6,841

Chester, NY Homes

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  • 4503 Whispering Hills, Chester, NY 10918

    $330,000

    Sold Aug 15, 2025

    4503 Whispering Hills, Chester, NY 10918

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

    Last Sold Summary

    • 12% Below List Price
    • $248/SF
    • 142 Days On Market

    Current Estimated Value $343,222

    Last Listing Agent Richard Baxter Keller Williams Realty

    4503 Whispering Hills, Chester, NY 10918
  • 18 Fernglade Ct, Chester, NY 10918
    18 Fernglade Ct, Chester, NY 10918
    18 Fernglade Ct, Chester, NY 10918
    /50

    $650,000

    • 3 Beds
    • 2.5 Baths
    • 2,389 Sq Ft

    18 Fernglade Ct, Chester, NY 10918

    Welcome to this beautifully appointed Colonial that perfectly blends timeless design with modern living. Offering 3 generously sized bedrooms—including a spacious primary suite with a large walk-in closet and a spa-like ensuite bath featuring a soaking tub and separate 4-foot shower—this home delivers both comfort and style. A versatile bonus room provides the flexibility for a home office,

    Richard Froehlich RE/MAX Benchmark Realty Group

    18 Fernglade Ct, Chester, NY 10918
  • 4309 Whispering Hills Dr, Chester, NY 10918

    $375,000

    Sold Dec 11, 2025

    4309 Whispering Hills Dr, Chester, NY 10918

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

    Last Sold Summary

    • $277/SF
    • 27 Days On Market

    Current Estimated Value $374,951

    Last Listing Agent Sean Israelski Howard Hanna Rand Realty

    4309 Whispering Hills Dr, 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

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

    $76,900

    $14K PRICE INCREASE
    • Land
    • 5.1 Acres
    • $15,078 per Acre

    112 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

    112 Carriage Knoll Rd, Chester, NY 12817
  • 3120 Whispering Hills, Chester, NY 10918

    $299,000

    Sold Apr 07, 2026

    3120 Whispering Hills, Chester, NY 10918

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

    Last Sold Summary

    • 4% Below List Price
    • $279/SF
    • 70 Days On Market

    Current Estimated Value $301,689

    Last Listing Agent Bente Brown Hudson Premium Realty

    3120 Whispering Hills, Chester, NY 10918
    • 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

  • 2820 Whispering Hills, Chester, NY 10918
    2820 Whispering Hills, Chester, NY 10918
    2820 Whispering Hills, Chester, NY 10918
    /32

    $319,900

    $4K PRICE INCREASE Pending
    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft

    2820 Whispering Hills, Chester, NY 10918

    Lovely, Light and Airy 2 Bedroom 1 and 1/2 Bath Unit in Desireable Whispering Hills! Updated Kitchen and Bath, New Carpet and Freshly Painted. Downstairs has a Comfy Living Room with a Wood Burning Fireplace , Sunny Dining Room with Slider to a Patio, Convenient Galley Kitchen, Laundry Area and 1/2 Bath. Upstairs are a Spacious Primary Bedroom , Walkthrough Closet to Full Bath and a Roomy Second

    Anne Marie Scouarnec R2M Realty Inc.

    2820 Whispering Hills, Chester, NY 10918
  • L27 Carriage Knolls Rd, Chester, NY 12817
    L27 Carriage Knolls Rd, Chester, NY 12817
    L27 Carriage Knolls Rd, Chester, NY 12817
    /11

    $29,000

    Sold Nov 03, 2025

    L27 Carriage Knolls Rd, Chester, NY 12817

    • Land
    • 1.8 Acres
    • $16,111 per Acre

    Last Sold Summary

    • 71% Below List Price
    • 20 Days On Market

    Last Listing Agent Walter Swartz Gallo Realty ADK Inc

    L27 Carriage Knolls Rd, Chester, NY 12817
    • 52 Surrey Rd, Chester, NY 10918

      Est $448,674

      Not Listed For Sale

      52 Surrey Rd, Chester, NY 10918

      • 4 Beds
      • 2 Baths
      • 1,780 Sq Ft
      • Built 1969
      52 Surrey Rd, Chester, NY 10918

      Last Sold Summary

      • 104 Days On Market

  • 1367 Kings Hwy, Chester, NY 10918
    1367 Kings Hwy, Chester, NY 10918
    1367 Kings Hwy, Chester, NY 10918
    /13

    $460,000

    • 3 Beds
    • 1.5 Baths
    • 1,728 Sq Ft

    1367 Kings Hwy, Chester, NY 10918

    Historic Colonial Era Home in the Heart of Sugar Loaf, NYLocated just 60 minutes from NYCZoned Residential/CommercialStep into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Original building was built in 1770, this unique property features:• One

    Mark Karten Karten Real Estate Svcs LLC

    1367 Kings Hwy, Chester, NY 10918
  • 3915 Whispering Hills, Chester, NY 10918

    $382,000

    Sold Sep 29, 2025

    3915 Whispering Hills, Chester, NY 10918

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

    Last Sold Summary

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

    Current Estimated Value $384,721

    Last Listing Agent Kristie Jacques Century 21 Full Service Realty

    3915 Whispering Hills, Chester, NY 10918
  • 60 Carriage Knolls Rd, Chester, NY 12817
    60 Carriage Knolls Rd, Chester, NY 12817
    60 Carriage Knolls Rd, Chester, NY 12817
    /10

    $37,500

    • Land
    • 1.62 Acres
    • $23,148 per Acre

    60 Carriage Knolls Rd, Chester, NY 12817

    Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for

    Walter Swartz Gallo Realty ADK Inc

    60 Carriage Knolls Rd, Chester, NY 12817
  • 4501 Whispering Hills Dr, Chester, NY 10918

    $305,000

    Sold Aug 22, 2025

    4501 Whispering Hills Dr, Chester, NY 10918

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft
    • Built 1987

    Last Sold Summary

    • 9% Above List Price
    • $281/SF
    • 27 Days On Market

    Last Listing Agent Bernadette Giordano Howard Hanna Rand Realty

    4501 Whispering Hills Dr, Chester, NY 10918
    • 21 Park Dr, Chester, NY 10918

      Est $503,294

      Not Listed For Sale

      21 Park Dr, Chester, NY 10918

      • 4 Beds
      • 2 Baths
      • 1,800 Sq Ft
      • Built 1967
      21 Park Dr, Chester, NY 10918

      Last Sold Summary

      • 32 Days On Market

  • 2 Pine Hill Rd, Chester, NY 10918
    2 Pine Hill Rd, Chester, NY 10918
    2 Pine Hill Rd, Chester, NY 10918
    /36

    $875,000

    • 3 Beds
    • 2.5 Baths
    • 2,302 Sq Ft

    2 Pine Hill Rd, Chester, NY 10918

    The Conklin House: A Masterpiece of History & Modern Luxury. Experience the perfect blend of early 20th-century charm and 21st-century comfort. The Conklin House, a classic 1908 Queen Anne Victorian, stands as a commanding presence at the edge of the historic Village of Sugar Loaf. The home has always been used residentially but zoning permits commercial usage as well. Originally ordered from the

    Richard Ellis Ellis Sotheby's Intl Realty

    2 Pine Hill Rd, Chester, NY 10918
  • 6 Moffatt Ln, Chester, NY 10918

    $515,000

    Sold Dec 09, 2025

    6 Moffatt Ln, Chester, NY 10918

    • 5 Beds
    • 3 Baths
    • 1,888 Sq Ft
    • Built 1946

    Last Sold Summary

    • 3% Above List Price
    • $273/SF
    • 23 Days On Market

    Current Estimated Value $516,009

    Last Listing Agent Jeanmarie Valentin HomeSmart Homes & Estates

    6 Moffatt Ln, Chester, NY 10918
    • 18 Park Dr, Chester, NY 10918

      Est $485,326

      Not Listed For Sale

      18 Park Dr, Chester, NY 10918

      • 4 Beds
      • 1.5 Baths
      • 1,800 Sq Ft
      • Built 1967
      18 Park Dr, Chester, NY 10918

      Last Sold Summary

      • 24 Days On Market

  • 4 Debbie Ct, Chester, NY 10918
    4 Debbie Ct, Chester, NY 10918
    4 Debbie Ct, Chester, NY 10918
    /49

    $785,000

    $14K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 5,403 Sq Ft

    4 Debbie Ct, Chester, NY 10918

    Welcome to this exceptional private retreat nestled on beautifully landscaped grounds in desirable Chester. Offering the perfect blend of space, comfort, privacy, and lifestyle, this impressive property is surrounded by natural beauty while remaining conveniently close to shopping, dining, major highways, and the scenic Stewart State Forest. From the moment you arrive, you’ll appreciate the

    Joseph Rosenfeld Flag Realty Group

    4 Debbie Ct, Chester, NY 10918
  • 2402 Whispering Hills Dr, Chester, NY 10918

    $350,000

    Sold Aug 28, 2025

    2402 Whispering Hills Dr, Chester, NY 10918

    • 3 Beds
    • 2 Baths
    • 1,316 Sq Ft
    • Built 1987

    Last Sold Summary

    • 1% Above List Price
    • $266/SF
    • 23 Days On Market

    Current Estimated Value $356,794

    Last Listing Agent Kewin Garabito eXp Realty

    2402 Whispering Hills Dr, Chester, NY 10918
  • 18 Southside Dr, Monroe, NY 10950
    18 Southside Dr, Monroe, NY 10950
    18 Southside Dr, Monroe, NY 10950
    /36

    $495,000

    • 4 Beds
    • 3 Baths
    • 1,792 Sq Ft

    18 Southside Dr, Monroe, NY 10950

    Welcome to 18 Southside Drive, this charming ranch-style home nestled in the highly sought-after Walton Park neighborhood of Monroe. Offering the ultimate ease of effortless one level living, this spacious residence boasts 4 bedrooms, 3 full bathrooms, and a versatile layout situated within the premier Monroe-Woodbury School District. Major mechanical updates over the past decade provide ultimate

    Nikki Grzegorzewski Keller Williams Realty

    18 Southside Dr, Monroe, NY 10950
  • 22 Bridle Ln, Chester, NY 10918

    $498,000

    Sold Nov 21, 2025

    22 Bridle Ln, Chester, NY 10918

    • 4 Beds
    • 1.5 Baths
    • 1,570 Sq Ft
    • Built 1970

    Last Sold Summary

    • 2% Above List Price
    • $317/SF
    • 30 Days On Market

    Current Estimated Value $495,041

    Last Listing Agent Jennifer Lucas Keller Williams Realty

    22 Bridle Ln, Chester, NY 10918
    • 2 Fields Ln, Chester, NY 10918

      Est $573,257

      Not Listed For Sale

      2 Fields Ln, Chester, NY 10918

      • 3 Beds
      • 2.5 Baths
      • 2,604 Sq Ft
      • Built 1972
      2 Fields Ln, Chester, NY 10918

      Last Sold Summary

      • 24 Days On Market

  • L9 Byrd Pond, Chester, NY 12853
    L9 Byrd Pond, Chester, NY 12853
    L9 Byrd Pond, Chester, NY 12853
    /25

    $125,000

    • Land
    • 13.33 Acres
    • $9,377 per Acre

    L9 Byrd Pond, Chester, NY 12853

    Open walking trail around the property and very easy to navigate. Private 13+ acre building parcel just minutes from Gore Mountain and the conveniences of North Creek. The land is gently sloping with a roughed-in driveway/road already leading in from Bird Pond Road, offering a great head start for future access and site planning. Several attractive building locations can be found throughout the

    Walter Swartz Gallo Realty ADK Inc

    L9 Byrd Pond, Chester, NY 12853
  • 15 Birch Dr, Monroe, NY 10950

    $600,000

    Sold Aug 28, 2025

    15 Birch Dr, Monroe, NY 10950

    • 4 Beds
    • 2 Baths
    • 1,868 Sq Ft
    • Built 1971

    Last Sold Summary

    • 5% Above List Price
    • $321/SF
    • 23 Days On Market

    Current Estimated Value $592,687

    Last Listing Agent Rebecca Bank Keller Williams Realty

    15 Birch Dr, Monroe, NY 10950
    • 50 Ruth Ln, Chester, NY 10918

      Est $812,687

      Not Listed For Sale

      50 Ruth Ln, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,612 Sq Ft
      • Built 1995
      50 Ruth Ln, Chester, NY 10918

      Last Sold Summary

      • 24 Days On Market

  • 106 Carriage Knoll Rd, Chester, NY 12817
    106 Carriage Knoll Rd, Chester, NY 12817
    106 Carriage Knoll Rd, Chester, NY 12817
    /25

    $78,900

    $14K PRICE INCREASE
    • Land
    • 5.76 Acres
    • $13,698 per Acre

    106 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

    106 Carriage Knoll Rd, Chester, NY 12817
  • 1711 Kings Hwy, Chester, NY 10918

    $765,000

    Sold Sep 05, 2025

    1711 Kings Hwy, Chester, NY 10918

    • 3 Beds
    • 2 Baths
    • 2,020 Sq Ft
    • Built 1974

    Last Sold Summary

    • 2% Above List Price
    • $379/SF
    • 36 Days On Market

    Current Estimated Value $756,421

    Last Listing Agent Carmela Lopez Borrazas Serhant LLC

    1711 Kings Hwy, Chester, NY 10918
  • 558 Pine Hill Rd, Chester, NY 10918
    558 Pine Hill Rd, Chester, NY 10918
    558 Pine Hill Rd, Chester, NY 10918
    /50

    $599,000

    $251K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,120 Sq Ft

    558 Pine Hill Rd, Chester, NY 10918

    Beautifully spacious Colonial set on 1.8 private acres on Pine Hill Road, offering 3,120 square feet of rustic, updated charm behind a gated entry and surrounded by magnificent grounds. The main level welcomes you with a spacious eat-in kitchen that flows seamlessly into the dining area, creating an ideal setting for everyday living and effortless entertaining. The massively large living room

    Charnie Guttmann eRealty Advisors, Inc

    558 Pine Hill Rd, Chester, NY 10918
  • 102 Carriage Knoll Rd, Chester, NY 12817
    102 Carriage Knoll Rd, Chester, NY 12817
    102 Carriage Knoll Rd, Chester, NY 12817
    /24

    $70,000

    Sold Apr 24, 2026

    102 Carriage Knoll Rd, Chester, NY 12817

    • Land
    • 4.31 Acres
    • $16,241 per Acre

    Last Sold Summary

    • 25% Above List Price
    • 511 Days On Market

    Last Listing Agent Walter Swartz Gallo Realty ADK Inc

    102 Carriage Knoll Rd, Chester, NY 12817
  • 335 Laroe Rd, Chester, NY 10918
    335 Laroe Rd, Chester, NY 10918
    335 Laroe Rd, Chester, NY 10918
    /35

    $675,000

    Open Sun 11AM - 1PM $40K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,784 Sq Ft

    335 Laroe Rd, Chester, NY 10918

    Set on 3.2 acres within the Monroe-Woodbury School District, 335 Laroe Road offers a rare combination of space, functionality, and a convenient Chester location. Step inside to the welcoming two-story foyer featuring an open staircase and you'll immediately appreciate the size of the home. The main level offers a functional layout with multiple living spaces, including a living room, formal

    Christina D'Altilio Coldwell Banker Choice Prop.

    335 Laroe Rd, Chester, NY 10918
  • 1503 Whispering Hills, Chester, NY 10918

    $295,000

    Sold Jun 16, 2026

    1503 Whispering Hills, Chester, NY 10918

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

    Last Sold Summary

    • 13% Below List Price
    • $222/SF
    • 109 Days On Market

    Current Estimated Value $330,831

    Last Listing Agent Darlene Provino Century 21 E & M Williams Rlty

    1503 Whispering Hills, Chester, NY 10918
    • 110 Ridge Rd, Chester, NY 10918

      Est $990,251

      Not Listed For Sale

      110 Ridge Rd, Chester, NY 10918

      • 4 Beds
      • 3.5 Baths
      • 4,190 Sq Ft
      • Built 1995
      110 Ridge Rd, Chester, NY 10918

      Last Sold Summary

      • 24 Days On Market

  • 6 Adams Ct, Monroe, NY 10950
    6 Adams Ct, Monroe, NY 10950
    6 Adams Ct, Monroe, NY 10950
    /44

    $585,000

    $14K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,056 Sq Ft

    6 Adams Ct, Monroe, NY 10950

    Stunning Split Ranch with Pool and Gorgeous Curb Appeal, Located in the Town of Chester within the Monroe-Woodbury School District Welcome to this beautifully maintained 4-bedroom, 2 full bath split ranch offering the perfect blend of comfort, style, and functionality. The upper level features a spacious and sun-filled eat-in kitchen, ideal for everyday living, with direct access to a big Trex

    Ida Payne Keller Williams Realty

    6 Adams Ct, Monroe, NY 10950
  • L9 Atateka Rd, Chester, NY 12817
    L9 Atateka Rd, Chester, NY 12817
    L9 Atateka Rd, Chester, NY 12817
    /71

    $250,000

    Sold Apr 01, 2026

    L9 Atateka Rd, Chester, NY 12817

    • Land
    • 165.92 Acres
    • $1,507 per Acre

    Last Sold Summary

    • 24% Below List Price
    • 503 Days On Market

    Last Listing Agent John O'Donnell Timberland Realty

    L9 Atateka Rd, Chester, NY 12817

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