Chester, NY Homes

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  $75,000 Sold Nov 10, 2025

  6 E Shore Dr, Chester, NY 12817

  • Land
  • 0.67 Acre
  • $111,940 per Acre

  Last Sold Summary

  • 36% Above List Price
  • 5 Days On Market

  Last Listing Agent Michelle Decoteau KW Platform

  6 E Shore Dr, Chester, NY 12817
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  Est $286,542 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,240 Sq Ft

  1103 Deerfield Rd, Monroe, NY 10950

  1103 Deerfield Rd, Monroe, NY 10950
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  /50

  $699,000

  • 3 Beds
  • 3 Baths
  • 3,000 Sq Ft

  360 Prospect Rd, Chester, NY 10918

  B"H Grab this opportunity!!! Cozy Home in great condition sitting on a 3.2 ACER Property!!! Enjoy the above ground pool !!!Wonderful neighborhood and calm area. Open living room with wood burning fireplace, The kitchen offers a breakfast bar, Center island, Stainless steel appliances, Multiple counter space and cabinets. Finished lower level with a Den/office, Family room and full bathroom.

  Joseph Mendlowitz eRealty Advisors, Inc

  360 Prospect Rd, Chester, NY 10918
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  $339,000 Sold Apr 01, 2025

  3111 Whispering Hills Dr, Chester, NY 10918

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

  Last Sold Summary

  • $258/SF
  • 50 Days On Market

  Last Listing Agent Annmarie Kovacs Howard Hanna Rand Realty

  3111 Whispering Hills Dr, Chester, NY 10918
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  Est $322,064 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,334 Sq Ft

  1004 Swan Hollow Rd, Monroe, NY 10950

  1004 Swan Hollow Rd, Monroe, NY 10950
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  $37,500

  • Land
  • 2 Acres
  • $18,750 per Acre

  13 Carriage Rd, Chester, NY

  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 steeper 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

  13 Carriage Rd, Chester, NY
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  $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

  Last Listing Agent Hershel Lowy Master Realty Group Inc.

  3107 Whispering Hills, Chester, NY 10918
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  Est $311,195 Not Listed For Sale

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

  902 Swan Hollow Rd, Monroe, NY 10950

  902 Swan Hollow Rd, Monroe, NY 10950
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  $76,900

  • 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
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  $700,000 Sold Jul 08, 2025

  138 Dug Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,452 Sq Ft
  • Built 1974

  Last Sold Summary

  • $285/SF
  • 49 Days On Market

  Current Estimated Value $706,925

  Last Listing Agent Jake Garay Serhant LLC

  138 Dug Rd, Chester, NY 10918
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  Est $319,916 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,334 Sq Ft

  901 Swan Hollow Rd, Monroe, NY 10950

  901 Swan Hollow Rd, Monroe, NY 10950
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  /25

  $78,900

  • 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
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  $290,000 Sold Jun 05, 2025

  4401 Whispering Hills Dr, Chester, NY 10918

  • 2 Beds
  • 1 Bath
  • 1,118 Sq Ft
  • Built 1989

  Last Sold Summary

  • 5% Above List Price
  • $259/SF
  • 30 Days On Market

  Current Estimated Value $301,774

  Last Listing Agent Annmarie Kovacs Howard Hanna Rand Realty

  4401 Whispering Hills Dr, Chester, NY 10918
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  Est $293,518 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,240 Sq Ft

  808 Swan Hollow Rd, Monroe, NY 10950

  808 Swan Hollow Rd, Monroe, NY 10950
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  $750,000

  • 3 Beds
  • 3 Baths
  • 2,870 Sq Ft

  16 Oxford Springs Rd, Chester, NY 10918

  Discover modern living at its best in this beautifully designed 2,870 sq ft contemporary home with flexible floor plan and wonderful tranquility! Set on 4.1 private acres and featuring its own pond and seasonal babbling brook, 16 Oxford Springs Road is perfect for those seeking a full-time residence or Hudson Valley getaway. This home offers retreat-like privacy yet is only minutes to all

  Jennifer Gold RE/MAX Benchmark Realty Group

  16 Oxford Springs Rd, Chester, NY 10918
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  $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

  Last Listing Agent Kichka Pascaru Christie's Int. Real Estate

  165 Creamery Pond Rd, Chester, NY 10918
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  Est $354,433 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft

  707 Swan Hollow Rd, Monroe, NY 10950

  707 Swan Hollow Rd, Monroe, NY 10950
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  /5

  $74,900

  • Land
  • 1.79 Acres
  • $41,844 per Acre

  L4-5 Marina Rd, Chester, NY 12817

  This is two lots combined for better access and development and has beach rights to two beaches shown on map. HOA Owner's association fee includes beach maintenance. HOA board is working toward the possibility of installing a boat docksystem for the future. Presently there is space for non motorized craft on the beaches. Broker (John R. Palermo) is handling this property for his family's LLC

  John Palermo John R. Palermo

  L4-5 Marina Rd, Chester, NY 12817
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  $350,000 Sold Jul 28, 2025

  2816 Whispering Hills, Chester, NY 10918

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

  Last Sold Summary

  • $263/SF
  • 23 Days On Market

  Current Estimated Value $360,196

  Last Listing Agent Bernadette Giordano Howard Hanna Rand Realty

  2816 Whispering Hills, Chester, NY 10918
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  Est $357,473 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,825 Sq Ft

  604 Mountain Laurel Dr, Monroe, NY 10950

  604 Mountain Laurel Dr, Monroe, NY 10950
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  /10

  $359,900 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,376 Sq Ft

  264 Heritage Ln, Monroe, NY 10950

  Move-In Ready 3-Bedroom Condo in the Monroe-Woodbury School District. Discover comfort, convenience, and community in this 3-bedroom, 1.5-bath condo located in one of the most desirable areas of the Hudson Valley. The open-concept main level features a bright and spacious living room, a dining area, and a well-appointed kitchen—perfect for everyday living and entertaining. Upstairs, you’ll find

  Frank Golio Howard Hanna Rand Realty

  264 Heritage Ln, Monroe, NY 10950
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  $310,000 Sold Jul 21, 2025

  4706 Whispering Hills, Chester, NY 10918

  • 2 Beds
  • 1.5 Baths
  • 1,086 Sq Ft
  • Built 1987

  Last Sold Summary

  • 2% Above List Price
  • $285/SF
  • 18 Days On Market

  Current Estimated Value $315,104

  Last Listing Agent Jessica Evans Keller Williams Hudson Valley

  4706 Whispering Hills, Chester, NY 10918
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  Est $312,630 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,334 Sq Ft

  601 Mountain Laurel Dr, Monroe, NY 10950

  601 Mountain Laurel Dr, Monroe, NY 10950
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  /23

  $68,900

  • Land
  • 3.05 Acres
  • $22,590 per Acre

  82 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

  82 Carriage Knoll Rd, Chester, NY 12817
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  $265,000 Sold Jul 11, 2025

  10 El Dorado Trail, Chester, NY 10918

  • Land
  • 6.3 Acres
  • $42,063 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 152 Days On Market

  Current Estimated Value $265,122

  Last Listing Agent Lisandra Rivera Keller Williams Realty

  10 El Dorado Trail, Chester, NY 10918
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  Est $323,706 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,334 Sq Ft

  204 Mountain Laurel Dr, Monroe, NY 10950

  204 Mountain Laurel Dr, Monroe, NY 10950
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  $49,500

  • Land
  • 3.36 Acres
  • $14,732 per Acre

  20 Carriage Rd, Chester, NY

  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 steeper 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

  20 Carriage Rd, Chester, NY
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  $750,000 Sold May 15, 2025

  16 Spectrum Dr, Chester, NY 10918

  • 3 Beds
  • 4 Baths
  • 2,276 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Above List Price
  • $330/SF
  • 16 Days On Market

  Current Estimated Value $760,121

  Last Listing Agent John Olivero Keller Williams Realty

  16 Spectrum Dr, Chester, NY 10918
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  Est $486,179 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,523 Sq Ft

  62 Lincoln Rd, Monroe, NY 10950

  62 Lincoln Rd, Monroe, NY 10950
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  $65,000

  • Land
  • 5.42 Acres
  • $11,993 per Acre

  L7 Macglashan Ln, Chester, NY 12817

  Very nice 5.42 acres of property with plenty of secluded building options. Gently sloping topography with mixed hardwood and conifers throughout. An abundance of wildlife signs from end to end of this parcel. This property is zoned ''Rural Use'' and would be used ideally for a home or cabin (one-primary single family residence) with garage or other auxiliary building. Seller financing possible

  Walter Swartz Gallo Realty ADK Inc

  L7 Macglashan Ln, Chester, NY 12817
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  $800,000 Sold Jun 06, 2025

  118 Murray Dr, Chester, NY 10918

  • 5 Beds
  • 4 Baths
  • 3,418 Sq Ft
  • Built 1978

  Last Sold Summary

  • 6% Below List Price
  • $234/SF
  • 110 Days On Market

  Current Estimated Value $816,314

  Last Listing Agent Brian Caplicki Keller Williams Hudson Valley

  118 Murray Dr, Chester, NY 10918
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  Est $535,248 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,134 Sq Ft

  59 Wilson Rd, Monroe, NY 10950

  59 Wilson Rd, Monroe, NY 10950
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  $425,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,266 Sq Ft

  84 Pine Hill Rd, Chester, NY 10918

  Welcome to your dream home! This beautifully renovated ranch-style house sits on a stunning 5-acre lot, offering privacy and tranquility amidst nature's beauty. Step inside to discover a tastefully updated interior featuring modern finishes and top-notch upgrades throughout. The spacious open-concept living areas are perfect for entertaining, and the gourmet kitchen boasts brand-new appliances

  Samuel Kohn eRealty Advisors, Inc

  84 Pine Hill Rd, Chester, NY 10918
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  $560,000 Sold Jul 01, 2025

  92 Pickerel Rd, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 2,016 Sq Ft
  • Built 1969

  Last Sold Summary

  • 2% Below List Price
  • $278/SF
  • 148 Days On Market

  Current Estimated Value $568,786

  Last Listing Agent Richard Wawrynek Howard Hanna Rand Realty

  92 Pickerel Rd, Monroe, NY 10950
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  Est $533,269 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,644 Sq Ft

  9 Grant Dr, Monroe, NY 10950

  9 Grant Dr, Monroe, NY 10950
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  $849,900

  • 4 Beds
  • 2.5 Baths
  • 2,603 Sq Ft

  32 Mountainside Dr, Chester, NY 10918

  A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This will truly be a lovely property with land, privacy and wonderful mountain views! This modern farm house cape features over 2,600 sq ft. and is completely CUSTOM and DELIVERED TURN-KEY ... build this home, or bring your own dream plans/ideas! This ONE LEVEL living

  Karen Gauvin Our House Real Estate Group

  32 Mountainside Dr, Chester, NY 10918
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  /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

  Last Listing Agent James Nester Cork Nester's True North Prop

  13 Dewey Rd, Chester, NY 12860
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  Est $484,943 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,644 Sq Ft

  1 Grant Dr, Monroe, NY 10950

  1 Grant Dr, Monroe, NY 10950
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  $350,000

  • Land
  • 5.1 Acres
  • $68,627 per Acre

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918

  Very private lot in mature subdivision of large homes. Home site has been cleared and driveway base laid down. With a small amount of brush-clearing in the tree line there can be views of the valley and watershed lands.

  Theresa Powers Keller Williams Realty

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
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  $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

Showing Results 241 - 280, Page 7 of 18