140

Recently Sold Chester, NY Homes

Section Image
  • 10 Damian Ct, Chester, NY 10918

    $1,225,000

    Sold Apr 17, 2026

    10 Damian Ct, Chester, NY 10918

    • 11 Beds
    • 6.5 Baths
    • 4,327 Sq Ft
    • Built 2004

    Last Sold Summary

    • 11% Below List Price
    • $283/SF
    • 47 Days On Market

    Current Estimated Value $1,216,706

    Last Listing Agent Elimelech Kremer MS Realty Group USA, Inc

    10 Damian Ct, Chester, NY 10918
  • 25 Sugarloaf Mountain Rd, Chester, NY 10918

    $635,000

    Sold Jun 22, 2026

    25 Sugarloaf Mountain Rd, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,954 Sq Ft
    • Built 1999

    Last Sold Summary

    • $325/SF
    • 29 Days On Market

    Current Estimated Value $630,676

    Last Listing Agent Frank Muccari Cronin & Company Real Estate

    25 Sugarloaf Mountain Rd, Chester, NY 10918
  • /9

    $43,000

    Sold Oct 31, 2025

    L17 Vanderwalker Rd, Chester, NY 12817

    • Land
    • 4 Acres
    • $10,750 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 5 Days On Market

    Last Listing Agent Zachary Layton Four Seasons Sotheby's International Realty

    L17 Vanderwalker Rd, Chester, NY 12817
  • 2912 Whispering Hills, Chester, NY 10918

    $320,000

    Sold Mar 11, 2026

    2912 Whispering Hills, Chester, NY 10918

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft
    • Built 1987

    Last Sold Summary

    • 5% Above List Price
    • $295/SF
    • 19 Days On Market

    Current Estimated Value $313,526

    Last Listing Agent Rebecca Matta-Candela Keller Williams Realty

    2912 Whispering Hills, Chester, NY 10918
  • 2104 Whispering Hills, Chester, NY 10918

    $260,000

    Sold Mar 11, 2026

    2104 Whispering Hills, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft
    • Built 1984

    Last Sold Summary

    • 13% Below List Price
    • $195/SF
    • 24 Days On Market

    Current Estimated Value $283,151

    Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

    2104 Whispering Hills, Chester, NY 10918
  • 52 Wilson Rd, Monroe, NY 10950

    $588,000

    Sold Aug 07, 2026

    52 Wilson Rd, Monroe, NY 10950

    • 4 Beds
    • 3 Baths
    • 1,846 Sq Ft
    • Built 1977

    Last Sold Summary

    • 4% Above List Price
    • $319/SF
    • 22 Days On Market

    Current Estimated Value $557,558

    Last Listing Agent Claudia Lepore Keller Williams Realty

    52 Wilson Rd, Monroe, NY 10950
  • 3308 Whispering Hills Dr, Chester, NY 10918

    $290,000

    Sold Apr 09, 2026

    3308 Whispering Hills Dr, Chester, NY 10918

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Below List Price
    • $271/SF
    • 39 Days On Market

    Current Estimated Value $294,428

    Last Listing Agent Joseph Paoli Howard Hanna Rand Realty

    3308 Whispering Hills Dr, Chester, NY 10918
  • 98 High St, Chester, NY 10918

    $323,500

    Sold Aug 11, 2025

    98 High St, Chester, NY 10918

    • 4 Beds
    • 1.5 Baths
    • 1,360 Sq Ft
    • Built 1950

    Last Sold Summary

    • 5% Below List Price
    • $238/SF
    • 35 Days On Market

    Current Estimated Value $348,393

    Last Listing Agent Zachary Foley eXp Realty

    98 High St, Chester, NY 10918
  • 44 Cedar Pond Ln, Chester, NY 10918

    $610,000

    Sold Mar 12, 2026

    44 Cedar Pond Ln, Chester, NY 10918

    • 3 Beds
    • 2 Baths
    • 1,876 Sq Ft
    • Built 1991

    Last Sold Summary

    • 2% Above List Price
    • $325/SF
    • 48 Days On Market

    Current Estimated Value $655,404

    Last Listing Agent Ammar Iqbal eXp Realty

    44 Cedar Pond Ln, Chester, NY 10918
  • 2812 Whispering Hills Unit 577, Chester, NY 10918

    $320,000

    Sold Feb 13, 2026

    2812 Whispering Hills Unit 577, Chester, NY 10918

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft
    • Built 1984

    Last Sold Summary

    • 10% Above List Price
    • $295/SF
    • 22 Days On Market

    Current Estimated Value $316,294

    Last Listing Agent Kathy White Exit Realty Connections

    2812 Whispering Hills Unit 577, Chester, NY 10918
  • 4703 Whispering Hills Dr, Chester, NY 10918

    $382,000

    Sold Jan 12, 2026

    4703 Whispering Hills Dr, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft
    • Built 1991

    Last Sold Summary

    • 4% Above List Price
    • $287/SF
    • 61 Days On Market

    Current Estimated Value $372,671

    Last Listing Agent Erin Connolly-Frontino Artisan Realty

    4703 Whispering Hills Dr, Chester, NY 10918
  • 12 Bianca Blvd, Chester, NY 10918

    $575,000

    Sold Sep 23, 2025

    12 Bianca Blvd, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 3,200 Sq Ft
    • Built 1987

    Last Sold Summary

    • 2% Below List Price
    • $180/SF
    • 126 Days On Market

    Current Estimated Value $656,993

    Last Listing Agent Aoife Freeman eXp Realty

    12 Bianca Blvd, Chester, NY 10918
  • /17

    $58,900

    Sold Jun 12, 2026

    71 Carriage Knoll Rd, Chester, NY 12817

    • Land
    • 1.89 Acres
    • $31,164 per Acre

    Last Sold Summary

    • 39% Above List Price
    • 576 Days On Market

    Last Listing Agent Walter Swartz Gallo Realty ADK Inc

    71 Carriage Knoll Rd, Chester, NY 12817
  • 7 Park Place, Chester, NY 10918

    $700,000

    Sold Jul 08, 2026

    7 Park Place, Chester, NY 10918

    • 4 Beds
    • 3.5 Baths
    • 2,780 Sq Ft
    • Built 1986

    Last Sold Summary

    • 5% Below List Price
    • $252/SF
    • 196 Days On Market

    Current Estimated Value $735,662

    Last Listing Agent Luanne McGann Century 21 Full Service Realty

    7 Park Place, Chester, NY 10918
  • 4508 Whispering Hills, Chester, NY 10918

    $300,000

    Sold Apr 20, 2026

    4508 Whispering Hills, Chester, NY 10918

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • Built 1987

    Last Sold Summary

    • 8% Below List Price
    • $280/SF
    • 44 Days On Market

    Current Estimated Value $301,305

    Last Listing Agent Ammar Iqbal eXp Realty

    4508 Whispering Hills, Chester, NY 10918
  • 9 June Rd, Chester, NY 10918

    $620,000

    Sold Oct 29, 2025

    9 June Rd, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,402 Sq Ft
    • Built 1999

    Last Sold Summary

    • 4% Below List Price
    • $258/SF
    • 52 Days On Market

    Current Estimated Value $629,498

    Last Listing Agent Jason Madison eXp Realty

    9 June Rd, Chester, NY 10918
  • 3708 Whispering Hills, Chester, NY 10918

    $310,000

    Sold Nov 10, 2025

    3708 Whispering Hills, Chester, NY 10918

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • Built 1990

    Last Sold Summary

    • 5% Above List Price
    • $289/SF
    • 26 Days On Market

    Current Estimated Value $310,182

    Last Listing Agent Nikki Grzegorzewski Keller Williams Realty

    3708 Whispering Hills, Chester, NY 10918
  • 23 Renies Rd, Chester, NY 10918

    $644,000

    Sold Feb 12, 2026

    23 Renies Rd, Chester, NY 10918

    • 3 Beds
    • 3 Baths
    • 3,200 Sq Ft
    • Built 1990

    Last Sold Summary

    • 7% Below List Price
    • $201/SF
    • 100 Days On Market

    Current Estimated Value $676,117

    Last Listing Agent Kristie Jacques Century 21 Full Service Realty

    23 Renies Rd, Chester, NY 10918
  • 27 Grand View Terrace, Chester, NY 10918

    $780,000

    Sold Aug 15, 2025

    27 Grand View Terrace, Chester, NY 10918

    • 5 Beds
    • 3.5 Baths
    • 4,490 Sq Ft
    • Built 2004

    Last Sold Summary

    • 3% Above List Price
    • $174/SF
    • 43 Days On Market

    Current Estimated Value $801,761

    Last Listing Agent Randolph Rogers eXp Realty

    27 Grand View Terrace, Chester, NY 10918
  • 68 Southside Dr, Monroe, NY 10950

    $380,000

    Sold Sep 15, 2025

    68 Southside Dr, Monroe, NY 10950

    • 3 Beds
    • 2 Baths
    • 1,632 Sq Ft
    • Built 1940

    Last Sold Summary

    • 15% Below List Price
    • $233/SF
    • 49 Days On Market

    Current Estimated Value $419,618

    Last Listing Agent Carol Buchanan BHG Real Estate Green Team

    68 Southside Dr, Monroe, NY 10950
  • 284 Bull Mill Rd, Chester, NY 10918

    $850,000

    Sold Oct 22, 2025

    284 Bull Mill Rd, Chester, NY 10918

    • 5 Beds
    • 3 Baths
    • 3,485 Sq Ft
    • Built 1997

    Last Sold Summary

    • $244/SF
    • 20 Days On Market

    Current Estimated Value $841,269

    Last Listing Agent Jayne M. Prechtel Keller Williams Valley Realty

    284 Bull Mill Rd, Chester, NY 10918
  • 1 Winding Trail, Chester, NY 10918

    $540,000

    Sold Aug 28, 2025

    1 Winding Trail, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 2,040 Sq Ft
    • Built 1991

    Last Sold Summary

    • 10% Below List Price
    • $265/SF
    • 35 Days On Market

    Current Estimated Value $551,142

    Last Listing Agent Donald Serotta Howard Hanna Rand Realty

    1 Winding Trail, Chester, NY 10918
  • 411 Prospect Rd, Chester, NY 10918

    $610,000

    Sold Aug 25, 2025

    411 Prospect Rd, Chester, NY 10918

    • 4 Beds
    • 2 Baths
    • 1,987 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Above List Price
    • $307/SF
    • 39 Days On Market

    Current Estimated Value $614,168

    Last Listing Agent Dana Posner Howard Hanna Rand Realty

    411 Prospect Rd, Chester, NY 10918
  • 4 Oak St, Chester, NY 10918

    $525,000

    Sold Jul 01, 2026

    4 Oak St, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,888 Sq Ft
    • Built 1967

    Last Sold Summary

    • 5% Above List Price
    • $278/SF
    • 27 Days On Market

    Current Estimated Value $507,232

    Last Listing Agent Frank Muccari Cronin & Company Real Estate

    4 Oak St, Chester, NY 10918
  • 226 Eagleton Dr, Monroe, NY 10950

    $365,000

    Sold Sep 12, 2025

    226 Eagleton Dr, Monroe, NY 10950

    • 3 Beds
    • 2.5 Baths
    • 1,698 Sq Ft
    • Built 1997

    Last Sold Summary

    • 3% Below List Price
    • $215/SF
    • 16 Days On Market

    Current Estimated Value $389,957

    Last Listing Agent Lorrainne Pisciotta Weichert Realtors

    226 Eagleton Dr, Monroe, NY 10950
  • 1071 Craigville Rd, Chester, NY 10918

    $770,000

    Sold Jun 25, 2026

    1071 Craigville Rd, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,780 Sq Ft
    • Built 2002

    Last Sold Summary

    • 3% Below List Price
    • $277/SF
    • 27 Days On Market

    Current Estimated Value $786,158

    Last Listing Agent Jacob Katz MS Realty Group USA, Inc

    1071 Craigville Rd, Chester, NY 10918
  • 10 Tulip Ln, Monroe, NY 10950

    $525,000

    Sold Sep 02, 2025

    10 Tulip Ln, Monroe, NY 10950

    • 4 Beds
    • 2 Baths
    • 1,758 Sq Ft
    • Built 1961

    Last Sold Summary

    • 3% Below List Price
    • $299/SF
    • 38 Days On Market

    Current Estimated Value $534,227

    Last Listing Agent Philip Szumlaski Keller Williams Realty

    10 Tulip Ln, Monroe, NY 10950
  • 31 Hudson St, Chester, NY 10918

    $445,000

    Sold May 21, 2026

    31 Hudson St, Chester, NY 10918

    • 2 Beds
    • 2 Baths
    • 1,998 Sq Ft
    • Built 1947

    Last Sold Summary

    • 1% Below List Price
    • $223/SF
    • 32 Days On Market

    Current Estimated Value $452,189

    Last Listing Agent Geoffrey Green BHG Real Estate Green Team

    31 Hudson St, Chester, NY 10918
  • 3 Derose Ln, Chester, NY 10918

    $655,000

    Sold Feb 18, 2026

    3 Derose Ln, Chester, NY 10918

    • 5 Beds
    • 3.5 Baths
    • 2,550 Sq Ft
    • Built 1997

    Last Sold Summary

    • 1% Above List Price
    • $257/SF
    • 44 Days On Market

    Current Estimated Value $663,645

    Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

    3 Derose Ln, Chester, NY 10918
  • 71 Greycourt Rd, Chester, NY 10918

    $437,000

    Sold Jun 14, 2026

    71 Greycourt Rd, Chester, NY 10918

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft
    • Built 1957

    Last Sold Summary

    • 10% Above List Price
    • $414/SF
    • 159 Days On Market

    Current Estimated Value $437,924

    Last Listing Agent Lazar Schvimmer Blooming Realty

    71 Greycourt Rd, Chester, NY 10918
  • 2323 Whispering Hills Unit 213, Chester, NY 10918

    $340,000

    Sold Jul 08, 2026

    2323 Whispering Hills Unit 213, Chester, NY 10918

    • 2 Beds
    • 2 Baths
    • 1,316 Sq Ft
    • Built 1984

    Last Sold Summary

    • 4% Above List Price
    • $258/SF
    • 14 Days On Market

    Current Estimated Value $324,839

    Last Listing Agent Luanne McGann Century 21 Full Service Realty

    2323 Whispering Hills Unit 213, Chester, NY 10918
  • /13

    $300,000

    Sold Dec 23, 2025

    68 Walter Foote Rd, Chester, NY 12853

    • Land
    • 194 Acres
    • $1,546 per Acre

    Last Sold Summary

    • 52% Below List Price
    • 86 Days On Market

    Last Listing Agent Cindy Brower Coldwell Banker Prime Properties

    68 Walter Foote Rd, Chester, NY 12853
  • 82 Southside Dr, Monroe, NY 10950

    $485,000

    Sold Jul 23, 2026

    82 Southside Dr, Monroe, NY 10950

    • 4 Beds
    • 2 Baths
    • 1,642 Sq Ft
    • Built 1950

    Last Sold Summary

    • 8% Above List Price
    • $295/SF
    • 28 Days On Market

    Current Estimated Value $451,177

    Last Listing Agent Ammar Iqbal eXp Realty

    82 Southside Dr, Monroe, NY 10950
  • 0 William Hill Rd, Chester, NY 12817

    $125,000

    Sold Oct 03, 2025

    0 William Hill Rd, Chester, NY 12817

    • Land
    • 45.83 Acres
    • $2,727 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 99 Days On Market

    Last Listing Agent Jason Minch William Raveis-New York LLC

    0 William Hill Rd, Chester, NY 12817
  • 38 Jefferson Dr, Monroe, NY 10950

    $554,000

    Sold Jul 31, 2026

    38 Jefferson Dr, Monroe, NY 10950

    • 3 Beds
    • 1.5 Baths
    • 1,644 Sq Ft
    • Built 1976

    Last Sold Summary

    • 1% Above List Price
    • $337/SF
    • 39 Days On Market

    Current Estimated Value $544,978

    Last Listing Agent Lance Gibbs Arrowhead Realty

    38 Jefferson Dr, Monroe, NY 10950
  • 219 Bull Mill Rd, Chester, NY 10918

    $535,000

    Sold Feb 09, 2026

    219 Bull Mill Rd, Chester, NY 10918

    • 4 Beds
    • 2 Baths
    • 1,928 Sq Ft
    • Built 1960

    Last Sold Summary

    • 2% Above List Price
    • $277/SF
    • 36 Days On Market

    Current Estimated Value $541,158

    Last Listing Agent Claudia Lepore Keller Williams Realty

    219 Bull Mill Rd, Chester, NY 10918
  • 223 Eagleton Dr, Monroe, NY 10950

    $415,000

    Sold Jul 09, 2026

    223 Eagleton Dr, Monroe, NY 10950

    • 3 Beds
    • 2.5 Baths
    • 1,694 Sq Ft
    • Built 1997

    Last Sold Summary

    • 5% Above List Price
    • $245/SF
    • 25 Days On Market

    Current Estimated Value $395,291

    Last Listing Agent Theresa Powers Keller Williams Realty

    223 Eagleton Dr, Monroe, NY 10950
  • 354 Rande Rd Unit 354, Monroe, NY 10950

    $419,999

    Sold Jan 07, 2026

    354 Rande Rd Unit 354, Monroe, NY 10950

    • 3 Beds
    • 2.5 Baths
    • 1,698 Sq Ft
    • Built 1999

    Last Sold Summary

    • $247/SF
    • 28 Days On Market

    Current Estimated Value $423,509

    Last Listing Agent Joel Ayala HomeSmart Homes & Estates

    354 Rande Rd Unit 354, Monroe, NY 10950
  • 507 Bull Mill Rd, Chester, NY 10918

    $675,000

    Sold Feb 18, 2026

    507 Bull Mill Rd, Chester, NY 10918

    • 5 Beds
    • 2.5 Baths
    • 3,115 Sq Ft
    • Built 2003

    Last Sold Summary

    • 4% Below List Price
    • $217/SF
    • 134 Days On Market

    Current Estimated Value $750,250

    Last Listing Agent Alison Orlando KW Hudson Valley United

    507 Bull Mill Rd, Chester, NY 10918
  • /20

    $155,000

    Sold Apr 01, 2026

    L2 Friends Lake Rd, Chester, NY 12817

    • Land
    • 22.6 Acres
    • $6,858 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 607 Days On Market

    Last Listing Agent Walter Swartz Gallo Realty ADK Inc

    L2 Friends Lake Rd, Chester, NY 12817

Showing Results 1 - 40, Page 1 of 4

Frequently Asked Questions

What is the average home price in Chester, NY?
Homes for sale in Chester, NY have an average home price of $623,023.
What is the average time to sell a house in Chester, NY?
The houses for sale in Chester, NY spend an average of 64 days on the market.
What is the number of active homes for sale in Chester, NY?
There are 65 active homes for sale in Chester, NY.
How many homes have sold over the last 12 months in Chester, NY?
84 homes have sold in Chester, NY over the last 12 months.

Home Price Trends

Median Sale Price
$498,500
Median Single Family Sale Price
$660,000
Median Townhouse Sale Price
$340,000
Median 2 Bedroom Sale Price
$310,000
Median 1 Bedroom Sale Price
$370,000
Average Price Per Sq Ft
$273
Number of Homes for Sale
65
Last 12 months Home Sales
84
Months of Supply
9.30
Median List Price
$582,499
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-5%
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