6,812

Chester, NY Homes

Section Image
    • 3976 Summerville Way, Chester, NY 10918

      Est $515,935 Not Listed For Sale

      3976 Summerville Way, Chester, NY 10918

      • 3 Beds
      • 1.5 Baths
      • 1,474 Sq Ft
      • Built 1955
      3976 Summerville Way, Chester, NY 10918

      Last Sold Summary

      • 2% Below List Price
      • $357/SF
      • 32 Days On Market

      Last Sold Price $526,000

      Last Listing Agent David Kraus MK Realty Inc

  • 607 Mountain Laurel Dr, Monroe, NY 10950
    607 Mountain Laurel Dr, Monroe, NY 10950
    607 Mountain Laurel Dr, Monroe, NY 10950
    /39

    $339,900

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

    607 Mountain Laurel Dr, Monroe, NY 10950

    Monroe-Woodbury Schools Townhouse with Low Taxes — Zoned for highly sought-after Pine Tree & Sapphire Elementary Schools. Step into this inviting 3-bedroom, 2.5-bath townhouse in the desirable Windridge community where space, light, and thoughtful updates come together. The spacious living room showcases younger laminate flooring that looks beautiful and cleans like a dream, while front-facing

    Rosalie Cook Weichert Realtors

    607 Mountain Laurel Dr, Monroe, NY 10950
  • 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
    • 3966 Summerville Way, Chester, NY 10918

      Est $656,000 Not Listed For Sale

      3966 Summerville Way, Chester, NY 10918

      • 5 Beds
      • 3 Baths
      • 2,882 Sq Ft
      • Built 1945
      3966 Summerville Way, Chester, NY 10918

      Last Sold Summary

      • 2% Below List Price
      • $232/SF
      • 6 Days On Market

      Last Sold Price $670,000

      Last Listing Agent Leon Klein Keller Williams Hudson Valley

  • 1221 Whispering Hills, Chester, NY 10918
    1221 Whispering Hills, Chester, NY 10918
    1221 Whispering Hills, Chester, NY 10918
    /31

    $397,000

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

    1221 Whispering Hills, Chester, NY 10918

    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 light, this home blends modern upgrades with functional design. Once you step inside, you will discover brand new

    Malia Leonard BUY NY REALTY LLC

    1221 Whispering Hills, Chester, NY 10918
  • 1301 Kings Hwy, Chester, NY 10918

    $617,000 Sold May 19, 2025

    1301 Kings Hwy, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,676 Sq Ft
    • Built 1835

    Last Sold Summary

    • 10% Below List Price
    • $231/SF
    • 146 Days On Market

    Current Estimated Value $610,245

    Last Listing Agent Susan Walski HomeSmart Homes & Estates

    1301 Kings Hwy, Chester, NY 10918
    • 1689 Kings Hwy, Chester, NY 10918

      Est $735,851 Not Listed For Sale

      1689 Kings Hwy, Chester, NY 10918

      • 3 Beds
      • 2.5 Baths
      • 2,682 Sq Ft
      • Built 1999
      1689 Kings Hwy, Chester, NY 10918

      Last Sold Summary

      • 11% Above List Price
      • $248/SF
      • 158 Days On Market

      Last Sold Price $665,000

      Last Listing Agent Rita Geissler ARC Realty 1 in Sales

  • 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

    • 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
  • 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 $522,909

    Last Listing Agent Claudia Lepore Keller Williams Realty

    219 Bull Mill Rd, Chester, NY 10918
    • 128 Booth Rd, Chester, NY 10918

      Est $558,347 Not Listed For Sale

      128 Booth Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,102 Sq Ft
      • Built 1975
      128 Booth Rd, Chester, NY 10918

      Last Sold Summary

      • 2% Above List Price
      • $259/SF
      • 179 Days On Market

      Last Sold Price $545,000

      Last Listing Agent Tracy McNamara Keller Williams Realty

  • 651 Lakes Rd, Monroe, NY 10950
    651 Lakes Rd, Monroe, NY 10950
    651 Lakes Rd, Monroe, NY 10950
    /7

    $874,400

    • 4 Beds
    • 2 Baths
    • 2,466 Sq Ft

    651 Lakes Rd, Monroe, NY 10950

    Rare opportunity to purchase this gorgeous property that consists of 3 homes nestled on 3.5 beautiful acres. The main Colonial residence has been gutted and will need to be renovated/rebuilt, however, you can live in one of the additional two residences while you renovate! The 2nd residence called the “stone cottage” has 2 fieldstone fireplaces, a full kitchen, a vaulted ceiling in the bedroom, a

    Frank Golio Howard Hanna Rand Realty

    651 Lakes Rd, Monroe, NY 10950
  • 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 $416,628

    Last Listing Agent Joel Ayala HomeSmart Homes & Estates

    354 Rande Rd Unit 354, Monroe, NY 10950
    • 272 Bull Mill Rd, Chester, NY 10918

      Est $684,170 Not Listed For Sale

      272 Bull Mill Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,504 Sq Ft
      • Built 1998
      272 Bull Mill Rd, Chester, NY 10918

      Last Sold Summary

      • 14% Above List Price
      • $240/SF
      • 50 Days On Market

      Last Sold Price $600,000

      Last Listing Agent Joseph Rosenfeld Flag Realty Group

  • L9 Bird Pond Rd, Chester, NY 12853
    L9 Bird Pond Rd, Chester, NY 12853
    L9 Bird Pond Rd, Chester, NY 12853
    /27

    $129,000

    • Land
    • 13.33 Acres
    • $9,677 per Acre

    L9 Bird Pond Rd, Chester, NY 12853

    Private 13+ acres of gently sloping land just minutes from Gore Mountain. Roughed-in driveway/Road leading from Bird Pond Rd. Several nice building locations around the property. One house-site staked-out for reference. Possible views from higher on the property with some select clearing. Listing agent will provide one set of existing preliminary building plans for the future homeowner from

    Walter Swartz Gallo Realty ADK Inc

    L9 Bird Pond Rd, Chester, NY 12853
  • 3 Woodridge Dr, Chester, NY 10918

    $763,750 Sold Jun 20, 2025

    3 Woodridge Dr, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft
    • Built 1995

    Last Sold Summary

    • 4% Below List Price
    • $306/SF
    • 69 Days On Market

    Current Estimated Value $734,866

    Last Listing Agent Gina Dudgeon Howard Hanna Rand Realty

    3 Woodridge Dr, Chester, NY 10918
    • 71 Winding Trail, Chester, NY 10918

      Est $684,424 Not Listed For Sale

      71 Winding Trail, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,800 Sq Ft
      • Built 1987
      71 Winding Trail, Chester, NY 10918

      Last Sold Summary

      • 2% Above List Price
      • $239/SF
      • 10 Days On Market

      Last Sold Price $670,000

      Last Listing Agent Frank Muccari Cronin & Company Real Estate

  • 53 Odyssey Dr, Chester, NY 10918
    53 Odyssey Dr, Chester, NY 10918
    53 Odyssey Dr, Chester, NY 10918
    /48

    $1,100,000

    • 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
  • 19 Taurus Ave, Monroe, NY 10950

    $389,000 Sold Jul 09, 2025

    19 Taurus Ave, Monroe, NY 10950

    • 3 Beds
    • 1.5 Baths
    • 1,288 Sq Ft
    • Built 1954

    Last Sold Summary

    • 4% Above List Price
    • $302/SF
    • 30 Days On Market

    Current Estimated Value $381,811

    Last Listing Agent Christian Baez Keller Williams Hudson Valley

    19 Taurus Ave, Monroe, NY 10950
    • 11 Park Place, Chester, NY 10918

      Est $769,983 Not Listed For Sale

      11 Park Place, Chester, NY 10918

      • 5 Beds
      • 3.5 Baths
      • 2,923 Sq Ft
      • Built 1996
      11 Park Place, Chester, NY 10918

      Last Sold Summary

      • 10% Above List Price
      • $239/SF
      • 23 Days On Market

      Last Sold Price $700,000

      Last Listing Agent Jennifer Connolly BHHS Gross & Jansen

  • 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
  • 116 Carriage Knoll Rd, Chester, NY 12817
    116 Carriage Knoll Rd, Chester, NY 12817
    116 Carriage Knoll Rd, Chester, NY 12817
    /16

    $60,000 Sold Jun 12, 2025

    116 Carriage Knoll Rd, Chester, NY 12817

    • Land
    • 5.34 Acres
    • $11,236 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 30 Days On Market

    Last Listing Agent Walter Swartz Gallo Realty ADK Inc

    116 Carriage Knoll Rd, Chester, NY 12817
    • 2 Park Place, Chester, NY 10918

      Est $874,367 Not Listed For Sale

      2 Park Place, Chester, NY 10918

      • 4 Beds
      • 4.5 Baths
      • 4,492 Sq Ft
      • Built 1999
      2 Park Place, Chester, NY 10918

      Last Sold Summary

      • 11% Above List Price
      • $176/SF
      • 97 Days On Market

      Last Sold Price $789,000

      Last Listing Agent Claudia Lepore Keller Williams Realty

  • 111 Lake Region Blvd, Monroe, NY 10950
    111 Lake Region Blvd, Monroe, NY 10950
    111 Lake Region Blvd, Monroe, NY 10950
    /22

    $309,900 Pending

    • 2 Beds
    • 1 Bath
    • 792 Sq Ft

    111 Lake Region Blvd, Monroe, NY 10950

    Charming 2BR/1BA ranch on a level lot featuring an oversized detached 2-car garage and rear deck. Bright eat-in kitchen with ample cabinetry and vinyl plank flooring. Rear deck overlooks a spacious, usable yard—ideal for outdoor enjoyment. Convenient location close to shopping, schools, and major commuter routes. Great opportunity for owner-occupants or investors alike.

    Donna Ramundo Keller Williams Valley Realty

    111 Lake Region Blvd, Monroe, NY 10950
  • 101 Mountain Laurel Dr Unit 1A, Monroe, NY 10950

    $285,000 Sold Mar 31, 2025

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

    • 2 Beds
    • 2.5 Baths
    • 1,344 Sq Ft
    • Built 1979

    Last Sold Summary

    • $212/SF
    • 57 Days On Market

    Current Estimated Value $290,065

    Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

    101 Mountain Laurel Dr Unit 1A, Monroe, NY 10950
    • 243 Bull Mill Rd, Chester, NY 10918

      Est $632,170 Not Listed For Sale

      243 Bull Mill Rd, Chester, NY 10918

      • 3 Beds
      • 2.5 Baths
      • 2,021 Sq Ft
      • Built 1985
      243 Bull Mill Rd, Chester, NY 10918

      Last Sold Summary

      • 5% Above List Price
      • $297/SF
      • 11 Days On Market

      Last Sold Price $600,000

      Last Listing Agent Debra gay Coldwell Banker Realty

  • 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
  • 507 Bull Mill Rd, Chester, NY 10918

    $675,000 Sold Feb 18, 2026

    507 Bull Mill Rd, Chester, NY 10918

    • 5 Beds
    • 2.5 Baths
    • 3,115 Sq Ft
    • Built 2003

    Last Sold Summary

    • 4% Below List Price
    • $217/SF
    • 134 Days On Market

    Current Estimated Value $692,576

    Last Listing Agent Alison Orlando Keller Williams Hudson Valley

    507 Bull Mill Rd, Chester, NY 10918
    • 119 Booth Rd, Chester, NY 10918

      Est $545,426 Not Listed For Sale

      119 Booth Rd, Chester, NY 10918

      • 3 Beds
      • 2.5 Baths
      • 1,944 Sq Ft
      • Built 1976
      119 Booth Rd, Chester, NY 10918

      Last Sold Summary

      • 4% Above List Price
      • $270/SF
      • 39 Days On Market

      Last Sold Price $525,000

      Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

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

    $500,000 Pending

    • Land
    • 0.83 Acre
    • $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
  • 3 Grant Dr, Monroe, NY 10950

    $530,000 Sold May 19, 2025

    3 Grant Dr, Monroe, NY 10950

    • 3 Beds
    • 2 Baths
    • 1,932 Sq Ft
    • Built 1989

    Last Sold Summary

    • 6% Above List Price
    • $274/SF
    • 21 Days On Market

    Current Estimated Value $548,832

    Last Listing Agent Rosalie Cook Weichert Realtors

    3 Grant Dr, Monroe, NY 10950
    • 6 Reilly Rd, Chester, NY 10918

      Est $596,650 Not Listed For Sale

      6 Reilly Rd, Chester, NY 10918

      • 3 Beds
      • 3 Baths
      • 2,130 Sq Ft
      • Built 1976
      6 Reilly Rd, Chester, NY 10918

      Last Sold Summary

      • 13% Above List Price
      • $249/SF
      • 102 Days On Market

      Last Sold Price $530,000

      Last Listing Agent Jian Gonzalez RE/MAX Opulent

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

    $349,999

    • 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
  • 46 Brookview Dr, Monroe, NY 10950

    $869,000 Sold May 05, 2025

    46 Brookview Dr, Monroe, NY 10950

    • 5 Beds
    • 5 Baths
    • 4,200 Sq Ft
    • Built 1993

    Last Sold Summary

    • 3% Below List Price
    • $207/SF
    • 146 Days On Market

    Current Estimated Value $927,205

    Last Listing Agent David White Owner Entry.com

    46 Brookview Dr, Monroe, NY 10950
    • 61 Nancy Ln, Chester, NY 10918

      Est $721,637 Not Listed For Sale

      61 Nancy Ln, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,700 Sq Ft
      • Built 2002
      61 Nancy Ln, Chester, NY 10918

      Last Sold Summary

      • 11% Above List Price
      • $241/SF
      • 35 Days On Market

      Last Sold Price $650,000

      Last Listing Agent Martha Randazzo Howard Hanna Rand Realty

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

    $149,900

    • Land
    • 0.2 Acre
    • $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
  • 10 Spectrum Dr, Chester, NY 10918

    $800,000 Sold Sep 15, 2025

    10 Spectrum Dr, Chester, NY 10918

    • 5 Beds
    • 4 Baths
    • 4,496 Sq Ft
    • Built 1991

    Last Sold Summary

    • 11% Below List Price
    • $178/SF
    • 24 Days On Market

    Current Estimated Value $804,431

    Last Listing Agent David Hopstein eRealty Advisors, Inc

    10 Spectrum Dr, Chester, NY 10918
    • 88 Nancy Ln, Chester, NY 10918

      Est $611,728 Not Listed For Sale

      88 Nancy Ln, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,768 Sq Ft
      • Built 1992
      88 Nancy Ln, Chester, NY 10918

      Last Sold Summary

      • 11% Above List Price
      • $199/SF
      • 44 Days On Market

      Last Sold Price $549,675

      Last Listing Agent Christopher Rose REALHome Services & Solutions

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

    $68,900

    • 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
  • 142 Laroe Rd, Chester, NY 10918

    $607,700 Sold Apr 29, 2025

    142 Laroe Rd, Chester, NY 10918

    • 5 Beds
    • 3.5 Baths
    • 3,385 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Below List Price
    • $180/SF
    • 107 Days On Market

    Current Estimated Value $636,707

    Last Listing Agent Peter Persaud HomeSmart Homes & Estates

    142 Laroe Rd, Chester, NY 10918
    • 38 Rebecca Rd, Chester, NY 10918

      Est $575,833 Not Listed For Sale

      38 Rebecca Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 1,910 Sq Ft
      • Built 1990
      38 Rebecca Rd, Chester, NY 10918

      Last Sold Summary

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

      Last Sold Price $555,000

      Last Listing Agent Steve Esposito HomeSmart Homes & Estates

Showing Results 121 - 160, Page 4 of 18

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