Chester, NY Homes

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  $499,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,934 Sq Ft

  6 Vista Dr, Chester, NY 10918

  Stunning Chester Home with Pool, Pond & Private Backyard Oasis! Discover your own private retreat in this meticulously maintained 3-bedroom, 2.5-bath home in Chester. Perfectly positioned for privacy on a scenic lot featuring its own backyard pond, this property offers a rare combination of comfort and outdoor amenities. Step inside to a bright and airy main level where hardwood floors connect

  Christine Koenig Keller Williams Realty

  6 Vista Dr, Chester, NY 10918
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  $550,000 Sold Apr 23, 2025

  16 Fernglade Ct, Chester, NY 10918

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

  Last Sold Summary

  • 13% Above List Price
  • $165/SF
  • 12 Days On Market

  Current Estimated Value $645,044

  Last Listing Agent Kim Chiapperino RE/MAX Benchmark Realty Group

  16 Fernglade Ct, Chester, NY 10918
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  Est $590,157 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,910 Sq Ft

  38 Rebecca Rd, Chester, NY 10918

  38 Rebecca Rd, Chester, NY 10918
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  $129,000

  • Land
  • 13.33 Acres
  • $9,677 per Acre

  L9 Bird Pond Rd, Chester, NY 12853

  Private 13+ acres of gently sloping land just minutes from Gore Mountain. Roughed-in driveway/Road leading from Bird Pond Rd. Several nice building locations around the property. One house-site staked-out for reference. Possible views from higher on the property with some select clearing. Listing agent will provide one set of existing preliminary building plans for the future homeowner from

  Walter Swartz Gallo Realty ADK Inc

  L9 Bird Pond Rd, Chester, NY 12853
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  $602,000 Sold Feb 13, 2025

  19 Mount Ridge Ct, Monroe, NY 10950

  • 4 Beds
  • 2.5 Baths
  • 2,698 Sq Ft
  • Built 2000

  Last Sold Summary

  • 9% Above List Price
  • $223/SF
  • 15 Days On Market

  Current Estimated Value $641,014

  Last Listing Agent Christian Baez Keller Williams Hudson Valley

  19 Mount Ridge Ct, Monroe, NY 10950
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  Est $592,453 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,411 Sq Ft

  32 Rebecca Rd, Chester, NY 10918

  32 Rebecca Rd, Chester, NY 10918
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  $1,100,000

  • 4 Beds
  • 3.5 Baths
  • 4,467 Sq Ft

  53 Odyssey Dr, Chester, NY 10918

  Welcome to an extraordinary 4,400+ square foot residence in the coveted Warwick School district, where luxury and lifestyle converge to create the ultimate entertainer’s dream. This meticulously maintained and thoughtfully updated home offers breathtaking panoramic views, inviting you to unwind in the serene front atrium or the sun-drenched sunroom at the rear. Step inside to discover a

  Hilary Ryan Goldman Howard Hanna Rand Realty

  53 Odyssey Dr, Chester, NY 10918
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  $960,000 Sold Jun 05, 2025

  53 Gibson Hill Rd, Chester, NY 10918

  • 5 Beds
  • 4 Baths
  • 5,312 Sq Ft
  • Built 2010

  Last Sold Summary

  • 4% Below List Price
  • $181/SF
  • 45 Days On Market

  Current Estimated Value $1,012,659

  Last Listing Agent Roxanne Hartman Timothy W. Kramer

  53 Gibson Hill Rd, Chester, NY 10918
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  Est $647,496 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,861 Sq Ft

  8 Valerie Dr, Chester, NY 10918

  8 Valerie Dr, Chester, NY 10918
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  $309,900

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft

  111 Lake Region Blvd, Monroe, NY 10950

  Charming 2BR/1BA ranch on a level lot featuring an oversized detached 2-car garage and rear deck. Bright eat-in kitchen with ample cabinetry and vinyl plank flooring. Rear deck overlooks a spacious, usable yard—ideal for outdoor enjoyment. Convenient location close to shopping, schools, and major commuter routes. Great opportunity for owner-occupants or investors alike.

  Donna Ramundo Keller Williams Valley Realty

  111 Lake Region Blvd, Monroe, NY 10950
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  $380,000 Sold Jul 30, 2025

  3816 Whispering Hills, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Above List Price
  • $285/SF
  • 28 Days On Market

  Current Estimated Value $385,875

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  3816 Whispering Hills, Chester, NY 10918
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  Est $626,009 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,904 Sq Ft

  3 Stacey Ln, Chester, NY 10918

  3 Stacey Ln, Chester, NY 10918
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  $525,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 1,792 Sq Ft

  32 Poplar Dr, Monroe, NY 10950

  GREAT house! If you are looking for move in ready this is IT!!! New kitchen and baths! Either new floors or redone hardwood. Freshly painted. Beautiful paver walkway! New Boiler 2023, Water Heater 2023, Ductless 2022, Roof 10 years old.

  Ann Marie Hahr Keller Williams Realty

  32 Poplar Dr, Monroe, NY 10950
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  $460,000 Sold Mar 24, 2025

  14 Mari Rd, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,926 Sq Ft
  • Built 1970

  Last Sold Summary

  • 10% Above List Price
  • $239/SF
  • 12 Days On Market

  Current Estimated Value $473,780

  Last Listing Agent Martha Randazzo Howard Hanna Rand Realty

  14 Mari Rd, Chester, NY 10918
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  Est $554,663 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,080 Sq Ft

  56 Goosepond Mountain Rd, Chester, NY 10918

  56 Goosepond Mountain Rd, Chester, NY 10918
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  $500,000

  • Land
  • 0.83 Acre
  • $603,355 per Acre

  0 Main St, Chester, NY 10918

  Open commercial lot directly behind the existing Cumberland Farms and just to the east of the former Brookside carwash. Good use may be for a parking lot for a building built on 42 Brookside.

  Claude Brischoux Keller Williams Realty

  0 Main St, Chester, NY 10918
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  $799,900 Sold Sep 15, 2025

  40 Mountainside Dr, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 2024

  Last Sold Summary

  • $320/SF
  • 47 Days On Market

  Current Estimated Value $651,202

  Last Listing Agent Karen Gauvin Our House Real Estate Group

  40 Mountainside Dr, Chester, NY 10918
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  Est $725,561 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,740 Sq Ft

  149 Creamery Pond Rd, Chester, NY 10918

  149 Creamery Pond Rd, Chester, NY 10918
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  $349,999

  • Land
  • 4.9 Acres
  • $71,428 per Acre

  8 Camelback Rd, Chester, NY 10918

  Nestled at the end of a private cul-de-sac, this 5 acre homesite offers breathtaking mountain and valley views in the sought-after Bull Mill Road area of Monroe/Chester, NY. The property’s gentle slopes create the perfect opportunity for a walkout lower level, allowing you to capture spectacular sunsets. This shovel-ready, fully approved, and engineered building lot features Belgian block

  James Feldhaus eXp Realty

  8 Camelback Rd, Chester, NY 10918
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  $565,000 Sold Feb 27, 2025

  9 Laroc Rd, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,810 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Above List Price
  • $312/SF
  • 11 Days On Market

  Current Estimated Value $591,227

  Last Listing Agent Nathen Singer MK Realty Inc

  9 Laroc Rd, Chester, NY 10918
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  Est $676,367 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,436 Sq Ft

  169 Creamery Pond Rd, Chester, NY 10918

  169 Creamery Pond Rd, Chester, NY 10918
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  $68,900

  • Land
  • 3.26 Acres
  • $21,135 per Acre

  98 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

  98 Carriage Knoll Rd, Chester, NY 12817
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  $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 $569,922 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,136 Sq Ft

  7 Mount Ridge Ct, Monroe, NY 10950

  7 Mount Ridge Ct, Monroe, NY 10950
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  $350,000

  • Land
  • 2 Acres
  • $175,000 per Acre

  220 Oxford Rd, Chester, NY 10918

  A rare opportunity in Blooming Grove! This beautiful and flat 2-acre property offers endless potential in a calm and peaceful setting with a road frontage. Conveniently located just minutes from Prospect Garden, the land sits within the Monroe-Woodbury School District. With easy access to permits, this property is ideal for building your dream home or future investment. The neighborhood holds

  Chaim Weiss Exit Realty Venture

  220 Oxford Rd, 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 $346,330

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  1610 Whispering Hills, Chester, NY 10918
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  Est $428,228 Not Listed For Sale

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

  465 Meri Ln, Monroe, NY 10950

  465 Meri Ln, Monroe, NY 10950
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  $534,900 Pending

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

  80 Pewter Cir, Chester, NY 10918

  Welcome to the Villas at Sugar Loaf — an unbeatable location that rarely sees homes come on the market! Just half a mile from the charming hamlet of Sugar Loaf, this beautifully maintained move-in ready townhome is in the highly sought-after Warwick School District. With easy access to major highways and train stations, this home is ideal for commuters. Inside, you’ll love the bright, open floor

  Julie Klein BHG Real Estate Green Team

  80 Pewter Cir, 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 Epique Realty

  2317 Whispering Hills, Chester, NY 10918
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  Est $387,629 Not Listed For Sale

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

  463 Meri Ln, Monroe, NY 10950

  463 Meri Ln, Monroe, NY 10950
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  $500,000

  • Land
  • 9.78 Acres
  • $51,125 per Acre

  30 Harding Way, Chester, NY 10950

  An exceptional opportunity for builders and investors in the highly desirable Town of Chester and Town of Monroe, within the Monroe–Woodbury School District. This offering includes four contiguous lots for the price of one, providing significant development potential. The assemblage consists of 30 Harding Way (0.18 acres; Section 27, Block 3, Lot 11), sold together with the adjoining parcels: Lot

  Ida Payne Keller Williams Realty

  30 Harding Way, Chester, NY 10950
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  $415,000 Sold Jan 23, 2026

  47 Greycourt Ave, Chester, NY 10918

  • 4 Beds
  • 1.5 Baths
  • 1,386 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $299/SF
  • 81 Days On Market

  Last Listing Agent Pedro Garcia Curasi Realty, Inc.

  47 Greycourt Ave, Chester, NY 10918
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  Est $399,603 Not Listed For Sale

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

  321 Heritage Ln, Monroe, NY 10950

  321 Heritage Ln, Monroe, NY 10950
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  $75,000

  • Land
  • 12 Acres
  • $6,250 per Acre

  L62.2 Moffitt Rd, Chester, NY 12817

  12-acre parcel offering beautiful terrain and privacy, yet on a town-maintained road. Plenty of options for a home setting. A very desirable property for your future home construction. Only 15 minutes to Gore Mountain Ski Area, 3 miles to Loon Lake and within a mile of the Hudson River. A wonderful opportunity to enjoy the Adirondack experience. $75,000

  Carol Monroe Najer Realty

  L62.2 Moffitt 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 $399,531 Not Listed For Sale

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

  301 Heritage Ln, Monroe, NY 10950

  301 Heritage Ln, Monroe, NY 10950
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  $39,500

  • Land
  • 1.82 Acres
  • $21,703 per Acre

  34 Carriage Knolls Rd, Chester, NY 12817

  Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

  Walter Swartz Gallo Realty ADK Inc

  34 Carriage Knolls Rd, Chester, NY 12817
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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 $574,621

  Last Listing Agent Kevin Tuhy Keller Williams Realty

  21 Jeffrey Dr, Chester, NY 10918
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  Est $555,803 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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  $1,395,000

  • 4 Beds
  • 2.5 Baths
  • 3,866 Sq Ft

  2948 State Route 94, Chester, NY 10918

  Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, this pristine 1860 farmhouse blends preserved historic character with thoughtful modern updates. Originally part of the Sears family dairy pasture, the 3,866 sq ft home has been meticulously maintained and features original wide-plank hardwood floors, a striking hand-carved banister, five fireplaces with

  Elizabeth Broderick Tuxedo Hudson Realty Corp

  2948 State Route 94, Chester, NY 10918

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