6,751

Chester, NY Homes

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  • 60 Whitetail Run, Chester, NY 10918
    60 Whitetail Run, Chester, NY 10918
    60 Whitetail Run, Chester, NY 10918
    /7

    $900,000

    • 4 Beds
    • 2.5 Baths
    • 2,588 Sq Ft

    60 Whitetail Run, Chester, NY 10918

    Beautifully maintained Colonial set on a picturesque and private property offering the perfect blend of comfort, space, This spacious home features an inviting layout with generously sized rooms, hardwood flooring, elegant moldings, and abundant natural light throughout. The heart of the home is the oversized eat-in kitchen with granite countertops, extensive cabinetry, pantry space, and

    Isaac Rottenberg Realty Blue Corp

    60 Whitetail Run, Chester, NY 10918
  • 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 $325,801

    Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

    307 Gibson Hill Rd, Chester, NY 10918
    • 101 Mountain Laurel Dr Unit 1A, Monroe, NY 10950

      Est $321,229

      Not Listed For Sale

      101 Mountain Laurel Dr Unit 1A, Monroe, NY 10950

      • 2 Beds
      • 2.5 Baths
      • 1,344 Sq Ft
      • Built 1979
      101 Mountain Laurel Dr Unit 1A, Monroe, NY 10950

      Last Sold Summary

      • 57 Days On Market

      Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

  • 34 Carriage Knolls Rd, Chester, NY 12817
    34 Carriage Knolls Rd, Chester, NY 12817
    34 Carriage Knolls Rd, Chester, NY 12817
    /8

    $39,500

    • Land
    • 1.82 Acres
    • $21,703 per Acre

    34 Carriage Knolls Rd, Chester, NY 12817

    Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

    Walter Swartz Gallo Realty ADK Inc

    34 Carriage Knolls Rd, Chester, NY 12817
  • 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 $669,258

    Last Listing Agent Kristie Jacques Century 21 Full Service Realty

    34 Booth Rd, Chester, NY 10918
    • 59 Wilson Rd, Monroe, NY 10950

      Est $570,477

      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

      Last Listing Agent Keith Sumner John J Lease REALTORS Inc

  • 2948 State Route 94, Chester, NY 10918
    2948 State Route 94, Chester, NY 10918
    2948 State Route 94, Chester, NY 10918
    /45

    $1,300,000

    $95K PRICE DROP Pending
    • 4 Beds
    • 2.5 Baths
    • 3,866 Sq Ft

    2948 State Route 94, Chester, NY 10918

    Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, this pristine 1860 farmhouse blends preserved historic character with thoughtful modern updates. Originally part of the Sears family dairy pasture, the 3,866 sq ft home has been meticulously maintained and features original wide-plank hardwood floors, a striking hand-carved banister, five fireplaces with

    Elizabeth Broderick Tuxedo Hudson Realty Corp

    2948 State Route 94, 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 $429,826

    Last Listing Agent Joao Rodrigues Preferred Properties Real Esta

    8 Hom St, Chester, NY 10918
    • 3 Grant Dr, Monroe, NY 10950

      Est $565,599

      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

      Last Listing Agent Rosalie Cook Weichert Realtors

  • 1401 Whispering Hills, Chester, NY 10918
    1401 Whispering Hills, Chester, NY 10918
    1401 Whispering Hills, Chester, NY 10918
    /33

    $260,000

    $35K PRICE DROP Pending
    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft

    1401 Whispering Hills, Chester, NY 10918

    Discover the perfect blend of comfort, convenience, and community in this 2-bedroom, 1-bath end-unit townhouse. Situated in a quiet corner of the neighborhood, this home offers extra privacy and natural light, along with the added benefit of an attached 1-car garage for secure parking and storage. Inside, you'll find a thoughtfully designed layout that maximizes space and livability - ideal for

    Debbie Goldstein Howard Hanna Rand Realty

    1401 Whispering Hills, 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 $470,360

    Last Listing Agent Matthew Skowronski HomeSmart Homes & Estates

    4 Wood Rd, Chester, NY 10918
    • 1 Grant Dr, Monroe, NY 10950

      Est $517,781

      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

      Last Listing Agent Joanne Finochio Howard Hanna Rand Realty

  • 11 Chandler Dr, Chester, NY 10918
    11 Chandler Dr, Chester, NY 10918
    11 Chandler Dr, Chester, NY 10918
    /32

    $575,000

    $40K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,908 Sq Ft

    11 Chandler Dr, Chester, NY 10918

    Welcome to this beautifully maintained raised ranch, perfectly situated on a desirable corner lot in Chester. This inviting 3-bedroom, 2 full and 1 half bath home blends comfort, style, and modern convenience in a location you'll love. Filled with natural light, the home features spacious living areas and a well-appointed kitchen with stainless steel appliances. The finished basement offers

    Daniella Restrepo Coldwell Banker Realty

    11 Chandler Dr, 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 $620,668

    Last Listing Agent Alissa Taylor-Vetell Keller Williams Realty

    7 Cambridge Cir, Monroe, NY 10950
    • 9 Adams Ct, Monroe, NY 10950

      Est $584,806

      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

      Last Listing Agent Frank Muccari Cronin & Company Real Estate

  • 36 Fawn Ridge Rd, Chester, NY 12817
    36 Fawn Ridge Rd, Chester, NY 12817
    36 Fawn Ridge Rd, Chester, NY 12817
    /3

    $150,000

    • Land
    • 5.14 Acres
    • $29,183 per Acre

    36 Fawn Ridge Rd, Chester, NY 12817

    Must see building site which has panoramic views overlooking Gore Mountain Range to the North but possible 360 degree Mountain View's with some clearing necessary.

    John Palermo John R. Palermo

    36 Fawn Ridge Rd, Chester, NY 12817
    • 59 Washington Rd, Monroe, NY 10950

      Est $569,998

      Not Listed For Sale

      59 Washington Rd, Monroe, NY 10950

      • 4 Beds
      • 2 Baths
      • 1,894 Sq Ft
      • Built 1973
      59 Washington Rd, Monroe, NY 10950

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Rebecca Kane KW Hudson Valley United

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

    $500,000

    Pending
    • 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
  • 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 $527,927

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

    25 High St, Chester, NY 10918
    • 26 Harding Way, Monroe, NY 10950

      Est $553,771

      Not Listed For Sale

      26 Harding Way, Monroe, NY 10950

      • 4 Beds
      • 2 Baths
      • 1,744 Sq Ft
      • Built 1979
      26 Harding Way, Monroe, NY 10950

      Last Sold Summary

      • 58 Days On Market

      Last Listing Agent Carmela Lopez Borrazas Serhant LLC

  • 35 Maple Ave, Chester, NY 10918
    35 Maple Ave, Chester, NY 10918
    35 Maple Ave, Chester, NY 10918
    /29

    $489,900

    $60K PRICE DROP Pending
    • 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
  • 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 $476,772

    Last Listing Agent Joseph Giglio Keller Williams Realty

    15 Vivian Ln, Chester, NY 10918
    • 2 Tyler Place, Monroe, NY 10950

      Est $583,169

      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

      Last Listing Agent Claudia Lepore Keller Williams Realty

  • 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
  • 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 $288,400

    Last Listing Agent Devon King HomeSmart Homes & Estates

    2913 Whispering Hills Unit 595, Chester, NY 10918
    • 92 Pickerel Rd, Monroe, NY 10950

      Est $583,846

      Not Listed For Sale

      92 Pickerel Rd, Monroe, NY 10950

      • 3 Beds
      • 2 Baths
      • 2,016 Sq Ft
      • Built 1969
      92 Pickerel Rd, Monroe, NY 10950

      Last Sold Summary

      • 148 Days On Market

      Last Listing Agent Richard Wawrynek Howard Hanna Rand Realty

  • 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
  • 2203 Whispering Hills, Chester, NY 10918

    $348,000

    Sold Jun 11, 2026

    2203 Whispering Hills, Chester, NY 10918

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

    Last Sold Summary

    • 6% Below List Price
    • $261/SF
    • 47 Days On Market

    Current Estimated Value $351,372

    Last Listing Agent Marie Altieri Howard Hanna Rand Realty

    2203 Whispering Hills, Chester, NY 10918
    • 63 Pickerel Rd, Monroe, NY 10950

      Est $575,084

      Not Listed For Sale

      63 Pickerel Rd, Monroe, NY 10950

      • 4 Beds
      • 2 Baths
      • 2,092 Sq Ft
      • Built 1969
      63 Pickerel Rd, Monroe, NY 10950

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Henry Raymond Thomas M David

  • 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

    $88,500

    $1K PRICE DROP
    • Land
    • 12.79 Acres
    • $6,919 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
  • 3601 Whispering Hills, Chester, NY 10918

    $296,000

    Sold Jun 05, 2026

    3601 Whispering Hills, Chester, NY 10918

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft
    • Built 1990

    Last Sold Summary

    • 3% Below List Price
    • $273/SF
    • 23 Days On Market

    Current Estimated Value $296,837

    Last Listing Agent Janet Rendle Weichert Realtors

    3601 Whispering Hills, Chester, NY 10918
    • 17 Surrey Rd, Chester, NY 10918

      Est $485,095

      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

      Last Listing Agent Frank Muccari Cronin & Company Real Estate

  • 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

    Pending
    • 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
  • 252 Heritage Ln, Monroe, NY 10950

    $369,000

    Sold Jan 09, 2026

    252 Heritage Ln, Monroe, NY 10950

    • 3 Beds
    • 2.5 Baths
    • 1,585 Sq Ft
    • Built 1988

    Last Sold Summary

    • $233/SF
    • 55 Days On Market

    Current Estimated Value $376,128

    Last Listing Agent Brenda Wiley Howard Hanna Rand Realty

    252 Heritage Ln, Monroe, NY 10950
    • 69 Dug Rd, Chester, NY 10918

      Est $718,131

      Not Listed For Sale

      69 Dug Rd, Chester, NY 10918

      • 4 Beds
      • 3 Baths
      • 3,006 Sq Ft
      • Built 2001
      69 Dug Rd, Chester, NY 10918

      Last Sold Summary

      • 124 Days On Market

      Last Listing Agent Kim Chiapperino RE/MAX Benchmark Realty Group

  • 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
  • 2503 Whispering Hills, Chester, NY 10918

    $340,000

    Sold Oct 15, 2025

    2503 Whispering Hills, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,316 Sq Ft
    • Built 1986

    Last Sold Summary

    • 8% Below List Price
    • $258/SF
    • 59 Days On Market

    Current Estimated Value $347,984

    Last Listing Agent Sonia Gonzalez HomeSmart Homes & Estates

    2503 Whispering Hills, Chester, NY 10918
    • 16 Twin Brooks Dr, Chester, NY 10918

      Est $683,593

      Not Listed For Sale

      16 Twin Brooks Dr, Chester, NY 10918

      • 3 Beds
      • 4 Baths
      • 2,708 Sq Ft
      • Built 1968
      16 Twin Brooks Dr, Chester, NY 10918

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Layla Rose Boyles Century 21 Realty Center

  • 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

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