Chester, NY Homes

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  $399,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 1,698 Sq Ft

  451 Meri Ln, Monroe, NY 10950

  *Highest and best offers are due Thursday November 13th by 6pm. Welcome to the most current phase of Windridge built in 2001. This rare end unit with basement sits in a premium location backing to hundreds of acres of woods as your backdrop. If you love the outdoors, you just hit a home run by clicking into this new listing. You can hike the Appalachian Trail right outside your front door without

  Gary Silberstein Keller Williams Valley Realty

  451 Meri Ln, Monroe, NY 10950
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  /2

  $87,500 Sold Aug 18, 2025

  L7 Atateka Dr, Chester, NY 12817

  • Land
  • 6.38 Acres
  • $13,715 per Acre

  Last Sold Summary

  • 47% Below List Price
  • 608 Days On Market

  Last Listing Agent Jill Brady Hunt ERA

  L7 Atateka Dr, Chester, NY 12817
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  Est $455,407 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,880 Sq Ft

  66 Pewter Cir, Chester, NY 10918

  66 Pewter Cir, Chester, NY 10918
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  /33

  $295,000

  • 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
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  $334,900 Sold Jun 20, 2025

  1610 Whispering Hills, Chester, NY 10918

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

  Last Sold Summary

  • 6% Below List Price
  • $252/SF
  • 185 Days On Market

  Current Estimated Value $344,999

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  1610 Whispering Hills, Chester, NY 10918
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  Est $539,647 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,623 Sq Ft

  51 Pewter Cir, Chester, NY 10918

  51 Pewter Cir, Chester, NY 10918
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  $369,900 Pending

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  18 Oakland Ave, Chester, NY 10918

  This is a "Neat as a pin" ranch in the Village of Chester. The kitchen has many updated appliances and a custom pantry with large pull-out drawers. The Living room wood floors were refinished and are immaculate. The bathroom has been updated and built to be ADA-compliant with a space-saving "pocket door." There is a large shed in the backyard, all near all the activities the Village has to offer.

  Claude Brischoux Keller Williams Realty

  18 Oakland Ave, Chester, NY 10918
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  $320,000 Sold Dec 12, 2025

  2317 Whispering Hills, Chester, NY 10918

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft
  • Built 1984

  Last Sold Summary

  • 7% Above List Price
  • $299/SF
  • 20 Days On Market

  Last Listing Agent Jeffrey Morrissey HomeSmart Homes & Estates

  2317 Whispering Hills, Chester, NY 10918
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  Est $526,207 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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  $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
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  $845,000 Sold Dec 18, 2025

  11 Saddle Hill Rd, Chester, NY 10918

  • 4 Beds
  • 4 Baths
  • 3,489 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Below List Price
  • $242/SF
  • 97 Days On Market

  Last Listing Agent Alissa Taylor-Vetell Keller Williams Realty

  11 Saddle Hill Rd, Chester, NY 10918
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  Est $693,055 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
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  $500,000

  • 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
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  $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 $572,816

  Last Listing Agent Kevin Tuhy Keller Williams Realty

  21 Jeffrey Dr, Chester, NY 10918
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  Est $601,284 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
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  $699,990

  • 4 Beds
  • 3 Baths
  • 1,867 Sq Ft

  34 Mountainside Dr, Chester, NY 10918

  ONE LEVEL LIVING/ EASY COMMUTE- with additional space upstairs and down! ... Don't miss this beautiful TURN-KEY Arts & Crafts-style FARMHOUSE TO BE BUILT! ..... COME AND FULLY CUSTOMIZE this 4-bdrm, 3 bath, 2,106+/- sq. ft home (including bonus room)! LARGE MAIN FLOOR PRIMARY BEDROOM with ENSUITE BATH & WALK-IN CLOSET plus A SECOND MAIN FLOOR BEDROOM (NURSERY, OFFICE, CRAFT ROOM ETC.).

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, Chester, NY 10918
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  $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 $323,651

  Last Listing Agent Anita S. Cristiano HomeSmart Homes & Estates

  2706 Whispering Hills, Chester, NY 10918
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  Est $698,110 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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  /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
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  $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

  Last Listing Agent Nicholas Carbone HomeSmart Homes & Estates

  15 Mari Rd, Chester, NY 10918
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  Est $349,452 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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  $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
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  $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 $400,918

  Last Listing Agent Harmoni VanEtten eXp Realty

  7 Garden St, Chester, NY 10918
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  Est $367,145 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
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  /40

  $849,000

  • 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
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  $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 $700,180

  Last Listing Agent Virginia Corbett eXp Realty

  2 Laura Dr, Chester, NY 10918
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  Est $402,449 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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  $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
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  $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 $375,319

  Last Listing Agent Hershel Lowy Master Realty Group Inc.

  3911 Whispering Hills, Chester, NY 10918
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  Est $370,561 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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  /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
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  $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
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  Est $582,766 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
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  /5

  $35,000

  • 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
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  $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 $539,182

  Last Listing Agent Luanne McGann Century 21 Full Service Realty

  16 Ayr Rd, Chester, NY 10918
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  Est $483,363 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
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  /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
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  $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 $384,218

  Last Listing Agent Tristen Sierra Coldwell Banker Realty

  1003 Whispering Hills, Chester, NY 10918
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  Est $669,441 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
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  /34

  $470,000 Pending

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

  24 Oak Dr, Monroe, NY 10950

  Enjoy this sunlit Ranch featuring a full walk-out basement and a bright, open layout. The kitchen has been beautifully updated with new cabinetry, granite countertops, and stainless steel appliances. A spacious dining room is perfect for gatherings, and the huge living room offers plenty of natural light through large windows. Hardwood floors throughout the main level.The primary bedroom

  Jay Himelson Howard Hanna Rand Realty

  24 Oak Dr, Monroe, NY 10950

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