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Chester, NY Homes for Sale — Page 2 | Realty.com
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3 beds
98 listings
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New construction
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Homes for Sale in Chester, NY

Homes for Sale in Chester, NY

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24 of 98 Listings
Map

Homes for Sale in Chester, NY

24 of 98 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 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

  2. 1 Sanford Avenue — photo32Active

    $750,000

    4 bd · 3 ba · 2,280 sqft

    1 Sanford Avenue, Chester, NY

    Danielle R. Hinton · Redfin Real Estate

  3. 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

  4. 4827 New York 8 — photo41Active

    $380,000

    2 bd · 2 ba · 1,350 sqft

    4827 New York 8, Chester, NY

    Vickie Reed · Hunt ERA

  5. 173 Creamery Pond Road — photoPrice Reduced48Active

    $669,000

    3 bd · 3 ba · 2,533 sqft

    173 Creamery Pond Road, Chester, NY

    Michele Tobin · Keller Williams Realty

  6. 63 Hubshop Road — photo19Active

    $459,000

    4 bd · 3 ba · 2,060 sqft

    63 Hubshop Road, Chester, NY

    Ryan Barrett · Keller Williams Realty

  7. 32 Surrey Road — photoPrice Reduced39Active

    $475,000

    4 bd · 2 ba · 1,820 sqft

    32 Surrey Road, Chester, NY

    Ammar Iqbal · eXp Realty

  8. 36 Ferris Road — photoPrice Reduced52Active

    $349,900

    3 bd · 2 ba · 1,296 sqft

    36 Ferris Road, Chester, NY

    Jenna Frasier · Selling ADK

  9. 34 Boville Court — photo46Active

    $839,000

    4 bd · 4 ba · 2,707 sqft

    34 Boville Court, Chester, NY

    Jillian Laga · Keller Williams Valley Realty

  10. 20 Mountainside Drive — photo36Active

    $749,900

    4 bd · 4 ba · 3,080 sqft

    20 Mountainside Drive, Chester, NY

    Randolph Rogers · eXp Realty

  11. 1367 Kings Highway — photo16Active

    $440,000

    3 bd · 2 ba · 1,728 sqft

    1367 Kings Highway, Chester, NY

    Derek J. Greene · Greene Realty Group

  12. 3 Garnett Hill Road — photo50Active

    $799,000

    4 bd · 3 ba · 2,516 sqft

    3 Garnett Hill Road, Chester, NY

    Jacob Fried · Keller Williams Realty

  13. 548 White Schoolhouse Road — photo38Active

    $585,000

    4 bd · 2 ba · 1,948 sqft

    548 White Schoolhouse Road, Chester, NY

    Carol Monroe · Najer Realty

  14. 22 Spring Street — photoPrice Reduced36Active

    $290,000

    2 bd · 2 ba · 1,021 sqft

    22 Spring Street, Chester, NY

    Jenna Frasier · Selling ADK

  15. 412 Laroe Road — photoPrice Reduced46Active

    $605,000

    3 bd · 2 ba · 1,848 sqft

    412 Laroe Road, Chester, NY

    Nathalie M Sessoms · Howard Hanna Rand Realty

  16. 3001 Schroon River Road — photoPrice Reduced35Active

    $439,900

    4 bd · 3 ba · 1,990 sqft

    3001 Schroon River Road, Chester, NY

    Jonathan Minerick · Homecoin.com

  17. 166 Bull Mill Road — photoPrice Reduced37Active

    $289,000

    2 bd · 1 ba · 1,004 sqft

    166 Bull Mill Road, Chester, NY

    Stephen Ramundo · Keller Williams Valley Realty

  18. 84 Marina Road — photo35Active

    $639,000

    3 bd · 2 ba · 1,806 sqft

    84 Marina Road, Chester, NY

    Sandra S Engle Pratt · Gore Mountain Real Estate Company

  19. 21 Trotting Drive — photo50Active

    $475,000

    3 bd · 2 ba · 1,624 sqft

    21 Trotting Drive, Chester, NY

    Michele Kayser · Keller Williams Realty

  20. 70 Main Street — photo27Active

    $469,000

    3 bd · 3 ba · 1,357 sqft

    70 Main Street, Chester, NY

    Pedro Garcia · Curasi Realty, Inc.

  21. 66 Whitetail Run — photoPrice Reduced50Active

    $435,000

    3 bd · 2 ba · 1,500 sqft

    66 Whitetail Run, Chester, NY

    Soleil Jackman · Howard Hanna Rand Realty

  22. 7189 US. 9 — photoPrice Reduced36Active

    $475,500

    4 bd · 2 ba · 1,369 sqft

    7189 US. 9, Chester, NY

    Julia Pucciarelli · Gallo Realty ADK Inc

  23. 2522 Whispering Hills — photoPrice Reduced35Active

    $359,000

    3 bd · 3 ba · 1,331 sqft

    2522 Whispering Hills, Chester, NY

    Ann Marie Silvani · Howard Hanna Rand Realty

  24. 26 Emily Lane — photoPrice Reduced62Active

    $795,000

    3 bd · 3 ba · 1,476 sqft

    26 Emily Lane, Chester, NY

    Walter S Swartz · Gallo Realty ADK Inc

123…5

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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: 2026-09-17 12:46:26 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

    • 10950 (194)
    • 10940 (144)
    • 12550 (115)
    • 10901 (100)
    • 10977 (88)
    • 12603 (82)
    • 12553 (75)
    • 10918 (70)

    Cities

    • Monroe (182)
    • Middletown (165)
    • Poughkeepsie (132)
    • Newburgh (112)
    • Suffern (91)
    • Spring Valley (84)
    • New Windsor (75)
    • Warwick (68)