Chester, NY Homes

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  /2

  $304,900 Pending

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  2912 Whispering Hills, Chester, NY 10918

  Welcome home to this beautifully renovated 2 bedroom, 1 bathroom condo located in the desirable Whispering Hills community. Every detail has been thoughtfully updated to combine modern comfort with timeless style. Step inside to discover a new kitchen featuring gorgeous countertops, contemporary cabinetry, and beautiful stainless steel appliances - perfect for cooking, entertaining, or enjoying

  Rebecca Matta-Candela Keller Williams Realty

  2912 Whispering Hills, Chester, NY 10918
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  /6

  $2,450 per month

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft
  • House for Rent

  2208 Whispering Hills, Chester, NY 10918

  Welcome to 2208 Whispering Hills! This stunning townhouse will capture your heart with its impeccable features and unbeatable location. Step inside and be welcomed by the warm and inviting atmosphere. The main level boasts a beautifully designed open floor plan, allowing for seamless flow between the living room, dining area, and kitchen. Newer tiles in the kitchen, you'll find 2 bedrooms, each

  Mordechai Ungar HFA Realty Group

  2208 Whispering Hills, Chester, NY 10918
• 

  $575,000 Sold Sep 23, 2025

  12 Bianca Blvd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,200 Sq Ft
  • Built 1987

  Last Sold Summary

  • 2% Below List Price
  • $180/SF
  • 126 Days On Market

  Current Estimated Value $611,838

  Last Listing Agent Aoife Freeman Howard Hanna Rand Realty

  12 Bianca Blvd, Chester, NY 10918
• 

  Est $565,915 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,771 Sq Ft

  47 Maple Ave, Chester, NY 10918

  47 Maple Ave, Chester, NY 10918
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  $299,900 Pending

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

  2104 Whispering Hills, Chester, NY 10918

  WHISPERING HILLS!! SOLD AS IS!!! Largest Model! Two Level Living! 3 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Eat In Kitchen! Living Room! Master Bedroom Suite with Walk in Closet! Patio! Country Club Living! Clubhouses! Pools! Tennis! Basket Ball! Tot Lot! Dog Walk! Perfect Commuter Location! Walk to NY Bus! Close to Major Highway & Shopping!

  Amanda Dnistrian ARC Realty 1 in Sales

  2104 Whispering Hills, Chester, NY 10918
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  /13

  $3,000 per month

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft
  • House for Rent

  25 Trotting Dr, Chester, NY 10918

  Welcome to 25 Trotting Drive, located in the heart of Chester, NY. This spacious rental offers the perfect blend of comfort and convenience with plenty of room for everyday living. The home is set in a quiet residential neighborhood, providing a peaceful setting with easy access to local shopping, schools, and major highways. Tenants will be responsible for all utilities. Trash collection & Lawn

  Anthony Rivas Keller Williams Hudson Valley

  25 Trotting Dr, Chester, NY 10918
• 

  $411,000 Sold Jul 08, 2025

  100 Marian Ct, Warwick, NY 10990

  • 3 Beds
  • 2.5 Baths
  • 1,528 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Above List Price
  • $269/SF
  • 26 Days On Market

  Current Estimated Value $422,684

  Last Listing Agent Jennifer DiCostanzo RE/MAX Town & Country

  100 Marian Ct, Warwick, NY 10990
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  Est $515,264 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,956 Sq Ft

  26 Maple Ln, Monroe, NY 10950

  26 Maple Ln, Monroe, NY 10950
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  /5

  $54,900

  • 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
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  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Apartment for Rent

  82 High St Unit 2, Chester, NY 10918

  This ground-floor apartment is ready for occupancy. The Primary bedroom has double closets and can fit a king-sized bed. The Living room/dining room combination is bright and sun-filled, with plenty of windows and a patio overlooking a private wooded area. The flooring is grey vinyl, and there is plush carpet in the bedrooms. The updated kitchen has stainless steel appliances and a subway tile

  Lynda Hoss Weichert Realtors

  82 High St Unit 2, Chester, NY 10918
• 

  $620,000 Sold Oct 29, 2025

  9 June Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,402 Sq Ft
  • Built 1999

  Last Sold Summary

  • 4% Below List Price
  • $258/SF
  • 52 Days On Market

  Last Listing Agent Jason Madison eXp Realty

  9 June Rd, Chester, NY 10918
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  Est $436,939 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,560 Sq Ft

  13 Maple Ln, Monroe, NY 10950

  13 Maple Ln, Monroe, NY 10950
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  /93

  $1,975,000

  • 6 Beds
  • 7.5 Baths
  • 7,034 Sq Ft

  69 Cedar Pond Ln, Chester, NY 10918

  Set on 10 private acres with sweeping mountain views from nearly every room, 69 Cedar Pond is a five-bedroom, eight-bath estate that exemplifies expansive design and contemporary style. The striking A-frame architecture, double-height windows, and soaring ceilings create dramatic, light-filled interiors where every angle frames the surrounding landscape and sunsets.A three-story entry

  Emily Iason Four Seasons Sotheby's Int.

  69 Cedar Pond Ln, Chester, NY 10918
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  /9

  $2,400 per month

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft
  • Townhouse for Rent

  2805 Whispering Hills Unit 573, Chester, NY 10918

  2BD 1.5BA rental in Whispering Hills! This unit has been updated top to bottom, featuring LVP flooring throughout, new refrigerator, new stove and a brand new full bath! The entire space has been professionally painted and feels like new. Updated kitchen including newer cabinets and granite countertops. The master bedroom offers a walk in closet. Washer and dryer in unit and private garage. The

  Joseph Trifono HomeSmart Homes & Estates

  2805 Whispering Hills Unit 573, Chester, NY 10918
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  $335,000 Sold Dec 27, 2024

  274 Heritage Ln, Monroe, NY 10950

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

  Last Sold Summary

  • 4% Above List Price
  • $243/SF
  • 39 Days On Market

  Current Estimated Value $354,555

  Last Listing Agent Jeffrey Freundlich Howard Hanna Rand Realty

  274 Heritage Ln, Monroe, NY 10950
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  Est $505,923 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,104 Sq Ft

  7 Maple Ln, Monroe, NY 10950

  7 Maple Ln, Monroe, NY 10950
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  /23

  $68,900

  • 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
• 

  $310,000 Sold Nov 10, 2025

  3708 Whispering Hills, Chester, NY 10918

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft
  • Built 1990

  Last Sold Summary

  • 5% Above List Price
  • $289/SF
  • 26 Days On Market

  Last Listing Agent Nikki Grzegorzewski Keller Williams Realty

  3708 Whispering Hills, Chester, NY 10918
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  Est $427,700 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,686 Sq Ft

  31 Maple Ln, Monroe, NY 10950

  31 Maple Ln, Monroe, NY 10950
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  /23

  $475,000

  • 4 Beds
  • 2.5 Baths
  • 1,357 Sq Ft

  70 Main St, Chester, NY 10918

  Discover the perfect blend of versatility and charm with this exceptional property. The main house offers three levels of comfortable living, including four bedrooms, three baths, and a spacious kitchen ideal for gathering and entertaining. The thoughtfully renovated barn extends your options with beautifully finished space that carries rustic character alongside modern updates. Whether you

  Kassandra Mott Keller Williams Hudson Valley

  70 Main St, Chester, NY 10918
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  $780,000 Sold Aug 15, 2025

  27 Grand View Terrace, Chester, NY 10918

  • 5 Beds
  • 3.5 Baths
  • 4,490 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Above List Price
  • $174/SF
  • 43 Days On Market

  Current Estimated Value $793,376

  Last Listing Agent Randolph Rogers eXp Realty

  27 Grand View Terrace, Chester, NY 10918
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  Est $417,461 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  43 Maple Ln, Monroe, NY 10950

  43 Maple Ln, Monroe, NY 10950
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  /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
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  $380,000 Sold Sep 15, 2025

  68 Southside Dr, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • Built 1940

  Last Sold Summary

  • 15% Below List Price
  • $233/SF
  • 49 Days On Market

  Current Estimated Value $400,017

  Last Listing Agent Carol Buchanan BHG Real Estate Green Team

  68 Southside Dr, Monroe, NY 10950
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  Est $425,201 Not Listed For Sale

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

  48 Maple Ln, Monroe, NY 10950

  48 Maple Ln, Monroe, NY 10950
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  $1,050,000

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

  4 Camelback Rd, Chester, NY 10918

  The one you don't to miss. 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 meticulously

  Alexander Fayn Prominent Properties Sotheby's

  4 Camelback Rd, Chester, NY 10918
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  $850,000 Sold Oct 22, 2025

  284 Bull Mill Rd, Chester, NY 10918

  • 5 Beds
  • 3 Baths
  • 3,485 Sq Ft
  • Built 1997

  Last Sold Summary

  • $244/SF
  • 20 Days On Market

  Last Listing Agent Jayne Mangieri Keller Williams Valley Realty

  284 Bull Mill Rd, Chester, NY 10918
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  Est $396,229 Not Listed For Sale

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

  68 Evan Rd, Warwick, NY 10990

  68 Evan Rd, Warwick, NY 10990
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  /17

  $59,900

  • Land
  • 1.89 Acres
  • $31,693 per Acre

  71 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

  71 Carriage Knoll Rd, Chester, NY 12817
• 

  $475,000 Sold Feb 18, 2025

  14 Twin Brooks Dr, Chester, NY 10918

  • 4 Beds
  • 1.5 Baths
  • 1,692 Sq Ft
  • Built 1968

  Last Sold Summary

  • 3% Below List Price
  • $281/SF
  • 50 Days On Market

  Current Estimated Value $498,004

  Last Listing Agent Layla Rose Boyles Century 21 Realty Center

  14 Twin Brooks Dr, Chester, NY 10918
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  Est $335,502 Not Listed For Sale

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

  25 Darin Rd, Warwick, NY 10990

  25 Darin Rd, Warwick, NY 10990
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  $740,000

  • 4 Beds
  • 3.5 Baths
  • 2,780 Sq Ft

  7 Park Place, Chester, NY 10918

  Welcome to your private, wooded oasis! This charming home perfectly blends convenience with comfort, featuring an ideal layout for multi-generational living or guests with two bedrooms and a full bathroom on the main floor. A cozy wood insert is the heart of the main living space, creating both warmth and a wonderful ambiance on chilly evenings. Beyond the existing bedrooms, there is additional

  Luanne McGann Century 21 Full Service Realty

  7 Park Place, Chester, NY 10918
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  $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 $555,322

  Last Listing Agent Donald Serotta Howard Hanna Rand Realty

  1 Winding Trail, Chester, NY 10918
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  Est $835,886 Not Listed For Sale

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

  215 Ridge Rd, Chester, NY 10918

  215 Ridge Rd, Chester, NY 10918
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  $425,000 Pending

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

  16 Oakland Ave, Chester, NY 10918

  .

  Vikki Garby BHG Real Estate Green Team

  16 Oakland Ave, Chester, NY 10918
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  $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 $609,540

  Last Listing Agent Dana Posner Howard Hanna Rand Realty

  411 Prospect Rd, Chester, NY 10918
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  Est $498,470 Not Listed For Sale

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

  201 Hambletonian Rd, Chester, NY 10918

  201 Hambletonian Rd, Chester, NY 10918
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  /2

  $499,000

  • Land
  • 4.5 Acres
  • $110,889 per Acre

  1414 Kings Hwy, Chester, NY 10918

  5 Lot subdivision which has been engineered and submitted to Chester planning board for approvals with water and sewer. Not approved but in the process. Buyer must finish. Site plan in documents as well as addressed planning board comments. Additional Information: SoilType:Unknown,

  Joe Distelburger Keller Williams Realty

  1414 Kings Hwy, Chester, NY 10918
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  $545,000 Sold Jan 17, 2025

  128 Booth Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,102 Sq Ft
  • Built 1975

  Last Sold Summary

  • 16% Below List Price
  • $259/SF
  • 179 Days On Market

  Current Estimated Value $576,217

  Last Listing Agent Tracy McNamara Keller Williams Realty

  128 Booth Rd, Chester, NY 10918
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  Est $717,984 Not Listed For Sale

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

  590 Craigville Rd, Chester, NY 10918

  590 Craigville Rd, Chester, NY 10918

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