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4 Bedroom Homes in Chester, NY
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37 listings
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3 bedsNew constructionWith a pool

4 Bedroom Homes in Chester, NY

4 Bedroom Homes in Chester, NY

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24 of 37 Listings
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4 Bedroom Homes in Chester, NY

24 of 37 Listings

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Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 1168 Craigville Road — photo37Active

    $779,900

    4 bd · 3 ba · 2,616 sqft

    1168 Craigville Road, Chester, NY

    Amanda M Dnistrian · ARC Realty 1 in Sales

  2. 101 Beverly Road — photo31Active

    $879,000

    4 bd · 4 ba · 3,764 sqft

    101 Beverly Road, Chester, NY

    Derek J. Greene · Greene Realty Group

  3. 8 Townsend Place — photo44Active

    $459,000

    4 bd · 2 ba · 1,832 sqft

    8 Townsend Place, Chester, NY

    Donna Gennaro · Howard Hanna Rand Realty

  4. 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

  5. 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

  6. 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

  7. 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

  8. 13 Bianca Boulevard — photo49Active

    $700,000

    4 bd · 3 ba · 3,296 sqft

    13 Bianca Boulevard, Chester, NY

    Theresa M Powers · Keller Williams Realty

  9. 1 Sanford Avenue — photo32Active

    $750,000

    4 bd · 3 ba · 2,280 sqft

    1 Sanford Avenue, Chester, NY

    Danielle R. Hinton · Redfin Real Estate

  10. 63 Hubshop Road — photo19Active

    $459,000

    4 bd · 3 ba · 2,060 sqft

    63 Hubshop Road, Chester, NY

    Ryan Barrett · Keller Williams Realty

  11. 32 Surrey Road — photoPrice Reduced39Active

    $475,000

    4 bd · 2 ba · 1,820 sqft

    32 Surrey Road, Chester, NY

    Ammar Iqbal · eXp Realty

  12. 34 Boville Court — photo46Active

    $839,000

    4 bd · 4 ba · 2,707 sqft

    34 Boville Court, Chester, NY

    Jillian Laga · Keller Williams Valley Realty

  13. 20 Mountainside Drive — photo36Active

    $749,900

    4 bd · 4 ba · 3,080 sqft

    20 Mountainside Drive, Chester, NY

    Randolph Rogers · eXp Realty

  14. 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

  15. 548 White Schoolhouse Road — photo38Active

    $585,000

    4 bd · 2 ba · 1,948 sqft

    548 White Schoolhouse Road, Chester, NY

    Carol Monroe · Najer 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. 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

  18. 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

  19. 197 Oxford Road — photo36Active

    $799,000

    4 bd · 3 ba · 3,070 sqft

    197 Oxford Road, Chester, NY

    Regina Carmel · Howard Hanna Rand Realty

  20. 241 Meadow Avenue — photoPrice Reduced35Active

    $349,999

    4 bd · 2 ba · 1,560 sqft

    241 Meadow Avenue, Chester, NY

    Chativa Bowen · Keller Williams Realty

  21. 424 Laroe Road — photoPrice Reduced40Active

    $634,999

    4 bd · 3 ba · 2,316 sqft

    424 Laroe Road, Chester, NY

    Jeffrey Morrissey · Epique Realty

  22. 985 Craigville Road — photoPrice Reduced36Active

    $750,000

    4 bd · 4 ba · 3,100 sqft

    985 Craigville Road, Chester, NY

    David Deberardinis · Serhant LLC

  23. 342-346 Starbuck Hill Road — photo45Active

    $699,900

    4 bd · 3 ba · 3,977 sqft

    342-346 Starbuck Hill Road, Chester, NY

    Holly Dansbury · Davies Davies & Associates Real Estate LLC

  24. 22 Goshen Road — photo50Active

    $1,195,000

    4 bd · 4 ba · 4,281 sqft

    22 Goshen Road, Chester, NY

    Martha Randazzo · Howard Hanna Rand Realty

12

Explore Chester homes

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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: 2026-09-19 13:34:27 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

    August 2026 · This period is still settling

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 13 sales · as of Aug 28, 2026

    Homes on the market · MLS, as of Aug 24, 2026–Aug 28, 2026

    Median list price
    $699,998
    Homes for sale
    74
    Median days on market
    41 days

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 19, 2026

    Median home size
    2,097 sq. ft.