Chester, NY Homes

• 

  $560,000 Sold Aug 19, 2025

  21 Jeffrey Dr, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • Built 1993

  Last Sold Summary

  • 6% Above List Price
  • $250/SF
  • 37 Days On Market

  Current Estimated Value $567,180

  Last Listing Agent Kevin Tuhy Keller Williams Realty

  21 Jeffrey Dr, Chester, NY 10918
• 

  Est $582,627 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

  • 21% Above List Price
  • $223/SF
  • 102 Days On Market

  Last Sold Price $480,000

  Last Listing Agent Jorge Vasquez Vasquez Realty
• 

  

  

  /28

  $305,000

  • 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
• 

  $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 $309,205

  Last Listing Agent Anita S. Cristiano HomeSmart Homes & Estates

  2706 Whispering Hills, Chester, NY 10918
• 

  Est $683,066 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

  • $240/SF
  • 60 Days On Market

  Last Sold Price $685,000

  Last Listing Agent Lisa McAteer Scranton Wilkes Barre Regional
• 

  

  /25

  $375,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,355 Sq Ft

  4116 Whispering Hills, Chester, NY 10918

  Beautifully updated 3-bedroom, 2.5-bath Dogwood model townhouse located in Whispering Hills, a desirable corner unit setting. This home offers a perfect blend of comfort and modern upgrades.Step inside to find a thoughtfully refreshed interior with remodeled and freshly painted bathrooms, along with a bright, open layout. The kitchen is equipped with a brand-new refrigerator and dishwasher,

  Michael Casarella William Raveis-New York, LLC

  4116 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 $492,362

  Last Listing Agent Nicholas Carbone HomeSmart Homes & Estates

  15 Mari Rd, Chester, NY 10918
• 

  Est $344,392 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

  • 3% Above List Price
  • $243/SF
  • 39 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Jeffrey Freundlich Howard Hanna Rand Realty
• 

  

  /46

  $849,999

  • 5 Beds
  • 5.5 Baths
  • 5,403 Sq Ft

  4 Debbie Ct, Chester, NY 10918

  DISCOVER THE EPITOME OF LUXURY LIVING! With 5400 sq ft of breathtaking property, where every corner is designed for both elegance and practicality!! With expansive living areas, high-end finishes, and modern amenities, this home is perfect for entertaining or enjoying quiet moments. Embrace a lifestyle of comfort and sophistication in a space that truly feels like a retreat all year

  Joseph Rosenfeld Flag Realty Group

  4 Debbie Ct, 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 $395,588

  Last Listing Agent Harmoni VanEtten eXp Realty

  7 Garden St, Chester, NY 10918
• 

  Est $342,558 Not Listed For Sale

  253 Heritage Ln, Monroe, NY 10950

  • 3 Beds
  • 1.5 Baths
  • 1,376 Sq Ft
  • Built 1988

  253 Heritage Ln, Monroe, NY 10950

  Last Sold Summary

  • 20% Above List Price
  • $207/SF
  • 207 Days On Market

  Last Sold Price $285,000

  Last Listing Agent Joseph Rubeo Keller Williams Hudson Valley
• 

  

  /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
• 

  $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 $671,858

  Last Listing Agent Virginia Corbett eXp Realty

  2 Laura Dr, Chester, NY 10918
• 

  Est $354,154 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

  • 16% Above List Price
  • $192/SF
  • 17 Days On Market

  Last Sold Price $305,000

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

  

  /50

  $580,000 Open Sun 12AM - 2PM

  • 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
• 

  $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 $375,571

  Last Listing Agent Hershel Lowy Master Realty Group Inc.

  3911 Whispering Hills, Chester, NY 10918
• 

  Est $373,918 Not Listed For Sale

  225 Eagleton Dr, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,694 Sq Ft
  • Built 1997

  225 Eagleton Dr, Monroe, NY 10950

  Last Sold Summary

  • 10% Above List Price
  • $201/SF
  • 30 Days On Market

  Last Sold Price $340,000

  Last Listing Agent Theresa Budich Howard Hanna Rand Realty
• 

  

  /50

  $1,725,000

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

  20 Goshen Rd, Chester, NY 10918

  THE ULTIMATE HUDSON VALLEY LEGACY ESTATE | 53 ACRES OF UNMATCHED POTENTIAL Rarely does a property emerge that perfectly balances refined luxury living with raw, untapped opportunity. Nestled in the heart of scenic Chester, New York, 20 Goshen Road offers an expansive 53-acre canvas designed for the visionary. Whether you envision a world-class equestrian facility, a high-potential residential

  Ramanjit Dhanoa eXp Realty

  20 Goshen Rd, Chester, NY 10918
• 

  $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 $628,251

  Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

  18 Grant Dr, Monroe, NY 10950
• 

  Est $376,739 Not Listed For Sale

  152 Eagleton Dr, Monroe, NY 10950

  • 2 Beds
  • 2.5 Baths
  • 1,490 Sq Ft
  • Built 1987

  152 Eagleton Dr, Monroe, NY 10950

  Last Sold Summary

  • 1% Below List Price
  • $254/SF
  • 20 Days On Market

  Last Sold Price $379,000

  Last Listing Agent Alissa Taylor-Vetell Keller Williams Realty
• 

  

  /35

  $725,000 Open Sat 12PM - 3PM

  • 6 Beds
  • 3.5 Baths
  • 4,204 Sq Ft

  487 Black Meadow Rd, Chester, NY 10918

  A Landmark Farmhouse with a Story to Tell.Standing proudly since 1872, this historic Colonial farmhouse is one of the very first homes built on Black Meadow Road and remains a meaningful piece of Chester’s agricultural past. Once surrounded by hundreds of acres of open farmland and dairy cows, the home still carries the soul of a working farm while offering the comforts of modern living. With

  Dominic Santagato Joseph Baratta Company Realty

  487 Black Meadow 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 $530,793

  Last Listing Agent Luanne McGann Century 21 Full Service Realty

  16 Ayr Rd, Chester, NY 10918
• 

  Est $598,529 Not Listed For Sale

  14 Jeffrey Dr, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 2,117 Sq Ft
  • Built 1987

  14 Jeffrey Dr, Chester, NY 10918

  Last Sold Summary

  • 8% Above List Price
  • $261/SF
  • 37 Days On Market

  Last Sold Price $552,000

  Last Listing Agent Savannah Miceli Century 21 Alliance Rlty Group
• 

  

  /23

  $425,000

  • 2 Beds
  • 1 Bath
  • 1,026 Sq Ft

  7 Hambletonian Ave, Chester, NY 10918

  Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay window create a bright, welcoming atmosphere. Wall sconces add a soft glow, and a wall A/C unit ensures comfort throughout the warmer months. The eat

  William Scolza HomeSmart Homes & Estates

  7 Hambletonian Ave, Chester, NY 10918
• 

  $520,000 Sold Feb 11, 2026

  80 Pewter Cir, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,946 Sq Ft
  • Built 2006

  Last Sold Summary

  • 3% Below List Price
  • $267/SF
  • 25 Days On Market

  Current Estimated Value $527,635

  Last Listing Agent Julie Klein BHG Real Estate Green Team

  80 Pewter Cir, Chester, NY 10918
• 

  Est $463,612 Not Listed For Sale

  19 Well Sweep Ln, Chester, NY 10918

  • 2 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1987

  19 Well Sweep Ln, Chester, NY 10918

  Last Sold Summary

  • 26% Above List Price
  • $224/SF
  • 52 Days On Market

  Last Sold Price $369,000

  Last Listing Agent Donna Brunell RE/MAX Benchmark Realty Group
• 

  

  /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
• 

  /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

  Current Estimated Value $112,500

  Last Listing Agent Michelle Decoteau KW Platform

  6 E Shore Dr, Chester, NY 12817
• 

  Est $633,450 Not Listed For Sale

  51 Well Sweep Ln, Chester, NY 10918

  • 3 Beds
  • 3 Baths
  • 2,075 Sq Ft
  • Built 1985

  51 Well Sweep Ln, Chester, NY 10918

  Last Sold Summary

  • 6% Above List Price
  • $289/SF
  • 39 Days On Market

  Last Sold Price $598,800

  Last Listing Agent Claudia Vaccaro Howard Hanna Rand Realty
• 

  

  /26

  $744,999

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

  5 Bens Way, Chester, NY 10918

  Welcome to 5 Bens Way, a beautifully positioned residence tucked away on a quiet cul-de-sac in the highly sought-after Town of Chester, New York. This property offers an exceptional blend of privacy, space, and convenience, making it an outstanding opportunity for buyers seeking a well-rounded Hudson Valley lifestyle with easy access to modern amenities, commuter routes, and recreational

  Anthony Rivas Keller Williams Hudson Valley

  5 Bens Way, Chester, NY 10918
• 

  $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 $283,398 Not Listed For Sale

  1103 Deerfield Rd, Monroe, NY 10950

  • 3 Beds
  • 1.5 Baths
  • 1,240 Sq Ft
  • Built 1979

  1103 Deerfield Rd, Monroe, NY 10950

  Last Sold Summary

  • 13% Above List Price
  • $202/SF
  • 76 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Michael Chang Howard Hanna Rand Realty
• 

  

  /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
• 

  

  /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 $655,452

  Last Listing Agent Sandra Cassio Robert DeFalco Realty, Inc.

  1 Hillview Terrace, Chester, NY 10918
• 

  Est $312,933 Not Listed For Sale

  1004 Swan Hollow Rd, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,334 Sq Ft
  • Built 1979

  1004 Swan Hollow Rd, Monroe, NY 10950

  Last Sold Summary

  • 12% Above List Price
  • $210/SF
  • 175 Days On Market

  Last Sold Price $280,000

  Last Listing Agent Andrea Rose Keller Williams Hudson Valley
• 

  

  /22

  $68,900

  • Land
  • 3.37 Acres
  • $20,445 per Acre

  86 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

  86 Carriage Knoll Rd, Chester, NY 12817
• 

  $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 $307,589

  Last Listing Agent Hershel Lowy Master Realty Group Inc.

  3107 Whispering Hills, Chester, NY 10918
• 

  Est $312,148 Not Listed For Sale

  901 Swan Hollow Rd, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,334 Sq Ft
  • Built 1979

  901 Swan Hollow Rd, Monroe, NY 10950

  Last Sold Summary

  • 4% Above List Price
  • $225/SF
  • 40 Days On Market

  Last Sold Price $300,000

  Last Listing Agent William Fowlkes Howard Hanna Rand Realty
• 

  

  /38

  $350,000

  • 2 Beds
  • 1 Bath
  • 1,272 Sq Ft

  307 Gibson Hill Rd, Chester, NY 10918

  Looking for a solid built home with great bones and a lot of space in the Warwick School District? This spacious ranch home is waiting for your modern touches. Built strong, this home is in need of some cosmetic updates but you can live in the home and enjoy it as you go. This home offers 2 bedrooms (plus a den) and a full bath. The kitchen makes every square inch count with ample storage and

  Donna Gennaro Howard Hanna Rand Realty

  307 Gibson Hill Rd, Chester, NY 10918
• 

  $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 $669,418

  Last Listing Agent Jake Garay Serhant LLC

  138 Dug Rd, Chester, NY 10918

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