View 5 Bens Way Chester, NY MLS# 959390
    1 of 26
    OPEN HOUSE: Saturday 5/2 1:00 PM - 3:00 PM
    $699,999
    4

    Beds

    2.1

    Baths

    2,544

    Sq.Ft.

    5 Bens Way

    Chester, NY

    Courtesy of KELLER WILLIAMS HUDSON VALLEY
    View 34 Mountainside Drive Chester, NY MLS# 956879
    $699,990
    4

    Beds

    3.0

    Baths

    1,867

    Sq.Ft.

    34 Mountainside Drive

    Chester, NY

    Courtesy of OUR HOUSE REAL ESTATE GROUP
    View 34 Booth Road Chester, NY MLS# 961100
    • Virtual Tour
    1 of 42
    $699,000
    4

    Beds

    2.1

    Baths

    2,506

    Sq.Ft.

    34 Booth Road

    Chester, NY

    Courtesy of CENTURY 21 FULL SERVICE REALTY
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 360 Prospect Road Chester, NY MLS# 944607
    $689,000
    3

    Beds

    3.0

    Baths

    3,000

    Sq.Ft.

    360 Prospect Road

    Chester, NY

    Courtesy of EREALTY ADVISORS, INC
    View 50 Elkay Drive Chester, NY MLS# 954329
    $650,000
    Studio

    Beds

    0.0

    Baths

    87,120

    Sq.Ft.

    50 Elkay Drive

    Chester, NY

    Courtesy of POINT REALTY USA
    View 101 Oxford Road Chester, NY MLS# 943068
    $639,000
    3

    Beds

    1.1

    Baths

    1,816

    Sq.Ft.

    101 Oxford Road

    Chester, NY

    Courtesy of LOOP REALTY INC
    View 25 Sugarloaf Mountain Road Chester, NY MLS# 951920
    $635,000
    3

    Beds

    2.1

    Baths

    1,954

    Sq.Ft.

    25 Sugarloaf Mountain Road

    Chester, NY

    Courtesy of CRONIN & COMPANY REAL ESTATE
    View 35 Maple Avenue Chester, NY MLS# 990509
    • Recently Listed
    1 of 28
    $549,900
    3

    Beds

    3.0

    Baths

    2,032

    Sq.Ft.

    35 Maple Avenue

    Chester, NY

    Courtesy of RE/MAX BENCHMARK REALTY GROUP
    View 11 Oxford Depot Chester, NY MLS# 991245
    • Recently Listed
    1 of 27
    $519,000
    3

    Beds

    2.0

    Baths

    1,748

    Sq.Ft.

    11 Oxford Depot

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY
    View Main Street Chester, NY MLS# H6204360
    $500,000
    Studio

    Beds

    0.0

    Baths

    36,098

    Sq.Ft.

    Main Street

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 5 N Hudson Street Chester, NY MLS# 976521
    $500,000
    3

    Beds

    2.0

    Baths

    2,688

    Sq.Ft.

    5 N Hudson Street

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 1367 Kings Highway Chester, NY MLS# 951876
    $460,000
    3

    Beds

    1.1

    Baths

    1,728

    Sq.Ft.

    1367 Kings Highway

    Chester, NY

    Courtesy of KARTEN REAL ESTATE SVCS LLC
    View 5 Roggia Road Chester, NY MLS# 978824
    • Virtual Tour
    1 of 32
    $450,000
    3

    Beds

    2.0

    Baths

    1,882

    Sq.Ft.

    5 Roggia Road

    Chester, NY

    Courtesy of NAZMA REAL ESTATE LLC
    View 31 Hudson Street Chester, NY MLS# 963657
    $449,900
    2

    Beds

    2.0

    Baths

    1,998

    Sq.Ft.

    31 Hudson Street

    Chester, NY

    Courtesy of BHG REAL ESTATE GREEN TEAM
    View 16 Oakland Avenue Chester, NY MLS# 939522
    $425,000
    4

    Beds

    2.1

    Baths

    2,090

    Sq.Ft.

    16 Oakland Avenue

    Chester, NY

    Courtesy of BHG REAL ESTATE GREEN TEAM
    View 7 Hambletonian Avenue Chester, NY MLS# 964090
    $410,000
    2

    Beds

    1.0

    Baths

    1,026

    Sq.Ft.

    7 Hambletonian Avenue

    Chester, NY

    Courtesy of HOMESMART HOMES & ESTATES
    View 4116 Whispering Hills Chester, NY MLS# 975277
    $375,000
    3

    Beds

    2.1

    Baths

    1,355

    Sq.Ft.

    4116 Whispering Hills

    Chester, NY

    Courtesy of WILLIAM RAVEIS-NEW YORK, LLC
    View 3910 Whispering Hills Chester, NY MLS# 946789
    $369,900
    3

    Beds

    2.1

    Baths

    1,331

    Sq.Ft.

    3910 Whispering Hills

    Chester, NY

    Courtesy of EXP REALTY
    View 2203 Whispering Hills Chester, NY MLS# 954443
    $362,900
    3

    Beds

    2.1

    Baths

    1,331

    Sq.Ft.

    2203 Whispering Hills

    Chester, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 2 Virginia Lane Chester, NY MLS# H6215339
    $350,000
    Studio

    Beds

    0.0

    Baths

    235,224

    Sq.Ft.

    2 Virginia Lane

    Chester, NY

    Courtesy of KELLER WILLIAMS REALTY

    About Chester

    Listings in Chester, NY

    74

    Estimated median home price

    $699,495
    Chester NY Homes for Sale & Properties

    Weichert Realtors is one of the nation's leading providers of Chester, New York real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chester, NY.

    Homes for Sale by Price in Chester, NY

    PriceCount
    $0 - 100K0
    $100K - 200K3
    $200K - 300K6
    $300K - 400K13
    $400K - 500K7
    $500K - 600K3
    $600K - 700K7
    $700K - 800K12
    $800K - 900K8
    $900K - 1M4
    $1M - Max11

    Homes for Sale by Type in Chester, NY

    Property TypeCount
    Single Family46
    Townhouse0
    Condo11
    Commercial5
    Rental23
    Lots and Land12
    Condo/Town/CoOp0
    CoOp0
    Multi Family0
    Mobile Home0
    Farms0

    (Data as of 4/30/2026)

    Information deemed reliable but not guaranteed.

    The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS.

    The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use.

    Information Copyright 2021, OneKey® MLS. All Rights Reserved.