Chester, NY Homes

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  /41

  $569,000

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

  78 Pickerel Rd, Monroe, NY 10950

  Beautiful and spacious 4 Bedroom, 2.5 Bath Colonial set on park-like property in a lovely neighborhood with a serene backdrop of mature trees, offering both privacy and a peaceful setting. This home features a large eat-in kitchen with abundant cabinetry, tremendous counter space, and a sliding glass door leading to a newer rear deck—perfect for relaxing or entertaining outdoors.The oversized

  Mary Ann Mitchell eXp Realty

  78 Pickerel Rd, Monroe, NY 10950
• 

  $540,000

  Sold Aug 28, 2025

  1 Winding Trail, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 2,040 Sq Ft
  • Built 1991

  Last Sold Summary

  • 10% Below List Price
  • $265/SF
  • 35 Days On Market

  Current Estimated Value $551,038

  Last Listing Agent Donald Serotta Howard Hanna Rand Realty

  1 Winding Trail, Chester, NY 10918
• 

  Est $433,680

  Not Listed For Sale

  48 Maple Ln, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 1,003 Sq Ft
  • Built 1963

  48 Maple Ln, Monroe, NY 10950

  Last Sold Summary

  • 99 Days On Market
• 

  

  

  /29

  $1,299,000

  • 4 Beds
  • 3.5 Baths
  • 5,712 Sq Ft

  16 Sunset Ridge, Monroe, NY 10950

  Secluded Trout Brook Estate: Expansive 5,700+ Sq Ft, 6-Car Garage, Ready for Multi-Gen Living and Entertaining. Nestled on nearly six private acres in the exclusive Trout Brook Estates, this expansive Colonial-style estate blends classic elegance with modern comfort. Built in 1993 and thoughtfully designed for multi-generational living and refined entertainment, the home offers generous space,

  Carmela Lopez Borrazas Serhant LLC

  16 Sunset Ridge, Monroe, NY 10950
• 

  $610,000

  Sold Aug 25, 2025

  411 Prospect Rd, Chester, NY 10918

  • 4 Beds
  • 2 Baths
  • 1,987 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Above List Price
  • $307/SF
  • 39 Days On Market

  Current Estimated Value $615,951

  Last Listing Agent Dana Posner Howard Hanna Rand Realty

  411 Prospect Rd, Chester, NY 10918
• 

  Est $419,486

  Not Listed For Sale

  68 Evan Rd, Warwick, NY 10990

  • 3 Beds
  • 2.5 Baths
  • 1,452 Sq Ft
  • Built 1995

  68 Evan Rd, Warwick, NY 10990

  Last Sold Summary

  • 39 Days On Market
• 

  

  /50

  $370,000

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

  3815 Whispering Hills Dr, Chester, NY 10918

  Discover your new haven at this charming 3-bedroom, 2.5-bathroom condo nestled in the vibrant community of Chester, NY. Perfect for those looking to infuse a home with their personal style, this residence offers fantastic potential to make it your own. Let your imagination take the reins and make this spacious house into your dream home! The condo is thoughtfully designed with ample room for rest

  David Kraus MK Realty Inc

  3815 Whispering Hills Dr, Chester, NY 10918
• 

  $525,000

  Sold Jul 24, 2025

  11 Vista Dr, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 2,122 Sq Ft
  • Built 1998

  Last Sold Summary

  • 2% Above List Price
  • $247/SF
  • 43 Days On Market

  Current Estimated Value $554,168

  Last Listing Agent James Feldhaus eXp Realty

  11 Vista Dr, Chester, NY 10918
• 

  Est $364,772

  Not Listed For Sale

  27 Darin Rd, Warwick, NY 10990

  • 2 Beds
  • 2.5 Baths
  • 1,276 Sq Ft
  • Built 1987

  27 Darin Rd, Warwick, NY 10990

  Last Sold Summary

  • 28 Days On Market
• 

  

  /38

  $565,000

  Pending

  • 4 Beds
  • 3 Baths
  • 1,846 Sq Ft

  52 Wilson Rd, Monroe, NY 10950

  Welcome to this beautifully maintained 4-bedroom, 3-bath raised ranch in the highly sought-after Lake Hill Farms community, located within the Monroe-Woodbury School District.Upon entry, you’re greeted by an oversized foyer featuring wide stairs updated with stunning hardwood that runs throughout. The main level offers a bright eat-in kitchen with sliding glass doors that open to a deck

  Claudia Lepore Keller Williams Realty

  52 Wilson Rd, Monroe, NY 10950
• 

  $365,000

  Sold Sep 12, 2025

  226 Eagleton Dr, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,698 Sq Ft
  • Built 1997

  Last Sold Summary

  • 3% Below List Price
  • $215/SF
  • 16 Days On Market

  Current Estimated Value $379,439

  Last Listing Agent Lorrainne Pisciotta Weichert Realtors

  226 Eagleton Dr, Monroe, NY 10950
• 

  Est $367,286

  Not Listed For Sale

  25 Darin Rd, Warwick, NY 10990

  • 2 Beds
  • 2.5 Baths
  • 1,276 Sq Ft
  • Built 1987

  25 Darin Rd, Warwick, NY 10990

  Last Sold Summary

  • 96 Days On Market
• 

  

  /5

  $54,900

  $10K PRICE DROP

  • Land
  • 10.14 Acres
  • $5,414 per Acre

  15 Deer Run, Chester, NY 12817

  10+ Acre recreational vacation location in the Town of Chester. Private maintained road with nice camps and homes. The lot feels as if its set in the heart of a wildlife preserve. Small non salvageable cabin on the property that had electric to the site. 6 miles to North Creek the home of Gore Mountain Ski Center. Build your vacation home here in the Adirondacks.

  Patricia Seitz McAlonen Pearsall Realty

  15 Deer Run, Chester, NY 12817
• 

  $869,000

  Sold Jul 24, 2025

  26 W Meadow Way, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 3,100 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $280/SF
  • 85 Days On Market

  Current Estimated Value $119,000

  Last Listing Agent Nancy Sardo BHG Real Estate Green Team

  26 W Meadow Way, Chester, NY 10918
• 

  Est $413,705

  Not Listed For Sale

  31 Darin Rd, Warwick, NY 10990

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

  31 Darin Rd, Warwick, NY 10990

  Last Sold Summary

  • 24 Days On Market
• 

  

  /49

  $595,000

  $55K PRICE DROP Pending

  • 5 Beds
  • 3 Baths
  • 2,983 Sq Ft

  9 Mount Ridge Ct, Monroe, NY 10950

  Spacious Center Hall Colonial offering the perfect blend of comfort, style, and functionality. A dramatic two-story entry welcomes you into this thoughtfully designed home, featuring an open-concept layout ideal for both everyday living and entertaining.The heart of the home is the expansive kitchen, complete with abundant counter space, a large dinette area, and sliding glass doors leading

  Richard Froehlich RE/MAX Benchmark Realty Group

  9 Mount Ridge Ct, Monroe, NY 10950
• 

  $100,000

  Sold Feb 12, 2026

  0 Renies Rd, Chester, NY 10918

  • Land
  • 1.85 Acres
  • $54,054 per Acre

  Last Sold Summary

  • 50% Below List Price
  • 102 Days On Market

  Last Listing Agent Kristie Jacques Century 21 Full Service Realty

  0 Renies Rd, Chester, NY 10918
• 

  Est $815,166

  Not Listed For Sale

  215 Ridge Rd, Chester, NY 10918

  • 3 Beds
  • 3 Baths
  • 3,005 Sq Ft
  • Built 1848

  215 Ridge Rd, Chester, NY 10918

  Last Sold Summary

  • 119 Days On Market
• 

  

  /23

  $68,900

  $19K PRICE INCREASE

  • Land
  • 3.11 Acres
  • $22,154 per Acre

  72 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

  72 Carriage Knoll Rd, Chester, NY 12817
• 

  $525,000

  Sold Sep 02, 2025

  10 Tulip Ln, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 1,758 Sq Ft
  • Built 1961

  Last Sold Summary

  • 3% Below List Price
  • $299/SF
  • 38 Days On Market

  Current Estimated Value $525,074

  Last Listing Agent Philip Szumlaski Keller Williams Realty

  10 Tulip Ln, Monroe, NY 10950
• 

  Est $503,660

  Not Listed For Sale

  201 Hambletonian Rd, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,342 Sq Ft
  • Built 1966

  201 Hambletonian Rd, Chester, NY 10918

  Last Sold Summary

  • 19 Days On Market
• 

  

  /49

  $400,000

  Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,699 Sq Ft

  174 Eagleton Dr Unit 17D, Monroe, NY 10950

  Welcome to this beautifully maintained end-unit townhouse offering serene lakefront living and an exceptional array of community amenities, including a pool, playground, basketball & tennis courts. Freshly painted throughout the first floor and enhanced with elegant crown molding, this home showcases quality finishes and pride of ownership. Attractive vinyl plank flooring extends through the

  Donna Gennaro Howard Hanna Rand Realty

  174 Eagleton Dr Unit 17D, Monroe, NY 10950
• 

  $445,000

  Sold May 21, 2026

  31 Hudson St, Chester, NY 10918

  • 2 Beds
  • 2 Baths
  • 1,998 Sq Ft
  • Built 1947

  Last Sold Summary

  • 1% Below List Price
  • $223/SF
  • 32 Days On Market

  Current Estimated Value $447,795

  Last Listing Agent Geoffrey Green BHG Real Estate Green Team

  31 Hudson St, Chester, NY 10918
• 

  Est $680,210

  Not Listed For Sale

  16 Fernglade Ct, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 3,327 Sq Ft
  • Built 1973

  16 Fernglade Ct, Chester, NY 10918

  Last Sold Summary

  • 12 Days On Market
• 

  

  /38

  $1,200,000

  • 4 Beds
  • 2.5 Baths
  • 2,711 Sq Ft

  63 Whitetail Run, Chester, NY 10918

  This stunning 4 bedroom, 3 bathroom home with a beautifully updated kitchen is the perfect place to call home. With plenty of space to entertain and relax, you'll love the open layout and modern amenities that this home has to offer. Whether you're enjoying a meal in the spacious kitchen or unwinding in the cozy living room, you'll feel right at home in this charming and inviting space.

  Artan Kukaj SPIRAL NY Real Estate LLC

  63 Whitetail Run, Chester, NY 10918
• 

  $655,000

  Sold Feb 18, 2026

  3 Derose Ln, Chester, NY 10918

  • 5 Beds
  • 3.5 Baths
  • 2,550 Sq Ft
  • Built 1997

  Last Sold Summary

  • 1% Above List Price
  • $257/SF
  • 44 Days On Market

  Current Estimated Value $659,129

  Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

  3 Derose Ln, Chester, NY 10918
• 

  Est $773,026

  Not Listed For Sale

  590 Craigville Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,152 Sq Ft
  • Built 2002

  590 Craigville Rd, Chester, NY 10918

  Last Sold Summary

  • 26 Days On Market
• 

  

  /23

  $390,000

  • 3 Beds
  • 1 Bath
  • 1,561 Sq Ft

  33 Meadow Ave, Chester, NY 10918

  One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space. Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk

  Ernie Acampora River Realty Services, Inc.

  33 Meadow Ave, Chester, NY 10918
• 

  $437,000

  Sold Jun 14, 2026

  71 Greycourt Rd, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,056 Sq Ft
  • Built 1957

  Last Sold Summary

  • 10% Above List Price
  • $414/SF
  • 159 Days On Market

  Current Estimated Value $485,957

  Last Listing Agent Lazar Schvimmer Blooming Realty

  71 Greycourt Rd, Chester, NY 10918
• 

  Est $640,834

  Not Listed For Sale

  13 Townsend Place, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,108 Sq Ft
  • Built 1969

  13 Townsend Place, Chester, NY 10918

  Last Sold Summary

  • 25 Days On Market
• 

  

  /10

  $99,995

  Pending

  • Land
  • 22.88 Acres
  • $4,370 per Acre

  1.4 Cobble Creek Rd Unit 4, Chester, NY 12853

  Experience the best of Adirondack living on this scenic 22-acre property in Chester, New York. Accessible year-round from a town-maintained road with power nearby, the land offers several elevated APA-approved building sites perfectly positioned for a private cabin, vacation home, or full-time residence. The property is richly forested with mature Northern hardwoods including maple, oak, birch,

  Marc Christmas CHRISTMAS AND ASSOCIATES INC

  1.4 Cobble Creek Rd Unit 4, Chester, NY 12853
• 

  

  /13

  $300,000

  Sold Dec 23, 2025

  68 Walter Foote Rd, Chester, NY 12853

  • Land
  • 194 Acres
  • $1,546 per Acre

  Last Sold Summary

  • 52% Below List Price
  • 86 Days On Market

  Last Listing Agent Cindy Brower Coldwell Banker Prime Properties

  68 Walter Foote Rd, Chester, NY 12853
• 

  Est $541,297

  Not Listed For Sale

  11 Townsend Place, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,788 Sq Ft
  • Built 1968

  11 Townsend Place, Chester, NY 10918

  Last Sold Summary

  • 28 Days On Market
• 

  

  /22

  $738,850

  Pending

  • Land
  • 561.54 Acres
  • $1,316 per Acre

  234 Old River Rd, Chester, NY 12853

  This property is 562 Ac of Adk field and forest with 2,000 ft. of frontage on the Hudson River, 2 beaver ponds, stream and trails. Structures on this dormant farm include an uninhabited house, barn and shed in need of rehab. An authentic log cabin is situated at a higher elevation above the field, beside an active beaver pond. Adjacent is a 'Morton' building, ideal for storage of equipment and

  John O'Donnell Timberland Realty

  234 Old River Rd, Chester, NY 12853
• 

  $125,000

  Sold Oct 03, 2025

  0 William Hill Rd, Chester, NY 12817

  • Land
  • 45.83 Acres
  • $2,727 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 99 Days On Market

  Last Listing Agent Jason Minch William Raveis-New York LLC

  0 William Hill Rd, Chester, NY 12817
• 

  Est $651,615

  Not Listed For Sale

  509 Laroe Rd, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 2,350 Sq Ft
  • Built 1981

  509 Laroe Rd, Chester, NY 10918

  Last Sold Summary

  • 50 Days On Market
• 

  

  /49

  $425,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,090 Sq Ft

  16 Oakland Ave, Chester, NY 10918

  Charming 4-Bedroom Colonial in the Heart of Hudson Valley. Priced to Sell, tons of potential and great commuter location with close proximity tohighway! Welcome to this spacious 4-bedroom, 2.5-bath home nestled in the picturesque town of Chester, NY, in the heart of the beautifulHudson Valley. Offering 2,090 sq ft of living space, plus a finished rec room with an additional 1,026 sq ft,

  Vikki Garby BHG Real Estate Green Team

  16 Oakland Ave, Chester, NY 10918
• 

  $535,000

  Sold Feb 09, 2026

  219 Bull Mill Rd, Chester, NY 10918

  • 4 Beds
  • 2 Baths
  • 1,928 Sq Ft
  • Built 1960

  Last Sold Summary

  • 2% Above List Price
  • $277/SF
  • 36 Days On Market

  Current Estimated Value $537,971

  Last Listing Agent Claudia Lepore Keller Williams Realty

  219 Bull Mill Rd, Chester, NY 10918
• 

  Est $657,358

  Not Listed For Sale

  16 Bianca Blvd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,192 Sq Ft
  • Built 1987

  16 Bianca Blvd, Chester, NY 10918

  Last Sold Summary

  • 21 Days On Market
• 

  

  /24

  $275,000

  $20K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  2113 Whispering Hills Unit 178, Chester, NY 10918

  Welcome Home! 2 Bedrooms 1 Bathroom move in ready end unit. Recently renovated including a new kitchen with granite counter tops and stainless steel appliances, new bathroom, new windows, new laminate flooring, new water heater, new light fixtures and recessed lighting. Nothing to do but move in! Close to supermarket, post office, restaurants, urgent care, highway. Perfect commuter location.

  Valerie Quinn Keller Williams Realty

  2113 Whispering Hills Unit 178, Chester, NY 10918

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