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

Homes Under $500K in Chester Town, NY

Homes Under $500K in Chester Town, NY

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20 Listings
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Homes Under $500K in Chester Town, NY

20 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 3706 Whispering Hills — photo17Active

    $339,900

    2 bd · 2 ba · 1,086 sqft

    3706 Whispering Hills, Chester Town, NY

    Randolph Rogers · eXp Realty

  2. 2107 Whispering Hills — photo34Active

    $329,000

    2 bd · 2 ba · 1,086 sqft

    2107 Whispering Hills, Chester Town, NY

    Zachary Leentjes · Wansor Realty

  3. 1223 Whispering Hills — photo18Active

    $299,900

    3 bd · 2 ba · 1,316 sqft

    1223 Whispering Hills, Chester Town, NY

    Jonathon Z. Lee · KW Hudson Valley United

  4. 1212 Whispering Hills — photo48Active

    $269,000

    2 bd · 1 ba · 1,084 sqft

    1212 Whispering Hills, Chester Town, NY

    Beth Palma · Keller Williams Realty

  5. 8 Townsend Place — photo44Active

    $459,000

    4 bd · 2 ba · 1,832 sqft

    8 Townsend Place, Chester Town, NY

    Donna Gennaro · Howard Hanna Rand Realty

  6. 21 Midway Drive — photoPrice Reduced29Active

    $409,000

    3 bd · 1 ba · 1,288 sqft

    21 Midway Drive, Chester Town, NY

    Alyssa Woods · Howard Hanna Rand Realty

  7. 4704 Whispering Hills — photoPrice Reduced19Active

    $370,000

    3 bd · 3 ba · 1,331 sqft

    4704 Whispering Hills, Chester Town, NY

    Evelyn Martino · Sahagian Realty LLC

  8. 2124 Whispering Hills — photoPrice Reduced18Active

    $289,000

    2 bd · 1 ba · 1,084 sqft

    2124 Whispering Hills, Chester Town, NY

    Beverly Huaman · Howard Hanna Rand Realty

  9. 260 Gibson Hill Road — photo22Active

    $374,900

    3 bd · 2 ba · 1,644 sqft

    260 Gibson Hill Road, Chester Town, NY

    Camilia Anka · Keller Williams Realty

  10. 2921 Whispering Hills — photoPrice Reduced42Active

    $364,900

    3 bd · 3 ba · 1,331 sqft

    2921 Whispering Hills, Chester Town, NY

    Amanda M Dnistrian · ARC Realty 1 in Sales

  11. 1005 Whispering Hills — photo28Active

    $290,000

    2 bd · 2 ba · 1,053 sqft

    1005 Whispering Hills, Chester Town, NY

    Kristie A. Jacques · Century 21 Full Service Realty

  12. 74 Heaton Road — photo23Active

    $500,000

    3 bd · 2 ba · 1,676 sqft

    74 Heaton Road, Chester Town, NY

    Barbara R Bloch · Coldwell Banker Realty

  13. 1367 Kings Highway — photo16Active

    $440,000

    3 bd · 2 ba · 1,728 sqft

    1367 Kings Highway, Chester Town, NY

    Derek J. Greene · Greene Realty Group

  14. 70 Main Street — photo27Active

    $469,000

    3 bd · 3 ba · 1,357 sqft

    70 Main Street, Chester Town, NY

    Pedro Garcia · Curasi Realty, Inc.

  15. 2522 Whispering Hills — photoPrice Reduced35Active

    $359,000

    3 bd · 3 ba · 1,331 sqft

    2522 Whispering Hills, Chester Town, NY

    Ann Marie Silvani · Howard Hanna Rand Realty

  16. 33 Meadow Avenue — photo21Active

    $370,000

    3 bd · 1 ba · 1,561 sqft

    33 Meadow Avenue, Chester Town, NY

    Ernest Acampora · River Realty Services, Inc.

  17. 151 Main Street — photoPrice Reduced16Active

    $299,000

    4 bd · 1 ba · 1,504 sqft

    151 Main Street, Chester Town, NY

    Eveline R White · Hudson Valley Griffith

  18. 241 Meadow Avenue — photoPrice Reduced35Active

    $349,999

    4 bd · 2 ba · 1,560 sqft

    241 Meadow Avenue, Chester Town, NY

    Chativa Bowen · Keller Williams Realty

  19. 11 Chandler Drive — photoPrice Reduced32Active

    $499,999

    3 bd · 3 ba · 1,908 sqft

    11 Chandler Drive, Chester Town, NY

    Daniella Restrepo · Coldwell Banker Realty

  20. 2113 Whispering Hills — photoPrice Reduced24Active

    $275,000

    2 bd · 1 ba · 1,084 sqft

    2113 Whispering Hills, Chester Town, NY

    Valerie Quinn · Keller Williams Realty

Explore Chester Town homes

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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
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #10311208632

    Call Thomas