6,751

Chester, NY Homes

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  • 241 Meadow Ave, Chester, NY 10918
    241 Meadow Ave, Chester, NY 10918
    241 Meadow Ave, Chester, NY 10918
    /35

    $399,999

    Pre-Foreclosure
    • 4 Beds
    • 1.5 Baths
    • 1,560 Sq Ft

    241 Meadow Ave, Chester, NY 10918

    Discover the timeless charm and endless potential of this classic Colonial farmhouse, ideally situated on just under one level acre in the heart of Chester, NY. Offering approximately 1,560 square feet of living space, this 4 bedroom, 2 bath home is filled with character and craftsmanship.Step inside to find original hardwood floors, a cozy wood-burning stove, and an artistic, welcoming

    Agent Photo

    Chativa Bowen

    Keller Williams Realty

    241 Meadow Ave, Chester, NY 10918
  • 12 Bianca Blvd, Chester, NY 10918

    $575,000

    Sold Sep 23, 2025

    12 Bianca Blvd, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 3,200 Sq Ft
    • Built 1987

    Last Sold Summary

    • 2% Below List Price
    • $180/SF
    • 126 Days On Market

    Current Estimated Value $656,993

    Last Listing Agent Aoife Freeman eXp Realty

    12 Bianca Blvd, Chester, NY 10918
    • 78 Panther Mtn Rd, Chester, NY 12817
      78 Panther Mtn Rd, Chester, NY 12817
      78 Panther Mtn Rd, Chester, NY 12817
      /33

      Not Listed For Sale

      78 Panther Mtn Rd, Chester, NY 12817

      • 3 Beds
      • 1 Bath
      • 876 Sq Ft
      • Built 1961
      78 Panther Mtn Rd, Chester, NY 12817

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Angie Mead Gallo Realty ADK Inc

  • 133 E East Shore Dr, Chester, NY 12817
    133 E East Shore Dr, Chester, NY 12817
    133 E East Shore Dr, Chester, NY 12817
    /25

    $875,000

    Pending
    • 2 Beds
    • 2.5 Baths
    • 1,572 Sq Ft

    133 E East Shore Dr, Chester, NY 12817

    A rare opportunity to own a Lakefront Home on Loon Lake. Nestled along the shores of beautiful Loon Lake, this private waterfront retreat offers breathtaking sunset views with a stunning mountain backdrop. This 2-bedroom, 2.5-bath home could live comfortably as a 3-bedroom (septic is sized for a 3 BR) The flexible space is currently used as a home office. Enjoy indoor-outdoor living with a

    Barbara Kearney Hunt Real Estate ERA

    133 E East Shore Dr, Chester, NY 12817
  • 71 Carriage Knoll Rd, Chester, NY 12817
    71 Carriage Knoll Rd, Chester, NY 12817
    71 Carriage Knoll Rd, Chester, NY 12817
    /17

    $58,900

    Sold Jun 12, 2026

    71 Carriage Knoll Rd, Chester, NY 12817

    • Land
    • 1.89 Acres
    • $31,164 per Acre

    Last Sold Summary

    • 39% Above List Price
    • 576 Days On Market

    Last Listing Agent Walter Swartz Gallo Realty ADK Inc

    71 Carriage Knoll Rd, Chester, NY 12817
    • L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817
      L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817
      L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817
      /3

      Not Listed For Sale

      L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817

      L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent John Palermo John R. Palermo

  • 1.2 Cobble Creek Rd, Chester, NY 12853
    1.2 Cobble Creek Rd, Chester, NY 12853
    1.2 Cobble Creek Rd, Chester, NY 12853
    /22

    $79,995

    Pending
    • Land
    • 20.26 Acres
    • $3,948 per Acre

    1.2 Cobble Creek Rd, Chester, NY 12853

    Escape to the mountains with this beautiful 20-acre property in Chester, NY, ideally situated along a year-round maintained town road. The terrain gently climbs from the road, leading to multiple APA-approved building sites for an off-grid cabin or hunting camp offering excellent privacy in a quiet woodland setting. The property features a healthy forest of Northern hardwoods including maple,

    Marc Christmas Christmas and Associates

    1.2 Cobble Creek Rd, Chester, NY 12853
  • 7 Park Place, Chester, NY 10918

    $700,000

    Sold Jul 08, 2026

    7 Park Place, Chester, NY 10918

    • 4 Beds
    • 3.5 Baths
    • 2,780 Sq Ft
    • Built 1986

    Last Sold Summary

    • 5% Below List Price
    • $252/SF
    • 196 Days On Market

    Current Estimated Value $735,662

    Last Listing Agent Luanne McGann Century 21 Full Service Realty

    7 Park Place, 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

      Not Listed For Sale

      116 Carriage Knoll Rd, Chester, NY 12817

      116 Carriage Knoll Rd, Chester, NY 12817

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Walter Swartz Gallo Realty ADK Inc

  • 1.4 Cobble Creek Rd, Chester, NY 12853
    1.4 Cobble Creek Rd, Chester, NY 12853
    1.4 Cobble Creek Rd, Chester, NY 12853
    /23

    $99,995

    • Land
    • 22.88 Acres
    • $4,370 per Acre

    1.4 Cobble Creek Rd, Chester, NY 12853

    Experience the best of Adirondack living on this scenic 22-acre property in Chester, New York. Accessible year-round from a town-maintained road with power nearby, the land offers several elevated APA-approved building sites perfectly positioned for a private cabin, vacation home, or full-time residence. The property is richly forested with mature Northern hardwoods including maple, oak, birch,

    Marc Christmas Christmas and Associates

    1.4 Cobble Creek Rd, Chester, NY 12853
  • 4508 Whispering Hills, Chester, NY 10918

    $300,000

    Sold Apr 20, 2026

    4508 Whispering Hills, Chester, NY 10918

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

    Last Sold Summary

    • 8% Below List Price
    • $280/SF
    • 44 Days On Market

    Current Estimated Value $301,305

    Last Listing Agent Ammar Iqbal eXp Realty

    4508 Whispering Hills, Chester, NY 10918
    • 68 Conklingtown Rd, Chester, NY 10918

      Not Listed For Sale

      68 Conklingtown Rd, Chester, NY 10918

      • 6 Beds
      • 2 Baths
      • 2,138 Sq Ft
      • Built 1950
      68 Conklingtown Rd, Chester, NY 10918

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Moses Schreiber MS Realty Group USA, Inc

  • 1.3 Cobble Creek Rd, Chester, NY 12853
    1.3 Cobble Creek Rd, Chester, NY 12853
    1.3 Cobble Creek Rd, Chester, NY 12853
    /23

    $119,995

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

    1.3 Cobble Creek Rd, 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

    1.3 Cobble Creek Rd, Chester, NY 12853
  • 9 June Rd, Chester, NY 10918

    $620,000

    Sold Oct 29, 2025

    9 June Rd, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,402 Sq Ft
    • Built 1999

    Last Sold Summary

    • 4% Below List Price
    • $258/SF
    • 52 Days On Market

    Current Estimated Value $629,498

    Last Listing Agent Jason Madison eXp Realty

    9 June Rd, Chester, NY 10918
    • 20 High St, Chester, NY 10918

      Est $477,832

      Not Listed For Sale

      20 High St, Chester, NY 10918

      • 3 Beds
      • 2 Baths
      • 2,488 Sq Ft
      • Built 1825
      20 High St, Chester, NY 10918

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Bernadette Corrigan Keller Williams Realty

  • Rd, Chester, NY 12853
    Rd, Chester, NY 12853
    Rd, Chester, NY 12853
    /22

    $89,995

    Pending
    • Land
    • 25.03 Acres
    • $3,595 per Acre

    Rd, Chester, NY 12853

    Adirondack Mountain Retreat with Stream and Trails Discover 25 acres of classic Adirondack wilderness in Chester, New York, tucked along a year-round, town-maintained road. This exceptional property rises gently from the roadside to several attractive, APA-approved building locations, offering excellent opportunities for an off-grid cabin, or vacation retreat. The land is heavily wooded with a

    Marc Christmas Christmas and Associates

    Rd, Chester, NY 12853
  • 3708 Whispering Hills, Chester, NY 10918

    $310,000

    Sold Nov 10, 2025

    3708 Whispering Hills, Chester, NY 10918

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • Built 1990

    Last Sold Summary

    • 5% Above List Price
    • $289/SF
    • 26 Days On Market

    Current Estimated Value $310,182

    Last Listing Agent Nikki Grzegorzewski Keller Williams Realty

    3708 Whispering Hills, Chester, NY 10918
    • 221 Oxford Rd, Chester, NY 10918

      Est $1,140,363

      Not Listed For Sale

      221 Oxford Rd, Chester, NY 10918

      • 4 Beds
      • 3.5 Baths
      • 4,644 Sq Ft
      • Built 2000
      221 Oxford Rd, Chester, NY 10918

      Last Sold Summary

      • 132 Days On Market

      Last Listing Agent Donna Brunell RE/MAX Benchmark Realty Group

  • 4008 Whispering Hills Dr, Chester, NY 10918
    4008 Whispering Hills Dr, Chester, NY 10918
    4008 Whispering Hills Dr, Chester, NY 10918
    /33

    $315,000

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

    4008 Whispering Hills Dr, Chester, NY 10918

    Move in ready townhome with a NYC bus stop within the community!! Whispering Hills in Chester is perfectly positioned for commuters being 2 miles to Route 17. Enjoy a prefect blend of comfort and convenience with a maintenance free lifestyle in this two bedroom townhome. The main floor has brand new flooring, a living room with a wood burning fireplace,and a separate dining area ideal for

    Karen Taphorn Howard Hanna Rand Realty

    4008 Whispering Hills Dr, Chester, NY 10918
  • 23 Renies Rd, Chester, NY 10918

    $644,000

    Sold Feb 12, 2026

    23 Renies Rd, Chester, NY 10918

    • 3 Beds
    • 3 Baths
    • 3,200 Sq Ft
    • Built 1990

    Last Sold Summary

    • 7% Below List Price
    • $201/SF
    • 100 Days On Market

    Current Estimated Value $676,117

    Last Listing Agent Kristie Jacques Century 21 Full Service Realty

    23 Renies Rd, Chester, NY 10918
    • 26 Maple Ln, Monroe, NY 10950

      Est $518,548

      Not Listed For Sale

      26 Maple Ln, Monroe, NY 10950

      • 4 Beds
      • 2 Baths
      • 1,956 Sq Ft
      • Built 1964
      26 Maple Ln, Monroe, NY 10950

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Steven Brown Hudson Valley Realty & Busines

  • 9 Derose Ln, Chester, NY 10918
    9 Derose Ln, Chester, NY 10918
    9 Derose Ln, Chester, NY 10918
    /50

    $675,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 3,100 Sq Ft

    9 Derose Ln, Chester, NY 10918

    Welcome to this elegant colonial in the highly regarded Warwick School District, where timeless charm meets modern comfort. Relax on the inviting front porch while enjoying your morning coffee and breathtaking mountain views. Inside, spacious sun-filled rooms and hardwood flooring throughout the formal living and dining areas create a warm, welcoming atmosphere. A dramatic two-story foyer sets

    Donna Gennaro Howard Hanna Rand Realty

    9 Derose Ln, Chester, NY 10918
  • 27 Grand View Terrace, Chester, NY 10918

    $780,000

    Sold Aug 15, 2025

    27 Grand View Terrace, Chester, NY 10918

    • 5 Beds
    • 3.5 Baths
    • 4,490 Sq Ft
    • Built 2004

    Last Sold Summary

    • 3% Above List Price
    • $174/SF
    • 43 Days On Market

    Current Estimated Value $801,761

    Last Listing Agent Randolph Rogers eXp Realty

    27 Grand View Terrace, Chester, NY 10918
    • 13 Maple Ln, Monroe, NY 10950

      Est $469,179

      Not Listed For Sale

      13 Maple Ln, Monroe, NY 10950

      • 4 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1962
      13 Maple Ln, Monroe, NY 10950

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Nicole Isaacs Century 21 Full Service Realty

  • 78 Pickerel Rd, Monroe, NY 10950
    78 Pickerel Rd, Monroe, NY 10950
    78 Pickerel Rd, Monroe, NY 10950
    /41

    $569,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    78 Pickerel Rd, Monroe, NY 10950

    Beautiful and spacious 4 Bedroom, 2.5 Bath Colonial set on park-like property in a lovely neighborhood with a serene backdrop of mature trees, offering both privacy and a peaceful setting. This home features a large eat-in kitchen with abundant cabinetry, tremendous counter space, and a sliding glass door leading to a newer rear deck—perfect for relaxing or entertaining outdoors.The oversized

    Mary Ann Mitchell eXp Realty

    78 Pickerel Rd, Monroe, NY 10950
  • 68 Southside Dr, Monroe, NY 10950

    $380,000

    Sold Sep 15, 2025

    68 Southside Dr, Monroe, NY 10950

    • 3 Beds
    • 2 Baths
    • 1,632 Sq Ft
    • Built 1940

    Last Sold Summary

    • 15% Below List Price
    • $233/SF
    • 49 Days On Market

    Current Estimated Value $419,618

    Last Listing Agent Carol Buchanan BHG Real Estate Green Team

    68 Southside Dr, Monroe, NY 10950
    • 7 Maple Ln, Monroe, NY 10950

      Est $540,771

      Not Listed For Sale

      7 Maple Ln, Monroe, NY 10950

      • 3 Beds
      • 2 Baths
      • 2,104 Sq Ft
      • Built 1961
      7 Maple Ln, Monroe, NY 10950

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Jason Madison eXp Realty

  • 16 Sunset Ridge, Monroe, NY 10950
    16 Sunset Ridge, Monroe, NY 10950
    16 Sunset Ridge, Monroe, NY 10950
    /29

    $1,299,000

    • 4 Beds
    • 3.5 Baths
    • 5,712 Sq Ft

    16 Sunset Ridge, Monroe, NY 10950

    New updates just completed: Fresh paint throughout and new pavers enhance the home’s curb appeal. HVAC upgrade prior to sale: The seller will professionally install a cooling HVAC system before closing. Secluded Trout Brook Estate: Expansive 5,700+ Sq Ft, 6-Car Garage, Ready for Multi-Gen Living and Entertaining. Nestled on nearly six private acres in the exclusive Trout Brook Estates, this

    Carmela Lopez Borrazas Serhant LLC

    16 Sunset Ridge, Monroe, NY 10950
  • 284 Bull Mill Rd, Chester, NY 10918

    $850,000

    Sold Oct 22, 2025

    284 Bull Mill Rd, Chester, NY 10918

    • 5 Beds
    • 3 Baths
    • 3,485 Sq Ft
    • Built 1997

    Last Sold Summary

    • $244/SF
    • 20 Days On Market

    Current Estimated Value $841,269

    Last Listing Agent Jayne M. Prechtel Keller Williams Valley Realty

    284 Bull Mill Rd, Chester, NY 10918
    • 31 Maple Ln, Monroe, NY 10950

      Est $451,147

      Not Listed For Sale

      31 Maple Ln, Monroe, NY 10950

      • 3 Beds
      • 1 Bath
      • 1,686 Sq Ft
      • Built 1969
      31 Maple Ln, Monroe, NY 10950

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

  • 2 Gate Way, Chester, NY 10918
    2 Gate Way, Chester, NY 10918
    /2

    $710,000

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

    2 Gate Way, 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

    2 Gate Way, Chester, NY 10918
  • 1 Winding Trail, Chester, NY 10918

    $540,000

    Sold Aug 28, 2025

    1 Winding Trail, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 2,040 Sq Ft
    • Built 1991

    Last Sold Summary

    • 10% Below List Price
    • $265/SF
    • 35 Days On Market

    Current Estimated Value $551,142

    Last Listing Agent Donald Serotta Howard Hanna Rand Realty

    1 Winding Trail, Chester, NY 10918
    • 48 Maple Ln, Monroe, NY 10950

      Est $440,440

      Not Listed For Sale

      48 Maple Ln, Monroe, NY 10950

      • 3 Beds
      • 2 Baths
      • 1,003 Sq Ft
      • Built 1963
      48 Maple Ln, Monroe, NY 10950

      Last Sold Summary

      • 99 Days On Market

      Last Listing Agent Franky Garcia Howard Hanna Rand Realty

  • 3815 Whispering Hills Dr, Chester, NY 10918
    3815 Whispering Hills Dr, Chester, NY 10918
    3815 Whispering Hills Dr, Chester, NY 10918
    /50

    $370,000

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

    3815 Whispering Hills Dr, Chester, NY 10918

    Discover your new haven at this charming 3-bedroom, 2.5-bathroom condo nestled in the vibrant community of Chester, NY. Perfect for those looking to infuse a home with their personal style, this residence offers fantastic potential to make it your own. Let your imagination take the reins and make this spacious house into your dream home! The condo is thoughtfully designed with ample room for rest

    David Kraus MK Realty Inc

    3815 Whispering Hills Dr, Chester, NY 10918
  • 411 Prospect Rd, Chester, NY 10918

    $610,000

    Sold Aug 25, 2025

    411 Prospect Rd, Chester, NY 10918

    • 4 Beds
    • 2 Baths
    • 1,987 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Above List Price
    • $307/SF
    • 39 Days On Market

    Current Estimated Value $614,168

    Last Listing Agent Dana Posner Howard Hanna Rand Realty

    411 Prospect Rd, Chester, NY 10918
    • 68 Evan Rd, Warwick, NY 10990

      Est $410,110

      Not Listed For Sale

      68 Evan Rd, Warwick, NY 10990

      • 3 Beds
      • 2.5 Baths
      • 1,452 Sq Ft
      • Built 1995
      68 Evan Rd, Warwick, NY 10990

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Antonette Vogel BHG Real Estate Green Team

  • 15 Deer Run, Chester, NY 12817
    15 Deer Run, Chester, NY 12817
    15 Deer Run, Chester, NY 12817
    /5

    $49,000

    $16K PRICE DROP
    • Land
    • 10.14 Acres
    • $4,832 per Acre

    15 Deer Run, Chester, NY 12817

    10+ Acre recreational vacation location in the Town of Chester. Private maintained road with nice camps and homes. The lot feels as if its set in the heart of a wildlife preserve. Small non salvageable cabin on the property that had electric to the site. 6 miles to North Creek the home of Gore Mountain Ski Center. Build your vacation home here in the Adirondacks.

    Patricia Seitz McAlonen Pearsall Realty

    15 Deer Run, Chester, NY 12817
  • 4 Oak St, Chester, NY 10918

    $525,000

    Sold Jul 01, 2026

    4 Oak St, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,888 Sq Ft
    • Built 1967

    Last Sold Summary

    • 5% Above List Price
    • $278/SF
    • 27 Days On Market

    Current Estimated Value $507,232

    Last Listing Agent Frank Muccari Cronin & Company Real Estate

    4 Oak St, Chester, NY 10918
    • 100 Marian Ct, Warwick, NY 10990

      Est $434,497

      Not Listed For Sale

      100 Marian Ct, Warwick, NY 10990

      • 3 Beds
      • 2.5 Baths
      • 1,528 Sq Ft
      • Built 1986
      100 Marian Ct, Warwick, NY 10990

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Jennifer DiCostanzo RE/MAX Town & Country

  • 9 Mount Ridge Ct, Monroe, NY 10950
    9 Mount Ridge Ct, Monroe, NY 10950
    9 Mount Ridge Ct, Monroe, NY 10950
    /49

    $595,000

    $55K PRICE DROP Pending
    • 5 Beds
    • 3 Baths
    • 2,983 Sq Ft

    9 Mount Ridge Ct, Monroe, NY 10950

    Spacious Center Hall Colonial offering the perfect blend of comfort, style, and functionality. A dramatic two-story entry welcomes you into this thoughtfully designed home, featuring an open-concept layout ideal for both everyday living and entertaining.The heart of the home is the expansive kitchen, complete with abundant counter space, a large dinette area, and sliding glass doors leading

    Richard Froehlich RE/MAX Benchmark Realty Group

    9 Mount Ridge Ct, Monroe, NY 10950

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