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Chester, NY Homes for Sale | Realty.com
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3 beds
99 listings
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New construction
With a pool

Homes for Sale in Chester, NY

Homes for Sale in Chester, NY

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23 of 99 Listings
Map

Homes for Sale in Chester, NY

23 of 99 Listings

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TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 101 Beverly Road — photoNew31Active

    $879,000

    4 bd · 4 ba · 3,764 sqft

    101 Beverly Road, Chester, NY

    Derek J. Greene · Greene Realty Group

  2. 8 Townsend Place — photoNew44Active

    $459,000

    4 bd · 2 ba · 1,832 sqft

    8 Townsend Place, Chester, NY

    Donna Gennaro · Howard Hanna Rand Realty

  3. 5 Red Fox Run — photo47Active

    $679,000

    4 bd · 4 ba · 2,960 sqft

    5 Red Fox Run, Chester, NY

    Gina Dudgeon · Howard Hanna Rand Realty

  4. 24 Memory Lane — photoPrice Reduced28Active

    $599,000

    2 bd · 1 ba · 752 sqft

    24 Memory Lane, Chester, NY

    Ashley Nagy · Davies Davies & Associates Real Estate LLC

  5. 19 Meadow — photo30Active

    $495,000

    3 bd · 2 ba · 1,910 sqft

    19 Meadow, Chester, NY

    Jennifer-Lynn Colon · Stephen Kaufman Real Estate

  6. 4704 Whispering Hills — photo19Active

    $380,000

    3 bd · 3 ba · 1,331 sqft

    4704 Whispering Hills, Chester, NY

    Evelyn Martino · Sahagian Realty LLC

  7. 3409 Whispering Hills — photo24Active

    $360,000

    3 bd · 3 ba · 1,331 sqft

    3409 Whispering Hills, Chester, NY

    Bernadette Giordano · Howard Hanna Rand Realty

  8. 69 Cedar Pond Lane — photo50Active

    $1,685,000

    6 bd · 8 ba · 7,034 sqft

    69 Cedar Pond Lane, Chester, NY

    Alexander Fayn · Prominent Properties Sotheby's

  9. 330 Stone Bridge Road — photo43Active

    $825,000

    4 bd · 4 ba · 3,054 sqft

    330 Stone Bridge Road, Chester, NY

    Barbara Kearney · Hunt Real Estate ERA

  10. 188 Creamery Pond Road — photo45Active

    $675,000

    3 bd · 3 ba · 3,202 sqft

    188 Creamery Pond Road, Chester, NY

    Patricia A Brady · Keller Williams Realty

  11. 3561 Rte 94 — photo50Active

    $649,999

    3 bd · 3 ba · 2,902 sqft

    3561 Rte 94, Chester, NY

    Gina Dudgeon · Howard Hanna Rand Realty

  12. 260 Gibson Hill Road — photo22Active

    $374,900

    3 bd · 2 ba · 1,644 sqft

    260 Gibson Hill Road, Chester, NY

    Camilia Anka · Keller Williams Realty

  13. 2124 Whispering Hills — photo18Active

    $299,000

    2 bd · 1 ba · 1,084 sqft

    2124 Whispering Hills, Chester, NY

    Beverly Huaman · Howard Hanna Rand Realty

  14. 2921 Whispering Hills — photo42Active

    $374,900

    3 bd · 3 ba · 1,331 sqft

    2921 Whispering Hills, Chester, NY

    Amanda M Dnistrian · ARC Realty 1 in Sales

  15. 1005 Whispering Hills — photo28Active

    $290,000

    2 bd · 2 ba · 1,053 sqft

    1005 Whispering Hills, Chester, NY

    Kristie A. Jacques · Century 21 Full Service Realty

  16. 121 Conklingtown Road — photo50Active

    $749,000

    4 bd · 3 ba · 2,599 sqft

    121 Conklingtown Road, Chester, NY

    Chaim Weiss · MS Realty Group USA, Inc

  17. 50 Hambletonian Avenue — photo45Active

    $550,000

    3 bd · 2 ba · 1,583 sqft

    50 Hambletonian Avenue, Chester, NY

    Jennifer Loprieno · Howard Hanna Rand Realty

  18. 68 Birchwood Drive — photo31Active

    $1,899,000

    4 bd · 3 ba · 1,782 sqft

    68 Birchwood Drive, Chester, NY

    Barbara Kearney · Hunt Real Estate ERA

  19. 13 Bianca Boulevard — photo49Active

    $700,000

    4 bd · 3 ba · 3,296 sqft

    13 Bianca Boulevard, Chester, NY

    Theresa M Powers · Keller Williams Realty

  20. 81 Clarkson Road — photoPrice Reduced32Active

    $395,000

    2 bd · 2 ba · 1,086 sqft

    81 Clarkson Road, Chester, NY

    Barbara Kearney · Hunt Real Estate ERA

  21. 1 Sanford Avenue — photo32Active

    $750,000

    4 bd · 3 ba · 2,280 sqft

    1 Sanford Avenue, Chester, NY

    Danielle R. Hinton · Redfin Real Estate

  22. 65 Oxford Springs Road — photo38Active

    $699,000

    5 bd · 4 ba · 3,463 sqft

    65 Oxford Springs Road, Chester, NY

    Stephanie Dolan · HomeSmart Homes & Estates

  23. 4827 New York 8 — photo41Active

    $380,000

    2 bd · 2 ba · 1,350 sqft

    4827 New York 8, Chester, NY

    Vickie Reed · Hunt ERA

12…5

Explore Chester homes

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The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Listing data & MLS disclosures

Global MLS
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Information is deemed reliable but not guaranteed.
Listing information ©2026 Local REALTOR® - Douglas Perlson, Corp. Broker - (646) 315-9116. All Rights Reserved. Last Updated: 2026-09-08 22:03:48 UTC
OneKey MLS
The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved
    • New construction
    • With a pool

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #10311208632

    Call Thomas

    Chester, NY community profile

    Population
    4,099
    Median income
    $110,682
    Housing units
    1,761
    People per sq. mi.
    120.2
    Area
    34.1 sq. mi.

    Source: HJN community data

    Chester housing market

    July 2026 · This period is still settling

    Chester 12-month median sale price trend

    Homes that sold · County records, as of Jul 30, 2026

    Median sale price
    $452,999$342,000–$676,250 typical range
    Price per sq. ft.
    $277
    Sales
    14
    Paid in cash
    21.4%

    Homes on the market · MLS, as of Jul 21, 2026

    Median list price
    $750,000
    Homes for sale
    64

    Price trend · Assessor repeat sales, as of Jul 31, 2026

    Year-over-year
    20.8%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 15, 2026

    Median home size
    2,098 sq. ft.

    Nearby areas

    ZIP codes

    • 12401 (74)
    • 12477 (42)
    • 12572 (41)
    • 12538 (40)
    • 12569 (30)
    • 12571 (29)
    • 12414 (28)
    • 12601 (26)

    Cities

    • Kingston (71)
    • Poughkeepsie (42)
    • Saugerties (42)
    • Rhinebeck (41)
    • Hyde Park (40)
    • Pleasant Valley (32)
    • Red Hook (30)
    • Catskill (27)