6,841

Chester, NY Homes

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  • L1.34 McPhillips Pine Ln, Chester, NY 12817
    L1.34 McPhillips Pine Ln, Chester, NY 12817
    L1.34 McPhillips Pine Ln, Chester, NY 12817
    /9

    $275,000

    • Land
    • 7.53 Acres
    • $36,521 per Acre

    L1.34 McPhillips Pine Ln, Chester, NY 12817

    If you are looking for an ultra private lot with access (dock and beach rights) to one of the pristine exclusive lakes in the Adirondacks, you found it. Friends Lake is the home to cool people and is private, jet-ski free, with a water ski course and simply no nonsense. Only 2O minutes to Lake George and Gore Mountain Ski Area. About 4 hours from NYC and 2.5 hours to Montreal. Saratoga Springs is

    Michael Lynch Coldwell Banker Prime Properties

    L1.34 McPhillips Pine Ln, Chester, NY 12817
  • 6 E Shore Dr, Chester, NY 12817
    6 E Shore Dr, Chester, NY 12817
    /2

    $75,000

    Sold Nov 10, 2025

    6 E Shore Dr, Chester, NY 12817

    • Land
    • 29,185 Sq Ft
    • $111,940 per Acre

    Last Sold Summary

    • 36% Above List Price
    • 5 Days On Market

    Current Estimated Value $218,000

    Last Listing Agent Michelle Decoteau KW Platform

    6 E Shore Dr, Chester, NY 12817
  • 1221 Whispering Hills, Chester, NY 10918
    1221 Whispering Hills, Chester, NY 10918
    1221 Whispering Hills, Chester, NY 10918
    /35

    $377,000

    $20K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft

    1221 Whispering Hills, Chester, NY 10918

    Update: Last buyers financing fell through so this wonderful property can be yours!! This is a must see! Will not last! Welcome to this beautifully renovated, spacious 3-bedroom, 2.5-bathroom, end-unit condo offering privacy, comfort, and elevated living in the desirable Whispering Hills community in picturesque Chester, NY! Perfectly positioned at the end of the row for added privacy and natural

    Malia Leonard BUY NY REALTY LLC

    1221 Whispering Hills, Chester, NY 10918
  • 1 Hillview Terrace, Chester, NY 10918
    1 Hillview Terrace, Chester, NY 10918
    1 Hillview Terrace, Chester, NY 10918
    /3

    $710,000

    Sold Feb 24, 2026

    1 Hillview Terrace, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • Built 1997

    Last Sold Summary

    • $355/SF
    • 21 Days On Market

    Current Estimated Value $711,512

    Last Listing Agent Sandra Cassio Robert DeFalco Realty, Inc.

    1 Hillview Terrace, Chester, NY 10918
  • L 13.2 Friends Lake Rd, Chester, NY 12817
    L 13.2 Friends Lake Rd, Chester, NY 12817
    L 13.2 Friends Lake Rd, Chester, NY 12817
    /78

    $699,900

    $140K PRICE DROP
    • Land
    • 337 Acres
    • $2,077 per Acre

    L 13.2 Friends Lake Rd, Chester, NY 12817

    2,200 feet of frontage along the Upper Hudson River, a wild, whitewater backcountry river, and immediate access to nearly 1,600 acres of State Forest Preserve, the Hudson River Woods & Wildwater property is the ''complete package'' of Adirondack property. With over 4,500 feet of road frontage (with electric) on Friends Lake Road, it's an ideal location for a camp, second home, or subdivision.

    John O'Donnell Timberland Realty

    L 13.2 Friends Lake Rd, Chester, NY 12817
  • 3107 Whispering Hills, Chester, NY 10918

    $310,000

    Sold Dec 10, 2025

    3107 Whispering Hills, Chester, NY 10918

    • 2 Beds
    • 1.5 Baths
    • 1,086 Sq Ft
    • Built 1987

    Last Sold Summary

    • 5% Below List Price
    • $285/SF
    • 143 Days On Market

    Current Estimated Value $312,160

    Last Listing Agent Hershel Lowy Master Realty Group Inc.

    3107 Whispering Hills, Chester, NY 10918
  • 53 Odyssey Dr, Chester, NY 10918
    53 Odyssey Dr, Chester, NY 10918
    53 Odyssey Dr, Chester, NY 10918
    /48

    $1,100,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 4,467 Sq Ft

    53 Odyssey Dr, Chester, NY 10918

    Welcome to an extraordinary 4,400+ square foot residence in the coveted Warwick School district, where luxury and lifestyle converge to create the ultimate entertainer’s dream. This meticulously maintained and thoughtfully updated home offers breathtaking panoramic views, inviting you to unwind in the serene front atrium or the sun-drenched sunroom at the rear. Step inside to discover a

    Hilary Ryan Goldman Howard Hanna Rand Realty

    53 Odyssey Dr, Chester, NY 10918
  • 138 Dug Rd, Chester, NY 10918

    $700,000

    Sold Jul 08, 2025

    138 Dug Rd, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,452 Sq Ft
    • Built 1974

    Last Sold Summary

    • $285/SF
    • 49 Days On Market

    Current Estimated Value $693,564

    Last Listing Agent Jake Garay Serhant LLC

    138 Dug Rd, Chester, NY 10918
    • 465 Meri Ln, Monroe, NY 10950

      Est $419,879

      Not Listed For Sale

      465 Meri Ln, Monroe, NY 10950

      • 3 Beds
      • 2.5 Baths
      • 1,694 Sq Ft
      • Built 2001
      465 Meri Ln, Monroe, NY 10950

      Last Sold Summary

      • 55 Days On Market

  • 220 Oxford Rd, Chester, NY 10918
    220 Oxford Rd, Chester, NY 10918
    220 Oxford Rd, Chester, NY 10918
    /3

    $899,000

    $100K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,535 Sq Ft

    220 Oxford Rd, Chester, NY 10918

    220 Oxford Road is a Truly Impressive Property! Offering over 3,500 sq ft of beautifully maintained living space, this home features 3 bedrooms plus an additional upper-level room, 3 full baths, and 1 half bath. Spacious living room, stunning family room, and a practical, well-designed kitchen. The home showcases elegant finishes throughout along with brand new flooring that adds a fresh modern

    Moche Halpern Blooming Realty

    220 Oxford Rd, Chester, NY 10918
  • 165 Creamery Pond Rd, Chester, NY 10918

    $675,000

    Sold Nov 18, 2025

    165 Creamery Pond Rd, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,548 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Below List Price
    • $265/SF
    • 55 Days On Market

    Current Estimated Value $688,913

    Last Listing Agent Kichka Pascaru Christie's Int. Real Estate

    165 Creamery Pond Rd, Chester, NY 10918
    • 463 Meri Ln, Monroe, NY 10950

      Est $399,074

      Not Listed For Sale

      463 Meri Ln, Monroe, NY 10950

      • 3 Beds
      • 2.5 Baths
      • 1,694 Sq Ft
      • Built 2001
      463 Meri Ln, Monroe, NY 10950

      Last Sold Summary

      • 34 Days On Market

  • 4 Greycourt Rd, Chester, NY 10918
    4 Greycourt Rd, Chester, NY 10918
    4 Greycourt Rd, Chester, NY 10918
    /20

    $599,000

    Pending
    • 3 Beds
    • 1.5 Baths

    4 Greycourt Rd, Chester, NY 10918

    Magnificent sprawling ranch situated on a park like setting with 2.80 acres with mature landscaping. This home features a spacious 2014 renovated EIK for entertaining with soft close cabinets, granite countertops, stainless steel appliances and an island cook top. Kitchen leads to an open concept large living /dining room combo with a large bay window for natural light with newly refinished

    Scott Loyer Coldwell Banker American Homes

    4 Greycourt Rd, Chester, NY 10918
  • 2816 Whispering Hills, Chester, NY 10918

    $350,000

    Sold Jul 28, 2025

    2816 Whispering Hills, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft
    • Built 1984

    Last Sold Summary

    • $263/SF
    • 23 Days On Market

    Current Estimated Value $359,520

    Last Listing Agent Bernadette Giordano Howard Hanna Rand Realty

    2816 Whispering Hills, Chester, NY 10918
  • 94 Booth Rd, Chester, NY 10918
    94 Booth Rd, Chester, NY 10918
    94 Booth Rd, Chester, NY 10918
    /23

    $550,000

    $40K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,083 Sq Ft

    94 Booth Rd, Chester, NY 10918

    94 Booth Road represents a rare find in the current Chester market, offering an exceptional balance of space and value on a sprawling 1.84-acre lot. Positioned at the end of a quiet cul-de-sac that borders protected state parkland, this property provides a unique sense of seclusion and a lasting connection to the natural landscape. Inside, the residence spans 2,083 square feet of thoughtfully

    Craig Watters Compass Greater NY, LLC

    94 Booth Rd, Chester, NY 10918
  • 4706 Whispering Hills, Chester, NY 10918

    $310,000

    Sold Jul 21, 2025

    4706 Whispering Hills, Chester, NY 10918

    • 2 Beds
    • 1.5 Baths
    • 1,086 Sq Ft
    • Built 1987

    Last Sold Summary

    • 2% Above List Price
    • $285/SF
    • 18 Days On Market

    Current Estimated Value $315,382

    Last Listing Agent Jessica Evans KW Hudson Valley United

    4706 Whispering Hills, Chester, NY 10918
    • 51 Pewter Cir, Chester, NY 10918

      Est $570,362

      Not Listed For Sale

      51 Pewter Cir, Chester, NY 10918

      • 3 Beds
      • 3.5 Baths
      • 2,623 Sq Ft
      • Built 2007
      51 Pewter Cir, Chester, NY 10918

      Last Sold Summary

      • 67 Days On Market

  • 32 Poplar Dr, Monroe, NY 10950
    32 Poplar Dr, Monroe, NY 10950
    32 Poplar Dr, Monroe, NY 10950
    /20

    $525,000

    Pending
    • 4 Beds
    • 1.5 Baths
    • 1,792 Sq Ft

    32 Poplar Dr, Monroe, NY 10950

    GREAT house! If you are looking for move in ready this is IT!!! New kitchen and baths! Either new floors or redone hardwood. Freshly painted. Beautiful paver walkway! New Boiler 2023, Water Heater 2023, Ductless 2022, Roof 10 years old.

    Ann Marie Hahr Keller Williams Realty

    32 Poplar Dr, Monroe, NY 10950
  • 10 El Dorado Trail, Chester, NY 10918

    $265,000

    Sold Jul 11, 2025

    10 El Dorado Trail, Chester, NY 10918

    • Land
    • 6.3 Acres
    • $42,063 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 152 Days On Market

    Current Estimated Value $262,546

    Last Listing Agent Lisandra Rivera Keller Williams Realty

    10 El Dorado Trail, Chester, NY 10918
    • 53 Pewter Cir, Chester, NY 10918

      Est $604,631

      Not Listed For Sale

      53 Pewter Cir, Chester, NY 10918

      • 3 Beds
      • 2.5 Baths
      • 2,210 Sq Ft
      • Built 2007
      53 Pewter Cir, Chester, NY 10918

      Last Sold Summary

      • 33 Days On Market

  • 0 Main St, Chester, NY 10918
    0 Main St, Chester, NY 10918
    /2

    $500,000

    Pending
    • Land
    • 36,098 Sq Ft
    • $603,355 per Acre

    0 Main St, Chester, NY 10918

    Open commercial lot directly behind the existing Cumberland Farms and just to the east of the former Brookside carwash. Good use may be for a parking lot for a building built on 42 Brookside.

    Claude Brischoux Keller Williams Realty

    0 Main St, Chester, NY 10918
  • 451 Meri Ln, Monroe, NY 10950

    $429,000

    Sold Feb 06, 2026

    451 Meri Ln, Monroe, NY 10950

    • 3 Beds
    • 3.5 Baths
    • 1,698 Sq Ft
    • Built 2001

    Last Sold Summary

    • 8% Above List Price
    • $253/SF
    • 20 Days On Market

    Current Estimated Value $423,450

    Last Listing Agent Gary Silberstein Keller Williams Valley Realty

    451 Meri Ln, Monroe, NY 10950
    • 15 Pewter Cir, Chester, NY 10918

      Est $722,973

      Not Listed For Sale

      15 Pewter Cir, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 3,223 Sq Ft
      • Built 1999
      15 Pewter Cir, Chester, NY 10918

      Last Sold Summary

      • 218 Days On Market

  • 149 Creamery Pond Rd, Chester, NY 10918
    149 Creamery Pond Rd, Chester, NY 10918
    149 Creamery Pond Rd, Chester, NY 10918
    /46

    $825,000

    Open Sat 1PM - 4PM $63K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,740 Sq Ft

    149 Creamery Pond Rd, Chester, NY 10918

    Welcome to the highly sought-after Creamery Estate, located in the award-winning Warwick school district!. This inviting waterfront Colonial-style home offers the perfect blend of comfort, charm, and scenic beauty, set on an acre of beautifully maintained grounds with peaceful views of Creamery Pond. This 3-bedroom, 3 full bath home features hardwood floors throughout and a spacious, easy-flow

    Carla Terranova Keller Williams Realty

    149 Creamery Pond Rd, Chester, NY 10918
  • 92 Pickerel Rd, Monroe, NY 10950

    $560,000

    Sold Jul 01, 2025

    92 Pickerel Rd, Monroe, NY 10950

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft
    • Built 1969

    Last Sold Summary

    • 2% Below List Price
    • $278/SF
    • 148 Days On Market

    Current Estimated Value $568,651

    Last Listing Agent Richard Wawrynek Howard Hanna Rand Realty

    92 Pickerel Rd, Monroe, NY 10950
    • 11 Pewter Cir, Chester, NY 10918

      Est $595,786

      Not Listed For Sale

      11 Pewter Cir, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,156 Sq Ft
      • Built 1999
      11 Pewter Cir, Chester, NY 10918

      Last Sold Summary

      • 102 Days On Market

  • 8 Camelback Rd, Chester, NY 10918
    8 Camelback Rd, Chester, NY 10918
    8 Camelback Rd, Chester, NY 10918
    /11

    $349,999

    $25K PRICE DROP Pending
    • Land
    • 4.9 Acres
    • $71,428 per Acre

    8 Camelback Rd, Chester, NY 10918

    Nestled at the end of a private cul-de-sac, this 5 acre homesite offers breathtaking mountain and valley views in the sought-after Bull Mill Road area of Monroe/Chester, NY. The property’s gentle slopes create the perfect opportunity for a walkout lower level, allowing you to capture spectacular sunsets. This shovel-ready, fully approved, and engineered building lot features Belgian block

    James Feldhaus eXp Realty

    8 Camelback Rd, Chester, NY 10918
  • 18 Oakland Ave, Chester, NY 10918

    $369,900

    Sold Jan 22, 2026

    18 Oakland Ave, Chester, NY 10918

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft
    • Built 1955

    Last Sold Summary

    • $341/SF
    • 24 Days On Market

    Current Estimated Value $372,973

    Last Listing Agent Claude Brischoux Keller Williams Realty

    18 Oakland Ave, Chester, NY 10918
    • 16 Pewter Cir, Chester, NY 10918

      Est $701,856

      Not Listed For Sale

      16 Pewter Cir, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,849 Sq Ft
      • Built 1998
      16 Pewter Cir, Chester, NY 10918

      Last Sold Summary

      • 60 Days On Market

  • 2 Imperial Park, Chester, NY 10918
    2 Imperial Park, Chester, NY 10918
    2 Imperial Park, Chester, NY 10918
    /9

    $149,900

    Pending
    • Land
    • 8,873 Sq Ft
    • $735,886 per Acre

    2 Imperial Park, Chester, NY 10918

    Large 2 story storage barn approx 80' x 30' with silo for sale in the Town of Chester. 5 garage doors - 4 are 6 feet high, 1 door is 7 foot high with loading dock. Plenty of storage on first and second level. Small office. Has electric, but is turned off. Has well water, but no septic - lot is too small - only .20 acre. Not a buildable lot. Barn was subdivided off from neighboring farm. Has loft

    William Scolza HomeSmart Homes & Estates

    2 Imperial Park, Chester, NY 10918
  • 13 Dewey Rd, Chester, NY 12860
    13 Dewey Rd, Chester, NY 12860
    13 Dewey Rd, Chester, NY 12860
    /40

    $320,000

    Sold Oct 03, 2025

    13 Dewey Rd, Chester, NY 12860

    • 2 Beds
    • 1 Bath
    • 1,155 Sq Ft
    • Built 2004

    Last Sold Summary

    • 10% Below List Price
    • $277/SF
    • 92 Days On Market

    Current Estimated Value $314,650

    Last Listing Agent James Nester Cork Nester's True North Prop

    13 Dewey Rd, Chester, NY 12860
  • 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
  • L1.1 Elk Glade Rd, Chester, NY 12817
    L1.1 Elk Glade Rd, Chester, NY 12817
    L1.1 Elk Glade Rd, Chester, NY 12817
    /8

    $110,000

    Sold Dec 18, 2025

    L1.1 Elk Glade Rd, Chester, NY 12817

    • Land
    • 1.24 Acres
    • $88,710 per Acre

    Last Sold Summary

    • 5 Days On Market

    Last Listing Agent Saraha Millington Gallo Realty ADK Inc

    L1.1 Elk Glade Rd, Chester, NY 12817
  • 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

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