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Chester, NY Homes for Sale | Realty.com
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Start here

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3 beds
106 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 106 Listings
Map

Homes for Sale in Chester, NY

23 of 106 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 3409 Whispering Hills — photo24Active

    $360,000

    3 bd · 3 ba · 1,331 sqft

    3409 Whispering Hills, Chester, NY

    Bernadette Giordano · Howard Hanna Rand Realty

  2. 4704 Whispering Hills — photo19Active

    $380,000

    3 bd · 3 ba · 1,331 sqft

    4704 Whispering Hills, Chester, NY

    Evelyn Martino · Sahagian Realty LLC

  3. 69 Cedar Pond Lane — photo50Active

    $1,685,000

    6 bd · 8 ba · — sqft

    69 Cedar Pond Lane, Chester, NY

    Alexander Fayn · Prominent Properties Sotheby's International Realty-Alpine

  4. 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

  5. 3561 Rte 94 — photo50Active

    $649,999

    3 bd · 3 ba · 2,902 sqft

    3561 Rte 94, Chester, NY

    Gina Dudgeon · Howard Hanna Rand Realty

  6. 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

  7. 2124 Whispering Hills — photo18Active

    $299,000

    2 bd · 1 ba · 1,084 sqft

    2124 Whispering Hills, Chester, NY

    Beverly Huaman · Howard Hanna Rand Realty

  8. 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

  9. 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

  10. 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

  11. 50 Hambletonian Avenue — photo45Active

    $550,000

    3 bd · 2 ba · 1,583 sqft

    50 Hambletonian Avenue, Chester, NY

    Jennifer Loprieno · Howard Hanna Rand Realty

  12. 68 Birchwood Drive — photo30Active

    $1,899,000

    4 bd · 3 ba · 1,782 sqft

    68 Birchwood Drive, Chester, NY

    Barbara Kearney · Hunt Real Estate ERA

  13. 75 White Schoolhouse Road — photo27Active

    $285,000

    3 bd · 2 ba · 1,008 sqft

    75 White Schoolhouse Road, Chester, NY

    Jill Brady · Hunt Real Estate ERA

  14. 13 Bianca Boulevard — photo49Active

    $700,000

    4 bd · 3 ba · 3,296 sqft

    13 Bianca Boulevard, Chester, NY

    Theresa M Powers · Keller Williams Realty

  15. 1 Sanford Avenue — photo30Active

    $750,000

    4 bd · 3 ba · 2,280 sqft

    1 Sanford Avenue, Chester, NY

    Danielle R. Hinton · Redfin Real Estate

  16. 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

  17. 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

  18. 4827 New York 8 — photo41Active

    $380,000

    2 bd · 2 ba · 1,350 sqft

    4827 New York 8, Chester, NY

    Vickie Reed · Hunt ERA

  19. 173 Creamery Pond Road — photo48Active

    $699,000

    3 bd · 3 ba · 2,533 sqft

    173 Creamery Pond Road, Chester, NY

    Michele Tobin · Keller Williams Realty

  20. 63 Hubshop Road — photo19Active

    $459,000

    4 bd · 3 ba · 2,060 sqft

    63 Hubshop Road, Chester, NY

    Ryan Barrett · Keller Williams Realty

  21. 32 Surrey Road — photoPrice Reduced39Active

    $475,000

    4 bd · 2 ba · 1,820 sqft

    32 Surrey Road, Chester, NY

    Ammar Iqbal · eXp Realty

  22. 34 Boville Court — photo46Active

    $839,000

    4 bd · 4 ba · 2,707 sqft

    34 Boville Court, Chester, NY

    Jillian Laga · Keller Williams Valley Realty

  23. 36 Ferris Road — photoPrice Reduced52Active

    $365,500

    3 bd · 2 ba · 1,296 sqft

    36 Ferris Road, Chester, NY

    Jenna Frasier · Selling ADK

12…5

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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: 2026-08-31 14:38:17 UTC
New Jersey MLS
The data relating to the real estate for sale on this website comes in part from the Internet Data Exchange Program of the NJMLS. Real estate listings held by brokerage firms other than Realty.com 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. Copyright © 2026 New Jersey Multiple Listing Service, Inc. All Rights Reserved.
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

    Nearby areas

    ZIP codes

    • 12122 (50)
    • 12477 (37)
    • 12534 (31)
    • 12571 (29)
    • 12076 (28)
    • 12414 (25)
    • 12442 (25)
    • 12054 (21)

    Cities

    • Bethlehem (37)
    • Saugerties (37)
    • Middleburgh (30)
    • Red Hook (30)
    • Hudson (28)
    • Hunter (27)
    • Gilboa (26)
    • Catskill (25)

    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.