6,751

Chester, NY Homes

Section Image
    • 225 Eagleton Dr, Monroe, NY 10950

      Est $424,163

      Not Listed For Sale

      225 Eagleton Dr, Monroe, NY 10950

      • 3 Beds
      • 2.5 Baths
      • 1,694 Sq Ft
      • Built 1997
      225 Eagleton Dr, Monroe, NY 10950

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Theresa Budich Howard Hanna Rand Realty

  • 66 Whitetail Run, Chester, NY 10918
    66 Whitetail Run, Chester, NY 10918
    66 Whitetail Run, Chester, NY 10918
    /50

    $449,000

    Open Sat 12PM - 2PM
    • 3 Beds
    • 1.5 Baths
    • 1,500 Sq Ft

    66 Whitetail Run, Chester, NY 10918

    Welcome to 66 Whitetail Run – Chester, NY. Tucked back from the road on an ample, tree-lined lot, this charming contemporary colonial offers the perfect blend of privacy and convenience in the Monroe-Woodbury school district. Surrounded by nature and filled with birdsong, this peaceful setting feels like a retreat while still being close to all local amenities. Step inside to a bright, open

    Soleil Jackman Howard Hanna Rand Realty

    66 Whitetail Run, Chester, NY 10918
  • 16 Mari Rd, Chester, NY 10918

    $501,500

    Sold Mar 03, 2026

    16 Mari Rd, Chester, NY 10918

    • 4 Beds
    • 3 Baths
    • 2,098 Sq Ft
    • Built 1970

    Last Sold Summary

    • $239/SF
    • 75 Days On Market

    Current Estimated Value $513,208

    Last Listing Agent Kimberly Corkum Keller Williams Realty

    16 Mari Rd, Chester, NY 10918
    • 2 Laura Dr, Chester, NY 10918

      Est $694,738

      Not Listed For Sale

      2 Laura Dr, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,592 Sq Ft
      • Built 1986
      2 Laura Dr, Chester, NY 10918

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Virginia Corbett eXp Realty

  • 98 Carriage Knoll Rd, Chester, NY 12817
    98 Carriage Knoll Rd, Chester, NY 12817
    98 Carriage Knoll Rd, Chester, NY 12817
    /20

    $68,900

    $19K PRICE INCREASE
    • Land
    • 3.26 Acres
    • $21,135 per Acre

    98 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

    98 Carriage Knoll Rd, Chester, NY 12817
  • 2915 Whispering Hills Unit 596, Chester, NY 10918

    $382,000

    Sold Mar 25, 2026

    2915 Whispering Hills Unit 596, Chester, NY 10918

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

    Last Sold Summary

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

    Current Estimated Value $376,228

    Last Listing Agent Johanna Monzon Ruballos Century 21 Full Service Realty

    2915 Whispering Hills Unit 596, Chester, NY 10918
    • 14 Jeffrey Dr, Chester, NY 10918

      Est $610,507

      Not Listed For Sale

      14 Jeffrey Dr, Chester, NY 10918

      • 3 Beds
      • 2.5 Baths
      • 2,117 Sq Ft
      • Built 1987
      14 Jeffrey Dr, Chester, NY 10918

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Savannah Miceli Century 21 Alliance Rlty Group

  • 3 Boville Ct, Chester, NY 10918
    3 Boville Ct, Chester, NY 10918
    3 Boville Ct, Chester, NY 10918
    /50

    $750,000

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

    3 Boville Ct, 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

    Dovid Hoffman MK Realty Inc

    3 Boville Ct, Chester, NY 10918
  • 3917 Whispering Hills, Chester, NY 10918

    $305,000

    Sold Jun 05, 2026

    3917 Whispering Hills, Chester, NY 10918

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • Built 1987

    Last Sold Summary

    • 4% Below List Price
    • $285/SF
    • 138 Days On Market

    Current Estimated Value $305,793

    Last Listing Agent Jie Liu KW Hudson Valley United

    3917 Whispering Hills, Chester, NY 10918
    • 19 Well Sweep Ln, Chester, NY 10918

      Est $479,563

      Not Listed For Sale

      19 Well Sweep Ln, Chester, NY 10918

      • 2 Beds
      • 2 Baths
      • 1,650 Sq Ft
      • Built 1987
      19 Well Sweep Ln, Chester, NY 10918

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Donna Brunell RE/MAX Benchmark Realty Group

  • 412 Laroe Rd, Chester, NY 10918
    412 Laroe Rd, Chester, NY 10918
    412 Laroe Rd, Chester, NY 10918
    /46

    $615,000

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft

    412 Laroe Rd, Chester, NY 10918

    Imagine coming home to your own private retreat, nestled on over 2 beautiful acres in the heart of the Hudson Valley. This stunning home offers the perfect blend of comfort, style, and tranquility, creating an oasis both inside and out. Step inside to a sun-drenched living room featuring soaring cathedral ceilings and a dramatic wall of windows that fills the space with natural light. The

    Nathalie Sessoms Howard Hanna Rand Realty

    412 Laroe Rd, Chester, NY 10918
  • 3910 Whispering Hills, Chester, NY 10918

    $369,900

    Sold Jul 17, 2026

    3910 Whispering Hills, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft
    • Built 1989

    Last Sold Summary

    • $278/SF
    • 133 Days On Market

    Current Estimated Value $369,131

    Last Listing Agent Randolph Rogers eXp Realty

    3910 Whispering Hills, Chester, NY 10918
    • 51 Well Sweep Ln, Chester, NY 10918

      Est $648,667

      Not Listed For Sale

      51 Well Sweep Ln, Chester, NY 10918

      • 3 Beds
      • 3 Baths
      • 2,075 Sq Ft
      • Built 1985
      51 Well Sweep Ln, Chester, NY 10918

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Claudia Vaccaro Howard Hanna Rand Realty

  • 220 Oxford Rd, Chester, NY 10918
    220 Oxford Rd, Chester, NY 10918
    /2

    $350,000

    • Land
    • 2 Acres
    • $175,000 per Acre

    220 Oxford Rd, Chester, NY 10918

    A rare opportunity in Blooming Grove! This beautiful and flat 2-acre property offers endless potential in a calm and peaceful setting with a road frontage. Conveniently located just minutes from Prospect Garden, the land sits within the Monroe-Woodbury School District. With easy access to permits, this property is ideal for building your dream home or future investment. The neighborhood holds

    Chaim Weiss MS Realty Group USA, Inc

    220 Oxford Rd, Chester, NY 10918
  • 23 Pewter Cir, Chester, NY 10918

    $675,000

    Sold Feb 20, 2026

    23 Pewter Cir, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,318 Sq Ft
    • Built 1998

    Last Sold Summary

    • 4% Above List Price
    • $291/SF
    • 21 Days On Market

    Current Estimated Value $672,791

    Last Listing Agent Rosemary DelliCarpini eXp Realty

    23 Pewter Cir, Chester, NY 10918
    • 1103 Deerfield Rd, Monroe, NY 10950

      Est $307,765

      Not Listed For Sale

      1103 Deerfield Rd, Monroe, NY 10950

      • 3 Beds
      • 1.5 Baths
      • 1,240 Sq Ft
      • Built 1979
      1103 Deerfield Rd, Monroe, NY 10950

      Last Sold Summary

      • 76 Days On Market

      Last Listing Agent Michael Chang Howard Hanna Rand Realty

  • 2119 Whispering Hills, Chester, NY 10918
    2119 Whispering Hills, Chester, NY 10918
    2119 Whispering Hills, Chester, NY 10918
    /32

    $295,000

    • 2 Beds
    • 1.5 Baths
    • 1,086 Sq Ft

    2119 Whispering Hills, Chester, NY 10918

    Step into this gorgeous Townhouse.Upon entering you’ll be welcomed by a perfect floor plan. The inviting living room features wooden floors, a cozy fireplace, and windows. The stylish kitchen has a functional layout and is outfitted with stainless steel appliances and granite countertops. The master-bedroom offers a modern feel and a walk in closet. Enjoy the amenity centers. Stop dreaming and

    Jasmine Wadhwa Howard Hanna Rand Realty

    2119 Whispering Hills, Chester, NY 10918
  • 4116 Whispering Hills, Chester, NY 10918

    $385,000

    Sold Jul 06, 2026

    4116 Whispering Hills, Chester, NY 10918

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

    Last Sold Summary

    • 3% Above List Price
    • $284/SF
    • 21 Days On Market

    Current Estimated Value $372,917

    Last Listing Agent Michael Casarella William Raveis-New York, LLC

    4116 Whispering Hills, Chester, NY 10918
    • 1004 Swan Hollow Rd, Monroe, NY 10950

      Est $345,962

      Not Listed For Sale

      1004 Swan Hollow Rd, Monroe, NY 10950

      • 3 Beds
      • 2.5 Baths
      • 1,334 Sq Ft
      • Built 1979
      1004 Swan Hollow Rd, Monroe, NY 10950

      Last Sold Summary

      • 175 Days On Market

      Last Listing Agent Andrea Rose KW Hudson Valley United

  • 2 Heidi Ln, Chester, NY 10918
    2 Heidi Ln, Chester, NY 10918
    2 Heidi Ln, Chester, NY 10918
    /44

    $869,000

    $31K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 3,846 Sq Ft

    2 Heidi Ln, Chester, NY 10918

    Set at the end of a quiet executive cul-de-sac, this refined modern colonial offers a rare blend of quality, scale, and effortless livability on over two acres of level, park-like grounds framed by mature trees. Designed for both everyday comfort and elevated entertaining, the home unfolds with a sense of openness and intention, where natural light and thoughtful craftsmanship define every

    Frank Muccari Cronin & Company Real Estate

    2 Heidi Ln, Chester, NY 10918
  • 114 Old Mansion Rd, Chester, NY 10918

    $555,000

    Sold Oct 21, 2025

    114 Old Mansion Rd, Chester, NY 10918

    • 4 Beds
    • 2 Baths
    • 3,330 Sq Ft
    • Built 1930

    Last Sold Summary

    • 21% Below List Price
    • $167/SF
    • 76 Days On Market

    Current Estimated Value $650,105

    Last Listing Agent Hershel Lowy Master Realty Group Inc.

    114 Old Mansion Rd, Chester, NY 10918
    • 904 Swan Hollow Rd, Monroe, NY 10950

      Est $346,897

      Not Listed For Sale

      904 Swan Hollow Rd, Monroe, NY 10950

      • 3 Beds
      • 2.5 Baths
      • 1,320 Sq Ft
      • Built 1979
      904 Swan Hollow Rd, Monroe, NY 10950

      Last Sold Summary

      • 125 Days On Market

      Last Listing Agent Stephen Ramundo Keller Williams Valley Realty

  • 19 Greentree Ln, Chester, NY 10918
    19 Greentree Ln, Chester, NY 10918
    19 Greentree Ln, Chester, NY 10918
    /50

    $3,400,000

    • 4 Beds
    • 4 Baths
    • 7,750 Sq Ft

    19 Greentree Ln, Chester, NY 10918

    Set behind a gated entrance with a private guard house and unfolding across 8.4 private acres, The Retreat at Greentree is a true estate in every sense, engineered for privacy, designed for lifestyle, and positioned as one of the most unique offerings in the Hudson Valley. A cascading waterfall greets you on arrival, establishing a sense of calm and separation from the outside world. From that

    Jake Garay Serhant LLC

    19 Greentree Ln, Chester, NY 10918
  • 2 Dawn Ct, Chester, NY 10918

    $669,000

    Sold Jan 12, 2026

    2 Dawn Ct, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 3,092 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Below List Price
    • $216/SF
    • 76 Days On Market

    Current Estimated Value $672,856

    Last Listing Agent Dulce M Ferrera KW Hudson Valley United

    2 Dawn Ct, Chester, NY 10918
    • 901 Swan Hollow Rd, Monroe, NY 10950

      Est $351,078

      Not Listed For Sale

      901 Swan Hollow Rd, Monroe, NY 10950

      • 3 Beds
      • 2.5 Baths
      • 1,334 Sq Ft
      • Built 1979
      901 Swan Hollow Rd, Monroe, NY 10950

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent William Fowlkes Howard Hanna Rand Realty

  • 29 Murray Dr, Chester, NY 10918
    29 Murray Dr, Chester, NY 10918
    29 Murray Dr, Chester, NY 10918
    /34

    $650,000

    • 3 Beds
    • 4 Baths
    • 2,520 Sq Ft

    29 Murray Dr, Chester, NY 10918

    Welcome to a contemporary retreat where refined design, exceptional craftsmanship, and a seamless connection to nature come together in one of Chester’s most desirable settings. Thoughtfully designed for both everyday living and effortless entertaining, this light-filled residence offers three bedrooms, two full bathrooms, and two half baths with an open, flowing floor plan that balances

    Liudmila Lobeeva eXp Realty

    29 Murray Dr, 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 $240,569

    Last Listing Agent Maureen Schroder Keller Williams Valley Realty

    42 Heaton Rd, Monroe, NY 10950
    • 808 Swan Hollow Rd, Monroe, NY 10950

      Est $324,202

      Not Listed For Sale

      808 Swan Hollow Rd, Monroe, NY 10950

      • 3 Beds
      • 1.5 Baths
      • 1,240 Sq Ft
      • Built 1979
      808 Swan Hollow Rd, Monroe, NY 10950

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Vincent Paolino Keller Williams Hudson Valley

  • 24 Walnut St, Chester, NY 10918
    24 Walnut St, Chester, NY 10918
    24 Walnut St, Chester, NY 10918
    /28

    $559,000

    $21K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,698 Sq Ft

    24 Walnut St, Chester, NY 10918

    Welcome to 24 Walnut Street, Flexibility, Space & Endless Possibility in the Heart of Chester, NYTucked on a generous half-acre lot in the charming Village of Chester, this versatile 4-bedroom, 2.5-bath home offers a rare mother-daughter layout that delivers the best of both worlds, income potential, or simply more space to grow. Set on a quiet, tree-lined street just minutes from the Orange

    Tara Roufanis Keller Williams Village Sq Rlt

    24 Walnut St, 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 $636,471

    Last Listing Agent Dean Diltz Keller Williams Realty

    81 Hambletonian Rd, Chester, NY 10918
    • 707 Swan Hollow Rd, Monroe, NY 10950

      Est $366,721

      Not Listed For Sale

      707 Swan Hollow Rd, Monroe, NY 10950

      • 3 Beds
      • 2.5 Baths
      • 1,840 Sq Ft
      • Built 1979
      707 Swan Hollow Rd, Monroe, NY 10950

      Last Sold Summary

      • 78 Days On Market

      Last Listing Agent James Flood Master Realty Group Inc.

  • 30 Harding Way, Chester, NY 10950
    30 Harding Way, Chester, NY 10950
    30 Harding Way, Chester, NY 10950
    /7

    $500,000

    • Land
    • 9.78 Acres
    • $51,125 per Acre

    30 Harding Way, Chester, NY 10950

    An exceptional opportunity for builders and investors in the highly desirable Town of Chester and Town of Monroe, within the Monroe–Woodbury School District. This offering includes four contiguous lots for the price of one, providing significant development potential. The assemblage consists of 30 Harding Way (0.18 acres; Section 27, Block 3, Lot 11), sold together with the adjoining parcels: Lot

    Ida Payne Keller Williams Realty

    30 Harding Way, Chester, NY 10950
  • 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 $488,644

    Last Listing Agent Jay Himelson Howard Hanna Rand Realty

    24 Oak Dr, Monroe, NY 10950
    • 604 Mountain Laurel Dr, Monroe, NY 10950

      Est $379,261

      Not Listed For Sale

      604 Mountain Laurel Dr, Monroe, NY 10950

      • 3 Beds
      • 2.5 Baths
      • 1,825 Sq Ft
      • Built 1979
      604 Mountain Laurel Dr, Monroe, NY 10950

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Emmett McDowell Keller Williams Rlty Integrity

  • 2703 Whispering Hills, Chester, NY 10918
    2703 Whispering Hills, Chester, NY 10918
    2703 Whispering Hills, Chester, NY 10918
    /39

    $365,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft

    2703 Whispering Hills, Chester, NY 10918

    Welcome to 2703 Whispering Hills in Chester, NY — a beautifully updated home that stands out from the rest. This well-maintained unit features numerous recent improvements, including new windows, a new garage door, and a new hot water heater, providing peace of mind for years to come. The central air conditioning system is approximately five years old and keeps the home comfortable throughout the

    Rebecca Matta-Candela Keller Williams Realty

    2703 Whispering Hills, 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 $558,433

    Last Listing Agent Amy Wilhelm Corcoran Baer & McIntosh

    358 Bull Mill Rd, Chester, NY 10918
    • 601 Mountain Laurel Dr, Monroe, NY 10950

      Est $336,983

      Not Listed For Sale

      601 Mountain Laurel Dr, Monroe, NY 10950

      • 3 Beds
      • 2.5 Baths
      • 1,334 Sq Ft
      • Built 1979
      601 Mountain Laurel Dr, Monroe, NY 10950

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Bernadette Corrigan Keller Williams Realty

  • 213 Eagleton Dr, Monroe, NY 10950
    213 Eagleton Dr, Monroe, NY 10950
    213 Eagleton Dr, Monroe, NY 10950
    /32

    $389,900

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

    213 Eagleton Dr, Monroe, NY 10950

    Some homes simply make everyday life easier, and 213 Eagleton Drive is one of them. This 3-bedroom, 2.5-bath townhome offers a practical layout with comfortable living spaces, an attached garage, additional driveway parking, and an unfinished basement for lots of storage. During the winter months, the home offers views of the community lake, adding a peaceful backdrop to the changing

    Deborah Warner Keller Williams Valley Realty

    213 Eagleton Dr, Monroe, NY 10950
  • 195 Eagleton Dr, Monroe, NY 10950

    $425,000

    Sold Jul 14, 2026

    195 Eagleton Dr, Monroe, NY 10950

    • 3 Beds
    • 2.5 Baths
    • 1,762 Sq Ft
    • Built 1997

    Last Sold Summary

    • 8% Above List Price
    • $241/SF
    • 21 Days On Market

    Current Estimated Value $397,509

    Last Listing Agent Patricia Spagna Century 21 Realty Center

    195 Eagleton Dr, Monroe, NY 10950
    • 204 Mountain Laurel Dr, Monroe, NY 10950

      Est $342,128

      Not Listed For Sale

      204 Mountain Laurel Dr, Monroe, NY 10950

      • 3 Beds
      • 2.5 Baths
      • 1,334 Sq Ft
      • Built 1979
      204 Mountain Laurel Dr, Monroe, NY 10950

      Last Sold Summary

      • 87 Days On Market

      Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

Showing Results 241 - 280, Page 7 of 18

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