Chester, NY Real Estate & Homes For Sale

46 homes

  • 1169 Craigville Road, Chester, NY 10918
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    NEW - 2 HRS AGO0.88 ACRES
    $599,000
    3bd
    2ba
    1,699 sqft (on 0.88 acres)
    1169 Craigville Road,
    Chester, NY 10918
    Listing by: Century 21 Realty Center
  • 40 Farmingdale Road, Chester, NY 10918
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    NEW - 9 HRS AGO4.3 ACRES
    $650,000
    4bd
    3ba
    2,269 sqft (on 4.30 acres)
    40 Farmingdale Road,
    Chester, NY 10918
    Listing by: Keller Williams Realty
  • 1311 Whispering Hills Drive, Chester, NY 10918
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    NEW - 1 DAY AGO
    Listing by: Howard Hanna Rand Realty
  • 47 Valley View Drive, Chester, NY 10918
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    NEW - 1 DAY AGO5.3 ACRES
    $699,000
    5bd
    4ba
    3,812 sqft (on 5.30 acres)
    47 Valley View Drive,
    Chester, NY 10918
    Listing by: Keller Williams Realty
  • 118 Murray Drive, Chester, NY 10918
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    2.8 ACRES
    $949,900
    4bd
    4ba
    3,418 sqft (on 2.80 acres)
    118 Murray Drive,
    Chester, NY 10918
    Listing by: ARC Realty 1 in Sales
  • 3317 Whispering Hills, Chester, NY 10918
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    Listing by: Weichert Realtors
  • 9 Eldorado Trl, Chester, NY 10918
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    2.4 ACRES
    $949,000
    4bd
    5ba
    3,500 sqft (on 2.40 acres)
    9 Eldorado Trl,
    Chester, NY 10918
    Listing by: EXP Realty
  • 9 El Dorado Trail, Chester, NY 10918
    NEW CONSTRUCTION2.4 ACRES
    $949,000
    4bd
    5ba
    3,500 sqft (on 2.40 acres)
    9 El Dorado Trail,
    Chester, NY 10918
    Listing by: EXP Realty
  • 1110 Whispering Hills Drive, Chester, NY 10918
    Listing by: Keller Williams Realty
  • 4703 Whispering Hills, Chester, NY 10918
    Listing by: Reliable Realty Group
  • 4116 Whispering Hills, Chester, NY 10918
    Listing by: Keller Williams NY Realty
  • 1 Bamond Court, Chester, NY 10918
    2.6 ACRES
    $749,000
    3bd
    4ba
    3,209 sqft (on 2.60 acres)
    1 Bamond Court,
    Chester, NY 10918
    Listing by: Avion
  • 21 Kerner Drive, Chester, NY 10918
    0.34 ACRES
    $439,900
    3bd
    2ba
    1,594 sqft (on 0.34 acres)
    21 Kerner Drive,
    Chester, NY 10918
    Listing by: RE/MAX Town & Country
  • 65 Oxford Springs Road, Chester, NY 10918
    2.3 ACRES
    $899,999
    5bd
    4ba
    4,657 sqft (on 2.30 acres)
    65 Oxford Springs Road,
    Chester, NY 10918
    Listing by: eXp Realty
  • 88 Nancy Lane, Chester, NY 10918
    FORECLOSURE1.6 ACRES
    $522,050
    4bd
    3ba
    2,768 sqft (on 1.60 acres)
    88 Nancy Lane,
    Chester, NY 10918
    Listing by: REALHome Services & Solutions
  • 58 Wood Road, Chester, NY 10918
    $799,900
    3bd
    3ba
    2,868 sqft
    58 Wood Road,
    Chester, NY 10918
    Listing by: RE/MAX Benchmark Realty Group
  • 6 Silvertail Road, Chester, NY 10918
    7.9 ACRES
    $1,649,000
    6bd
    5ba
    5,127 sqft (on 7.90 acres)
    6 Silvertail Road,
    Chester, NY 10918
    Listing by: Ellis Sotheby's Intl Realty
  • 38 Park Drive, Chester, NY 10918
    0.98 ACRES
    $600,000
    5bd
    4ba
    2,770 sqft (on 0.98 acres)
    38 Park Drive,
    Chester, NY 10918
    Listing by: Howard Hanna Rand Realty
  • 4 Stevens Place, Chester, NY 10918
    OPEN SUN, 12-2PM0.48 ACRES
    $499,000
    3bd
    2ba
    1,882 sqft (on 0.48 acres)
    4 Stevens Place,
    Chester, NY 10918
    Listing by: Weichert Realtors
  • 90 Main (1 Oakland Ave) Street, Chester, NY 10918
    9.68 ACRES
    $1,400,000
    6bd
    4ba
    4,837 sqft (on 9.68 acres)
    90 Main (1 Oakland Ave) Street,
    Chester, NY 10918
    Listing by: Ellis Sotheby's Intl Realty
  • 220 Oxford Road, Chester, NY 10918
    6.3 ACRES
    $850,000
    4bd
    4ba
    3,535 sqft (on 6.30 acres)
    220 Oxford Road,
    Chester, NY 10918
    Listing by: eRealty Advisors, Inc
  • 25 Natures Trail, Chester, NY 10918
    2.6 ACRES
    $799,000
    4bd
    3ba
    3,115 sqft (on 2.60 acres)
    25 Natures Trail,
    Chester, NY 10918
    Listing by: eXp Realty
  • 322 Black Meadow Road, Chester, NY 10918
    5.7 ACRES
    $669,999
    4bd
    3ba
    2,394 sqft (on 5.70 acres)
    322 Black Meadow Road,
    Chester, NY 10918
    Listing by: N Tirado Realty LLC
  • 10 Silvertail Road, Chester, NY 10918
    5 ACRES
    $1,500,000
    4bd
    5ba
    5,007 sqft (on 5 acres)
    10 Silvertail Road,
    Chester, NY 10918
    Listing by: eXp Realty
  •  Oxford Road, Chester, NY 10918
    5.4 ACRES
    Listing by: RE/MAX Benchmark Realty Group
  • 221 Oxford Road, Oxford, NY 10918
    3.9 ACRES
    $999,999
    4bd
    4ba
    4,644 sqft (on 3.90 acres)
    221 Oxford Road,
    Oxford, NY 10918
    Listing by: RE/MAX Benchmark Realty Group
  • 8 Kings Highway, Chester, NY 10918
    3.75 ACRES
    Listing by: BHHS Hudson Valley Properties
  • 282 Laroe Road, Chester, NY 10918
    10.2 ACRES
    $1,250,000
    6bd
    5ba
    6,622 sqft (on 10.20 acres)
    282 Laroe Road,
    Chester, NY 10918
    Listing by: Ellis Sotheby's Intl Realty
  • 1414 Kings Highway, Chester, NY 10918
    4.5 ACRES
    Listing by: Keller Williams Realty
  •  Summerville Way, Chester, NY 10918
    1.31 ACRES
    Listing by: Keller Williams Hudson Valley
  • 3 Seely Road, Chester, NY 10918
    0.64 ACRES
    $649,000
    5bd
    3ba
    2,208 sqft (on 0.64 acres)
    3 Seely Road,
    Chester, NY 10918
    Listing by: Blooming Realty
  • 16 Meadow Avenue, Chester, NY 10918
    0.28 ACRES
    $615,000
    4bd
    2ba
    1,568 sqft (on 0.28 acres)
    16 Meadow Avenue,
    Chester, NY 10918
    Listing by: eXp Realty
  • 226 Glenmere Road, Chester, NY 10918
    2 ACRES
    $496,400
    4bd
    2ba
    1,530 sqft (on 2 acres)
    226 Glenmere Road,
    Chester, NY 10918
    Listing by: Howard Hanna Rand Realty
  • 10 El Dorado Trail, Chester, NY 10918
    6.3 ACRES
    Listing by: Keller Williams Realty
  • 6 Lookout Terrace, Chester, NY 10918
    2.2 ACRES
    Listing by: Howard Hanna Rand Realty
  •  Craigville Road, Chester, NY 10918
    19.8 ACRES
    Listing by: Compass Greater NY, LLC
  • 559 Laroe Road, Chester, NY 10918
    0.71 ACRES
    $350,000
    3bd
    3ba
    1,900 sqft (on 0.71 acres)
    559 Laroe Road,
    Chester, NY 10918
    Listing by: McGrath Realty Inc
  • 24 Woodridge Drive, Chester, NY 10918
    1.6 ACRES
    $599,000
    4bd
    3ba
    2,680 sqft (on 1.60 acres)
    24 Woodridge Drive,
    Chester, NY 10918
    Listing by: eXp Realty
  • 32 Mountainside Drive, Chester, NY 10918
    20.18 ACRES
    $979,900
    4bd
    4ba
    2,720 sqft (on 20.18 acres)
    32 Mountainside Drive,
    Chester, NY 10918
    Listing by: Our House Real Estate Group
  •  Kings Highway Bypass, Chester, NY 10918
    3.8 ACRES
    Listing by: Keller Williams Realty

Chester, NY Real Estate Trends

Learn about the Chester, NY housing market through trends and averages.

Affordability of Living in Chester, NY

The median home value is $475,517
MonthMedian home value
January 2024$474k
February 2024$476k
View as a graph
Trends and affordability stats are provided by third party data sources.

Average Home Value in Chester, NY, by Home Size

Currently, there are 6 new listings and 46 homes for sale in Chester.
Home SizeHome Value*
2 bedrooms (2 homes)$282,375
3 bedrooms (9 homes)$422,972
4 bedrooms (17 homes)$597,456
*Home value over the past month

What Locals Say about Chester

  • Trulia User
    "There's plenty of areas with sidewalks to walk your dog throughout most of town. My apartment complex has a dog park "
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  • Jennifer G.
    "I have two years living here. Great place to raise a family. Friendly and safe neighborhood. The kids love it as well."
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  • Kcouponsdeals
    "this is a great village, and neighborhood to live in lots of community involvement, family activities, close to transportation and shopping."
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  • DEIRDRE B.
    "I take the Shortline bus to NYC. 1 hour and 15 minutes more or less plus train from Port. It’s about $450/month including Metrocard. Shortline has become less reliable recently. "
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  • Dianerene
    "Street fairs, community parades, concerts and so much more. The location is awesome and neighbors aren’t overly nosy yet friendly."
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