6,751

Chester, NY Homes

Section Image
    • 81 Hambletonian Ave, Chester, NY 10918

      Est $639,792

      Not Listed For Sale

      81 Hambletonian Ave, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,989 Sq Ft
      • Built 2001
      81 Hambletonian Ave, Chester, NY 10918

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Keith Sumner John J Lease REALTORS Inc

  • 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
  • 55 Beverly Rd, Chester, NY 10918

    $742,500

    Sold Jul 14, 2026

    55 Beverly Rd, Chester, NY 10918

    • 4 Beds
    • 3.5 Baths
    • 3,356 Sq Ft
    • Built 1993

    Last Sold Summary

    • 1% Above List Price
    • $221/SF
    • 48 Days On Market

    Current Estimated Value $735,954

    Last Listing Agent Jay Himelson Howard Hanna Rand Realty

    55 Beverly Rd, Chester, NY 10918
    • 7 Park Dr, Chester, NY 10918

      Est $517,596

      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

      Last Listing Agent Elena James Keller Williams Realty

  • 154 Eagleton Dr, Monroe, NY 10950
    154 Eagleton Dr, Monroe, NY 10950
    154 Eagleton Dr, Monroe, NY 10950
    /18

    $360,000

    Open Sun 11AM - 2PM
    • 3 Beds
    • 2.5 Baths
    • 1,585 Sq Ft

    154 Eagleton Dr, Monroe, NY 10950

    New Pics!Welcome to easy, low-maintenance living in this beautifully maintained 3-bedroom, 2.5-bath condo townhouse offering 1,585 square feet of comfortable living space in a peaceful community. Wake up to tranquil views overlooking a picturesque lake and enjoy the perfect blend of privacy, convenience, and amenities. The bright and spacious layout features central air conditioning, generous

    Bernadette Corrigan Keller Williams Realty

    154 Eagleton Dr, Monroe, NY 10950
  • 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 $514,316

    Last Listing Agent Jeanmarie Valentin HomeSmart Homes & Estates

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

      Est $467,262

      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

      Last Listing Agent Krista Fontenelle-Garcia Batiz Exit Realty DKC

  • 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
  • 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 $353,756

    Last Listing Agent Kewin Garabito eXp Realty

    2402 Whispering Hills Dr, Chester, NY 10918
    • 52 Surrey Rd, Chester, NY 10918

      Est $450,990

      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

      Last Listing Agent Brian Caplicki KW Hudson Valley United

  • 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 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 $496,874

    Last Listing Agent Jennifer Lucas Keller Williams Realty

    22 Bridle Ln, Chester, NY 10918
    • 22 Trotting Dr, Chester, NY 10918

      Est $397,700

      Not Listed For Sale

      22 Trotting Dr, Chester, NY 10918

      • 3 Beds
      • 1 Bath
      • 1,024 Sq Ft
      • Built 1968
      22 Trotting Dr, Chester, NY 10918

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Diane Blanton Howard Hanna Rand Realty

  • 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
  • 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 $604,900

    Last Listing Agent Rebecca Bank Keller Williams Realty

    15 Birch Dr, Monroe, NY 10950
    • 21 Park Dr, Chester, NY 10918

      Est $503,912

      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

      Last Listing Agent Colin Seitz RE/MAX Benchmark Realty Group

  • 5 Hilltop Ln, Chester, NY 10918
    5 Hilltop Ln, Chester, NY 10918
    5 Hilltop Ln, Chester, NY 10918
    /5

    $850,000

    • 5 Beds
    • 2.5 Baths
    • 3,200 Sq Ft

    5 Hilltop Ln, Chester, NY 10918

    Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new colonial-style residence invites you in with 12 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 kitchen. Every detail

    Moshe Kaufman MK Realty Inc

    5 Hilltop Ln, Chester, NY 10918
  • 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 $764,008

    Last Listing Agent Carmela Lopez Borrazas Serhant LLC

    1711 Kings Hwy, Chester, NY 10918
    • 27 Natures Trail, Chester, NY 10918

      Est $607,043

      Not Listed For Sale

      27 Natures Trail, Chester, NY 10918

      • 4 Beds
      • 2 Baths
      • 2,420 Sq Ft
      • Built 1966
      27 Natures Trail, Chester, NY 10918

      Last Sold Summary

      • 78 Days On Market

      Last Listing Agent Nikki Grzegorzewski Keller Williams Realty

  • 1 Hilltop Ln, Chester, NY 10918
    1 Hilltop Ln, Chester, NY 10918
    /2

    $750,000

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

    1 Hilltop Ln, 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

    Moshe Kaufman MK Realty Inc

    1 Hilltop Ln, 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
    • 2 Fields Ln, Chester, NY 10918

      Est $583,243

      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

      Last Listing Agent Margaret Galatro ARC Realty 1 in Sales

  • 102 Beverly Rd, Chester, NY 10918
    102 Beverly Rd, Chester, NY 10918
    102 Beverly Rd, Chester, NY 10918
    /49

    $1,090,000

    Pending
    • 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
  • 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 $310,515

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

    1503 Whispering Hills, Chester, NY 10918
    • 351 Sugarloaf Mountain Rd, Chester, NY 10918

      Est $538,227

      Not Listed For Sale

      351 Sugarloaf Mountain Rd, Chester, NY 10918

      • 3 Beds
      • 2 Baths
      • 1,562 Sq Ft
      • Built 1993
      351 Sugarloaf Mountain Rd, Chester, NY 10918

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Kasey Malone BHG Real Estate Green Team

  • 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
  • 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
    • 30 Lake Station Rd, Warwick, NY 10990

      Est $737,977

      Not Listed For Sale

      30 Lake Station Rd, Warwick, NY 10990

      • 2 Beds
      • 2 Baths
      • 1,720 Sq Ft
      • Built 1986
      30 Lake Station Rd, Warwick, NY 10990

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Carol Buchanan BHG Real Estate Green Team

  • 0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914
    0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914
    /2

    $1,700,000

    • Land
    • 46.5 Acres
    • $36,559 per Acre

    0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914

    Incredible opportunity to own approximately 55 acres of land being offered as a package with two adjoining parcels. This expansive property offers endless potential for investors, builders, or those seeking a private estate or recreational retreat. Preliminary information suggests the property may have the potential for approximately 400,000 square feet of warehouse space. Both parcels are being

    Lazar Schvimmer Mount Realty

    0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914
    • 110 Ridge Rd, Chester, NY 10918

      Est $991,541

      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

      Last Listing Agent Teresa Gavan BHG Real Estate Green Team

  • 107 Pine Hill Rd, Chester, NY 10918
    107 Pine Hill Rd, Chester, NY 10918
    107 Pine Hill Rd, Chester, NY 10918
    /33

    $549,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,730 Sq Ft

    107 Pine Hill Rd, Chester, NY 10918

    Something Special! See It and Fall in Love! A pavered walkway welcomes you to this curb appealing 3 BR, 2 1/2 bath Stucco Cape that is privately set on 1.1 acres! Open and sun filled with lots of windows! So many updates! Large primary BR and luxurious bath are on the 1 st floor! Open LR and DR have sliders to private deck to enjoy pastoral views and views of Sugar Loaf Mountain! 2 large BRs with

    Linda Clark Hudson Valley Griffith

    107 Pine Hill Rd, Chester, NY 10918
    • 392 Bellvale Rd, Chester, NY 10918

      Est $755,572

      Not Listed For Sale

      392 Bellvale Rd, Chester, NY 10918

      • 3 Beds
      • 2 Baths
      • 1,900 Sq Ft
      • Built 1993
      392 Bellvale Rd, Chester, NY 10918

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Mitchell Kass eXp Realty

  • 18 Fernglade Ct, Chester, NY 10918
    18 Fernglade Ct, Chester, NY 10918
    18 Fernglade Ct, Chester, NY 10918
    /50

    $650,000

    Pending
    • 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
    • 63 Hambletonian Rd, Chester, NY 10918

      Est $664,121

      Not Listed For Sale

      63 Hambletonian Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,310 Sq Ft
      • Built 1997
      63 Hambletonian Rd, Chester, NY 10918

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Dean Diltz Keller Williams Realty

  • 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
    • 73 Hambletonian Rd, Chester, NY 10918

      Est $600,176

      Not Listed For Sale

      73 Hambletonian Rd, Chester, NY 10918

      • 5 Beds
      • 2 Baths
      • 2,680 Sq Ft
      • Built 1948
      73 Hambletonian Rd, Chester, NY 10918

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Dean Diltz Keller Williams Realty

  • 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
    • 15 Banker Dr, Chester, NY 10918

      Est $789,998

      Not Listed For Sale

      15 Banker Dr, Chester, NY 10918

      • 4 Beds
      • 3.5 Baths
      • 2,396 Sq Ft
      • Built 2000
      15 Banker Dr, Chester, NY 10918

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Jennifer DiCostanzo RE/MAX Town & Country

  • 2007 Whispering Hills, Chester, NY 10918
    2007 Whispering Hills, Chester, NY 10918
    2007 Whispering Hills, Chester, NY 10918
    /44

    $279,999

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

    2007 Whispering Hills, Chester, NY 10918

    Welcome to 2007 Whispering Hills Drive! This 2-bedroom, 1.5-bath condo offers comfortable living in one of Chester’s most desirable communities. The main level features a spacious living room with a real wood-burning fireplace, a dining area, and a kitchen with stainless steel appliances. Luxury vinyl plank flooring adds a modern touch throughout the main living areas. Upstairs, you’ll find two

    Philip Szumlaski Keller Williams Realty

    2007 Whispering Hills, Chester, NY 10918
    • 1301 Kings Hwy, Chester, NY 10918

      Est $646,635

      Not Listed For Sale

      1301 Kings Hwy, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,676 Sq Ft
      • Built 1835
      1301 Kings Hwy, Chester, NY 10918

      Last Sold Summary

      • 146 Days On Market

      Last Listing Agent Susan Walski HomeSmart Homes & Estates

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