Chester, NY Real Estate & Homes For Sale

46 homes

  • 196 Farmingdale Road, Chester, NY 10918
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    NEWOPEN SUN, 1-3PM1 ACRE
    $899,900
    3bd
    3ba
    2,683 sqft (on 1 acre)
    196 Farmingdale Road,
    Chester, NY 10918
    Listing by: RE/MAX Benchmark Realty Group
  • 62 Surrey Road, Chester, NY 10918
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    NEWOPEN SAT, 11-1PM0.42 ACRES
    $475,000
    4bd
    2ba
    1,872 sqft (on 0.42 acres)
    62 Surrey Road,
    Chester, NY 10918
    Listing by: Keller Williams Realty
  • 3 Seely Road, Chester, NY 10918
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    NEWOPEN SAT, 11-1PM0.64 ACRES
    $649,000
    5bd
    3ba
    2,208 sqft (on 0.64 acres)
    3 Seely Road,
    Chester, NY 10918
    Listing by: Howard Hanna Rand Realty
  • 110 Ridge Road, Chester, NY 10918
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    NEW - 2 DAYS AGO1.8 ACRES
    $949,000
    4bd
    4ba
    4,190 sqft (on 1.80 acres)
    110 Ridge Road,
    Chester, NY 10918
    Listing by: BHG Real Estate Green Team
  • 21 Park Drive, Chester, NY 10918
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    0.44 ACRES
    $450,000
    4bd
    2ba
    1,800 sqft (on 0.44 acres)
    21 Park Drive,
    Chester, NY 10918
    Listing by: RE/MAX Benchmark Realty Group
  • 142 Laroe Road, Chester, NY 10918
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    1.6 ACRES
    $609,000
    5bd
    4ba
    3,385 sqft (on 1.60 acres)
    142 Laroe Road,
    Chester, NY 10918
    Listing by: Greene Realty Group
  • 33 Grand View Terrace, Chester, NY 10918
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    0.27 ACRES
    $709,900
    6bd
    4ba
    3,665 sqft (on 0.27 acres)
    33 Grand View Terrace,
    Chester, NY 10918
    Listing by: eXp Realty
  • 1169 Craigville Road, Chester, NY 10918
    0.88 ACRES
    $599,000
    3bd
    2ba
    1,699 sqft (on 0.88 acres)
    1169 Craigville Road,
    Chester, NY 10918
    Listing by: Century 21 Realty Center
  • 47 Valley View Drive, Chester, NY 10918
    5.3 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
    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
    Listing by: Weichert Realtors
  • 9 Eldorado Trl, Chester, NY 10918
    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
  • 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
  • 4 Stevens Place, Chester, NY 10918
    0.48 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
  • 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
  • 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
    OPEN SUN, 1-3PM2 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
    OPEN SUN, 1-4PM1.6 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 $483,081
MonthMedian home value
January 2024$479k
February 2024$481k
March 2024$483k
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 7 new listings and 46 homes for sale in Chester.
Home SizeHome Value*
2 bedrooms (1 home)$287,359
3 bedrooms (8 homes)$430,160
4 bedrooms (19 homes)$607,181
*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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  • Kcouponsdeals
    "this is a great family neighborhood. You can walk to store and NYC bus stop. it's great for kids sports, trick or treating ,etc. there are also arts and theater programs in the area."
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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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  • Missmtrejo
    "It’s a safe community and our neighbors have become friends! We have lived here for 20 years. It’s a great place for children to make friends and feel safe in their environment when they are outside playing. "
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  • Melissa Kyles
    "I lived in Chester when I was a children to adulthood. Great place to live. Outstanding school district. Wish I never moved away."
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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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  • Dawnstephenson42
    "fireworks night football h.s small town feel community garage sales schools mom and pop shops nearby wineries holiday parades farmers market"
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  • Suzzzzzzz64
    "I live in this area for 11 years my neighborhood is great and the people around here are really nice "
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  • Dianerene
    "My commute is excellent. I have a 3 minute commute to the park and ride bus and local stores. Easy to get around by foot if needed."
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  • Ebobec18
    "Safety its a neighborhood very secure the police its annoying but make sense because that its part of what make this place so safe. I can go out at 3pm or 3am and i will fill safe any time. "
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  • Tara R.
    "i love chester unfortunately there arent many houses for purchase in my range for a single mom. wanted my kids to stay in there school there on sports teams."
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