Chester, NY Homes

• 

  $365,000 Sold Nov 14, 2025

  2409 Whispering Hills, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Built 1987

  Last Sold Summary

  • 2% Above List Price
  • $274/SF
  • 26 Days On Market

  Last Listing Agent Linda Clark Hudson Valley Griffith

  2409 Whispering Hills, Chester, NY 10918
• 

  Est $602,797 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,680 Sq Ft

  73 Hambletonian Rd, Chester, NY 10918

  73 Hambletonian Rd, Chester, NY 10918
• 

  $355,000 Sold Mar 22, 2025

  2910 Whispering Hills, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Below List Price
  • $267/SF
  • 48 Days On Market

  Current Estimated Value $372,897

  Last Listing Agent Nancy Gloss-Nolan eRealty Advisors, Inc

  2910 Whispering Hills, Chester, NY 10918
• 

  Est $797,449 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,396 Sq Ft

  15 Banker Dr, Chester, NY 10918

  15 Banker Dr, Chester, NY 10918
• 

  $460,000 Sold Aug 28, 2025

  22 Able Noble Dr, Chester, NY 10918

  • 4 Beds
  • 2 Baths
  • 1,770 Sq Ft
  • Built 1968

  Last Sold Summary

  • 8% Below List Price
  • $260/SF
  • 40 Days On Market

  Current Estimated Value $475,391

  Last Listing Agent Robin Kelly Picture It Sold, LLC

  22 Able Noble Dr, Chester, NY 10918
• 

  Est $1,372,063 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 5,007 Sq Ft

  10 Silvertail Rd, Chester, NY 10918

  10 Silvertail Rd, Chester, NY 10918
• 

  $740,000 Sold Nov 21, 2025

  48 Brennan Ct, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,063 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Below List Price
  • $242/SF
  • 29 Days On Market

  Last Listing Agent Claude Brischoux Keller Williams Realty

  48 Brennan Ct, Chester, NY 10918
• 

  Est $843,922 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,656 Sq Ft

  49 Stone Mountain Trail, Chester, NY 10918

  49 Stone Mountain Trail, Chester, NY 10918
• 

  $624,000 Sold Jun 23, 2025

  20 Hubshop Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,236 Sq Ft
  • Built 1999

  Last Sold Summary

  • 4% Below List Price
  • $279/SF
  • 66 Days On Market

  Current Estimated Value $636,075

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  20 Hubshop Rd, Chester, NY 10918
• 

  Est $826,836 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,499 Sq Ft

  11 Stone Mountain Trail, Chester, NY 10918

  11 Stone Mountain Trail, Chester, NY 10918
• 

  $780,000 Sold Jan 23, 2025

  504 Bull Mill Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,777 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Above List Price
  • $281/SF
  • 56 Days On Market

  Current Estimated Value $788,929

  Last Listing Agent Joseph Rosenfeld Flag Realty Group

  504 Bull Mill Rd, Chester, NY 10918
• 

  Est $1,120,398 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,114 Sq Ft

  40 Deer Trail Rd, Chester, NY 10918

  40 Deer Trail Rd, Chester, NY 10918
• 

  $330,000 Sold Aug 15, 2025

  4503 Whispering Hills, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $248/SF
  • 142 Days On Market

  Current Estimated Value $341,960

  Last Listing Agent Richard Baxter Keller Williams Realty

  4503 Whispering Hills, Chester, NY 10918
• 

  Est $506,184 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 1,815 Sq Ft

  208 Glenmere Rd, Chester, NY 10918

  208 Glenmere Rd, Chester, NY 10918
• 

  $551,225 Sold Jun 17, 2025

  152 Lake Region Blvd, Monroe, NY 10950

  • 4 Beds
  • 2.5 Baths
  • 1,916 Sq Ft
  • Built 1984

  Last Sold Summary

  • $288/SF
  • 38 Days On Market

  Current Estimated Value $557,027

  Last Listing Agent Raynilson Vasquez eXp Realty

  152 Lake Region Blvd, Monroe, NY 10950
• 

  Est $487,598 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,530 Sq Ft

  226 Glenmere Rd, Chester, NY 10918

  226 Glenmere Rd, Chester, NY 10918
• 

  $1,450,000 Sold May 02, 2025

  151 Kings Highway Bypass, Chester, NY 10918

  • 4 Beds
  • 5 Baths
  • 5,638 Sq Ft
  • Built 2022

  Last Sold Summary

  • 9% Below List Price
  • $257/SF
  • 327 Days On Market

  Last Listing Agent John Olivero Keller Williams Realty

  151 Kings Highway Bypass, Chester, NY 10918
• 

  Est $398,880 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 920 Sq Ft

  464 Pine Hill Rd, Chester, NY 10918

  464 Pine Hill Rd, Chester, NY 10918
• 

  $715,000 Sold Apr 01, 2025

  76 Restdale Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,838 Sq Ft
  • Built 1997

  Last Sold Summary

  • 2% Above List Price
  • $252/SF
  • 20 Days On Market

  Current Estimated Value $751,560

  Last Listing Agent Philip Szumlaski Keller Williams Realty

  76 Restdale Rd, Chester, NY 10918
• 

  Est $471,069 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,311 Sq Ft

  520 Pine Hill Rd, Chester, NY 10918

  520 Pine Hill Rd, Chester, NY 10918
• 

  $460,000 Sold Jun 18, 2025

  55 Hudson St, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,576 Sq Ft
  • Built 1956

  Last Sold Summary

  • 7% Above List Price
  • $292/SF
  • 20 Days On Market

  Current Estimated Value $472,793

  Last Listing Agent Lynelle Alessi Keller Williams Hudson Valley

  55 Hudson St, Chester, NY 10918
• 

  Est $830,982 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 4,004 Sq Ft

  86 Beverly Rd, Chester, NY 10918

  86 Beverly Rd, Chester, NY 10918
• 

  $375,000 Sold Dec 11, 2025

  4309 Whispering Hills Dr, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,355 Sq Ft
  • Built 1989

  Last Sold Summary

  • $277/SF
  • 27 Days On Market

  Last Listing Agent Sean Israelski Howard Hanna Rand Realty

  4309 Whispering Hills Dr, Chester, NY 10918
• 

  Est $682,987 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,511 Sq Ft

  27 Beverly Rd, Chester, NY 10918

  27 Beverly Rd, Chester, NY 10918
• 

  $350,000 Sold Apr 07, 2025

  3815 Whispering Hills Dr, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Built 1987

  Last Sold Summary

  • 9% Above List Price
  • $263/SF
  • 23 Days On Market

  Current Estimated Value $371,797

  Last Listing Agent Frank Golio Howard Hanna Rand Realty

  3815 Whispering Hills Dr, Chester, NY 10918
• 

  Est $706,334 Not Listed For Sale

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

  38 Beverly Rd, Chester, NY 10918

  38 Beverly Rd, Chester, NY 10918
• 

  $700,000 Sold May 23, 2025

  8 Country Woods Dr, Chester, NY 10918

  • 5 Beds
  • 2.5 Baths
  • 3,120 Sq Ft
  • Built 2002

  Last Sold Summary

  • $224/SF
  • 49 Days On Market

  Current Estimated Value $720,644

  Last Listing Agent Sheyla Falesto Howard Hanna Rand Realty

  8 Country Woods Dr, Chester, NY 10918
• 

  Est $798,907 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,907 Sq Ft

  55 Brookview Dr, Monroe, NY 10950

  55 Brookview Dr, Monroe, NY 10950
• 

  $560,000 Sold May 02, 2025

  69 High St, Chester, NY 10918

  • 3 Beds
  • 3 Baths
  • 2,092 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Above List Price
  • $268/SF
  • 43 Days On Market

  Current Estimated Value $573,563

  Last Listing Agent Sandra Arnez Keller Williams Hudson Valley

  69 High St, Chester, NY 10918
• 

  Est $1,084,113 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 4,198 Sq Ft

  11 Sunfish Ln, Monroe, NY 10950

  11 Sunfish Ln, Monroe, NY 10950
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  $255,000 Sold Mar 03, 2025

  78 Panther Mtn Rd, Chester, NY 12817

  • 3 Beds
  • 1 Bath
  • 876 Sq Ft
  • Built 1961

  Last Sold Summary

  • 7% Below List Price
  • $291/SF
  • 68 Days On Market

  Last Listing Agent Angie Mead Gallo Realty ADK Inc

  78 Panther Mtn Rd, Chester, NY 12817
• 

  Est $514,818 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,521 Sq Ft

  951 Lakes Rd, Monroe, NY 10950

  951 Lakes Rd, Monroe, NY 10950
• 

  

  /11

  $29,000 Sold Nov 03, 2025

  L27 Carriage Knolls Rd, Chester, NY 12817

  • Land
  • 1.8 Acres
  • $16,111 per Acre

  Last Sold Summary

  • 71% Below List Price
  • 20 Days On Market

  Last Listing Agent Walter Swartz Gallo Realty ADK Inc

  L27 Carriage Knolls Rd, Chester, NY 12817
• 

  Est $766,651 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,347 Sq Ft

  8 Reputation Dr, Chester, NY 10918

  8 Reputation Dr, Chester, NY 10918
• 

  $382,000 Sold Sep 29, 2025

  3915 Whispering Hills, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Built 1987

  Last Sold Summary

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

  Last Listing Agent Kristie Jacques Century 21 Full Service Realty

  3915 Whispering Hills, Chester, NY 10918
• 

  Est $510,003 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,296 Sq Ft

  41 Sugarloaf Mountain Rd, Chester, NY 10918

  41 Sugarloaf Mountain Rd, Chester, NY 10918
• 

  $305,000 Sold Aug 22, 2025

  4501 Whispering Hills Dr, Chester, NY 10918

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

  Last Sold Summary

  • 9% Above List Price
  • $281/SF
  • 27 Days On Market

  Last Listing Agent Bernadette Giordano Howard Hanna Rand Realty

  4501 Whispering Hills Dr, Chester, NY 10918
• 

  Est $549,937 Not Listed For Sale

  • 6 Beds
  • 2 Baths
  • 3,662 Sq Ft

  18 Sugarloaf Mountain Rd, Chester, NY 10918

  18 Sugarloaf Mountain Rd, Chester, NY 10918
• 

  

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  $210,000 Sold Jun 09, 2025

  7823 State Route 9, Chester, NY 12860

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • Built 1995

  Last Sold Summary

  • 18% Below List Price
  • $162/SF
  • 165 Days On Market

  Current Estimated Value $215,589

  Last Listing Agent Vickie Reed Hunt ERA

  7823 State Route 9, Chester, NY 12860
• 

  Est $584,705 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,232 Sq Ft

  104 Trout Brook Rd, Monroe, NY 10950

  104 Trout Brook Rd, Monroe, NY 10950

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