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Chester, NY Homes for Sale — Page 3 | Realty.com
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3 beds
95 listings
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Homes for Sale in Chester, NY

Homes for Sale in Chester, NY

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24 of 95 Listings
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Homes for Sale in Chester, NY

24 of 95 Listings

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TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 7278 US-9 — photoPrice Reduced37Active

    $650,000

    3 bd · 1 ba · 1,220 sqft

    7278 US-9, Chester, NY

    Angela Mead · Gallo Realty ADK Inc

  2. 1 Hilltop Lane — photo1Active

    $750,000

    5 bd · 3 ba · 2,700 sqft

    1 Hilltop Lane, Chester, NY

    Moshe Kaufman · MK Realty Inc

  3. 197 Oxford Road — photo36Active

    $799,000

    4 bd · 3 ba · 3,070 sqft

    197 Oxford Road, Chester, NY

    Regina Carmel · Howard Hanna Rand Realty

  4. 20 Vetter Avenue — photoPrice Reduced28Active

    $320,000

    5 bd · 2 ba · 1,286 sqft

    20 Vetter Avenue, Chester, NY

    Julia Pucciarelli · Gallo Realty ADK Inc

  5. 241 Meadow Avenue — photoPrice Reduced35Active

    $349,999

    4 bd · 2 ba · 1,560 sqft

    241 Meadow Avenue, Chester, NY

    Chativa Bowen · Keller Williams Realty

  6. 14 Vanderwalker Road — photo23Active

    $420,000

    3 bd · 2 ba · 1,488 sqft

    14 Vanderwalker Road, Chester, NY

    Barbara Kearney · Hunt ERA

  7. 190 Kingsley Ln Ext — photoPrice Reduced56Active

    $899,000

    5 bd · 3 ba · 2,482 sqft

    190 Kingsley Ln Ext, Chester, NY

    Brooke Clark · Four Seasons Sothebys International Realty

  8. 2 Hemlock Court — photo3Active

    $750,000

    5 bd · 3 ba · 2,700 sqft

    2 Hemlock Court, Chester, NY

    Moshe Kaufman · MK Realty Inc

  9. 424 Laroe Road — photoPrice Reduced40Active

    $634,999

    4 bd · 3 ba · 2,316 sqft

    424 Laroe Road, Chester, NY

    Jeffrey Morrissey · Epique Realty

  10. 11 Chandler Drive — photoPrice Reduced32Active

    $545,000

    3 bd · 3 ba · 1,908 sqft

    11 Chandler Drive, Chester, NY

    Daniella Restrepo · Coldwell Banker Realty

  11. 5 Hilltop Lane — photo5Active

    $850,000

    5 bd · 3 ba · 3,200 sqft

    5 Hilltop Lane, Chester, NY

    Moshe Kaufman · MK Realty Inc

  12. 12 Theriot Avenue — photoPrice Reduced13Active

    $200,000

    1 bd · 1 ba · 704 sqft

    12 Theriot Avenue, Chester, NY

    Jill Brady · Hunt Real Estate ERA

  13. 985 Craigville Road — photoPrice Reduced36Active

    $750,000

    4 bd · 4 ba · 3,100 sqft

    985 Craigville Road, Chester, NY

    David Deberardinis · Serhant LLC

  14. 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

  15. 856 Olmstedville Road — photoPrice Reduced17Active

    $124,900

    1 bd · 1 ba · 492 sqft

    856 Olmstedville Road, Chester, NY

    Saraha Millington · Gallo Realty ADK Inc

  16. 19 Grand View Terrace — photo37Active

    $789,900

    5 bd · 4 ba · 4,697 sqft

    19 Grand View Terrace, Chester, NY

    Randolph Rogers · eXp Realty

  17. 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

  18. 197 Lane Road — photoPrice Reduced31Active

    $590,000

    3 bd · 3 ba · 2,000 sqft

    197 Lane Road, Chester, NY

    Walter S Swartz · Gallo Realty ADK Inc

  19. 49 Stone Mountain Trail — photo35Active

    $875,000

    4 bd · 3 ba · 3,656 sqft

    49 Stone Mountain Trail, Chester, NY

    Arya Rabinovits · eRealty Advisors, Inc

  20. 1 Oakland Avenue — photoPrice Reduced50Active

    $990,000

    4 bd · 3 ba · 3,955 sqft

    1 Oakland Avenue, Chester, NY

    Christina Rowan · Howard Hanna Rand Realty

  21. 28 Olmstedville Road — photo33Active

    $185,000

    3 bd · 2 ba · 1,540 sqft

    28 Olmstedville Road, Chester, NY

    Heidemarie R Lane · Big Hat Realty

  22. 63 Whitetail Run — photo38Active

    $1,200,000

    4 bd · 3 ba · 2,711 sqft

    63 Whitetail Run, Chester, NY

    Artan Kukaj · SPIRAL NY Real Estate LLC

  23. 19 Bull Mine Road — photo43Active

    $949,000

    4 bd · 3 ba · 3,332 sqft

    19 Bull Mine Road, Chester, NY

    James J. Cosenza · BHG Real Estate Green Team

  24. 3318 State Route 94 — photo29Active

    $549,900

    3 bd · 2 ba · 2,138 sqft

    3318 State Route 94, Chester, NY

    Asha Keegan · Howard Hanna Rand Realty

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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: 2026-09-19 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.

    Nearby areas

    ZIP codes

    • 12603 (125)
    • 12550 (106)
    • 12601 (91)
    • 12401 (80)
    • 12590 (78)
    • 12508 (64)
    • 12790 (58)
    • 12477 (55)

    Cities

    • Poughkeepsie (211)
    • Newburgh (103)
    • Kingston (77)
    • Wappingers Falls (77)
    • Beacon (64)
    • Wurtsboro (56)
    • Saugerties (54)
    • Middletown (52)