6,751

Chester, NY Homes

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  • 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
    • 27 Darin Rd, Warwick, NY 10990

      Est $357,711

      Not Listed For Sale

      27 Darin Rd, Warwick, NY 10990

      • 2 Beds
      • 2.5 Baths
      • 1,276 Sq Ft
      • Built 1987
      27 Darin Rd, Warwick, NY 10990

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Lauren Donati Homes By Yara Realty Group LLC

  • 1310 Whispering Hills, Chester, NY 10918
    1310 Whispering Hills, Chester, NY 10918
    1310 Whispering Hills, Chester, NY 10918
    /36

    $375,000

    Open Sun 12PM - 2PM
    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft

    1310 Whispering Hills, Chester, NY 10918

    Welcome to this comfortable 3-bedroom, 3-bathroom, end unit condo with a 2-car garage in the Whispering Hills community of Chester, NY. It’s the kind of place that feels easy the moment you walk in—spacious enough for everyday living, yet low-maintenance so you can actually enjoy your free time.Whispering Hills is one of those communities that just works. Residents get access to two outdoor

    Joseph Williams Hudson Premium Realty

    1310 Whispering Hills, Chester, NY 10918
  • 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
    • 25 Darin Rd, Warwick, NY 10990

      Est $366,640

      Not Listed For Sale

      25 Darin Rd, Warwick, NY 10990

      • 2 Beds
      • 2.5 Baths
      • 1,276 Sq Ft
      • Built 1987
      25 Darin Rd, Warwick, NY 10990

      Last Sold Summary

      • 96 Days On Market

      Last Listing Agent Michelle Cameron-Isaacs Keller Williams Realty

  • 72 Carriage Knoll Rd, Chester, NY 12817
    72 Carriage Knoll Rd, Chester, NY 12817
    72 Carriage Knoll Rd, Chester, NY 12817
    /23

    $68,900

    $19K PRICE INCREASE
    • Land
    • 3.11 Acres
    • $22,154 per Acre

    72 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    72 Carriage Knoll Rd, Chester, NY 12817
  • 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 Darin Rd, Warwick, NY 10990

      Est $414,922

      Not Listed For Sale

      31 Darin Rd, Warwick, NY 10990

      • 3 Beds
      • 2.5 Baths
      • 2,067 Sq Ft
      • Built 1987
      31 Darin Rd, Warwick, NY 10990

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Devon King HomeSmart Homes & Estates

  • 174 Eagleton Dr Unit 17D, Monroe, NY 10950
    174 Eagleton Dr Unit 17D, Monroe, NY 10950
    174 Eagleton Dr Unit 17D, Monroe, NY 10950
    /49

    $400,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,699 Sq Ft

    174 Eagleton Dr Unit 17D, Monroe, NY 10950

    Welcome to this beautifully maintained end-unit townhouse offering serene lakefront living and an exceptional array of community amenities, including a pool, playground, basketball & tennis courts. Freshly painted throughout the first floor and enhanced with elegant crown molding, this home showcases quality finishes and pride of ownership. Attractive vinyl plank flooring extends through the

    Donna Gennaro Howard Hanna Rand Realty

    174 Eagleton Dr Unit 17D, 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
    • 215 Ridge Rd, Chester, NY 10918

      Est $806,473

      Not Listed For Sale

      215 Ridge Rd, Chester, NY 10918

      • 3 Beds
      • 3 Baths
      • 3,005 Sq Ft
      • Built 1848
      215 Ridge Rd, Chester, NY 10918

      Last Sold Summary

      • 119 Days On Market

      Last Listing Agent Deborah Marks Keller Williams Realty

  • 63 Whitetail Run, Chester, NY 10918
    63 Whitetail Run, Chester, NY 10918
    63 Whitetail Run, Chester, NY 10918
    /38

    $1,200,000

    • 4 Beds
    • 2.5 Baths
    • 2,711 Sq Ft

    63 Whitetail Run, Chester, NY 10918

    This stunning 4 bedroom, 3 bathroom home with a beautifully updated kitchen is the perfect place to call home. With plenty of space to entertain and relax, you'll love the open layout and modern amenities that this home has to offer. Whether you're enjoying a meal in the spacious kitchen or unwinding in the cozy living room, you'll feel right at home in this charming and inviting space.

    Artan Kukaj SPIRAL NY Real Estate LLC

    63 Whitetail Run, 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
    • 16 Fernglade Ct, Chester, NY 10918

      Est $679,608

      Not Listed For Sale

      16 Fernglade Ct, Chester, NY 10918

      • 4 Beds
      • 3 Baths
      • 3,327 Sq Ft
      • Built 1973
      16 Fernglade Ct, Chester, NY 10918

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Kim Chiapperino RE/MAX Benchmark Realty Group

  • 1.4 Cobble Creek Rd Unit 4, Chester, NY 12853
    1.4 Cobble Creek Rd Unit 4, Chester, NY 12853
    1.4 Cobble Creek Rd Unit 4, Chester, NY 12853
    /10

    $99,995

    • Land
    • 22.88 Acres
    • $4,370 per Acre

    1.4 Cobble Creek Rd Unit 4, Chester, NY 12853

    Experience the best of Adirondack living on this scenic 22-acre property in Chester, New York. Accessible year-round from a town-maintained road with power nearby, the land offers several elevated APA-approved building sites perfectly positioned for a private cabin, vacation home, or full-time residence. The property is richly forested with mature Northern hardwoods including maple, oak, birch,

    Marc Christmas CHRISTMAS AND ASSOCIATES INC

    1.4 Cobble Creek Rd Unit 4, Chester, NY 12853
  • 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
    • 590 Craigville Rd, Chester, NY 10918

      Est $797,774

      Not Listed For Sale

      590 Craigville Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 3,152 Sq Ft
      • Built 2002
      590 Craigville Rd, Chester, NY 10918

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Lazar Schvimmer Blooming Realty

  • 234 Old River Rd, Chester, NY 12853
    234 Old River Rd, Chester, NY 12853
    234 Old River Rd, Chester, NY 12853
    /22

    $738,850

    Pending
    • Land
    • 561.54 Acres
    • $1,316 per Acre

    234 Old River Rd, Chester, NY 12853

    This property is 562 Ac of Adk field and forest with 2,000 ft. of frontage on the Hudson River, 2 beaver ponds, stream and trails. Structures on this dormant farm include an uninhabited house, barn and shed in need of rehab. An authentic log cabin is situated at a higher elevation above the field, beside an active beaver pond. Adjacent is a 'Morton' building, ideal for storage of equipment and

    John O'Donnell Timberland Realty

    234 Old River Rd, Chester, NY 12853
  • 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 Townsend Place, Chester, NY 10918

      Est $634,919

      Not Listed For Sale

      13 Townsend Place, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 3,108 Sq Ft
      • Built 1969
      13 Townsend Place, Chester, NY 10918

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Hershel Mittelman The Middleman Team

  • 815 Craigville Rd, Chester, NY 10918
    815 Craigville Rd, Chester, NY 10918
    815 Craigville Rd, Chester, NY 10918
    /50

    $280,000

    $161K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 2,016 Sq Ft

    815 Craigville Rd, Chester, NY 10918

    We are proud to introduce this cornerstone property, located within what was once a thriving enclave of artists. The same owner since 1946, this home and studio are part of a small collection of historic properties that helped define the character of the area. Now, an extraordinary opportunity awaits for the next steward to write the next chapter of this remarkable property.Originally built

    MaryBeth O'Hara Ellis Sotheby's Intl Realty

    815 Craigville Rd, Chester, NY 10918
  • 68 Walter Foote Rd, Chester, NY 12853
    68 Walter Foote Rd, Chester, NY 12853
    68 Walter Foote Rd, Chester, NY 12853
    /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
    • 11 Townsend Place, Chester, NY 10918

      Est $535,280

      Not Listed For Sale

      11 Townsend Place, Chester, NY 10918

      • 3 Beds
      • 1.5 Baths
      • 1,788 Sq Ft
      • Built 1968
      11 Townsend Place, Chester, NY 10918

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Lora Juncaj Exit Realty Venture

  • 3 Grand View Terrace, Chester, NY 10918
    3 Grand View Terrace, Chester, NY 10918
    3 Grand View Terrace, Chester, NY 10918
    /37

    $749,000

    • 6 Beds
    • 3 Baths
    • 3,066 Sq Ft

    3 Grand View Terrace, Chester, NY 10918

    Discover refined living at 3 Grand View Terrace, a beautiful 6-bedroom, 3-bath Colonial in Chester's sought-after Valley View Phase II subdivision. This impressive home boasts 3,066 sq ft of living space, with a full walkout basement and an attached 2-car garage. Built in 2003, it features central air and forced air heat. Relax by the fireplace or enjoy the outdoor space on the 0.55-acre lot.

    Shalom Landau eRealty Advisors, Inc

    3 Grand View Terrace, Chester, NY 10918
  • 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
    • 509 Laroe Rd, Chester, NY 10918

      Est $643,913

      Not Listed For Sale

      509 Laroe Rd, Chester, NY 10918

      • 4 Beds
      • 3 Baths
      • 2,350 Sq Ft
      • Built 1981
      509 Laroe Rd, Chester, NY 10918

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Bridget Wallace Howard Hanna Rand Realty

  • 16 Oakland Ave, Chester, NY 10918
    16 Oakland Ave, Chester, NY 10918
    16 Oakland Ave, Chester, NY 10918
    /49

    $425,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,090 Sq Ft

    16 Oakland Ave, Chester, NY 10918

    Charming 4-Bedroom Colonial in the Heart of Hudson Valley. Priced to Sell, tons of potential and great commuter location with close proximity tohighway! Welcome to this spacious 4-bedroom, 2.5-bath home nestled in the picturesque town of Chester, NY, in the heart of the beautifulHudson Valley. Offering 2,090 sq ft of living space, plus a finished rec room with an additional 1,026 sq ft,

    Vikki Garby BHG Real Estate Green Team

    16 Oakland Ave, Chester, NY 10918
  • 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
    • 138 Dug Rd, Chester, NY 10918

      Est $693,120

      Not Listed For Sale

      138 Dug Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,452 Sq Ft
      • Built 1974
      138 Dug Rd, Chester, NY 10918

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Jake Garay Serhant LLC

  • 424 Laroe Rd, Chester, NY 10918
    424 Laroe Rd, Chester, NY 10918
    424 Laroe Rd, Chester, NY 10918
    /40

    $649,999

    • 4 Beds
    • 3 Baths
    • 2,316 Sq Ft

    424 Laroe Rd, Chester, NY 10918

    Rare opportunity in Chester! This 4-bedroom, 3-bath raised ranch sits on a private 2.5-acre lot and features a true 6-car garage — an uncommon and highly desirable feature that sets this home apart. The oversized garage offers exceptional flexibility: perfect for the car enthusiast, contractor, large family, or anyone who needs serious storage, a workshop, or space for boats, RVs, or equipment.

    Jeffrey Morrissey Epique Realty

    424 Laroe Rd, Chester, NY 10918
  • 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
    • 16 Bianca Blvd, Chester, NY 10918

      Est $661,795

      Not Listed For Sale

      16 Bianca Blvd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 3,192 Sq Ft
      • Built 1987
      16 Bianca Blvd, Chester, NY 10918

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  • 2113 Whispering Hills Unit 178, Chester, NY 10918
    2113 Whispering Hills Unit 178, Chester, NY 10918
    2113 Whispering Hills Unit 178, Chester, NY 10918
    /24

    $295,000

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

    2113 Whispering Hills Unit 178, Chester, NY 10918

    Welcome Home! 2 Bedrooms 1 Bathroom move in ready end unit. Recently renovated including a new kitchen with granite counter tops and stainless steel appliances, new bathroom, new windows, new laminate flooring, new water heater, new light fixtures and recessed lighting. Nothing to do but move in! Close to supermarket, post office, restaurants, urgent care, highway. Perfect commuter location.

    Valerie Quinn Keller Williams Realty

    2113 Whispering Hills Unit 178, Chester, NY 10918
  • 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
    • 118 Murray Dr, Chester, NY 10918

      Est $811,368

      Not Listed For Sale

      118 Murray Dr, Chester, NY 10918

      • 5 Beds
      • 4 Baths
      • 3,418 Sq Ft
      • Built 1978
      118 Murray Dr, Chester, NY 10918

      Last Sold Summary

      • 110 Days On Market

      Last Listing Agent Brian Caplicki KW Hudson Valley United

  • 77 Carriage Knoll Rd, Chester, NY 12817
    77 Carriage Knoll Rd, Chester, NY 12817
    77 Carriage Knoll Rd, Chester, NY 12817
    /19

    $74,900

    $19K PRICE INCREASE
    • Land
    • 4.17 Acres
    • $17,962 per Acre

    77 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    77 Carriage Knoll Rd, Chester, NY 12817
  • 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
    • 142 Laroe Rd, Chester, NY 10918

      Est $678,598

      Not Listed For Sale

      142 Laroe Rd, Chester, NY 10918

      • 5 Beds
      • 3.5 Baths
      • 3,385 Sq Ft
      • Built 1981
      142 Laroe Rd, Chester, NY 10918

      Last Sold Summary

      • 107 Days On Market

      Last Listing Agent Peter Persaud HomeSmart Homes & Estates

  • 3 Hilltop Ln, Chester, NY 10918
    3 Hilltop Ln, Chester, NY 10918
    /2

    $750,000

    • 5 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    3 Hilltop Ln, Chester, NY 10918

    Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

    Moshe Kaufman MK Realty Inc

    3 Hilltop Ln, 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 $423,509

    Last Listing Agent Joel Ayala HomeSmart Homes & Estates

    354 Rande Rd Unit 354, Monroe, NY 10950

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