6,841

Chester, NY Homes

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  • 37 Surrey Rd, Chester, NY 10918
    37 Surrey Rd, Chester, NY 10918
    37 Surrey Rd, Chester, NY 10918
    /40

    $500,000

    • 4 Beds
    • 2 Baths
    • 1,730 Sq Ft

    37 Surrey Rd, Chester, NY 10918

    Looking for a 4-bed home in Chester, NY with a pool, major system updates, generous outdoor living space, and convenient access to schools, parks, shopping, and commuter routes? Welcome to 37 Surrey Road, a beautifully maintained raised ranch offering 4 bedrooms, 2 full bathrooms, approximately 1,730 square feet of living space, and a backyard designed for entertaining and relaxation. Set on a

    Lady Castro eXp Realty

    37 Surrey Rd, Chester, NY 10918
  • 42 Heaton Rd, Monroe, NY 10950

    $222,000

    Sold Nov 21, 2025

    42 Heaton Rd, Monroe, NY 10950

    • 2 Beds
    • 1 Bath
    • 484 Sq Ft
    • Built 1950

    Last Sold Summary

    • 1% Below List Price
    • $459/SF
    • 63 Days On Market

    Current Estimated Value $234,172

    Last Listing Agent Maureen Schroder Keller Williams Valley Realty

    42 Heaton Rd, Monroe, NY 10950
  • 35 Maple Ave, Chester, NY 10918
    35 Maple Ave, Chester, NY 10918
    35 Maple Ave, Chester, NY 10918
    /29

    $499,900

    $50K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,032 Sq Ft

    35 Maple Ave, Chester, NY 10918

    Welcome to 35 Maple Avenue, a bright 3 bedroom, 3 full bath Raised Ranch in the desirable Village of Chester ideally located near the Village Park & School. This spacious 2,032 sq. ft. residence built in 2002 & Updated in 2020 including bathrooms & New Kitchen in 2024. The open main level features a White EIK with Quartz Counters & Island, stylish white tile backsplash, Pantry, Black Appliances,

    Joanne Timperio RE/MAX Benchmark Realty Group

    35 Maple Ave, Chester, NY 10918
  • 81 Hambletonian Rd, Chester, NY 10918

    $612,500

    Sold Sep 05, 2025

    81 Hambletonian Rd, Chester, NY 10918

    • 3 Beds
    • 2 Baths
    • 1,938 Sq Ft
    • Built 2002

    Last Sold Summary

    • 2% Below List Price
    • $316/SF
    • 23 Days On Market

    Current Estimated Value $649,090

    Last Listing Agent Dean Diltz Keller Williams Realty

    81 Hambletonian Rd, Chester, NY 10918
    • 62 Lincoln Rd, Monroe, NY 10950

      Est $490,287

      Not Listed For Sale

      62 Lincoln Rd, Monroe, NY 10950

      • 4 Beds
      • 2 Baths
      • 1,523 Sq Ft
      • Built 1974
      62 Lincoln Rd, Monroe, NY 10950

      Last Sold Summary

      • 14 Days On Market

  • 2 Primrose Ln, Chester, NY 10918
    2 Primrose Ln, Chester, NY 10918
    2 Primrose Ln, Chester, NY 10918
    /42

    $849,900

    • 4 Beds
    • 3 Baths
    • 2,370 Sq Ft

    2 Primrose Ln, Chester, NY 10918

    Welcome to this stunning Colonial, perfectly blending comfort, style, and functionality. Offering 2,370 sq ft plus full walkout basement, this beautifully designed home features 4 spacious bedrooms and 3 full bathrooms, creating an inviting layout ideal for everyday living and entertaining.Step inside to a grand, sun-filled foyer with soaring ceilings that set the tone for the home’s warm and

    Janet Rendle Weichert Realtors

    2 Primrose Ln, Chester, NY 10918
  • 24 Oak Dr, Monroe, NY 10950

    $480,000

    Sold Jan 26, 2026

    24 Oak Dr, Monroe, NY 10950

    • 3 Beds
    • 2 Baths
    • 1,662 Sq Ft
    • Built 1965

    Last Sold Summary

    • 2% Above List Price
    • $289/SF
    • 35 Days On Market

    Current Estimated Value $484,775

    Last Listing Agent Jay Himelson Howard Hanna Rand Realty

    24 Oak Dr, Monroe, NY 10950
    • 59 Wilson Rd, Monroe, NY 10950

      Est $559,337

      Not Listed For Sale

      59 Wilson Rd, Monroe, NY 10950

      • 4 Beds
      • 2 Baths
      • 2,134 Sq Ft
      • Built 1977
      59 Wilson Rd, Monroe, NY 10950

      Last Sold Summary

      • 23 Days On Market

  • 12 Damian Ct, Chester, NY 10918
    12 Damian Ct, Chester, NY 10918
    12 Damian Ct, Chester, NY 10918
    /34

    $949,000

    $50K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,136 Sq Ft

    12 Damian Ct, Chester, NY 10918

    Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second

    Elimelech Kremer MS Realty Group USA, Inc

    12 Damian Ct, Chester, NY 10918
  • 358 Bull Mill Rd, Chester, NY 10918

    $499,000

    Sold Oct 23, 2025

    358 Bull Mill Rd, Chester, NY 10918

    • 5 Beds
    • 2.5 Baths
    • 3,120 Sq Ft
    • Built 1840

    Last Sold Summary

    • $160/SF
    • 40 Days On Market

    Current Estimated Value $549,306

    Last Listing Agent Amy Wilhelm Corcoran Baer & McIntosh

    358 Bull Mill Rd, Chester, NY 10918
    • 9 Grant Dr, Monroe, NY 10950

      Est $543,762

      Not Listed For Sale

      9 Grant Dr, Monroe, NY 10950

      • 4 Beds
      • 2 Baths
      • 1,644 Sq Ft
      • Built 1987
      9 Grant Dr, Monroe, NY 10950

      Last Sold Summary

      • 23 Days On Market

  • 3-4 Adirondack Heights Rd, Chester, NY 12817
    3-4 Adirondack Heights Rd, Chester, NY 12817
    3-4 Adirondack Heights Rd, Chester, NY 12817
    /33

    $89,500

    • Land
    • 12.79 Acres
    • $6,998 per Acre

    3-4 Adirondack Heights Rd, Chester, NY 12817

    Seller financing now available. 12.79 acres of mixed forest and wetlands. Perc tests and engineered plot plans have been completed. APA approved building sites with well & septic locations identified. (2-lots can each be built upon or just have one large lot) Power at the road pedestal box. Tons of hemlock, spruce, and pine trees throughout. Close to Chestertown, 20-minutes to Gore Mountain or

    Walter Swartz Gallo Realty ADK Inc

    3-4 Adirondack Heights Rd, Chester, NY 12817
  • 307 Gibson Hill Rd, Chester, NY 10918

    $315,000

    Sold May 29, 2026

    307 Gibson Hill Rd, Chester, NY 10918

    • 2 Beds
    • 1 Bath
    • 1,272 Sq Ft
    • Built 1920

    Last Sold Summary

    • 10% Below List Price
    • $248/SF
    • 36 Days On Market

    Current Estimated Value $350,687

    Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

    307 Gibson Hill Rd, Chester, NY 10918
    • 3 Grant Dr, Monroe, NY 10950

      Est $550,195

      Not Listed For Sale

      3 Grant Dr, Monroe, NY 10950

      • 3 Beds
      • 2 Baths
      • 1,932 Sq Ft
      • Built 1989
      3 Grant Dr, Monroe, NY 10950

      Last Sold Summary

      • 21 Days On Market

  • 1.1 Cobble Creek Rd Unit 1, Chester, NY 12853
    1.1 Cobble Creek Rd Unit 1, Chester, NY 12853
    1.1 Cobble Creek Rd Unit 1, Chester, NY 12853
    /13

    $89,995

    • Land
    • 25.03 Acres
    • $3,595 per Acre

    1.1 Cobble Creek Rd Unit 1, Chester, NY 12853

    Adirondack Mountain Retreat with Stream and Trails Discover 25 acres of classic Adirondack wilderness in Chester, New York, tucked along a year-round, town-maintained road. This exceptional property rises gently from the roadside to several attractive, APA-approved building locations, offering excellent opportunities for an off-grid cabin, or vacation retreat. The land is heavily wooded with a

    Marc Christmas CHRISTMAS AND ASSOCIATES INC

    1.1 Cobble Creek Rd Unit 1, Chester, NY 12853
  • 34 Booth Rd, Chester, NY 10918

    $660,000

    Sold Jun 01, 2026

    34 Booth Rd, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,506 Sq Ft
    • Built 1998

    Last Sold Summary

    • 8% Below List Price
    • $263/SF
    • 41 Days On Market

    Current Estimated Value $853,033

    Last Listing Agent Kristie Jacques Century 21 Full Service Realty

    34 Booth Rd, Chester, NY 10918
    • 1 Grant Dr, Monroe, NY 10950

      Est $507,661

      Not Listed For Sale

      1 Grant Dr, Monroe, NY 10950

      • 4 Beds
      • 2 Baths
      • 1,644 Sq Ft
      • Built 1989
      1 Grant Dr, Monroe, NY 10950

      Last Sold Summary

      • 54 Days On Market

  • 19 Bull Mine Rd, Chester, NY 10918
    19 Bull Mine Rd, Chester, NY 10918
    19 Bull Mine Rd, Chester, NY 10918
    /43

    $949,000

    • 4 Beds
    • 2.5 Baths
    • 3,332 Sq Ft

    19 Bull Mine Rd, Chester, NY 10918

    Set on 2.3 acres in Chester, this impressive property offers space, versatility, and scenic surroundings. The residence features approximately 3,332 square feet of living space with 4 bedrooms, 2 full baths and 1 half bath, thoughtfully designed for comfortable everyday living and entertaining. Interior highlights include generously sized living areas, a fireplace, abundant natural light, and

    James Cosenza BHG Real Estate Green Team

    19 Bull Mine Rd, Chester, NY 10918
  • 8 Hom St, Chester, NY 10918

    $425,000

    Sold Oct 16, 2025

    8 Hom St, Chester, NY 10918

    • 3 Beds
    • 1.5 Baths
    • 1,410 Sq Ft
    • Built 1962

    Last Sold Summary

    • 11% Below List Price
    • $301/SF
    • 74 Days On Market

    Current Estimated Value $429,636

    Last Listing Agent Joao Rodrigues Preferred Properties Real Esta

    8 Hom St, Chester, NY 10918
    • 9 Adams Ct, Monroe, NY 10950

      Est $580,091

      Not Listed For Sale

      9 Adams Ct, Monroe, NY 10950

      • 3 Beds
      • 2 Baths
      • 2,298 Sq Ft
      • Built 1973
      9 Adams Ct, Monroe, NY 10950

      Last Sold Summary

      • 21 Days On Market

  • 101 Whitetail Run, Chester, NY 10918
    101 Whitetail Run, Chester, NY 10918
    101 Whitetail Run, Chester, NY 10918
    /35

    $589,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,854 Sq Ft

    101 Whitetail Run, Chester, NY 10918

    Looking for privacy, yet close to highways, shopping and transit. Look no further. Welcome to your new home on 3 private parklike acres. Spotless, lovingly maintained home featuring spacious open floor plan. Main level offering hardwood floors, large living room with cathedral ceilings, gas fireplace, built ins, eat in kitchen with quartz counters, stainless steel appliances and a formal dining

    Aylin Ippolito Cronin & Company Real Estate

    101 Whitetail Run, Chester, NY 10918
  • 4 Wood Rd, Chester, NY 10918

    $475,000

    Sold Sep 08, 2025

    4 Wood Rd, Chester, NY 10918

    • 4 Beds
    • 1.5 Baths
    • 1,554 Sq Ft
    • Built 1960

    Last Sold Summary

    • $306/SF
    • 73 Days On Market

    Current Estimated Value $472,039

    Last Listing Agent Matthew Skowronski HomeSmart Homes & Estates

    4 Wood Rd, Chester, NY 10918
  • 10 Well Sweep Ln, Chester, NY 10918
    10 Well Sweep Ln, Chester, NY 10918
    10 Well Sweep Ln, Chester, NY 10918
    /8

    $869,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    10 Well Sweep Ln, Chester, NY 10918

    Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combination of municipal water and sewer, thoughtfully designed floor plans, and stunning lots in a highly desirable location in the Warwick school district. Homes will start at $780,000, with multiple design options available to suit a variety of lifestyles. Lots 1 and 2 will feature custom Bilonial designs with

    Carla Terranova Keller Williams Realty

    10 Well Sweep Ln, Chester, NY 10918
  • 7 Cambridge Cir, Monroe, NY 10950

    $585,000

    Sold Aug 27, 2025

    7 Cambridge Cir, Monroe, NY 10950

    • 4 Beds
    • 2.5 Baths
    • 2,516 Sq Ft
    • Built 1992

    Last Sold Summary

    • $233/SF
    • 57 Days On Market

    Current Estimated Value $607,657

    Last Listing Agent Alissa Taylor-Vetell Keller Williams Realty

    7 Cambridge Cir, Monroe, NY 10950
  • 4116 Whispering Hills, Chester, NY 10918
    4116 Whispering Hills, Chester, NY 10918
    4116 Whispering Hills, Chester, NY 10918
    /25

    $375,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,355 Sq Ft

    4116 Whispering Hills, Chester, NY 10918

    Beautifully updated 3-bedroom, 2.5-bath Dogwood model townhouse located in Whispering Hills, a desirable corner unit setting. This home offers a perfect blend of comfort and modern upgrades.Step inside to find a thoughtfully refreshed interior with remodeled and freshly painted bathrooms, along with a bright, open layout. The kitchen is equipped with a brand-new refrigerator and dishwasher,

    Michael Casarella William Raveis-New York, LLC

    4116 Whispering Hills, Chester, NY 10918
  • 85 Surrey Rd, Chester, NY 10918
    85 Surrey Rd, Chester, NY 10918
    85 Surrey Rd, Chester, NY 10918
    /35

    $524,900

    Pending
    • 4 Beds
    • 2 Baths
    • 2,076 Sq Ft

    85 Surrey Rd, Chester, NY 10918

    Welcome to 85 Surrey Road in Chester, NY, a beautifully updated home that blends modern upgrades with timeless comfort in the heart of the Hudson Valley. This move-in-ready property offers everything today’s buyers are searching for—energy efficiency, stylish finishes, and exceptional indoor-outdoor living.Step inside to discover a fabulously updated kitchen, designed for both everyday living

    Rebecca Matta-Candela Keller Williams Realty

    85 Surrey Rd, Chester, NY 10918
  • 25 High St, Chester, NY 10918

    $505,000

    Sold Feb 26, 2026

    25 High St, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,898 Sq Ft
    • Built 1850

    Last Sold Summary

    • 4% Below List Price
    • $174/SF
    • 192 Days On Market

    Current Estimated Value $527,580

    Last Listing Agent Alicia Goldman Christie's Int. Real Estate

    25 High St, Chester, NY 10918
    • 2 Tyler Place, Monroe, NY 10950

      Est $565,470

      Not Listed For Sale

      2 Tyler Place, Monroe, NY 10950

      • 4 Beds
      • 2 Baths
      • 1,944 Sq Ft
      • Built 1973
      2 Tyler Place, Monroe, NY 10950

      Last Sold Summary

      • 36 Days On Market

  • 332 Heritage Ln, Monroe, NY 10950
    332 Heritage Ln, Monroe, NY 10950
    332 Heritage Ln, Monroe, NY 10950
    /36

    $419,000

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

    332 Heritage Ln, Monroe, NY 10950

    Spacious and well-maintained 3BR/2.5BA townhouse in desirable Windridge community. Features include updated laminate hardwood flooring, fireplace, eat-in kitchen, stainless steel appliances, private balcony off primary bedroom, sliding glass doors to private patio, attached 1-car garage with storage loft, and pull-down attic access. Community amenities include pool, clubhouse, and park.

    Martin Remo RE/MAX Prime Properties

    332 Heritage Ln, Monroe, NY 10950
  • 15 Vivian Ln, Chester, NY 10918

    $459,000

    Sold Aug 19, 2025

    15 Vivian Ln, Chester, NY 10918

    • 4 Beds
    • 2 Baths
    • 1,872 Sq Ft
    • Built 1968

    Last Sold Summary

    • 2% Above List Price
    • $245/SF
    • 25 Days On Market

    Current Estimated Value $475,173

    Last Listing Agent Joseph Giglio Keller Williams Realty

    15 Vivian Ln, Chester, NY 10918
  • L31 Clarkson Rd, Chester, NY 12817
    L31 Clarkson Rd, Chester, NY 12817
    L31 Clarkson Rd, Chester, NY 12817
    /14

    $129,000

    $30K PRICE DROP Pending
    • Land
    • 20,473 Sq Ft
    • $274,468 per Acre

    L31 Clarkson Rd, Chester, NY 12817

    Build Your Adirondack Getaway on Loon Lake!Enjoy beach rights on beautiful Loon Lake with this just-under-half-acre lot, the perfect spot to create your own year-round retreat or seasonal escape. Whether you dream of summer days by the water, paddling and swimming, or cozy winter weekends in the mountains, this property offers an ideal starting point for your Adirondack lifestyle.

    Brooke Clark Four Seasons Sotheby's International Realty

    L31 Clarkson Rd, Chester, NY 12817
  • 2913 Whispering Hills Unit 595, Chester, NY 10918

    $288,000

    Sold Apr 17, 2026

    2913 Whispering Hills Unit 595, Chester, NY 10918

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

    Last Sold Summary

    • 3% Above List Price
    • $266/SF
    • 18 Days On Market

    Current Estimated Value $285,826

    Last Listing Agent Devon King HomeSmart Homes & Estates

    2913 Whispering Hills Unit 595, Chester, NY 10918
    • 17 Surrey Rd, Chester, NY 10918

      Est $489,293

      Not Listed For Sale

      17 Surrey Rd, Chester, NY 10918

      • 3 Beds
      • 2 Baths
      • 1,712 Sq Ft
      • Built 1970
      17 Surrey Rd, Chester, NY 10918

      Last Sold Summary

      • 13 Days On Market

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