143

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 $1,278,785

    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 $627,942

    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 $312,730

    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 $277,956

    Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

    2104 Whispering Hills, Chester, NY 10918
  • 189 Creamery Pond Rd, Chester, NY 10918

    $735,000

    Sold Jul 21, 2025

    189 Creamery Pond Rd, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,980 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Above List Price
    • $247/SF
    • 19 Days On Market

    Current Estimated Value $732,824

    Last Listing Agent Patricia Brady Keller Williams Realty

    189 Creamery Pond Rd, Chester, NY 10918
  • 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 $293,327

    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 $348,670

    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 $638,624

    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 $314,539

    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 $370,987

    Last Listing Agent Erin Connolly-Frontino Artisan Realty

    4703 Whispering Hills Dr, Chester, NY 10918
  • 242 Meadow Ave, Chester, NY 10918

    $225,000

    Sold Jun 30, 2025

    242 Meadow Ave, Chester, NY 10918

    • 4 Beds
    • 3 Baths
    • 2,519 Sq Ft
    • Built 1930

    Last Sold Summary

    • $89/SF
    • 56 Days On Market

    Current Estimated Value $348,000

    Last Listing Agent Kathleen Strong Hudson Valley Griffith

    242 Meadow Ave, 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 $653,625

    Last Listing Agent Aoife Freeman eXp Realty

    12 Bianca Blvd, Chester, NY 10918
  • 100 Marian Ct, Warwick, NY 10990

    $411,000

    Sold Jul 08, 2025

    100 Marian Ct, Warwick, NY 10990

    • 3 Beds
    • 2.5 Baths
    • 1,528 Sq Ft
    • Built 1986

    Last Sold Summary

    • 4% Above List Price
    • $269/SF
    • 26 Days On Market

    Current Estimated Value $431,265

    Last Listing Agent Jennifer DiCostanzo RE/MAX Town & Country

    100 Marian Ct, Warwick, NY 10990
  • /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
  • 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 $301,889

    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 $627,056

    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 $311,601

    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 $675,208

    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 $797,760

    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 $406,534

    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 $843,057

    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 $551,038

    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 $615,951

    Last Listing Agent Dana Posner Howard Hanna Rand Realty

    411 Prospect Rd, Chester, NY 10918
  • 11 Vista Dr, Chester, NY 10918

    $525,000

    Sold Jul 24, 2025

    11 Vista Dr, Chester, NY 10918

    • 4 Beds
    • 3 Baths
    • 2,122 Sq Ft
    • Built 1998

    Last Sold Summary

    • 2% Above List Price
    • $247/SF
    • 43 Days On Market

    Current Estimated Value $554,168

    Last Listing Agent James Feldhaus eXp Realty

    11 Vista Dr, 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 $379,439

    Last Listing Agent Lorrainne Pisciotta Weichert Realtors

    226 Eagleton Dr, Monroe, NY 10950
  • 26 W Meadow Way, Chester, NY 10918

    $869,000

    Sold Jul 24, 2025

    26 W Meadow Way, Chester, NY 10918

    • 4 Beds
    • 3 Baths
    • 3,100 Sq Ft
    • Built 2024

    Last Sold Summary

    • 3% Below List Price
    • $280/SF
    • 85 Days On Market

    Current Estimated Value $119,000

    Last Listing Agent Nancy Sardo BHG Real Estate Green Team

    26 W Meadow Way, Chester, NY 10918
  • 0 Renies Rd, Chester, NY 10918

    $100,000

    Sold Feb 12, 2026

    0 Renies Rd, Chester, NY 10918

    • Land
    • 1.85 Acres
    • $54,054 per Acre

    Last Sold Summary

    • 50% Below List Price
    • 102 Days On Market

    Last Listing Agent Kristie Jacques Century 21 Full Service Realty

    0 Renies 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 $525,074

    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 $447,795

    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 $659,129

    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 $485,957

    Last Listing Agent Lazar Schvimmer Blooming Realty

    71 Greycourt Rd, 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
  • 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
  • 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 $537,971

    Last Listing Agent Claudia Lepore Keller Williams Realty

    219 Bull Mill Rd, Chester, NY 10918
  • 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 $415,378

    Last Listing Agent Joel Ayala HomeSmart Homes & Estates

    354 Rande Rd Unit 354, Monroe, NY 10950
  • 19 Taurus Ave, Monroe, NY 10950

    $389,000

    Sold Jul 09, 2025

    19 Taurus Ave, Monroe, NY 10950

    • 3 Beds
    • 1.5 Baths
    • 1,288 Sq Ft
    • Built 1954

    Last Sold Summary

    • 4% Above List Price
    • $302/SF
    • 30 Days On Market

    Current Estimated Value $386,145

    Last Listing Agent Christian Baez KW Hudson Valley Untied

    19 Taurus Ave, 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 $698,087

    Last Listing Agent Alison Orlando KW Hudson Valley Untied

    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
  • 10 Spectrum Dr, Chester, NY 10918

    $800,000

    Sold Sep 15, 2025

    10 Spectrum Dr, Chester, NY 10918

    • 5 Beds
    • 4 Baths
    • 4,496 Sq Ft
    • Built 1991

    Last Sold Summary

    • 11% Below List Price
    • $178/SF
    • 24 Days On Market

    Current Estimated Value $833,089

    Last Listing Agent David Hopstein eRealty Advisors, Inc

    10 Spectrum Dr, Chester, NY 10918

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 $644,395.
What is the average time to sell a house in Chester, NY?
The houses for sale in Chester, NY spend an average of 59 days on the market.
What is the number of active homes for sale in Chester, NY?
There are 53 active homes for sale in Chester, NY.
How many homes have sold over the last 12 months in Chester, NY?
87 homes have sold in Chester, NY over the last 12 months.

Home Prices in Chester, NY

Home Price Trends

Median Sale Price
$498,000
Median Single Family Sale Price
$655,000
Median Townhouse Sale Price
$324,950
Median 2 Bedroom Sale Price
$310,000
Average Price Per Sq Ft
$274
Number of Homes for Sale
53
Last 12 months Home Sales
87
Months of Supply
7.30
Median List Price
$585,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-5%
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