Chester, NY Homes

• 

  $415,000 Sold May 30, 2025

  18 Miller Dr, Chester, NY 10918

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • Built 1978

  Last Sold Summary

  • 6% Above List Price
  • $363/SF
  • 16 Days On Market

  Current Estimated Value $424,092

  Last Listing Agent Jennifer DiCostanzo RE/MAX Town & Country

  18 Miller Dr, Chester, NY 10918
• 

  Est $552,119 Not Listed For Sale

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

  11 Townsend Place, Chester, NY 10918

  11 Townsend Place, Chester, NY 10918
• 

  

  /2

  $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
• 

  $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 $385,435

  Last Listing Agent Lorrainne Pisciotta Weichert Realtors

  226 Eagleton Dr, Monroe, NY 10950
• 

  Est $652,989 Not Listed For Sale

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

  509 Laroe Rd, Chester, NY 10918

  509 Laroe Rd, Chester, NY 10918
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  /37

  $449,000

  • 4 Beds
  • 1.5 Baths
  • 1,780 Sq Ft

  108 Pine Hill Rd, Chester, NY 10918

  Welcome to your dream home at 108 Pine Hill Rd, Chester, NY, where comfort meets elegance in a spacious single-family abode. This charming home offers a thoughtfully designed layout, featuring a welcoming kitchen with direct outdoor access, perfect for morning coffees or entertaining. The first floor also hosts a cozy living room and a bright family room, both filled with natural light. Upstairs,

  Avi Samet Avion

  108 Pine Hill Rd, Chester, NY 10918
• 

  $475,000 Sold May 15, 2025

  11 N Hudson St Unit N, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1956

  Last Sold Summary

  • 11% Above List Price
  • $317/SF
  • 22 Days On Market

  Current Estimated Value $469,789

  Last Listing Agent Layla Rose Boyles Century 21 Realty Center

  11 N Hudson St Unit N, Chester, NY 10918
• 

  Est $661,460 Not Listed For Sale

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

  16 Bianca Blvd, Chester, NY 10918

  16 Bianca Blvd, Chester, NY 10918
• 

  

  /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
• 

  $701,000 Sold Apr 01, 2025

  3 Sunset Ridge Rd, Monroe, NY 10950

  • 4 Beds
  • 3.5 Baths
  • 3,524 Sq Ft
  • Built 1996

  Last Sold Summary

  • $199/SF
  • 94 Days On Market

  Current Estimated Value $727,955

  Last Listing Agent Nicholas Cuomo Keller Williams Realty

  3 Sunset Ridge Rd, Monroe, NY 10950
• 

  Est $422,407 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,177 Sq Ft

  151 Laroe Rd, Chester, NY 10918

  151 Laroe Rd, Chester, NY 10918
• 

  

  /93

  $1,750,000

  • 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 sets the

  Emily Iason Four Seasons Sotheby's Int.

  69 Cedar Pond Ln, Chester, NY 10918
• 

  $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 $125,299

  Last Listing Agent Nancy Sardo BHG Real Estate Green Team

  26 W Meadow Way, Chester, NY 10918
• 

  Est $734,813 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,592 Sq Ft

  3 Overlook Trail, Chester, NY 10918

  3 Overlook Trail, Chester, NY 10918
• 

  

  /30

  $289,000

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

  3308 Whispering Hills Dr, Chester, NY 10918

  Welcome to your 2 bedroom, 1.5 bathroom town house condo with a one car garage in the highly desirable Whispering Hills Community in Chester, NY. Well maintained and cared for by its original owner, this unit is located in a nice private section along a green space. The second floor features two spacious bedrooms and one full bathroom. The primary bedroom has cathedral ceilings and a sizable

  Joseph Paoli Howard Hanna Rand Realty

  3308 Whispering Hills Dr, Chester, NY 10918
• 

  $350,000 Sold Mar 24, 2025

  21 Angle Dr, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,953 Sq Ft
  • Built 1991

  Last Sold Summary

  • 45% Below List Price
  • $119/SF
  • 267 Days On Market

  Current Estimated Value $466,153

  Last Listing Agent Avi Samet Avion

  21 Angle Dr, Chester, NY 10918
• 

  Est $786,377 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,422 Sq Ft

  109 Restdale Rd, Chester, NY 10918

  109 Restdale Rd, Chester, NY 10918
• 

  

  /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
• 

  $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 $524,848

  Last Listing Agent Philip Szumlaski Keller Williams Realty

  10 Tulip Ln, Monroe, NY 10950
• 

  Est $1,175,380 Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 6,622 Sq Ft

  282 Laroe Rd, Chester, NY 10918

  282 Laroe Rd, Chester, NY 10918
• 

  

  /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
• 

  

  /39

  $579,000 Sold Jun 12, 2025

  2754 Schroon River Rd, Chester, NY 12817

  • 3 Beds
  • 2 Baths
  • 1,665 Sq Ft
  • Built 1989

  Last Sold Summary

  • $348/SF
  • 8 Days On Market

  Last Listing Agent Angie Mead Gallo Realty ADK Inc

  2754 Schroon River Rd, Chester, NY 12817
• 

  Est $576,664 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft

  412 Laroe Rd, Chester, NY 10918

  412 Laroe Rd, Chester, NY 10918
• 

  

  /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
• 

  

  /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 $731,965 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,838 Sq Ft

  53 Elvis Blvd, Chester, NY 10918

  53 Elvis Blvd, Chester, NY 10918
• 

  

  /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
• 

  $829,000 Sold May 12, 2025

  30 Meadow Ave, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 2,700 Sq Ft
  • Built 2024

  Last Sold Summary

  • $307/SF
  • 85 Days On Market

  Last Listing Agent Nancy Sardo BHG Real Estate Green Team

  30 Meadow Ave, Chester, NY 10918
• 

  Est $714,162 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,308 Sq Ft

  40 Valley View Dr, Chester, NY 10918

  40 Valley View Dr, Chester, NY 10918
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  /35

  $999,999

  • 5 Beds
  • 3.5 Baths
  • 4,772 Sq Ft

  2 Garnett Hill Rd, Chester, NY 10918

  A Private Suburban Retreat on Prestigious Garnet Hill. This Center Hall Colonial offers an exceptional residence- refined suburban living with the space, privacy, and sophistication sought by discerning buyers—just about an hour from Manhattan. Positioned on a beautifully landscaped 3+ acre property, the home features approximately over 4,700 square feet of elegant living space, offering 5

  Rachel Baruchov Platinum Realty Associates

  2 Garnett Hill Rd, Chester, NY 10918
• 

  $405,000 Sold Apr 30, 2025

  16 Kerner Dr, Chester, NY 10918

  • 3 Beds
  • 1 Bath
  • 1,222 Sq Ft
  • Built 1962

  Last Sold Summary

  • 9% Above List Price
  • $331/SF
  • 35 Days On Market

  Current Estimated Value $414,584

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  16 Kerner Dr, Chester, NY 10918
• 

  Est $760,796 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,812 Sq Ft

  47 Valley View Dr, Chester, NY 10918

  47 Valley View Dr, Chester, NY 10918
• 

  

  /49

  $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
• 

  $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 $751,507 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,599 Sq Ft

  121 Conklingtown Rd, Chester, NY 10918

  121 Conklingtown Rd, Chester, NY 10918
• 

  

  /5

  $259,000

  • Land
  • 20.18 Acres
  • $12,834 per Acre

  32 Mountainside Dr, Chester, NY 10918

  A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This can truly be a mini-estate with near full privacy plus MOUNTAIN VIEWS!! FULLY ENGINEERED with NATURAL GAS, curb cuts! .... Site map in photos. This is one of only two remaining lots. Some wet-lands on the property. Drive way is not shared - it will be side-by-side with

  Karen Gauvin Our House Real Estate Group

  32 Mountainside Dr, Chester, NY 10918
• 

  $617,000 Sold May 19, 2025

  1301 Kings Hwy, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,676 Sq Ft
  • Built 1835

  Last Sold Summary

  • 10% Below List Price
  • $231/SF
  • 146 Days On Market

  Current Estimated Value $633,148

  Last Listing Agent Susan Walski HomeSmart Homes & Estates

  1301 Kings Hwy, Chester, NY 10918
• 

  Est $635,315 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,636 Sq Ft

  79 Conklingtown Rd, Chester, NY 10918

  79 Conklingtown Rd, Chester, NY 10918
• 

  

  /24

  $295,000

  • 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
• 

  $419,999 Sold Jan 07, 2026

  354 Rande Rd Unit 354, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,698 Sq Ft
  • Built 1999

  Last Sold Summary

  • $247/SF
  • 28 Days On Market

  Last Listing Agent Joel Ayala HomeSmart Homes & Estates

  354 Rande Rd Unit 354, Monroe, NY 10950

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