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Homes with a Pool in Chester, NY
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15 listings
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3 bedsNew constructionWith a pool

Homes with a Pool in Chester, NY

Homes with a Pool in Chester, NY

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15 Listings
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Homes with a Pool in Chester, NY

15 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 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

  2. 20 Mountainside Drive — photo36Active

    $749,900

    4 bd · 4 ba · 3,080 sqft

    20 Mountainside Drive, Chester, NY

    Randolph Rogers · eXp Realty

  3. 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

  4. 412 Laroe Road — photo46Active

    $615,000

    3 bd · 2 ba · 1,848 sqft

    412 Laroe Road, Chester, NY

    Nathalie M Sessoms · Howard Hanna Rand Realty

  5. 7 Lakeview Drive — photo29Active

    $549,999

    4 bd · 3 ba · 2,098 sqft

    7 Lakeview Drive, Chester, NY

    Sheyla L. Falesto · Howard Hanna Rand Realty

  6. 11 Chandler Drive — photoPrice Reduced32Active

    $545,000

    3 bd · 3 ba · 1,908 sqft

    11 Chandler Drive, Chester, NY

    Daniella Restrepo · Coldwell Banker Realty

  7. 985 Craigville Road — photoPrice Reduced36Active

    $750,000

    4 bd · 4 ba · 3,100 sqft

    985 Craigville Road, Chester, NY

    David Deberardinis · Serhant LLC

  8. 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

  9. 58 Nancy Lane — photoPrice Reduced49Active

    $749,999

    3 bd · 3 ba · 2,718 sqft

    58 Nancy Lane, Chester, NY

    Gina Dudgeon · Howard Hanna Rand Realty

  10. 19 High Street — photoPrice Reduced50Active

    $1,145,000

    9 bd · 7 ba · 4,965 sqft

    19 High Street, Chester, NY

    Beth Palma · Keller Williams Realty

  11. 19 Greentree Lane — photo50Active

    $3,400,000

    4 bd · 4 ba · 7,750 sqft

    19 Greentree Lane, Chester, NY

    Jake Garay · Serhant LLC

  12. 2 Primrose Lane — photo42Active

    $849,900

    4 bd · 3 ba · 2,370 sqft

    2 Primrose Lane, Chester, NY

    Janet A Rendle · Weichert Realtors

  13. 16 Lori Lane — photoPrice Reduced41Active

    $1,139,900

    4 bd · 5 ba · 4,624 sqft

    16 Lori Lane, Chester, NY

    Randolph Rogers · eXp Realty

  14. 6324 State Route 9 — photoPrice Reduced38Active

    $424,900

    6 bd · 3 ba · 2,916 sqft

    6324 State Route 9, Chester, NY

    Robert Saumell Jr. · KW Platform

  15. 12 Damian Court — photoPrice Reduced34Active

    $949,000

    5 bd · 4 ba · 3,136 sqft

    12 Damian Court, Chester, NY

    Elimelech Kremer · MS Realty Group USA, Inc

Explore Chester homes

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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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: 2026-08-05 13:37:14 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.