Chester, NY Homes

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  $299,000

  • 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
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  $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 $811,648

  Last Listing Agent Kimberly Corkum Keller Williams Realty

  152 Gibson Hill Rd, Chester, NY 10918
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  Est $520,133 Not Listed For Sale

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

  26 Harding Way, Monroe, NY 10950

  26 Harding Way, Monroe, NY 10950
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  $1,399,999

  • 4 Beds
  • 4 Baths
  • 4,508 Sq Ft

  145 Kings Highway Bypass, Chester, NY 10918

  A Refined Custom Estate in One of Warwick’s Most Coveted Enclaves. Set on 3.8 private acres and surrounded by similarly distinguished luxury residences, this exceptional custom home offers the rare balance of architectural elegance, lifestyle amenities, and commuter convenience—located within the highly regarded Warwick School District. Offering over 4,500 square feet of beautifully finished

  Courtney Tablante Keller Williams Realty

  145 Kings Highway Bypass, Chester, NY 10918
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  $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
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  Est $523,023 Not Listed For Sale

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

  67 Washington Rd, Monroe, NY 10950

  67 Washington Rd, Monroe, NY 10950
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  $999,000

  • 5 Beds
  • 4 Baths
  • 5,080 Sq Ft

  4 Camelback Rd, Chester, NY 10918

  Welcome home to 4 Camelback Road. Nestled on a serene cul-de-sac in the executive subdivision of Country Woods, this magnificent home sits on one of the most beautiful streets within the sought-after Monroe-Woodbury School District. Step into perfection as you enter the grand foyer and are immediately welcomed by a light-filled, open floor plan that exudes elegance and sophistication. This

  Alexander Fayn Prominent Properties Sotheby's

  4 Camelback Rd, Chester, NY 10918
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  $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 $692,456

  Last Listing Agent Michele Tobin Keller Williams Realty

  174 Creamery Pond Rd, Chester, NY 10918
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  Est $550,062 Not Listed For Sale

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

  2 Tyler Place, Monroe, NY 10950

  2 Tyler Place, Monroe, NY 10950
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  $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
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  $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 $473,958

  Last Listing Agent Eliezer Safdie Sage Realty Center LLC

  559 Laroe Rd, Chester, NY 10918
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  Est $547,532 Not Listed For Sale

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

  63 Pickerel Rd, Monroe, NY 10950

  63 Pickerel Rd, Monroe, NY 10950
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  $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
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  $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 $464,038

  Last Listing Agent Ryan Degnan Howard Hanna Rand Realty

  12 Mari Rd, Chester, NY 10918
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  Est $486,764 Not Listed For Sale

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

  17 Surrey Rd, Chester, NY 10918

  17 Surrey Rd, Chester, NY 10918
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  $309,900

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

  1503 Whispering Hills, Chester, NY 10918

  Lowest priced 3 Bedroom in the complex! This 3 bedroom 2.1 bath end unit is move in with some tlc needed to make it shine! Put your DIY skills to good use! 2 car garage, private patio, central air. Community pool, tennis, playground. close to bus stop, pool and amenities. Easy access to highways Route 17 and the NYS Thruway.

  Darlene Provino Century 21 E & M Williams Rlty

  1503 Whispering Hills, Chester, NY 10918
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  $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 $357,059

  Last Listing Agent Ernie Acampora River Realty Services, Inc.

  326 Heritage Ln, Monroe, NY 10950
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  Est $498,142 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
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  $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
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  $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 $764,006

  Last Listing Agent Randolph Rogers eXp Realty

  2 Grand View Terrace, Chester, NY 10918
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  Est $703,659 Not Listed For Sale

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

  69 Dug Rd, Chester, NY 10918

  69 Dug Rd, Chester, NY 10918
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  $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

  Current Estimated Value $612,284

  Last Listing Agent Hershel Lowy Master Realty Group Inc.

  114 Old Mansion Rd, Chester, NY 10918
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  Est $688,732 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
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  $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 $762,744

  Last Listing Agent Moses Schreiber MS Realty Group USA, Inc

  56 Sunset Ridge Rd, Monroe, NY 10950
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  Est $610,662 Not Listed For Sale

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

  73 Dug Rd, Chester, NY 10918

  73 Dug Rd, Chester, NY 10918
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  $669,000 Sold Jan 12, 2026

  2 Dawn Ct, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,092 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Below List Price
  • $216/SF
  • 76 Days On Market

  Last Listing Agent Dulce M Ferrera Keller Williams Hudson Valley

  2 Dawn Ct, Chester, NY 10918
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  Est $508,601 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
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  $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
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  Est $571,639 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
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  $612,500 Sold Sep 05, 2025

  81 Hambletonian Rd, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,938 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Below List Price
  • $316/SF
  • 23 Days On Market

  Current Estimated Value $641,674

  Last Listing Agent Dean Diltz Keller Williams Realty

  81 Hambletonian Rd, Chester, NY 10918
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  Est $626,785 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
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  $480,000 Sold Jan 26, 2026

  24 Oak Dr, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 1,662 Sq Ft
  • Built 1965

  Last Sold Summary

  • 2% Above List Price
  • $289/SF
  • 35 Days On Market

  Last Listing Agent Jay Himelson Howard Hanna Rand Realty

  24 Oak Dr, Monroe, NY 10950
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  Est $432,346 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
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  $41,500 Sold Apr 28, 2025

  L34 Lane Rd, Chester, NY 12853

  • Land
  • 3.54 Acres
  • $11,723 per Acre

  Last Sold Summary

  • 5% Below List Price
  • 27 Days On Market

  Last Listing Agent Julia Pucciarelli Gallo Realty ADK Inc

  L34 Lane Rd, Chester, NY 12853
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  Est $453,123 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
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  $338,000 Sold May 15, 2025

  4120 Whispering Hills Dr, Chester, NY 10918

  • 2 Beds
  • 1.5 Baths
  • 1,282 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Below List Price
  • $264/SF
  • 69 Days On Market

  Last Listing Agent Joseph Paoli Howard Hanna Rand Realty

  4120 Whispering Hills Dr, Chester, NY 10918
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  Est $507,361 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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  $499,000 Sold Oct 23, 2025

  358 Bull Mill Rd, Chester, NY 10918

  • 5 Beds
  • 2.5 Baths
  • 3,120 Sq Ft
  • Built 1840

  Last Sold Summary

  • $160/SF
  • 40 Days On Market

  Current Estimated Value $538,377

  Last Listing Agent Amy Wilhelm Corcoran Baer & McIntosh

  358 Bull Mill Rd, Chester, NY 10918
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  Est $483,753 Not Listed For Sale

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

  30 Trotting Dr, Chester, NY 10918

  30 Trotting Dr, Chester, NY 10918
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  $420,000 Sold Apr 07, 2025

  31 Darin Rd, Warwick, NY 10990

  • 3 Beds
  • 2.5 Baths
  • 2,067 Sq Ft
  • Built 1987

  Last Sold Summary

  • 9% Above List Price
  • $203/SF
  • 24 Days On Market

  Current Estimated Value $424,166

  Last Listing Agent Devon King HomeSmart Homes & Estates

  31 Darin Rd, Warwick, NY 10990

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