6,751

Chester, NY Homes

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  • 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 $219,500

    Last Listing Agent Michelle Decoteau KW Platform

    6 E Shore Dr, Chester, NY 12817
    • 19 Mount Ridge Ct, Monroe, NY 10950

      Est $640,550

      Not Listed For Sale

      19 Mount Ridge Ct, Monroe, NY 10950

      • 4 Beds
      • 2.5 Baths
      • 2,698 Sq Ft
      • Built 2000
      19 Mount Ridge Ct, Monroe, NY 10950

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Christian Baez KW Hudson Valley United

  • 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
  • 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 $712,470

    Last Listing Agent Sandra Cassio Robert DeFalco Realty, Inc.

    1 Hillview Terrace, Chester, NY 10918
    • 7 Mount Ridge Ct, Monroe, NY 10950

      Est $592,302

      Not Listed For Sale

      7 Mount Ridge Ct, Monroe, NY 10950

      • 4 Beds
      • 2.5 Baths
      • 2,136 Sq Ft
      • Built 2002
      7 Mount Ridge Ct, Monroe, NY 10950

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Rosalie Cook Weichert Realtors

  • 3414 Whispering Hills, Chester, NY 10918
    3414 Whispering Hills, Chester, NY 10918
    3414 Whispering Hills, Chester, NY 10918
    /34

    $349,999

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

    3414 Whispering Hills, Chester, NY 10918

    Welcome home to this beautifully updated 3-bedroom, 2-bathroom condominium with a 1-car garage, perfectly situated in the highly sought-after Whispering Hills community. Offering modern upgrades, spacious living, and resort-style amenities, this home is truly move-in ready. Step inside to discover a bright, open floor plan featuring gleaming hardwood floors, an updated chef-inspired kitchen with

    Kevin Grier KW Hudson Valley United

    3414 Whispering Hills, Chester, NY 10918
  • 58 Oxford Springs Rd, Chester, NY 10918

    $370,000

    Sold Jul 01, 2026

    58 Oxford Springs Rd, Chester, NY 10918

    • 1 Bed
    • 1 Bath
    • 783 Sq Ft
    • Built 1920

    Last Sold Summary

    • 6% Above List Price
    • $473/SF
    • 27 Days On Market

    Current Estimated Value $341,583

    Last Listing Agent Christine Koenig Keller Williams Realty

    58 Oxford Springs Rd, Chester, NY 10918
    • 465 Meri Ln, Monroe, NY 10950

      Est $450,001

      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

      Last Listing Agent Wenpeng Guan KW Hudson Valley United

  • L4/5 Marina Rd, Chester, NY 12817
    L4/5 Marina Rd, Chester, NY 12817
    L4/5 Marina Rd, Chester, NY 12817
    /6

    $88,900

    • Land
    • 1.79 Acres
    • $49,665 per Acre

    L4/5 Marina Rd, Chester, NY 12817

    This lot has beach rights to two beaches shown on map. Home Owners's associationfee includes beach maintenance only. HOA board is working toward the possibility of installing a boat docking system for the future. Presently there is space of non motorized craft on the beaches. Broker (John R. Palermo) is handling this property for his family's trust of which he is a co-executor. New excavation

    John Palermo John R. Palermo

    L4/5 Marina 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 $311,006

    Last Listing Agent Hershel Lowy Master Realty Group Inc.

    3107 Whispering Hills, Chester, NY 10918
    • 463 Meri Ln, Monroe, NY 10950

      Est $429,757

      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

      Last Listing Agent Beth Palma Keller Williams Realty

  • 1 Periwinkle Ct, Chester, NY 10918
    1 Periwinkle Ct, Chester, NY 10918
    1 Periwinkle Ct, Chester, NY 10918
    /9

    $750,000

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

    1 Periwinkle Ct, 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 Periwinkle Ct, Chester, NY 10918
  • L46 Pinewood Rd N, Chester, NY 12817
    L46 Pinewood Rd N, Chester, NY 12817
    L46 Pinewood Rd N, Chester, NY 12817
    /4

    $17,000

    Sold Jul 06, 2026

    L46 Pinewood Rd N, Chester, NY 12817

    • Land
    • 1.38 Acres
    • $12,319 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 10 Days On Market

    Last Listing Agent Julia Pucciarelli Gallo Realty ADK Inc

    L46 Pinewood Rd N, Chester, NY 12817
    • 326 Heritage Ln, Monroe, NY 10950

      Est $371,422

      Not Listed For Sale

      326 Heritage Ln, Monroe, NY 10950

      • 3 Beds
      • 2.5 Baths
      • 1,698 Sq Ft
      • Built 1998
      326 Heritage Ln, Monroe, NY 10950

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Ernie Acampora River Realty Services, Inc.

  • 220 Oxford Rd, Chester, NY 10918
    220 Oxford Rd, Chester, NY 10918
    220 Oxford Rd, Chester, NY 10918
    /20

    $894,000

    $105K 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 $694,192

    Last Listing Agent Kichka Pascaru Douglas Elliman Real Estate

    165 Creamery Pond Rd, Chester, NY 10918
    • 301 Heritage Ln, Monroe, NY 10950

      Est $436,217

      Not Listed For Sale

      301 Heritage Ln, Monroe, NY 10950

      • 3 Beds
      • 2.5 Baths
      • 1,698 Sq Ft
      • Built 1998
      301 Heritage Ln, Monroe, NY 10950

      Last Sold Summary

      • 111 Days On Market

      Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  • 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
  • L62.2 Moffitt Rd, Chester, NY 12817
    L62.2 Moffitt Rd, Chester, NY 12817
    L62.2 Moffitt Rd, Chester, NY 12817
    /3

    $68,000

    Sold Jul 07, 2026

    L62.2 Moffitt Rd, Chester, NY 12817

    • Land
    • 12 Acres
    • $5,667 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 125 Days On Market

    Last Listing Agent Carol Monroe Najer Realty

    L62.2 Moffitt Rd, Chester, NY 12817
    • 51 Pewter Cir, Chester, NY 10918

      Est $561,001

      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

      Last Listing Agent Michele Tobin Keller Williams Realty

  • 21 Trotting Dr, Chester, NY 10918
    21 Trotting Dr, Chester, NY 10918
    21 Trotting Dr, Chester, NY 10918
    /50

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft

    21 Trotting Dr, Chester, NY 10918

    Welcome to this impeccably maintained raised ranch in the highly sought-after Surrey Meadows Community. Upon entering the foyer, you'll find a practical area beneath the stairs, providing convenient storage for coats and shoes. The lower level features a spacious bedroom with access to a full bathroom, complemented by a versatile bonus room perfect for a cozy den or guest accommodation. Ascend

    Michele Kayser Keller Williams Realty

    21 Trotting Dr, 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 $433,369

    Last Listing Agent Gary Silberstein Keller Williams Valley Realty

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

      Est $606,386

      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

      Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  • 1 Arborvitae Ct, Chester, NY 10918
    1 Arborvitae Ct, Chester, NY 10918
    /2

    $725,000

    • 3 Beds
    • 2.5 Baths
    • 2,677 Sq Ft

    1 Arborvitae Ct, 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 9 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 Arborvitae Ct, 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 $372,917

    Last Listing Agent Claude Brischoux Keller Williams Realty

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

      Est $739,465

      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

      Last Listing Agent Jennifer Connolly BHHS Gross & Jansen

  • 94 Booth Rd, Chester, NY 10918
    94 Booth Rd, Chester, NY 10918
    94 Booth Rd, Chester, NY 10918
    /23

    $529,000

    $61K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,083 Sq Ft

    94 Booth Rd, Chester, NY 10918

    Some lots just have good bones. This one has it's own private nature trail, stocked pond rights, and a cul-de-sac that dead-ends into miles of nature trails anchored by a solid, spacious raised ranch on 1.8 acres. Inside, the home has been partially updated and offers solid bones with room to add your own touch over time. The house delivers where it counts. Three bedrooms, two and a half baths,

    Craig Watters Compass Greater NY, LLC

    94 Booth Rd, 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 $333,968

    Last Listing Agent James Nester Cork Nester's True North Properties, Inc.

    13 Dewey Rd, Chester, NY 12860
    • 11 Pewter Cir, Chester, NY 10918

      Est $597,437

      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

      Last Listing Agent Jorge Vasquez Vasquez 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
  • 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
    • 16 Pewter Cir, Chester, NY 10918

      Est $705,352

      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

      Last Listing Agent Lisa McAteer Scranton Wilkes Barre Regional

  • 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
  • L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817
    L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817
    L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817
    /13

    $79,500

    Sold Dec 09, 2025

    L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817

    • Land
    • 14.7 Acres
    • $5,408 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 110 Days On Market

    Last Listing Agent Julia Pucciarelli Gallo Realty ADK Inc

    L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817
    • 274 Heritage Ln, Monroe, NY 10950

      Est $371,184

      Not Listed For Sale

      274 Heritage Ln, Monroe, NY 10950

      • 3 Beds
      • 1.5 Baths
      • 1,376 Sq Ft
      • Built 1988
      274 Heritage Ln, Monroe, NY 10950

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Jeffrey Freundlich Howard Hanna Rand Realty

  • 888 Landon Hill Rd, Chester, NY 12817
    888 Landon Hill Rd, Chester, NY 12817
    888 Landon Hill Rd, Chester, NY 12817
    /23

    $85,000

    $10K PRICE DROP
    • Land
    • 1 Acre
    • $85,000 per Acre

    888 Landon Hill Rd, Chester, NY 12817

    One acre building lot, cleared and ready to build on. There is a ''tiny home'' on the property that can be used to live in while you are in the process of construction. 200 amp electric service installed and there is a point well on the property with water that would just need a pump installed. Buyer would be responsible for permits through the town as the current owner has not gone through the

    Kelli May Better Way Realty Inc

    888 Landon Hill Rd, Chester, NY 12817
  • 12 Juniper Ln, Monroe, NY 10950

    $550,000

    Sold Mar 09, 2026

    12 Juniper Ln, Monroe, NY 10950

    • 4 Beds
    • 3 Baths
    • 2,288 Sq Ft
    • Built 1972

    Last Sold Summary

    • 4% Below List Price
    • $240/SF
    • 120 Days On Market

    Current Estimated Value $556,353

    Last Listing Agent Shaylene Neumann Houlihan Lawrence Inc.

    12 Juniper Ln, Monroe, NY 10950
    • 245 Heritage Ln, Monroe, NY 10950

      Est $394,758

      Not Listed For Sale

      245 Heritage Ln, Monroe, NY 10950

      • 3 Beds
      • 2.5 Baths
      • 1,585 Sq Ft
      • Built 1989
      245 Heritage Ln, Monroe, NY 10950

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Anita S. Cristiano Five Star Realty Group Intl

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

    $775,000

    $113K 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
  • 101 Whitetail Run, Chester, NY 10918

    $589,000

    Sold Jul 13, 2026

    101 Whitetail Run, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,854 Sq Ft
    • Built 1988

    Last Sold Summary

    • $318/SF
    • 21 Days On Market

    Current Estimated Value $742,439

    Last Listing Agent Aylin Ippolito Cronin & Company Real Estate

    101 Whitetail Run, Chester, NY 10918

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