Chester, NY Homes

• 

  Est $563,223 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,298 Sq Ft

  9 Adams Ct, Monroe, NY 10950

  9 Adams Ct, Monroe, NY 10950
• 

  

  

  /18

  $310,000

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

  3120 Whispering Hills, Chester, NY 10918

  Welcome to this charming 2-bedroom condo in the desirable Whispering Hills community! This unit faces green space and trees for added privacy as well as comfortable living spaces. The home features a cozy living room with a fireplace, a dining area, and a full kitchen ready for everyday meals or weekend entertaining. Enjoy the convenience of having your own in-unit washer and dryer, plus a

  Bente Brown John J Lease REALTORS Inc

  3120 Whispering Hills, Chester, NY 10918
• 

  $475,000 Sold Apr 22, 2025

  397 Bellvale Rd, Chester, NY 10918

  • 2 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • Built 1983

  Last Sold Summary

  • $327/SF
  • 45 Days On Market

  Current Estimated Value $491,549

  Last Listing Agent Juan Bautista Keller Williams Realty

  397 Bellvale Rd, Chester, NY 10918
• 

  Est $545,836 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,894 Sq Ft

  59 Washington Rd, Monroe, NY 10950

  59 Washington Rd, Monroe, NY 10950
• 

  

  

  /37

  $569,999

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

  78 Pickerel Rd, Monroe, NY 10950

  Welcome to this charming Colonial set in the desirable Trout Brook ll subdivision of Monroe. This lovely home offers the perfect balance of privacy and convenience—just minutes to local shops and the village, and a short 10–15 minute drive to all major highways. Plus, you're only an hour from NYC, making it ideal for commuters or weekend getaways. Outdoor enthusiasts will love the close proximity

  Lauren Kelly Howard Hanna Rand Realty

  78 Pickerel Rd, Monroe, NY 10950
• 

  $270,000 Sold Apr 28, 2025

  1213 Whispering Hills, Chester, NY 10918

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft
  • Built 1984

  Last Sold Summary

  • 4% Below List Price
  • $249/SF
  • 94 Days On Market

  Current Estimated Value $292,360

  Last Listing Agent Nicholas D'Aloisio Keller Williams Rlty Integrity

  1213 Whispering Hills, Chester, NY 10918
• 

  Est $506,109 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,744 Sq Ft

  26 Harding Way, Monroe, NY 10950

  26 Harding Way, Monroe, NY 10950
• 

  

  /8

  $225,000

  • Land
  • 1 Acre
  • $225,000 per Acre

  34 Mountainside Dr, Chester, NY 10918

  Lovely 1-Acre lot w/MOUNTAIN VIEWS & NATURAL GAS in a beautiful newly built SUB-DIVISION. Build out this nearly completely built lovely sub-division, curb-cuts, paved road sloping lot perfect for a WALK-OUT BASEMENT and DECKS FOR BEAUTIFUL VIEWS ... FULLY APPROVED LOT, ESTABLISHED NEIGHBORHOOD, VERY COMMUTABLE location! Close to the vibrant shopping, restaurants, nightlife, shows/events at

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, Chester, NY 10918
• 

  

  /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
• 

  Est $514,699 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,088 Sq Ft

  67 Washington Rd, Monroe, NY 10950

  67 Washington Rd, Monroe, NY 10950
• 

  

  /24

  $74,900

  • Land
  • 4.31 Acres
  • $17,378 per Acre

  102 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

  102 Carriage Knoll Rd, Chester, NY 12817
• 

  $782,000 Sold Apr 03, 2025

  152 Gibson Hill Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,176 Sq Ft
  • Built 1997

  Last Sold Summary

  • 5% Below List Price
  • $246/SF
  • 230 Days On Market

  Current Estimated Value $817,473

  Last Listing Agent Kimberly Corkum Keller Williams Realty

  152 Gibson Hill Rd, Chester, NY 10918
• 

  Est $545,020 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,944 Sq Ft

  2 Tyler Place, Monroe, NY 10950

  2 Tyler Place, Monroe, NY 10950
• 

  

  /17

  $309,900

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

  1503 Whispering Hills, Chester, NY 10918

  Big price reduction! Come see it before it's gone. Nice end unit 3 bedroom 2.5 bath condo with 2 car garage in whispering hills. Primary bedroom with private full bath and 2 nice size extra bedrooms plus a hall bath on the 2nd floor. Warm up on those cold nights with the fireplace in the living room. Enjoy a quiet moment on your private patio sipping your coffee. Great location with playground

  Darlene Provino Century 21 E & M Williams Rlty

  1503 Whispering Hills, Chester, NY 10918
• 

  $75,000 Sold Jul 09, 2025

  31 Leone Ln, Chester, NY 10918

  • Land
  • 7.5 Acres
  • $10,000 per Acre

  Last Sold Summary

  • 50% Below List Price
  • 73 Days On Market

  Current Estimated Value $147,000

  Last Listing Agent Carole McCann Hudson Heritage Realty

  31 Leone Ln, Chester, NY 10918
• 

  Est $536,764 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,092 Sq Ft

  63 Pickerel Rd, Monroe, NY 10950

  63 Pickerel Rd, Monroe, NY 10950
• 

  

  /50

  $1,775,000

  • 4 Beds
  • 2.5 Baths
  • 3,348 Sq Ft

  20 Goshen Rd, Chester, NY 10918

  Discover a rare opportunity to own a one-of-a-kind estate set on 53 sprawling acres in the heart of Chester, NY—perfectly suited for luxury living, farming, or future development with subdivision potential. This impressive property features a 3-car garage with 10-foot doors, outdoor wood-burning furnace, and two 250-gallon oil tanks for efficient heating.Nature lovers and hobby farmers

  Ramanjit Dhanoa eXp Realty

  20 Goshen Rd, Chester, NY 10918
• 

  $665,000 Sold Jul 15, 2025

  174 Creamery Pond Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,608 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $255/SF
  • 27 Days On Market

  Current Estimated Value $701,546

  Last Listing Agent Michele Tobin Keller Williams Realty

  174 Creamery Pond Rd, Chester, NY 10918
• 

  Est $504,861 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,712 Sq Ft

  17 Surrey Rd, Chester, NY 10918

  17 Surrey Rd, Chester, NY 10918
• 

  

  /71

  $299,900

  • Land
  • 165.92 Acres
  • $1,807 per Acre

  L9 Atateka Rd, Chester, NY 12817

  This is a fantastic opportunity to own your own patch of beautiful Adirondack woods, nearly 166 acres, complete with a perennial stream, beaver pond, mature timber, and plenty of wild game. Use this property as your own recreational playground or build your dream home or camp in this peaceful, wooded retreat. Property is access by a right of way from Atateka Rd. Proceed ~400 feet to property

  John O'Donnell Timberland Realty

  L9 Atateka Rd, Chester, NY 12817
• 

  $465,000 Sold Aug 04, 2025

  559 Laroe Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 1970

  Last Sold Summary

  • 11% Below List Price
  • $245/SF
  • 239 Days On Market

  Current Estimated Value $477,859

  Last Listing Agent Eliezer Safdie Sage Realty Center LLC

  559 Laroe Rd, Chester, NY 10918
• 

  Est $493,903 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,780 Sq Ft

  25 Surrey Rd, Chester, NY 10918

  25 Surrey Rd, Chester, NY 10918
• 

  $457,500 Sold Jul 25, 2025

  12 Mari Rd, Chester, NY 10918

  • 4 Beds
  • 1.5 Baths
  • 1,842 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $248/SF
  • 32 Days On Market

  Current Estimated Value $470,715

  Last Listing Agent Ryan Degnan Howard Hanna Rand Realty

  12 Mari Rd, Chester, NY 10918
• 

  Est $735,201 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,006 Sq Ft

  69 Dug Rd, Chester, NY 10918

  69 Dug Rd, Chester, NY 10918
• 

  $345,000 Sold Aug 05, 2025

  326 Heritage Ln, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,698 Sq Ft
  • Built 1998

  Last Sold Summary

  • 4% Below List Price
  • $203/SF
  • 37 Days On Market

  Current Estimated Value $358,730

  Last Listing Agent Ernie Acampora River Realty Services, Inc.

  326 Heritage Ln, Monroe, NY 10950
• 

  Est $671,704 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,708 Sq Ft

  16 Twin Brooks Dr, Chester, NY 10918

  16 Twin Brooks Dr, Chester, NY 10918
• 

  $749,900 Sold Apr 18, 2025

  2 Grand View Terrace, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,480 Sq Ft
  • Built 2004

  Last Sold Summary

  • $215/SF
  • 29 Days On Market

  Current Estimated Value $764,226

  Last Listing Agent Randolph Rogers eXp Realty

  2 Grand View Terrace, Chester, NY 10918
• 

  Est $612,640 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 2,554 Sq Ft

  73 Dug Rd, Chester, NY 10918

  73 Dug Rd, Chester, NY 10918
• 

  $555,000 Sold Oct 21, 2025

  114 Old Mansion Rd, Chester, NY 10918

  • 4 Beds
  • 2 Baths
  • 3,330 Sq Ft
  • Built 1930

  Last Sold Summary

  • 21% Below List Price
  • $167/SF
  • 76 Days On Market

  Last Listing Agent Hershel Lowy Master Realty Group Inc.

  114 Old Mansion Rd, Chester, NY 10918
• 

  Est $501,248 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,882 Sq Ft

  4 Stevens Place, Chester, NY 10918

  4 Stevens Place, Chester, NY 10918
• 

  $725,000 Sold Jun 30, 2025

  56 Sunset Ridge Rd, Monroe, NY 10950

  • 4 Beds
  • 4 Baths
  • 3,626 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Above List Price
  • $200/SF
  • 34 Days On Market

  Current Estimated Value $769,840

  Last Listing Agent Moses Schreiber MS Realty Group USA, Inc

  56 Sunset Ridge Rd, Monroe, NY 10950
• 

  Est $572,633 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,980 Sq Ft

  38 Ayr Rd, Chester, NY 10918

  38 Ayr Rd, Chester, NY 10918
• 

  $520,000 Sold Feb 06, 2025

  3 Seely Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,208 Sq Ft
  • Built 1988

  Last Sold Summary

  • 13% Below List Price
  • $236/SF
  • 169 Days On Market

  Current Estimated Value $556,114

  Last Listing Agent Christina Rowan Howard Hanna Rand Realty

  3 Seely Rd, Chester, NY 10918
• 

  Est $618,296 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,784 Sq Ft

  46 Ayr Rd, Chester, NY 10918

  46 Ayr Rd, Chester, NY 10918
• 

  $515,000 Sold Jan 30, 2025

  7 Juniper Ln, Monroe, NY 10950

  • 5 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • Built 1972

  Last Sold Summary

  • 3% Below List Price
  • $234/SF
  • 49 Days On Market

  Current Estimated Value $545,413

  Last Listing Agent Micaela Stanaland Howard Hanna Rand Realty

  7 Juniper Ln, Monroe, NY 10950
• 

  Est $448,214 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,358 Sq Ft

  13 Mari Rd, Chester, NY 10918

  13 Mari Rd, Chester, NY 10918
• 

  $345,000 Sold Jan 07, 2025

  4407 Whispering Hills Dr, Chester, NY 10918

  • 2 Beds
  • 1.5 Baths
  • 1,294 Sq Ft
  • Built 1989

  Last Sold Summary

  • 4% Below List Price
  • $267/SF
  • 21 Days On Market

  Current Estimated Value $365,637

  Last Listing Agent Joseph Paoli Howard Hanna Rand Realty

  4407 Whispering Hills Dr, Chester, NY 10918
• 

  Est $449,812 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,570 Sq Ft

  33 Trotting Dr, Chester, NY 10918

  33 Trotting Dr, Chester, NY 10918
• 

  $222,000 Sold Nov 21, 2025

  42 Heaton Rd, Monroe, NY 10950

  • 2 Beds
  • 1 Bath
  • 484 Sq Ft
  • Built 1950

  Last Sold Summary

  • 1% Below List Price
  • $459/SF
  • 63 Days On Market

  Last Listing Agent Maureen Schroder Keller Williams Valley Realty

  42 Heaton Rd, Monroe, NY 10950
• 

  Est $499,118 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,872 Sq Ft

  62 Surrey Rd, Chester, NY 10918

  62 Surrey Rd, Chester, NY 10918

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