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Homes Under $500K in Chester, NY
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38 listings
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3 bedsNew constructionWith a pool

Homes Under $500K in Chester, NY

Homes Under $500K in Chester, NY

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24 of 38 Listings
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Homes Under $500K in Chester, NY

24 of 38 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 4704 Whispering Hills — photo19Active

    $380,000

    3 bd · 3 ba · 1,331 sqft

    4704 Whispering Hills, Chester, NY

    Evelyn Martino · Sahagian Realty LLC

  2. 3409 Whispering Hills — photo24Active

    $360,000

    3 bd · 3 ba · 1,331 sqft

    3409 Whispering Hills, Chester, NY

    Bernadette Giordano · Howard Hanna Rand Realty

  3. 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

  4. 2124 Whispering Hills — photo18Active

    $299,000

    2 bd · 1 ba · 1,084 sqft

    2124 Whispering Hills, Chester, NY

    Beverly Huaman · Howard Hanna Rand Realty

  5. 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

  6. 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

  7. 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

  8. 4827 New York 8 — photo41Active

    $380,000

    2 bd · 2 ba · 1,350 sqft

    4827 New York 8, Chester, NY

    Vickie Reed · Hunt ERA

  9. 63 Hubshop Road — photo19Active

    $459,000

    4 bd · 3 ba · 2,060 sqft

    63 Hubshop Road, Chester, NY

    Ryan Barrett · Keller Williams Realty

  10. 32 Surrey Road — photoPrice Reduced39Active

    $475,000

    4 bd · 2 ba · 1,820 sqft

    32 Surrey Road, Chester, NY

    Ammar Iqbal · eXp Realty

  11. 36 Ferris Road — photoPrice Reduced52Active

    $365,500

    3 bd · 2 ba · 1,296 sqft

    36 Ferris Road, Chester, NY

    Jenna Frasier · Selling ADK

  12. 1367 Kings Highway — photo16Active

    $440,000

    3 bd · 2 ba · 1,728 sqft

    1367 Kings Highway, Chester, NY

    Derek J. Greene · Greene Realty Group

  13. 22 Spring Street — photoPrice Reduced36Active

    $290,000

    2 bd · 2 ba · 1,021 sqft

    22 Spring Street, Chester, NY

    Jenna Frasier · Selling ADK

  14. 3001 Schroon River Road — photoPrice Reduced35Active

    $459,900

    4 bd · 3 ba · 1,990 sqft

    3001 Schroon River Road, Chester, NY

    Jonathan Minerick · Homecoin.com

  15. 166 Bull Mill Road — photo37Active

    $340,000

    2 bd · 1 ba · 1,004 sqft

    166 Bull Mill Road, Chester, NY

    Stephen Ramundo · Keller Williams Valley Realty

  16. 21 Trotting Drive — photo50Active

    $475,000

    3 bd · 2 ba · 1,624 sqft

    21 Trotting Drive, Chester, NY

    Michele Kayser · Keller Williams Realty

  17. 7 May Road — photoPrice Reduced39Active

    $449,500

    4 bd · 3 ba · 2,058 sqft

    7 May Road, Chester, NY

    Jennifer Ball · Hunt ERA

  18. 70 Main Street — photo27Active

    $469,000

    3 bd · 3 ba · 1,357 sqft

    70 Main Street, Chester, NY

    Pedro Garcia · Curasi Realty, Inc.

  19. 66 Whitetail Run — photo50Active

    $449,000

    3 bd · 2 ba · 1,500 sqft

    66 Whitetail Run, Chester, NY

    Soleil Jackman · Howard Hanna Rand Realty

  20. 2522 Whispering Hills — photo35Active

    $369,000

    3 bd · 3 ba · 1,331 sqft

    2522 Whispering Hills, Chester, NY

    Ann Marie Silvani · Howard Hanna Rand Realty

  21. 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

  22. 33 Meadow Avenue — photo21Active

    $370,000

    3 bd · 1 ba · 1,561 sqft

    33 Meadow Avenue, Chester, NY

    Ernest Acampora · River Realty Services, Inc.

  23. 6380 US. 9 — photoPrice Reduced29Active

    $219,000

    3 bd · 2 ba · 1,624 sqft

    6380 US. 9, Chester, NY

    Corina J Nolin-Strassburg · Howard Hanna

  24. 151 Main Street — photoPrice Reduced16Active

    $299,000

    4 bd · 1 ba · 1,504 sqft

    151 Main Street, Chester, NY

    Eveline R White · Hudson Valley Griffith

12

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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: 2026-08-31 13:45:07 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.