6,841

Chester, NY Homes

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  • 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
  • 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 $361,547

    Last Listing Agent Marie Altieri Howard Hanna Rand Realty

    2203 Whispering Hills, Chester, NY 10918
    • 73 Dug Rd, Chester, NY 10918

      Est $614,233

      Not Listed For Sale

      73 Dug Rd, Chester, NY 10918

      • 5 Beds
      • 4 Baths
      • 2,554 Sq Ft
      • Built 1971
      73 Dug Rd, Chester, NY 10918

      Last Sold Summary

      • 69 Days On Market

  • 150 Lake Region Blvd, Monroe, NY 10950
    150 Lake Region Blvd, Monroe, NY 10950
    150 Lake Region Blvd, Monroe, NY 10950
    /44

    $549,000

    $31K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,112 Sq Ft

    150 Lake Region Blvd, Monroe, NY 10950

    Welcome to 150 Lake Region Blvd, a beautifully maintained home in Monroe’s sought-after Lake Region / Walton Park community. Step inside to warm hardwood floors and a thoughtfully designed layout that feels both inviting and functional. The main living spaces flow effortlessly, creating an ideal setting for everyday living and entertaining. Offering 4 spacious bedrooms and 3 full bathrooms, the

    Pete Wolven Hudson Valley Home Connection

    150 Lake Region Blvd, Monroe, NY 10950
  • 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 $303,971

    Last Listing Agent Janet Rendle Weichert Realtors

    3601 Whispering Hills, Chester, NY 10918
  • 20 Goshen Rd, Chester, NY 10918
    20 Goshen Rd, Chester, NY 10918
    20 Goshen Rd, Chester, NY 10918
    /50

    $1,725,000

    • 4 Beds
    • 2.5 Baths
    • 3,348 Sq Ft

    20 Goshen Rd, Chester, NY 10918

    THE ULTIMATE HUDSON VALLEY LEGACY ESTATE | 53 ACRES OF UNMATCHED POTENTIAL Rarely does a property emerge that perfectly balances refined luxury living with raw, untapped opportunity. Nestled in the heart of scenic Chester, New York, 20 Goshen Road offers an expansive 53-acre canvas designed for the visionary. Whether you envision a world-class equestrian facility, a high-potential residential

    Ramanjit Dhanoa eXp Realty

    20 Goshen Rd, Chester, NY 10918
  • 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 $370,541

    Last Listing Agent Brenda Wiley Howard Hanna Rand Realty

    252 Heritage Ln, Monroe, NY 10950
    • 46 Ayr Rd, Chester, NY 10918

      Est $649,765

      Not Listed For Sale

      46 Ayr Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,784 Sq Ft
      • Built 1971
      46 Ayr Rd, Chester, NY 10918

      Last Sold Summary

      • 70 Days On Market

  • 2 Garnett Hill Rd, Chester, NY 10918
    2 Garnett Hill Rd, Chester, NY 10918
    2 Garnett Hill Rd, Chester, NY 10918
    /35

    $999,999

    • 5 Beds
    • 2.5 Baths
    • 4,772 Sq Ft

    2 Garnett Hill Rd, Chester, NY 10918

    A Private Suburban Retreat on Prestigious Garnet Hill. This Center Hall Colonial offers an exceptional residence- refined suburban living with the space, privacy, and sophistication sought by discerning buyers—just about an hour from Manhattan. Positioned on a beautifully landscaped 3+ acre property, the home features approximately over 4,700 square feet of elegant living space, offering 5

    Rachel Baruchov Platinum Realty Associates

    2 Garnett Hill Rd, Chester, NY 10918
  • 904 Swan Hollow Rd, Monroe, NY 10950

    $340,000

    Sold Jun 25, 2025

    904 Swan Hollow Rd, Monroe, NY 10950

    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft
    • Built 1979

    Last Sold Summary

    • 3% Below List Price
    • $258/SF
    • 125 Days On Market

    Current Estimated Value $336,352

    Last Listing Agent Stephen Ramundo Keller Williams Valley Realty

    904 Swan Hollow Rd, Monroe, NY 10950
    • 13 Mari Rd, Chester, NY 10918

      Est $443,363

      Not Listed For Sale

      13 Mari Rd, Chester, NY 10918

      • 3 Beds
      • 1.5 Baths
      • 1,358 Sq Ft
      • Built 1970
      13 Mari Rd, Chester, NY 10918

      Last Sold Summary

      • 40 Days On Market

  • 487 Black Meadow Rd, Chester, NY 10918
    487 Black Meadow Rd, Chester, NY 10918
    487 Black Meadow Rd, Chester, NY 10918
    /50

    $725,000

    • 6 Beds
    • 3.5 Baths
    • 4,204 Sq Ft

    487 Black Meadow Rd, Chester, NY 10918

    A Landmark Farmhouse with a Story to Tell.Standing proudly since 1872, this historic Colonial farmhouse is one of the very first homes built on Black Meadow Road and remains a meaningful piece of Chester’s agricultural past. Once surrounded by hundreds of acres of open farmland and dairy cows, the home still carries the soul of a working farm while offering the comforts of modern living. With

    Dominic Santagato Joseph Baratta Company Realty

    487 Black Meadow 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 $347,916

    Last Listing Agent Sonia Gonzalez HomeSmart Homes & Estates

    2503 Whispering Hills, Chester, NY 10918
    • 14 Mari Rd, Chester, NY 10918

      Est $485,622

      Not Listed For Sale

      14 Mari Rd, Chester, NY 10918

      • 3 Beds
      • 1.5 Baths
      • 1,926 Sq Ft
      • Built 1970
      14 Mari Rd, Chester, NY 10918

      Last Sold Summary

      • 12 Days On Market

  • 7 Hambletonian Ave, Chester, NY 10918
    7 Hambletonian Ave, Chester, NY 10918
    7 Hambletonian Ave, Chester, NY 10918
    /26

    $399,900

    $25K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,026 Sq Ft

    7 Hambletonian Ave, Chester, NY 10918

    Great new price! Come take a look at this 2 bedroom charmer with additional room offers potential 3+ bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay

    William Scolza HomeSmart Homes & Estates

    7 Hambletonian Ave, Chester, NY 10918
  • 16 Oxford Springs Rd, Chester, NY 10918

    $725,000

    Sold May 27, 2026

    16 Oxford Springs Rd, Chester, NY 10918

    • 3 Beds
    • 3 Baths
    • 2,870 Sq Ft
    • Built 1988

    Last Sold Summary

    • 7% Below List Price
    • $253/SF
    • 117 Days On Market

    Current Estimated Value $740,162

    Last Listing Agent Jennifer Gold RE/MAX Benchmark Realty Group

    16 Oxford Springs Rd, Chester, NY 10918
    • 62 Surrey Rd, Chester, NY 10918

      Est $514,465

      Not Listed For Sale

      62 Surrey Rd, Chester, NY 10918

      • 4 Beds
      • 1.5 Baths
      • 1,872 Sq Ft
      • Built 1968
      62 Surrey Rd, Chester, NY 10918

      Last Sold Summary

      • 37 Days On Market

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

    $74,900

    $19K PRICE INCREASE
    • Land
    • 4.05 Acres
    • $18,494 per Acre

    85 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

    85 Carriage Knoll Rd, Chester, NY 12817
  • 12 Oak St, Chester, NY 10918

    $415,000

    Sold Jul 03, 2025

    12 Oak St, Chester, NY 10918

    • 3 Beds
    • 1 Bath
    • 1,038 Sq Ft
    • Built 1959

    Last Sold Summary

    • 5% Above List Price
    • $400/SF
    • 24 Days On Market

    Current Estimated Value $410,239

    Last Listing Agent Jennifer Loprieno Howard Hanna Rand Realty

    12 Oak St, Chester, NY 10918
  • 49 Stone Mountain Trail, Chester, NY 10918
    49 Stone Mountain Trail, Chester, NY 10918
    49 Stone Mountain Trail, Chester, NY 10918
    /35

    $875,000

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

    49 Stone Mountain Trail, Chester, NY 10918

    Escape to your own private retreat at 49 Stone Mountain Trail. Tucked away on more than 7 acres with mountain views, this contemporary home delivers the perfect balance of comfort, space, and outdoor enjoyment. Imagine mornings filled with sunlight streaming through oversized windows, evenings gathered around the stone fireplace, and summers spent relaxing by the in-ground pool surrounded by

    Arya Rabinovits eRealty Advisors, Inc

    49 Stone Mountain Trail, Chester, NY 10918
  • 40 Poplar Dr, Monroe, NY 10950

    $465,000

    Sold Jun 18, 2026

    40 Poplar Dr, Monroe, NY 10950

    • 3 Beds
    • 2 Baths
    • 1,108 Sq Ft
    • Built 1972

    Last Sold Summary

    • 9% Above List Price
    • $420/SF
    • 20 Days On Market

    Current Estimated Value $422,363

    Last Listing Agent Richard Froehlich RE/MAX Benchmark Realty Group

    40 Poplar Dr, Monroe, NY 10950
    • 38 Park Dr, Chester, NY 10918

      Est $615,593

      Not Listed For Sale

      38 Park Dr, Chester, NY 10918

      • 5 Beds
      • 3.5 Baths
      • 2,770 Sq Ft
      • Built 1968
      38 Park Dr, Chester, NY 10918

      Last Sold Summary

      • 28 Days On Market

  • L30 Lane Rd, Chester, NY 12853
    L30 Lane Rd, Chester, NY 12853
    L30 Lane Rd, Chester, NY 12853
    /5

    $35,000

    $12K PRICE DROP Pending
    • Land
    • 7.07 Acres
    • $4,950 per Acre

    L30 Lane Rd, Chester, NY 12853

    You won't want to miss out on this opportunity! A little over 7 acres (2 parcels) in the heart of the Adirondacks. Close proximity to all the local lakes (Schroon Lake, Loon Lake, Brant Lake) & 10 minutes from Gore Mountain.

    Julia Pucciarelli Gallo Realty ADK Inc

    L30 Lane Rd, Chester, NY 12853
  • 2409 Whispering Hills, Chester, NY 10918

    $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

    Current Estimated Value $367,309

    Last Listing Agent Linda Clark Hudson Valley Griffith

    2409 Whispering Hills, Chester, NY 10918
    • 77 Surrey Rd, Chester, NY 10918

      Est $572,683

      Not Listed For Sale

      77 Surrey Rd, Chester, NY 10918

      • 5 Beds
      • 2.5 Baths
      • 2,136 Sq Ft
      • Built 1968
      77 Surrey Rd, Chester, NY 10918

      Last Sold Summary

      • 43 Days On Market

  • 86 Carriage Knoll Rd, Chester, NY 12817
    86 Carriage Knoll Rd, Chester, NY 12817
    86 Carriage Knoll Rd, Chester, NY 12817
    /22

    $68,900

    $19K PRICE INCREASE
    • Land
    • 3.37 Acres
    • $20,445 per Acre

    86 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

    86 Carriage Knoll Rd, Chester, NY 12817
  • 22 Able Noble 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 $474,587

    Last Listing Agent Robin Kelly Picture It Sold, LLC

    22 Able Noble Dr, Chester, NY 10918
  • 1.3 Cobble Creek Rd Unit 3, Chester, NY 12853
    1.3 Cobble Creek Rd Unit 3, Chester, NY 12853
    1.3 Cobble Creek Rd Unit 3, Chester, NY 12853
    /10

    $119,995

    • Land
    • 30.95 Acres
    • $3,877 per Acre

    1.3 Cobble Creek Rd Unit 3, Chester, NY 12853

    Rarely does a property combine privacy, natural beauty and convenience as well as this 30-acre tract in Chester, New York. Located on a year-round town road, the land offers easy access while maintaining the peaceful feeling of a true Adirondack forest retreat. Several elevated APA-approved building sites are scattered throughout the property, offering ideal locations for an off-grid cabin or

    Marc Christmas CHRISTMAS AND ASSOCIATES INC

    1.3 Cobble Creek Rd Unit 3, Chester, NY 12853
  • 264 Heritage Ln, Monroe, NY 10950

    $350,000

    Sold Feb 02, 2026

    264 Heritage Ln, Monroe, NY 10950

    • 3 Beds
    • 1.5 Baths
    • 1,376 Sq Ft
    • Built 1988

    Last Sold Summary

    • $254/SF
    • 98 Days On Market

    Current Estimated Value $350,128

    Last Listing Agent Frank Golio Howard Hanna Rand Realty

    264 Heritage Ln, Monroe, NY 10950
  • 102 Beverly Rd, Chester, NY 10918
    102 Beverly Rd, Chester, NY 10918
    102 Beverly Rd, Chester, NY 10918
    /49

    $1,090,000

    • 4 Beds
    • 3.5 Baths
    • 4,130 Sq Ft

    102 Beverly Rd, Chester, NY 10918

    Located in the Warwick School district on a coveted street sits this larger than life home with impressive presence. The curved driveway welcomes you to the wide porch, perfect for rocking chairs and relaxing. The impressive entrance with custom stairway and window seat is just the first of impressive touches in this home. Large kitchen overlooks the yard and is well appointed with Thor

    Kimberly Corkum Keller Williams Realty

    102 Beverly Rd, Chester, NY 10918
  • 48 Brennan Ct, 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

    Current Estimated Value $754,182

    Last Listing Agent Claude Brischoux Keller Williams Realty

    48 Brennan Ct, Chester, NY 10918
    • 7 Park Dr, Chester, NY 10918

      Est $512,498

      Not Listed For Sale

      7 Park Dr, Chester, NY 10918

      • 4 Beds
      • 1.5 Baths
      • 1,760 Sq Ft
      • Built 1967
      7 Park Dr, Chester, NY 10918

      Last Sold Summary

      • 33 Days On Market

  • 195 Eagleton Dr, Monroe, NY 10950
    195 Eagleton Dr, Monroe, NY 10950
    195 Eagleton Dr, Monroe, NY 10950
    /26

    $394,900

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,762 Sq Ft

    195 Eagleton Dr, Monroe, NY 10950

    Beautifully maintained 3-bedroom, 2.5 bath home offering scenic lake views and a comfortable, well-designed layout. This home features stainless steel appliances, fireplace, hardwood floors and numerous recent updates throughout. Enjoy tranquil water views from the charming Juliette balcony perfect for morning coffee or relaxing evenings watching the sunset. Experience the ease of condo living

    Patricia Spagna Century 21 Realty Center

    195 Eagleton Dr, Monroe, NY 10950
  • L7 Macglashan Ln, Chester, NY 12817
    L7 Macglashan Ln, Chester, NY 12817
    L7 Macglashan Ln, Chester, NY 12817
    /31

    $55,000

    Sold May 12, 2026

    L7 Macglashan Ln, Chester, NY 12817

    • Land
    • 5.42 Acres
    • $10,148 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 130 Days On Market

    Current Estimated Value $39,000

    Last Listing Agent Walter Swartz Gallo Realty ADK Inc

    L7 Macglashan Ln, Chester, NY 12817
    • 15 Park Dr, Chester, NY 10918

      Est $470,965

      Not Listed For Sale

      15 Park Dr, Chester, NY 10918

      • 3 Beds
      • 2 Baths
      • 1,724 Sq Ft
      • Built 1968
      15 Park Dr, Chester, NY 10918

      Last Sold Summary

      • 41 Days On Market

  • 11 Oxford Depot, Chester, NY 10918
    11 Oxford Depot, Chester, NY 10918
    11 Oxford Depot, Chester, NY 10918
    /26

    $425,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,748 Sq Ft

    11 Oxford Depot, Chester, NY 10918

    Discover the charm and potential of 11 Oxford Depot Rd, Chester, NY — a spacious and inviting 3-bedroom, 2-bath home packed with character, versatility, and value. From the moment you enter, you’ll appreciate the warm hardwood floors, oversized living spaces, and flexible layout designed for today’s lifestyle. Whether you need a home office, playroom, guest room, or creative space, this home

    Aneudy Rosa Keller Williams Realty

    11 Oxford Depot, Chester, NY 10918

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