Chester, NY Homes

• 

  $315,000 Sold May 06, 2025

  2706 Whispering Hills, Chester, NY 10918

  • 2 Beds
  • 1.5 Baths
  • 1,086 Sq Ft
  • Built 1984

  Last Sold Summary

  • $290/SF
  • 72 Days On Market

  Current Estimated Value $322,043

  Last Listing Agent Anita S. Cristiano HomeSmart Homes & Estates

  2706 Whispering Hills, Chester, NY 10918
• 

  Est $542,289 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,210 Sq Ft

  53 Pewter Cir, Chester, NY 10918

  53 Pewter Cir, Chester, NY 10918
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  /33

  $289,500

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  1401 Whispering Hills, Chester, NY 10918

  Discover the perfect blend of comfort, convenience, and community in this 2-bedroom, 1-bath end-unit townhouse. Situated in a quiet corner of the neighborhood, this home offers extra privacy and natural light, along with the added benefit of an attached 1-car garage for secure parking and storage. Inside, you'll find a thoughtfully designed layout that maximizes space and livability - ideal for

  Debbie Goldstein Howard Hanna Rand Realty

  1401 Whispering Hills, Chester, NY 10918
• 

  $500,000 Sold Oct 20, 2025

  15 Mari Rd, Chester, NY 10918

  • 4 Beds
  • 2 Baths
  • 1,888 Sq Ft
  • Built 1971

  Last Sold Summary

  • $265/SF
  • 56 Days On Market

  Current Estimated Value $490,747

  Last Listing Agent Nicholas Carbone HomeSmart Homes & Estates

  15 Mari Rd, Chester, NY 10918
• 

  Est $707,530 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,223 Sq Ft

  15 Pewter Cir, Chester, NY 10918

  15 Pewter Cir, Chester, NY 10918
• 

  

  /3

  $699,000

  • Land
  • 2 Acres
  • $349,500 per Acre

  50 Elkay Dr, Chester, NY 10918

  Last remaining parcel available on Elkay Drive in the Chester Industrial Park.This 2-acre industrial lot was previously fully approved for a two-story building with loading docks. While approvals expired approximately 10 years ago, the site’s industrial potential remains strong. Both adjacent parcels are currently under development, with 30,000+ SF warehouse facilities being constructed,

  Leib Glanz Point Realty USA

  50 Elkay Dr, Chester, NY 10918
• 

  $400,000 Sold Jul 28, 2025

  7 Garden St, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,435 Sq Ft
  • Built 1900

  Last Sold Summary

  • $279/SF
  • 25 Days On Market

  Current Estimated Value $402,227

  Last Listing Agent Harmoni VanEtten eXp Realty

  7 Garden St, Chester, NY 10918
• 

  Est $602,645 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,156 Sq Ft

  11 Pewter Cir, Chester, NY 10918

  11 Pewter Cir, Chester, NY 10918
• 

  

  /22

  $465,000

  • 4 Beds
  • 1.5 Baths
  • 1,932 Sq Ft

  3 Tulip Ln, Monroe, NY 10950

  Spacious raised ranch style home offering three bedrooms and two full bathrooms with 1,932 square feet of comfortable living space. Features a 1-car garage and a functional layout perfect for everyday living. The home has been freshly painted, giving it a bright, clean, move-in ready feel. A great opportunity for buyers seeking space, style, and value.

  Geni Silva Ethos Realty LLC

  3 Tulip Ln, Monroe, NY 10950
• 

  $690,000 Sold Jul 09, 2025

  2 Laura Dr, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,592 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Above List Price
  • $266/SF
  • 31 Days On Market

  Current Estimated Value $690,657

  Last Listing Agent Virginia Corbett eXp Realty

  2 Laura Dr, Chester, NY 10918
• 

  Est $708,690 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,849 Sq Ft

  16 Pewter Cir, Chester, NY 10918

  16 Pewter Cir, Chester, NY 10918
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  /34

  $999,000

  • 5 Beds
  • 4 Baths
  • 3,136 Sq Ft

  12 Damian Ct, Chester, NY 10918

  Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second

  Elimelech Kremer MS Realty Group USA, Inc

  12 Damian Ct, Chester, NY 10918
• 

  $367,500 Sold Aug 29, 2025

  3911 Whispering Hills, Chester, NY 10918

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

  Last Sold Summary

  • 1% Above List Price
  • $279/SF
  • 25 Days On Market

  Current Estimated Value $368,778

  Last Listing Agent Hershel Lowy Master Realty Group Inc.

  3911 Whispering Hills, Chester, NY 10918
• 

  Est $349,989 Not Listed For Sale

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

  274 Heritage Ln, Monroe, NY 10950

  274 Heritage Ln, Monroe, NY 10950
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  /33

  $89,500

  • Land
  • 12.79 Acres
  • $6,998 per Acre

  3-4 Adirondack Heights Rd, Chester, NY 12817

  Seller financing now available. 12.79 acres of mixed forest and wetlands. Perc tests and engineered plot plans have been completed. APA approved building sites with well & septic locations identified. (2-lots can each be built upon or just have one large lot) Power at the road pedestal box. Tons of hemlock, spruce, and pine trees throughout. Close to Chestertown, 20-minutes to Gore Mountain or

  Walter Swartz Gallo Realty ADK Inc

  3-4 Adirondack Heights Rd, Chester, NY 12817
• 

  $610,000 Sold Sep 19, 2025

  18 Grant Dr, Monroe, NY 10950

  • 4 Beds
  • 2.5 Baths
  • 2,144 Sq Ft
  • Built 1994

  Last Sold Summary

  • 6% Above List Price
  • $285/SF
  • 27 Days On Market

  Current Estimated Value $618,080

  Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

  18 Grant Dr, Monroe, NY 10950
• 

  Est $358,306 Not Listed For Sale

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

  253 Heritage Ln, Monroe, NY 10950

  253 Heritage Ln, Monroe, NY 10950
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  /38

  $500,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,098 Sq Ft

  16 Mari Rd, Chester, NY 10918

  Set back on a quiet street, just steps from downtown Sugar Loaf is this large home on almost an acre. Walk into the open living room and dining room, open to the kitchen with stainless steel appliances. The primary bedroom has access to the back deck, perfect for sipping your morning coffee overlooking the large peaceful backyard. Two additional bedrooms and a full bath complete the main floor.

  Kimberly Corkum Keller Williams Realty

  16 Mari Rd, Chester, NY 10918
• 

  $536,000 Sold Aug 06, 2025

  16 Ayr Rd, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft
  • Built 1972

  Last Sold Summary

  • 9% Above List Price
  • $312/SF
  • 62 Days On Market

  Current Estimated Value $541,023

  Last Listing Agent Luanne McGann Century 21 Full Service Realty

  16 Ayr Rd, Chester, NY 10918
• 

  Est $362,236 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,585 Sq Ft

  245 Heritage Ln, Monroe, NY 10950

  245 Heritage Ln, Monroe, NY 10950
• 

  

  /23

  $369,000 Pending

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

  2915 Whispering Hills Unit 596, Chester, NY 10918

  Welcome to your next home in the highly desirable Whispering Hills community! Completely renovated in 2025, this end-unit with a 2-car garage features new flooring on the main level, gleaming hardwood floors upstairs, a modern kitchen with stainless steel appliances, updated bathrooms, recessed lighting throughout, high ceilings, and beautiful modern chandeliers. The bright, open layout includes

  Johanna Monzon Ruballos Century 21 Full Service Realty

  2915 Whispering Hills Unit 596, Chester, NY 10918
• 

  $369,900 Sold Feb 18, 2025

  1003 Whispering Hills, Chester, NY 10918

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

  Last Sold Summary

  • $278/SF
  • 48 Days On Market

  Current Estimated Value $383,866

  Last Listing Agent Tristen Sierra Coldwell Banker Realty

  1003 Whispering Hills, Chester, NY 10918
• 

  Est $391,441 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,694 Sq Ft

  225 Eagleton Dr, Monroe, NY 10950

  225 Eagleton Dr, Monroe, NY 10950
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  /28

  $319,000

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

  3917 Whispering Hills, Chester, NY 10918

  Welcome to Whispering Hills! This beautifully maintained home features a galley kitchen with stainless steel appliances and a convenient in-unit washer and dryer. The first level offers a stylish half bath and well-kept flooring throughout the kitchen, dining room, and living room. Enjoy cozy evenings by the fireplace, and extend your living space outdoors on the private patio. Upstairs, you’ll

  Jie Liu Keller Williams Hudson Valley

  3917 Whispering Hills, Chester, NY 10918
• 

  /2

  $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
• 

  Est $380,862 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,490 Sq Ft

  152 Eagleton Dr, Monroe, NY 10950

  152 Eagleton Dr, Monroe, NY 10950
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  /14

  $144,900

  • Land
  • 0.47 Acre
  • $308,298 per Acre

  L31 Clarkson Rd, Chester, NY 12817

  Build Your Adirondack Getaway on Loon Lake!Enjoy beach rights on beautiful Loon Lake with this just-under-half-acre lot, the perfect spot to create your own year-round retreat or seasonal escape. Whether you dream of summer days by the water, paddling and swimming, or cozy winter weekends in the mountains, this property offers an ideal starting point for your Adirondack lifestyle.

  Brooke Clark Four Seasons Sotheby's International Realty

  L31 Clarkson Rd, Chester, NY 12817
• 

  $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
• 

  Est $593,619 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,117 Sq Ft

  14 Jeffrey Dr, Chester, NY 10918

  14 Jeffrey Dr, Chester, NY 10918
• 

  

  /50

  $580,000

  • 4 Beds
  • 2.5 Baths
  • 2,112 Sq Ft

  150 Lake Region Blvd, Monroe, NY 10950

  Welcome to 150 Lake Region Blvd — a well-maintained home located in Monroe’s desirable Lake Region / Walton Park area. The moment you step inside, you’re greeted by warm hardwood floors and an open, comfortable layout that feels welcoming without being overwhelming. The home offers a natural flow from room to room, making everyday living and entertaining easy and functional. With 4 oversized

  Pete Wolven Hudson Valley Home Connection

  150 Lake Region Blvd, Monroe, NY 10950
• 

  $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
• 

  Est $481,765 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,650 Sq Ft

  19 Well Sweep Ln, Chester, NY 10918

  19 Well Sweep Ln, Chester, NY 10918
• 

  

  /19

  $74,900

  • Land
  • 4.05 Acres
  • $18,494 per Acre

  85 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

  85 Carriage Knoll Rd, Chester, NY 12817
• 

  $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 $705,163

  Last Listing Agent Jake Garay Serhant LLC

  138 Dug Rd, Chester, NY 10918
• 

  Est $668,555 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,075 Sq Ft

  51 Well Sweep Ln, Chester, NY 10918

  51 Well Sweep Ln, Chester, NY 10918
• 

  /2

  $799,999 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft

  5 Bens Way, Chester, NY 10918

  On Market Monday 2/9/2026

  Anthony Rivas Keller Williams Hudson Valley

  5 Bens Way, Chester, NY 10918
• 

  $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 $306,536

  Last Listing Agent Annmarie Kovacs Howard Hanna Rand Realty

  4401 Whispering Hills Dr, Chester, NY 10918
• 

  Est $294,456 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
• 

  

  /5

  $35,000 Pending

  • Land
  • 7.07 Acres
  • $4,950 per Acre

  L30 Lane Rd, Chester, NY 12853

  You won't want to miss out on this opportunity! A little over 7 acres (2 parcels) in the heart of the Adirondacks. Close proximity to all the local lakes (Schroon Lake, Loon Lake, Brant Lake) & 10 minutes from Gore Mountain.

  Julia Pucciarelli Gallo Realty ADK Inc

  L30 Lane Rd, Chester, NY 12853
• 

  $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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