# 901144Listed by: OUR HOUSE REAL ESTATE GROUP
$699,990Active
4 beds 3 baths1,867 sq. ft.
34 Mountainside Drive, Chester, NY 10918
MLS# 956879Listed by: OUR HOUSE REAL ESTATE GROUP
$1,100,000Active
4 beds 4 baths4,467 sq. ft.
53 Odyssey Drive, Chester, NY 10918
MLS# 881474Listed by: HOWARD HANNA RAND REALTY

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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.

Terms of use Accessibility DMCA notice Fraud alert Privacy policy Fair housing Do not sell info NY reasonable accommodation Submit agent or broker complaint

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.